The Gigwork Hierarchy of Needs

We’re now 4 months into the Art of Gig, and this is my 25th newsletter. I am finally beginning to get a sense of what I’m doing here, so I am ready to start pretending this is what I was planning all along.

As we switch gears from summer mode to fall mode (indie consulting is a game with strong seasonality to it), it is time for me to do a proper guided tour of the ground we’ve covered so far, so you can see and navigate the bigger picture taking shape, and get a sense of my cunning plan to catalyze a Brave New Age of Gigwork.

The key to both is this maslowesque hierarchy of needs diagram.

Towards a Full-Stack Conversation

The current larger conversation about the gig economy is almost entirely — to the tune of 90% — bogged down in the two bottom layers of this pyramid, narrowly concerned with questions of lead conversion rates and financial survival, and a < 2 year strategy horizon. By contrast, the corresponding conversations about regular careers, or startup entrepreneurship, are much more mature and full-stack, covering the entire equivalent pyramids, and lifespan-length horizons.

When I started out in 2011, there was little to no useful advice out there on how to actually go about crafting a satisfying and meaningful life out of internet-enabled gigwork. Much of what I read amounted to religious ranting about the moral superiority of free agency, cargo cult “systems”, uncritical dogmas about the superiority of “value-added” consulting, ethically dubious arbitrage games, and most worryingly, widespread predatory contempt towards clients (paradoxically alloyed with whining victimhood).

And of course, lots of exhortations to aggressively chase leads, spray-and-pray pitches at potential clients, and generally be an obnoxious, glad-handing hustler 24×7. The gig economy is not immune to hustleporn.

Much of what I read was actually lazy ports of how-to wisdom from two sources: entrepreneurship and sales. Almost all of it was useless because indie consulting and gigwork are not like either of those activities. The superficial base-layer similarities — necessary reliance on a conversion funnel, and precarious cash flow — leads people to ignore deeper and more consequential differences.

I decided very early on — like a couple of months in — that if success and survival in the gig economy meant exhausting zombie hustling and soulless grinding, I didn’t want it. So I decided to figure out my own playbook. I’m now 8 years, 1000s of hours, and dozens of clients into running that playbook, so I think I can say with some confidence that the Art of Gig playbook I’m slowly laying out in these newsletters has been validated at least at an n=1 level.

With 25 issues worth of hindsight, my goal with this newsletter has been to try and level up the conversation around gig work into a full-stack conversation, where people like you and me are talking about all levels, rather than just the bottom levels. So here is a tour of the newsletter issues so far, sorted by level.

Leads and Deals Level

The newbie leads-and-deals level of indie consulting is, in my opinion, best tackled by diving right into the deep end with just a vague idea of what you’re going to do, and a few months worth of savings to live off while you figure it out. What you’re solving for at this level is simply leads and (closed) deals, and bringing in the money by any means necessary.

But it’s a mistake to try and work that problem directly, by playing it like a formulaic numbers game the way sales people sometimes do. It may work in the short term, but it’s a recipe for very quick burnout. As with any kind of gambling, be wary of people selling you “systems” that are “guaranteed” to deliver a certain return rate in conversions and closed deals.

No “system” to enter indie consulting survives first contact with a No! from a potential client, or the first bout of cash-flow panic. So it’s best to just dive right in. Just focus on making money any way you can, and acquiring a broadly useful situation awareness of how the game is played. You can worry about theorizing your model later.

The consulting tips I tweet from the @artofgig account, and compile here, are a good place to start, as are “grown-up” discussions with experienced consultants (as opposed to patronizing baby-talk discussions). Don’t worry if they seem either irrelevant or like very distant concerns. My goal at this level is to help you develop a big-picture awareness, via aphoristic exposure, of full-stack consulting lore and wisdom. Drawn not just from my own experiences, but from those of people who I think are doing it right.

1. Consulting Tips Compilation: 1 (public)

2. Consulting Tips Compilation #2 (public)

3. Consulting Tips Compilation #3 (public)

4. Consulting Tips Compilation #4 (public)

5. Consulting Tips Compilation #5 (public)

6. 42 Great Imperatives (public): A list of 42 principles at all levels from newbie to experienced, dropping you off the deep end for situation awareness.

7. Discussion: Gig Economy Forecast: A discussion thread of current trends in indie consulting, based on a 2×2 prompt classifying trends into sectoral, global, management, and creative-destructive.

Free Cash Flow Level

If you get stuck in the leads-and-deals level, you probably won’t last longer than 6 months. Even if your funnel is converting well, and generating enough income to live on. Unless you leave that base layer within about 6 months, you will experience burnout due to the sheer joylessness of the grind of that level of the game. To get to the next level you need to focus on free cash flow.

