Month: October 2019

What should your self-image as a consultant be? Take a moment to pick an option on this Twitter poll before reading further.

There are others, but these are the most common self-images I see in people entering the indie consulting game. Each self-image induces a certain kind of structure to replace the structure you’re leaving behind.

Which is the right answer?

Paycheckier Than Thou

In the spirit of Halloween: this is a trick question, and all these answers are wrong.

There is a right answer, but first let me explain why your answer is wrong.

Your answer is wrong because each answer is basically an ersatz version of a non-indie consultant: a paycheck employee of an established, brand-name industrial-era consulting firm.

If that’s all indie consulting is — offering ersatz versions of services offered by consulting firms, for less money, and at smaller scale — then it is basically not worth doing. You may make money, but you likely won’t be fulfilled. You’ll always feel like a second-class citizen in a game pioneered by others, that they’re better at. A cheaper knock-off of a major brand.

There is a place in the consulting economy for the things non-indie consultants do, and for the brand-name consulting firms that employ them, but it’s not your role. It’s not your game.

So why do we gravitate to these self-images? Because uncritical imitation is easier than thinking about your own situation. That plus availability bias of real people to imitate. And the fact that they are familiar images to project to clients, making for easy (if not particularly effective) marketing and sales strategies.

The last few decades, from the 1970s to the early 2000s, were something of an aberration in the history of consulting, in that the craft became highly stylized, corporatized, and dominated by the non-independent kind of consultant. Consultants who were employees of larger consulting companies who aggregated talent capable of delivering against a particular codified consulting playbook.

Not only were typical consultants paycheck types, they were more paychecky than ordinary paycheck types, not less.

Despite a superficial branding of bad-ass mercenary guile, rank-and-file employee consultants were, by and large, the truest Organization Men, taking on less career risk in general than employees, not more. Employee-consulting in a large, established consulting firm is often a safer line of work than regular paycheck jobs, not riskier. If you get fired or laid off from a consulting firm job, you have more options open to you, in more industries, than a regular laid-off employee.

Cynicism about flavor-of-the-month business fads is for client employees. Non-indie consultants are usually true believers not only in whatever kool-aid they sell, but in the general idea of the industrial corporation as a model for organizing work. They are Extreme Organization Men (and Women).

As Upton Sinclair observed, “It is difficult to get a man to understand something when his salary depends upon his not understanding it.”

When your salary depends upon not understanding that you’re selling kool-aid, and that the cynicism on the other end is justified, you will work hard to not understand it.

The ordinary paycheck employee merely suffered through the latest flavor of the month, finding solace in watercooler grousing and Dilbert strips. The sociopath CEOs and the partner-level consultants selling them services merely practiced the age-old art of collaborative cronyist ruling from the top.

But the rank-and-file consultants actually delivering the goods? Everything from workshops in coding katas or design thinking to brand-narrative studies and heavy-lift spreadsheet models?

They believed. They had to. Their livelihoods depended on it.

What’s more, not only did they believe, they thought they were part of a more enlightened breed, tasked with raising the consciousness of cynical and apathetic regular employees with their wisdom. They thought their kool-aid was red pills.

Red pills for a particular subset of traditional employees.

Each of the four self-images in the poll represents an archetype that is symbiotic with a class of roles within traditional organizations. There are 4 such classes, giving us 4 True Believer paycheckier-than-thou non-indie consultant types.

True Believer Non-Indie Consultants

The industrial age corporation comprises four types of employees, each served by its non-indie consultant symbiote type.

• Rank-and-file workers, served by martial artist trainer types

• Staff management, served by pattern-language maven types

• Executive leadership, served by storyteller/bard types

• Line management, served by no-bullshit grinder types

Notably, very little of the actual playbook-deliverable work is done by senior-partner-level people in consulting firms who do take on non-employee type risks.

Let’s take these 4 in turn. Don’t forget: these are NON-indie consulting archetypes. They are paycheckier-than-thou Extreme Organization Men.

1. The martial artist trainer self-image was pioneered by productivity/efficiency focused consulting companies that supported training programs for skilled rank-and-file employees. Things like lean six-sigma, agile programming, and so forth. Programmers seeking philosophical inspiration often naturally turn to Asian martial arts because they feed a nerdy OCD approach to personal growth. They try to map martial arts concepts like shuhari, and kihon-kata-kumite to the problem of becoming more technically proficient. Consulting firms operating in this market gleefully co-opt this tendency in offerings like lean six-sigma with its “belt” system or “coding katas” used by agile programming trainers. Participation in such offerings feels like fandom to clients.

2. The pattern-language maven self-image was pioneered by design consulting firms (many drawing inspiration from the work of architectural thinkers like Christopher Alexander) that pandered to the vanities of aesthetes and wannabe autocrats seeking comprehensive “systems” for running little empires. Often, the target kind of client for such firms is people in staff roles without too much direct power over P&Ls. Such people are often in denial about their lack of real agency relative to line management, and eagerly latch on to any “system” that allows them to produce and consume process makework with combinatorial efficiency. A dead giveaway or tell is the production of stylized collateral information artifacts for their own sake. Participation in such offerings feels like cultural/art production to clients.

3. The storyteller/bard self-image was pioneered by marketing and advertising firms in the Good Old Days when powerful agencies of record led by Mad Men managed powerful brands and huge broadcast media budgets, farming out vast cascades of work in everything from graphic design to video production. The target was often vain senior executives in a mood to buy self-serving narratives which would offer them starring roles, and a delusion of more authorship over events than they actually had, while helping manage the optics of whatever universe-denting they were pretending to do. Often this kind of aspirational self-deception evolves in parallel with cynical stock price manipulation to maximize the value of their own compensation. Participation in such offerings feels like history-making or theatrical production of quasi-historical narrative — often both at once — to clients.

4. The no-bullshit grinder self-image is the most familiar of the four, and was pioneered by the Big 3 strategy consulting firms, who made the archetypal modern consultant a familiar figure: putting in 100 hour weeks, logging hundreds of thousands of frequent flyer miles, living out of hotels and weekend apartments. The calling card of this breed was the wonky spreadsheet, with which they “got real,” typically with the P & L line management types. Participation in such offerings often feels like martyred “real” work to clients.

What is common to all 4 breeds is that they are paycheck employees who:

1. Log billable hours but are protected from revenue volatility

2. Often work far harder than employees at the companies they serve

3. Are true believers in whatever playbook they’re running

4. Believe they’re enlightened cynics who see reality more clearly than clients

5. Believe more strongly in the roles they serve than the people occupying them

6. Aestheticize an area of work in ways that flatter the self-images of clients

This is why I call them paycheckier-than-thou. All four are terrible archetypes to model your indie consulting career on.

The Right Answer

I don’t want to be too hard on these archetypes. The playbooks they run offer a LOT of good raw material for indie consultants.

You can, and should, liberally steal from, and adapt, all 4 kinds of True Believer paycheckier-than-thou playbooks. You should mix-and-match gleefully. You should use their techniques the way guerrillas use the weapons they steal from the the larger conventional armies they go up against.

I do this liberally, stealing from all 4 sources all the time.

But what you shouldn’t do is adopt the associated self-images or associated overarching playbooks.

As an indie consultant, your situation is the opposite one from non-indie consultant types. Your livelihood depends on understanding what the non-independent consulting industry, in the form of larger firms, actually does. That’s the only way you’ll find a guerrilla niche for yourself in the landscape they’ve carved out.

Non-indie consultant self-images are liabilities for independent consulting. Your logged hours represent real money. Your attachment to every client rests entirely on the value of the last valuable thing you did for them. You cannot hide within the nebulous value proposition of a million-dollar “engagement” between two corporations. Your contributions (or lack thereof) cannot be safely hidden within the work of a large team.

For the non-indie consultant, there is no difference between running a playbook and making a difference. For the indie consultant, there is all the difference in the world.

Believing in any kind of kool-aid is an existential risk for you, even though it is a crucial enabler for some breed of non-indie consultant.

• To the extent indie consulting is like martial arts training, it is closer to supporting someone as a wingman in a street fight than coaching them in a stylized dojo. You’re not Yoda, you’re Han Solo.

• To the extent indie consulting is a pattern language, it is a jury-rigged library of cheap tricks collected from all over the place rather than a systematic aesthetic theory. You’re not Christopher Alexander, you’re a dumpster diver.

• To the extent indie consulting is about storytelling, it is a shredded pile of narrative fragments, lending structure to moments of clarity in chaos rather than producing epics. You’re not Walter Isaacson, you’re a stand-up comic.

