Category: art of gig

In the first two parts of my ±10 years look at the evolution of the gig economy from my own 10-years-in perspective, I looked at the 2 lowest layers of the stack: workflows and trust. The third layer is what I think of as the money layer. It is for free agents what the management layer is for the paycheck world.

What did the money layer look like in 2011? What does it look like in 2021? What might it look like in 2031?

These are not the questions you might think they are. It’s not about your money, but about money in general. What is it? Where it is? Who controls it? Where is it going? How does it flow? How is its fundamental nature changing?

You should be curious about these questions, independently of what seems to be the main selfish question: how to get some of it?

As a free agent, you live dangerously at the assembly language and API level of money, not safely at some high-abstraction level. You can’t afford to have the passive, disinterested (or even slightly contemptuous) attitude towards money paycheck people often have. If you don’t develop what I call a “money-positive” attitude, you risk both failing to make money, and developing unhealthy and fearful attitudes towards it. Just as, if you’re an employee, if you don’t get past disinterest and contempt and develop some curiosity about management, and a “management-positive” attitude, you’ll fail to advance. You’ll be reduced to seeking solace in Dilbert cartoons.

So you can’t treat money as a spectator sport. You have to develop a genuine, intellectual curiosity about money that goes beyond your personal needs.

But I don’t mean the kind of interest that bankers and investors have. I mean the sort of interest detectives and forensic accountants bring to their work. Like them, you can follow the money as a source of personal economic intelligence to guide your gig economy activities.

Following the money means understanding money the way you understand the weather and climate.

The weather is the low-level details of transactional flows, while the climate is high-level macroeconomic shifts. Each by itself can be misleading, but together, they can help you follow the money.

Let me illustrate with myself as an example.

Money Weather, 2011-21

If you’re primarily used to getting money via direct deposit, and spending it via checks and credit cards, with things like PayPal and Venmo being “play money” on the side, the transactional complexity of the open economy can come as a shock to you. It’s as different from the paycheck money-flow world as outdoor weather is from indoor weather (to continue our parallel, management activities inside companies are like indoor weather control — adjusting the HVAC system and so on).

One of the most interesting ways to develop intuitions about following the money is to pay attention to how you’re paid at the level of transactional details, learning why things work the way they do in different industries, and developing preferences for being paid in certain ways. It’s like picking the sort of weather that suits your temperament.

Early on, you should aim to get paid in as many different ways as possible, so you learn about weather patterns and develop a sense of how they might be shifting. And you should always be willing to experiment being paid in a new way, unless it looks illegal or scammy.

Tracking how you are paid is to money what going outside and looking at the sky is to the weather. It reveals a lot about the client, the industry, and the local economic culture. Tell me how you are paid, and I’ll have some pretty good guesses about what sort of gig-work you do, and in what part of the economy. You probably can guess better than you think as well.

See if you can infer the “story” behind my history of payments below.

The first time I got paid, it was via paper check. I was paid mostly with paper checks for the first couple of years (and conscientiously saved the paper stubs like they were trophies). At some point, I got paid against a “purchase order” (PO) for the first time. And also got paid late via an invoice that somehow got “lost” for the first time.

At some point, most clients started paying via credit card. Even though I was set up to receive credit card payments from the beginning, it only became popular a few years in, reflecting changes in the infrastructure, environment, and who I was working for.

At some point, wire transfers started becoming more common, initially for international clients (and I had to get used to SWIFT codes), and then domestic. Sometime around 2013-14, payment via services like bill.com started becoming common.

For a gig in 2017, I was supposed to be paid in crypto tokens, but the company kinda “forgot” and since it was a small amount I didn’t bother pursuing it. I think that was also the year I received a paper check for the last time.

One big company I have worked with for the last 4 years has a really solid and futuristic self-serve automated model for dealing with POs and payments that I genuinely love. Once I year I do a big invoice with them, and immediately get an email from a partner firm called C2FO, offering immediate payment (instead of in 60 days) in exchange for a small discount that they calculate based on current economic conditions. It feels very futuristic. I’ve never had to avail myself of the discounted early payment offer, but it’s nice to know it’s there. It’s like high-end payday loans (and unlike payday loans the rates are reasonable). More such mechanisms are coming online.

One time, I was paid for an hour of consulting with… a pair of shoes.

This year, for the first time, I am accepting part-payment in stock options for a gig. It’s not an uncommon thing to be offered, but it is uncommon for the offer to be worth the trouble to accept.

I’ve paid a lot of my own subcontractors via PayPal, but can’t recall an instance of accepting money via PayPal. I feel that makes me part of the gig-economy middle class. PayPal has become something of the working-class transaction layer. It’s fine for occasional gig-economy dabblers, but a PITA for full-timers. Real indies use Freshbooks and integrate with Stripe. Using PayPal marks you as not quite serious.

Stripe has been a huge game changer in the plumbing of the middle-class free-agent world. It set up a whole parallel universe of financial plumbing, and a big chunk of my consulting income, and all my non-consulting income began flowing through it at some point.

Stripe and Paypal now also offers loans against cash flow analytics, without the bureaucracy associated with getting lines of credit at traditional banks, or the high interest rates of credit cards.

I never noticed it while it was happening, but the landscape of financial flows has shifted slowly but decisively under my feet, to become more automated, more electronic, more seamlessly international, and with much better risk and credit management. And at all scales from POs worth tens of thousands of dollars, to small transactions on the order of $5. Even for solo free agents, the cost of capital has come down sharply, though I’ve never needed it (nothing I’ve attempted to do so far has required any capital outlay bigger than the cost of a computer).

It’s almost like when I started out, it was in a primitive financial wilderness, and now it’s a well-paved urban built environment. In part, I’ve moved to a better corner of the economy. In part, the economic environment has changed.

Why is it important to pay attention to these things? Because often you get early warning about where things are headed based on these low-level details.

