Art of Gig: Year One

I can’t believe it’s been a year already, and time for the first Art of Gig annual review issue 😦.

I started this email newsletter on April 30, 2019, and here we are now, 54 issues later, in the middle of a pandemic, trying to run an already difficult playbook in perhaps the toughest environment ever. If we get through this, we should award each other medals.

More on that, and on where we go from here, at the end. But let’s do a review of all the Year One articles first, grouped in hopefully helpful ways. If you’ve been meaning to introduce any friends to this newsletter, this would be the issue to forward (or even give them a gift subscription perhaps?).

First Leap Series

Though most of the content in this newsletter is aimed at people who are already in the gig economy, particularly as indie consultants or freelancers, I did write some material explicitly with potential new entrants in mind, in the form of a five-part series covering the basics of preparing to leap into the gig economy.

  1. The First Leap: Employees hunt, entrepreneurs launch, gigworkers leap. Understanding how to enter the gig economy.

  2. Leap Risk: The financial math and risks of leaping into the gig economy, and what you can do to mitigate it.

  3. Minimum Viable Cunning: How to inject enough strategy into your first leap to manage the risk.

  4. The Inner Game of Gigwork: Managing your inner life by becoming more of a robot to express more of your humanity.

  5. The Road to Agency: Concluding the five-part series, mapping out the path to gaining control over your own life, which is what typically drives those who manage to last in the gig economy.

This series was partly paywalled, but I’ve made the whole series public now, in case it is helpful to people suddenly thrown into the gig economy due to the crisis.

While this First Leap playbook is obviously much harder to run in the Corona era, it is still the minimum-viable playbook you have to run. If you’re new to the gig economy (voluntarily or involuntarily), or still in the paycheck economy and eyeing it as a future option, this series should be helpful.

Core Articles

The heart of Art of Gig is a track of essays where I try to pick out and discuss themes that are important, but not always obvious if you’re new to the game. The bulk of these essays are intermediate level, and assume some work experience, if not indie experience. I wrote 20 essays on this track in Year One.

  1. Elements of Consulting Style: The 4 types of clients and how to serve them: achiever, integrator, explorer, tester.

  2. A Tale of Two Schools: An introduction to the structuralist versus people school philosophies of consulting, and why indie consultants tend to fall on the people school side. 🔒

  3. Knowing Which Nut to Tighten: How do you price your knowledge? Consulting and the principal-agent problem. 🔒

  4. You Are Not a Scientist: Gigups and startups share an important attribute: neither is science-based. A “scientific” self-image of what you do/know is a liability. 🔒

  5. Response Regimes in Indie Consulting: What mix of risk and time pressure do you help your clients respond to? A typology of 4 kinds of needs met by indies: strategy, first response, preventative care, and surge capacity.

  6. When is a Gig an Engagement?: The importance of not haggling to positioning yourself as a consultant, rather than a contractor.

  7. The Clutch Class: Gig workers are neither part of capital, nor part of labor; we are the clutch class. An examination of our role in the politics of work. 🔒

  8. The Gigwork Hierarchy of Needs: A combo mid-year review and a diagram organizing indie learning/maturation on a Maslow-like hierarchy.

  9. The Price of Freedom: The fundamental choices and consequences of gigwork, in the form of a helpful pick-2-of-3 triangle diagram. 🔒

  10. A Self-Image is a Dangerous Thing: A self-image is a dangerous thing for indies to have, because it’s likely to end up an ersatz knockoff of a paycheck role. Instead, you have to be a trickster of sorts, crafting a persona to suit the gig. 🔒

  11. Sneaking Away From Yourself: You’re a bad boss, and you should sneak away from yourself. There’s no point taking the gigworker out of the paycheck organization if you can’t take the paycheck organization out of the gigworker. 🔒

  12. Training Your Nerves: As a free agent, your nerves matter more than your skills. How do you systematically train them?

  13. The McKinsey Affair: Lessons for the indie consultant from contemporary events in the Big 3 world, particularly the gradual tarnishing of McKinsey’s brand. 🔒

  14. You Are Not a Parasite: Consultants are often accused of being parasites. Weak organizations always harbor parasites. The question is, are you one? 🔒

  15. The Importance of Being Surprisable: The superpower of indie consultants is openness to being surprised. 🔒

  16. Basic Consultant Diagrams: I diagram therefore I am. An introduction to the basic diagrams that come up in consulting work.

  17. Ten Dimensions of Gigwork: It is important to understand the class hierarchy of the gig economy. Are you a consultant, contractor, or platformer? Ten ways you can tell. 🔒

  18. Bootstrapping with Beefs: To find clients, start beefs, a tribute post to Clay Christensen. 🔒

  19. Indie Fragility: Indie businesses are fragile. It is important to come to terms with that fact (this was written just before the Covid19 crisis hit). 🔒

  20. Your Passion Mission: Arranging your money-making around your soul-feeding. If you don’t do this, your career in the gig economy will likely not be sustainable psychologically.