• To the extent indie consulting is about no-bullshit grinding, it is about finding and doing the few hours of work that actually matter, buried in the 100-hour makework-week. You’re not Ray Donovan, but neither are you Tim Ferris, solving for 4 work hours. You’re a mystery-solving detective, putting in the hours actually needed to solve the case correctly. Sometimes that’s a 100-hour work week, sometimes it’s a 4 hour work week (and it’s never a straight line from interviews to spreadsheets to powerpoints).

If you don’t like these operating conditions, you shouldn’t be operating as an indie consultant. It is too real for you. You should be an employee in a larger firm (at least 10-15 people) where somebody else does the anxiety-inducing stuff for which there is no playbook.

But if you like the sound of this, when you put these dispositions together, you get only one answer: the indie consultant is a trickster, cobbling together bits and pieces in ongoing improvisation, sometimes sublime and inspired, sometimes just buying you enough time to dream up the next hack.

The indie consultant life is an endless Halloween, a string of trick-or-treat encounters with clients who generously play along, where the only thing keeping you philosophically honest is the fact that you have to live with yourself, with no playbooks or Senior Partners to blame for your failures.

And the goal of the trickery is to fool yourself and the client just long enough to accidentally do something right. And doing it despite instinctive attraction to stylized bullshit of one sort or the other operating on both sides of the table.

And if you’re lucky, maybe some of the tricks will be treats too.

With this issue, we conclude our 5-part series on leaping into the gig economy, and put it all together with a preparation roadmap. This part can be read stand-alone, though you’ll get a lot more out of it if you’ve been following the whole series.

Timing the Leap

Based on everything I’ve said so far in this series, about the first leap, leap risk, minimum viable cunning, and the inner game of gigwork, you might be tempted to conclude you should look at the preparation work you have to do, and then plan to leap in N years, where N is a function of how much preparation you think you need.

No. This is exactly backwards. It’s Soviet 5-year plan thinking. It’s corporate employee “career ladder” thinking. You’re not trying to “put in the time” to “earn” a desirable title or position like a corporate lifer. You’re trying to craft an escape to free agency.

Illogical though it might sound, you have to pick a date or leap event (such as a certain critical meeting going a certain way), and then do the best job of preparation you can before that. The rest will have to be done under live-fire conditions after the leap.

Why?

Because preparedness is actually the least important of 4 major factors that should influence the timing. It just happens to be the one you have most control over.

The factors driving the timing of your leap are: Preparedness, Risk Appetite, Opportunity, and Depressors. You can remember this with the convenient acronym PROD.

1. Preparedness is actually the least important of the four, but the only one you can actually do something about. So there is a temptation to let it drive the timing exclusively. I’ve written 4 posts about preparation, but that doesn’t mean it’s the most important factor in timing. I was very well-prepared personally, but that’s just because my preparation needs happened to line up well with the right timing.

2. Risk appetite, in my experience, does not change much for people, barring seriously traumatic events (which in most cases reduces risk appetite rather than increasing it). But while you can’t change this, you can “trick” your risk appetite in ways I’ll outline in the next section. I’m personally very risk averse in terms of financial and entrepreneurial risk, so I had to trick myself quite strongly.

3. Opportunity is the second most important factor, but the one least within your control. Y2K was a good example. It launched many companies and careers within a tight launch window. You can create small, local opportunities around yourself by taking the initiative, but the biggest tailwinds will generally be in the environment. You have to be alive to them. My opportunity was of course, the brief window of opportunity when blogs ruled the internet.

4. Depressors are the single most important factor. If you are in a situation you hate, doing work you dislike, with people you detest, in an industry you think is toxic and dying, everyday life becomes a special kind of hell, and you die a little more ever day you stay there. If this applies to you (fortunately, it didn’t apply to me), leap as soon as humanly possible, before you get reduced to subhuman gloom, and there’s not enough of you left to save.

So remember the acronym PROD: preparedness, risk appetite, opportunity, depressors. We’ve talked a lot about the first element in this series.

The last two are very situation specific, so I don’t have much to say about the opportunities and depressors in your specific environment. If I had the bandwidth to offer 1:1 coaching, which I don’t, this is what I’d spend a lot of time on. But if you can find a friendly neighborhood gigworker who has already made the leap, you may want to seek out mentorship from them on opportunities and depressors.

The second element, risk-appetite, is something we can say a few general things about.

Hacking Risk Appetite

PROD gets at the logical, analytical side of timing the leap, but there’s also a gut-level intuitive side to the timing, which involves hacking your risk appetite to accept the right level of risk rather than imposing the level of risk it is comfortable with on your conscious thought. Yeah, this is a mind-over-gut programming operation. Like messing with your gut microbiome with weird supplements, except via memetic microfauna that live there.

And you must hack your risk appetite, otherwise it will trigger harmful stress responses that prevent you from managing the eminently manageable risks. You don’t want to thrash and drown in 2 feet of water simply because you can’t swim. Controlling your panic response will reveal the solution to be very simple: you don’t need to learn to swim in 5 minutes. You just need to stand up.

There’s two versions of risk-appetite hacking problems. Too much risk appetite (uncommon), and too little (much more common).

Generally, too much risk appetite leads to leaping too early, and too little leads to leaping too late. But occasionally you see the reverse. Too much risk appetite leading to waiting too long (for the “big score” opportunity) and too little leading to leaping too early (because there’s a less scary thing you can do now that’s easier than waiting for the window of opportunity to do the more scary thing).

But you don’t want to be too early or too late. You want to time it just right. Don’t underestimate the deep sense of power that comes from feeling in your gut that you’re leaping at the right moment. Here’s a famous dose of Shakespeare you should commit to memory:

There is a tide in the affairs of men.
Which, taken at the flood, leads on to fortune;
Omitted, all the voyage of their life
Is bound in shallows and in miseries.
On such a full sea are we now afloat,
And we must take the current when it serves,
Or lose our ventures.

The more time you have available, the more (and more effectively) you can prepare — up to a point. Beyond that point, more preparation is actually fear. It might be valuable, but the value will be lower than the opportunity cost in missed opportunities, toll exacted by continuing in depressing situations, and not hacking your gut to take better risks. Here’s a second dose of Shakespeare you should commit to memory:

…Art thou afeard
To be the same in thine own act and valor
As thou art in desire? Wouldst thou have that
Which thou esteem’st the ornament of life,
And live a coward in thine own esteem,
Letting “I dare not” wait upon “I would, ”
Like the poor cat i’ th’ adage?

These two verses, interestingly, are spoken by Brutus and Lady Macbeth, the villains of Julius Caesar and Macbeth respectively. The kind of boldness it takes to navigate your first leap is actually the same kind of boldness it takes to commit murder. Except in this case, the victim is your old low-agency, unhappy self, rather than another person. You’ll still be unhappy (happiness is overrated), but it will be an interesting new kind of high-agency unhappiness that you’ll actually enjoy mastering. If only because you’ll only have yourself to blame with pointy-haired bosses and toxic coworkers out of the equation.

Your first leap is an ego death triggered by out-of-comfort-zone risk-taking, followed by regeneration into a fuller life. You know in your gut you must leap, because to not do so would be to resign yourself to a slow death.

Once you’ve truly committed in your gut, you will find that waiting is almost intolerable, and you will naturally, try to advance the timing. The risk of mistiming the leap will shift polarity. Where you previously risked procrastinating till its too late, you will now risk leaping too soon because the stress of waiting is too much (kinda like how nervous soldiers might fire before “seeing the whites of their eyes”). Shakespeare one more time, again from Julius Caesar.

Between the acting of a dreadful thing
And the first motion, all the interim is
Like a phantasm or a hideous dream.
The genius and the mortal instruments
Are then in council, and the state of a man,
Like to a little kingdom, suffers then
The nature of an insurrection.

The point of developing an awareness of this gut-level aspect is not to change your risk appetite, but to hack it. That element of PROD, like I said, is not easy to change. The point is to develop your capacity to leap despite the risk being outside your tolerance range, and the prospect of fear being greater than you think you can handle.

Hacking risk appetite so you take on the right level of risk, rather than the level that feels comfortable, is a bit like dieting. You have to commit irreversibly to a risk level before the actual fear kicks in, and then short-circuit the ability of your appetite to do anything about it.

It’s like deciding to eat a salad for lunch, and locking in that commitment by throwing away the cake and chips.

Caesar burning bridges and Cortez burning boats are among many famous examples of leaders hacking risk appetite, but you have to go beyond resonating with such allegories to crafting literal irreversible commitment moves for yourself.