As an indie consultant, you are primarily an investor in yourself, and the best principle for making this investment is the venture-capital principle of cash and control. The more you have a strong, liquid cash position, and control over your life, the easier it becomes to be strategic and rational about pricing your services right and saying yes or no to gigs based on considerations other than rent-panic levels.

At this level, you’re basically learning to just run your indie consulting life as a business, and acquire and refine basic instincts around pricing, supply and demand for your services, and negotiations, all driven by an understanding of your own needs, lifestyle costs, and operating margins.

Here are 3 posts where I’ve explored aspects of this.

1. Knowing Which Nut to Tighten: Consulting, the principal-agent problem, how the knowledge economy shapes gig work, and how companies manage the risks of working with consultants.

2. When is a Gig an Engagement? (public): The difference between contractors and consultants, why it is valuable to be perceived as the latter, and how haggling over prices affects that perception. Plus an exploration of transactional, quasi-social, and intimate zones of gig-work.

3. Making it Interesting: An exploration of how to keep gig work interesting, using the price to partner, raise to risk approach to pricing your services, and resisting the temptation to price yourself too high or too low to attract interesting work. All explored in conversation over a cup of coffee with Bernie Anscombe of the Anscombe consulting clan.

Learning Flywheel Level

If you get stuck at the free-cash flow level, and never get beyond solving for maximum money with minimum time investment, and maximal cash-and-control — this is the basic flaw of the 4-hour-workweek libertarian fuck-you-money approach — you will burn out in about 2 years. To last longer, you have to discover who you are, by doubling down on things you like to learn, while working on gigs.

It’s a bad mistake to separate your learning interests from your working interests. That’s a recipe for eventually hating your work, thinking of it as just a way to pay the bills and fund your fun, and an activity that you’d rather make “passive” and get yourself out of. It rarely works.

In other words, once you have a robust dealflow going, and enough cash and control to actually be able to run your indie consulting life as a sustainable business in non-panic mode, you can start saying yes and no more thoughtfully to opportunities, and start spinning up your unique learning flywheel within your gigwork.

At the learning flywheel level, you should strive to say yes to gigs where you’ll learn more of what you want to learn, and no to gigs where you won’t.

It’s as simple as that.

And it’s the opposite of passive income. This is as active as income gets. You’re not looking for shortcuts. You’re looking to make the long way the fun way.

Why? Because at this point, you are solving the problem of figuring out who you are. This is effectively indistinguishable from what you’re learning the fastest, which in turn is almost entirely a function of what behaviors you are repeating most frequently and enjoying in your gigs. In other words, iteration rate of mindful deliberate practice.

Finding and staying in the maximal iteration/learning rate zone of what you enjoy is a pretty subtle challenge. It took me nearly 3 years to figure out that it was “conversational sparring” for me. You have to scope your gigs right, have lots of the right kind of conversation, and be very productive in the right kind of deliverable medium.

Here are some posts exploring these matters.

1. Maneuvers vs. Melees (public): An application of the military concepts of maneuvering versus melee warfare to consulting, mapping sales and finance functions to the latter, and everything else to the former, and a discussion of how and why this matters in indie consulting. This issue featured the return of Arnie Anscombe.

2. The 12 Eigenconversations: An exploration of the 12 basic types of conversations you can have in consulting work. The post introduces my elusive and shadowy older brother Mycroft Rao, who I turn to when I’m stuck. Also featuring Arnie Anscombe.

3. The Shtickbox Affair: The dangers of building your consulting life around shticks, both to you as an indie consultant, and to your clients. Explored via a mysterious case featuring Agent Jopp of the FBI G-Crimes division and my frenemy Guanxi Gao.

4. The Medium is the Client: An application of the “medium is the message” principle to consulting work, and how the medium of delivery for your services strongly shapes how you and your clients perceive each other, and how it can affect the structure of mutual expectations and compensation. All explored through the lens of a mystery featuring a corpse, 4 consultant suspects, and Agent Lestrode of the FBI G-Crimes division.

5. Elements of Consulting Style (public): A discussion of 4 basic styles of consulting: Explorer, Integrator, Tester, Achiever, using a 2×2 framework of inner versus outer, confidence versus doubt.

Value Theory Level

Believe it or not — and this is heresy to doerists — a life of pure learning and new personal records is not satisfying. If you get stuck at the learning level, you will burn out in about 3 years, or about as long as the average consulting shtick lasts before people get tired of it. To survive longer, you have to explore how you create value for others.

Once you have a sense of confidence in who you are, through success in your learning efforts and a stably spinning flywheel, you can start to expand your horizons. You can look at your role in the world of work critically, and ask what am I doing here in a relatively disinterested way, without being insecurely attached to your hard-won skills.

