Month: March 2021

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.

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.

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.

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.