Art of Gig: 2020 Roundup -- Resend

It's been quite a year for the gig economy.

Accidentally sent this annual roundup email to just the paying subscribers list when I meant to send it to the whole list.

But while I’m resending, I’ll add a logistics note: several readers alerted me that they ran into issues with subscriptions not auto-renewing recently.

If your subscription was set to automatically renew, but instead expired in the last few weeks, you should be able to manually resubscribe. I’m talking to substack support about this. Let me know if you face further issues.


It’s been quite a year for this world, the gig economy, and this newsletter. My best-laid plans for what I was going to write about got derailed around March, and I ended up charting an unexpected course through 2020. Here’s a round-up of all the newsletter issues, with some loose organization and commentary.

Main Series

I published 37 newsletter issues on various aspects of the indie consulting life (36 by me, 1 guest post). In this main series, there were 26 subscriber posts and 11 free posts. Most issues were probably intermediate/advanced, suitable for indies with a couple of years experience, but there were a handful of issues suitable for newbies.

  1. 1/9/20: The Importance of Being Surprisable: As an indie, being more open to the world than clients is your super-power. Your job is bringing surprises to the party. 🔒

  2. 1/17/20: Basic Consultant Diagrams: This was probably the most fun post of the year, a survey of diagrams you should master as a consultant.

  3. 1/24/20: Ten Dimensions of Gigwork: An anchor post for this newsletter, laying out key concepts and structural dimensions.🔒

  4. 1/30/20: Bootstrapping with Beefs: A post dedicated to the late Clayton Christensen, exploring how to use beefs to get your indie career going 🔒

  5. 2/13/20: Indie Fragility: The indie life is precarious and fragile. Taking that fragility seriously. 🔒

  6. 2/20/20: Your Passion Mission: How to arrange your money-making activities around your soul-feeding activities.

  7. 3/12/20: Gigging in the Time of Corona: My “first response” post on Covid, which led, among other things, to getting the Yak Collective off the ground.

  8. 3/26/20: Getting to the Reset: Probably one of more popular posts of the year, on how to get to the reset post-Covid.

  9. 4/2/20: Murder on the History Express: Covid is the death-knell of the industrial economy. What that means for indies.

  10. 4/8/20: Get Fat: Adopting fat thinking principles for navigating Covid.

  11. 5/7/20: What Color is Your Halo?: When you walk (or zoom) into a client organization, a certain perception accompanies you. How do you manage that? 🔒

  12. 5/14/20: Introduction to Executive Sparring: An introduction to a series (4 parts published in 2020) on the primary kind of consulting work I personally do, executive sparring.

  13. 5/21/20: The Guru Factor: The perils and perks of being viewed as a “Guru” and how to navigate that perception within a sparring practice. 🔒

  14. 5/27/20: Sparring as Tenure (guest post by Tom Critchlow): An analogy between being able to build and sustain a sparring practice and getting tenure in academia.

  15. 6/3/20: I’m Ok, You’re Ok, They’re Not So Hot: Exploring the “problem social graph” and the central dogma of sparring, that you must hold to be an effective sparring partner. 🔒

  16. 6/11/20: The Way of the Mercenary: A personal favorite post from the year, exploring the roots of indie consulting in the history of literal “free lances” 🔒

  17. 6/18/20: Model Questions vs. Actor Questions: A meta-question to ask about your questions, especially as a beginning indie.

  18. 6/24/20: Where Should You Live?: A post on a very simple but strategically important question: where to live to further your indie career/leverage. 🔒

  19. 7/2/20: Consulting as Investing: Similarities and differences between consulting and investing, and how far you can take the analogy between them. 🔒

  20. 7/9/20: Dulce Officium: Covid has given me a new appreciation of offices (both physically, and conceptually) as refuges from economic storms.

  21. 7/16/20: A Map of Indie Consulting: An attempt to map out the various subsectors of indie consulting. 🔒

  22. 7/24/20: Leaders and Indies: Why indies should try to work directly for leaders as much as possible, instead of intermediaries. 🔒

  23. 7/30/20: Leverage Curves vs. Career Paths: Paychecks come with the notion of progression along a “career path.” What is an equivalent for indies?