In my case, a big part of hacking my risk appetite was getting very small cash-flows going. They were barely better than nothing in terms of actually sustaining my life financially, but they made a huge difference psychologically, as proof that I could make money flow without help from an employer. Apparently my gut can’t count, and doesn’t know the difference between $100 and $1000. I exploited that.

How do you know when you’ve hacked your risk appetite into submission?

You’ve heard how entrepreneurs have to go from a logical Ready, Aim, Fire to an illogical Ready, Fire, Aim operating condition. Hacking risk appetite takes the illogic one step further. Your first leap is almost certainly going to be a case of Fire, Aim, Ready.

If you’ve hacked your risk appetite right, and worked on PROD as much as you can, it should feel like you’re making the irreversible commitment before you’ve figured out a direction, and picked a direction and started moving before you’re actually ready to sustain movement.

It feels unnatural, but that’s a good (though not definitive) sign you’re doing it right.

Fire, Aim, Ready

So you’ve picked your leap date or event, and it’s N years out, or perhaps it’s in the past: you’ve already leaped, underprepared. But no matter what N is for you, it’s likely going to be a fire-aim-ready script.

The question now is, how much preparation can you cram into what time you have between fire and ready (which is possibly negative). Here’s a rough breakdown, illustrated in the drawing.

N < 0: You’re in preparation debt zone. You’ve leaped and are not ready. Get active on Twitter. Create an interesting deck around a topic of expertise, and see if you can line up talks at meetups and conferences (simply attending and “networking” is very low value). Make money by any means possible. Drive Lyft. Get a low-status temp job that seems beneath you if you must (but commit to quitting asap). Save money by any means possible, borrow if you must (and can). N<0 is an emergency response regime, and you will do most of this naturally because it is obvious. Your actions aren’t going to be very leveraged or strategic. You’re in band-aid territory. But getting out of the emergency state is less obvious and natural. It is surprisingly easy to adapt to, and stay in, this crappy temporizing zone far longer than you should. Your goal here is to start aggressively buying time so you can actually catch up on preparation work that should have been done before the leap. Preparation debt is not a good state to be in, and your survival chances are weakest, but it’s not necessarily fatal. And it can be a better state to be in than in a soul-killing job.

0 < P < 1: You’re in launch ramp zone. Count the number of friends outside your work you interact with regularly outside of work, and increase that. They will be more valuable in the short term than shallow “networking” contacts or current at-work colleagues (who may feel betrayed and not inclined to help when you leave). Double or triple your investment in outside high-frequency friendships. If you’re in a line of work that allows for creating outside-of-work artifacts, identify a small warm-up pregig, like a pro bono project for a nonprofit, a contribution to an open source project. And most importantly, ramp up your performance at work. Exiting on a high note rather than as a lame duck creates a LOT of positive externalities. And of course, start saving aggressively, on a war footing. 

1 < P < 3: You’re in asset-building zone. Between 1 and 3 years, you have enough time to build a meaningful asset like a blog, email newsletter, book, or side project from a cold start. Not only should you build an asset, you should have turned it on at a test level, and had some validated success with it. Also: get on a steady savings ramp. Not in an illiquid form like a retirement account or a house, but in a form that can be rapidly liquidated. And these savings have to be above and beyond emergency savings (which for most employed people tends to be 1-3 months, so think in terms of 6 months out).

3 < P < 5: You’re in portfolio-building zone. Between 3 and 5 years, you have enough time to build more than one asset. When I jumped ship, I had been developing the option for 4 years. Besides my main blog, ribbonfarm, I had a book almost ready to go, and a strong following on Quora. Try and make these different kinds of realizable options. A book, once launched (especially if self-published) can instantly create a spike of revenue. In this planning range, your savings behavior still has to be slightly different (more loaded on liquid assets than people who intend to stay employed)

5 < years: Beyond 5 years, we are in mindset-preparedness zone. The behaviors include: reading outside your sector, reading management and self-management books, and approaching your job with a very different mindset than the people who expect to stay in paycheck employment their whole careers. Preparing for the option of leaping into the gig economy might actually make you better at your job, ironically (it serves as a BATNA that increases your risk-taking at your job, leading to better results since most employees take too little internal risk).

Training Zone: If you’re in college or high-school, and the clock hasn’t started ticking yet, you’re in the training zone. If you’re aware that the future is giggy, you will approach your educational options differently, try and learn different skills than if you were preparing for a paycheck career in a series of jobs.

Contrarian view: if you’re in education, I don’t think it’s a good idea to dive right into the gig economy. If you can, spend some time in a paycheck world while it still exists. Gig work still uses all the same skills as paycheck work, so you might as well learn those skills on someone else’s dime.

In Conclusion

Here’s the big boring secret about the gig economy. Though it is still a small fraction of the labor market (I’d estimate about 20-25% in the US), everybody is likely to cycle through it at some point, at least for a while. So there’s nothing particularly special about being in the gig economy. The difference isn’t between people who are/will be in it versus not, but between people who are happier in it versus not.

Yet almost nobody prepares for it, intellectually, financially, emotionally, or educationally. Weird, huh?

But despite the fact that it will touch almost everybody’s life in the future, it is somewhat magical: the gig economy exists only to the extent you believe in it. It is like an economic equivalent of the Room of Requirement in Harry Potter. You have to kinda believe it is out there and that it will appear around you when you need it.

Actually, the paycheck employment economy also only exists because we believe in it enough to jump into it, without guarantees or certainties that there’s a there there for us to land when we head out interviewing.

The only difference is that the paycheck economy comes with a lot of highly visible social proof props called “companies” that make belief easier, by building a concrete landscape of offices with reception desks, equipment, badges, and uniforms. Believing in the paycheck economy is like suspending disbelief enough to watch a movie. Believing in the gig economy is like suspending disbelief enough to read a book. You have to construct your own mental imagery to make it real.

All economics is self-fulfilling prophecies. Stuff that happens because people believe it can. When an economic sector dries up, all of it can turn into a ghost town overnight. Whether it is populated by gig-workers in cafes, or employees with badges in offices, makes no difference. The cafes empty out and close down. The offices empty out and close down. For Sale signs go up. Tumbleweed blows in the wind. Zombies appear and stagger about.

Gigwork or paycheck work, we all live in the same economy. The only difference is how we manage our exposure to the risks of living inside the collective fictions of economic modernity, sustained by the circulation of these little green fictions we call money.

To leap into the gig economy is to leap into a state of belief that does not require all the props. It is a state of belief that draws directly from the raw, collective élan vital of homo economicus, trusting in your fellow human beings to create the demand for whatever it is you might be capable of supplying. It is the opposite of a fuck-you-money flouncing out of the economy. It is something like a trust fall into the waiting hands of unknown people who you are going to believe in, and who are going to believe in you, so you can invent your own future.

And that’s it for our extended look at your first leap.

We’ll switch gears next week to a different focus, heading into winter.

In the last 3 weeks, we’ve explored the anatomy of your first leap into the gig economy, understanding leap risk, and mitigating that risk with minimum viable cunning. Together, these topics cover what you might call the outer game of gigwork. The practical stuff.

Continuing this 101 series, this time, I want to tackle what I think of as the inner game of gigwork. The even more practical stuff. The inner work you need to do to ensure your new life is a more enriching, high-agency life that allows you to be more fully human than the life you’re leaving (or contemplating leaving) behind. Ironically, the key to doing this is seeing yourself as more of a robot.

You, Robot

If a job is a simple plastic mask that hides the “real you” that comes out on evenings and weekends, a gigwork identity is an entire robot suit that allows you to express the real you. Lifestyle design is robot design.

Weird, huh? It’s the paradox of the inner game.

The more you can get comfortable in a robotic skin (for a precise sense of robotic that I’ll get to), the more human you can be. The more you resist and hold on to an egoistic sense of your own humanity, the more you’ll be reduced by circumstances to a low-agency Sturm und Drang precious-snowflake zombie controlled by the environment. In the economic outer space that is the gig economy, your robot suit is also a space suit that allows you to survive. Your choice of personas, on the surface, can seem like it’s between being a human non-playable character (NPC) or a high-agency robot character.

The key to unraveling the paradox is understanding that in the paycheck economy you’re already a robot. In the gig economy, you just have to own that fact. And if you own it well, you’ll appear more intensely human to others, the opposite of robotic.

In the gig economy, you’re just insourcing a lot of the robotic aspects of your being that were previously embedded in your workplace environment, and now have to be part of your life environment. In both cases, what they do is create a container for your squishy, messy, human psyche.