The Yakverse

If the core articles are the heart of this newsletter, the soul, at least for me, is the Yakverse series. Currently, the series stands at 13 parts, with 2 ancillary special posts.

The series has its own series home page.

The Yakverse is a fictional universe within which I set a series of somewhat absurdist stories inspired by my consulting work/experiences. I will be the first to admit that these are not exactly Dickensian masterpieces of fiction. This series is the most experimental part of this project for me. I’m trying to do several things with it. There’s an element of teaching consulting through stories, and an element of teaching myself world-building and fiction writing at your expense.

But the biggest goal of the Yakverse series, frankly, is just having some fun. The gig economy can be a grim, even depressing place, a place that can turn into All Soulless Hustle All The Time if you’re not careful. I have fun writing the series, even if not all episodes work. I hope Season 2 improves. Maybe I’ll even get a Netflix deal to make an animated series out of it. One can dream 😎

I know from your feedback that for some of you, this is the most fun part of the newsletter, and for others, it feels like hit-or-miss rambling and a distraction from the more “practical” track of core articles. Thanks for either coming along for the ride, or putting up with it, as the case may be 😆.

Tips and Tricks

I am a huge believer in aphoristic, fortune-cookie level wisdom, which I put out on the @artofgig twitter account. Here are compilations of all those tweets, plus the very first proper newsletter, which was also a collection of fortune-cookie sized thoughts.

  1. 42 Great Imperatives

  2. Consulting Tips Compilation: 1

  3. Consulting Tips Compilation #2

  4. Consulting Tips Compilation #3

  5. Consulting Tips Compilation #4

  6. Consulting Tips Compilation #5

  7. Consulting Tips Compilation #6

  8. Consulting Tips Compilation #7

  9. Gig Economy Trivia Compilation #1.

Pandemic Specials

The crisis is a very special condition for the gig economy, and I’ve been writing a series of posts on that, all are public.

  1. Gigging in the Time of Corona

  2. Getting to the Reset

  3. Murder on the History Express

  4. Get Fat

Community Stuff

I haven’t written much about the community side, but I laid out my basic philosophy in Towards Gigwork as a Folkway. About a month ago, I took the first steps towards putting that philosophy to work. There is now a nascent community brewing, which we’ve tentatively named the Yak Collective. The basic community infrastructure is free and open to all, not just paying subscribers.

Right now there is a growing resource database with resources like case studies, a gig exchange page, and a directory. There is a Discord with over 300 members, and a track of experimental voice chat sessions. There is a first significant collaboration ongoing — on a Covid19 reboot strategy deck.

Not all of this will work, but hopefully enough of it will to get a mutually useful and interesting community going. For those of us who have been in the indie economy for a while, this Covid19 period feels like a highly stressful coming-of-age period. The kinds of experiments we try through this period, and the resourcefulness and imagination we bring to the party, will determine whether the pandemic destroys the nascent gig economy, or boosts it to a whole new level.

Thanks to all who have been helping with this early experimental phase, and figuring stuff out: Paul Millerd, Tom Critchlow, and Pam Hobart in particular. Thanks also to all those hosting voice chat sessions and figuring out how best we can be of value to each other, one conversation at a time: Scott Garlinger, Jordan Peacock, Drew Schorno, Sachin Benny in particular. Apologies if I missed anyone.

We will get this stuff much better organized in the coming months hopefully, as we slowly figure out what works by trial and error, double down on things that work, and put better scaffolding around it.

I will also be reinvesting some of the subscription income from this newsletter into the community component, once we figure out good ways to do that.

Year Two Prospects

As of today, this newsletter goes out to 2124 people (thank you!), of whom 380, or around 17%, are paying subscribers (double thank you!).

For Year Two, I had planned out a few big themes to explore, but like all of the best-laid plans, the pandemic has trashed them. So for the time being, I’ll be on an improvisational track, watching and writing about the gig economy and indie consulting as it responds to, and evolves, in response to the crisis.

Many fundamentals of the indie world have changed, some perhaps permanently. But many more fundamentals haven’t changed. The basic game is still drumming up leads, closing the deals, hustling through them, chasing down invoices and getting paid — all while having fun, learning, and growing with each pass through that process.

So I will be continuing to write about those fundamentals too, at all levels from beginner to whatever level I’m at. The pandemic will eventually recede, but most of us will still be here I hope, going on going on, hustling and scheming the same as ever.

So once again, thank you for your support and participation through Year One. Onwards to Year Two.

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