art of gig archive

Here’s a question. Which of these three pictures looks right to you? Do you see reality through your client? Do you both look at reality from different sides, or does the client see reality through you?

Trick question! The answer is all of the above and more. Because there isn’t just one salient reality in the picture, but several.

Here is a better view.

Can you spot how each of the 3 cases in the first picture also exists in the second one? The tricky one is (b).

These pictures are the key to solving what I called the dog-fooding problem for indies last week. To understand why, you need to understand a single key heuristic, which I’ll call…

The Reality Proximity Principle: Other things being equal, those closer to a reality will think faster and better about it.

Sometimes one can be too close, and miss forests for trees, but in general, being closer is better.

Consider a typical business with the following 7 relevant realities:

• X: Reality of how the manufacturing processes work

• Y: Reality of how long-term b2b customers’ needs evolve

• Z: Reality of how the culture makes decisions

• A: Macro trends in the environment

• B: How a relevant disruptive technology is evolving

• C: Political/regulatory environment for the sector

• D: How a competitor is thinking about the market

In this particular case (not in all), as a consultant, you have to see through the client to realities X, Y, and Z. They’re closer. But for realities A, B, C, and D, they might see that reality through you, depending on what position you chose to adopt. In some configurations, you might see different sides of the same reality (like the client and consultant in position 3 with respect to reality Z).

In other words, depending on which reality is salient for a problem or situation, you might be closer to it than they are. For example, many of my clients outside of Silicon Valley have at times relied on me to see Silicon Valley trends and practices better. They’re not interested in me and my ideas as much as the fact that I’m closer to the realities of Silicon Valley than they are while also being closer to their realities than most outsiders.

Now, how is this relevant to the dog-food problem. You may have already spotted the connection: dog-fooding is a behavior based on proximity to an internal reality.

Let’s recap the dog-food problem before talking about how to solve it for indies.

Recap

Last week, I wrote about the dog-fooding problem for indies, which is to apply the dog-food principle to indie consulting practice:

Dog-food principle: When a product or service could be an input for the vendor of that product or service, it should be used by the vendor as an input

Eating your own dog food is good for a variety of reasons: you can iterate faster by being your own lead customer, you create a better marketing perception, and you lower your costs. These advantages are so strong that being able to eat your own dog food is one of the biggest sources of strategic advantage for a business, and a big risk-mitigator for new businesses, including startups and indie consulting practices.

The flip side: all these great benefits only accrue if you are the market leader, or have a decent shot at becoming the market leader. For those already behind, being forced to eat your own dog food is a liability.

Now here’s the problem: as an indie consultant, not only are you very different from a business, you can’t even relate to employees at a human level because you don’t even face the same day-to-day practical problems. So “eating your own dog-food” becomes a hard principle to practice.

Now there’s many specific approaches to solving the problem in particular cases, but I want to share a general formula of sorts for solving it, based on the second picture above: reality arbitrage.

Reality Arbitrage

This might sound obvious, but your biggest advantage as a free agent is that you’re not inside the organization you’re serving. It’s not about who you are, but about where you stand.

This position makes it harder for you to see inner realities. Having to see those through your client creates a bit of a teaching burden on them, which means you start out with a liability even before you’ve proven your value. Why should they bother to help you understand the intricacies of their manufacturing model, or the mindset of their key customers, without knowing what you can do for them better than they can do for themselves?

And what exactly can you, as an individual living an ordinary individual life, do that’s so special?

But being outside their organization means you can get closer to outer realities relevant to their business, while also remaining closer to their inner realities than most outsiders.

This closeness may be some form of literal closeness. Maybe you spend more of your time going to industry conferences than they do, or spend more time tracking academic literature. Maybe you just happen to live in the city where their biggest customer or competitor is based, and you pick up a lot from overhearing routine coffee-shop gossip.

Or it could be psychological. Maybe you can get inside the heads of their competitors better than they can because you don’t share their identity hang-ups.

Don’t underestimate this: the NIH syndrome (Not Invented Here) is very real, and being inside an organization makes you systematically weaker at comprehending certain aspects of outside reality that might be inconvenient, dispiriting, or otherwise unpleasant. Interestingly, dog-fooding itself is the source of many such blindspots.

Whatever it is, the fact that you can be closer to some reality than them puts you in a position to do some reality arbitrage. As an intermediary, you may not understand the outer reality B as well as insiders of B, but you can understand it better than your client can from within their organization. By being closer to the the relevant inner reality X on the other hand, you can also apply the ideas of B better than insiders of B.

It’s basic arbitrage: you’re closer to both than they are to each other.

Reality arbitraging is not the same as dog-fooding, but it is a more than acceptable substitute that delivers many of the same advantages.

Reality Arbitrage vs. Dog Food

Both reality arbitrage and dog fooding are examples of a broad class of strategic advantages that have to do with being able to iterate and learn faster by being closer to a reality: ie turning the reality-proximity principle into a time advantage.

Dog-fooding is about being turning your natural closeness to yourself into an advantage. Reconsider the 3 benefits I listed in terms of distance-to-oneself:

1. Being your own customer makes you closer to your own needs

2. Your marketing works faster without the moral hazard/principal-agent problems, and this can be considered being closer to your own biases

3. And finally, the cost advantage of dog-fooding makes you closer to your own profitability

Dog-fooding is a special case of a know-thyself strategy. Being closer to your own needs means you eliminate some iterations based on misunderstanding of needs. Being closer to your own biases means you eliminate some iterations based on moral hazard. Being closer to your own profitability means money not used paying someone else’s margins turns into money devoted to speeding up pursuit of your own opportunities.

It’s a great principle for everybody in their personal life too, but your personal life is unlikely to be very relevant to your consulting work. So you have to look elsewhere for a similar structural advantage in time.

Reality arbitrage is that kind of advantage. When you play intermediary, you acquire a speed advantage that’s mostly useless to you personally, and pass it on. You’re a pass-through entity. And the reason you can do this is that as an individual you can occupy positions in the environment that larger entities cannot, and enjoy perspectives that are unavailable to them.

This is an unnatural advantage to exercise, based on extrinsic position rather than intrinsic qualities. For most of us, our own inner realities are the most powerful ones. We are constantly aware of them. The urge is to build an identity around them, locate your advantages within them, and draw on them to provide value to others.

That’s why dog-fooding is not just powerful, it is the default natural source of strategic intuitions. Even more crucially, at the individual human level, to be “seen” by others is to have your inner realities acknowledged and appreciated. It is one of the primary things people look for in a paycheck job after basics like compensation. People take jobs where their inner realities will be most relevant to the inner realities of the company, allowing them to express those realities and be seen.

For consultants though, it is less important to be seen, and more important to be seen through.

In both senses of the world: you are an optical instrument that enhances the vision of another, and your motives are transparent and easy to factor in. Just like a good optical instrument should have easy-to-correct aberrations and flaws.

This explanation is perhaps a bit awkward, but it’s a hard point to explain, or see early on in your indie career. Quitting a job and going indie is so much about listening to your inner realities that systematically deprecating the importance of those realities in favor of a different one can feel hard. Suspending the need to be “seen” can be actively painful, especially if you felt appreciated at your last job.

But consultants do best when they keep their identities small (Paul Graham had a good essay about that).

Examples

The most obvious example of reality arbitrage is of course playing “chess postman” of sorts: picking up tricks watching one client, and putting them to work on behalf of another. There’s a broad class of such tricks that you can safely transmit without fear of falling afoul of NDAs on either side.

For example, if one client runs meetings based on pure opinion-sharing, and another has a workplace norm that all meetings should begin with some data sharing, you can suggest data-driven meetings to the former where appropriate. You can say something like “I’ve seen some of my other clients use this data-driven meeting model and it works well for situations like this.”

Note what you’re doing here: you’re not testifying to your own experiences, or asking to be seen and valued for who you are. You’re not saying “I run my meetings this way” (which would be dog-fooding). You’re testifying as a credible witness to others’ experiences.

Another example is keeping up with macro trends. There’s a reason this is one of the bread-and-butter things consultants tend to offer. It is easier for consultants to stay on top of trends not because they have special access to information (especially for trends which are mostly playing out in public via media reports), but because they can get closer to them.

If you’re the Vice-President of Widgetry at BigCorp, you carry a gravity field wherever you go, and you’ll alter conversations wherever you go. But if you’re an unaffiliated nobody, you can participate in relevant conversations and learn a lot more. People will be more candid with you.

There are many other examples of external realities that you can help intermediate for clients. The key to all of them is to locate a valuable reality that you can get closer to than your clients can, for whatever reason.

In my case, a big one is simply staying on top of management trends and practices. Not by reading the latest airport bestseller, but by simply talking to a wider variety of people, and having a good handle on what’s actually being tried, and what’s actually working vs. not. Very few things covered by airport bestsellers are about actual management trends. Most are about things the authors wish would become management trends.

This is one reason I almost never make up my own management frameworks. I simply work with whatever is around and catching on. The moment you make up your own framework and start trying to sell it, you’re no longer really a consultant. You’re an entrepreneur selling a product. You’re not just at an advantageous viewing point, you have a point of view. You don’t just have perspectives, you have opinions.

You’ve expanded your personality and made your inner realities potentially relevant to others.

This is not a bad thing. It’s just a different thing. One that allows for dog-fooding as it happens: if you’re shilling a System X, you’d better be applying it to your own work and life somehow.

Maybe it’s just me, but I think there’s a certain deep pleasure to be found in resisting the temptation to do that. In working purely as a transparent intermediary of larger environmental forces around you, without trying to put your own dent in the universe. It is one of the existential pleasures of indie consulting. One that inventing and selling your own dog food ruins at least a little bit.

They say about the wilderness: take only pictures, leave only footprints. The indie consultant is the wilderness explorer of the economy. There is something rather poetic about taking pictures in some realities and leaving transient footprints in others.

Should indies “eat their own dog food”? It’s a surprisingly interesting question, when framed correctly for indies, but at first glance, it doesn’t even seem to apply to us in the general case.

It’s not a beginner question. It’s one that is hard to appreciate at all in the beginning, but gets more and more important as you log more years in the game. By the time you’re at say 6 or 7 years, it can start to feel practically existential.

I want to frame the question in this post, and give you a chance to think about it, before sharing my own answer in a future issue. But first, we need to understand the principle in its ordinary business context.

In the regular business world, including both b2b and b2c, the dog-food principle holds very strongly. I’ll state it as follows:

Dog-food principle: When a product or service could be an input for the vendor of that product or service, it should be used by the vendor as an input

It’s of course a big cliche, but an important and broadly true principle nevertheless.

Part of the reason is obvious. It is not a good look when you, as say the maker of a productivity app, don’t use it to improve your own company’s productivity. It’s a bad enough look that you may not be able to sell your product at all.

Curse or Blessing?

Eating your own dog food is obviously not an option available to all businesses, but where it is, it should be exercised, otherwise you’ll have some very awkward explaining to do when you attempt to sell it. Often you have no choice but to exercise the option. It’s a forced option.

But whether forced or free as an option, is the dog-food principle a blessing or a curse?

When your dog food is not actually the best dog food around, the principle can feel like a burden. This is not merely a soft psychological effect but a hard financial one.

There’s a reason companies often have to offer steep discounts to make sure their own employees use their products over competitors’ products. The size of the discount is in fact a good measure of the size of the burden.

For example, where I went to graduate school, in Southeast Michigan, there were a disproportionate number of Ford, GM, and Chrysler cars on the roads (I drove a Toyota). Some of it was of course regional or company loyalty, but a good deal of it was due to the employee discounts.

Another example. A decade ago, when I worked at Xerox, we had to use an intranet content management system made by Xerox called Docushare. It wasn’t exactly the best product of its sort around. It felt like an imposition to some of us who wanted to use other things, like Sharepoint, which was officially a competitor, and integrated better with all the other Microsoft products being used internally for other purposes (Docushare may have improved since then, but thankfully I don’t have to use either product now).

So the dog-food principle has a general reputation as a burden you need to be compensated for shouldering. But this is because most products and services are by definition not the leaders of their respective categories.

That is in fact the discriminating factor between whether it is a blessing or a curse. When you are the market leader, or have a decent shot at becoming the market leader, the dog food principle works for you and feels like a blessing. But when you are behind, with no realistic hope of catching up, it feels like a curse. Or at least a significant liability.

When the dog-food principle is a blessing, it is generally a huge blessing. This is due to at least three positive effects.

1. First, there is the natural advantage of having a major customer — your own organization — in the design and development loop, allowing you to iterate and innovate faster than when you are not your own customer.

2. Second, using your own product well gives you a significant marketing advantage. “We use it ourselves — and look at how well it works for us” is a very powerful marketing position, since it counter-programs the default perception of moral hazard that accompanies all selling (this is why products try to borrow the dog-food effect when they can, like toothbrush makers claiming their brand is most preferred by dentists for their own use).