In the process of in-sourcing, you’ll be personalizing and customizing to yourself, so you’ll be more free to express yourself. Recognizing this is what dissolves the paradox.

To extend our robots-spacesuits analogy, paycheck employees are also robots. They just don’t realize it because their robot suit is a large shared spaceship containing a lot of people in a single life-support environmental system. The interior fosters an illusion of greater humanity than they actually possess. Being in a robot space-suit outside simply brings that reality so close to you, the illusion breaks. But your space-suit is still more human-shaped than the spaceship.

Inner Game vs. Outer Game

The title of this post, btw, is a hat-tip to an excellent book, Timothy Gallway’s Inner Game of Tennis, which is not particularly directly relevant to our subject matter here, but is a generally good read on developing a creative mindset. It too has a curiously robot-design approach to its subject. Turns out, the key to getting into a zen-like mindset while playing tennis has to do with short-circuiting your ego so you can relate to yourself as a sensorimotor machine that learns and enacts physical behaviors in specific ways.

The inner game of gigwork is much simpler than the outer game, but much harder.

The outer game has a lot of messy and complicated details. A lot of logical puzzles to figure out, non-trivial budget arithmetic, and timing and strategy challenges to solve.

But if you’re moderately smart, none of it is actually hard, just tedious.

The math is not genius-level math. The chess-like strategy elements do not require grandmaster-level skill to work out and play out. The complicated details are more like Ikea furniture assembly than neurosurgery. And none of it requires extreme precision. So you can kinda half-ass a lot of it and figure it out as you go along.

The outer game is forgiving so long as you’re paying attention and thinking and willing to change what you’re doing as you learn.

The inner game though, despite being much simpler in terms of number of moving parts, is really hard. And it is less forgiving. If you manage your psyche wrong through a critical period, it might be the end.

The Case for Flying Blind

Preparing for the inner game is preparing for the evolution of your own psyche through the first few years as you ramp into the gig economy. It is predicting your own emotional reactions and preparing yourself to regulate them in helpful ways. You can’t tell how you’ll react to your first serious cashflow panic, but with the right inner-game disciplines in place, it is more likely to be a good reaction.

But before I outline that preparation process, I want to touch on the case for not preparing. Unlike the outer game, where underpreparation has clear risks and downsides, in the inner game, the benefits of preparing versus not preparing are less clear.

Why? The inner game is hard enough that you could argue the best way to tackle it is to not even realize how hard it is before diving in, and then working it all out under live fire conditions. Then you can look back and marvel at your own survival.

There’s a certain gonzo poetry to that kind of outcome: clueless newbies not knowing a problem is impossible according to more experienced people, and solving it anyway. It’s the stuff of legend.

This approach might even lead to better results sometimes. If you don’t read books about the gig economy or newsletters like this one, which try to prepare you for what you’re getting yourself into, you might pull off some inspired blank-sheet creativity.

That said, I do think survivorship bias in the narratives of these survivors tends to blind us to the fates of those who don’t make it, and perhaps might have with a little bit more conscious mental preparation.

So on balance, I think it is better to look ahead at what to expect for your inner journey. You might end up doing things a little less imaginatively, but you lower your risk of not making it. It’s a worthwhile trade-off.

A possible outcome of going through such mental self-preparation is that you might decide you’re not in fact, psychologically up to the challenge, reassess the true value of a paycheck job, and decide that’s a better fit for you after all.

And that’s okay. That’s great. The more you consciously choose the roles you’re cast into, the better you fit them. If the only thing I achieve through this 101 series is making some of you happier about your jobs and more content to stay in them, that would be a good outcome.

But a better outcome would be if more people left unsatisfying paycheck jobs for more satisfying gig economy careers, and did it well enough to make it.

Building Robot SELF-X

Setting up to play a good inner game is, like I said, not complicated. It’s just hard.

All of the inner game can be summarized as building a SELF-X system. Where X is any kind of primarily psychological support that used to be provided for you by coworkers, managers, or leaders in an employer organization (or in the case of fresh graduates, a university campus and parental support). SELF-X is also a nice name for a robot suit.

The inner game is doing for yourself all the psychological environment maintenance work X that used to be invisibly done for you.

I’m going to lay it out for you in the form of an inventory of inner-game competency areas (or in our allegory, robot design areas) to think about and figure out.

Get your expectations straight: You won’t figure it all out at once. You’ll iterate through approaches on all these fronts as your new life comes together via trial-and-error. Don’t be a perfectionist about any of this. Just pick a starting design, and iterate from there.

I’m going to use the context of a regular job to describe all the X’s, but if you’re a student who has not worked a full-time job before, just substitute the university or school environment equivalents.

Self-management

When you are in a job, you are unaware of the extent to which you rely on other people to manage you. You take and hand out action items, you sit in meetings run according to certain protocols, you take responsibility for certain processes and systems, and so on.

In the gig-economy have to learn self-management behaviors.

Jobs come with other-management philosophies that induce behavioral “code” that then runs to accomplish the work of the organization. Some workplaces are built around annual planning and goal-setting. Others are built around corporate habits like agile development. Still others navigate via mission statements and manifestos.

All vary in how much management they do (ranging from laissez-faire to micromanagement), but trust me, all of them manage you more than you realize, and you’ll feel the management vacuum hard on Day 1.

How do you approach self-management? Think of self-management as programming yourself like a robot. This does not mean you have to robotic in a stiff sense. You can be a gonzo robot like Bender on Futurama. You can be like one of those Boston Dynamics gymnast robots. You can be like a spunky little rover on Mars. But whatever your robot persona, it needs code to run. Code that used to come from others. If you don’t give yourself code to run, you’ll sit there doing nothing.

Seems obvious, but it’s amazing how many people think being your own boss equals not having a boss. You won’t magically be a better boss for yourself than other people were. There’s a good chance you’ll be worse at it. So you still have to learn how to be a good boss to yourself.

Self-structuring

This is subtly different. Most people need a certain amount of structure in their lives (you can take a test known as the California Personality Inventory that will give you a sense of how much structure you need) and when that falls apart, they don’t do well. So you have to build structure for yourself.

Like building deliberate awareness of which Starbucks locations seem to foster what kinds of work moods for you.

Like running experimental schedules to figure out whether you tend to work in 4 hour morning bursts or all-nighters.

Like choosing whether to stock up a nice home-office or rent a desk at a coworking space or live out of a backpack.

Like choosing a computer.

If you think your job is pretty flexible, think again. There are a thousand defaults that are set for you in any job. A job doesn’t have to be industrial 9-5 to serve as a strong forcing function on the structure of your work life.

How do you self-structure? Think of self-structuring as creating an operating system around yourself.

Code needs an operating environment to run in. But unlike the self-management behavioral code you write to run the foreground of your work, the operating environment code is more likely to be assembled from multiple other sources. Your task is that of architectural selection, not construction.

Though this might involve a lot of practical decisions like notebooks and computers and desks, they are primarily decisions that affect your inner mental state. That’s why they’re part of the inner game.

Self-direction

You not only have to be managed in a job, you have to be led, which is an entirely different thing. To be managed is to be given behavioral code to run, and an operating environment to run it in. Together, these determine how you work.

To be led is to be given direction and a motivation, a why. Things to do and a reason to care.

I like A. G. Lafley’s definition of leadership as “interpreting external reality for the organization”. This is not an objective, dispassionate description, but an opinionated, emotional understanding that makes a particular direction of movement seem inevitable and philosophically necessary, rather than merely logical.

And here’s the thing: psychologically, it doesn’t matter whether a leader is good or bad, whether their “interpretation of external reality” is a powerful vision or batshit insane, or whether their direction is taking the company to the moon or over a cliff.

The mere existence of ANY default interpretation of reality and direction of movement is enough to fill the need to be led. You’ll just march along. Perhaps reluctant and grumbling, but you’ll do it.

When you go free-agent, you’re on your own for this vectoring, and people tend to do badly without a sense of direction. They tend to stall entirely, and stop moving.

As a result, one compensatory response is that free agents often fixate on what I call “free and open-source public leaders”. Charlie Munger for instance, is the de facto CEO of thousands of free agents. So are Paul Graham and Naval Ravikant. In a previous era, when the gig economy had a distinctly feminine tone to it, due to the paycheck workplace being less friendly to women, Martha Stewart and Oprah Winfrey were the de facto CEOs for many women trying to run home-based businesses in the interstices of childcare and housework.

But admirable though such public leaders may be, they are not actually your leader!

The only lasting solution is for you to become your own leader. Your own CEO. You interpret your own reality, you set your own direction. Inspired or insane, your own direction is the only one you’ll be able to follow long-term.