When you’ve bootstrapped this level of mindful ongoing interrogation of your working life, you will be able to more readily see the world from the point of view of your clients, critically interrogate your own evolving identity, and become aware of your blindspots, rationalizations, and limiting self-perceptions.

It is necessary to have established this ongoing interrogative process, as a set of habits, before you can ask meaningfully the question how do I actually create or add value? If you ask it too early, you will only find ritualistic, self-serving answers.

1. Response Regimes in Indie Consulting (public): An exploration of how consultants help organizations generate non-routine responses to situations, via a 2×2 risk-versus-urgency model of 4 response regimes: strategy, first-response, preventive care, and surge capacity. As a bonus, crossing this with the 2×2 model in Elements of Consulting Style, we get a schema of 16 styles of consulting.

2. You Are Not a Scientist: A brief exploration of the dangers of imagining that the work you do is “scientific”, and an exploration of 4 modes of consulting knowledge: simulation, fiction, thick description, and science. On a 2×2 of course!

3. Always Be Strategizing: The importance of making sure whatever you do has strategic relevance, and developing a sixth sense for when that is happening, and the relationship to expectations structures. All seen through the lens of a critical conversation about the parable of the three stonecutters and a device known as the strategometer.

4. The Clutch Class: A Labor Day special post, arguing that indie consultants and free agents are best understood as scabs in relation to the labor movement, and why that is both a good thing under modern economic conditions, and a perception to own rather than apologize for.

Growth Story Level

If you get stuck at the value level, you will last perhaps 5 years before you burn out due to either extreme idealism or extreme cynicism.

Unfortunately, a clear-eyed questioning of whether you’re adding value will often yield the answer, no. And you can get sucked in from there into perennial agonizing and fine-tuning of your work, in an attempt to find a Grand Unified Theory of Guaranteed Value Addition.

This is a utopian trap. You’re actually doing far better than average if you can claim that you are adding value in 1 out of 2 gigs. A more typical rate I suspect is 1 in 5 (below that, you’ll likely feel like you’re participating in a bullshit-work economy).

The corresponding dystopian trap is coming to believe that nothing can ever get better, and slowly succumbing to temptations to fraud, bad-faith, and corruption.

The growth story level is about making your peace with the best effectiveness of impact you are able to generate, without falling victim to either utopian idealism or dystopian cynicism.

One of the reasons many indie consultants fail to do this and get trapped at the value theory level is that they fail to distinguish learning (one level below) from growth (one level above). They think the value theory level is the top of the pyramid.

Learning is a matter of disciplined curiosity, conscious cultivation of knowledge and skills, and strategic choice of gigs. You can learn without really growing, and many people do just that. That’s how you get trapped in shticks.

You can also learn within a fixed theory of value addition, and grow complacent within a fixed sense of your own worth. That’s how you become part of a faddish trend. A fad is basically an uncritical, fixed, widely-shared value theory that only dies when it starts to fail miserably, triggering utopian or dystopian yearnings and behaviors.

Growth is the result of integrating your experiences, figuring out what they mean, healing any scars, and evolving beyond them. This means reflecting on what happens to you and to the world around you, as a result of you doing what you do, and extracting the right lessons. How do you know when the lessons are the right ones? When they point the way to continuing the game in the most interesting way possible, instead of adding more details to the map of whatever “value-addition theory” rut you are in.

This is a storytelling task. You have to repeatedly tell both your own story, and the story of your environment, at all scales, in order to maintain a constant, live sense of how you’re part of a bigger story. Writing this newsletter is part of my own attempt to address my own current growth needs.

Here are 4 posts to help you do the same.

1. The Shadow’s Journey: Exploring the psychological role of the indie consultant as a shadow, and the importance of origin stories (as opposed to resumes and titles) for indie consultants.

2. The Two Shadows of the Hero: Playing detective to diagnose what’s going on in an organization, sorting out the effects of malice versus stupidity, and the relative merits of investigating a situation through reasoning versus watercooler gossip and grapevine data. All through the lens of the Bermuda Triangle Case. This post introduced the FBI G-Crimes division, Agents Lestrode and Jopp, reintroduced my frenemy Guanxi Gao.

3. A Tale of Two Schools: A survey of the structure of the consulting industry, the people school vs. positioning school divide within it, the core playbooks of the two schools, and how indie consulting fits within a landscape dominated by larger positioning-school firms.

4. The Secret History of Consulting: 1: The first of a 3-part Big History of consulting. In this part, I cover the pre-modern era, from antiquity to about 1453. Future parts will cover early modern (1453-1945) and modern (1945-today) eras. The goal of this series is to help you situate your work within a tradition of work that is as rich and long as traditional employment, entrepreneurship, or just being born wealthy.

So that’s where we are now, 25 posts in. Next week, I’ll shift gears a bit, and start exploring Fall themes. We’ll see how that goes.