3. Third, where the dog food in question is an important component of the vendor business cost structure, eating your own dog food translates into a big cost advantage. Not only do you get your own product at cost, your employees are trained to use it well, and even hack it/adapt it (which also feeds innovation, reinforcing the first advantage).

The dog food principle is so powerful, if you’re an entrepreneur, it is worth actively looking for business ideas that can benefit from it.

Serving a customer base that does not include yourself is in fact so much harder, other things being equal, I’d estimate dog-food businesses have a 3-10x overall advantage over comparable non-dog-food businesses, in terms of risk/return profiles.

In many cases, the dog food principle is so compelling, it is the reason the product or service exists at all. Not only does Amazon eat its own dog food when it comes to AWS, for a long time, it was the only customer for the service.

Often this kind of value is so high, you can even give it away free to others, as is the case with many internal Google products which went on to seed open-source projects.

Here’s a picture. Dog-fooding opportunities exist where the vendor’s needs overlap with those of the customer. It’s not rocket science.

Obviously, the dog food principle applies to some kinds of indie businesses as well. Anything where the client is typically a single person retaining you in an individual capacity in their “whole life” context rather than their job, is typically a regular dog-food business, just at indie scale.

Fitness instructors should be fit. Life coaches should not have train-wreck lives. Therapists should be mentally healthier than their patients. Executive coaches should have leadership traits. Yoga instructors should be better at yoga than their students. Dentists should have good teeth.

Now when does the principle not apply? When is the deep strategic advantage not available? And what are the consequences?

Big Dogs, Little Dogs

Obviously, the dog food principle does not apply, and is not available for strategic leverage, where the idea/product/service is not an input for the vendor at all.

A cancer drug maker is not staffed by cancer patients for example (though perhaps cancer survivors or relatives of cancer survivors might be over-represented among the employees — this would be interesting to look into). A cancer drug maker has biochemists, lab equipment, computers, staplers, and coffee machines as inputs. Not cancer drugs.

But the more subtle case where the principle fails to apply is when the customer and vendor are significantly different in scale or scope of operations. This causes an impedance mismatch. The version of the product or service you sell isn’t the one you need yourself. Big dogs don’t have the same needs as little dogs.

When there is an impedance mismatch, similar business needs might be served differently, and a vendor or its employees might not use their own products for needs analogous (or even, at a superficial glance, identical) to those of the customer. This is not hypocrisy, merely specialization of needs.

• For example, if you make large pickup trucks, it is unreasonable to ask all your employees to drive large pickup trucks, or offer big employee discounts to encourage it, since most people only need/want small sedans.

• If you make large airliners, your executives probably should not fly around in large airliners where they really need a small executive jet.

• Office printer makers should not expect their employees to buy them for home use (while at Xerox, I had a Brother printer at home because Xerox doesn’t make good home-sized ones, though they did offer an employee discount).

Knowledge-based service businesses are even more subtle. For example, have you noticed that big advertising agencies (so-called “agencies of record”) don’t advertise? Have you ever seen an Ogilvy ad?

Advertising, unlike the mass-influence-marketing businesses it serves, is itself a high-touch boutique relationship business, where sales happen via interactions between account executives and creative directors on the one hand, and CMOs on the other.

There would be no point to an advertising agency advertising its own services on TV. High-end advertising agencies are typically much smaller than the clients they serve. The latter also sell differently (through mass media, and large-scale distribution), to customers modeled in the aggregate as personas or demographic/psychographic groups. They do not sell to individual prospects modeled individually as in relationship businesses. So there’s no hypocrisy to advertising agencies not advertising.

At best you can look for more limited applications of the dog food principle. You wouldn’t trust an ad agency with a poorly designed logo or bad photographs on its website for instance.

Indie Double Jeopardy

It should be clear that the dog-food principle is generally not applicable to indies, either as a blessing or a curse.

For example, I consult on topics like organizational structure, business models, technology roadmaps, product strategy, innovation, and sustainability. Almost none of these topics is very relevant to either my personal life, or to my tiny 1-person business. The approaches I use with my clients would be cartoonish overkill for the versions of those problems I face myself.

Even where there is apparent commonality, there is likely to be a very strong impedance mismatch.

For example, companies big and small require web pages. But as an indie, your need for a website is very different from that of a Fortune 100 company. If you’re doing web design for big companies, it would be silly to pretend that a huge, complex, heavily trafficked website should follow the same principles as the typical indie consultant site (which might be a single static page hosted for free on Github, like mine).

But the effect is in fact worse than that. Indies face a type of double jeopardy because they don’t share a common input shared by all traditional businesses — being organized as a traditional multi-person business. This input is normally invisible, except during events like mergers and acquisitions between companies, when it becomes clear for example that “corporate culture” is a kind of dog food that matters when you try to sell the company itself to another company.

Not only do you, as an individual, not need the same inputs your clients need, or need them at the same scale or scope, you’re not even the same when it comes to ordinary human needs. You might legally be a corporate entity, but you’re really just a single worker, not an organization. And a very different kind of worker than an employee.

This means many basic inputs shared by all businesses are different for you, making selling to businesses twice as hard.

• When a typical employee at a large company needs a stapler, they go look in the supplies closet or ask the office manager, making do with the standard stapler. When you want a stapler, you order one from Amazon, picking out one you like.

• When a typical employee goes to work (pre-Covid edition), they go to an office laid out in an open plan that they probably hate. As an indie, you’ve probably arranged a pretty sweet home workspace for yourself.

• A typical employee has many friends “from work” especially in smaller cities. As an indie, it is very unlikely that your friends circle and clients circle overlap very much. And if a friend becomes a client, chances are the client aspect starts to dominate.

• A typical employee probably uses Microsoft Office at work. You probably use Google Docs.

• A typical employee has to deal with a lot of day-to-day corporate bureaucracy. You are free of much of all that.

All these factors make it harder to “eat your own dog food” at a very basic level of business behaviors. You can’t even easily recommend a stapler!

Over time, it becomes hard for long-time indies to even relate to employees of client organizations and recognize their ordinary human needs in a business setting. Because you no longer operate in the context of a large organization, you lose the ability to operate in anything but an individual capacity.

Don’t underestimate the slow erosion of empathy and emotional and lifestyle distancing that occurs unless you do something, as you log the years as an indie.

The longer you’re in indie mode, the stronger the impedance mismatch between your needs and client needs, because you gradually lose the internalization of big-org needs at a business level, and empathy for paycheck employee mindsets and needs at a more fundamental human level.

You might say — it’s hard to eat your own dog food at a basic human level in relating to client employees because you slowly start turning into a cat.

You eat cat food while making dog food for them. Not only do you lack the dog-fooding advantage, you suffer a cat-fooding liability.

A sort of double jeopardy in short.

You’re not a b2b, b2c, or c2b business. You’re a c2d business: cat-to-dog.

Framing the Indie Dog-Food Problem

So we can now state the indie dog-food problem.

How do you apply the dog-food principle to your independent consulting practice, in order to realize the strategic upside, despite the lack of strongly overlapping input needs with clients, the lack of impedance-matched scale and scope of the few needs that might exist, and the growing human distance from employment-based lifestyles?

Or a shorter version: how can a cat sell dog food, and extract dog-fooding advantages out of cat food?

(Incidentally, as pet owners among you might know, cat food is in fact different from dog food. As obligate carnivores, cats can’t digest plant-based ingredients easily, unlike dogs).

Big hairy problem, isn’t it?

You might not see why it’s an important problem if you haven’t been in the game very long. But part of the reason so many people flame out so early in the indie lifestyle, and head back to employment, is that the lack of a dog-fooding strategic advantage (plus a cat-fooding liability) radically increases the crash-and-burn rate.

And if you do survive, the growing distance effect makes it increasingly hard to care about the kinds of problems businesses, and the people within them, face.

After all, you went indie in part to escape those problems in the first place. Learning to care about them again from the outside takes work, and can feel strangely perverse.

Left unmanaged, the indie dog-food problem can turn into a one-person “employee engagement” problem. You become disengaged from your own practice, slowly more ineffective, and start losing gigs. Eventually the practice can become unviable.

So how do you fix it?

I’ll share my own answer (I’m sure there’s more than one) in a future issue, probably next week.

If you’ve been in the game a few years, and have ideas about how to address the problem, take a stab at it. Either do a response on your own blog or newsletter, or if you like, send me your response. I might feature it in the issue where I share my own answer.

You may have noticed that a career in the gig economy is inextricably linked with lifestyle design. People who live off gigwork also tend to design their lives a lot more actively than paycheck people.

Why this confluence of gigwork and lifestyle design? It’s a historical moment thing.

People in the gig economy are at the vanguard of the world getting off a century-long artificial separation of human lives into producer and consumer aspects. We in the gig economy have been the early pioneers of the prosumer economy for a couple of decades now.

For normal people now uncomfortably cast into work-from-home mode, it is slowly becoming clear that we represent the mainstream future, rather than a present sideshow.

That that what they used to think of as “work-life balance” is a pale shadow of the real thing. That it’s something we figured out years ago, and they’re just beginning to wrap their minds around.

The Prosumer Moment

From the point of view of “normal” middle-class people fully invested in the paycheck lifestyle, gigworkers appear to unreasonably and perversely reject perfectly fine standardized consumption life scripts, scripts that have worked for a century for billions.

We have weird lives with lots of non-default aspects. We live in unexpected places relative to our personal and professional backgrounds. We have strange circles of friends, and associate with disturbing and sketchy people. We come and go unpredictably from the scenes we are part of. Our living arrangements and relationship patterns are illegible and confusing. We are a lot more freakishly invested in our side activities and hobbies than is seemly.

Our “normal” friends and family feel slightly embarrassed by us, and constantly feel the need to make excuses for us.

But we don’t lack respectability so much as being outlaws relative to respectability norms.

Ever so slightly, each of us undermines those norms by our very existence.

There is a general, undefinable air of slight disreputability to us, but it is a disreputability alloyed with a vaguely threatening presence that makes normal middle-class people uncomfortable rather than contemptuous.

Gig workers present as threatening counterexamples to the assumptions that certain scripts must be universal. Scripts that embody a way of life a majority of people, and entire developed societies, are very invested in.

We live prosumer lives that are hard to directly compare with the producer-consumer Joneses. Lives that are hard (and rather pointless) for others to try to imitate or compete with, due to the many bespoke elements.

For people living lives based on imitation and comparison, this can feel like an existential threat.

The Fundamental Theorem of Postmodernism

You could even make up an equation for this historical moment. I’ll call it the fundamental theorem of postmodernism.

Prosumerism = Gig work + Lifestyle Design

In some ways, this equation describes something like the pre-modern economy, where most work and life happened within the domestic sphere of agrarian life for most people, and working for cash in globalized markets was only a small part of life, relating to dealings beyond the family.

But in other ways, it is nothing like the premodern way of life. It is radically postmodern, and makes highly leveraged use of the most advanced capabilities civilization has to offer.

Instead of pointing to the vast majority of humans living very similar, miserable lives without modern conveniences like running clean water and well-stocked grocery stores, it points to a flourishing variety of lifestyles that combines the best of pre-modern and modern into post-modern.

That’s prosumerism as postmodern praxis (check out the Yak Collective report, New Old Home, for more on the home-design aspects of this)

We gigworkers and lifestyle designers are the true prosumers, and I want to claim the term for us. Which means kicking out the people who are currently squatting on it.

Prosumerism as Postmodern Praxis

The term prosumer has so far mainly been used in weak ways for ordinary paycheck-earning consumers who participate in minor, peripheral ways in the production aspects of things they consume, but are not employed in the production of.

This is just prosumerism as a form of shadow labor, an industrial lifestyle++ rather than something new. Bagging your own groceries, assembling your own IKEA furniture, completing surveys in exchange for gift certificates, entering contests to provide “customer-led innovation” ideas to companies. It’s all just ways for the consumer economy to sneakily make you do uncompensated, inefficient, low-value production activity for it, in the guise of empowerment and voice.

And the median human in the paycheck world is so disempowered, this feels like actual meaningful agency (check out Paul Ford’s great riff on this point)

The slogan of this kind of prosumerism is enter for a chance to win. Extreme couponing is what counts as lifestyle design within it.

So many layers of irony and existential despair folded into that phrase.

But there’s a better way to understand prosumerism: as an imaginative blending of production and consumption enabled by deliberately engineered and risky flexibility on both ends.

You need to do two things to qualify as a real prosumer by this definition:

• First, you have to give up the perks of your paycheck job by going free-agent. That gets you production flexibility.

• Second, you have to give up standardized consumption scripts as your source of status validation. That gets you consumption flexibility.

These are risky things to do, financially and socially. But what you get in return is enough flexibility on both ends to make prosumption worthwhile, and preferable to separated production and consumption.

If you have the imagination, you can use that flexibility to overcome the risks and come out on top.