  24. 8/6/20: The Art of Being Unmanaged: Viewing the freedom of free agency specifically as freedom from being managed, and what that means.🔒

  25. 8/13/20: The Prosumer Gambit: The deep nexus between the indie life, and being a prosumer/lifestyle designer. 🔒

  26. 8/19/20: Dog-Fooding for Indies: Exploring the difficulties of applying the “eat your own dog-food” principle for indies. 🔒

  27. 8/27/20: Reality-Arbitrage vs. Dog-Fooding: Following up on the previous week’s article, offering an alternative to dog-fooding that works for indies. 🔒

  28. 9/3/20: Fourth-Wave Consulting: One of my most popular posts of the year, analogizing the evolution of consulting and… coffee.

  29. 9/10/20: Free Cogs: Reconciling the metaphor of workers as cogs in machine with the idea that the gig economy is about freedom.🔒

  30. 9/23/20: Return of the Clutch Class: A rare political post, building on a post from 2019, arguing that gigworkers should embrace their scab-like perceptions.

  31. 10/1/20: Messengers of the Medium: Building on The Way of the Mercenary, a view of indie work as being messengers of the medium, suited to endgames. 🔒

  32. 10/8/20: Gigification as Gamification: An appreciation of James Carse, author of Finite and Infinite Games, who died this year, via a game-like view of gig work. 🔒

  33. 10/15/20: Time Capitalism: A post (with a math formula!) on how and why to think of yourself as a time capitalist. 🔒

  34. 12/2/20: Going Indie is Going Amateur: Tracing the connections between the indie ethos, the allure of professionalism, and the best kind of amateur sensibility.

  35. 12/9/20: Don’t Build a Hill to Die On: Why can’t clients see that you are the solution to their problems? Possibly because you’ve built a hill to die on that’s more about you than them. 🔒

  36. 12/16/20: Depth in Freedom: A post on what it means to “go deep” as an indie, why you can never feel as certain of your depth as regular career people, and how you can go deep anyway. 🔒

  37. 12/24/20: Appreciative Myopia: Sometimes, real perspective lurks in the weeds. A post on why indies might benefit from having a short-term perspective. 🔒

The Yakverse Chronicles

New readers may not be aware that there’s a second track of issues in this newsletter, a consulting-life-themed fiction series called The Yakverse Chronicles, featuring both episodic adventures and a long arc story. You can find the series home page here, and read from the start.

In 2019, I wrote 11 parts in this series, but in 2020, I only wrote 3 additional parts (all subscriber-only), bringing the total up to 14. It was kinda hard to write relatively light-hearted fiction in this grim environment. I plan to write the final chapter in January, and wrap up this story. The three parts from this year were:

  1. And So It Begins: In which my old nemesis, Ulysees Alexander Khan reappears with a strange proposal for Guanxi Gao, Arnie Anscombe, and me. Do we trust Khan? Do we trust the shadowy group he represents, known as the Club? 🔒

  2. Staying with the Questions: In which we ponder the strange 2x2 Khan left us with, and ponder our postures for the pandemic. 🔒

  3. Yakverse: Infinity Gig: In which the Yakverse Chronicles head towards a stunning resolution. 🔒

The Yak Collective

One of the more interesting that came out of this newsletter this year was the Yak Collective (the name was inspired by the Yakverse series). A few buddies and I kicked it off in March, and it has since grown into a 600+ person network of indie consultants and people interested in the indie life.

The Collective has completed 5 collaborative projects, (4 internal, one team gig for a client), and bootstrapped itself as a really interesting space. It has been especially impressive to see how people have pulled together in entirely emergent ways, and self-organized to build out some really powerful infrastructure.

My own main contribution, besides supplying a name, has been doing the initial instigation, running a track of chats, and participating in a couple of the projects.

If you are interested in pulling together a Yak Collective team for a client project, get in touch. We now have validated capabilities of various sorts — trend reports, pop-up think tanks, futures studies.

And of course, we continue to do internally-initiated projects for fun, capability development, and collaborative team building. We have a bunch of these lined up for 2021 already, and I’m really looking forward to seeing where the Yak Collective goes in 2021.

Looking Ahead at 2021

I haven’t yet made clear plans for where to take this newsletter in 2021. I plan to wrap the Yakverse Chronicles and the executive sparring series, but beyond that I haven’t decided on a direction yet.

So if you have ideas or suggestions, do share.

See you in January!