And often, the mechanics of transacting with a company can give you clues about its economic destiny (if you’re curious about why, look up Coasean economics). In 2021, you should be eager to work with companies that pay you in sophisticated, low-friction ways, and be wary of ones that involve a complex exchange of physical paperwork and end up mailing you a paper check. Following the money means following lower transaction costs.

Can you tell from the details above what the higher-level story of my money-making evolved? It’s like tracking someone through the woods based on footprints.

Money Climate, 2011-15

If the transactional environment is the weather, the macro-environment is the climate. To follow the money thoughtfully, you must pay attention to both.

In 2011, when I went free agent, the world economy was just beginning to limp out of the global financial crisis (GFC). At least in the United States, money was not yet flowing freely through the economy. Corporate budgets were still tight, with restrictions in place. In 2011, it seemed obvious that despite the “recovery,” the GFC had changed the world in very significant ways.

Banks had just been bailed out, and the economy was getting used to weird new phenomena like “quantitative easing” distorting the money supply in ways people were still not used to.

Silicon Valley had only recently started recovering from the effects of the dotcom crash a decade earlier, with a new wave of “2.0” companies that was yet to demonstrate viability. People were wondering: would it create another bubble and crash, or was this a more sustainable arrival?

I asked myself: Where is the money?

Specifically, the discretionary, liquid money that was not already spoken for, and might be available for me? The answer I came up with was:

1. Governments had money

2. Banks had money

3. A few big old companies had money

4. Silicon Valley had money

5. Ordinary individuals had some money

Straight off, I decided I was never going after government money via things like grants. Governments always have money, but it is always painfully hard to get at any of it. And it always comes with vast amounts of baggage, but few interesting risks you can meaningfully participate in. I might be willing to jump through a few hoops for a government gig at unique places like say NASA, but that’s it.

I also decided I was not going to go after individuals (via business models like personal coaching). As an established blogger, I had an advantage in reaching ordinary individuals, but “consumer consulting” was not really a meaningful idea in 2011. Neither the infrastructure, nor a culture of individuals paying individuals in their private capacity for consulting-like services, really existed back then.

There was no “direct to consumer” market in consulting, so to speak (this would change). Consulting was something you sold primarily to businesses above a certain size.

That narrowed things a little. I was after open-market, private sector money. But that was still too broad. I also decided that while I would be open to old economy and financial sector money, I would not pursue it.

That left Silicon Valley, or “tech money.”

I’ve been associated with the scene for a long time now, and am generally considered a “tech insider,” so this might seem weird, but in 2011, coming from the East Coast, this was not an obvious move. As a mechanical/aerospace engineer by training who had worked at Xerox, it was by no means the obvious conclusion that I should head towards the tech scene on the West Coast and try to find a foothold there. I was already 36 at that point, so not exactly young.

But in 2011, it seemed obvious that software was going to eat the world, and that the tech economy was slowly going to turn into the whole economy.

It was equally obvious that old economy companies were either going to go into decline-and-harvest mode, or into fraught “digital transition” attempts, most of which would fail.

Which meant, whether or not I had anything to offer, I had to position myself primarily in relation to Silicon Valley. That’s what following the money meant in 2011.

I did it physically. First we moved from Washington, DC to Las Vegas in the summer of 2011, and then from Las Vegas to Seattle (aka Silicon Valley North Annex) in 2012, after briefly considering and rejecting the Bay Area proper.

My bet paid off. Being located on the West Coast put me right next to the biggest, most free-flowing rivers of money in the world at the time. I began getting and closing more leads, mostly from tech companies, though not necessary on the West Coast — people from everywhere involved in tech tended to pass through all West Coast cities frequently back then. If you think of potential clients with money to spend as walking around with dollar signs on their foreheads, in 2011-15, they were all constantly passing through Seattle and the Bay Area (Portland and Los Angeles developed as significant tech hubs a little later).

I also learned a few things:

1. Startups were eager for consulting help but had little to no money

2. Growth-stage companies had money but were generally not operationally set up to handle consultants outside of very specific, targeted “special ops” needs

3. Large tech companies generally had anti-consultant cultures, unlike large East Coast old economy companies.

4. Investors had money, and were open to spending it on consultants

It took a couple of years, but I eventually developed enough of a strong network (see my previous newsletter) that I was able to plug in to the money flows of the tech economy fairly reliably, if not predictably. By 2014, I had worked for small startups, medium startups, large companies, and investors.

I was inside the tech scene, and perhaps more importantly, seen as being inside the tech scene. I had followed the money to its source.

Money Climate, 2015-20

Sometime around late 2014, I sensed a disturbance in the force. Flows of money were beginning to shift around me… again. Specifically:

1. Private equity (PE) money was becoming a bigger deal in tech

2. High-Net-Worth Individual (HNWI) and “family office” money was growing fast

3. The big platform companies were starting to behave like old companies

4. Investment money was pooling at the extremes — seed money, or growth money, with the middle slowly starving

5. Money was starting to seriously flow into climate and sustainability tech

6. Software was eating healthcare and bioscience, creating another large flow of money to follow

7. Money outside of Silicon Valley wanted to be like money inside Silicon Valley

8. Ordinary individuals had money and there was growing infrastructure to get at it

While I didn’t specifically try to follow these shifts in an explicit way, I began to keep an eye on them and staying informed, and saying yes and no to gigs in ways that reinforced my exposure to flows I wanted to drift with.

Often, the biggest source of intelligence was the mix of leads I was getting, whether or not they turned into gigs. After factoring out the effects of my own evolution, the rest was priceless intelligence about the economy.

Towards the end of 2015, I began consciously following the evolution of the sustainability and energy sectors, and thanks to a couple of new gigs, was able to start following that trail. To a lesser extent, I began following money in healthcare, and landed a few gigs in healthcare tech as well. That’s on the back-burner for now, but I might pursue it more actively in the future as it gets more interesting and moneyed.