Think of self-directing as making and maintaining your own maps, location awareness, and movement.

Don’t underestimate how hard it is. The easy part is drawing a map, and picking a logically coherent direction to go. The hard part is doing it in a way that you’ll actually care about going in that direction enough to take step after step, indefinitely.

Orientation is more than location awareness. It is motivation. The words motivation and motive indicate an urge to movement, not merely Google Maps directions.

Self-defining

In a job, who you are is determined by your job description and responsibilities. As a typical cynical employee, you might not care about titles and status beyond their being linked to compensation and perks and resume-stuffing for your next job. But even a title you’re cynical about molds your sense of self at an unconscious level. If you say enough times to people, I am Assistant Regional Manager at Dunder-Mifflin, it becomes your self-definition. The mask becomes the person. And one of the big effects is your sense of agency is shaped by your role.

In a gig economy, you have to do that for yourself. In my case, identifying as a “sparring partner” was an important early step. Self-definition is not the same as self-classification. Things like 2x2s and taxonomies might help you self-classify, but self-definition is sort of a declaration of who you are, and in particular, how you understand your own agency.

You’re your own boss. What do you give yourself permission to do? What rules that you used to follow in a paycheck job do you now break? What new rules do you now follow that you didn’t before?

In our robot allegory, self-definition is the act of constructing a permissions architecture around your own behaviors.

Think Asimov’s 3 Laws of Robotics. They aren’t “personal brands” or logos. But they strongly define the nature of Asimovian robots. What are the laws of You, Robot? What does “doing the right thing” mean to you? What does “doing the thing right” mean to you? That’s self-definition.

Self-ceremonializing

Another thing that organizations give you is a sense of ceremonial appearance. A way you appear to others in the context of work. This is again far more important than you might think.

So go ahead, order those business cards even if you have nobody to give them out to. Set up a website even if you have only uninspired boilerplate to put on it right now. Spend time cleaning up your LinkedIn. Have a friend take a couple of good headshots. Change your Twitter headline. Put your incorporation certificate up on the wall of your home office even though nobody will ever come by to check.

But don’t go overboard into absurdity. Don’t give yourself awards or silly titles even ironically. It’s a waste of mental energy, and drains seriousness.

The point of self-ceremonialization is to close a sensory-cues feedback loop to manage your psyche. Think of it as setting up mirrors all around yourself, not out of vanity, but to reinforce a way of being.

Some of this will happen naturally through self-structuring. An in-tray on your home office desk is both a ceremonial location for papers, and a cue to work on them. A Dilbert cartoon on a corkboard though, might not have any obvious cueing function for an instrumental behavior. It might just be an attitude set-point reminder, or a reminder of some philosophical principle. That’s part of the pure ceremony. The self-structured environment will get the work done, but it will likely not have the right emotional contours or signal the right priorities. Self-ceremonialization distorts the reality you inhabit in useful ways.

Think of it as taking the orienteering logic of self-direction, and the permissions architecture of self-definition, and using them to distort how the operating environment appears to you. Some things will loom larger, other things will shrink. Some things will be set up to be easier to do. Other things will be set up with guardrails to make them harder to do.

The point is to make your new life emotionally real for yourself, by setting up your own reality-distortion field. Think of self-ceremonializing as creating an effective UI for your new life.

Self-pacing

In a job, you have a reference pace, or workplace tempo. You define your own pace with reference to it. Do you go with the flow? Do you try to overtake others? Do you pace-set for others? Do you disrupt the flow?

But in the gig economy, there is no default reference stream of activity for you to define your own pace against. Think about it. When you start, perhaps you have one client in Silicon Valley going crazy fast, and another in a sleepy Midwestern town ambling along leisurely. Which one do you use as a reference?

Any simplistic reference-pacing will lead to schizophrenia. You have to look inwards to develop your own sense of pace, relative to your own life. You have to create a sort of time zone around yourself, just as ships out on the ocean have a “shipboard time” that is systematically set and reset as the ship sails across different longitudes.

How quickly do you respond to client emails?

What does it mean when you promise someone something “as soon as possible”.

What does “I’ll get to it this week” actually mean when you say it? Does it mean the same thing when you say it to different clients?

In our robot allegory, self-pacing is about sense-making in time via construction of an internal clock, now that you don’t have an external one from a workplace to drive you. It is actually another aspect of self-direction, the temporal dimension of leadership, but I like to break it out because it is a uniquely critical aspect.

The difference between armchair strategy and non-armchair live action often boils down to a ticking clock. The clock is the bridge between strategy and execution.

What is the right pace for the gig economy? It is almost always “faster than you are comfortable with”. The environment will tempt you to its own pace, and as you move across contexts, you might start behaving like a temporal chameleon, relaxing with relaxed clients, going neurotic with neurotic clients. This is the dark side of “being on the clock” in metering/billing terms. If your clock is no more than the sum of billing clocks in your various gigs, you’ve come temporally undone.

Don’t come temporally undone. Build an inner clock. Set your own pace with reference to the state of your own inner game.

One of the best ways to do this is to build up a compounding asset over time. Your internal clock is measurable by the runway you’ve laid out for yourself for that asset to gain value. For me, it’s been writing about business topics. It’s only a fraction of my writing, but it’s obvious when I’m not moving at a decent clip: I don’t have interesting new things to say on business topics. You could almost measure the pace of my consulting life by my rate of publishing decent business-related articles.

Self-Socializing

The final part of your inner game set-up is other people.

In a job, there are typically cultural structures in place to socialize you into a role, and keep you there, primarily via mediated interactions with other people. Happy hours, seminars etc. In the gig economy, you have to do this to yourself. Hell is always other people, but as a gig-worker you get to design your own hell. Make up a mix of social activities to suit your personality. Some mix of meetups, lunches with friends, and sessions at Starbucks should do the trick.

You have to set up the social structure and cultural rhythms you need to function. That much is easy and obvious.

The hard part of self-socializing is understanding how you depend on other people, who they are, and the extent to which they recognize the role they play in your new life, and then rearranging things if they seem to be unhealthy and limiting rather than healthy and enabling.

In a paycheck job, you don’t have much control over who’s in your socialization environment. In the gig economy you do.

You can more easily cut out people who drag you down, and add people who lift you up. But it doesn’t happen automatically. You have to exercise that capability to unlock a lot of the benefits of gigwork. But you’ll be tempted to add/subtract exactly the wrong sort of people, creating a self-defeating social environment for yourself.

In our robot allegory, self-socializing is architecting a network-identity for your environment.

Putting it Together

Let’s summarize. The inner game of gigwork is about constructing a robot suit for yourself, by insourcing things that used to be done for you, which help you manage your psyche as you figure out how to fend for yourself.

There are 7 basic areas of design to think about, as illustrated in the graphic at the top of this issue.

1. Self-Management: Learning to program yourself

2. Self-Structuring: Creating an operating environment

3. Self-Direction: Sense-making “space” (external reality) by making your own maps

4. Self-Defining: Architecting a permissions identity for yourself

5. Self-Ceremonializing: Creating a UI and packaging for your new life

6. Self-Pacing: Sense-making time by making an internal clock for yourself

7. Self-Socializing: Architecting a network identity for your social environment

This is a to-do list and a set of starter cues, with a hopefully helpful robot-suit allegory. I’m not going to tell you how to set up your inner game.

There’s a lot of good and bad advice for all of these areas of design focus out there. How you put your mindset together by putting these robotic parts together, and how you breathe life into it by putting it on, is actually your first big challenge in the gig economy.

There’s a holistic test for if it’s working though.

If you’ve designed your robot suit right, it should become almost invisible to both you and people who see you operating. You should feel a sense of freedom and control from the inside, and from the outside, exude a sense of intuitive agency. People may see you fumbling and stumbling. They may see you gracelessly working through trial-and-error experimentation. But they should get a sense that you know what you’re doing.

If your robot suit is visible (in the form of formulaic behaviors that mark you as as an easily identified “type” for instance, or as a “personal brand” robot that is put together with preternatural poise), it is a badly designed robot suit. Or the suit has become your master, like Doc. Ock’s AI arms in Spider-Man. Many free agents in the internet marketing world unfortunately come across as bad robots, their humanity subordinated to a bad inner game that has pwned them. They look like characters out of a sketch-comedy show rather than people. Parodies of themselves.

