Wrapping Up

So here we are. It’s been a long, fun yak-shave. Two years and a couple of hundred thousand words exploring the world of gig work and indie consulting.

Some housekeeping items before I share my closing thoughts.

First, if you’re a subscriber, and have paid-up time remaining in your subscription, there’s no need for you to do anything. Sometime in the next few weeks, you’ll get the refund for your remaining months. I’m working on the mechanics of it with Substack support. It’s a bit like putting toothpaste back in the tube.

Second, if you’re subscriber, you can grab the rough-cut draft ebooks (in pdf, epub, and mobi formats) of the Art of Gig archives at this subscriber-only page. I had to break up the material into 3 volumes since it was 217,466 words and Google Docs was choking. The link will go away in a week, so grab the zip now. If you’re not a subscriber, you’ll have to wait for the published Kindle versions, probably out in Fall. Look out for the announcement on my main blog, Ribbonfarm.

Note that this newsletter will get deleted at some point from the Substack site, so the ebooks will be the final archived form of the content.

Where Next?

The Art of Gig is winding down, but the gig economy and the indie/creator economy are just getting started. Obviously bigger, crazier things will continue to happen. Here are some newsletters you may want to check out and subscribe to, to keep up. For more recommendations, follow @yak_collective on twitter. The account tweets out writings from many indies.

  1. From Tom Critchlow: The Strategic Independent is a book, published free online, for indie consultants looking to carve their own independent path. It covers topics such as how to roll your own frameworks, how to navigate the theatre of work and the latest explores the idea of Kairos and Chronos for indie consultants. Subscribe to the newsletter here: https://tomcritchlow.com/strategy/

  2. From Rowan Price who publishes a newsletter called Second Opinion. His blurb: When I started it 2 years ago, I imagined that my schwerpunkt was ideation as a business skill. But 190,000 words later, my wahrerschwerpunkt is definition-ownership – “owning” definitions of words and terms that are important to one’s enterprises. To model this, I publish a dictionary that cross-references the blog-archived newsletter, where I’ve rhetorically asked, What’s Your Dictionary?, posited that Words Are Muscle Memories (or should be) and discussed the 1.5 million year history of Thinking Outside The Box vs Productivity

  3. Paul Millerd has a great newsletter called Think Boundless. “Unexpected takes on the modern world of work. Paul explores our obsession with work and the default path of success and tries to imagine new possibilities for how we can conceive of life, work & what matters.”

  4. Patrick Hollingworth has been working as an indie consultant for the past decade, using complexity, network and ecological sciences to help large staid organisations become less, well, staid. His focus has been on the development of ways to visualise and reconfigure the dynamics of organising within these large organisations. He has been railing against management consultants for some time, which makes him kinda unpopular. He writes sporadically on his personal blog. Here are two recent pieces: this one and this one.

  5. The Overlap by Tim Casasola is a newsletter that helps change agents (indie consultants and internal PMs) foster experimentation loops in their respective organizations. Product management meets adaptive organizational design. It comes out every other Wednesday morning EST. Check out: “Strategy vs execution” is not a helpful distinction, Organizations as bounded systems, and See the problem before you so.

  6. Finally, I’ll boost my own main newsletter project, Breaking Smart. It doesn’t have much to do with the gig economy, but I serialize several longer projects there, including the book I’m working on, and a couple of evolving essay collections. As a special thank you for joining me on the Art of Gig journey, you can get 30% off your first year if you subscribe via this link in the next week (by May 6).

The Yak Collective

One of the best things to come out of this 2-year journey was the Yak Collective, which I helped start last year. It is a network of indie consultants and creatives organized as a leaderless, peer-to-peer decentralized collective. It is slowly turning into a truly special place for you to network with other indies, find leads for gigs, work on your professional development with the support of peers, and get involved in bleeding-edge experiments and projects that we think push the boundaries of what it means to be indie.

Over the last year, we’ve produced a handful of collaborative reports, and are working on several more. I’m part of one active project to design open-source rovers, which we hope will actually end up in space one day, and in the meantime, get us gigs in robotics. There is an active Discord, featuring both live chats on various topics and asynchronous conversations. There is also a newsletter which is currently undergoing retooling, featuring links to writings from members, and outtakes from internal shenanigans.

Whatever I do in the future, by way of being active in the indie consulting community, will be via the Yak Collective (in fact, one of the reasons I’m shutting this newsletter down is to free up time to do more with the Yak Collective). There are dozens of others actively helping build it up into something really unique, and there’s plenty of interesting ways to get involved. So join up.

Closing Thoughts

The world was a very different place when I started this newsletter in May 2019. I was living in Seattle then, and was preparing to move to Los Angeles to take up a nine-month fellowship at the Berggruen Institute. And just as the fellowship was ending, Covid hit. Now, one pandemic, one city move, and two apartments later, I’m wrapping this up.

It feels like I started this newsletter on one planet, and am wrapping it up on a whole different planet.

Looking back at what I’ve written, there’s a surreal space-time-warp quality to the archives. This newsletter has been something like a personal wormhole for me. It was also one of my sources of sanity through some crazy times. Not least because it allowed me to connect with so many others on similar journeys, and swap notes, jokes, insights, superstitions, and learnings.

Thank you all for your companionship on this interplanetary journey we’ve all been on.

Somewhere along the way, I marked my ten-year anniversary as an indie consultant, but the world has been changing so rapidly, I felt like a newbie for much of the time I was writing this newsletter. And now that I am wrapping it up, I feel like a total rube again, in the best possible sense. Writing this newsletter has helped me defeat a sense of jadedness that was looming for me in 2019, and find a beginner mind again.

New planet, new life, new mind.

Obviously, I’ll be continuing my own adventures in the gig economy for the foreseeable future. Yet the very act of reflecting on, and writing about, the journey so far, has changed how I see my own road ahead. My new adventures will be different from my old ones, in large part due to this newsletter. I’ve run out of things to say for the time being, but perhaps I’ll have more to say in another ten years.

There is much to learn yet in the art of gig. Especially now that we’re all on a new planet.

This newsletter is wrapping up, but of course our conversations don’t have to. You can still find me on Twitter at @vgr, on the Yak Collective discord, and at Ribbonfarm and Breaking Smart.

Thank you for reading. I’m sure we’ll be seeing more of each other in the future.

Yakverse: Endgame

Only 1 more newsletter issue to go before Art of Gig wraps up on April 30th! Final reminder — if you want me to boost your newsletter in the last issue, email me a short blurb.

<< Infinity Gig | Yakverse Index 

In the end, it didn’t exactly end, but then again, it sort of did. It is all so recent, and so strange, I don’t know quite what to make of it all. But let me lay out the bare facts for you.

After the shocking events in September last year, which left six people dead, things went crazy for a while, and I was in the thick of it, and then it all went quiet.

Through October and September, I was repeatedly dragged down to the local FBI field office, where I was interrogated by my old friends at the G-Crimes division, Agents Jane Jopp and Guy Lestrode. Suddenly I was seeing a decidedly unfriendly side of them. I was on the wrong side of what was now known as the Potsdam multiple homicide case.

Thanks to the packages addressed to Gao, Anscombe, and myself found at the crime scene, we had all turned into Persons of Interest at the very least. I think, for a while, I was the Prime Suspect. Gao and Anscombe told me they’d been interrogated only once. But me? I was interrogated four times.

Jopp and Lestrode grilled me relentlessly about The Club. They grilled me about work I’d done with Khan. They grilled me about the Ancient One. They grilled me about the Potsdam group. I told them truthfully that I knew nothing more about anything than I’d told them on the very first day.

But they didn’t ask about was the monk. Or the yak coins, real or fake. Or the strange yin-yang yak-head coins found in the clenched fists of the six corpses.

As for Agent Q, he seemed to disappear entirely.

The final time I was interrogated, in early January (around the time of that shitshow at the Capitol around the Biden inauguration), Jopp and Lestrode seemed tired and resigned. They’d clearly run out of leads.

I figured I was probably no longer a suspect, and decided to venture some questions of my own.

“What happened to those packages Khan left for us? Are we ever going to get them? What was in them?”

“Just some old manuscripts. Agent Q took them so you’ll have to ask him. He said they were about that Yak bullshit you all seem obsessed with. Or Yakshit I suppose”

“Where is Agent Q? Is he no longer on this case?”

Jopp shook her head impatiently, “We don’t report to him, he doesn’t report to us. He’s off somewhere chasing down after those counterfeit coins and that monk character. He has some sort of fixation there. Like Javert in Les Miserables. No, the counterfeit coins thing is a red herring. Some sort of international art and antiques counterfeiting ring I suppose. Not motive for six homicides.”

“So what’s this about then?”

“What do you think? It’s all about the Potsdam group and that Club you and your buddies were working for. Something big was going down at that dinner party. Something someone powerful wanted stopped.”

“We weren’t working for them,” I protested. “Like I keep saying, Khan just told us they’d be making things happen for us. We didn’t even know who they were. I swear.”

Jopp waved the protest away irritably.

“Maybe I believe you. It really doesn’t matter. Whatever this was about, it was bigger than the sort of two-bit hustling you get up to, no offense.”

That stung, but I let it go. Big picture, two-bit hustler or not, I was at least no longer a Person of Interest.

Lestrode said, “So you’re sure there’s nothing more you can tell us?

“I’ve told you everything,” I said.

And that was the last I heard from any of them until last week.

***

In the months following the murders, Gao, Anscombe, and I got into the habit of meeting up at the park every couple of weeks, to catch up.

We’d sit on the grass, six feet apart, and talk about gigs, geopolitics, the China trade war, the Presidential transition, NFTs, machine learning (which Anscombe was getting deep into), and of course Covid and vaccines.

But one thing we didn’t talk about was the case.

Occasionally, we’d spot an unmarked white van parked across the street from our usual spot in the park. The driver would occasionally glance at us. We were being watched, and G-crimes wanted us to know it.

It was at the most recent of these meetings though, last week, that things finally came to a resolution of sorts. Or didn’t. You’ll have to decide.

On the morning in question, the three of us met up as usual. There was no van watching us that day. There hadn’t been one several weeks. Perhaps they’d stopped watching us?

I was tired and irritable, having slept poorly, with weird dreams, for several days. Strangely enough, Gao and Anscombe looked red-eyed and tired too.

“Looks like we all slept badly, huh?” I said, loosening my mask a little and settling down on the grass in our usual spot in the park, slightly off the main path.

Anscombe said, “The last few nights actually. I keep having these weird dreams. There’s some sort of dark forest, and then it turns into a stormy ocean, and there’s this Cthulhu-like thing with tentacles….”

“…thrashing around, and then it turns into Tibet and there’s a bunch of yaks grazing all around,” Gao finished.

We all looked at each other, startled.

“We’ve all been having the same recurring weird dream?” I said.

Anscombe said, “Coincidence. Probably just Lovecraftian energy on TV. Big mood.”

“Who is Lovecraft?” asked Gao.

***

Before either of us could respond, a new voice interrupted.

“Thought we’d find you guys here.”

I turned around to look. Jopp and Lestrode were walking up the path, towards us. They’d parked where the surveillance van usually did. We hadn’t noticed them pull up.

I almost didn’t recognize them at first — they were in casual clothes rather than their usual suits. They’d traded their trademark black briefcases for a handbag and a backpack respectively.

“Agent Jopp! Agent Lestrode! Long time no see!” said Gao.

“Just plain Jane Jopp and Guy Lestrode now. We’re no longer with the FBI.”

“What! What happened?” I asked.

Jopp shrugged, settling down on the grass. “They shut down the G-crimes division. The new administration seems to want to legislate the gig economy out of existence, not police it.”

Lestrode settled down next to her, and said, “The white collar crimes guys took over all our cases. Most of our division got reassigned there as well.”

“But you two didn’t?”

“We quit.”

“G-crimes was our little indie outfit within the FBI. We got to play by our own rules. We were free agents really. Just a couple of dozen of us. Good times.”

“I guess neither of us wanted to get absorbed back into the big mainstream FBI bureaucracy.”

“So you are…”

“Actual free agents now, yes. Same as you guys,” said Jopp.

“Got any leads for gigs? Not kidding. I’m getting a PI license. Looking to get into corporate security,” said Lestrode.

“What happened to the Potsdam case? Are we finally cleared? Or are we going to get hauled down to the field office by the new guys now?”

“They might drop by for a quick chat, but we basically cleared you three before we handed over the case. You’re welcome.”

“And the case?”

It’s effectively a cold case now. Not even a cause of death to work with. It wasn’t the wine. At least nothing we could detect. Apparently they all had heart attacks at the same time. Probably one of those undetectable new synthetic poisons.”

“What about the other leads?”

“They mostly went nowhere. We did crack that list of code names and encrypted strings though. Not that it was much use.”

“You did?”

“Khan had the decryption key on his phone. Part of each string was a city name. Thirty four major cities, each appearing between one and four times on the list. Eighty entries in all. The rest was numbers. We couldn’t figure out what they were.”

“Which cities?”

“All over the world. A couple each from Hong Kong, Singapore, Seoul, Mumbai. Four from London. One each from Rio, Moscow, Rome, Dubai…”

“But no luck with the code names? All that Zeus, Prometheus stuff?”

“Aliases we think. The list was almost certainly the Club, the one Khan mentioned to you. The group behind him and his buddies. Except we think they were actually part of it, not merely representing it. Some sort of power broker network. Agent Q’s agency had identified about a dozen of them from other leads, but we only had aliases for the rest.”

“What is this agency Agent Q worked for? You never did tell me, and neither did he.”

Jopp shrugged. “He never told us either. He had all the right clearances, and we had orders coming down from on high to cooperate with him.”

“So what was this power-broker network? This Club? Or at least the ones you could identify?”

“Big Three consultants, old economy bagmen, failsons, Davos types, influence peddlers for dictators, academics on the take. The usual crowd. Why they thought you three small-timers were worth bothering with, I don’t know.”

“What about the victims? Were they part of the Club?” Gao asked.

“The six victims were from the six American and Canadian cities on the list, so yeah. Can’t be a coincidence. We think North America was the core of the network, and this Potsdam group was the ring leaders. Some sort of internal coup perhaps. Maybe that monk character Q was chasing was the assassin. Maybe the Asian faction was trying to take over the Club from the North American faction. Or maybe it was just a cult suicide. Not my case anymore, so I don’t really care.”

“What about the Yak angle. The coins. Those manuscripts Khan left for us?”

“Oh yeah, Q mailed them back to us a couple of weeks ago, just before we quit. There was a note to hand them over to you guys. That’s why we’re here actually,” said Lestrode.

He reached into his backpack, pulled out the three packages, and handed them to us. They’d been opened and resealed.

“I still think that whole angle was a red herring. This gang was into toppling governments and corporate takeovers. Maybe even assassinations. Counterfeiting antique coins doesn’t seem to fit,” said Jopp.

I opened mine and took a quick look. It was, as Jopp had said, an old manuscript, in Tibetan. An inch thick, with the head of a yak embossed on the red cover. Gao and Anscombe were looking at their packages too. Their manuscripts seemed identical, except that their covers seemed to be green and yellow respectively.

Lestrode sniggered, “If this were a comic book, you three would be Keepers of the Books. Keeper of the Red Book, Keeper of the Green Book, Keeper of the Yellow Book. I’d just try to sell them on eBay if I were you. Probably worth a bit to collectors.”

Jopp said, “The package was shipped from Bhutan. So I guess Q is still down there chasing his monk. Well, it’s his wild goose to chase.”

“Or his wild yak to shave,” I said.

A new voice spoke. A voice I’d last heard a decade ago, in Bhutan.

“Very clever, Mr. Rao. How’s that working out for you?”

***

The monk did not appear to have come down the path. He looked like he’d just stepped out from behind the clump of trees next to the patch of grass we were sitting on. Or at least he must have. None of us saw him approach.

I am referring to him as the monk, because he’d been dressed like one when I’d first met him in Bhutan in 2011, and because that’s what Agent Q had called him. But this time, he was in jeans and a hoodie. He didn’t appear to have aged at all. Still old, but no older.

An ageless old monk in youthful jeans and a hoodie. Yet, somehow, the effect was not incongruous.

He walked up and joined our circle, arranging himself neatly cross-legged and straight-backed, hands resting lightly in his lap. Perhaps he was a monk after all.

Jopp, Lestrode, and Anscombe were staring open-jawed.

Gao, like me, looked both surprised and surprised. I’d always suspected he too, like me, had had a previous encounter with the monk and his magic tricks.

“Where did you come from?” I asked.