This is the prosumer gambit. It is neither an exit decision, nor a voice decision. It is a way to cut your own personal deal with postmodern realities. Instead of playing the twin games of “employee engagement” and “customer satisfaction,” you make up your own game of living a quality life as a whole human.

Let’s understand this through 2 pictures. I just got a nice whiteboard for my office so you’re going to get artisan, hand-drawn whiteboard drawings for this issue.

The Producer-Consumer Life

The paycheck lifestyle can be understood as 2 funnels that meet at their narrow ends, a producer funnel and a consumer funnel.

The paycheck lifestyle is a split-brain producer-consumer lifestyle bridged by the all-important paycheck as the conduit of all value. It is the corpus callosum of the 2 sides of your industrial-age brain.

The key point is that all work ends with paychecks, and all of life begins with paychecks.

Work-life balance is a cash balance. Ideally you want the equation balanced, or running a surplus. There is no other pathway for effort to turn into value. Cash is the enabler of all things, and the bottleneck in all things.

On the producer side, your job is your immediate income-generating activity. Behind that is your job strategy, which is how you maneuver for promotions and plum assignments within a job. Behind that is your career strategy, which is how you manage your job-hopping.

And finally, at the mouth of your funnel is your education strategy, which is how you charge up your potential energy to drive all the kinetic maneuvering at narrower parts. It’s education rather than learning because almost all of it is front-loaded into formal education. As you grow older, and time/opportunity for continuing education decline, you run out of potential energy and top out into your terminal career role. Learning in an open-ended sense is not naturally integrated.

On the consumer side, your life begins with immediate cash expenses. Then you have bad debt (credit cards, payday loans). Then you have supposedly “good” debt which may or may not be actually good — home mortgages and education loans. And finally, if you’re lucky, you have a zone of equity accumulation: home equity and retirement portfolios. These are passive for you. They’re not an actively managed part of the income/production side of the equation. Investment as income is for rich people. For the rest, investment is a build-up-when-young/draw-down-when-old/pass-on-to-kids activity. It’s part of the consumption side, as deferred future consumption. And it rests on the obviously false assumption of risk-free 3-8% growth embedded into retirement calculators.

Note that both sides are funnels with leak-proof walls and a directionality. You can only progress via linear stages from broader to narrower on the producer side, and narrower to broader (and more dangerously leveraged) on the consumer side.

There is no strong pathway for education to improve your life besides being converted into career strategy, then into job strategy, then into a job, then into a paycheck.

This isn’t necessarily a bad picture. It’s just a picture that’s a lot more attractive for a small minority of big winners than for the median person trapped within it.

Now for the gig economy version.

The Prosumer Life

Now consider the prosumer lifestyle. It is tempting to map “gig work” to “producer” and “lifestyle design” to “consumer” and simply reproduce a relabeled version of the two funnels, but that’s not how it works.

There are two sides, but they don’t map cleanly to production and consumption. There’s a lot more going on.

They map, instead, to risk management and living life. Each side is a set of nested circles that again meet at the almighty dollar, but unlike in the two-funnels world of paycheck people, these circles have porous boundaries, and value can flow across the two sides of your life in much more open-ended ways, not just through paycheck dollars.

Here, there is no clear mapping of “work” on one side and “consumption” on the other.

For example:

1. You might start with a “hobby” (say astrophotography, something I’m getting into right now) that’s nominally on the “live life” side of the equation. There’s no significant risk-management involved.

2. There you meet someone interesting in the “social network” circle (say a fellow amateur astronomer at a star party). Note that it’s just one generic social network, not a “work” or “friends” network.

3. Then this relationship sparks an idea and bleeds over to the exploration circle on the “manage risks” side via a partnership to take a financial risk together (like pool funds to buy photography and telescope equipment, which is expensive and low-utilization).

4. That then leaks through to the income-generating assets circle where maybe the two of you create a website (say a site devoted to great astronomical photographs that also affiliate-markets telescope and photographic equipment, and offers a course on astrophotography or DIY telescope-making).

5. This makes some money that you then share.

It’s not that this sort of interesting story can’t play out in the two-funnels paycheck world, it is that it is highly unlikely within the two-funnel structure. In this particular example, astronomy is a night-time hobby that seriously disrupts a 9-5 paycheck job (and the associated evenings-weekends earmarked “family and social” time), but fits easily into a gig economy/lifestyle design prosumer life.

“Converting” the fun hobby into an income-generating asset is a much more natural thing to do as well, since gig economy people tend to not have values based on purist separations of work and play. For paycheck people, a “hobby” is likely to be a very sacred escape from “work” (says a lot about work as a psychic prison) that it would be profane to try to make money off of.

Collaboration is also easier. Paycheck people rarely have patterns of availability that allows for serious collaborations outside of their jobs.

Finally, note how risk management plays out here. Paycheck people have steady incomes, which means they have stable marginal values for both their time and money. If you make a $4800/month salary at a 40-hour/week job, every work hour is worth $40, and if you strive for work-life balance, so is every leisure hour. Which means you’ll want a significantly higher than $40 expectation to “sacrifice” a leisure hour on a risky venture.

But if some months you make $10,000 and other months you make zero, the marginal value of your time (and money) varies wildly around that mean. It is much easier to randomly throw a dozen hours at building a website that might make no more than a few dollars a month in affiliate commissions. It is much easier to simply take a low-value gig just to learn a new industry. It is much easier to get very seriously into a hobby during slow periods.

Consumption and Status

Don’t underestimate the status constraints of the consumption life-script side of paycheck lives either. For a paycheck person with a nice title and a house in the suburbs, who meets coworkers everyday (now on videoconference), keeping up with the Joneses and conspicuous consumption are inescapable parts of life.

It is much harder to “break status” and do schleppy things “beneath” your status, either at work or home. It’s like breaking character as a worker in a theme park.

For a paycheck person, it can feel seriously degrading to do things that would seem menial in relation to their work, like running a website with affiliate links, or teaching a self-published course.

Things paycheck people do outside of work must reinforce the status they project at work and in their communities (or at least, harmonize with it).

For a big, important Vice President at a major company, menial things — like say working with blue-collar tools — might only be acceptable if they are done as part of a status-reinforcing hobby, like building hand-crafted furniture in a garage workshop that’s kitted out with only the finest equipment. The idea that your workshop might be the backend of a side hustle selling little wooden boxes on Etsy can feel really demeaning.

If you’re a Senior Fellow as an experienced engineer at a famous company, you might only be willing to teach what you know if it is as an adjunct professor at a well-known university (even if it makes you little to no money relative to an equivalent self-published course). For a respected engineer, teaching and marketing their own course, without credits from a prestigious university attached, and without an existing pipeline of prestige-branded students conditioned to respect you, can feel demeaning.

But for a gig economy person, these sorts of things are what makes prosumption lifestyles both fun and flexibly risk-managed. When your marginal hour is worth anywhere between $5 and $500, and status considerations are much weaker in your life, you can do a lot more with all your time.

During a slow period on the high-end consulting front, it feels perfectly natural and fun to spend long periods of time doing “menial” things.

During a high-demand period, it feels perfectly natural to let work-life “balance” get seriously out of whack for a while, as you make hay while the sun shines.

When you tire of an activity, it feels perfectly natural to level up and turn it into an online course, so others to whom it is new, fresh, and interesting can take over what you used to do, and you can move on to your next adventure. It’s not about status as a respected teacher. It’s just another hustle.

At any time at all, it is easier to do what you want, rather than what a script tells you to do.

Beyond “Evenings and Weekends”

Chris Dixon once famously observed that “What the smartest people do on the weekend is what everyone else will do during the week in ten years”

Drew Austin recently tweeted a snarky version: “what hot people are doing today, smart people will be doing in 10 years.”

Chris’ version gets at the nature of the entrepreneurial escape hatch from the producer side of the paycheck world, driven by smart people jailbreaking themselves.

Drew’s version gets at the nature of status competition on the consumption side, driven by trends and fashions set by attractive people pwning the social status game.

What both have in common is that they accept as a given the central role of imitation in the producer-consumer divided lifestyle model. Work and life as competitions fueled by imitation, signaling, and envy. To win is to have others want to be like you, but without beating you.

The great allure of the prosumer way is to break out of the straitjacket of a lifestyle unnaturally divided into production and consumption aspects, each driven by its own patterns of imitation and competitive signaling. This is why going free agent feels synonymous with “getting out of the rat race,” even if you actually work a lot harder.

Done right, it can be a lot more fun, and a lot less rat-racey, while actually being more impactful than being the Joneses.

The first step is gaining radical control over your time. Everything else follows naturally.

What might a prosumer version of the line be?

While imitation is still a big piece of the puzzle (witness the huge subculture of Tim Ferriss imitators in South East Asia), it tends to be conscious, critical, and cautious imitation driven by pragmatic and strategic considerations, with a lot of experimentation and tweaking to make it work for you. When free agents take courses from each other, they tend to act like canny prosumer shoppers investing in themselves, not resume-stuffers trying to get an A+ with the lowest effort possible.

Imitation for a prosumer is not a simple matter of “I’ll have what she’s having.” It is imitation as strategic borrowing of a good idea as a starting point for life-energy investment. It is not some sort of depressing and gloomy trajectory of Girardian mimesis underwritten by a paycheck.

So a prosumer version of Dixon’s line is definitely not something like “what gigworkers do today everyone will do in 10 years.” We do represent the mainstream future, but not in that literal-minded way.

That would be a failure of this historical moment to live up to its potential.

Instead, it’s something like “what a gigworker does today will either not exist, or will exist in a hundred variant flavors in ten years.”

And that’s the real attraction of where this historical moment can lead us: to a world of flourishing variation and natural selection in life and work, instead of a world of depressing, in-bred, purebred dog-show sameness.

What exactly are free agents free from? In sports, a free agent is someone who is free of allegiances to a particular team. In knight-errantry, a freelancer is somebody who is free of allegiances to a particular feudal estate or monarch.

So what are free agents in the gig economy free from?

In the gig economy, freedom is primarily freedom from being managed. It’s a freedom that can seem like a curse to those who either enjoy being managed, or are too inexperienced to have learned adequate self-management behaviors. But like it or not, this is the freedom you have in the gig economy, and there is an art to thriving under this freedom you must learn, or it turns into a burden.

This freedom exists not because we free agents brave the wild open economy and carve out sweet manager-free territories for ourselves, but because there are rapidly growing regimes of valuable work (knowledge intensive ones in particular) where traditional people management as a function simply fails, and where the typical organizational response is increasingly to just eliminate it in those regimes. Such elimination moves often create gig economy roles as a side-effect.

The regime of effectively unmanaged work is increasing in size in the modern economy. I don’t have numbers to back this up, but my anecdotal experiences suggest managerial failures are a significant driver of growth in the gig economy.

Bad managers — represented by fictional archetypes such as the pointy-haired boss in Dilbert, Bill Lumberg of Office Space, and Michael Scott of The Office — are a symptom rather than the cause. Their existence points increasingly points to the growing untenability of people management as a function rather than individuals failing to be good managers.

Does this mean good management does not or cannot exist under modern conditions? Of course not. But it is playing a shrinking role.

The free agent economy in some ways represents a civilizational bet on a radical idea: what if, instead of trying to FIX managerial failure, we try to do without it altogether?

For students of management and organizations, the free-agent economy is in some ways the control group of people management theories. If your theory of people management cannot deliver better outcomes than the essentially unmanaged work processes of the free-agent economy, it is not a contender.

The existence of pointy-haired bosses, Bill Lumbergs, and Michael Scotts in the world is a symptom of the failure of management as a paradigm for coordinating work. It is no accident that many of these familiar contemporary “bad manager” archetypes are from fictional software companies.

Are Free Agents Managed?

I have had about 5 years experience being managed in a traditional sense, and 9 years in the gig economy where even if I stretch the definition, I cannot say I have been managed at all, in any sense I recognize.

As a free agent, you might have a client with expectations, and you might deal with someone in a “vendor management” function when it comes to paperwork and contracting logistics, but you are generally not managed the way employees are. The exception is subcontracting. If you’re managed at all, there’s a good chance another free agent — a prime contractor — is doing it. There’s also a good chance they’re doing it badly, but that’s a story for another day.

As a free agent you might also be free of other things, such as a 9-5 schedule, certain kinds of paperwork and training burdens, and so on, but those freedoms are generally not as robust. On a big gig with significant coordination needs with client employees, you might end up on a 9-5 schedule anyway. Your paperwork burdens as a small business owner or contractor might end up being greater than those of employees, depending on the client. You might have to put more effort into training yourself and acquiring certifications that open doors to gigs than employees do.

But the one robust freedom is freedom from being managed. So it is important to understand what it is to be managed, either well or poorly, and what it means to do without.

