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.