“From over there,” he gestured vaguely at the woods behind us. “I was out for a walk and spotted your little group here and decided to join you. Lovely spring day, isn’t it? I see you’ve gained some weight and grey in your hair since we last met, Mr. Rao. You should really try butter tea.”

He turned to Gao, “And nice to see you again as well, Mr. Gao.”

There was silence for a moment. Nobody seemed to have anything to say.

Finally, Jopp found her voice. And apparently, her investigative instincts as well. She reached for her phone.

“I think, Sir, if you are who I think you are, you have a few questions to answer. And I think I’d better make a few calls.”

“I thought you were no longer with the FBI, Ms. Jopp? Perhaps you will indulge me for just a few moments. But by all means, make your calls if you must.”

Jopp hesitated, then put her phone down, and glanced at Lestrode. Then back at the monk.

“How about you start with your name, and we’ll go from there.”

The monk, waved her question away.

“My name does not matter.” He turned towards me, Gao and Anscombe. “I see the three of you finally have the packages I left for you. Q is a man of his word. He will do well as my successor.”

“Well at what? What do you mean your successor. Are you with the same agency?” Jopp asked.

“You left the packages for us? Not Khan?” I asked, at the same time.

The monk turned to Jopp first.

“I’m afraid Q misled you. Like all of us here, he is a free agent. Just one with a very particular set of skills. He is exceptionally skilled at appearing to be the agent of larger organizations.”

“So he found you?”

“It would be more accurate to say I allowed myself to be found. It was time, and he was finally ready.”

“What do you mean? And how is he your successor?”

“My dear Ms. Jopp! I mean merely that your former associate is merely covering for me in… one of my long-term Bhutanese gigs, shall we say? For a few yak coins.”

“So this is about the Order of the Yak? That’s a real thing then?”

“Of course not! The Order of the Yak has not existed for a thousand years. The coins are merely a sentimental memory now. Some of us merely play games with them out of nostalgia. Unless you are referring to the little online community Mr. Rao here has helped instigate.1 I am not part of that charming little experiment I am afraid. I do wish it well though. Great transformations must rest on little experiments after all.”

He turned to me.

“To answer your question, Mr. Khan and his dinner guests had other plans for the manuscripts, but they all saw the wisdom in my suggestion that the manuscripts should pass into more appropriate hands.”

Lestrode pounced, “Ah, so you were there the night of the murders. We have you on the front door security camera, but now by your own admission, you were inside too.”

“Of course I was. Where else would I be? It was time.”

“So you admit it! You killed them!” Lestrode was on his feet now, reaching for his phone.

“Me? No. I was merely present as a witness when they recognized the folly of the path they were on, and did what had to be done.”

“Folly? What folly?”

“It is always the same folly isn’t it? Whenever great transformations are underway, there are those who believe they need not change, even if others must.”

“What great transformation?” Jopp asked suspiciously.

“Come now, Ms. Jopp. You too have been a free agent now for several weeks, as has your former colleague Mr. Lestrode. Surely you read about it in the news? Feel it in your bones? See it in your dreams and nightmares? The world is changing. Changing deeply. A New Normal is indeed on its way.”

As he spoke, he turned to Gao, Anscombe, and me in turn, looking steadily and kindly into each of our eyes in turn.

“Don’t worry. The dreams will fade in a few weeks.”

Then he turned back towards Jopp and Lestrode.

“You will begin to feel it soon enough. You have the attunement. You are true indies. I am confident I have chosen well.”

“Chosen?”

The monk smiled, “I’m afraid it is time.”

“Time for what?” I asked.

“Time for me to go. You will not see me again, but I expect you will see your friend Q now and again.”

And with that, he began to fade slowly (and I have to say, somewhat theatrically), dissolving into a gentle flurry of orange leaves, his smile fading last of all.

We all stared stupidly at the pile of leaves that remained where he’d been a few seconds ago. It looked strange on the ground there, an anachronistic patch of fall in early springtime.

I realized I was clenching my fist. There was something in it. I opened it.

It was a coin.

A coin that looked exactly like the strange yak-head yin-yang yak coins that the victims in the Potsdam case had been clutching.

I looked around. The others were unclenching their fists and staring at coins too. And somehow, I knew that they were in fact the same coins.

We all looked at each other.

“Weren’t there six coins? There’s five of us here,” Lestrode said.

“Maybe Q has the sixth one?” Anscombe said.

“I don’t think so,” said Gao thoughtfully. “The monk said Q was his successor. We are five are the Chosen Ones. That seems… different.”

“Whatever that means,” said Jopp.

“I think, I might know who…” I began.

My phone dinged. It was a message from my brother, Mycroft Rao.

Do you know anything about this?

A picture followed. A picture of the sixth yin-yang yak-head coin in Mycroft’s palm.

“I think,” I said, looking up, “we have a dinner for six to plan, once we’re all vaccinated.”

Note: This newsletter will be shutting down on April 30th, 2021, and the archives published as an eBook.

To simplify the shut down, new subscriptions have now been turned off and existing subscriptions have been paused. Existing subscribers will still be able to access the paywalled archives until the list shuts down in May. The rest of you will have to wait for the ebook.

Building a Sparring Business

Only 2 more newsletter issues to go before Art of Gig wraps up on April 30th!

Last year, I wrote a 3-part series1 on executive sparring, but never quite wrapped it up neatly. So that’s been on my to-do list before I wrap this newsletter.

  1. In Part 1, Introduction to Executive Sparring (May 14, 2020), I set up the basic idea, and explained how it is different from things like coaching, how and where you can learn the skill, and what traits it takes to be good at it.

  2. In Part 2, The Guru Factor (May 21, 2020), I explored what kind of epistemic posture is appropriate for sparring (you bring an appreciative view on instrumental knowledge as an emissary of the adjacent possible) and how to manage perceptions (including self-perceptions) around labels like “Guru” and “Pundit” so you can be effective.

  3. In Part 3 I’m Okay, You’re Not So Hot (June 3, 2020) I explored how to set up what I call the “problem social graph,” as the context for the sparring, based on the operating assumption that your client is not the problem; other people in their organization are.

In the first three parts, I circled, but never quite got to what I consider to be the solid knowledge foundation on which to build a sparring business. So let’s wrap up the series by addressing that question.

What Are You a Guru Of?

For better or worse, having a guru factor going is kinda necessary for sustaining a sparring practice as your core indie consulting activity, as opposed to just occasionally doing sparring on the side of other activities.

The big question I set up in Part 2, as a way to understand the knowledge foundations that your sparring practice is based on, was:

Next time, we’ll talk about the actual content of accumulating appreciative knowledge, the content of your guru-factor, but to set it up, consider the opening question: what are you a guru of?

“Nothing!” is a perfectly fine answer.

To be a guru of something is to look at the world through that thing rather than being put in a box defined by that thing. There are no restrictions on what you’re allowed to look at. The thing you’re a guru of is merely the appreciative perspective on the world people associate with you.

To be clear, as I’ve repeatedly emphasized in this series, I don’t recommend you self-consciously set out to “become a guru.”

But if the behaviors that lead to one eventually crystallizing come naturally to you, then you have a choice about whether to be open to that outcome or not.

One of the reasons to be open to gurudom is that it opens up the option of sparring-partner type consulting work.

Which is worthwhile because it is fun, stimulating, relatively undemanding in terms of time, and to be frank, relatively easy compared to many other ways of making similar amounts of money, and a great career option for lazy people.

My intent with this series has been to set you up to recognize and deal with what’s happening if gurudom descends on you (or if it already has), whether or not you asked for it. Gurudom is a bit like becoming randomly internet famous for a silly viral video. Depending on who’s looking, gurudom can look like a halo, or a stink around you. Some people will look up to you, others will see you as a lolcow. You don’t get one without the other.

It’s not quite a career outcome you can plan, study, and train for, but certain behaviors make it more likely to happen than others, and of course, you have to be open to it happening to you.

It’s also not a career outcome that obviously leads somewhere, the way landing a VP role leads naturally to being in contention for a CEO role. A guru-factor descending on you kinda just sits there. It doesn’t propel you anywhere necessarily. You have to make up a place to go once it descends… if you choose to be. Doing nothing with a guru factor, once you have the option, is actually a fairly common response. It is a commonly un-exercised option.

But if you choose to do something with it, “sparring partner” is one of those made-up places you can go.

As I explained in Part 2, navigating labels like “guru” is basically a cost of doing business as a consultant, and doubly so if you want to offer sparring services as the core of your consulting. There is no point fighting the perception. All you can do is own the label instead of letting it own you.

So, with that preamble out of the way, what are you a guru of?

Guru Factors vs. Brands

This is one of those questions where if you know the answer, you know it immediately and unambiguously. If you have any doubts at all, you haven’t figured out the answer.

You’ll know it’s the right answer because you’ll feel an odd sort of sense of being trapped by it, but detached from it. It will be something you’re neither proud of, nor ashamed of. It’s something like blood type rather than height or looks. It’s just a fact about you that is overwhelmingly salient to your indie consulting business.

In my case, if you’ve been following my writing/blogging career, the answer is obvious, I’m viewed as a “guru” of pragmatic organizational politicking.

The perception kicked in with the Gervais Principle series that launched both my writing and consulting careers, and I’ve never been able to either get away from it, or significantly recenter around something else.

There’s a bunch of side dishes I offer alongside the main course:

  1. “Fat” thinking over lean

  2. OODA loop stuff

  3. Software eating the world

  4. Working with the Silicon Valley management playbook

  5. Self-aware mediocrity as an executive/managerial ethos

There’s also a number of “guru brand attributes” like a strong bias for history, phenomenology, and anecdotal knowledge over abstract theories and process models/frameworks, a cartoonish association with 2x2s (which is something like a signature “tell” of my style), and so on.

But the core has always been pragmatic organizational politicking.

If you are an executive and you know I exist, I’m probably on a fairly short list of people you might call if you’re trying to get something ambitious done while dealing with organizational politics along the way.

People often want to talk to me about lots of other topics, such as TV shows, storytelling, memes, tech trends, and so on, where I can be generally stimulating company. But they only tend to hire me when they run into a challenges that require modeling and sorting out organizational politics, and understanding what peer executives are doing/trying to do, and why. And how to work for, against, with, or around them as necessary, to do what you want to do.

The thing about being subject to this sort of perception is that:

  1. You have to have one to have a sustainable sparring career

  2. You will hate it for a while once you find it, and feel pigeonholed by it

  3. You must come to terms with it and kinda ironically own it to enjoy it

You’ll know you’ve found your guru factor when you see people referring to you as “that _____ guy” and you react with a slight cringe, but then shrug.

When it’s easier for people to remember your shtick than your name, you’ve found your guru factor. For a lot of people, I am “that guy who wrote that thing about The Office.” Even if your name is easier to remember than mine, your shtick will overwhelm it.

Note though, that your guru factor is not your personal brand, though the two are closely related.

Your brand is how people remember who you are. Your guru factor is the perspective people come to you for.

By way of analogy, consider something like the Hubble Space Telescope. It has a brand as a high-tech, complex, expensive gee-whiz space mission that is a showcase of American technological prowess. Science nerds of all ages love it, and share its photos.

But what people, specifically astronomers, come to it for is a specific set of observational capabilities — visible spectrum from LEO, requiring the aperture size Hubble offers.

If you wanted a different part of the spectrum, like radio, you’d go sign up for time on a different telescope, even if Hubble is your favorite telescope. If you needed observations that were less sensitive to atmospheric distortions or doable with smaller telescopes, you’d go elsewhere (Hubble doesn’t accept observation proposals that can be done by ground-based telescopes).

The “unique telescope” analogy also provides a clue as to how to go about developing a guru factor, the thing you’re a guru of.

Don’t try to be “smart.”

This is the most important thing.

Nobody ever goes to anybody else for the “smart” perspective to complement their “stupid” one. If you think you’re stupid, you look for a therapist or life coach and work on self-esteem issues, not a consultant to help you take on the world.

Being smart may or may not be relevant in becoming known for specific perspectives (obviously, if you are known for surprising neuroscience metaphors, you have to be smart enough to do neuroscience), but people don’t come to you for sparring for the smarts.

Well sometimes, misguided potential clients do, but the first call goes so awkwardly, they realize it’s not actually what they want.

This can be very confusing, because many people will say they came to because you’re “smart,” or “sharp,” but a little digging will reveal that did not. There’s just a lot of general-purpose flattery that goes on in the game of introductions that should not be taken seriously. Even if they genuinely believe you’re smart, or very smart, that’s not why they’re there.

Pro tip: the more extreme their adjectives for you, the less they understand their own motives for reaching out to you. Someone who merely says “I wanted to chat with you because you seem like a smart guy” understands their own motives much better than somebody who says, “I wanted to talk to you because you seem like a super-sharp whip smart, amazing and unique mind.”

Bottomline, “smart” is never part of a guru-factor past a basic minimum. You can’t be a moron, but you don’t need to be a genius either. Mediocre smarts is the sweet spot.

Consume different inputs.

This is the second most important thing.

You learn to see differently — differently enough to sustain a guru-factor shtick — if you’re fundamentally consuming different inputs than most people who talk about the things you talk about.

How you see is a function of what you’ve seen. If you’ve seen the same things as everybody else, it’s hard to see differently from everybody else.

But it only has to different in the target context. Watching lots of mainstream TV isn’t a particularly rare behavior. That was basically my “seeing training.” But it’s an unusual perspective in the context of executive business lives. Executives are rarely big TV watchers because it is a time-consuming pastime for lazy people, not one for people putting in 100 hour weeks. So an eye trained by hundreds of hours on the couch consuming sitcoms is different for them.

Of course, you still have to have enough literacy in their domain to make the connections and talk on common ground about the actual problems. I don’t spend sparring sessions talking to my clients about my favorite episodes of The Office. We talk about whatever they’re actually working on or dealing with. For that, I have to do my homework like any other kind of consultant.

“Difficult” is not “Different.”

This is the third most important thing.

If you learn to think well about difficult topics, that makes you an expert. A pundit. People will come to you for definitive, authoritative expertise, not sparring. They’ll come to you for advice, and then generally take it, because they are not competent enough to spar with you. Conversely, while you need a basic literacy in difficult topics they are experts in, you can’t actually spar with them on that topic. You’re not competent.

So strangely enough, to uncover a guru factor, it’s actually better to immerse yourself in topics that are demanding (in terms of being time consuming) but not actually difficult. Mastering difficult subjects puts you on the pundit track, not the guru track. Other doors open, not the sparring door.

For example, I’ve read a lot of history, and classic, older business literature. It’s not difficult material, it’s just unusual to consume it, since the pop-business literature market is driven by fads, and focused on the most recently published books and ideas. So while many people may have heard of the “Peter Principle” from 1969, surprisingly few working-age people have actually read it or even known to look it up on Wikipedia. For many people much older than me, my 2009 Gervais Principle was actually their first introduction to the idea!

So you just have to have put in the time. In my case, since I started consuming this material in the 80s, I know a lot of “old” stuff that most people my age, or even much older, aren’t usually familiar with. Most people only get into management literature as adults, and more commonly, when they are actually within striking distance of executive roles. It’s not a common teenage nerd interest, so I accidentally started building an advantageous appreciative knowledge perspective in the 1980s.

The Guru-Pundit Divide

Once you’ve answered the basic question, what are you a guru of? or at least figured out what to watch out for and what behaviors to practice, you can ask whether you actually want to be one.

If it seems rather late in the game to be asking that question, it’s because you don’t really understand the question until you have the live option, ready for the exercising, in front of you.

As I’ve said earlier, I believe having a guru factor going is necessary, but not sufficient, for being a good sparring partner. I’ve never met a good sparring partner who was not a guru of something. To spar, you cannot have a “view from nowhere” of the world.

But if you have a live option, and you’re asking the question at all, chances are, there is an unspoken “do I want to be a pundit instead?” secondary question.

You can ask several follow-up questions that clarify this, which I listed in Part 2:

Is your relationship to appreciative knowledge closer to punditry or gurudom?

Here’s a test to tell apart gurus and pundits. In their relationship to appreciative knowledge, pundits prioritize taste, while gurus prioritize insight.

Recall that I defined pundits as people with an instrumental view of appreciative knowledge, as opposed to gurus who have an appreciative view of instrumental knowledge.

If your relationship to appreciative knowledge is grounded in taste and aesthetics, and you appreciate the beauty in a knowledge domain, you’re better suited to being a pundit. You will automatically gravitate towards difficult domains that demand smarts. You will automatically consume the same things others do, but develop a reputation for being a tastemaker, who declares which subset of commonly consumed information is good or bad. You will naturally want to cast what you know in the form of polished workshops and glossy printed artifacts.