Today, I say yes to tech gigs only if they are technologically interesting, and trying to push computing frontiers in somewhat fundamental ways. I no longer like gigs that simply run known Silicon Valley playbooks against new opportunities, or push existing technologies in incremental ways. I’m more likely to say yes to climate and energy gigs — that’s a big flow of money that’s only getting bigger with every passing year, but the sector also interests me because it is doing some of the most technologically interesting work happening today.

I used to be wary of PE money, and would often treat PE-funded status as a red flag in leads, but have grown increasingly comfortable with it. There’s PE and there’s PE. There’s the vultures, and there’s the bold turnaround operations. Some of the most interesting things these days happen neither at public companies or venture-funded companies, but at PE-funded companies.

And boundaries between PE, VC, and ordinary corporate money have started to blur anyway.

Money Climate Change, 2021-31

In the next decade, once again I sense vast shifts in the offing at both the weather (transactional) and climate (macrotrend) levels.

As I mentioned earlier, this year, for the first time, I accepted part payment in stock options for a gig (generally a bad idea — if they’re offering equity participation to consultants, it is unlikely to be a good startup).

One of my clients just IPOed via a SPAC.

One of my larger clients last year was some strange hybrid of a VC firm, PE firm, and family office.

The world’s financial hydraulics are changing yet again, as they do every decade or so. Never a dull moment when you live in the open economy.

The post-Covid economy is going to be… weird. In ways I can’t yet see. I feel like a beginner again, as should you.

The West Coast is also going through some sort of cyclical maturation late stage. “Tech” is getting dispersed around the globe, so it is harder to see what it means to “follow” the tech money. Life was simpler when you could simply physically move to where the action was. On the other hand, online pathways have become much better. Media like Twitter and now Clubhouse offer ways to “follow the money” virtually. In 2011-15, the “VC blogosphere” was a big deal, but that’s pretty much dead now.

The “Direct to Consumer” market, which in 2011 I dismissed as not a real thing, has finally emerged. With Stripe, and the “creator stack” of the “passion economy,” you can now sell things that look and feel kinda like consulting directly to consumers (or employees acting in their private capacity, with or without corporate reimbursement). This newsletter, arguably, is me selling consulting in an aggregated way to individuals, in a form factor that would have been highly inefficient 10 years ago. Depending on what you teach, online courses can be a form of consulting.

The cryptoeconomy also shows signs of maturing, and evolving from primarily an investment sector to a transactional sector. Expect to get paid in usable tokens in the next few years, and it being not such a weird thing.

Will I have to pack up and move physically once again, following the money? I will almost certainly not stick around in Los Angeles more than a few years. But where to next?

I don’t yet know. But this time, it will only partly be about following the money.

As I’ve grown somewhat more financially secure, I now have some freedom to solve for things besides money. That could of course change in an instant. All it takes is a few bad quarters, a major economic crisis, and some bad luck to go from feeling like you’re in a secure position to feeling like the world has collapsed around you. It’s happened before in my lifetime, and it will happen again. You think you understand the weather and climate, and then get blindsided like Texans did last week.

There is no permanent security to be found in the money layer of the world, but there’s always interestingness, and a general curiosity about money — but short of obsessive maximizing tendencies — tends to pay off. It’s part of our world, and it’s an interesting thing that rewards study both intellectually and by flowing towards you.

Money flows are never still. While ancient rivers of money always keep flowing robustly, they do change course slightly. But new rivers of money are always emerging, and fragile ones drying up. And the nature of money keeps changing.

In absolute terms, the oldest rivers tend to contain the most money by volume, but also the least money in terms of accessibility. Money in ancient rivers tends to be very stable and spoken for, and requires a lot of work to access. Money in newer rivers is easier to access, but is also liable to shift suddenly on you, so you have to stay on your toes.

Following the money has been quite the ride for the last decade. I expect it to be even more of a ride for the next decade.

Last week, I kicked off my 4-part series to mark my tenth anniversary as an indie consultant with a look at the past and future of my workflows at the inbox level.

Workflows are the lowest layer of the consulting stack. The level at which Fingerspitzengehfühl (“finger-tips feeling”) operates. I like to think of workflows as the embodiment of your trust in yourself. Intra-personal trust if you like. In this second part, I want to take a similar ±10 years look at trust between you and others, or interpersonal trust. For indie consultants, this is primarily trust between you and clients. This is the second layer of the stack.

How Trust Actually Works

Indie consultants tend to be highly conceptual people. So we tend to model interpersonal trust in ways that are too abstract, like game theory (prisoner’s dilemma anyone?), crypto-like “proof of work,” or “trust signaling” through devices like a clear personal manifesto on a website, a list of values, or a curated bunch of gushing testimonials speaking to the virtues of a fictionalized version of yourself.

If you go down that road, the risk is not that you will fail to build trust, but that you will succeed at building a sort of ersatz, dehumanizing “artificial trust machine” that “works” in the sense of making money, but turns you into an increasingly commoditized and packaged offering. At best you will turn into a “trusted personal brand” within a clearly circumscribed market niche, rather than a trustworthy person living and working in a world of other humans.

What’s the difference?

• A trusted personal brand represents a clearly specified and bounded promise, and a demonstrable record of delivering against it consistently. A trusted personal brand lowers risk on some close-ended front.

• A trustworthy person it is worth trusting — somebody it is interesting to take risks with in an open-ended way. They increase your capacity for risk, and win or lose, you will be left feeling enriched rather than betrayed.

Not that there’s anything wrong with wanting to be a trusted personal brand. If that’s what you want, by all means go for it. If you play it right, and get a little bit lucky, you’ll make more money in a year than I have in ten, and move on from this level of the game entirely.