What Managers Do (In Theory)

One of the very interesting things I’m learning as a result of writing this newsletter is that increasingly, young people are directly entering the gig economy as their first foray into the workforce, and since the gig economy doesn’t really have managers (unless you count algorithms), they acquire no experience of being managed, have no idea what managers do, and no idea how to do it for themselves when necessary. So the freedom from management turns into a curse because they don’t know what they don’t know. Because they’ve never seen it. From a yearning distance, “being managed” can even start to seem like a blessing, something to aspire to if you haven’t experienced the reality of it.

So let’s review what managers actually do.

Managers do many things in organizations, but traditionally, the core of what they are supposed to do is manage the risks of individuals failing. Individuals can fail in many ways:

1. Do the wrong thing (misdirect effort)

2. Do the thing wrong (make mistakes)

3. Cut corners and do poor work out of laziness

4. Work too slowly, creating delays

5. Game incentives and work to minimal standards

6. Act maliciously due to unresolved resentments

7. Act unreliably due to personal life issues

8. Lie or cheat in reporting on work

9. Fail to resolve conflict with other employees

10. Become unable to work due to illness

11. Fail due to lack the right resources to succeed

12. Fail due to essential tools or systems failing

Managers exist because organizations need to function despite this vast potential for individual failure. Historically management arose as a function out of the need to mitigate the risks of such failure. Many of the other things managers traditionally do, such as set targets, supervise training, fight for budgets, and relay information, arise out of the primary job of managing the failure potential.

The cynical assumption that employees will fail in various ways unless actively managed is often known as Theory X, while the opposed idealistic theory, known as Theory Y, popularized in the 60s by Douglas McGregor, holds that left to themselves, employees will generally do the right thing. Under Theory Y, the core of what a manager supposedly does is promote the growth and well-being of employees, rather than manage the risks of their failures.

Both theories are empirical on the surface, and could in principle be tested. You could research a company to see if employees are succeeding or failing by default, and whether failure mitigation or growth promotion adds more value. But in practice, Theory X and Theory Y tend to be workplace ideologies adopted as untested values, rather than being selected as the more accurate description of the specific workplace.

Theory Y was popular for a couple of decades, but with deregulation and increasing competitive pressure in the 80s, Theory X enjoyed a renaissance.

The early phases of digital transformation of businesses in the 90s and 00s saw the increasing strengthening of Theory X tools (Big Brother at work basically) — worker surveillance tools, self-documenting, high-transparency workflows, open-plan offices, and an increasing emphasis on “collaborative” cultures (which is usually code for reliance on a culture of peer surveillance).

Theory Y tools also emerged — goal setting tools, “performance management” tools, “employee engagement” tools, and so on. But despite cosmetic Theory Y layers, most workplaces today, including knowledge-work-intensive workplaces, have a default Theory X culture.

In theory managers manage failures. So what happens when managers themselves fail?

When Managers Fail

Today, at the tail end of the neoliberal, globalized era, we can say that to a first approximation, Theory X (with a cosmetic veneer of Theory Y) is used to manage low-wage, low-skill, highly interchangeable and precarious employees, while Theory Y is used to manage a small subset of high-wage, high-skill, hard-to-replace secure employees.

Theory X is used to manage workers destined to have their jobs eliminated or dumbed down maximally through automation, while Theory Y is used to manage the shrinking number of workers who are irreplaceable by automation and very expensive to replace with other humans.

So why free agents?

Free agents exist because whether they are serving in a Theory X or Theory Y role, sometimes managers fail and turn into net liabilities. This is most likely when the work being done has a strong element of a principal-agent problem, due to knowledge or skill gaps (the manager doesn’t know or cannot do things the employee does). This can happen due to either specialization of roles, or situational differences when manager and employee are not collocated (as in remote work, or more recently, work-from-home conditions under Covid19; anecdotal evidence suggests managers are really having a hard time being effective under WFM conditions).

Either way, the ability of the manager to either address failures, or promote success, is sharply limited by lack of knowledge (contextual or specialized), lack of skills, or both.

So you have this matrix:

If the existence of managers isn’t helping failing employees become successful, or successful employees grow, what’s the point of them?

By presenting ways to do away with managers altogether, this is the question software tools allow you to ask, and often the answer is “there is no point.” So software eats managerial roles.

The resulting elimination of human managerial functions also drives the structural evolution that refactors the job itself as a gig economy job.

When the response to failing management is to do away with it, the free agent economy grows.

Managerial Failure = Gig Economy Growth

There are two potential outcomes of managerial failure: below the API gigs and above the API gigs.

In the below-the-API case, you can replace managerial roles with automated software layers that provide the necessary coordination function, dispense with the other softer functions, and rely on opt-in market dynamics and economic incentives to shape the managed function. This is how you get under-the-API gig economy: rideshare drivers and the like.

Note how this layer works. The failure modes are not “managed” for the most part. Absenteeism and slacking are not motivation problems to be “managed” for example, requiring either penalties imposed or a pep talk from a manager. Rideshare drivers simply work when they want to and are paid accordingly. If they do a poor job, bad ratings kick in and eliminate them. On the success side, if they do very well, the algorithm itself rewards them, along with better tipping dynamics.

Sweet deal, huh? Except of course that any job that is legible enough to be refactored this way is also very likely ripe for automation.

In the over-the-API case, you get the kind of free agency we mostly talk about in this newsletter: indie consulting, high-skill contracting and so forth. In this case too, there is no management. If you fail, you simply lose the gig. Management is reduced to hiring/firing free agents and dealing with them as vendors/suppliers of work rather than employees. If you do well, you get more inbound via referrals, and can either make more money by working more, or by raising your rates.

To succeed in either case, you have to learn the art of being unmanaged.

Managing Yourself

In the under-the-API case, being unmanaged is easy. You learn to play the algorithm’s game as best you can for your kind of work. As a rideshare driver, maybe you only work during surge pricing. Maybe you loiter in areas where you get many quick turn-around short trips rather than rare long trips with long empty backhaul legs. If the platform changes the algorithm, you change your behavior and figure out a new optimum or quit the system.

Managing yourself under the API simply means setting goals and then working the algorithms to hit them sustainably with the least effort possible. For example, I saw some research I can’t find now that showed that many rideshare drivers simply work till they hit a target daily amount, and then punch out, regardless of whether it’s a high demand period when they could make a lot more money in a short period. Where a managerial solution would try to motivate the drivers to work more to meet the demand, the algorithmic solution is to raise prices and move to a different market equilibrium. Customers change their expectations and intentions too. Those unwilling to pay surge prices simply wait out the surge or find alternative modes of transportation. As a result, the system, while not a one-to-one substitute for an equivalent “managed” service, works well enough to sustain itself.

In the above-the-API case, managing yourself is much more complex. The two obvious things you can do are simply supplying the Theory X and Theory Y functions yourself to the extent you need them. You can monitor your own failures and try to learn from them. You can watch for where you’re doing well and double down there by giving yourself pep talks.

But the biggest aspect of managing yourself above the API is to get to an oversubscribed state where you can pick and choose what gigs to take, and where you have the genuine freedom to walk away from gigs that aren’t working out. The better part of managing yourself is simply working on the right sorts of gigs, and saying no to the wrong sorts.

In other words, instead of managing yourself, you seek out work where you don’t need as much management.

The Unmanaged Future of Collaborative Work

As the free agent economy grows, and takes on more complex functions, requiring increasing coordination among free agents, the art of being unmanaged will evolve.

Some of the experiments we are doing over at the Yak Collective involve researching precisely this evolution.

How do you run team projects without a traditional project manager?

How can a multi-role project get staffed and completed with much less cat-herding by a manager, or even no cat-herding?

Can you create rideshare like algorithmic platforms at the scale of a single small project?

These are problems that we are just starting to figure out. In every case, there is a temptation to simply reproduce the traditional solution: “manage” the problem with a “manager.” But it is the solutions that reduce or eliminate the need for management, while producing equivalent or better output that will be the interesting and exciting ones.

In most cases, these won’t be 1:1 substitutes for managed project outputs. When you work in unmanaged ways, you tend to do different kinds of work as well. The nature of the economy itself changes. It creates wealth and meets needs in different ways than one with managers. You get more things that look like crowd sourcing, and fewer things that look like curated, “managed” outcomes. Things aren’t managed or left unmanaged via unexamined defaults or due to the inertia of past practices.

Instead, management becomes yet another design variable in business models.

For people in paycheck careers, the “career path” is a familiar and useful long-term planning artifact. For free agents on the other hand, there is no such convenient construct, which makes meaningful long-term comparisons between paycheck and free-agent careers hard.

Worse, the lack of such a construct means free agents often fail to even imagine meaningful progression in the work lives, leading to increasing disenchantment through lack of growth.

So they do the same thing in Year 10 as they did in Year 1, not because they want to (which is a fine thing), but because they can’t imagine alternatives. Often, they end up rationalizing this lack of imagination (a bad thing) as lack of ambition (which can be piously spun as a holier-than-thou “good thing,” as in quitting the rat race and feeling superior to paycheck types).

We need a meaningful way to talk about long-term career planning for free agents, a way that allows for apples-to-apples comparisons with paycheck careers. And obviously we can’t use variables specific to paycheck jobs, like “title”, “budget” or “number of reports,” OR variables specific to free agents, such as “number of clients” or “bill rate.”

I made up a construct that I think works — a leverage graph. It is based on the observation that the unifying feature of both free-agent and paycheck careers is that if you do well, you land in situations with increasing leverage, via relatively discontinuous jumps. These jumps are promotions in paycheck careers, and new types of gigs in free-agent careers.

Let’s understand the concept in paycheck career terms first, since it is the more familiar and legible case. Here is the leverage graph (green line) for a typical high-flyer paycheck career:

I’ve left the term leverage undefined, but it is loosely anything that shapes the actions of the company beyond your individual work output. So individual contributors might produce something that is used by others in the company. Managers raise or lower the productivity of everyone under them based on how good or bad they are. Leverage is closely related to knowledge. The more you know and understand, the more you can consciously engage in leveraged behaviors with bigger consequences. Leverage is how knowledge turns into power over the organization’s fate. So a leverage curve is a big brother of a learning curve.

Here’s how you read this graph:

1. Each smooth curve is a learning curve with a single leverage type; the jumpy green curve is a leverage curve for an individual career that jumps across leverage types.

2. This diagram illustrates successful career paths with at least a little lifelong learning, but obviously people can and do “plateau” on a long S-curve or crash

3. Each smooth curve has slowly compounding gains over a single-leverage-type career; higher curves have faster rates of compounding leverage

4. The default curve is the solid line (individual contributor); you can stay on so long as you maintain a minimum acceptable performance for your experience level

5. The managerial curves (black dashed) are not default, but not exceptional either. There are systematic ways to get on them and stay on them.

6. The executive leadership curve (blue dashed) is exceptional, and crosses the other three. There is no systematic way to get on it or stay on it; you have to hack your way onto it.

7. There is a leverage distribution on each point of each curve. Not everybody on the same nominal smooth curve with the same years of experience has the same leverage.

8. Managerial curves feature normal leverage distributions at every point. Exceptionally good and exceptionally bad performers both tend to be weeded out.

9. Individual contributors and executives have non-normal leverage distributions. While exceptionally bad performers tend to be weeded out as on the managerial paths, exceptional stars (“10x” types) can persist and grow in their roles.

10. True promotions are leverage-increasing jumps across curves, and to be distinguished from grade-progression promotions within each curve.

Leverage in Paycheck Careers

The leverage graph should be familiar and easy to parse for people with some work experience, but here’s an illustration.

For engineers, for example, there are generally two recognized career paths in big companies. The first is a path as an individual contributor rising from an entry-level role to one with a title like “Principal Engineer” or “Fellow,” marking deep expertise in some area. The progression is often marked by a system of grades, such as 1-10. At Google, for instance, the two star celebrity engineers, Jeff Dean and Sanjay Ghemawat, are the only “Level 11” engineers among thousands at the company.

This path can play out across multiple companies within an industry that share a technological base.

The second path is a technical manager path, where you rise from individual contributor to some sort of general line management role, via an intermediate role in project or workgroup management. The difference between the two is whether you manage other managers, or whether you manage individual contributors (a crucial distinction that is central to management theory, but not critical for free agents to understand deeply unless you consult on organizational psychology problems). This path typically tops out at some level that is internally recognized as just short of an executive (aka business-risk-owning) role, such as an “Associate Vice President” or “Director.” The titles don’t matter. What matters is that leverage increases across and within curves.

Leverage (and compensation) can continue to increase after the company runs out of titles and grades to hand out.

Along either path, exceptional people tend to get picked out and groomed for executive leadership, but unlike progression through individual or managerial grades, the process is not systematic.

Engineers who rise to executive roles typically do so by showing a capacity for risk-taking leadership early in their careers, pulling off high-stakes projects that others didn’t think possible. This marks them for fast-track grooming for leadership, customized roles, and customized compensation packages. “Executive” roles typically begin with VP titles, but again, don’t take titles too seriously. It’s the substance of the role that matters — participation in the risk-taking of the business being central to the job.