A guru on the other, prioritizes discovery of “aha!” insights, and doesn’t much care who discovers them, gets credit for them, or what the discovery says about their smarts.

This is an ideal posture for sparring, since usually insights pop up as part of the process, and don’t say anything much in particular (whether flattering or unflattering) about who uncovered it. It’s like going on a hike together, and one of you points out an eagle in a tree.

It is something of an accident who gets to spot the eagle. The point is going on a hike where interesting things can be spotted.

Is gurudom what you actually want?

Though the popular modern image of a guru is a cult leader who mesmerizes a flock of brainwashed morons, the term actually refers to someone people argue with, and this is the connotation that has carried over to business guru. Where the guru is a teacher of young novices, the aim is to get good enough to argue with the teacher.

This is not actually a pleasant thing for everybody. Many people prefer and expect to be deferred to.

A pundit is someone people defer to. If that’s really what what you want, that’s what you should cop to, and aim to be.

Master a difficult domain that takes smarts.

Start a newsletter to bestow wisdom unto the world.

Make declarations that follow the rough template: This thing is good, that thing is bad. Do this, don’t do that.

It’s a good hustle, and I admire people who do it well. It’s just not something I can do.

If you somehow ended up on the wrong side of that divide relative to your natural inclinations, how do you cross over?

To quote Part 2 again:

Punditry is the result of an instrumental approach to appreciative knowledge. Gurudom by contrast, is the result of an appreciative approach to instrumental knowledge.

(for completeness of the 2×2, an appreciative approach to appreciative knowledge makes you a critic, and an instrumental approach to instrumental knowledge makes you a vocational learner).

Statistically speaking, I’d say about 60% of the population is vocational learners with little to no interest in appreciative knowledge of any sort. Another 30% is critics, focused almost exclusively on consumption tastes, whether or not they are connoisseurs. Of the remaining 10%, I’d say 9% are pundit types, and only 1% are guru types.

This has nothing to do with being unique or special. Gurus are rare because few people are lazy and unambitious enough to hang out on the sidelines, appreciating interesting doings without moving to participate consequentially in them.

Most people have an agency itch. They want to energetically do stuff. Even the critics are way more energetic than the gurus. They energetically consume and analyze what they consume in excruciating detail. All the wine nerds I know are extremely energetic people. All the pundits I know are voracious and hard-working readers and judges of difficult, demanding material.

If you’re reading this at all, you’re unlikely to be a purely vocational learner or a critic. Chances are, you’re either a natural pundit or a natural guru.

9:1 you’re a pundit.

Not that there’s anything wrong with that 🤣.

If so, you’ll probably be miserable sparring. You’ll experience the persistent impulse to speak with careful authority rather than in spitballing mode. You’ll feel more comfortable when you can occupy a “professional” role in a situation (“Alice here is our machine learning consultant”) rather than am amateur hobo type role (“Bob here is this guy I met on Twitter who I thought would be interesting to have in this conversation”). When you have to ask a question, you’ll feel a slight twinge of reluctance at having to “admit” to not knowing the answer already. You’ll get a little dopamine hit whenever people defer to, or validate your sense of expertise, by accepting your recommendations without question.

This is a pundit trapped in a guru role.

I mean, seriously, this is fine. If this is you, go there. Be the pundit. Don’t try to occupy sparring roles. Find a box you feel valued and comfortable in, claim it as your own, and live in it. Exercise the influence that will accrue to you if you’re good at things you claim to be good at. Get yourself out of sparring conversations, and simply reserve the right to distance yourself from decisions you don’t agree with, but don’t want to get into arguments about.

On the other hand, if it’s being the “professional” anything that makes you uncomfortable, if being asked to make a decision for others makes you wary, if having your expertise on some matter validated makes you naturally say self-deprecatory things to mitigate the perception of expertise, if you get a genuine kick out of being the hobo in the room… you might be a guru trapped in a pundit role.

Putting it All Together

I realize this four-part series hasn’t exactly been a cookbook recipe for building a sparring practice. It’s been more of a field guide to recognizing it happening to you, and some hints on what to do more or less of to increase or decrease the chances of it happening to you.

But to put it all together, the way to build a sparring practice is… to spar.

Spar at every opportunity, in every available context, with any and all comers. Whether you’re being paid or not.

Don’t stand on ceremony. Don’t assume arguing with randos on Twitter is a waste of your time. Don’t set uppity conditions and criteria around who is/is not “worth” arguing with. Standards of competence are for pundits.

Don’t let your sense of your own expertise stop you from sparring with anyone unless it’s down to not even having a shared vocabulary. And the funny thing is, if you let lack of shared language stop you, you probably don’t want to spar anyway. People who want to spar generally find different language if necessary. If you have a PhD in a jargon-heavy field, but someone random who lacks the jargon says something insightful about it, you’ll find a way to engage and spar.

Sparring is like writing. You can’t set out to “be a writer.” All you can do is write. And more importantly, rewrite. For sparring, the equivalent of rewriting is simply taking notes and reviewing them periodically, maintaining threads of continuity through extended conversations across many sparring sessions.

So log the hours and the notes, and enjoy it. Do it long enough, and people start coming to you to spar about particular things. At some point a guru factor pops and you have to get over hating it and coming to terms with it. Then at some point you find people want to pay you to spar with you.

Don’t make it too complicated. Keep it caveman simple. Taking a cue from Dan Harmon’s “story circle,” here’s my attempt to reduce it to just 8 words.

  1. Spar as much as you can.

  2. Take notes.

  3. Enjoy it.

  4. Find a guru factor.

  5. Choose to be a guru rather than a pundit.

  6. Accept that you’ll hate it for a while.

  7. Come to terms with it.

  8. Charge money for it.

Spar. Notes. Enjoy. Guru. Choose. Hate. Terms. Charge.

That’s all there is to it. That’s how you build a sparring practice. You just have to do it for long enough.

Note: This newsletter will be shutting down on April 30th, 2021, and the archives published as an eBook.

To simplify the shut down, new subscriptions have now been turned off and existing subscriptions have been paused. Existing subscribers will still be able to access the paywalled archives until the list shuts down in May. The rest of you will have to wait for the ebook.

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There was also a guest post by Tom Critchlow, that explored an bunnytrail of Sparring as Tenure.

Bad Ideas

Only 3 more newsletter issues to go before Art of Gig wraps up on April 30th!

Fifteen years ago, when the modern gig economy was just starting to take off, there was a certain homogeneity to the rosy-eyed takes on the future of work being bandied about. The idea of using the internet to do things in a whole new way was new. Everybody loved all the ideas in the air relatively equally and uncritically — Kevin Kelly’s 1000 true fans, Chris Anderson’s long tail, Tim Ferriss’ 4-hour work-week. It was all good. We were all going to create the brave new world together.

Now that we have more experience, opinions and tastes have started to diverge, and there is the beginning of schools of thought about how to gig. This is a great thing. Dissent is the voice of progress.

I think four main schools are emerging, as shown in the 2×2 below:

I think I personally belong to an emerging pragmatic-romantic school of gig work, where our sensibilities are mainly defined by having a true experimental mindset.

If you’ve been reading this newsletter for a while, you know I’m fairly opinionated on various detailed matters like hourly vs. project billing, but here I’m talking about high-level gestalt ideas that people use to organize all their thinking. Ideas that define their style of gig-working.

Bad as in Defaults

In the experimentalist school, we try things, and stick with them if they work, and abandon them if we don’t. We try to get our shit together, but we don’t try to overfit complicated life philosophies to rough-and-ready working theories of what works for us. We don’t read divine meanings into our own fates.

Often, it’s easier to define yourself in terms of what you reject. With divergence and the rise of different schools of thought, this is inevitable. What you accept tends to be complex, plus you’re too close to it to see it clearly. What you reject on the other hand, is sharply defined and clear.

It struck me that I’ve never actually listed out all the ideas that I think are, to varying degrees, bad. Not perhaps bad for everybody, but also not just bad for me as a matter of personality fit and personal tastes. They are less than universal, but more than personal. They are school-of-thought level beliefs about what is bad that I think are shared by a lot of people, not just me.

I think these are ideas that are bad by default, good by exception.

Most of these ideas are ones I associate with either the Gig Optimizer or Gig Supremacist schools. The Gonzo Gigster school — the romantic idealists — is one I have a lot of sympathy for. They are the mad poets of the gig economy who come up with the biggest new ideas, mixed in with a lot of harmlessly bad eccentric ones. They are the ones who often end up drunk and bankrupt and possibly even dead on the streets, but on rare occasions they get really important flashes of inspiration.

I just don’t have the risk appetite to be truly gonzo myself, but I do have my gonzo moments. But there are people who seem to be almost permanently in gonzo mode (no famous ones — all the famous ones tend to be from the left of the diagram), almost like they’re seeking martyrdom in pursuit of the essence of pure gigdom.

So here’s a list of 10 bad ideas. Again, I emphasize — not universally bad, just bad by default, good by exception. If you’re one of the exceptions for whom it could work, by all means go for it.

The List

Since I’m winding down this newsletter, I’m not really looking to pick beefs or even get off some parting shots. Mostly, I’m just trying to sort of complete the package of ideas that’s been this newsletter. Such a package would not be complete without an honest inventory of what I’m against.

These are not necessarily the top 10 worst ideas (those tend to get weeded out since they work for nobody). These are more like 10 representative bad ideas that illustrate overall bad patterns. They work just often enough that schools of thought can coalesce around them. I think they cluster roughly according to the 2×2, but the classifications are not clean.

So in no particular order…here we go.

  1. FIRE (Financial Independence, Retire Early): An article I found via Paul Millerd led me to doing this short thread on the FIRE idea. In brief, I think it’s a bad idea for most people to plan around hating work and aggressively solving for “retirement.” It is better to process your feelings about work until you find a way to enjoy and pursue it roughly as long as most people around you. To 65 in most parts of the world today. Because work is actually one of the pleasures of life, when done right. FIRE strikes me as a version of what Bruce Sterling calls acting dead. School: Gig Optimizers

  2. Gigworker unions: I’ve been open about this. Unions are an obsolete mode of political organization and action that’s both ineffective and entirely captured by a class of untrustworthy leaders. “Solidarity” as an uncritical socialist value has acquired all the baggage on the left that “patriotism” has on the right. There are emerging alternative novel mechanisms worth exploring that don’t require you to subsume your individuality within some sort of 1920s class identity. School: Gig Supremacists

  3. 4-Hour Work Week: All credit to Ferriss for starting a big part of the gig economy conversation, around how hard you should work, but the specifics of the 4HWW model turn me off. Work should be enjoyable, impactful, and serve a purpose for others beyond just you making a living. When it meets those conditions, most people want to work more than 4 hours a week. Solving for minimal work around passive income streams is another way to act dead. If working 100 hour weeks is masochistic, solving for 4 makes you vulnerable to becoming a grifter. School: Gig Optimizers

  4. Systems and Processes Consulting: Many indies build careers around personally branded process models. The Vogonlogy Pipeline Matrix Method™ or whatever, complete with polished collateral and highly choreographed workshop offerings. 90% of the time, this is vanity bullshit. Quick-and-dirty commodity mental model (a la Weick, What Theory is Not, Theorizing Is) is vastly more valuable and honest. Test of whether your Thing™ is vanity or real: if you open-sourced it and stopped doing it yourself, would others run with it? Or would it be instantly forgotten? The whole advantage of being an indie is that you’re not a part of some bureaucratic machine. If you can’t bring the bespoke quirkiness without the vacuous props, you’re giving the rest of us a bad name. School: Gig Optimizers

  5. Studio Structures: If an indie tries to operate in “studio” mode, trying to package what they do in the form of a Serious Art and Design Institution™ engaging in the Self-Important Critical Practice of XYZ™ while incubating a Portfolio of Pretentious Projects™ … no. It never ends well. It is barely a good idea for proper firms or partnerships of 4-5 people taking on genuine entrepreneurial-artistic capital risks together. But when a single indie acts like they’re a “studio,” it’s almost invariably bad news. Stop posturing and just do shit, and let the shit speak for itself. The “studio” packaging adds nothing but your visibly aestheticized insecurities. Build what infrastructure you need. Don’t fetishize it, or sell it as a theatrical end in itself. School: Gig Supremacists

  6. Certifications: This one especially needs the reminder that I’m talking good defaults. While some consulting-specific certifications are worthwhile, and represent unusual or rare skills (like say specialized training dealing with nuclear disasters or something), and others might be required to operate in particular industries (like PMP or Lean Six Sigma, which I think are bullshit, but worth getting for access to certain kinds of gigs), most “soft” certifications are useless bullshit. Like certified life coach? Come on. Either go get an actual psychiatry or clinical psychology degree, or own your advice-giving shtick without attaching sketchy quasi-credentials. In the worst cases, shady certifications are signs of exploitative grifts. School: Cusp between Gig Optimizers and Experimentalists.

  7. Performative Lifestyles: It’s great that you live on a farm in Podunk, to achieve Work-Life Balance Close to Nature™ or enjoy a Location-Independent Lifestyle. Good for you. But outside of other gigworkers you might be swapping tips with (or more likely showing off to), nobody else cares unless it compromises what you do for others, in which case it is a liability. Keep that shit in the backend. Lead with what you do for others. What you do primarily for yourself, with no benefit (and perhaps even active harm) for anyone else from your doing it, shouldn’t be part of your brand. That just creates narcissistic and self-indulgent optics around the whole gig economy. It’s a bad look for all of us. School: Gig Supremacists

  8. Resentment as a Service: There is a kind of indie posture that involves basically a continuous muttering and whining about the evils of corporations, middle managers, and the paycheck world in general. It is of course, deeply hypocritical if at the same time you’re deriving much of your income from that world. Often this becomes part of the brand: “You are part of the corrupt mainstream world, and I, pure soul, bring to you the cleansing holy water of the indie economy!” Give it a rest. You made a lifestyle choice that worked for you. Don’t presume to sit in judgement of choices made by others. School: Gig Supremacists

  9. Missionary Overcompensation: Many indies have trouble processing the fundamentally mercenary nature of what we do, and an undercurrent of guilt about what feels like taking the easy, privileged way out because you can, while others, mostly in paycheck jobs, do more important things. This shows up in the form of mission statements, values statements etc. on websites. This is a bad idea for most people because it tends to foul up more pragmatic marketing, and also keeps your introspection terminally confused. School: Gig Supremacists

  10. Contrarian Smugness: Contrarian smugness is the posture that results from the idea that you’ve swallowed some sort of work-related red pill and abandoned some false consciousness that others are still laboring under. Something like “Lean Six Sigma is a lie, you should do the OODA Chi-Square Quality instead!” It’s usually just a beef elevated to an assumption that you’re on the moral high-ground. It combines resentment and missionary overcompensation into a kind of contrarian preachiness. School: Gig Supremacists, but with some spillover into Gonzo where the preachiness turns into messianic delusions.

So that’s it for my list of bad ideas. Bad by default, good by exception. What are yours? Do you know which school you lean towards? Do you fit into one of my 2×2 of 4 schools, or does the scheme not apply to you? How would you define your school?

Note: This newsletter will be shutting down on April 30th, 2021, and the archives published as an eBook.

To simplify the shut down, new subscriptions have now been turned off and existing subscriptions have been paused. Existing subscribers will still be able to access the paywalled archives until the list shuts down in May. The rest of you will have to wait for the ebook.

Posture Flow

Only 4 more newsletter issues to go before Art of Gig wraps up on April 30th!

Let’s try an exercise. Pick a three-word phrase to describe your current posture, the way you are present in your environment. One word for how you take in input, one for how you process it, and one for how you are pre-disposed to translate it into output.

Here is a table of cue words to choose from, but feel free to find your own. Try to stick to three words, but you can use phrases or compound words if you must.

For example, lately I feel I’ve been adopting a posture of blinkered, relaxed, invention. I’m not really paying much attention to the environment, I’m feeling pretty relaxed, and my output is mostly stuff I’m making up, rather than a response to the environment — ie invention.

If you find this exercise hard, here is an alternative way to approach it — in which of the many situations you routinely find yourself in these days, do you feel most naturally present? The situation need not be comfortable or pleasant, but you must feel naturally present in it.

Now pick the three words that describe that.

The reason I’ve been thinking about postures is that I think, on a day-to-day level, my entire approach being an indie consultant boils down to moving fluidly and naturally through a wider range of postures than I did as an employee.

It’s almost a mind-and-body expression of the “free” in “free agency.”

I can adapt to the situation, mood, and moment in a way that feels natural. I don’t have to ever adopt a stifling posture enforced on me by the situation that feels like it’s at odds with the one I instinctively want to adopt.