But the deeper reward of being an indie consultant is the chance to forge yourself into a trustworthy person in a fully human sense — but on a larger scale than most humans will ever enjoy. Everybody has a circle of coworkers, friends and family within which they are viewed as trustworthy or not. Indie consultants have a shot at a more public sort of trustworthiness in the open economy that goes beyond such local, personal circles.

This trustworthiness is condition that magically leads random distant strangers to reach out to you, and take on risky, uncertain challenges based in part on your support and promise of fellowship.

I like to think of it as projecting “spooky trustworthiness at a distance.” It’s my substitute for sales and marketing.

The “distance” of course, is distance on a social graph. Like between dwarves and elves in Middle Earth.

When it works, spooky trustworthiness at a distance opens up a world of optionality for you, where epic adventures can be had. Adventures where you won’t be the hero or heroine, but the shadow of fascinating heroes and heroines. What I’ve been calling shadows’ journeys in previous posts.

This requires an approach to trust that may feel awkward and unfamiliar at first.

Spooky trustworthiness at a distance rests on an individualized, anthropological understanding of how your actual gigs actually come about — or fail to. Trust, in other words, lies in the truths contained in a collection of stories that you start building with your very first client. It eventually turns into a sort of personal ethnography, or thick description, of the interpersonal dynamics triggered by your visible, available presence in the world of work. You are supply. The story of demand for you is a story about trust.

In my case, I can identify a sort of three-act arc in the ten-year story.

Act 1: Trust Ramp-Up

Here’s a quick tour of how I ramped up with the first few clients, and how trust developed in each case:

1. In February 2011, I got my first two clients off of Quora. Strangers who decided to trust me on the basis of my answers to questions on a public site. These were sparring gigs. The amounts were small, but the confidence boost was huge (thanks Gene and Mat!)

2. I got my third client in June 2011 via friends at a PR firm I had hired for a project at the job I had just left behind. It was a medium-sized strategic marketing writing gig. Though I got along fine with the client and was paid directly by them, the trust equation never really extended past my friends. It was a subcontract pretending to be a contract.

3. In early 2012, I landed my first big gig, my fourth client, for an analyst report project. It came via a reader of some of my enterprise software blogging (back in 2009-12, I was briefly blogging for the Enterprise 2.0 blog). It did not go well, due to misaligned expectations that didn’t become clear until the eleventh hour.

4. My fifth client — who I still work with, and is now my oldest client — cold-approached me in 2012 on the strength of my Gervais Principle series of blog posts. I’ve now worked with him across four senior executive roles at different companies, and I first developed 80% of my bag of tricks working with him.

The interesting thing is, at the time (2011-12) I could not easily tell what was working. But it was quickly clear what didn’t work well — my unhappy fourth gig taught me that initial trust must be converted to working trust by getting expectations aligned and crystal clear early on. But not through painful and structured conversations seeking “alignment” or clarifying “expectations.” That’s a waterfall approach to trust that basically never works because you just don’t know each other well, and end up making ritual noises. Instead, you do it by iteratively setting and delivering on small, bite-sized goals that get larger and larger.

Alignment and expectations are not things you define at each other, but things you learn about each other iteratively, possibly adapting and compromising along the way.

If all trust in a gig is actually “trust debt” linked to a big, uncertain deliverable outcome, you’re setting yourself up for trouble. Do not mistake a pleasant, collegial relationship for working trust.

Working trust is primarily a learned, shared, and genuinely felt confidence in the mutual acceptability of future work output before it is delivered.

This is a weird definition of trust — and one that I’m writing down for the first time, though I’ve operated by it for ten years. So what I learned in Act 1 is that there’s actually 3 elements to trust, with working trust being the most important:

1. Discovery trust: you trust the pathway that catalyzed the relationship, whether it is a chain of referrals, or a social object like a blog post. It is tempting to rely on credentials for this, but that doesn’t work. Credentials are filter criteria, not trust criteria.

2. Commitment trust: you establish enough 1:1 rapport to sign a contract that you feel good about, without too much scrutiny or a lingering sense that you might potentially get screwed over.

3. Working trust: you learn to trust each other according to expectations that have been aligned by iteratively learning about each other early on.

In Act 1, I experienced four kinds of discovery trust across five clients in two years (trust via mediated readership, trust via referral, trust via subcontracting, and trust via direct readership).

Commitment trust was always the same — the contract only got signed after I met in-person with the client and had a chance to establish rapport. That’s all it was — a test for a kind of shallow capacity for simply getting along during a low-stakes meeting.

Here is a contrarian opinion: it’s not worth getting too clever or careful with contracts. If you find yourself doing that, you’re attracting the wrong kinds of clients and losing at the game of becoming a trustworthy person. Most of the real risks in interesting gigs cannot be captured in contracts no matter how clever you get.

Early on, I just made up my own one-page contract and have used it for the majority of my gigs. When the client wants to use their own contract for whatever reason, I give it a quick once-over for typos and obvious mistakes, and just sign. If I find myself hesitating or wanting to argue minutiae, I back out. You cannot fix in the contract what is missing in the commitment trust level.

Working trust was the hardest to learn. The first year convinced me to avoid “working trust debt” (it’s like technical debt in software), and instead build working trust early and aggressively — in my case by specializing in what I call a sparring approach to consulting. This is of course not always possible. Many types of consulting are built around big deliverables and a lot of back-loaded risk. You have to figure out your own approach to mitigating that.

Act 2: Track Record

After those first five clients, I settled into a pattern. I had a non-empty track record, and always had 1-2 active clients going, even if billings were at a trickle. Though nobody has ever asked for references to past clients, the fact that they exist and are credibly listed on my website seems to make a big difference, both in clients’ ability to trust me, and in my own confidence in how I present myself. A track record is not really about the verifiable list of gigs you point to. It is about the confidence you project and inspire due to that list existing.