The career paths in other functions such as sales and marketing are similar. Career paths in what are known as “staff” functions like HR are somewhat different, in ways that make this leverage graph view less useful.

Leverage in Free-Agent Careers

Now that we have the familiar paycheck career case established for reference within this leverage graph framework, this version for free agents should be easy to read.

Since most people bank a few years paycheck work experience before embarking on free-agent careers, the story begins at a non-zero quit point on the x axis. This is anecdotally around 5-10 years, though it is rapidly falling, and many younger free agents are skipping a paycheck world bootcamp altogether, either out of choice or necessity (which has consequences good and bad — they lack traditional organizational literacy, but also have fewer bad habits of thought to unlearn).

The big difference between the paycheck and free-agent versions is the nature of the leverage represented by the y axis. For paycheck types, it is budgets, number of reports rolling up to them, and participation level in strategic decisions. For free agents, it is informal influence in their economic sector. This difference leads to a particular portrait of the four smooth leverage curves a free agent must navigate:

1. The solopreneur is the equivalent of the life-long individual contributor, who slowly gets exceptionally good and increasingly unique at something. Their leverage lies in being the loci of accumulation for industry-wide best practice knowledge.

2. The thought leader is someone whose work directly influences the work and choices of others. As the derogatory jokes suggest, this is the equivalent of your basic project or workgroup manager within the corporation. The thought leader is the pointy-haired boss of the gig economy. Their influence is exercised in a diffuse way through public writing and speaking, and the production of artifacts (such as open-source programs or influential terminology) used by others. Their leverage lies in being the trusted loci of consensus formation around key trends, standards, and evolutionary choices in an industry.

3. The guild leader is someone who begins to take on something of a market-making role within the gig economy, helping people find gigs, making key backroom connections, and doing a degree of event organizing and community building. To the extent there is a need and opportunity for any sort of collective action, they catalyze it. Note though, that the incentives are wrong for them to play union-leader type roles, because the gig economy, especially above the API, is fundamentally an economy of unrepentant scabs who side with capital by default. The collective action takes other forms. Their leverage lies in being loci of network capital accumulation.

4. The mover and shaker is someone who can genuinely influence the course of events in an industry through the force of their personal reputation alone. An example is Linus Torvalds. He can shape the vast universe of Linux with his personal opinions, and exercise influence at a level similar to the CEOs of big tech companies. Their leverage lies in being the loci of extra-institutional agency based on connections to ground reality unmediated by large organizations.

Besides this big difference in sources of leverage, the free-agent leverage graph also has one other key difference: In the paycheck leverage graph, typically the curves are mutually exclusive. Managers rarely continue to do individual contribution work. Executives rarely spend a lot of time directly managing.

In the free-agent version though, this is not true. As I’ve illustrated with the forking green path, you often have to keep doing the work of the lower level curves even as you take on work on the upper levels. This means, at any given time, you’re exercising many different kinds of leverage simultaneously. Often this happens across the multiple gigs you might be doing at any given time.

For example, let’s say you’re doing 4 gigs at once:

1. In Gig 1, a solopreneur gig, which you got based on your paycheck resume, you’re applying a technical skill that the client lacks internally but is common in the industry.

2. In Gig 2, a thought leader gig, which you got via a viral blog post, you’re applying models and ideas unique to you to a specific challenge faced by the client, perhaps by delivering a workshop.

3. In Gig 3, a guild leader type gig, you’re helping a young startup new to a market map the environment, navigate crucial meetings, hire talent, and structure external relationships.

4. In Gig 4, a mover-and-shaker type gig, you’re sparring with a well-known executive, helping them make decisions that you know will set precedents for the industry and make the news.

Depending on the percent of time you’re devoting to each of these, and the amount of money you’re making from each, your role in the gig economy is some sort of superposition of the four curves. While people in paycheck roles do sometimes spread themselves out this way across projects, typically, they tend to play the same kind of role in every project.

So now that you have a construct for thinking about your career as a free agent, the question you have to ask yourself is: where are you, where are you headed, and where do you want to be headed?

One of the running themes in this newsletter is that indie consultants serve as shadows to the client principals they work with, especially leaders. To serve well in this role, it is important for indie consultants to learn to identify real leaders accurately, by a robust and useful intrinsic definition rather than by titles. Here is mine:

A leader is someone with a high level of individual agency within an organization, with responsibility for an independent connection to external reality.

For those who like Boydian jargon, a leader is simply someone who owns their OODA loop. Or more precisely, they own the risks of their agency and decisions.

I tend to only work with leaders by this definition. Not because I’m a snob, but because it is the easiest, most robust situation, and I’m lazy. Your job as an indie consultant is to get inside the OODA loop of the “client” as an ally, and help advance their goals. This is easiest when the client is a single person rather than an illegible ghost in the organizational machine.

Identifying Leaders

A leader is someone who can directly judge and use any thinking or work they sign off on. They are not intermediaries accepting counsel or advice on behalf of other individuals or groups, and sending it up or down a chain of command (or into the blackhole that often exists deep inside large organizations). They are not applying inflexible standards controlled by others that they lack the discretion to override.

When you work through non-leader intermediaries, there is high risk that you will end up doing the wrong thing, or doing the thing wrong.

For example, perhaps you do work for a low-agency middle manager who is sourcing a report that will be presented to the CEO. The CEO will actually sign off on the report, declaring it good or bad, but you never get to meet them while doing the work. In such a situation, the chances of things going wrong are very high. Your chances of getting stiffed on the payment go up. The likelihood that you’ll get thrown under the bus and blamed for failure goes up. The chances of reputational damage go up.

All these risks can be mitigated and managed, and it’s possible to craft good gigs out of such situations, but it is neither easy nor particularly fun. So it is best to work directly for leaders when you can.

A true leader will acquire and maintain control of as much financial agency they need to do what they think is their job, including the ability to pay for other people’s time and labor. If they can’t acquire this agency, they will typically leave.

This means for an indie, a leader is also someone who can in practice determine entirely on their own whether to pay you, even if they nominally need someone else to sign off. Being recognized as a leader within an organization means your funding requests within your domain are not typically challenged. So you, as an indie, only have to make one person happy.

Leaders include executives by default, and others (such as uniquely skilled individual contributors) by exception.

Trust, but verify, that the defaults hold. You might find leaders in unexpected places, who are a pleasure to work for, or you might find that someone who walks and talks like a leader, and has all the right titles, isn’t actually a leader in any meaningful way.

Finally, don’t go by size of organization a leader runs. Leaders may or may not have a large number of reports “rolling up” to them, but they tend leave as much of the direct management work to others as they can.

Having to directly manage a lot of people directly weakens leadership tendencies, and strong executives tend to limit that to a few direct reports, so they can focus on leading. They encourage high-autonomy organizations where people need little management.

This does not mean they neglect people working for them. It just means they have a laissez-faire approach based on high situation awareness, strategic intervention behaviors, and strong inspection and monitoring habits. Like good teachers, they seem to have eyes in the back of their head. They are able to get the behaviors they want out of the organizations they lead without micromanaging or spending all their time in meetings with reports.

But their focus is on leading, not managing.

Working with Leaders

Within the idea of an indie as a shadow, there are two aspects to working with leaders, an opposed aspect and an integrated aspect. In areas where the leader is still growing, you occupy a somewhat opposed role, where you are growing as well. In areas where they have integrated personalities (where they have “eaten their shadow”) you have to occupy a much more aligned role, and you need to be integrated in complementary ways.

The net effect is something like being an evil twin. The “evil” part is the opposed growth aspect. The “twin” part is the integrated aspect.

Sparring work in particular, is about managing the tension of these two aspects of work. This means your ideal client is someone who is mature in the same ways you are, and growing in the same ways you are, just from the “other side.”

When this condition is not met, elements of coaching (teacher/learner) dynamics enter the sparring work. I personally tend to avoid this, again because it makes things harder. Being cast as a teacher or student in a consulting relationship means there are mis-aligned learning curves to navigate, in addition to the actual work of the gig itself. This introduces additional risks into the gig: they may like the work but be disappointed in your performance as a teacher or student. Or vice versa.

Again, the risks of learning curve elements can be mitigated and managed, and as with working for organizations instead of individuals, it’s possible to craft good gigs out of such situations. But as in that case, it is neither easy nor particularly fun. So it is best to work directly for evil twin leaders when you can.

Opposed Aspect Work

For the opposed aspect (where you’re growing together), the shadow aspect of everything positive associated with leaders is often a visible part of the perception of consultants they work with.

• If leaders are missionary, their indie consultants are mercenary

• If leaders are idealistic, their indie consultants are cynical

• If leaders are holy warriors, their indie consultants are pragmatic operators

• If leaders are charismatic stars, their indie consultants are grey blurs

• If leaders are taciturn doers, their indie consultants are voluble talkers

Generally only indies can truly play this opposed role. Consultants from larger firms don’t relate individually to leaders in the same way. Instead, the self-shadow relationship holds at an organizational, firm-to-firm level.

This default shadow role means the default perception of an indie consultant showing up in an organization is negative. This is why it is important for indies to be conscious of their halos. Consciously managed halos are how you counter-program default negative perceptions (created by the shadow position). You will never completely counter-program it, and that’s not a good thing to aim for anyway. You just want to be perceived in a way that allows you to be effective. You don’t need to be universally liked or admired within the organization. It’s okay to be in the shadow zone.

That said, in rare situations, the default perception of an indie consultant is positive. If the principal has a terrible reputation, then people supporting them can sometimes end up with positive perceptions, as foils who mitigate the negative traits. These are not good clients to work for generally.

Basically, you are the evil twin in the relationship by default, but if the principal is obviously seen as evil by everybody, you might be seen as good.

Integrated Aspect Work

If you have a passing familiarity with Jungian psychology, you’ve probably heard something along the lines of self-actualization being about “eating the shadow” or “integrating the self.”

This means, as (and if) they grow and become more self-actualized, leaders and their indie consultants start to resemble each other in key ways. Each begins to integrate their personality in complementary ways to the other.

This is why it is important to primarily work with clients you admire and respect. You are their shadow, but they are yours too. Either both of you grow, or neither of you does.

But while working in areas of shared growth is fun, working in areas of shared maturity is even more fun.

The biggest such area is being right. I got the idea from the Amazon leadership principles (a rare non-vacuous document of its kind) that includes this one: Good leaders are right a lot. You can actually make a triad of such statements:

• Good leaders are right a lot

• Good managers win a lot

• Good employees accomplish a lot

It is crucial to recognize that leadership often means being right but not winning. This is because leaders own risks they don’t entirely control, which means their game is more like poker than chess. Even with perfect play and no mistakes, they might lose.

By contrast, managers tend to control the risks they own, and play more deterministic games, so it is appropriate to judge them based on their win rates.

And down the hierarchy, non-leader individual contributor employees are typically judged on effort and output, whether or not it is winning output, or output that is right about a lot. That’s called doing your job, within the inner reality of the organization.

For an indie consultant working with a strong leader, striving to be right a lot, in ways that are complementary to ways in which the principal is right a lot, is the most important area of aligned, integrated work.

• Good leaders are right a lot. Good indie consultants are right a lot.

There are several other areas where leaders and their consultants can be aligned and integrated, but this is the most important one. They have aligned gut instincts, and are therefore right a lot in complementary ways. When they disagree, chances are, there is either incorrect or missing information in the picture, or an analytical error somewhere. So it is possible to have an important and interesting discussion that gets somewhere, instead of a futile argument that runs aground on fundamental misalignments.

A recurring theme in this newsletter is that gig work is shadow work. One of the subtle consequences of this is that the gig economy is extremely fragmented and arbitrary in structure and behavior. Once you get past the broad 3-way distinction among indie consultants, contractors, and platformers, the detailed structure of the terrain is really hard to map out. Generalizations and narrative threads are for the mainstream paycheck economy. The gig economy is defined primarily by the glitches, exceptions, and incoherencies of the mainstream paycheck economy.

Our messy map is the reason their suspiciously clean map doesn’t fall apart.

The gig economy is the part that’s been swept under the rug. It is the set of patches for the mismatch between the map — the institutional landscape with its org charts and job descriptions — and the territory of economic reality. That’s why the gig economy is by definition also the shadow labor economy. And no part is more shadowy than the indie consulting part.

I took a shot at making a map of indie consulting as a shadow zone. This is a draft beta version that I intend to refine and label/annotate properly in future versions. It is meant to suggest broad contours, not exhaustively cover every sort of indie consulting you could do. I’ll explain the overall logic, and then drill down into a few of the markets to illustrate.

The map reflects the fact that indie consulting is the messiest and most shadowy of the three subsectors of the gig economy. Why?

• The contracting subsector inherits the structure of the paycheck workforce via extension/augmentation. Every contractor in principle could be converted to a regular employee in a simple way by extending or re-scoping the org chart.