I don’t have to be “on,” I can just be.

This doesn’t mean all postures are pleasant. But a posture can definitely feel natural and unpleasant at the same time.

The phrase “comfortable in your own skin” is really what I’m getting at. Even if you’re uncomfortable in the situation, and find the feelings induced by it unpleasant or awkward, your posture is natural and allows you to be comfortable in your own skin. You own your presence in the situation.

This is a subtle thing. For example, if you are trying to learn golf and the swing feels awkward and unnatural, that’s not what I’m talking about.

In that situation, you’re still comfortable in your own skin because you’ve chosen the challenge of learning to swing a golf club, and are comfortable in your skin, even if you’re not comfortable with the mechanics of golf swings.

But if you have to pretend to enjoy golf when you don’t, because you’re in some sort of cartoon, old-fashioned business meeting on the golf course, and would rather be somewhere else, that’s an unnatural posture.

Free agency rarely feels like being in a straitjacket or otherwise forced into an unnatural posture, involving alien patterns of input, processing, and output that feel imposed. It rarely feels like your actions are a result of distortionary effects of the environment rather than choices you’ve made about how to be present.

By contrast, as an employee, I had s narrower range of postures available to me, and half the time, the posture I was forced to adopt by the situation didn’t feel like the natural one I’d adopt on my own. My postures felt somehow “edited.” They weren’t entirely my own. I couldn’t entirely trust them.

I remember in particular, the one time I had to actually wear a suit and tie. At that point, I hadn’t worn a suit in years, and had gained a bit of weight, so I was very uncomfortable in the one suit I owned.

The funny part? The event was an awards ceremony. I was getting an award.

One way to think of it is: a typical job involves having to put on a “game face” for work too much of the time. Only after decades, if you either find a very secure niche for yourself, or if you rise to the top, can you feel comfortable.

As a free agent, I don’t really have a “game face.” I just bring my regular face to every situation, and mostly my natural responses are also the appropriate ones. If I feel like I can’t bring the right posture to the situation, I reschedule the situation or get out of it.

A large part of feeling comfortable in your skin is letting your mind and body flow into whatever posture feels like a natural fit to the circumstances you’re in. This kind of comfort also tends to promote the fastest learning and growth, since you’re letting the unconscious intelligence of your mind and body lead, and trusting your intuitions.

A posture is really an unconscious mind-and-body decision-making formula that is simple enough to stick to even when your judgement is seriously compromised. Like when you’re drunk, sleep deprived, stressed, or temporarily depressed.

A natural posture is your chosen strategy in firmware form. It is efficient. It is compact.

Strategy in action is periods of confused action punctuated by posture resets (the firmware being flashed, if you like). Postures embody evolving strategies in periodically updated, compressed, formulaic ways. Your situation awareness and sense of current options get bundled with what your unconscious idea of what you think you’re doing, and show up in the stance you adopt in preparation for whatever is coming next.

In Boydian terms, postures are embodied orientations.

If you watch a martial arts contest (any form) you’ll notice that the action unfolds that way: bouts of confused sparring that may be more or less chaotic depending on the skill of the fighters, punctuated by posture resets. Sparring increases entropy. Posture resets periodically lower it again.

Strategy really is about the sequence of postures you reset to in the brief lulls between chaotic action. No plan survives first contact with the enemy or market. The fog of war descends and everything gets confused and mixed up. But things don’t stay that way continuously. You get brief periods of respite. Periods when you can do posture resets.

And the faster you can do those resets — “fast transients” in Boydian terms — the more generally effective you will be.

But if the environment imposes awkward and unnatural-feeling constraints on you so you can’t let your mind and body flow into the postures that feel natural, your evolving strategy gets heavily compromised.

Or put another way, it forces your thinking to be higher energy, and higher dimensional, increasing the chances of mistakes and failure. You have slower transients, and distorted orientations.

A posture is a pattern of potential wired to inputs and outputs. On the input end, posture determines how likely you are to notice particular changes in your environment. On the output end, it determines how quickly and how well you are likely to react to them.

Free agency allows you to flow much more naturally through postures appropriate to situations. Jobs, on the other hand, rarely do. You have to be “on” and aware of the difference between the posture you unconsciously want to adopt, and the posture the social/professional situation is forcing on you. You have to censor your natural reactions, and substitute unnatural ones. There is a significant cost to breaking from what’s expected of you.

In a way, your mind and body constitute a marketplace of micro-behaviors trying to sort themselves out in an emergent way, by flowing from one posture equilibrium to the next. Imposed situational factors can have stronger or weaker distortionary effects. So free agency is really a kind of “free as in markets.”

Free agency isn’t entirely an escape from posture-flow distortion, but it is a very significant loosening of the regulatory strait jackets imposed by typical jobs on typical people. That’s why we use phrases like “feeling trapped” or “feeling stifled” when describing the factors that lead to quitting jobs.

Your mind and body are being prevented from flowing through the natural postures they gravitate to as the environment changes. Things you’re learning and thinking and feeling aren’t being allowed to find expression in postures that encode your evolving unconscious intelligence at its best. Your orientations and transients are being continuously messed with, and it is too exhausting to resist. So you give up, and cede agency to the organization. You allow yourself to be “house broken.” You “stay in your lane.” It’s a relief to finally give up and just go with the flow. The energy draw drops.

The cost? You’re no longer learning and growing as fast as you could be.

Of course, there’s a chance you’ll find that perfect job where your natural posture flow exactly fits the demands of the role. But the chances are low.

Free agency is no guarantee of finding and staying in a fluid posture-environment-fit, but your chances are much better.

Note: This newsletter will be shutting down on April 30th, 2021, and the archives published as an eBook.

To simplify the shut down, new subscriptions have now been turned off and existing subscriptions have been paused. Existing subscribers will still be able to access the paywalled archives until the list shuts down in May. The rest of you will have to wait for the ebook.

The Art of Gig Ask-Me-Anything (AMA) Issue

Only 5 more newsletter issues to go before Art of Gig wraps up on April 30th!

This is the special AMA issue of the Art of Gig. Answers to 7 questions sent in by readers. They were all pretty challenging to field, but in different ways. It was a fun exercise, forcing me to really think about every aspect of the indie life, from subtleties hidden in mundane aspects, to in-your-face existential conundrums.

Here we go!

Q1. What framework(s) can I apply to convert money / hour to a scalable indie solution: money x product?

Traditionally, I feel like gig work and indie consulting can fall into a trap: At some point getting getting a higher pay rate takes more effort than just doing work at a lower rate. As a result, I’m trying to define strategies, pathways to transform the equation from mb+x=y (m = hours, b = rate, x = fixed price, y = payout) into a more scalable calculation, where payout is disconnected from hours. For example: [mb+x]*r = y (where -r- is reach). 

In summary: how do I best compound the work I’m doing so I create the same reward but with lower hours?Rafael Fernandez

Yes! This is definitely a trap. In fact, it is a vanity trap. The bill rate is the vanity metric for indies, but really has no necessary relationship to income or quality of life/work. Obviously, if you charge $1000/hour in theory, but only sell 1 hour a year, that’s much worse than charging $100 and selling a full available inventory of 2500 hours (approximately 52 weeks of 48 hours each). And if you burn up $10,000 in savings over 3 months to build a service/information product that brings in $1000/mo steadily with 1 hour/week maintenance, you’re making a nice, easy guaranteed $250/hour in steady state for low-marginal-effort work. We all do such calculations all the time. It is second nature to indies once you’re in the lifestyle for good.

But the issue is not modeling a money-making machine or flywheel in the cleverest way. It’s not even about reach (which just changes the slop and intercept in Rafael’s equation; it doesn’t actually decouple income from hours). The real issue is examining the assumptions underlying the design of the machine itself and drawing the right conclusions.

So how do you actually think about this? The thing is, it’s not a 2-dimensional problem (money, number of hours), but a 3-dimensional one (money, number of hours, and quality of hours). Most people forget about quality of hours, and solve the problem wrong in terms of just money and fungible time.

The 3 variables feed into 3 aspects of the problem that the machine solves:

  1. What you’re paid as validation of self-worth. Your rate anchors your self-esteem, and serves as a signal of the dignity of your kind of labor to others, to the extent you talk about it. This is a valid thing to care about. It only becomes a narcissistic vanity trap when it overwhelms other considerations. People in the art/design corner of the gig economy tend to be particularly insecure about this, and vulnerable to the vanity trap.

  2. How hard you want to work. This is about both quality and quantity, but people tend to reduce it to quantity because that’s the legible component of “hard.” Anywhere between zero hours (true passive income) to the Ferriss threshold (4 hours/week) to a nominal week (40 hours/week) to “passion level” (you love it so much you work to exhaustion continuously).

  3. The dynamics of your market. How much demand is there for what you offer, and what the options are for structuring it in various ways that lead to various amounts of work? For example, a recorded self-serve workshop and personal coaching sessions are both options for serving certain kinds of demand, with different implications for quality of time/quantity of time/money.

To answer your question directly, the best way to compound your work with the same (or increasing) reward is to not work as an indie consultant at all, but think like a product entrepreneur. If you build the right product, then obviously you get the highest compounding rate, and if you automate and outsource enough, you get a genuine decoupling and can retire early.

In this game, your time is almost entirely devoted to a front-loaded heavy lift towards developing the product (“labor cap-ex”) that can enjoy maximum compounding growth. The rest is marginal maintenance labor time (“labor op-ex”) for the nearly passive income.

But I suspect you don’t want to do that. If you did, you’d be building a tech startup, not an indie consulting business. Part of the fun of indie consulting is that you actually enjoy your work enough that you want to do a non-zero amount of it, and in a way that you have a sufficiently varied inbound stream of it.

In other words, you’ve decided to like work.

You don’t want to reduce it to a one-size-fits-all no-maintenance-needed product, make your fuck-you money, and retire to permanent leisure.

So my suggestion is: work backwards from two variables: how hard you want to work (hours per week), and how much variety you want in those hours.

That’s the tradeoff. And your preferred mix of variety and time may not be available given market structure. If you want to work 10 hours/week, with each hour being a fascinating and unique high-level 1:1 sparring conversation with an interesting person, that mix may simply not be possible. You may have to choose between 10 hours/week doing repetitive maintenance work on a passive-income product OR 20 hours/week doing 2x of the sparring work at half the rate.

But working backwards from hours*variety is a sensible way to drive the problem-solving.

Variety is actually a focused way of thinking about quality of hours for indies specifically.

If you can make all the money you want in 4 hours/week, that sounds great, right? But if those 4 hours are cleaning sewers, maybe that’s not what you want to do for even 4 minutes/week?

Most people would consider time spent talking to interesting people, calculating cunning moves in high-stakes games, working on challenging technical problems, serving the needs of people they genuinely like, or artistic/creative thinking, as “quality time.” Adrenaline, dopamine, oxytocin, endorphins… all the good stuff.

Most people would think of time spent filling out paperwork, fixing bugs in old Java code, cleaning sewers, or opening doors for people at a snobby hotel while wearing a ridiculous uniform very boring and low-quality. That’s just cortisol all the way.

The key to quality differs for different personality types, but for indies (or at least those who choose the indie life) it tends to lie in variety. Variety is the spice of our lives.

Indies tend to be open-to-experience, curious people for whom variety is the big driver of quality time. We don’t just want to work fewer hours and enjoy them, we want the enjoyment to be varied.

So if you solve backwards from number of hours and variety in work, you solve for quality and quantity of time. If that doesn’t meet your financial goals, you may have to work harder for a while to get the mix right. If the equation doesn’t balance at all with a reasonable range of indie work parameters (you could probably charge anywhere between $50 to $1000/hour in the United States, but if your equation requires you to charge $100,000/hour to balance, you’re in the wrong game — go start a unicorn company).

So in summary, decide to like work, think about quality of hours, and solve backwards from quality and quantity of time to what you must do to make the money you need. If you can’t solve the equation for the game you’re in, change the game to one with a different risk/return mechanism, like building a startup, or a paycheck job.

Q2. I’d be interested if there was every a moment in which you more or less decided to turn away from integrating into any normal sort of existence. I sense four years into my journey that I will attempt to integrate somewhat but deep down know we’ll always be hanging out at some sort of “fixed point” on the edge of these worlds.Paul Millerd

I don’t think I ever thought about it consciously, or had strong opinions about it, to be frank. I have very low need for “integrating” or “settling down” or otherwise acquiring the accouterments of normalcy. On the other hand, I don’t have a strong need to not have those things either. I am not particularly attracted to subversive or radical subcultures and “alternative” lifestyles for their own sake. I am neither actively conformist enough to want normalcy, nor cliquish enough to work harder to gain entree into a non-default alt scene so I can feel special and non-normie. And I definitely don’t think either crowd is superior or inferior to the other.

So the consequence of what is essentially social laziness for me has been — I basically do what I want based on my appetite for risk and reward at that particular time/situation in my life, and sometimes it looks normal to others, sometimes it looks weird. Sometimes subcultures adopt me as one of their own, and at other times they reject me as a normie.

Neither of those effects bothers me. The people I enjoy hanging out with and talking to tend to be indifferent to those things as well, and are a chaotic, changing mix of normies and non-normies.

I once tweeted that “normalcy is just the majority sect of magical thinking,” and I think that captures the essence of my philosophy. People think being “normal” comes with a lot of things that it actually has no relationship to, like security, happiness, convenience, low effort, good friends, community life.

Normalcy promises all of those things, but actually delivers reliably on none of them. To the extent you seriously want some very particular mix of those variables (I don’t; I’m happy with many mixes), and you solve for them relatively reasonably, you’ll end up with a solution that may or may not look “normal.”

It’s the same with being “alternative” in any way. Same kind of promise, same lack of delivery. Except that in the latter case, there’s a premium fee and brand appeal associated with chasing the vaporware.

Which means that normalcy and alternativism are things you have to value for their own sake.

Which is fine.

“Desired lifestyle” is an independent input variable into the optimization cost function, with its own weight. It’s not the dependent variable that comes out the other end.

As far as I am concerned, there is zero difference between wanting “normalcy” versus wanting a particular kind of “alternative” life like being in a biker gang, an emo music scene, or a global nomad-worker scene. “Normal” is just a lifestyle narrative aesthetic that has majority appeal. Alternatives are just ones that have a minority appeal. Different narratives come with different aesthetic features and price tags.

So another way of summarizing my answer is — I put a very low weight on the narrative aesthetics of my lifestyle. So long as it makes sense and works for me, and I’m able to keep the friends I want to keep, I don’t need it to look good. Either to me or to others. As it evolves over time, it might look more or less similar to more consciously crafted narrative aesthetics by accident, but there’s no real design input on my end.

Any resemblance to any Branded Narrative Lifestyles™ living or dead, is purely coincidental. No identification with actual subcultures is intended or should be inferred.

But again, it is a valid thing to weight more or less. If you want to give it a huge weight, that’s fine too. That’s what strongly involved subcultural types, where the lifestyle narrative aesthetic borders on a LARP, do.

Q3: What is your suggestion for managing and writing about ideas that can span years and decades on one’s blog? Do you print your older posts and review them? Do you edit older blog posts and essays when you find mistakes or ideas that need clarification? How about your process for turning series into books. Do you ever outsource that? Do you have an editor?Ryan Nagy

[Preamble: This question might seem off-topic, but I decided to answer it because is actually a good and important question for all indies. Writing and publishing are now basically a cost of doing business as an indie in most cases. So it is a very good idea to not just take it seriously, but learn to enjoy it.]

I basically almost never go back and read my older writing, though I reference it a lot through back-linking, based on what I remember saying. I only go back to read if I want to reference it, but can’t remember what I actually said. I almost never edit old posts or fix bugs. If the topic is evergreen enough, and I am interested enough, I might do a new bit of writing as a sequel, but I don’t think editing/updating/maintenance is fun enough for me to do much of it.

I don’t have a systematic process for ebooks, but yes I do outsource it. I’ve worked with 4 different partners for 10 ebooks. I’ve had copyediting done on some, others I’ve copyedited myself, and others, I’ve pretty much just put out as-is. My minimum standard is the Amazon Kindle store flagging typos and threatening to unpublish my books if I don’t fix them :). The whole area is unfortunately still pretty janky, requiring significant human TLC to produce even a low-production-quality ebook.

This is honestly in uncanny valley of effort for me. Neither my online archives, nor my ebooks, are a big enough source of either identity or income to optimize to death. But neither is it a trivial enough source of either to entirely ignore.