My slowly growing ability to do this kicked off, somewhere in early 2013, a second act in my adventures with trust.

The fact that I was mentioning a consulting practice in my writing and talks without sounding apologetic, or like I was faking it, and clearly not starving on the sidewalk, seemed to create the beginnings of an aura of trustworthiness.

Starting around 2013, almost all my clients came via my own blog: direct, inbound leads. The majority — perhaps 70% — tended to reference the Gervais Principle as their reason for reaching out to me. A few came via a couple of other lightning-rod type bits of writing. Interestingly, almost none of my leads came from my few attempts to write “content marketing” type lead-gen content.

Referrals, which accounted for 2 of my first 5 gigs (and probably more than 60% of my revenue over that period) became vanishingly rare, and stayed that way. I’d say they now track at around 1% of leads, and maybe 5% of closes. This was very surprising to me in the early years. I’d expected referrals to play a bigger role, and even made some half-hearted efforts to catalyze them. But apparently, the kind of trustworthiness I operate with is not very transitive.

Act 2 lasted perhaps 3 years. In terms of the three kinds of trust:

1. Discovery trust: was increasingly being established by my own visible online presence, mainly my writing, but speaking gigs played a small but crucial role. I was real! There was video evidence! I was not a dog on the internet!

2. Commitment trust: remained the same — the in-person rapport meeting remained key to establishing it. I’ve never had to change the approach I adopted in Year 1.

3. Working trust: increasingly I was only doing sparring work, which besides many other benefits, has a sort of pay-as-you-go trust learning structure. There is never any trust debt, and no nasty surprises lurk in distant deliverables. I’m only as trustworthy as my last sparring session.

Along the way in Act 2, in 2014, I did a year-long stint with Andreessen-Horowitz, a gig I think of as a charismatic megagig that significantly reshaped trust perceptions for me.

Charismatic megagigs are are important, and you should try and land a couple. They are what turn a strong but commodity track record into a differentiated one that marks you as the only person who can do certain things. I think I have 3 such on my record, though only one has a significant public aspect.

It proved to be an interesting milestone, since it added a sudden sharp spike of glamour and visibility, and added some high-visibility narrative color to how and why I was trusted, and by whom.

This actually had one significant downside, as I started getting a bunch of low-quality leads from second-rate entrepreneurs hoping for introductions into elite Silicon Valley circles in the guise of a consulting engagement. In many cases, it was openly crude overtures that assumed I was in the influence-peddling business (I’ve never accepted money or gifts to make introductions, and have never made an introduction that I didn’t actually think had potential).

But the upside of the gig (besides the Breaking Smart workshop I spun out of it) was that it triggered a shift to Act 3, where I was not just a track record from nowhere. I could be located with respect to economic scene landmarks — I was a guy with a track record in the tech scene. I was part of the software-eating-the-world bigger story, if only as an extra.

This is important. Nobody is every trusted or trustworthy in isolation. You are trusted against a larger backdrop or scene. Your fortunes rise and fall with that scene. You can have a reputation that is hedged across multiple scenes, but you can’t be a “trusted guy from nowhere in particular.” I’ve seen changes in how new connections react to me based on how the reputation of Silicon Valley and tech have changed over the years. If the reputation of the tech scene ever takes a terminal nosedive, I’ll probably go down with it.

This is neither good or bad. It’s just the way it is. Stick around long enough, and you’ll be part of both the hero and villain sides of every story you’re in.

Act 3: Part of the Scenery

After 2016 or so, things got a bit… diffuse. I could tell from the way leads led to gigs that it wasn’t really about track record anymore. Somehow, mere visible survival, general approachability, and avoiding the allure of packaged, branded self-presentation seemed to have done the trick of making me look “established.”

It feels kinda like being a human bus stop in a city. People who traveled certain routes in certain scenes were simply aware of my existence because I was a visible part of the landscape in those scenes. This can feel a bit strange — you end up being at once seen and not-seen.

One result of this is that gigs these days feel less like the result of mechanical effects or numbers games, and more like little vignettes in a big story where I have a small role. Vignettes that could be footnotes in a sufficiently voluminous business/economic history. The logic has gone from statistical to narrative.

In Act 3, the three aspects of trust start to work differently in some sort of mature mode:

1. Discovery trust: This works via simple known presence. You’ve been around long enough, and the world is small enough, that enough people already know who you are. You’re part of the scenery that’s their mental model of a scene. You don’t need to be “discovered” by the local economy any more unless you want to venture into new domains or geographies because you’re bored (which I suppose might happen to me some day).

2. Commitment trust: This still hasn’t changed. It’s still about meeting face-to-face (on video is okay, but not ideal) and establishing rapport, and signing a contract you don’t have to think too hard about.

3. Working trust: This has again broadened somewhat beyond sparring work. I now am more willing to take on more complex kinds of work, including calibrated amounts of “trust debt,” but only with people I’ve established baseline working trust around something simpler like sparring or a quick workshop.

So that’s where I am now, in the middle of the third act of a 3-act story of evolving ability to trust and be trusted by real people, while remaining an actual person rather than a brand. How does this act end? How many more acts remain? I don’t know but I can speculate.

The Future of Trust

Looking ahead, I can see some interesting new challenges already emerging. Some are a result of personal things — in the next 10 years I’ll go from 46 to 56 years old. When I started, most of my clients were my age or older. Increasingly, most of my clients are younger than me. In rare cases a full two decades younger.

I can see clear signs of a looming trust problem I haven’t had to deal with so far — simply being out of touch with the world my clients live in (feels weird to think some of my future clients may be in kindergarten right now).

This isn’t an academic problem. Already, I’ve found myself saying no to potential clients who are clearly looking for some sort of paid elder mentoring rather than the kind of consulting I am comfortable providing.

I’ll cross that bridge when it becomes impossible to avoid crossing it.

