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.

1

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.