I think production effort for writing, in any medium (blogs, newsletters, books) should be in proportion to:

  1. Identity salience: Creative work is part of your extended identity, so simply caring about how it looks is a legitimate thing, and people have different minimal standards. My minimum for basically everything, if I can get away with it, is “shitpost,” while others want even their most trivial thoughts to be carefully refined and quality-controlled, and beautifully packaged and presented.

  2. Real risks: you don’t want to make mistakes if your article or book is teaching people how to do brain surgery or fix nuclear reactors. I don’t write about anything that risky. But if I did, I’d care a lot more.

  3. Ambitions: if you want to hit the New York Times bestseller list, you need to do a certain level of production. I don’t.

  4. Marginal upside: Will another round of spit-and-polish garner 10x more page-views or 10x more sales of ebooks? Or are we talking 10%? Or 1%? In my case, the answer is usually 10%, not 10x. Not worth it. Not not worth it either. My laziness breaks the tie and I usually decide it’s not worth it.

  5. Marginal downside: Will another round of spit-and-polish prevent disastrous reputational impact and social death because you have a tendency to make non-PC jokes that might get you canceled? Or will it merely lose you a couple of OCD grammar bureaucrats who care too much about you’re commas and apostrophe’s? In my case, the downside is limited because I don’t have radical, heretical thoughts burning a hole in brain, trying to sneak out and burn everything down. I’ve not really had to watch what I say to stay safe.

And as for managing writing over the long term for internal reasons, working effectively on a large body of evolving, interconnected thought — I actually think it is best not to manage it at all. Anarchy is my ideal. If something is important enough, you’ll remember it, and it will turn into a through line in your work organically. If you forget it, it wasn’t important. If a connection between two ideas is salient, it will keep crossing your radar until it forms a synapse in your head. If not, the connection doesn’t need making.

This probably sounds more like rationalization of laziness than it is. I’m not that unconcerned. I genuinely think active management of long-term habits of thought does more harm than good most of the time. Let your mind find its natural cowpaths, then pave them.

That said, it is helpful to nudge the process along by using a decent system of backend notes (what Tiago Forte calls a “second brain” — he’s writing a book about it that features in Q5) to store more raw material (including raw material generated by long-ago you) than your first brain can hold, and make sure it churns in and out of your attention in a sufficiently rich way.

I’ve used a variety of media for that over the years, but it’s generally been too chaotic to call a “system.” My current secondary medium is Roam Research, which I highly recommend. But my primary medium is actually my public blog, Ribbonfarm, which is more of an over-produced private notebook than the under-produced publication it pretends to be.

But beyond capture and storage, the rest is basically optional. Create a sandbox, then let your mind play in it.

Q4: What’s the best way to learn more about People School of thought? Steven Ritchie

For those who are wondering what this question is about, there are two major schools of management consulting, the majority Positioning school, represented by (for eg) Harvard Business Review, McKinsey, and Michael Porter, and the minority People school, represented by a more rag-tag bunch of academics and practicing boutique and indie consultants. The basic background on this important distinction is in the book Lords of Strategy by Walter Kiechel, which I reviewed here.

I wrote an early Art of Gig issue about this (A Tale of Two Schools, May 29, 2019) which I just un-paywalled for this AMA issue. The tldr of that post is — there has been a war brewing between the two schools. Both school represent opposed Great Truths, so whatever directions your sympathies lie, you should be prepared to make your own yin-yang synthesis and ride out the war. My own prediction is that the People school will slowly gain ground, and a new equilibrium will be established that is 80-20 in favor of the People school side, as opposed to the current 20-80 against.

The People vs. Positioning battle is one front in a bigger trend that goes beyond the indie/gig economy, the rise of what I call 5th generation management. I did an issue of my Breaking Smart newsletter on that.

With that background out of the way: how can you learn more about the People school (a very good objective — learn more about the likely winning team)?

Besides reading some of the material I’ve linked to and following the trails from there, the most important thing you can do is to literally focus your learning on people!

The Positioning school is rooted in economics, the People school is rooted in sociology and psychology. So basically, anything that improves your instincts and intuitions on the latter helps. Whether it is TV/movies, literary novels, or the psychology of game design (as opposed to economics-style game theory), it all helps. And there’s of course plenty of explicit management literature from the People school (see Kiechel’s book for a host of starter references; my favorite sub-school within the People school is of course the Boydian OODA loop/maneuver warfare body of literature, which is also the mainstay of my own consulting practice).

This does not mean you should ignore the Positioning school, but your learning about it should be driven and framed by your overall People-school mental models. Ideas from the Positioning school make for good servants, but poor masters.

But above all, to increase your rate of People school learning — spend more time with actual people! As many different kinds as you can. Talk to them, be interested in them, understand their various nerdy obsessions, sit in on their meetings even if you don’t understand half of what they’re talking about, visit diverse organizations (in person or on Zoom), and so on. Devote most of your time to that end of things as opposed to reading the Wall Street Journal/HBR/Financial Times or building spreadsheet models based on balance sheets and annual reports or abstract reified analysis models like Porter’s 5-forces or “Value Chains.” Those things are important, but should be kept subservient to your People thinking.

That’s all there is to it. The People school is basically just being interested in actual people rather than the numbers that model them in economists’ models.

Q5: I’m approaching the completion of… the Building a Second Brain book. Manuscript is due in 3.5 months, it’s about 65% done, and now has a clear shape and identity. I’ll spend the next year and the first year after launch promoting it, and then sales will hopefully continue over the following years. It feels like the culmination of 5 years of my career, but really the last 10 years of my life.

I usually have a good sense of what’s coming in the future, and I look forward to it. But I’m having difficulty seeing past the event horizon of this big milestone in my life. I can’t imagine doing anything as important, impactful, or challenging, so every future past the next few years I imagine feels like decline and stagnation. I guess this is what they call a mid-life crisis!

What’s your advice for indies who are on the verge of reaching their fixed point ? Which for me has been to get this book published at all costs. What is meaningful to reach for once the biggest goal is realized?Tiago Forte

For background, Tiago is referring to the idea of planning your future around arbitrary, idiosyncratic, highly personal “fixed points” such as home ownership or other personally meaningful goals, such as creative projects (in Tiago’s case, the book he’s writing, or in my case, wanting to pursue amateur astronomy more seriously in coming decades).

I explained (and recommended) the fixed points approach in last week’s issue as an alternative to more analytical approaches trying to “optimize” your lifestyle design with spreadsheets to maximize money or minimize hours, which I consider a depressing and nihilistic approach.

So, the answer to Tiago’s question…

“having difficulty seeing past the event horizon of this big milestone in my life” is the biggest feature of fixed-point thinking, not a bug!!!!! There’s nothing to fix here!

The whole point of thinking in terms of fixed points is that they give you a finite horizon that is not a means to some further end that lies beyond! It’s a way of solving the infinite regress problem. The fixed point in your life plan is an end in itself, and to the extent it is a meaningful end, it should create a blindness to what lies beyond! A good fixed point should feel a bit like a death wish; a horizon of self-annihilation! It should cause life-and-death levels of stress as you approach the big moment.

Why?

Because meaningful goals utterly transform you. You will come out the other end an entirely different, reborn person, working with a clean canvas on a resurrected life design. I felt exactly as Tiago does while I was finishing my PhD in 2003, and felt it so strongly that the feeling showed up as a set of quotes with which I opened my thesis. Here is a photograph (this is the first time I’ve cracked open my thesis in a decade I think)!

“How could you wish to become new unless you had first become ashes!”

Indeed. Quite so. Couldn’t have said it better myself Friedrich!

A good metaphor for keeping this in mind is that of a compass pointing to “True North.” What happens if you actually reach the magnetic north pole? The compass needle starts spinning uselessly! Every direction is (magnetic) “South” so the dipole has no way to align to a particular direction. It’s like a division-by-zero error. A singularity. A self-annihilation.

And this is a good thing. Now you’re free to pick a new direction, a new fixed point.

The problem would be if you didn’t have the blindness past the event horizon. Then I would doubt whether you had in fact discovered a meaningful fixed point in your future. If you can see past it, it’s a means, not an end.

So tldr — Tiago — you’re needlessly worrying about what is in fact the strongest proof that you’re working on a highly meaningful fixed point future that will transform who you are. Like Gandalf the Grey became Gandalf the White after his death-and-resurrection battle with the Balrog.

See you on the other side as Tiago 2.0! Burn Tiago 1.0 to ashes!

Q6: With the creator stuff, I imagine you could charge $10 for art of gig and likely not impact signups.  How do you think about pricing and how much you make.  I get the sense that you could push 15% harder and easily make more but that you have some deeper principle that knows this is ultimately not worth it.Paul Millerd

Pricing is a complex, technical, and subtle topic when you are working on the corporate version of it. I just came out of a client meeting where we were discussing the nuances for their business — computer hardware. It gave me an actual headache, juggling the complexity of the model’s parameters in my head. It’s hard stuff, but I’d say most indies with some math training are capable of grappling with even the toughest versions of it, given some aspirin and domain knowledge.

But pricing for indies is only complex if you want it to be. If you recognize one central fact — that what you are selling is a piece of yourself — it becomes very easy indeed. No math needed.

In my case, pricing is primarily a proxy for the kind of formal or informal contract I am entering into. A $5/month newsletter sends different signals and sets different expectations than a $10/month. Since $5/mo is the minimum Substack allows, pricing at that point sends a very simple message — I want to make money, but do so while making the writing as humanly affordable as possible, so the maximum number of interested people can access it, short of it being actually free. Any number above that sends different kinds of signals about what I think my thoughts are worth, what I think it should be compared to, who I think my audience is, and what my calculations are about the revenue-maximizing point (whether or not they are correct).

The same kind of logic applies to pricing my consulting services. Currently I charge $450/hour (I started at $150 for my first gig, and I revise it every couple of years, but it’s been stable at this point for 3-4 years). It is probably not the revenue maximizing point (I could make more overall if I charged somewhat less and said yes to everything; my current yes rate is probably 50%). Neither is it the most I could charge that the market would bear. That limit is probably $1000/hour right now. Above that I’d be hard-pressed to sell any of my time.

For me, my current rate is the rate that sets the expectations I’m willing to let myself be bound to. Less, and I’d get too much inbound, and more importantly the wrong kind of inbound — stuff like life coaching or early-career advising that I have no interest in or talent for. I’m primarily a resource for experienced people. More, and I’d feel under more obligation/pressure to “create value” than I want to subject myself to. If I accidentally create more value than I am charging for, I’m happy to let others have the surplus. Nobody ever leaves money on the table. Other people take it. And if you like them enough, it’s okay.

So yes, I do have a “deeper principle,” though I don’t know how “deep” it actually is. It’s the same principle as the one I used in answering Rafael’s question earlier in this AMA — solve for quantity and quality of work, and begin by deciding to like working.

Most people who land on the “maximize income” trajectory (money solvers) or “maximize bill rate” (vanity solvers) do so by unconsciously starting from the opposite commitment to themselves: they have decided to not like working. They are working for fuck-you money (or what is almost the same thing, fuck-you fame) same as boring careerists and second-rate entrepreneurs solving for an “exit” rather than the next level of their mission. Working to stop working. A finite game.

Me, I work to continue working. Infinite games ftw. Not very hard, admittedly, but I don’t solve for stopping.

Once you decide to like work, and solve for both quality and quantity to make it sustainable indefinitely, it becomes obvious that solving for maximum revenue OR for maximum “status” as indicated by bill rate, is a very dumb thing to do.

And while marginal effort/value calculations are good to do, I don’t think the value side of that calculation should be measured in terms of money, because the cost side is being measured in terms of who you are, and what you are becoming by selling little bits of yourself at $X/hour.

Ie, “15% more work” gets me… 3x more something, and that something should be the kind of trajectory of being/becoming that feels most enriching to you, once you satisfy baseline economic/lifestyle needs.

This is a more convoluted way of saying, “solve for return on personal growth.”

So the formula is:

  1. Decide to like working, and to continue doing so indefinitely

  2. Figure out the quantity/quality mix of work that will allow that

  3. Optimize marginal effort equations for personal growth, not money

It’s really not that hard once you’re past the bare subsistence level of the struggle (which of course I have deep sympathy for; having been there, and having a non-trivial chance of being there again).

For what it’s worth, I think you (Paul) are doing exactly that, based on your writings, so you already follow some sort of equivalent principle.

Q7: You’ve been pretty open on twitter about the emotional toll of Covid – Are you still reading the plague as a major bell-bottom bummer? How would you describe your approach to this dysthymia? Is it the adoption of new fixed points, or is there anything else you’re doing to get re-enchanted?Paul Sas

Well, I do play a certain campy character on Twitter, which is some sort of grumpy-emo-uncle, but there’s some truth to that persona beneath the theatrics. For example, throughout the last year, I’ve been using the “Tonight at 11… DOOM!” Futurama gif a lot. That’s… mostly theater. It’s not like every time I posted that gif I was actually feeling overwhelming doom. I was on my couch tweeting, not working in an ER or trying desperately to log on to the unemployment website.

But OTOH, I’d say my overall reaction to Covid, modulo campy Twitter theater performance, has been pretty WYSIWYG. When I’ve sounded upset over the last year, I generally have been at least a little upset.

My approach to this dysthymia is to give myself permission to actually experience it as completely as I can. Unlike personal depressive episodes, Covid is genuinely a once-a-century systemic shock. The dysthymia is collective. A deeply shared experience. You’ll likely never be more connected to the rest of humanity at large as you are through this pandemic. There’s never been a sharper, stronger reminder of the connectedness of our fates and the importance of choosing compassion and pro-social attitudes to life. It’s weird to not allow yourself to experience it and make meaning out of it. Going by the historical record of the Spanish Flu and the Black Death, this dysthymia is going to turn into a sort of irrational collective euphoria and exuberance once the danger is behind us, but the shock and damage will continue to unfold. Changes will still be needed and will happen, even as depression inevitably turns to hypomania.

My approach has been the same for all of what I’ve called the Great Weirding of 2015-20, but I’ve held to it particularly through Covid. I don’t believe in beating an analgesic retreat, or what I call “waldenponding.” That doesn’t mean I don’t believe in self-care or emotional self-regulation. Those are important things. I just try to do them without retreating from the reality of the situation, because that makes second-order responses harder and worse.

While I do believe in emotional self-regulation, the style of such regulation I am fond of is more towards the gonzo side than the stoic side. I don’t place a particularly high value on inhabiting a narrow emotional range with an average position at Aurelian equanimity maintained with might striving. In fact, I believe that’s a kind of undeclared retreat. It is emotional self-regulation turning into emotional self-repression.

Interestingly, as a natural low-reactor without a huge emotional range, either internal or expressive (typical INTP in short), even campy theatrical emotional responses don’t come very naturally to me. Emoting is something of a learned skill for me. It’s of course easier on Twitter, where it’s all emojis and text and gifs, but I wouldn’t be able to pull off that kind of gonzo cringe-clown act in person.

Of course, seeking new fixed points and re-enchantment in a post-Covid world are important second-order responses, but the only way those will have a generative depth to them is if your first-order approach to experiencing what we’re going through is highly present. The more your first-order response is retreat and denial, the more your second-order responses will be some sort of fearful, overall reactionary retreat. There’s a reason most approaches to re-enchantment have a reactionary or anarcho-primitivist flavor. The challenge isn’t to find new modes of post-Covid meaning-making. Any idiot can find a retreat LARP that fits. The challenge is to have those modes be future-positive, optimistic, curious, compassionate, and still interested and involved in the grander human story.

In a way, an article of faith for me is that the courage to be present in the moment when things are difficult actually lessens the total amount of courage you’ll need to get through the rest of your life, including the delayed effects of tough times. I an actually much less courageous than most people. I just tend to think in terms of the NPV of courage needed through all of life, not just the courage called for in the moment.

If your response to Covid has been to retreat from social media and move to a farm where you live a primitive, fearful life, in my book, you’ve kinda failed to rise to the challenge of this historical moment. You’ve given up on true re-enchantment and settled for a fearful nostalgia instead.

Equally, if you yield to the collective euphoria that’s coming by diving in and partying like crazy, that’s actually just the flip side of waldenponding. It would be equally a failure.