A slightly different trend is also shaping my anticipation of trust trends. The Great Weirding has left the business world in a very altered shape. The Culture War has reshaped the landscape of trust. Tribalism is an actual factor now, in how consulting works. Increasingly, to access some space of gigs, you first have to gain membership into some sort of tribe that controls access to that space. I don’t like that, and avoid that kind of space, but it may become harder and harder to do so.

Trust works differently now in subtle ways I’m still trying to make sense of. Spooky trustworthiness at a distance is getting spookier. I have a feeling only half of what I think I know about trust will remain true in 2030. The challenge will be figuring out which half to keep, and which half to toss.

My ten-year anniversary as an indie consultant is coming up. On March 1, it will have been exactly 10 years since I quit my last job. It’s the longest I’ve ever been in any life situation as an adult. So I’ve decided to devote the next 4 issues of this newsletter to systematic reflection on the last 10 years, and to looking out at the next 10 years.

Let’s start on the base layer of the working life for everybody, whether in a job or an independent: workflows.

In this issue, I’m going to share a look back at how my workflow, more specifically my email inbox, has evolved over the last ten years since I quit my job. And look forward to how it might evolve in the next ten years.

This is a tale of 7 inbox conditions, marking a journey from my past workflows to my aspirational future workflows. Specifically, I want to take an inventory of the changing mental state induced by hitting Inbox Zero over the years (for the Gen Z among you, Inbox Zero is an idea most associated with David Allen’s famous GTD productivity system).

In theory, hitting Inbox Zero is supposed to make you feel mentally free, so it is an ideal best-case sampling point for your situation. How you feel when you hit Inbox Zero should reveal how free you really are.

Inbox Kinda-Free

This time, ten years ago, I had a job I had just decided to quit, leading R&D projects at Xerox.

In a job, once you’re above entry level, you’re typically on many email distribution lists. You are typically included in dozens of communication loops, whether or not you have any actionable responsibilities within them. You are expected to generally know what’s going on if you think you have — and want — a future in the company.

You have a manager and colleagues who expect specific things from you, but you’re also part of a larger corporate community that expects some general involvement from you, and gets generally involved with you in return. How you manage your involvement beyond immediate expectations is a function of your email game.

Back then, I used to be pretty disciplined about Inbox Zero.

In 2011, getting to Inbox Zero periodically with my work email, and enjoying a modest afternoon of clear-headedness every couple of weeks, was how I knew I was on top of things and at the right level of involvement with the corporate hive mind.

In the GTD philosophy, Inbox Zero is shorthand for the visceral experience of freedom. What I didn’t know then was that I hadn’t really experienced the intoxication of true Inbox Zero. Only a sort of low-alcohol-content ersatz version. As I now know, you cannot actually experience Inbox Zero at a job.

See, the thing is, at a job, your email is part of this river-like flow of the inner life of a business. Even if you happen to have nothing to do on a specific day, and are drifting between projects or bosses, you have an immersive situation awareness that you cannot turn off. Not even if you clear your inbox.

A nonzero fraction of your attention is locked up in the internal corporate stream of consciousness. Seeing, and being seen, in an open-ended way, within a shared situation awareness field, is how jobs work.

This is part of the definition of a full-time job — you commit to a mutual attention lock within the internal corporate stream of consciousness of an organization.

So even if you happen to achieve Inbox Zero at a job, in a decent-sized organization, your head never gets completely clear, because in a sense it’s not entirely your head to clear.

Inbox Zero amounts to Inbox Kinda-Free.

Your mind is not entirely your own to clear as you see fit. Other people have a certain right to peek into it and dump ambiguous things into it, generally via email (and these days via Slack and other media). A part of your head is devoted to, for want of a better term, “holding state” for the organization as a whole.

So you’re never quite free of and clear of the attention lock. Even if you hit Inbox Zero nominally, a part of your mind is always still “at work,” sharing in whatever sentiment superstate prevails in the organization at the time.

Inbox Void

On March 1, 2011, the day I left Xerox, that attention lock snapped free. And Inbox Kinda-Free turned into Inbox Void: the kind of emptiness it is terrifying to look into.

I no longer had my Xerox email account, and my Gmail was a desert.

Clearing it was trivial. But the clear state that resulted was not the Inbox Zero ideal of freedom. It wasn’t even kinda-free. Instead, it was a stark, oppressive emptiness that reminded me that I was not free. I was merely unemployed, and now newly burdened with figuring out how to make a living. My time wasn’t my own, but beholden to dollars I hadn’t yet figured out how to make, and clients I hadn’t yet landed.

Nobody needed me by default. It was no longer anybody’s job to check in on me and make sure I had enough to do. Or that I was getting paid enough to remain happy and productive.

The empty inbox was not a sign that I was on top of things, but a sign that I had nothing to get on top of, and that it was not actually a good state.

I didn’t need Inbox Zero. Inbox Zero was bad. I needed Inbox Busy. I needed a healthy flow of leads, inquiries, promising conversations for gigs, requests from clients, and so on. And I didn’t have it.

It took me perhaps another two years to get to there.

The interim was constantly stressful. The inbox would keep going to zero, with nothing to do, no leads to pursue, no obvious money-making options to simply exercise.

And there was no background stream of activity I could feel part of, to occupy my attention. At my job, even if I cleared my inbox on Sunday afternoon, I’d get up on Monday morning and face an inbox full of stuff to track, even if I was on top of my own stuff. It was like Twitter. The feed was always moving.

Early on, as an indie, I’d often clear my inbox, and it would stay clear of “work” email for days and sometimes weeks on end (not counting alerts, newsletters and personal email). Oppressively, stubbornly at zero even as the savings level slowly went down.

I’ll call this Inbox Void. A stressful kind of Inbox Zero that you don’t actually want. An empty state that oppresses rather than liberates, and can kill you if it persists long enough.