• The under-the-API platformer subsector has a structure dictated by platform architecture and various algorithms that handle tasking and coordination.

• But the indie-consulting world? No structural forcing function, but a great deal of shadow energy. Which is why you end up with a picture like the one above.

In the map above, the x-axis represents the level of client principal you serve, the main person you deliver to, who signs off on your work. The y-axis is the basic category of consulting offering: skills-based, process-based, or strategy-based. The distinctions are the obvious ones:

• A skill is anything learnable that you can improve with practice, and acquire prowess at. If you can win a grade or excellence award at it, it’s a skill.

• A process is anything that primarily needs some sort of basic procedural literacy, and conscientiousness, rather than talent to do well. If it doesn’t take much practice, and you can earn a certification for it, it’s a process.

• Strategy is anything that relies on insight rather than prowess or conscientiousness. If you can earn an illegible reputation for it, but awards and certifications for it are cringe, it’s strategy.

Now the thing about this 3×3 grid — shown as light dashed lines — is that it’s tempting to identify each “square” as a clean-edged role you could play. Unfortunately for us, the gig economy does not allow for such clean boundaries.

Each of those squares is actually a typical paycheck role (likely occupied by your client). For example, executive leadership + strategy = CEO, executive leadership + process = VP, Human Resources, executive leadership + skill = CFO (I’ll leave the other 6 boxes for you to fill out as homework).

But our map is based on ways in which their nice map fails to actually cover the territory it is expected to cover. So each indie consulting niche is like a fragmented country on this map. It has a main coverage region, but also a bunch of scattered outposts.

There are 10 offering-based markets on this map, but I won’t attempt to describe all of them in detail, only the ones I have some experience of.

Insight-based Indie

I’ll start with my market. As an insight-based indie, mainly offering things that get labeled “strategy,” most of what I do is in the top right corner, and is delivered through 2 kinds of offerings: sparring and investigations.

But not all of what I do is in that corner, and I don’t cover all of the needs of that corner. There are isolated spots of sparring and investigation required in the “skill” row, and some bleed-over into the “process” row (for example, OODA-related things I do often bleed into the middle).

One of the reasons strategy offerings for executives is so dominated by “sparring” relationships is that leadership is famously and visibly a lonely, solitary kind of work. So the primary “shadow” need is actually intellectual company that can keep up. As a result, much of what is delivered in this corner is delivered through sparring style interaction, even though the content can be hugely varied.

Skill-based consulting

This is probably the most crowded market on the indie consulting map, and the place where most younger entrants into the gig economy start out.

It tends to include anything that is adjacent to an individual contributor skill. I very rarely operate in this market, but when I do, I make sure it is something I deeply enjoy doing hands-on, and typically don’t bother about billing time accurately. I’m happy to spend more time on this kind of thing than the client might think reasonable, to get it right by my own standards and curiosities.

One way to think of this market is that it can be described via prefixes like pre-, post-, meta-, para-, or infra- attached to individual contributor paycheck employee roles.

For example, (software) architecture skills are a kind of meta-development (the real architecture part, not development title-inflated to architecture). So an actually skilled and experienced Scrum trainer would fit into this market.

Design skills are a sort of pre-product development skill. You won’t be doing all the detailed engineering or design work, but you might be crafting the broad approach and creating the design space for the adjacent employees to work with.

Often this kind of consulting builds up a foundation, capability, or starting condition in a short period and then hands it over to regular employees to run in production mode. Either that, or it is a transient “special projects” type need that does not need sustaining once it’s achieved its objectives.

Notably, you deliver via a skill, but not to the adjacent-role individual contributor paycheck employees who will eventually take over, or even their managers. For maximal impact, you must deliver to executive leaders who own the risks of the initiative (if you’re delivering to another locus, chances are, the project will fail).

Sometimes you can turn skill-based consulting into strategy content for individual contributors, via a blog post or a talk for instance, in the square dominated by business book writing. Other times, you might coach individual contributors briefly, especially in hand-off processes. But in general, you should be selling to executives, either to get some new risky initiative off the ground, or as a special project.

Managerial Indie

A harsh truth about hierarchical organizations is that the amount of room shrinks as you go up the corporate ladder. This means a lot of indies start out mid-career when they find they’ve hit some sort of ceiling and can’t get promoted, but are too bored or frustrated to remain at their current level. Or they’ve just been laid off. So they go sideways and turn into managerial indies.

Managerial indie offerings are typically things that require a degree of managerial experience and skill (and often based on something they first learned to do as an employee), but are primarily based on conscientious delivery. A dead giveaway is that you offer the same thing to many clients, with little to no modification. If it can be labeled a “best practice” it can be a managerial indie offering.

Stuff like workshops and retreats are the bread-and-butter for this kind of indie, and often this attracts the most bureaucratic types who crashed out of their paycheck careers through cluelessness. In the indie world, this cluelessness can sometimes turn into an asset, since it comes with an infectious enthusiasm that can charm clients despite being borderline cringe. On the flip side, on occasion, when clueless types clue up, they can often get radicalized and resentful, and turn to grift — and nothing is easier to turn into a grift than a managerial indie offering. They know how organizations work, and are pissed off enough at society at large to use that knowledge against the world.

As a result, a lot of managerial indie consulting work is offerings that are more theatrical and CYA than impactful. But when these offerings are crafted and delivered well, they can be very interesting to do, and valuable to get as a client.

I’ve done this sort of thing occasionally, but frankly I don’t enjoy it, and am not conscientious enough to do it well, especially repeatedly without much change. The exception is when it’s a workshoppy topic that lends itself to very high customization and context-dependent redesign for each client. So it’s essentially fun each time, and has strong skill or strategy components to it.

One special type of offering in this market is troubleshooting. Experienced managers who were once skilled individual contributors are often the best troubleshooters for tricky, highly specific problems that confound employees without the right experience. If this were a common type, it would be a market in its own right, but typically so few people do this well, they tend to present as regular managerial indies, but with a “fixer” or “bagman” footnote to their nominal reputations.

Functional Expert

Finally, there is the functional expert. It can be hard to tell this kind of indie apart from the managerial indie, since both are typically mid-career and process-focused. The difference is that the functional expert typically brings seasoned individual contributor abilities to the party, rather than managerial, and delivers to individual contributors rather than managers.

Often this involves experience with highly domain or industry-specific tools (such as SAP) that are not taught in schools, and have to be learned on the job. The presence of specialized tools means that compared to the manager-indie market, there is some resistance to bullshit. But don’t trust that too much. It is possible, just harder, to sell a lot of bullshit tooling, and training for that tooling.

This is a type of consulting I’ve never done (I have no relevant skills of this sort), and never want to do, but have seen close-up a lot.

One “tell” of this type is that they go to industry conferences a lot, and all know each other within a given geography or market. They are the most heavily networked of all indies, and present a guild-like brand. There’s a good chance they’ve authored an O’Reilly type book.

Other Markets

To wrap up, the 6 markets I didn’t cover in detail (due to a mix of limited knowledge and limited interest) are:

1. Coaching: Anything involving 1:1 soft or meta-skills training and mentorship for individual contributors that is typically not available in schools and can’t be learned from books alone. Coaching qua coaching is typically an early career market. So-called executive coaching is, I’m increasingly convinced, 90% either sparring, or therapy in disguise. The rare specialized coaching you need at executive level, such as media-training, is usually procedural rather than strategy or skill-based.

2. Psychology, motivation, and testing: Highly adjacent to the managerial indie market, but with a bigger skill component. Stuff like non-violent communication, motivating employees, active listening, Myers-Briggs. You can often earn premium-mediocre credentials in this market that are somewhere between certifications and actual hard skills.

3. Trend report/analyst work: This is probably the most legible kind of indie consulting work and is the most “researchy” kind of offering. It also has the biggest moat for indies, since it takes serious time, effort, and network capital to produce. Which means you’re most likely to get this kind of work via an intermediary analyst firm. Or you burn up savings producing it on spec, hoping to sell it once you’re done.

4. Regulation, compliance, legal, media: Self-explanatory. Any kind of indie consulting that involves pragmatically navigating an arbitrary and complex external maze. Unlike the adjacent workshops/retreats market, this market is created by 3rd parties like the government or media forcing your clients to do something.

5. Airport business books: It is hard to sell “strategy” offerings to individual contributors because of the impedance mismatch. Strategy work costs time and money to produce. That’s why you can bill 4-10x as much for sparring work as for coaching work, and why analyst reports go for thousands of dollars. The only way to make money off individual contributor interest in strategy matters is via a mass product: a book typically. But this category includes anything that can be sold indefinitely via distribution (including recorded workshops, materials, and workbooks).

6. Ethics: I’m breaking this out as a separate market even though it’s tiny and usually absorbed in one of the adjacent markets (sparring if you want to think seriously about hard ethics conundrums, compliance if you just want to comply with the letter of ethics regulations enforced by the government or other external party).

There is a lot to be said about all these markets of course, and my own direct experience of most of them is fairly limited. As I said, I’ll be refining this map, and perhaps in the future inviting guest contributions to cover parts of it where I’m weak.

Jobs provide a ready-to-inhabit psychological home-away-from-home that a mere portfolio of gigs does not. Home, sweet office, as a refuge from home, sweet home. In a good political and economic environment, this is not very important. If your gigs are enough fun, and the local Starbucks or other “third place” is open, you might not even notice that you lack a psychological home for work. Not everybody is a homebody at work, or wants to be.

But when the economy and political environment go bad, being in the gig economy is like being caught outdoors in the middle of a winter storm. Then you notice. Suddenly, being indoors in a nice job offering home comforts seems really attractive. It’s not even really about the money. It is about having an intact social reality to inhabit.

I’ve been trying to come to terms with this sense of being caught outdoors in bad political-economic weather. I made myself this little iPad painting to contemplate.

I’ll explain the picture in a minute, but some more general thoughts first.

Gig Economy Weather

Under normal conditions, when the economy and political environment are healthy, being in the gig economy is like being outdoors in a park in nice weather, with a picnic basket, and a clean bathroom nearby. The sun is shining, squirrels are running around. Birds are chirping. You don’t miss home, and in the moment, it seems like being outdoors is an obviously nicer situation than being cooped up indoors, at least for you.

Interactions with clients feel like they are happening across a window ledge: they are indoors, you are outdoors. You’re both happy with your choices. Indoors or outdoors is a matter of lifestyle tastes.

When the political and economic environment are really nice, you even get a whiff of a yearning for the outdoors from clients (I got this feeling sometimes in 2013-15). They are mildly envious of your freedoms. There they are, trapped indoors within the limited reality of a single organization, while you are free to participate in many realities in many organizations, and also to enjoy the broader economic outdoors with personal projects, writing about larger macro trends, and so on. That’s what good times in the gig economy feel like.

These are not good times. Lately, I’ll admit, in meetings with clients, I’ve found myself feeling mildly envious that they are indoors, within largely intact private social realities, while I’m outdoors in the midst of an unraveling public reality, facing the full fury of the politico-economic elements without a roof and walls around my work.

Dulce Domum

We are so used to thinking in terms of the work-vs-home dichotomy that we often lose sight of the fact that work is in fact a home-away-from-home. In a job, it almost always is literally so. You have a desk, or even a room to yourself, with access to kitchen facilities, bathrooms, and a bunch of people you probably like — your work “family” so to speak. If you work for a particularly paternalistic company like Google, there might even be good food, places to nap, a game room, and laundry. It might even be better than home.

In the gig economy, this home-like feeling may or may not exist. Perhaps you have a coworking space and regular lunch buddies. Perhaps the friendly Starbucks barista substitutes for the friendly coworker; someone you say hi to every day.

This feeling of being home-at-work (HAW) is important. More so than work-from-home (WFH). It allows us to relax, and trust the work environment to supply a certain amount of both material and social comfort. It provides a thoughtfully mediated sense of connection to the broader world. It fosters a productive and generative state of mind.

This is the sweet-home feeling, dulce domum. For work, perhaps we should call it dulce officium, the sweet-office feeling (my Latin translation might be off, but I’m sticking to it since I like the sound of the phrase).

What is this feeling like?

In Kenneth Grahame’s classic, The Wind in the Willows, there is a moving chapter titled Dulce Domum, where the two main protagonists, Mole and Rat, are making their way back from yet another crazy adventure on a cold winter night. They pass through a village with many people comfortably ensconced in their warm homes:

But it was from one little window, with its blind drawn down, a mere blank transparency on the night, that the sense of home and the little curtained world within walls—the larger stressful world of outside Nature shut out and forgotten—most pulsated…

Then a gust of bitter wind took them in the back of the neck, a small sting of frozen sleet on the skin woke them as from a dream, and they knew their toes to be cold and their legs tired, and their own home distant a weary way.