So yes, I do think the “plague is a major bell-bottom bummer” (I’ve never heard that phrase, but it’s a good one), but I’m pretty happy with how I am responding to it, both practically and in terms of managing my psyche through it. I’ve gonzoed my way through it and will continue to do so.

~~~~~

So that’s it for this special AMA edition of the Art of Gig. 5 more issues to go before we wrap!

Note: If you are forwarded this newsletter, please be aware that it will be shutting down on April 30th, 2021, and the archives published as an eBook. So if you’re interested in subscribing, I recommend waiting for the eBook instead. If you do subscribe, please use the monthly option, not the annual one, to save me trouble wrangling the refunds.

Personal Futurism for Indies

Only 6 more newsletter issues to go before Art of Gig wraps up on April 30th!

A couple of weeks ago I said one of the remaining issues of this newsletter will be devoted to an AMA (Ask Me Anything).

The AMA issue will be next week’s issue (March 25), so if you are interested, reply to this email with your question by Monday, March 22nd. If you want to remain anonymous, please specify that.

Keep your question short and focused so I can address as many as possible within whatever word limit budget I impose. It can be about anything, ranging from big macro trends to personal situations/tactical challenges you’re personally facing in your gig career.

This is the last call at the Art of Gig bar 🍺🥃🍸🍹🍷🥤😎

By way of a prequel, this week, I’ll tackle one of the questions already sent in, by Benjamin Taylor, since it is a nice, broad one, for which I have a longish answer (for the AMA, I’ll be prioritizing questions where I can think of short answers that make me sound clever).

What do you think is the future of indie consulting? Are new patterns emerging?

I don’t think there is such a thing as the future of indie consulting. In a way the whole point of indie consulting is to break free of the company-sized shared futures that bind paycheck employees (that’s the “indie” in indie consulting).

So the real question is, how do you figure out a future for yourself under this umbrella concept of indie consulting? That’s the personal futurism question.

I’m going to attempt an annoying teach-people-to-fish answer, ie lay out how I think indies should tackle the challenge of personal futurism.

As my use of the qualifier personal indicates, we generally assume futurism is for institutions, not individuals. Think tanks conduct futures exercises for countries, corporations, and militaries. Individuals make plans for the future, but don’t generally conduct personal futures exercises.

There is a good reason for that.

Most individuals are employees. For employees, personal futurism gets radically simplified to the future of a specific employer or a set of adjacent employers you might easily move to. So you just have to make plans. The futures pre-work is already done by the context. In fact one of the attractions of working a paycheck job (or joining a religion, or signing up for the military) is that you can outsource futures thinking to a leader. Your own futures decision gets reduced to — does my future lie with this leader or elsewhere?

For indies on the other hand, the future is wide open, and subject to invention, not just choice. As open and subject to invention as it is for institutions.

When I do futurism, I tend to do so obliquely, via design fictions or scenarios. I’ve used both in recent issues of Art of Gig:

  • Design fictions: In my issue last week (March 11), I used the device of excerpts from future books to lay out some broad scenarios.

  • Scenarios: In my Feb 25 issue, I laid out 4 scenario stories — A New Technocracy, A New Socialist Hope, More Neoliberal Than Thou, and The Empire Strikes Back that help me think about the future as backdrops.

The thing is, neither of these is a prediction/forecast mechanism per se. Design fictions and scenarios only give you an approach to testing your plans, without providing you with a way to actually make plans. They’re like wind tunnels in which you can test airplane designs. But you still have to come up with designs to test.

But you can get to plans from these oblique testing mechanisms via a sort of chicken-and-egg iteration I call test-driven futurism.

Test-Driven Futurism

Suppose you make two shitpost-level starter plans like so:

Plan A: I’ll quit my job now, move to SE Asia and learn Chinese and build an indie consulting career out of China expertise, living on savings in the meantime.

Plan B: I’ll teach myself PyTorch and learn about the retail industry, so when AI in retail takes off in a couple of years, I’ll be able to quit my job and walk into a lot of gigs.

You can test both plans against the four scenarios above, and conclude that (for example), Plan A would work best under More Neoliberal Than Thou, and worst under The Empire Strikes Back, and then based on the relative likelihoods of the four scenarios, you could compute a weighted probability of the plan working well. You could do something similar with the design fictions, which are really implicit scenarios. Then you’d do the same thing with Plan B and compare the results.

As a side-effect, you can also compute the relative attractiveness of different futures across the plans you are considering, which gives you a sense of the future you should be rooting for and trying to make happen. Obviously you should root for, and work towards, futures that play best to the strengths that inspired your plans.

This can lead to surprising conclusions. For example, if you are skilled at crisis management and fire-fighting, and make plans that reflect those strengths, you might find that the most attractive future for you is one that is in constant crisis!

You might feel like an asshole for rooting for such a future, and repress your natural futurism instincts, or rationalize what you’re doing, but there’s no denying your strengths.

In a weird way, the pandemic is almost a dream scenario for epidemiologists (so long as they have protective equipment). And seismologists get to shine when earthquakes happen (so long as they are far from the epicenters). If I were either, while I wouldn’t wish for big pandemics or earthquakes, I’d probably secretly want enough small, contained epidemic/earthquake incidents so people are concerned enough to invest in preparedness — and hire me to help. This is even a trope in some thrillers — the mad scientist who triggers a small crisis because people refuse to listen to their warnings about the Big One.

And back in the real world, arguably the Culture War exists because 15 years ago, a lot of unemployed young people got very good at culture-warring on online forums, and decided to make indie careers out of that strength. Had they been a bit more self-aware about the interplay of personal strengths and preferred futures, maybe they wouldn’t have invented this dark, Gawkerized future for the rest of us. Maybe they’d have found a way to use their powers for good instead.

Anyhow, back to the test-driven futurism process.

Once you’ve ranked various plans (by preference and likelihood of success) and made opening moves on one that seems robustly set up for success in the most likely futures, you can then refine it. And along the way, you can work to make those futures more likely, using the chicken-egg process of planning-and-futures-thinking as an engine of self-fulfilling prophecy.

This is easy to reduce to a spreadsheet exercise. Therein lies a problem…

Death by Spreadsheet

Even if you are okay with test-driven futurism leading you to root for (and work towards) dark futures that play to your strengths, there’s actually still a problem, an amoral one.

I think exercises like spreadsheet futurism are important, but they leave the question of how to make plans in the first place unanswered, especially imaginative plans with an element of invention to them. I mean, isn’t that why you went indie or are contemplating doing so? To invent or reinvent yourself? Do you really think you’re going to get there by matrixing out plans and scenarios on spreadsheets?

There is a chicken-and-egg problem running on empty here. You speculate to create background scenarios to work with, then make plans inspired by them in illegible ways, and then try to test them against refined versions of the original scenario, which leads to refined plans, which leads to further refined scenarios, and so on ad infinitum.

You do that and you hopefully bootstrap a probabilistically future-proof plan out of a shitpost-level initial casual thought.

In all likelihood, if you do this, you’ll converge on slightly dull, imitative scripts that are just as confining as the ones you left behind/plan to leave behind.

In my experience, by itself, test-driven futurism is a dispiriting, demotivating, and tiresome exercise. It is death by spreadsheet. A distant cousin of death by powerpoint. All you need to kill yourself that way is more rationality than sense.

Test-driven futurism leaves you with a general sense of the overwhelming complexity of the future and the dozens of ways it can and will prove you wrong, even in the “known unknowns” department, and an uninspired plan with which to meet it. And we haven’t even talked about unknown unknowns/black swans. The only way to future-proof your life is to act dead to greater or lesser extent. Test-driven futurism is futurism within the iron cage of spreadsheets.

That’s the reason it is primarily risk-averse bureaucratic organizations that approach futures this way. It does work to bootstrap plans, but the plans that emerge tend to be uninspired and conservative, like a hedged portfolio constructed by a doomsday prepper with a lot of money. A case of risk-management procedural skill overwhelming imagination and openness to experience.

You don’t even have to go through the exercise to land on the “answer” it is rigged to produce when pushed to the limit of absurdity with enough money in play — save enough to build a bunker in Wyoming or New Zealand, and pack it with guns and supplies.

You’re not going to end up doing interesting, noteworthy things with your future if you limit yourself to this kind of test-driven futurism. It is a fundamentally nihilistic way to approach the future. The more you have to lose, the more apocalyptic the futures you will imagine.

How do you look at the future in a way that might make you can a differentiated part of a living, growing, thriving condition? How do you avoid becoming a bunker-secured survivalist in an apocalyptic future predicted by your spreadsheet, and which you help turn into a self-fulfilling prophecy?

How do you avoid death by spreadsheet?

How can you become one of those who, in some small way, helps invent the surprising, serendipitous future rather than predict the doom-and-gloom one?

A different, complementary approach to futurism helps you approach planning from that angle. I call it fixed-point futurism.

Fixed-Point Futurism

Fixed-point futurism is related to the idea of inventing the future rather than predicting it.

You’ve probably heard the Alan Kay line that it is easier to invent the future than it is to predict it. The line is generally invoked in relation to huge inventions, like semiconductors, or the personal computer (which Kay had a hand in) that “invent” the future for everybody.

Much as I like that sort of thing, and though indies generally are pretty creative and talented, I definitely don’t expect 99.9% of you to participate in such revolutionary acts of invention. I’ll be really happy for the 0.1% of you who do end up being part of such big inventions. When you do, I hope you’ll remember the rest of us and toss us some juicy gigs.

For the remaining 99.9%, how do you apply the invent-the-future idea at a more modest, personal scale?

It’s simple: don’t make plans, choose fixed points.

Choose one thing to make true, force to be true, about the future. Something that is likely to be within your control, no matter how the future plays out. Something that isn’t rationally derived from something else more basic, but is sort of arbitrary and self-defining. The more nonsensical the better. The fix for the default disease of having more rationality than sense is to aim at more nonsense than sense.

It could be as simple as “I’ll only wear blue shirts from now on.” Now that’s something you have a good chance of making true whether the future is a zombie apocalypse or fusion-powered starships.

Whatever the future, you’ll be wearing a blue shirt in it, dammit! That will show the universe who’s in charge!

It sounds silly, but it’s really amazing how such small acts of assertion of personal agency, far short of putting a “dent in the universe,” can magically make life feel more meaningful. You’re arbitrarily using your life to declare that futures where you wear blue shirts are better than ones in which you don’t.

Many people intuitively do fixed-point futurism. In fact, in the US, the so-called “American Dream” has historically been based on the standard fixed point of home-ownership. As in, “no matter what happens in the future, I’ll be a homeowner.”

A way to understand fixed-point futurism is to think of it as a priceless commitment. No matter what happens, and no matter what else goes wrong or off-the-rails in weird ways, you’ll make sure one thing goes really, really right, even if you have to go crazy making sure it does. In other words, you’re committing future agency and surplus resources unconditionally to the defense of your fixed point. You can’t predict the future, but you know what you’ll value as “priceless” within it.

The nice thing about fixed-point futurism is that you don’t have to worry about tradeoffs. You don’t have to constantly revisit cost-benefit analyses. You don’t have to worry about competing priorities.

The fixed point is priceless, so you can commit to it without knowing lots of important things about the future. For example, if your fixed point is home ownership, then you have no idea what interest rates will be, or how you’ll make the mortgage payment in March 2032, but you know that psychologically you’re invested enough in the idea of being a home-owner that you’ll do what it takes, and sacrifice other things as necessary. Home ownership is the standard by which you have chosen to measure the value of everything else in your personal future. In your personal futurism exercise, all roads lead to home ownership. If you find yourself googling rent-vs-own calculators, you aren’t truly committed to home ownership as a fixed-point. You’re committed to maximizing money, which is another way of saying you have no fixed points. Money has become the measure of your life, because there’s nothing you measure the value of money with.

Your chosen fixed point is basically a proxy for your identity. To contemplate giving up the fixed point is to contemplate changing who you are at a deep level. Those are the stakes of fixed points. It’s not that you’re not willing to change at a deep level, even a death-and-resurrection rebirth level. It’s about what stakes represent the existential cost of that depth of personal change (there’s an old Simpsons episode where Homer has an existential crisis over looking for a replacement pair of blue pants).

So your choice of fixed point is an indirect expression of your identity attachments, in particular the priceless parts. This is why the fixed points people intuitively pick are typically the obvious identity-linked ones in a given culture:

  1. Providing for family

  2. Participation in religion

  3. Building a home

  4. Car/vehicle

  5. An element of lifestyle like camping or surfing

  6. Community service

Here’s the thing though, it doesn’t have to be limited to these obvious ones. In fact, unless you are super pessimistic and lacking in confidence about your own ability to do more with your life than merely survive, you probably will have life energy to do more than “provide for family,” no matter what happens in the future. Your fixed-point future is what you solve for assuming you have a surplus beyond what it might take to meet these basics. Your passion mission, as I called it in an issue about a year ago, but generalized to life beyond gigs.

Here’s an unusual one from my own planning. For the last few years, the question of where I might want to settle for good, after 25 years of nomadism, has seemed too complex to tackle. There are too many variables, and the test-driven futurism approach drags me down gloomy, dispiriting, risk-focused bunnytrails like figuring out places most resistant to climate change, a crashing dollar, and earthquakes.

Do I really want to plan my 60s and 70s around fearfully cowering in the safest place I can think of, with potential disasters front and center?

But then, getting back into amateur astronomy last year during the pandemic suddenly made me realize that is a potential simplifying fixed point in my personal futurism. I’d like a future involving a nice big telescope in a place with really good visibility. Miraculously that dissolves a lot of complexity, and changes even the risk perceptions. Like for example, suddenly earthquake risks loom less, and the risks of failing eyesight increase… but there’s a solution to that as well! I could get into amateur radio astronomy, with headphones instead of eyepieces! Might the dollar crash creating a Mad Max world? Well, I should learn to build my own telescopes from junkyard parts in a Mad Max world!

Fixed point futures are strange attractors. Everything else starts revolving around them once you truly commit to them. You’ll know because from rational, spreadsheet perspectives, nonsense will start pulling ahead of sense. Which is a good thing. A decade ago, my motto was Be Slightly Evil. Now it is closer to Be Slightly Nonsensical.

Astronomy is also something of a “priceless” interest for me. While it is not literally priceless, I don’t make decisions about indulging the interest based on cost/benefit utility calculations. But if I commit to it as a proper fixed, point, I will be making decisions about other things based on their friendliness to an astronomy-centric later life. And there will be nothing rational about that. To compare — ten years ago when I went indie, I was choosing where to live based on the very rational criteria of which cities had good airports and a decent flow of techie types traveling through them.

This is a very silly example, but it demonstrates how fixed-point futurism works. By introducing an arbitrary, almost nonsensical stable element in your futures thinking, one that is outside of the calculus of ordinary utility computations and rational expectations, it gives you a simplifying lens with which to view the future. It provides something like a Schelling point for all futures to converge towards, for you personally.

The world may be going to hell with zombies crawling all over the place, but dammit, you’ll be there in your blue shirt, chopping off the heads of the zombies attacking your precious telescope.

The world may be melting down with climate change, but damn it, you’ll be building telescopes that can peer through weird weather patterns. In your blue shirt. While chopping off zombie heads.

Now that’s a hill worth dying on.

The problem with the zombie apocalypse was never that zombies might kill you. Something is going to kill you eventually in any future, and zombies aren’t actually much worse than Covid, car crashes, climate change, or cancer. The question is, what hill is worth dying on, in all futures?

In my December 10th issue, I wrote about how you should not build a hill to die on, when it comes to your indie career. Well, this is how you should build one: In the most nonsensical way you can get away with, unmoored from rational considerations, but capable of shaping those rational considerations.

When one person does something like this, it is merely eccentricity. When large segments of the population start doing things like this, you can get a weirdly miraculous-seeming flourishing of entire cultures. There’s a reason why Victorian Britain was simultaneously the leading superpower of its time and a hotbed of weird eccentrics doing their own thing, creating their own personal futures.

I mean, it is exciting that we live in a time where Elon Musk is trying to invent a future where thousands might be able to travel to Mars. But I think the possibilities of a world where thousands of eccentrics are planning around weird fixed-point futures is even more exciting. And there’s no reason why both can’t come about.

Pursuing fixed-point futurism is the temporal multiverse equivalent of the Archimedes principle of the lever: “give me a place to stand and I will move the earth.”

Give me a fixed point to plan around, and I’ll move the multiverse. It may not be for a big, lofty ambition, but you don’t need lofty ambitions for personal futurism.

You can be like Rick Sanchez on Rick and Morty moving the multiverse to get at the Mulan McNugget sauce.

I usually have several candidate fixed-point ideas floating around in my head at any given time, with varying degrees of commitment attached. Right now, they include: astronomy, a “mansion” (code for something I’m not quite clear on myself yet), a Mars rover, and an idea for a fictional extended universe I want to develop. There’s a lot of the best kind of nonsense driving me right now.