Inbox Anxious

It was probably sometime in late 2012, almost two years later, that for the very first time as an indie, getting to Inbox Zero became a non-trivial task again.

There was finally a there there to my consulting life. Enough going on in my email that getting to Inbox Zero meant doing some actual work. I had moved from Inbox Void to Inbox Anxious — activity tinged with ever-present financial uncertainty.

Multiple conversations were actually going places, email exchanges that could be called “work” were happening, contracts and NDAs were being sent back and forth. Hours were being billed, invoices were being sent out and paid (or not), context was being switched between clients.

I don’t remember the first time I had to handle two back-to-back meetings with different clients on the same day, and switch context on a dime, but at some point I noticed I was doing that sort of thing.

And suddenly it hit me: I’d gone from mostly faking it to kinda making it.

My indie consulting life felt real for the first time. It happened quickly, but not quickly enough that I noticed a sharp boundary. It wasn’t like a sudden switch being flipped.

But there was something new here. Unlike at a job, getting on top of consulting commitments and deliverables temporarily, and getting to Inbox Zero, felt different. Unlike at a job, there was no generalized background stream of corporate consciousness that would reassert itself and expand to occupy my mind via an attention lock.

This was a true zero. Once I got on top of things I owed clients, it was a kind of clear headspace with no background collective stream of consciousness at all. No attention lock within a hive mind.

But for the first few months, this state was fleeting and unstable. Impossible to sustain for more than a few minutes.

The thing is, even though there was no background stream of corporate consciousness to sink into, there was still the anxiety of insufficient gigflow, and too few leads turning into closed deals and signed contracts. Every time I hit send on the last thing I owed a client, and cleared the decks, the mild-to-medium anxiety (depending on cash runway) would flood right back in. And instead of enjoying “freedom,” I’d be thinking about how to drum up more work, or brainstorming other income streams.

This was what I call Inbox Anxious. Inbox Zero where the commitments have been cleared, but the anxiety has not, because you still haven’t acquired confidence in your ability to keep the gigs flowing. It’s better than Inbox Void, but hardly freedom.

You still haven’t learned to manage the stress of not knowing where your next billable hour will come from, or acquired the confidence that it will come, even if you don’t know from where. Part of you still itches to have a sure-fire plan for the next month’s rent. You haven’t yet shaken off the addiction to a predictable paycheck, to being needed-by-default by some large corporate consciousness.

Inbox Busy

Around late 2013 though, things began getting consistently busy enough, and I began trusting enough in things working out, that a new kind of Inbox Zero headspace became accessible.

I could turn around everything I owed clients, and I’d be in this intoxicating kind of clear headspace where I could feel really free. There was a real, reliable stream of ongoing activity to get away from — Inbox Busy — and I could actually meaningfully get away from it. Taking a busy inbox to zero meant actually being free rather than vaguely anxious.

Free of deliverables or paperwork I owed clients.

Free of background corporate streams of consciousness.

Free of immediate cash-flow anxieties.

It helped that my average savings level — or runway length — had slowly crept up over two years. The more runway you have, the more you can actually enjoy Inbox Zero when you get to it.

Initially, this kind of headspace was pretty rare. Maybe one afternoon every few months. Then I’d go through periods where I could hit that mood for an afternoon or so every week.

Those were fun times, but they didn’t last.

Between 2014 and 2017 or so, I suppose I went through some sort of consultant-market fit threshold, and almost without realizing it, landed in a condition where I typically had multiple active gigs going at any given time (right now I have 5 active gigs and 3 on the back burner), and getting to Inbox Zero started getting rarer and harder than it had been in my old job.

I had gone past being busy enough to being too busy (which is not the same thing as making too much money). I’d landed in the regime I’m in now: Inbox Chaos.

Inbox Chaos

In a single company, the corporate stream of consciousness has a sort of harmonized flow to it, so you can generally stabilize and zero-out all your active threads at once. And when you do, there is something it is like to simply be immersed in the corporate stream of consciousness. It has a direction and purpose, and an ongoing story that makes sense. For me, at Xerox, on afternoons I got to Inbox Zero, I’d land in a sort of generic Xerox headspace. I’d check in on other projects, chat with colleagues, catch up on intranet news, and generally partake of the Borg’s mind-state (or more technically, the egregore mind-state).

When dealing with multiple clients operating on very different tempos within unrelated stories, with corporate streams of consciousness in different moods, it is much harder to wrangle them all down to zero at the same time.

And when you do manage it, while you don’t have a single corporate stream of consciousness filling your head, you have this sense of being in the eye of a chaotic storm.

The thing is, the economy is a wild place, and once you’re plugged in enough to the wilderness directly via multiple varied connections, there is a sense in which you’re now immersed in the stream of consciousness of the economy as a whole.

The larger gestalt of macro forces and trends starts to seep into your consciousness. It’s not just the news. You’re not a spectator or an analyst writing trend reports from the comfort of a Gartner office. You embody the health of an economy, in the sense an indicator species embodies the health of an ecosystem.

But unlike a corporate (or even sectoral) stream of consciousness, there is nothing it is like to be in the general macroeconomic stream of consciousness. The economy, unlike a single corporation, is not an egregore or Borg-mind. There is no mind directing the invisible hand.

While more diffuse and incoherent, and more resistant to anthropocentric identification, this stream of macroeconomic consciousness is ultimately far more powerful than that inside any single company. Once you get sensitive to it, and open your mind to it, it will start to colonize your mind, unless you do something to stop it.

Sometime around 2017 I noticed that this was exactly what I was doing. I had almost unconsciously started cashing out some of the freedom of Inbox Zero moments (turned into hours and days), with the chaos held temporarily at bay, by indulging in several “freedom projects” of my own.

And that had workflow implications.

For example, I realized that I liked to save mornings for writing, and that I did not enjoy having to work on two different gigs on the same day. Back-to-back meetings with multiple clients, previously a sign of having made it, and a sort of badge of honor, now began to seem annoying and exhausting.