Thus primed to yearn for home, as they exit the village, Mole catches a whiff of his own home nearby, which he’d abandoned several months earlier, disgusted with chores and cleaning, to go adventuring. He is overcome by a powerful homesickness, and is inconsolable until the two of them find their way back to his home and spend some time there.

If The Wind in the Willows were a story about the gig economy, the village would be a business district full of offices full of people happy to be away from home, and the adventures of Mole would be gigs. The dulce officium moment would be a sudden yearning for a regular job, with lunch buddies, malfunctioning printers, and running gripes about bad coffee.

I occasionally get a whiff of that feeling now, when I peek into the lives of paycheck people, through client meetings or otherwise. They are secure in their warm jobs, inside organizations with their inner social realities largely intact, even if the material realities of work-from-home regimes have made the home-at-work feeling much messier.

For people with secure paycheck jobs, the reality of Covid19 has not yet fully hit, and possibly never will, no matter how long they work from home.

They are able to immerse themselves in the pleasant reality distortion fields of their jobs, within which the pandemic has been aestheticized and processed into a business crisis, complete with recovery strategy meetings. Hardship is of a familiar corporate sort — budgets cut, pay cuts, travel and events canceled.

Organizations do these things in the face of every crisis, so there is a certain ritual familiarity with the response pattern, if not the stressor. Paycheck employees are at home in their responses. Dulce officium.

You’re Exposed

Dulce officium is not the case for the gig economy. The much flimsier work-homes we construct for ourselves, out of a favorite table at Starbucks, lunches with friends, and occasional meetups, have fallen apart.

Even if your cash flow and gig work routines haven’t been impacted — mine largely haven’t — the overall sense of being home at work has evaporated. I definitely feel exposed and outdoors. So should you. In the gig economy right now, any sense of security is a false one, unless your talents naturally turn towards profiteering off black-market PPE supplies or something.

The main reason, of course, is that if you’re in the gig economy, strategizing the recovery is not an optional spectator sport for you, consisting largely of tracking what the CEO is doing. It is an unavoidable imperative, fraught with real risk.

You literally have to think for yourself right now, because it is nobody else’s job to do so. If you don’t, things could go really badly for you. Already, almost by instinct (which is a result of nine years of experience), I’ve made several quick, tactical moves that turned out to be really wise. I’d already be in trouble if I hadn’t thought of them, and moved very quickly to do them. Like the rest of you indies, I have no paternalistic organization prompting me to do the necessary thinking and acting, and no concerned manager asking after my welfare. So this is not idle speculation.

This political-economic environment really is dangerous.

You really are exposed.

Lack of tactical and strategic foresight will cost you.

Newbies have to be extra careful — lack of experience navigating uncertainty increases your chances of making bad errors.

For an employee in a stable organization, there may be some tough times, but trusting the leadership to do a good job navigating the crisis might actually be a reasonable option. If you think your employer will be among those that will crash and burn through the crisis, but you have solid marketable skills in job-like domains, you might still be able to avoid strategizing the recovery for yourself. You could simply look for a new job with an organization that seems set to recover strong.

Of course, this is also an option for some in the gig economy. I’ve already heard of several giving up and heading indoors to jobs. But for many, it is either not an option (you might have marketable skills, but just not in a job-shaped package), or you don’t want to. A little bit of both apply to me. My skills don’t fit jobs, and a part of me is convinced that “whatever doesn’t kill me makes me stronger” in this environment.

If I can make it through this thing, I can probably make it through almost anything. So despite the unpleasant political-economic weather, the challenge appeals to me.

A Mood Map of the Future

Let’s talk about the picture at the top. It’s a mood map of the future.

There’s of course a lot of very specific forecasting, mapping, and maneuvering you can and should do relating to how your particular corner of the gig economy is responding to the crisis. But underneath those practical tasks, there is a more important emotional self-regulation task you have to tackle: dealing with the feeling of being outdoors in a harsh environment, without an economic “home” to work out of.

You have to assess the general mood, your own mood, assess whether the fit is a positive one that lends you agency, or whether you need to work on your own mood (since you can’t affect the general mood outside of a small, local zone).

This is not an environment that will be kind to depressed listlessness and weak motivation.

I’ve tried to map the general mood in the picture above.

To the left of the 2020 vertical line, there is a diffuse but defined mood. It is a patchwork of red, yellow, and green (which signify what you think they signify). Against this backdrop, the futures of individual organizations are evolving, with much stronger internal reality-distortion field moods created by things going well or poorly. Each forking tube is a reality distortion field evolving in time.

To the right of the 2020 vertical line, the mood is not so much good or bad as it is undefined. Like in those movies set in simulated worlds where the character runs to the edge of the simulation and discovers an empty grid. It’s not good or bad. It just isn’t.

The future we thought we were inhabiting has been trashed. The future that we are creating right now is largely undefined, still very much under construction.

There’s a few defined red, orange, and yellow patches, but not much green. But mostly it’s empty grid space.

There is enormous opportunity in this lack of definition of course. It means the future is waiting to be invented, and as a free agent, you have more ability than most to participate in that invention. But there is also enormous risk and anomie in that lack of definition. That grid-like outdoors is a stark space, bereft of that lovely home-at-work feeling that normally keeps you going. No dulce officium there.

If you’re outdoors in this gig economy, this is your element. An undefined grid with patches of danger, and very little by way of soul-nourishing at-home comfort. You can peek in through Zoom windows at people enjoying such comforts, like Mole and Rat in The Wind in the Willows, but you’re not one of them.

Don’t let their sense of security contaminate your mood. They can afford it, you cannot. You need to maintain a much higher degree of alertness.

If you’re indoors, there’s a good chance (to the tune of 60% of businesses in California according to a news report I just watched) you’re with a stable employer, whose inner reality can actually withstand the collapse of the outdoor grand narrative, at least for a while.

Of course, if your employer was already in bad shape, there is a good chance it’s on the verge of crashing and burning.

The green-turning-red thin line outside of the corporate “reality tunnels” is a typical free agent trajectory in this environment. The green and red lines inside the tunnels are the trajectories of paycheck employees in organizations that are surviving versus failing respectively.

You’ll notice I’ve illustrated a fork in the futures of the 3 surviving organization. If an organization isn’t being killed by immediate existential threats, it is at least facing a range of possible futures. Some have a narrow range, some have a wide range.

The point of this map is not to make specific predictions, gesture at specific environmental realities, or suggest specific maneuvers and strategies. The point is to become sensitized to the mood of the environment, your own mood within it, and how it relates to the distribution of environmental risks and opportunities.

Specific predictions can go wildly wrong. Maps can be inaccurate. Maneuvers may fail. But the mood of the party is generally unmistakeable, and the mood you bring to the party is the biggest determinant of whether you weather the storm, whether it drives you indoors, or whether it destroys you.

So for the time being, there’s no dulce officium for you. Just a challenge to survive and thrive outdoors in bad weather.

Independent consulting and independent investing share some tantalizing similarities. Both involve direct risk-taking, without an organization providing a safety net for you. In both, you have to strategize about returns that are not strictly causal functions of effort (ie you have to wrangle luck). Both are activities that inhabit a larger open-world economy of macro-trends and forces where you can try to go to where the action is, instead of waiting for the action to come to an organization that employs you. Both are unlike paycheck employment in that it is hard to blame others for “unfair” consequences. You have to own the results of your actions, good or bad.

But there are two crucial differences.

First, for investors, the primary input is capital, while for consultants, the primary input is time. Second for investors, the primary driver of returns is exogenous events, while for consultants, the primary driver of returns is the quality of your own actions.

Basically, as a consultant, you primarily create or destroy value directly, as a result of your efforts. An investor on the other hand, primarily banks profits or losses due to creative destruction happening out there in the economy.

As an example, take conducting a workshop versus executing a trade based on some information. A significant part of the returns from a workshop depend on the workshop itself being good or bad. For a trade on the other hand, the returns are good or bad depending on how the world actually behaves. You might have set up a technically perfect trade, but lose because the world does something else. Or you might have set up a sloppy trade, but the world does something that makes it a winning move anyway.

One clear way this difference shows up: As a consultant, you tend to win big when you do good, smart work that opens more doors, drives referrals, brings in more interesting and lucrative gigs, etc.

As an investor, you tend to win big when the world does stupid things. Legendary trades on Wall Street tend to happen in the context of crashes and meltdowns, where a minority presciently bet against the world.

Investor World vs. Consultant World

Let’s capture these ideas in two graphs representing the investor world and the consultant world respectively. In both cases, there is a curve of proportionate rewards and losses (yellow-orange) where value is created or destroyed based on the quality of your effort (smart/stupid) and a curve of serendipitous/zemblanitous (“surprisingly lucky” vs. “unsurprisingly unlucky”). Here the red/green curves are the net return curves — the proportionate returns plus the effects of unexpected good or bad luck.

Here we’ve assumed a convex (what Nassim Taleb calls antifragile) world for both the investor and consultant, with increasing-returns upsides, and bounded-losses downsides. But the x-axis is different for the two cases. For the investor, the x-axis represents severity of positive or negative events relative to the logic of the trade. For the consultant, the x-axis is smartness or stupidity of the effort.

In both cases, we’ve assumed a synchronization in the crossover points for both proportionate consequences and luck effects.

The difference between the two worlds, as illustrated is twofold:

• The x-axis is different (event quality vs. effort quality)

• Relative proportion of proportionate returns (orange-yellow) in net returns (red-green)

(of course both event and effort quality apply to both, but I’m not about to plot a 3d graph here for what is already an outrageously cartoonish model)

As you can see, very little of the gains or losses of the investor can be attributed to the creative, causal effects of the trading actions. Trades do not create or destroy value by themselves (unless you’re a market mover like Warren Buffett, whose trades are read as “smart money”, implying quality, resulting in a premium). They allow value to flow from one part of the economy to the other, usually with a degree of entropic loss along the way.

Now that we have a basic picture in our head, let’s examine some varieties.

Four Consulting Regimes

It is useful to carve up consulting activities along two axes: whether the environment is one of scarcity or abundance, and whether the consultant’s own actions are strategic or not.

Strategic is not the same as smart. Strategic means you’re taking advantage of being a free agent to constantly discover or create opportunities for yourself that would not be open to you as a paycheck employee confined to a single company. So for example, if you do a good project whose results are public, you can parley that into getting more gigs of the right sort at a better rate. Regardless of their strategic abilities, paycheck employees are limited in their ability to act strategically by the limits of their environment.

Here’s the 2×2:

There are four regimes here:

• Non-strategic and scarcity: you’re exposed to non-convex conditions and high downside zemblanity risks. There will be little luck for smart effort, and highly compounded negative consequences for dumb effort (eg: drain your savings and then get hit by a health crisis with no safety net).

• Non-strategic and abundance: conditions are nice, and you might enjoy a little luck with smart effort, and your downsides will be capped. Overall, it’s not that different from being a paycheck employee. Your gains and losses are just exaggerated a bit, due to higher exposure to luck forces. You’re neither benefiting too much, nor suffering too much, for being in the open economy instead of in the safety of a paycheck job.

• Strategic and scarcity: The curve looks very similar to the diagonally opposite non-strategic/abundance quadrant, but here, there’s a chance you’re doing much better than paycheck employees at bad companies. You’re leveraging your freedom and strategic imagination to reshape a potentially default bad returns curve into a good one.

• Strategic and abundance: This is what we’re all shooting for, a regime that’s unavailable to paycheck people, where net serendipitous returns on smart effort grow, even as the proportionate rewards get smaller as a fraction. If you go sufficiently far to the right, the proportion starts to look like the profile of investing activity. Your time becomes as good as money.

In my 9 years so far, I have spent significant periods in all four quadrants. Net, I’d say my average situation has been strategic-and-scarcity, but with some delightful periods of strategic-and-abundance.

In the scenarios above, we’ve continued to assume synchronization: that the world will get lucky or unlucky in lockstep with your actions getting smarter or stupider. This is of course the most unrealistic assumption.

In general, the crossover points for the “luck” and “proportionate rewards” curves won’t coincide. To steal a term from the printing world, there will be a registration error (the term comes from situations like printheads being misaligned, leading to different colored inks being laid down differently, leading to weird artifacts at edges).

Misregistered Worlds

Let’s talk about worlds with registration errors. There are four kinds that you should be aware of (not on a 2×2 though):

• A stupid-lucky world is one where whether your efforts are smart or stupid, you still win overall. The net returns curve stays safely above the x-axis, and a nice green band keeps you above zero returns. You actually have to think hard to find ways to lose.

• A perverse world is one where smart effort actually leads to net mounting losses, while stupid effort is rewarded with net increasing gains. Be careful about jumping to the conclusion that you actually inhabit a perverse world. Most of the time, when the world seems to be acting perverse, it’s your assessment of smart/stupid in your actions that is backwards. That, or you’re being gaslit by someone with an agenda. Perverse worlds are actually rare. You’d be surprised how often people code their actions backwards because they can’t tell stupid and smart apart, and therefore project it as perversity onto the world.