On the other hand, if you seem painfully all-too-human, but your behaviors seem whiny, overly vulnerable, and low-agency, you haven’t in-sourced enough of your psychological support environment yet. Like a starving artist who produces no art, but is very loudly human about it, playing the part of a sensitive soul being tossed about by a cruel world. No, that’s as bad as being a formulaic brand-bot. That is performative learned helplessness. That’s being a Sturm und Drang precious-snowflake zombie (I know I already said that, but I like that artistic slur so much, I had to repeat it ICYMI the first time).

Avoid both failure patterns. Get your inner game going right. Invisible suit, visible performance of real agency. Be a live player, not a dead player.

With this post, we’ve covered all the 101 content I wanted to in this series, but it feels like this could use some pulling together, so I’ll attempt a summary post next week, with suggestions for how to pull it all together without getting overwhelmed.

Let’s talk about cheats: unfair advantages and cheap tricks that, deployed with imagination and cunning, might mitigate a lot of the unavoidable unmanaged risk of leaping into the gig economy. I call these mechanisms cheats because they are not part of some general theory of systematic risk management. They are situational factors, likely unique to you, for making the leap in a particular place at a particular time. Your cheats come together in your particular pattern of what I call minimum viable cunning.

I’m going to discuss 4 common cheat cards that apply to most people, but you can and should think through and identify any uncommon cheats available to you as well.

Let’s recap a bit. We’re now into Part 3 of what promises to be at least a 5-part series on taking your first leap into the gig economy. If you’re already post-first-leap, some of this may be useful for your future leaps. But if it’s all old hat, bear with me. We’ll get back to the non-beginner stuff in a few more weeks.

In the first part, Your First Leap, I set the stage by distinguishing the leap into the gig economy from job searches and entrepreneurial ventures, and identifying common underpreparation mistakes that lead to a lot of people crashing and burning, and returning to the paycheck economy in a weakened state, scarred and scared out of the gig economy for life.

In the second part, Leap Risk, I walked you through an rough estimation process to get a sense of the risk of your leap, and how much of it is unmanaged. Roughly speaking, you can expect about 4 months of ramping to replace every $10,000 (or the equivalent in your country, if you’re not in the US) of fully loaded paycheck income, and optimistically, you can expect to make about half of your income during the ramping phase from gigs. In the example we worked out, a $60,000 annual income led to an estimated 36 months (3 years) of ramping to fully replace with gig-income, and an unmanaged risk estimate of about $100,000 during that period (which you can think of as an income gap you don’t yet know how you’ll fill).

We concluded that you’re unlikely to be able to close the risk gap purely through additional savings because it would take too much time. That’s why you need cheats, cunningly deployed. In fact, even if you could close the gap with money, you probably shouldn’t. Figuring out how to close risk gaps with cunning rather than money is essential early training in gig economy resourcefulness. Because remember: the gig economy is not a single leap, but repeated leaping.

You have to learn to be a goat. If you make it too easy on yourself, you’ll never learn the necessary goat skills.

Let’s look at the four common cheats, in increasing order of importance.

The Spouse Factor

I already briefly talked about the huge effect being married or in a committed long-term relationship on leaps into the gig economy. Even if you’re currently single, this is an aspect you should wrap your head around because it may be a factor in future leaps, beyond your first one.

The example I worked out last time was for a single person (or a single-earner household). It’s much harder to model a double-income couple’s finances, and even harder if you have kids. But there’s an upside to that complexity: a double-income couple can generally get by on a single income almost indefinitely with sufficiently aggressive austerities.

Why? Because people tend to marry or partner-up within their own economic class, and even if one spouse earns much more, the lifestyle tends to be baseline affordable by one alone. At least for a while. You may have to slum it out in the bottom of your social class or move down a rung, but you’ll live.

But as I noted in previous parts, getting married solely to enable gig economy participation is a terrible idea. It’s actually kinda like getting married to get a green card or visa.

In both cases, it can be a great bit of free upside if you want to get married anyway, but a fatal flaw in the plan if you don’t.

And while a financially stable partner can be a great asset, you also have to be on the lookout for the possibility that both of you might have to make leaps at about the same time. This is likely beyond random chance. To make your leap work out, you might have to do something like move to a cheaper city, which might force a complementary leap for your partner too.

In my case, my wife quit her job within a couple of months of me making my leap, in part because of conditions created by my move. She did get a new one shortly after, but for a brief period, we were in a pretty dicey situation.

But with all those caveats in place, if you are married, that fact can either be a huge strategic advantage or a major liability (amounting to divorce-grade stress) depending on how the two of you pool your strategic options. The advantages can range from the small but important things (like switching health insurance to getting a lease on the strength of your partner’s income) to big ones like managing a long ramping period of lowered income.

Even if your partner does not work, they will likely be playing a major role playing defense. As earner, you play offense and bring in the money. But managing a household budget on a volatile gig income, especially during a ramp phase, is vastly more complex than managing it on a paycheck. Everything from strategic prioritization of spending to being very savvy about sales and coupons, is worth real money. If your non-working partner has the right mindset for playing defense, they may be able to squeeze $1.50 – $2.00 in value out of every $1 you bring in. They may be able to basically sustain the same lifestyle you were used to, at a steep discount, simply by being smarter about spending money. A good defense partner is a major force multiplier.

You could do this for yourself of course, but remember, even cycle of brain time you spend playing defense, you’re not playing offense, so it is hugely valuable to have somebody else take care of that, allowing you to focus on the topline rather than the bottomline. Also, in my experience, playing offense and playing defense require very different mindsets that are rarely found in the same person, but are often found in a couple.

And finally, don’t forget: your partner is likely going to be one of the only sources of skills and support you might need that you don’t have to pay for with cash upfront. Chances are, they will not be actually interested in doing things you need done, and might not be particularly good at it, but they will likely do it anyway to support you, while you spin up the means to pay for the services from external sources. Your partner might end up as your unpaid book-keeper, web designer, spreadsheet wrangler, or copyeditor. And you will likely be reciprocating in the future, underwriting their risks.

The great thing is, partners who support each other through leaps into free agency will likely grow together strongly as couples and the relationship will benefit. After eldercare and parenting, it’s probably the richest shared growth experience you can have in a marriage. Of course, handled wrong, it can end in disaster, full of mutual resentment.

So factor in those options in making your plans. It is up to you whether your partner becomes your secret weapon or someone who weighs you down and turns the leap into a crash. To enjoy the former rather than suffer the latter, you must make them a full partner in your leap. A part of the solution rather than a part of the problem. If you cannot, then you must rethink either the leap or the relationship.

The Parent Factor

Even if you’re quite old, chances are, your parents can help in at least a small way. They may be able to give you some money outright. Or you may be able to temporarily live with them. Or they may be able to co-sign an apartment lease with you if you can’t show enough proof of income.

One particularly tough case I heard of was from a young Lyft driver, a Filipino immigrant. He was driving Lyft because his wife had died, leaving him to care for a young infant by himself. He had to quit his job in security work, which did not allow him the flexibility to handle childcare, and had to make things work another way. So he moved in with his mother-in-law, and she let him use her car to make money driving for Lyft, while she handled some of the childcare. He was taking ESL and computer classes at night to level up into something better.

That’s a pretty rough leap into the gig economy. One that could have gone far worse without a parent factor.

Don’t be snobby about parental support. Your parents’ generation probably didn’t have to try making it en masse in the gig economy, so give yourself a break, courtesy your parents (or in-laws), if you can. Inter-generational wealth transfer is a major dynamic in civilized life, and most parents are more than willing to help as much as they are able. Historically, parents in the US helped out their children via enabling early home ownership (for example by helping with a down payment). Helping you launch a gig economy career is the same sort of thing.

Of course not all parents are great parents, and support might come with psychological strings attached and patterns of abusive gaslighting. Be wary of disempowering false narratives, snide remarks about “getting a real job” and “when I was your age, XYZ” (especially if you’re leaping into the creative or artistic side of the gig economy), and general undermining of what you’re doing. And be aware that this is something parents can do unconsciously, without intending to, while still sincerely believing they’re being loving and supportive.

It’s not actually a strategic cheat if you have to pay for material support with your mental health.

(This risk of undermining is present in the spouse factor too, but is often easier to manage, in part because you choose your partner, but not your parents.)

Transient Cost-Down

In our leap risk model, we came up with a risk estimate based on the assumption that lifestyle would remain constant.

Chances are, you won’t maintain the lifestyle, but will be able to execute a planned, transient lifestyle cost-down with little to no loss of living standard. Moving to a cheaper apartment in a cheaper city is often the biggest piece of the cost-down puzzle. If you nail that, the rest falls into place. If you screw that up, other economies may not add up to enough.

If you’re single and have a particularly mobile gig economy strategy, moving overseas to a cheaper operating location is an extreme version of this cost-down move. That playbook has been done to death, so I won’t belabor it.