To bring this riff back to earth, of course practicality is important in futures thinking. But if practicality is all that goes into your thinking about the future, it will be a very dull future you script for yourself. And it will be your own fault. Why would you expect to get interesting things out if you don’t put interesting things in?

In practice, fixed-point futurism and test-driven futurism work well together as complements. One is rational and left-brain dominant, the other is emotional and intuitive, and right-brain dominant.

Anyhow, that’s my long answer to Benjamin’s question.

And don’t forget…

The AMA issue will be next week’s issue (March 25), so if you are interested, reply to this email with your question by Monday, March 22nd. If you want to remain anonymous, please specify that.

Note: If you are forwarded this newsletter, please be aware that it will be shutting down on April 30th, 2021, and the archives published as an eBook. So if you’re interested in subscribing, I recommend waiting for the eBook instead. If you do subscribe, please use the monthly option, not the annual one, to save me trouble wrangling the refunds.

Excerpts from Future Books

Only 7 more newsletter issues to go before Art of Gig wraps up on April 30th!

As I wind down this newsletter over these last 8 issues, I find my thoughts drifting naturally to the really long-term outlook for the future of work, like 500 years out, way beyond our own lifetimes.

It seems almost silly to ask a question like “what will the gig economy look like in 2521?” Not only do we have almost no stake in the question, making our thoughts rather frivolous, even our terms and concepts are almost certainly entirely wrong for thinking about such a question. Whatever the biggest divides in the world of work in 2521 — if “work” is even a meaningful category of human activity then — the chances that “gig economy vs. salaried” will be one of them seem quite low to me.

But the world of 2521 is still revealing to speculate about, because it puts things in perspective for you and me, living through 2021. So is there a way to get at it?

A C. S. Lewis quote I just discovered (via a tweet from Michael Nielsen) suggests one way to approach the question:

All contemporary writers share to some extent the contemporary outlook–even those, like myself, who seem opposed to it. Nothing strikes me more when I read the controversies of past ages than the fact that both sides were usually assuming without question a good deal which we should now absolutely deny. They thought that they were as completely opposed as two sides could be, but in fact they were all the time secretly united — united with each other and against earlier and later ages — by a great mass of common assumptions… The only palliative is to keep the clean sea breeze of the centuries blowing through our minds, and this can be done only be reading old books. Not, of course, that there is any magic about the past…To be sure, the books of the future would be just as good a corrective as the books of the past, but unfortunately we cannot get at them.

The quote got me thinking — in the nearly two years I’ve been writing this newsletter, like most people who write about the gig economy, I’ve sort of assumed the committed, careerist, salaried employee as the “opposed side” in our discussions. Though I’ve been careful not to cast them as antagonists, and have framed the salaried lifestyle as merely another, equally valid lifestyle choice, there is no doubt that at some level there is a deep contemporary philosophical divide between the two sides. And we’ve spent a lot of time over these past two years exploring aspects of that divide.

But what beliefs do we share with the salaried world? And what would it mean for those shared beliefs to be falsified in the future?

I’ve done my share of reading on the history of work (some of which has informed what I’ve been writing about here), but with all due respect to C. S. Lewis, the “clean sea-breeze of the past” is not actually very helpful. Unlike Lewis, I am pretty sure, if we could actually get at them, books from the future would actually be vastly more helpful than books from the past, not merely “just as good.”

How we all differ from 19th century workers is interesting to learn, but not necessarily that helpful. In fact, if we are not careful to inject irony and satire into our own nostalgic tendencies, it is easy to be inspired by the past into silly behaviors like unironically larping medieval guild life. I mean, C. S. Lewis was a talented writer, but ultimately one whose sensibilities were rooted in the past, via theology. So it’s not surprising that he thinks of the past as the source of “clean sea-breeze” rather than unpleasant smells from unidentified rotten things.

How we all differ from the people of 2521 though — that would be kinda helpful to know, since the differences should point to the weakest parts of our collective assumptions today.

We don’t have those books, but maybe we can get somewhere working backwards via a two-step formula: identify visible beliefs unquestioningly shared by both paycheck and gig economy types, and then consider them from the point of view of futures where they are not true anymore.

I tried going through the exercise and came up with the following 3 excerpts from future books:

I.

It may seem bizarre to us in 2521, but in the early twenty-first century, there were fierce arguments about whether “paycheck income” or “gig income” offered superior freedoms. The question drove strife similar to the religious strife that had dominated earlier centuries.

“Gigs” and “paychecks” were common patterns of work in the 2020s, and the differences are irrelevant for this book, but we need to understand the concept of “income” before proceeding.

“Income” was compensation for work in the form of tokens, with fixed nominal numerical values called “currency,” which were issued for circulation by governments that interfered with, limited, and constrained every aspect of individual lives, largely through the regulation of these “currencies.” “Income” played the societal role religion had in earlier centuries. All adults in the premodern era were entirely dependent on “income” to meet their needs, and were required to participate in one or more “currency” religions. In many parts of the world, you could end up imprisoned or even dead if they failed to possess enough “income.” A great deal of criminal activity was related to the acquisition of these tokens. A small minority thought the problem was the fact of government control of these currency tokens, rather than their very existence. They invented various “cryptocurrency” tokens that were supposed to eliminate such control, but ended up creating their own cult-like religious governing authorities that dominated much of the 22nd and early 23rd centuries. Another small minority thought everybody should have “universal basic income” instead of having to work for it, but they never made serious inroads.

It wasn’t until the late 23rd century that the tokens themselves were recognized as the problem, and the first serious proposals to do away with them came about, and the required kinds of Artificial Coordination Intelligences (ACIs) were developed. The result was the modern humane economy as we understand it, with freedom largely decoupled from “currencified” economic activities. Today mechanisms similar to “income” can be found in the protocols robots and computers use to coordinate use of scarce resources, so one way to understand “currencies” is as a protocol for coordination in a world where humans had to perform various essential functions that are only performed by machines today, due to lack of sufficiently powerful ACIs.

— from When Currencies Ruled the World, published in 2521, Timeline ZZ9913

II.

A startling feature of early twenty-first century life was that all humans not only expected to live only about 80 years, but they expected their final decade or two to be spent in a state of steady physical and cognitive decline, accompanied by economic hardship, known as retirement. It is a concept that is largely forgotten today, but ruled human life for nearly four centuries. To a large extent, the design of lifestyles was in fact the design of retirements.

Retirement was a period that, for most people, was shaped by pain and illness, abandonment by the young, and a barbaric system of health management that subjected most humans to painful end-of-life conditions. Writers from the 22nd century, for whom the system was still a living memory, often referred to retirement as the “death casino system.” Voluntary ending of life was illegal in most parts of the world until the late 21st century. So the last years of life were spent dealing with an array of debilitating diseases and even more horrifying patterns of “healthcare” that would be considered torture today under the Fourth Geneva Convention of 2414. Most humans spent the first 45-50 years of adulthood working as hard as they could to save enough resources to make “retirement” slightly more bearable and pain-free.

The retirement period itself, which typically lasted between 5 to 35 years, was marked by near-complete economic inactivity, with most available attention being devoted to the management of increasingly burdensome health conditions. From our perspective in 2480, this seems like barbarism. Most of us today expect to live to between 120-150 years, but have no conception comparable to “retirement” outside of temporary restorative retreats (which were called “mini-retirements” in the 21st century. Barring accidents, most of us choose to end our lives by age 130 on average. Arguably, no one alive today would tolerate the barbarism of enforced “retirement,” but incredibly enough, as late as the 2130s, people actually looked forward to the period as their “golden” years, and thought it represented a hard-won freedom! Some even tried to “retire early” as young as 30, and generally spent the rest of their lives dealing with various mental health issues.

— from Retirement: The Strange Mania that Shaped Four Centuries, Published 2480, Timeline A1871

III.

Be careful not to be caught with this book. Hide it carefully, and only make copies when you’re sure you’re not being watched. Disguise it as a junkyard temple bible if you can. In most North American junkyard tribes, being caught with this book is punishable by instant death. The warlords with their water hoards and rusty forts don’t want you to know the truth, but the world was not always like this stark desert we call home, and it doesn’t have to be that way today.

Only a few centuries ago, the world contained 9 billion people, all of whom lived lives of great luxury, with as much food and water as they wanted, and powerful medicines that could cure most diseases. All humans had marvelous computing machines in their pockets, from which they could read all the books in the world via a global communication system called the TikToks. There was no harsh struggle for survival. Most humans only worked a few dozen hours a week, and had entire days off on what was called the “weekend,” when they didn’t have to work, let alone fight. All possessed dozens of machines driven by oil, wind, and solar power, of the sort only warlords possess today. Ordinary people had more such machines then than our most powerful warlords do today. And the key to it all was a system built on something called “money” that anyone could easily earn and trade through arrangements called “jobgigs,” for whatever they needed or wanted. There was no need to kill and fight and barter. There was no need to obey the warlords. In fact, the warlords of that time were petty leaders in a few corners of the world. There was no need to scrounge through the junkyards. In fact, the junkyards of our time were not temples of secrets like the warlords’ priests say, but places where the ancients threw away broken things. We only have to live like this today because it suits the warlords. There is a better way: the way of the ancients.

But the system of the ancients had a fatal weakness, which led to the Great Collapse. You have all heard tales of the Great Collapse, and all of them are true, not myths like the warlords would have you believe. We can rebuild a world like the one that once existed before the Great Collapse, but without the flaws. But the warlords don’t want us to. So they tell us those old stories are myths. They spread lies about how the machines we have today were left behind by alien gods who built the junkyards as puzzle temples and gave the first warlords their guns. The junkyards are in fact the discarded things of our own ancestors. This book will teach you what you can do to overthrow the warlords without getting yourself killed, so we can rebuild the world that once existed, with enough jobgigs and TikToks for all.

— from Return to the Golden Age, underground book from 2621, Timeline B331

What else do we all take for granted, salaried and gigworkers alike?

What are other uncontroversial shared assumptions that might seem crazy to the future, making our disagreements seem irrelevant by comparison?

Note: If you are forwarded this newsletter, please be aware that it will be shutting down on April 30th, 2021, and the archives published as an eBook. So if you’re interested in subscribing, I recommend waiting for the eBook instead. If you do subscribe, please use the monthly option, not the annual one, to save me trouble wrangling the refunds.

Minimum Viable Practicality

Only 8 more newsletter issues to go before Art of Gig wraps up!

This week I completed ten years as a free agent. I quit my job on March 1, 2011, without much of a clue about what I was going to do.

And then I did it for ten years.

Another anniversary is also coming up in 8 weeks: the two-year anniversary of this newsletter. On April 30, on the second anniversary, I’ll be shutting down this newsletter. If you’re an annual subscriber, you’ll be getting a refund for any remaining months on your account at that point — I’m working out the mechanics of that.

Over the remaining 8 issues I’ll be wrapping up the various trains of thought I’ve been pursuing, and compiling them into an ebook or two, which will be available free to paid subscribers on the last week. Scroll to the end for a preview of what I have planned!

The reason I’m wrapping up this newsletter isn’t complicated. Some veins of writing ideas can be mined indefinitely, while others run out. Ten years ago, I did something similar with my Be Slightly Evil newsletter, which ran for 3 years and then gracefully retired into ebook-land. Art of Gig is headed for the same retirement home.

I think I’ve actually mined almost all the insight I can out of the last decade of indie consulting work. Perhaps 10 years from now, if I’m still doing something resembling indie consulting, it will be time to reboot the Art of Gig, but for now, it’s time to land this thing. Any threads I want to continue pursuing, I’ll be keeping alive elsewhere (on my other newsletter, Breaking Smart, or my blog Ribbonfarm, or via the activities of the Yak Collective).

And speaking of 10 years from now, let’s move on to the actual topic for today — shaking things up.

Back to Square One

Curiously, 10 years later after years after I first went indie, for various reasons, I feel like I’m back in the same sort of situation, itching to shake things up and head in a new direction. I can’t exactly quit my job, since I did that already, but I can do something like it. I can choose to go back to square one.

Hitting the ten-year mark is itself part of what’s causing me to reflect and contemplate a new direction (I’m kinda superstitious about round numbers), but there’s also the usual tell-tale signs that I’m getting into a bit of a rut — creeping boredom with things that were once new but aren’t anymore, wavering focus where I was once capable of engrossed attention, and a sense of having satiated the curiosities that once drove me. Even with the natural variety of the consulting life, ten years is a long time to do the same sort of thing. It’s time for a shake-up. Time for a pivot.

The pivot is not an abstract aspiration. Over the last year, I’ve already been changing my mix of activities, taking on different kinds of gigs and different kinds of responsibilities within them, and in general, switching into a much more experimental mode. The pivot has started. I just don’t know when it will be done, and in what direction I’ll be pointed when I come out of it (serious pivots tend to take me about 3 years to navigate, and I’m only 1.5 years in right now).

Though I don’t yet know what this new direction for my consulting work will be, I do know one thing: I’m solving for maximal impracticality.

Or to put it another way, since I’m also pretty risk-averse, I think of it as minimum viable practicality. Now that’s a kind of MVP I can get onboard with. It was an unconscious motive in 2011, now it’s a conscious one. One that calls for a shake-up.

Anatomy of a Shake-Up

As in 2011, there is nothing wrong, per se with the way my life is now. The last 10 years were a lot of fun, and I could easily continue doing it for the next 10. I felt that way in 2011 too.

Unlike many who make the big first leap, I had no deep frustrations or burning desire for a change in 2011. I was happy where I was, and I could see myself continuing to do the same thing indefinitely. But from earlier experiences, knew that I’d regret ignoring the feeling of restlessness, so in a way, I forced a decision I didn’t need to. I feel the same way now.

It feels like it is time to be a beginner again; a stranger in a strange land once more.

Back when I made the leap in 2011, I only knew 2 things about the decision:

  1. What I was quitting/leaving behind (a job, health insurance)

  2. What assets I was making the leap with (an established blog, a finished book, some savings)

I did get a clue a few years in though, when I identified executive sparring model as the core Aha! idea around which everything I did revolved. It became the center of gravity of my consulting life.

But when I made my first leap, I did not know that the idea of “executive sparring” would be the idea around which everything else would come together. So the leap was a true leap of faith, one that only turned out to be justified a few years in.

The trick to a good leap of faith lies in the Amazon heuristic of being ~70% sure that leaping is the right thing to do. You mitigate the risks as much as you can, and then just walk through that one-way door, trusting yourself to be as inventive as necessary to make it work. You don’t wait to hit 80, 90, or 99.99% certainty.

Trusting yourself to close an “invention gap” (a term I use in my consulting as well) is about more than trusting your own resourcefulness and imagination. It is also about trusting that you will get a little bit lucky, but without falling into the trap of waiting for that luck to magically appear. You have to prepare for luck. You have to set things up for luck. You need to put effort into the mise en place.

Mise en Place

I really resonate with Hercule Poirot’s culinary metaphor of strategic decisions emerging from a mise en place, or setting-up of appropriate conditions. In the kitchen that means acquiring the ingredients, doing the prep-work, and then beginning the cooking in a mood that is open to creative inspiration. For Poirot, solving a murder meant systematically gathering and arranging the facts, cross-checking alibis, and chasing down leads while waiting for inspiration to strike and reveal the solution.

In 2011, that process of setting up for the leap looked very different for me (and I talked about it in Your First Leap) than it does today in 2021.

For me, the setting up, the mise en place, has played out through various experiments over the last year, and in a more focused way, in the introspection I’ve been doing over the last four issues of this newsletter. Specifically, I tried to systematically think through the learnings of the last decade through 4 lenses: workflows, trust, money, and scenarios.

These weren’t randomly chosen lenses. The represent an attempt to eat my own dog food and apply the Boydian version of the Blitzkrieg model of strategic decision making to thinking about my own decisions:

  1. Fingerspitzengehfül or “finger-tips feeling” is the innate tacit skill level of good strategy, and for indies, it lives at the workflows level. I looked ±10 years through this lens in Once and Future Workflows (Feb 4)

  2. Einheit or “unity”, which I interpret as trust, is the interpersonal relationships foundation of good strategy, and for indies, it maps to relationship patterns with clients. I looked ±10 years through this lens in Spooky Trustworthiness at a Distance (Feb 11).

  3. Auftragstaktik or “mission-style tactics” is what I generally interpret as “contracts” in the broad sense of the structure of mutual expectations among strategically coordinating parties. For indies, it is best understood as the money layer of how you operate. I looked ±10 years through this lens in Money Weather, Money Climate, (Feb 18).