• A pure dystopia is the opposite of a stupid-lucky world, where whether your actions are smart or stupid, the proportionate gains and losses are always swamped by overwhelming bad luck. There is always a red band of pain, and you’re always underwater, taking net losses.

• Finally, bahramdipity refers to a world that is fundamentally serendipitous, but malign forces try to kill the serendipity. This means that up to a point, positive smart effort will still lead to negative returns. But if you push hard enough, you might overcome the malign forces and start winning. So there is an effort deadzone where there is a proportionate positive return (the little yellow wedge near the crossover point) that is swamped by a negative environmental drag.

There’s a lot more you could do with these effort/return diagrams and parsing of luck effects vs. proportionate effects, but I’ll stop here. I’ve already built a rather wobbly edifice here, on the strength of a rather shaky analogy between investing and consulting.

Ultimately, the graphs and notional varieties are just scaffolding for thinking about luck, smarts, strategy, and environments. If you don’t like thinking in terms of convexity and effort/event vs. returns curves, you can reframe it more simply as a set of lessons about how best to invest in yourself. So I give you…

Consulting Like an Investor: Seven Principles

1. Independent consulting is like independent investing, except that you’re investing time into the quality of your own efforts rather than capital into beliefs about events in the world.

2. Going independent is giving yourself permission to be strategic, and putting yourself in a playing field — the broader labor market — with opportunity for strategy, just as investing is putting yourself into a broader financial market than your local bank.

3. Because you’re primarily investing time rather than capital, strategy is about quality of effort you put into your creative output, not the nature of events.

4. The winds of good and bad luck are often, but not always, synchronized with the smartness or stupidity of your actions. Be attuned to this synchronization state.

5. Strategy is a lot more consequential under conditions of scarcity, to reshape default bad into default good returns curves, but the relative positive returns of free agency primarily accrue when you figure out how to be strategic in good times. Strategy under scarcity makes survival as a free agent possible. Strategy under abundance makes survival as a free agent worthwhile, and preferable to paycheck employment.

6. Being strategic is not the same as your efforts being smart. Smart vs. stupid is about what you do within a gig. Strategic vs. not-strategic is what you do between gigs.

7. The world is often in a state of misregistration, and you have to be sensitive to four kinds of environment in particular: stupid-lucky, perverse, dystopian, and bahramdipity. Inhabit stupid lucky worlds if you can, and bahramdipitous ones if you must. Get the hell out of perverse or dystopian environments as soon as you can. 80% of strategy is putting yourself in the right environment. 20% is about what you do there.

For the tenth time in ten years, yet again I find myself about to make what is perhaps the most strategic decision for an indie consultant: where should I live? And this time, I think I have to make the decision very differently. This is because the right answer used to depend on one big variable that swamped everything else: the potential for casual coffee meetings. This potential of course, has been destroyed by the pandemic.

The decision is basically this: should you pay a premium to live in an important business hub (typically a major metro), with a major airport? Or should you save on costs by living somewhere cheaper and more remote?

What exactly is the value of being able to take a lot of casual, serendipitous, impromptu meetings with potential clients? And how does this equation change due to the pandemic-related travel freeze, both in the short and long-term?

I won’t bury the lede: I ran the numbers for my own practice over the last 9 years, and 70.3% of my consulting revenue can be attributed to gigs that started out as casual coffee meetings, while 26.2% closed online. Here’s the pie chart (I consolidated 17 small clients with billings under 5k, and amounting to 3.5%, into one small pie slice):

So the headline is crystal clear: at least my kind of consulting practice is hugely dependent on gigs that start out as casual coffee meetings. Here is a more detailed breakdown. Look at the clients tagged A and B in particular.

The clients tagged A began with in-person, casual-coffee-meeting encounters, while the B clients are ones I closed after purely online interactions (including phone/video calls) and negotiations. Some of these, I have never met in person.

The Cs are 8 clients with total billings of 1k-5k each, and Ds are 9 clients with total billings under 1k (typically one-shot spot consults). Almost all of the Cs and Ds are online-only closings, but I haven’t bothered detail-coding them as such, since they’re pretty much a rounding error on the headline: 70% of revenue starts with casual coffees, and four of the top five clients started out that way.

Edge Ambiguity

As you can see, 4 of the top 5 clients started out as casual coffees first. In fact, the picture is even more dramatic than it looks because B1 and B2 are actually edge cases, and if I include them in the A list, the proportion changes to 83% casual-coffee first, and 13% online closings, and 6/6 of top 6 gigs by revenue (81% of the total) being casual-coffee first.

Both these edge cases have interesting anecdotes attached that shed light on how deals close.

With B1, I’d almost closed the deal based on email and phone interactions, and they had even sent their contract for me to review before I met the principal. But then the project got delayed by several months due to client budget issues.

But here’s the thing — by the time I actually closed the deal, I’d had a serendipitous coffee with the principal when we both happened to be in the Bay Area at the same time.

And to add to the edginess of the case, I’d actually met with a secondary person for coffee (not the sign-off person but one of their senior peers in the organization) before we even got to the contracting stage — and that person had been specifically deputized by the principal to meet with me and check me out. So really, B1, which represents 7.63% of my revenue, could be an A.

B2 is interesting in a different way. I’d done a small writing thing for this client (under 1.5k) first, but the bigger gigs only happened after I ran into a bunch of the people from the organization at a conference, after which they sent a series of larger projects my way. So that too could reasonably be called an A gig.

Whether you code revenue type liberally or conservatively, the lesson is inescapable: my kind of indie consulting begins with casual coffees. And there’s a good chance yours does too.

Let’s layer some ethnographic color on the numbers.

What’s a Casual Coffee Meeting?

A casual coffee meeting is a low-planning, low-stakes, opportunistic meeting without a great deal of marginal effort to make it happen. Pre-pandemic, I used to take 3-4 such meetings a month, of whom 1-2 were potential clients, and 1-2 others (like readers with no consulting potential, or young people looking for advice).

Casual coffee meetings happen in one of four ways typically, here’s a breakdown of my top 6 by this logic:

1. They happen to be traveling where you live (A2)

2. You happen to be traveling where they live (A1, A3, B2)

3. You both happen to be living in the same place (A4)

4. You both happen to be traveling to the same place (B1)

This low-effort is important, because it means if nothing comes of it, it’s still an upside meeting: all you did was have an interesting conversation over coffee without any significant investment of marginal effort. My rule of thumb is: a 20-minute Uber-ride away from something you’re already doing.

If you have to go to a great deal of trouble to meet, with marginal effort of say > 1 hour drive for either of you, it is no longer casual. It is a planned, in-person encounter.

Interestingly, this applies even if you’re the one doing the schlepping and the potential client has zero marginal effort. Because the very fact of the schlepping sends a costly signal of how much you want the gig, which could be a good or bad thing. On the receiving end, one time, when I was going to city X, someone emailed me asking to meet — but they were planning to take a 4-hour train ride just to meet me. I said no. That’s way too much pressure to create value.

Of the four modes, types 1 and 2 are typically routine business travel between hubs. Type 3 is all about local meetups and socializing. Type 4 is typically conference travel, often to exotic locations where nobody of business interest actually lives.

Let’s talk about conferences and business trips (types 1, 2, and 4), because they’re pretty much down for the count at this point.

Traveling Exurban Encounters

The good news is: conferences per se don’t matter much. In fact they don’t matter at all, at least for my style of consulting.

You’ve probably encountered a principle of networking along the lines of “most interesting things at conferences happen in the hallways and break areas between sessions.”

This has not been true for me.

Meetings at events, with others who are also attending the event, have not been useful for me. In fact, I’ve never had a gig come out of meeting someone I didn’t know before at an event.

Literally never.

Make of that what you will.

I think of encounters within an event, between participants, even outside of sessions in the break areas, as the suburbs of events. When I look at gigs I landed by going to conferences, they happened not at the event itself or its suburbs, but at meetings I pre-arranged on the side, outside of the event proper. Typically with people who happened to live or work in the city, and weren’t actually attending the event.

Usually I did this by adding a day before/after the main event for tourism, to take additional meetings, usually by dropping in at people’s offices, or cafes away from the event venue. I think of these meetings as happening on the exurbs of events. The event is at best your excuse for being in a particular city, not a direct catalyst.

What’s more, as an indie, going to conferences as an attendee, especially as a paying attendee, weakens the exurban casual-coffee potential of going, whether in the suburbs or exurbs. The ideal way to go is as a speaker, with at least your travel costs paid for by the organizers.

Why?

Say you pay $3000 overall to go to a 2-day conference. Travel, accommodation, registration. If you’re a real hustler, and add an extra day, you might be able to fit in a dozen coffee/lunch/dinner/drinks meetings around the event (suburban and exurban).

Assuming the event itself is actually useless, and there’s no value there that you can’t get from the videos later, amortizing your cost over the supposedly “casual” coffee meetings, each meeting has a cost of $250. So the expected outcome value should be at least that to make it worth it. The math works for people in sales or bizdev roles for other organizations, but not for people paying their own way.

And even though nobody explicitly does this kind of math when deciding whether to take meetings, the perception of high marginal cost is there.

Which means it’s not a casual coffee meeting at all.

This is post-hoc analysis for me. For years, I’ve had a policy of basically never paying out of pocket to go to a business conference (social/cultural conferences are different). I only go as a speaker or panelist, with paid-for travel costs, and only to places I actually want to go to as a tourist anyway, preferably with my wife.

Conferences are actually bad for lining up gigs even in an exurban way. What works even better is the exurbs of business trips for existing clients. This puts the cost perception firmly in the positive zone: you’re there making money, not spending it.

Here suburban encounters are meetings with other people in the same large org, which might lead to unrelated parallel gigs (happened once for me) and exurban encounters are with unrelated people at other organizations that just happen to be in the same area (several gigs happened this way).

Of course, all of this is down for the count right now.

What about in-hub encounters?

In-Hub Encounters

What about the value of simply living in a business hub and running into people who also live there?

Again, the direct value is probably near-zero in the median case. Being a scenester and going to a lot of meetups and things is not a great way to get gigs, because the extent of your ongoing effort investment is visible enough that “casual” coffee meetings that come out of these have a high perceived marginal cost.

Though I’ve lived in several hubs (Washington, DC, Seattle, Los Angeles, and at a stretch, Las Vegas back when it had pretensions of becoming a Zappos-driven hub), I’ve basically never gotten into the local meetup or coworking type scene for business purposes. Any meetups I’ve attended or organized have been social, for my blog readers typically. Most local 1:1 coffees have been social, with no expectation or potential for gigs.

Basically, almost nothing big of interest to indies happens as a result of investing in semi-structured “business scene” activity (meetups and such). The yield is simply too low, because these “scenes” are disproportionately full of people looking for gigs and opportunities rather than people with gigs and opportunities to offer. There is an air of I’ll-take-anything desperation and thinly veiled precarity. It is not a good environment to close money deals.

The one significant in-hub gig I landed (A4) was actually mediated by a mutual friend, and the client in that case was only a part-timer in my city (the mutual friend was in the other city). We met up for casual coffees several times before I landed the gig, and these happened during the part-time visits by that client to that city. The slight time-pressure of limited in-person meeting windows made these closer to business-trip exurbs meetings than in-hub meetings.

The Broken Pre-Pandemic Gig Funnel

I think everything I’ve said applies to anybody doing a relatively high-level sort of knowledge work, with weak structure and ambiguous expectations and high 1:1 trust required.

So if you put it together, what can you conclude from this analysis?

1. The bulk of indie revenue can be attributed to casual coffees

2. Casual coffees are encounters with low marginal cost around existing activity

3. These mainly happen in the exurbs of travel business/event travel

4. In-hub encounters are much less important than people imagine

5. Actual participation in “networking” events has little to no effect

6. You need to travel, live where others travel, or both, to catalyze casual coffees

7. If you live in a remote, non-hub, cheap place, you must travel a lot

8. If you live in a high-traffic, high-cost hub, you need to travel much less

This is the pre-pandemic indie-casual-coffee funnel. It is how I — and many like me — used to generate gigflow.

The bad news: this thing has been shot to pieces. Certainly for the next year. Possibly for the long-term.

The good news: if indeed there is an emerging alternative model to doing indie work based on flipping the ratio of casual coffee leads vs. online-closing leads, you should be able to run it from remote hubs where costs of living are much lower.

But we haven’t figured out the how.

And in the meantime, I have to consider a bunch of different apartment choices in the next month, and pick a place to move to before my current lease runs out.

Do I bet on remaining at a hub location — downtown Los Angeles — and betting that normal activities resume fairly quickly? Or do I slouch off to some cheaper location, where costs of living are thousands to tens of thousands of dollars lower, and figure out a whole new playbook?

I’ll let you know what I end up doing after I do it.