When I quit, we landed in Las Vegas because my in-laws have a home there they leave vacant anyway during the summers. For six months, we paid them a small rent that was 1/5 our DC rent, a sweet deal for both sides. Then we moved in to an apartment that was 1/3 the cost of our apartment in the Washington, DC area. That was a BIG cheat for a while (a combination parent cheat and cost-down cheat). When we moved to Seattle a year later, we returned to paying roughly DC-level rents. But the Vegas leg of my ramping period was a crucial strategic cheat. I estimate it was worth nearly $35,000 in saved rent alone, relative to our DC or Seattle lifestyle. We basically did a cost-of-living gravity slingshot through Las Vegas, between east and west coasts.

Be careful though: it’s easy to end up fetishizing frugal living (especially if both members of a couple are better at playing defense than offense) and letting the transient cost-down turn permanent. It’s fine if that’s what you were aiming for all along, and there are websites and mailing lists out there to help you with that. But here at the Art of Gig, we are solving for a non-minimalist, non-spartan lifestyle: just on your own terms rather than those of a paycheck employer.

If you are in the US, health insurance can be another big shock if you’ve never paid for fully loaded healthcare. The cost of COBRA (opt-in continuation of employer health insurance up to 18 months after quitting a job) or ACA (Obamacare) may be between 3x-5x the payroll deduction you’re used to. So you may have to make cuts in other areas to maintain the same or somewhat degraded healthcare.

Other countries mostly have more sane and gig-economy-friendly healthcare systems, but have other headaches. No country in the world is entirely friendly to free agency. We live in a world designed around paychecks, so understand the differences that makes to the cost of living, and plan your cost-down accordingly.

A transient cost-down is a non-trivial bit of planning, so don’t wing it. If you don’t have at least a couple of spreadsheets going to figure it out, you’re doing it wrong.

Exit Conditions

The biggest cheat in making a successful leap? It isn’t when or where you leap, but what you leap with.

What are your assets? What are holding in that big figurative bundle in your arms when you make the leap?

The things in that bundle constitute your exit conditions. This is one cheat card you MUST play. The other things can be optional or may not even be available to you, but exit conditions are something you can always design at least a little bit.

The worst exit conditions are: getting blindsided by being laid off or fired with no severance, when you are under immense cash flow pressure or debt, perhaps dealing with family emergencies, and being forced to make the leap empty-handed. Good outcomes are unlikely there, but if you’re ever in that situation, I wish you luck with it.

But if you can do better than that, and not exit empty-handed, your chances improve dramatically.

Some exit conditions are what I think of as low-cunning exit conditions.

• If you can time your first leap from a job at an old, declining company with a voluntary-retirement scheme, sweet. Grab that exit condition with both hands.

• If layoffs are being planned, with generous severance packages, and you can maneuver to be on the list, go for it. You may not be one of the people they want to lose, but if they have to meet specific headcount cut targets, they’ll be open to it.

• If you can exercise good employee perks, like getting subsidized software, just before you leave, do so. If your employer is folding and you get first shot at snagging used assets for free or cheap (like office furniture or valuable bits of intellectual property), go for it.

• If you have to wait a few months for some stock options or RSUs to vest, wait (but not too long: I walked away from a bunch because the vesting horizon was too far out).

• If you can get a new, cheaper apartment lease on the strength of your paycheck job just before you quit, do so.

Just be careful: don’t let low cunning exit-condition engineering turn into unprincipled or illegal behaviors. A typical gray-area case is “stealing” clients. You may be bound by a non-compete agreement, in which case it might be outright illegal. Even if it isn’t illegal, it may cost you in burned bridges and relationships, and reputational damage as people tag you as someone who pulls that sort of jerk move. Even if you are willing to take that damage, it might just be a shitty thing to do in that context to other people who don’t deserve it.

But there are also situations where taking clients from a job with you is both a norm in that industry, and the best deal for all parties concerned. Just be thoughtful and avoid hurting others in navigating this sort of thing.

Your main focus, however, should be on high-cunning exit conditions. That’s the real test of your imagination.

The best high-cunning exit condition is one in which you’ve created a live asset, out in the open, that can be turned into a viable foundation for a gig economy business with the flip of a switch. In my case, all it took to flip the switch was a post declaring I was going free-agent, and I instantly had a flood of live goodwill and support flowing towards me (including some sponsorship money, and a lead for what turned into a big gig a year later).

Throw-a-switch leap assets are of three major kinds.

• Marketing assets like a blog or newsletter where you can start to look for and create opportunities. I had both (the list, Be Slightly Evil, is now wound down, but available as an ebook).

• Product assets that can be turned into a money-making thing on Day 1. I had a nearly complete book that I was able to finish and put up for sale within a month of quitting. Instant spike of cash flow right when it was most useful.

• Live, hot leads that can be converted to starter gigs before you quit. I had 2 consulting gigs and a writing gig lined up a month before I quit. They didn’t amount to much, but having any cashflow going was a big deal.

Interesting point about the book: it was a hidden exit condition for me because I was quitting Xerox, where I’d learned a shit ton about print-on-demand economics and the publishing industry. So I was able to self-publish my book in the most efficient, highest-margin way possible, and make serious money off it.

Book publishing is great for reputation, but not generally a good way to make money unless you do it yourself and know what you’re doing. In my case, I did know what I was doing, so the book was a significant chunk of my income throughout my ramp period, and still continues to make decent money today, 8 years later.

So keep a particular look out for this kind of hidden exit condition too: valuable knowledge or skills you’ve acquired in the run up to the leap that you can deploy in ways most people cannot.

Putting it Together

So that’s it for the four major cheat cards, plus any others you have in your deck to play.

Put it all together, lay it all out on the table in front of you.

Stare hard at what you have.

Somewhere in there lies a cunning plan that can cover for your leap risk deficit.

Somewhere in there is tens to hundreds of thousands of dollars in risk mitigation value. Hard, financial, cover-the-rent value, not vague soft-assets value.

Somewhere in there is the key to leaping successfully versus crashing and burning.

If you haven’t yet made the leap, kudos for starting to think about it. Take a deep breath. Even with all the preparation in the world, it’s going to be something of a shock to your system. You will gasp for breath. Your diving reflex will be activated, figuratively speaking.

If you’ve already taken your first leap and survived, congrats. As you’ve no doubt already learned, there are no medals. Employees get employee-of-the-month awards. Startup founders get flattering media coverage and awards at conferences with pitch contests.

But there are no prizes for making a successful leap into the gig economy.

All you win is the opportunity to leap yet again. And again. And again. The reward for leaping is getting started on a learning curve that makes you better at leaping, putting you in touch with your inner goat.

The first leap into free agency and gig work takes a lot of nerve and imagination, which is why most people get involuntarily dumped into it involuntarily, via layoffs or firings, with a high chance of crashing and burning, rather than making the leap deliberately, on their own terms, with vastly better outcomes.

The nerve part lies in making the leap without having a complete answer to the question of how you’re going to make it work.

The imagination part likes in pulling together the minimum viable cunning needed to make it work, using the cheat cards you have available to you.

In these last 3 articles, I’ve outlined a basic approach to taking your first leap. Together, the ground we’ve covered so far constitute what you might call the outer-game of leaping. All the practical stuff.

In the next part, we’ll cover what I think of as the inner game: preparing your mindset and mental models for leap conditions. The really practical stuff.

We’ve hit 100 tips! For the past 100 business days, I’ve been tweeting a daily consulting tip on the @artofgig twitter account, and compiling them here periodically. Here are all 100 tips in one document if you want to print them out. I am working on putting together a deck of cards with these tips, which will be available shortly, but feel free to make your own flashcards if you like.

Starting tomorrow, we’ll switch gears, and the daily tweet will focus on a different aspect of the art of gig.

Here are tips 91-100.

Consulting Tip #91: If you get bored easily, do not try to develop repeatable, polished workshops where you expect the content to converge to 100% reusability within a few iterations. Allow yourself to mess around with the material as much as you like to keep yourself interested.

Consulting Tip #92: Do not pitch a workshop when it is not in fact the right way to solve the client’s problem. Workshops are tempting because they seem like declining-cost/appreciating-value assets that compound in value with every delivery instance. This can be an illusion.

Consulting Tip #93: To keep yourself honest, and avoid rent-seeking temptations, progressively transform valuable things you learn into the lowest-cost delivery medium possible. The first time you offer an insight/idea, it might be worth $1000, but the 100th time should be free.