  4. Schwerpunkt or “center of gravity” or “main point” is perhaps the hardest element of strategic decision-making to grasp. In a reductive sense, it is just the overall goal (and often, this is how I first introduce the idea to clients), but it is really best understood as the insightful main goal, the counter-intuitive and leveraged focal point, rather than the obvious one. The focus that leads to strategic breakthroughs. It embodies the “Aha!” element of strategy, what Clausewitz called the coup d’œil, and what I like to call the “cheap trick.” There is no way to formulaically engineer the cheap trick, but you can catalyze it by doing some disciplined hindsight/foresight introspection and extrospection. I attempted this last week in Four Indie Futures (Feb 25).

When I made the leap in 2011, I didn’t have the Schwerpunkt, but by 2013 I did — the executive sparring model.

This time around, the leap actually began with accepting the Berggruen fellowship and moving to Los Angeles in 2019. The pandemic proved to be a good opportunity to disturb my own equilibrium even further. So while I haven’t settled on a new direction, I’ve definitely succeeded in unsettling my old direction into something resembling a random walk. I’ve achieved product-market-unfit.

Now, early in 2021, I still don’t have a new Schwerpunkt, but I do have lots of interesting ongoing experiments that I started in the past year. Here are some of the highlights:

  1. I began exploring decentralized network models for indie work with the Yak Collective, an effort that’s in an interestingly critical place now, and to which I plan to devote more attention.

  2. I’ve adopted a significantly more vertical approach in my consulting gigs, learning and applying a lot more within a few select focal industries, instead of a generalist, horizontal approach based on abstract management ideas.

  3. I’ve been cutting back sharply on my sparring work, in general saying no to new clients unless there is a vertical/depth aspect that interests me. Partly because sparring is exhausting, demanding work, and partly because it is sharply depth-limited in terms of the kinds of things I want to learn now.

  4. I’ve started doing hands-on dabbling in projects to teach myself things I don’t get an opportunity to learn directly in gigs. Things I suspect will help open new doors/opportunities, especially in the post-Covid, decarbonizing economy, but which I chose because primarily because they’re fun.

  5. I’ve gotten interested and invested in a few larger trends that transcend particular gigs — climate tech and AI in particular — calling for spec-projects and proactive efforts.

  6. I’ve started deliberately maneuvering out of the orbit of Silicon Valley as my “home” economic zone (but without a clear idea of a new zone to head towards).

  7. I’ve been rethinking the relationship between my writing and consulting (wrapping up this newsletter will create bandwidth for other writing projects I want to grow more).

There are several other ongoing experiments, and I fully expect many of them to fail. The point is, setting things up for a strongly experimental phase, making the leap, and then actually getting experimental, is the only way I know to uncover a new “strategy.” Ready, Fire, Aim. You don’t uncover new strategies by sitting back and staring philosophically at a blank whiteboard. Or at least, I don’t.

When I look at everything that I’ve set up, and all the cunning experiments I have ongoing, I feel a bit like I did back in college. Exploring without a clear sense of what I’d find, or what I’d do with it once I found it.

While I don’t have a big insight about the new Schwerpunkt to re-orient around, I do see some principles beginning to emerge. The biggest one is this: solving for impracticality.

Solving for Impracticality

One of the things that’s probably not obvious about me from my public writing and shitposting on twitter is that I’m intensely practical, risk-averse, and fond of my creature comforts. I’m not an entrepreneur. I have no intention of ever chewing glass while getting punched repeatedly in the face like entrepreneurs are supposed to. I’m not an artist or poet, and even if there is any accidental art to what I do, I’ve never in my life “suffered for my art,” and don’t intend to start now.

I solve for a comfortable life demanding minimum energy; one which leaves me with the maximum possible surplus of time, money, and energy. A surplus which I then proceed to waste with as little thought as possible. If there’s such a thing as a life lived in service of a higher calling, mine is the opposite of that.

It’s living life like a shitpost, and that’s the way I like it. To use Thorstein Veblen’s term from Theory of the Leisure Class, I’m basically a savage. And I’d like to remain one.

Unfortunately one of the harsh realities of aging is that surpluses of all sorts start to dwindle, and if you don’t periodically adjust your approach to life, the cost of simply continuing as before creeps up, surpluses shrink, and before you know it, a life that was 50% leisure is now 5% leisure. Think of it as shrinking gross margins of leisure in an aging business.

  • The boundless physical energy that most can take for granted at 25 takes a consciously cultivated diet and exercise regimen to keep up at 45.

  • The vast expanses of weekend and evening time that exist at 25, when you’re single and living out of a suitcase, somehow fill up with family time, chores, and maintenance.

  • Money goes from something you don’t take seriously because you have so little, to something you have to take seriously because you have more. And because old age and retirement loom, and with every passing year, there’s less time to recover from bad mistakes in managing money.

People don’t turn into responsible adults doing mostly serious, important things because they actually aspire to do so, learn the necessary adulting skills, and “put away childish things.” Well maybe some people do — that stuffy pompous kid from grade school we all knew probably couldn’t wait to get there.

But I suspect for most of us, “childish things” — really, the savage leisure surpluses that make life worth living for most of us — get squeezed out as life encroaches on dwindling surpluses. Turning adult is really about life civilizing you by taking away your surpluses.

Which means you can no longer take room for impractical things for granted. You have to make room for life lived as a shitpost. You have to solve for impracticality in your life, by solving for minimum viable practicality.

So that’s what I’m setting out to do over the next few years.

Before we wrap up for today, let’s do a quick preview of the remaining issues:

Preview: The Last Eight Issues

  1. If there are enough questions, I’ll be devoting at least one issue to an AMA. So if you have a question, now’s the time to ask it. Keep it simple and short, and I’ll do the same.

  2. I’ll also be reserving at least one free newsletter issue (which will go to ~3700+ people) to showcase other indie consulting/gig economy newsletters people might want to subscribe to. So if you write one and would like to be featured, send me a 100-word blurb, with inline links to a couple of your best issues. I’ll share up to a dozen newsletters in the showcase issue.

  3. One issue will be devoted to the finale of the long-running Yakverse fiction series.

  4. One issue will be devoted to book recommendations.

  5. For the remaining 4, I don’t have a plan yet, and I’m open to suggestions.

Four Indie Futures

In the first three parts of my look at the evolution of the gig economy from my own 10-years-in perspective, I looked ±10 years at the 3 layers of the stack that I think of as forming the background canvas of our work: workflowstrust, and money.

In this part, I want to explore what I think of as the element between foreground and background: scenarios. Scenarios are how you imagine how evolving patterns in workflows, trust, and money coming together around big, external, non-economic forcing functions to form larger economic stories. These stories cannot be told in the form of a “view from nowhere.” They can only be told from a particular interested perspective: in our case, that of the indie consultant.

Looking out at the future is only a meaningful exercise if you look back at least as far in the past: after all scenarios that cannot even achieve consistency with the past have little hope of comprehending the future. And for telling big stories and positioning yourself within them, you have to look past the boundaries of your own chapter.

But to avoid getting trapped by a single story, you have to tell yourself multiple stories.

Four Stories

Here are 4 ways to look at the last 50 years of consulting, and corresponding ways of looking at the next 10 years. These 4 scenarios are very US-centric, but there will always be some bias in this sort of scenario construction, and US-centricity remains the best bias for telling any story of global significance. In the future, China-centricity might be the right way to develop scenarios, but we’re not there yet I think.

These are not meant to be great models of evocative storytelling, but as quick glosses of stories that seem implicit in the way significant clusters of people seem to think about indie consulting.

Story 1: A New Technocracy

Modern consulting emerged in the 1970s following the oil shocks and the rise of Japanese competition, making the MBA a sought-after degree. With deregulation, through the eighties and nineties, it continued to grow as an industry in prestige and influence, and came to be regarded as the main repository of business knowledge.

After 2000, the growth of the digital economy, and increasing perceptions of cronyism, corruption, and being out of touch began to slowly tarnish the reputation of the sector. The industry found it especially hard to make inroads into the emerging technology sector, which had a natural hostility to MBA-style consulting. Though it managed to establish a foothold, especially on the business side of the larger companies, it could not penetrate to the technological side, or down to the smaller startup scales, where much of the real action was.

Unlike in the old economy, big institutional consultants were essentially cut out of the most consequential conversations, even though they were able to access a large share of the available money. Talented young people in MBA programs read the writing on the wall, and increasingly began migrating directly to the heart of Silicon Valley, choosing to work in VC firms, directly for big companies, or even found startups. Others began migrating to Asia, establishing direct footholds and expertise in the Chinese sphere of influence.

In this environment, independent consulting began to take root, especially around boutique needs requiring deeper technical knowledge, alloyed with management experience in the new economy.

Over the next fifteen years, a large boutique industry of indie consultants emerged, offering expertise in every aspect of the new economy from SEO and growth hacking to product strategy and UX design, to database scaling and sourcing manufacturing in China. Blogs, newsletters, Twitter, and podcasts became the preferred source of business expertise, displacing traditional sources like consultant company reports, business books, or the Harvard Business Review. Private online forums began displacing old-style backroom conversations.

Through the Great Weirding (2015-20), the divide grew deeper, as the old consulting industry became increasingly out of touch, and the emerging indie sector gained credibility and professionalism rapidly.

In the next 10 years, the trend will continue, as indies organize more effectively to take on larger, more complex engagements, and offer more imaginative services at lower cost, with less focus on paper trails and manufactured justifications and more focus on fundamental problem solving. They will go beyond solo gigs to networked collaborations in larger teams.

As we head into an era defined by climate change, decarbonization, and deep reconstruction, indies will be critical to navigating events with agility and real problem-solving intelligence, since technology is the main lever for addressing the big challenges of the post-Covid world.

Sclerotic and cronyist consulting firms will be left behind and die along with the old economy they serve.

Story 2: A New Socialist Hope

Modern consulting emerged as a dark force in the 70s, as several decades of thoughtful and compassionate politics from FDR to LBJ drew to a close, and the ambitious social programs of the Great Society floundered during the Nixon administration.

An economy founded on treating workers well and fostering inclusive growth gave way to the rapacity of neoliberalism, marked by the greed of supply side economics, globalization, union-busting and deregulation. For a quarter of a century, traditional consulting served as the mercenary sword arm of capital, extracting an ever-greater share of profits from labor, and working with oligarchs and totalitarian regimes across the world to create and secure a global system of exploitation. Unions were busted, environmental and civil rights concerns were tossed aside, and sociopathic business leaders, supported by consultants, systematically stole the future from the people and made it the preserve of the 1%.

In this environment, indie consulting emerged as a boutique segment of individuals who combined highly valuable technological skills with a sense of integrity and ethics. Between 1992-2015, indies used the cheap and disruptive tools and technologies provided by the internet to gradually create and offer a systematic alternative to the corruption and cronyism of the old economy. At the same time, they pioneered a third way of work, rejecting both the role of neoliberal exploiter and exploited low-agency worker, to make their own way with dignity, using digital tools to asymmetric advantage.

Through the Great Weirding (2015-20), the contradictions of the neoliberal world order finally became unsustainable. And though Bernie Sanders did not win in 2020, the election of Joe Biden finally offers some hope for a new, more equitable future, and a return to dignity and prosperity for all has become possible.

In the next decade, indies will be at the forefront of a revitalized middle class and a socially aware and ethical response to climate change. Though unions are obsolete and beset by the same kinds of corruption that plague other neoliberal institutions, new kinds of collective action based on a new authenticity and post-capitalist modes of solidarity will emerge. Indies will be at the head of this movement.

A compassionate, socially conscious, networked workforce, supported by mechanisms like UBI and universal healthcare, will emerge to form the new backbone of the post-Covid decarbonizing economy.

Story 3: More Neoliberal Than Thou

Modern consulting emerged in the 1970s alongside fresh new ideas in economics and wealth creation. Thanks to the oil shocks and Japanese competition, moribund and inefficient American industry was shocked out of its complacency and forced to scramble to remain competitive. Decades of indulgent socialist policies had created a corrupt, bureaucratic, and inefficient economy with stagnant innovation, weak leadership, and a non-existent strategic culture.

Between 1980 and 2000, consulting played a critical role in making the American economy competitive, efficient, and innovative again, driving the greatest burst of wealth creation in history. It however, became a victim of its own success, growing complacent and corrupt in turn.

Indie consulting emerged alongside the internet as an agile, entrepreneurial, and effective alternative source of business knowledge and strategic capability that slowly began beating the traditional consulting world at its own game. Using the internet as a tool for asymmetric advantage, it slowly established itself as the go-to source of competitive advantage in the emerging tech industry. A new economy built on startups needed a new kind of consulting that was itself organized in startup-mode.

Through the Great Weirding (2015-20), the indie world finally came of age, with its own “passion economy” stack allowing it to compete sustainably. In the next decade, traditional consulting will recede and decline, and as the passion economy stack matures and grows, indies will grow along with it. Blockchain-based technologies will be especially important in this evolution.

The future will only have more and more post-industrial, post-capitalist weirdness and the unique challenges of climate change, which will not yield to business-as-usual thinking.

Indies will be at the forefront of helping the economy innovate its way through the challenges of a post-Covid decarbonizing economy with an entrepreneurial approach to big problems.

The traditional consulting industry, full of empty suits, may have started this game, but indie consultants, armed with just a laptop, internet connection, and blockchains, will finish it. The traditional consulting world will simply be unable to keep up in this accelerationist future.

Story 4: The Empire Strikes Back

Modern consulting emerged in the 1970s alongside monetarist economics and globalization. It was instrumental in creating the neoliberal world order and the great wealth that flowed from it.

When the internet economy emerged in the 2000s, the traditional consulting industry was initially caught flat-footed, but it learned rapidly and reinvented itself. It soon became an essential part of the new economy. In the first two decades, the tech sector had all the problems of emerging frontier economies. It was full of grifters and amateurs wielding outsize influence, and playing roles normally played by seasoned business veterans. Due to the small scale of much of the early-stage startup world, and the newness of the technologies being adopted rapidly, it took some time for the traditional consulting industry to catch up. But as the early tech companies grew into giant platforms that dominated the economy, consulting firms reinvented themselves for the digital age through acquisitions and building up of new tech practices. They successfully migrated from the old economy and established themselves as partners for the new economy, bringing much-needed professionalism and seriousness to the sector.

In the future, as tech matures and large companies continue to shape the future, the wild frontier of indie consultants and boutique operations will consolidate and become integrated with the traditional consulting industry. A new normal will emerge, leaving behind the anomalous dynamics of the Great Weirding (2015-20) will soon be a distant memory, like the Wild West.

As climate change and China increasingly become the priority for businesses post-Covid, the resources, scale, and deep global expertise of the the consulting industry will once more come to the fore. The wild west will be tamed, and deep expertise and institutional knowledge will come to be valued once again.

Eight Questions

Before we proceed, ask yourself these 8 questions:

  1. Which scenario do you most resonate with?

  2. Which one do you least resonate with?

  3. What can you see with greater clarity through each story

  4. What are the blindspots baked into each story?

  5. What sort of indie is described by each story?

  6. What sort of client is described by each story?

  7. Which of these stories are best/least supported by known numbers?

  8. What story threads do the available numbers not capture?

If you like, post your thoughts on these questions as comments below.

Now for some commentary.

Seeing Through Scenarios

In case it isn’t obvious, these 4 scenarios correspond roughly to the 4 quadrants of the well-known political compass:

  • Story 1, A New Technocracy is a Left Libertarian future

  • Story 2, A New Socialist Hope, is a Left Authoritarian future

  • Story 3, More Neoliberal Than Thou, is a Right Libertarian future

  • Story 4, The Empire Strikes Back, is a Right Authoritarian future

I’m probably hoping for Story 1 with some elements of Stories 3 and 2, perhaps an 70-20-10 mix, but that’s probably wishful thinking. I suspect the actual future will be about 10-20-5-30, for a total of 65%. I’d guess about 35% will be stuff nobody saw coming.

There are, of course, way more than 4 stories that can be told about the next ten years, and every way of reading the past leads to a way of reading the future. And every story offers its own way of grappling with known new elements in the landscape and unknown unknowns.

In this case, the new elements I incorporated are: Covid, China, Climate, and Crypto. The 4Cs of futurism today. They are not the only elements stories could or should be aware of, but scenario building is about making choices, since you only have so much room in a story.

The trick is to tell yourself many stories, and believe in all of them enough to become sensitized to the truths they uniquely apprehend, but be skeptical enough of all of them to avoid getting wishfully attached to, or blinded by, any of them. That is perhaps the best way to leave yourself open to the upsides of what nobody saw coming, and prepared against downsides that at least somebody saw coming.

Next week, for my 10th anniversary post, I plan to pull together this series with a grand finale exploring the most important question: what am I going to do with myself?