Consulting Tip #94: No matter how you drum up work, inbound leads almost always result in vastly superior gigs, so even if you start out with outbound, develop a plan to attract inbound.

Consulting Tip #95: When you get a referral via a trusted friend or existing client, do not try to close the deal solely on the strength of their recommendation. Take the time to establish some direct trust with an exploratory conversation.

Consulting Tip #96: Use exploratory conversations to actually explore rather than sell or pitch your services. If you walk into a conversation unable to imagine any circumstances under which you might be the one to say “No”, you’re not actually exploring.

Consulting Tip #97: Learn to switch gears from exploring to closing gigs in a professional, courteous way. Cover all essential details — rates, contracts, NDAs — efficiently, without awkwardness or embarrassment. That can cause confusion, delays, and misaligned expectations.

Consulting Tip #98: Arrange to get paid in the lowest-overhead way possible. The best case is a client’s admin using a corporate card to pay invoices online (the fee is worth it). The worst is a baroque vendor management system that might be so bad, it’s a reason to refuse a gig.

Consulting Tip #99: Every now and then, take a moment to appreciate the fact that you live in an era where you can enjoy such a stimulating, enriching, varied, and free-ranging working life. Thanks to the internet, we have access to a kind of deep fun few in history have had.

Consulting Tip #100: Never forget that the future of work is already here, and you’re it. You’re a pioneer. Act like one.

Here is Compilation #7 (76-90) if you want to backtrack and catch up.

P. S. I am working on putting together a deck of cards with these tips, which will be available shortly. You’ll be able to use that as a convenient set of prompts for your introspection sessions, discussions with other practitioners of the Art of Gig, etc.

If you’re active on twitter, and want to join the conversation there, follow @artofgig, introduce yourself via a reply to this pinned tweet, and follow some of your fellow subscribers on this list.

Last time, in Your First Leap, we looked at the anatomy of the first leap into the gig economy. We looked at why people tend to fail at it by being underprepared in multiple ways. The lack of an obviously meaningful ceremonial starting point, like preparing a resume, pitch deck, or prototype, makes the problem worse.

So even though the risk, properly managed, is not significantly higher than a job search or entrepreneurial venture (lower actually, for people with ambiguous and/or low-demand skills), the outcomes are probably worse, because of these underpreparation factors.

So how do you prepare? So let me give you a starting point that is both useful preparation and a good ceremonial starting point: computing your unmanaged leap risk, as illustrated in this diagram.

Our goal with this exercise is to first estimate your income replacement horizon (in months) and from that, your unmanaged leap risk (in dollars). Let’s make up acronyms for these, why not: IRH and ULR.

• Income Replacement Horizon (IRH) is the transitional period you might have to endure to get back to your pre-leap lifestyle quality. There Will be a Dip. Your first leap is generally a planned economic recession in your personal life. The better you prepare, the shorter and shallower it will be.

• Unmanaged Leap Risk (ULR) is the dollar value of the strategic cleverness you must bring to your leap to manage this unmanaged risk. I call it minimum viable cunning. MVC. Without MVC you won’t be able to close the strategy gap required for a successful first leap, and barring a big stroke of dumb luck, you’ll end up in a traumatic crash that might scare (and scar) you out of the gig economy for life.

In other words, the estimation model assumes you’ll be doing something meaningful to manage the unmanaged risk, not sitting on your ass, and that you will be successful. If you leave it unmanaged, or fail despite trying to manage it, the model breaks. We plan for success not because it is guaranteed, but because it is the only thing you can tractably plan for. Failure is much messier than success, and planning for it doesn’t actually help much (in fact it can hurt), so why bother.

Here’s an estimation example. It is meant to be illustrative, not definitive, and you have to get good at making up such rough models on your own.

• Current monthly pre-tax salary: $5,000 ($60,000/year)

• Adjust with 1.5 benefits/overheads multiplier (generic job, generic benefits, no special infrastructure): $7,500/month ($90,000/year)

• Ramp length (divide by 10k, multiply by 4): 36 months/3 years <— This is IRH

• Unchanged-lifestyle income needed till IRH (7500×36): $270,000

• Average ramp income % assumption till IRH: 50%

• Perfect nominal safety savings target (36 months * 7.5k * 50%): $135,000

• Actual savings at first leap: $35,000

• Unmanaged leap risk (135k-35k): $100k <— this is ULR

In other words you’re taking a risky leap worth $100,000 in strategic cleverness if you make it. Take a look at the image to get a visual sense of this model.

The basic idea behind this computation is derived from job searching, but drastically modified. In job searching a common heuristic is that you can expect to look for a job for 1 month for every $10,000 in income. So a $60,000 job means 6 months of looking (and therefore having up to 6 months worth of savings for the most conservative preparation).

But the equivalent rule of thumb for a gig economy launch is that you can expect 4 months of ramping for every $10,000 in paycheck income (benefits-and-overheads-adjusted) you want to replace with gig income. So that same $60,000 income (worth $90,000 including benefits-and-overheads value) will take 36 months to replace, rather than 6.

This benefits-and-overheads value of a paycheck job is something like a free agency penalty because you have to make up for it on your own, often paying a higher direct and/or hidden cost.

If you were in a basic generic skills job, the multiplier of about 1.5 accounts for having to provide for yourself the basic amenities that jobs generally provide. Like health insurance (in the US), a retirement plan with matching, a computer loaded up with generalized and specialized productivity software, support from staff functions like accounting and administration, and most importantly, invisible perks like easily getting a lease or mortgage (via employers underwriting the risk of landlords renting to you, or banks lending to you, by guaranteeing your income).

How much in savings do you need before you take your first leap? Assuming a linear gig income ramp as shown in the diagram (optimistic; it’s more likely to be an S-curve where you draw down savings faster in the beginning), you can assume that about half your income needs in the interim will be met by live earnings. Revise this upwards or downwards depending on how in-demand your skills/services are.

So a 36-month replacement horizon for a 60k job with a 1.5x multiplier amounts to about $270,000 as an income planning target, assuming no downward adjustment in lifestyle. If you expect to meet half of this, or $135,000, with ramping income, you’ll need $135,000 to make the leap with complete safety and no significant lifestyle risks.

But obviously, trying to hit 135k in liquid savings on a 60k salary is ridiculously unrealistic for most people. At a very aggressive savings rate of say 20%, above and beyond retirement savings, it would still take you 10 years to prepare to leap. You’d effectively never do it if you’re that risk-averse.

A good way to think of this is in terms of a time advantage. You’re hoping to make up for this 10-year-long, dumb, no-risk preparation time with sheer strategic cleverness. You’re trying to leap 10 years into your own future, financially, by getting inside your own OODA loop somehow. You’re trying to disrupt yourself.

So you’ll leap with much less than the “safe” amount. You’ll take a risk and bet on your own resourcefulness. In the example, I’ve assumed 35k in savings, leaving 100k unaccounted for.

This difference is a measure of your ULR.

If ULR is zero, you’re not taking enough risk, or equivalently, you’re waiting too long to leap. But if you’re not doing some cunning strategery to manage this risk with levers besides more saving or drawing down other assets (second mortgage, borrowing against retirement account), you’re not being strategic enough.

In other words, you need to take on pretty high unmanaged leap risk, equivalent to a year or two of your current income, and then manage it using things other than money.

There are 4 main cheats for managing the risk: favorable exit conditions, a parental factor, a spousal factor, and a transient lifestyle cost-down (a permanent cost-down is not a strategic move; it is a values shift towards frugality or a cheaper “lifestyle design” in Bali).

Without cheats to manage it, the unmanaged risk part translates to an expectation of pain. Like homelessness pain. Or hunger pain. Or credit-card-debt pain. Or compounding-health-issues pain. Or tanking-mental-health pain. Or being-a-burden-on-friends-and-family pain. Or marriage-breaking-up pain. Or children-taken-away-by-social-services pain. Or doing-without-vacations pain. Or cutting-back-on-lattes pain.

You’re not a masochist. You don’t want to experience any of this pain. And if you plan right, you may not have to. Chances are you won’t get out of Ramping Jail free, but you can minimize the pain.

Your lifestyle pain tolerance may be high for merely staying alive, but to make a gig economy leap work, you can’t be in extreme, chronic lifestyle pain. You need a relatively clear head and a couple of latte treats a week.

And there are no dignity prizes for handling homelessness or untreated diabetes well.

So don’t be a hero.

Cheat.

Figure out a way to cover the unmanaged leap risk, or ULR, with things other than money. Conjure up the minimum viable cunning somehow.

Next time, we’ll look at cunning plans for doing this.