Almost without planning it, I started doing active load balancing, batch processing, and time management to create and maintain conditions favoring more frequent and extended Inbox Zero headspace. Hilariously enough, this was the reason I quit my job in the first place — to be able to do that. It just took me ten years after quitting to actually get there.

I was starting to identify and wall off small, fragile islands of actual freedom that I could inhabit during the more stable periods of Inbox Zero, protected from the chaos.

I began saying no more often to potential clients whose needs didn’t fit the workflow rhythms I wanted to create, preserve and protect. I began setting expectations with clients that created room for my own activities. I no longer promised aggressive turnarounds that would disrupt my own routines. Protecting islands of true freedom on my calendar began to seem more important than maximizing billable hours.

It wasn’t that I was making more money, but that I had begun to value time better. That, I think, is the beginning of getting to Inbox Free. When Inbox Zero actually feels like freedom, rather than some lesser thing.

Inbox Free to Inbox Zen

I hope where I am now is on the cusp between Inbox Chaos and Inbox Free. A state where I can periodically get to Inbox Zero, and stay predictably in a free-and-clear headspace long enough, and frequently enough, to make steady progress on my own “freedom projects.” I don’t care about maximizing revenue, and I don’t worry about “leaving money on the table.” So long as I’m making enough to pay for my life, and some savings, I’m mainly solving for freedom. It’s just taken me a decade to get to where that’s a meaningful problem with real solutions at the workflow level.

I still can’t reliably do something like block out entire weeks to make progress on some freedom project, like my much delayed science fiction novel, or the rover I am trying to build. But I can do an afternoon. And occasionally a whole day.

Progress!

Admittedly, Inbox Free seems like a distant goal now, but it no longer seems like an impossible utopia. The chaos overwhelms me more often than I am able to hold it at bay. But I’m getting slowly and steadily better at holding my own. I wouldn’t say I’m winning the battle against chaos. But I’m losing less often.

This does not happen automatically.

It takes work to create these chaos-beating conditions and maintain them. It takes cunning to turn Inbox Zero moments into Inbox Free afternoons or days. And they can be destabilized at any time by a bad quarter or year. By a gig falling through or a contract getting canceled.

Experience and a ten-year track record do not make you immune to the vagaries of the gig economy. Just because I’m a decade into the game does not mean I can’t hit a bad patch, and regress back to Inbox Anxious or Inbox Void.

But having been there before, and having climbed out more than once, I have a certain confidence in my ability to do so again. And again.

It’s not Sisyphean though. It’s more like a video game, where once you reach a certain level a couple of times, even if you get killed and have to respawn at Level 1, you know you can get back to the previous highest level again. You might even be able to speed-run there. And each time you return to your previous highest level, you have another shot at making it to a new level.

I don’t know what the next ten years hold for me. I am 46 now, and will be 56 then if I am still around. Maybe there are a few more Inbox Levels to discover with increasing levels of freedom. And maybe there’s even an end to the finite game of inboxes, when I can quit playing the high-stakes version, where I have to keep score and actively work the time-vs-money tradeoff curve.

Maybe I’ll hit the Zen mode of the game, where I’m playing to continue the game, rather than to win the current level.

One can hope.

One of the things free agents have to do is actively manage their psyches around work. In the paycheck economy, if you have a decent job, amateur psychology is mostly just an idle pastime built around comparing Myers-Briggs profiles for fun, and trash-talking people who score differently than you. If you’re otherwise mentally healthy and the job is not toxic, it is just harmless fun. The environment itself passively manages your psyche by being relatively stable.

But for free agents, managing your psyche can be a matter of life and death. Unhealthy attitudes can send you down a spiral of self-destruction no matter how strong your position. And healthy ones can transform even bad situations into strong positions.

To help you reflect on how you manage your psyche, I made a table of what I think are the important dimensions free agents should periodically reflect on. I’ll explain the logic in a minute, but before you read on, just go down the rows of the table and identify whether your attitudes most align with the Parent, Adult, or Child column on each dimension. You don’t need to understand the underlying conceptual machinery to do this.

The table is based on conceptual machinery from one of my favorite DIY psychology frameworks: Transactional Analysis, or TA.

TA is a neo-Freudian approach to psychology, developed by Eric Berne, which was very popular in the Eighties. It was applied primarily to analysis of game-like behaviors in relationships (explained in Berne’s bestseller Games People Play), based on unbundling personality into Parent, Adult, and Child components (updates to Freud’s superego, ego, and id). The models were later extended to analysis of life scripts and postures (in Thomas Harris’ bestseller I’m Ok, You’re Ok).

While these basic uses of TA for game and script analysis are very useful for for the free-agent’s toolkit (client interactions are full of Bernean games), I want to suggest a different use: periodically recalibrating your relationship to the world.

Though I’ve drawn on TA models and frames to make the table above, you don’t need to be familiar with the conceptual machinery to use this table and draw conclusions from your responses.

Along the key dimensions in the table, how do you relate to the world?

• Through your Parent, via internalized, unexamined societal attitudes and received wisdom?

• Through your Adult, via conscious, reasonable, competent, reality-grounded behaviors?

• Or through your Child, via playful, exploratory, fumbling, muddling, impulsive engagement of the world?

Paycheck employees in non-executive ranks typically have a strongly Parent-dominant life posture. Executives and more mercenary 80s/90s/00s style free agents typically have a strongly Adult-dominant life posture.

Neither is, I think, well adapted to the world we are heading into; the world that has been taking shape since 2015.

Strange though it might seem, a Child-dominant life posture is actually best suited for our current world, and is characteristic of both innovative entrepreneurs and free agents who thrive.

Why?

The Biggest Risk

The thing is, the biggest risk in the weird new world is neither long-term security (which Parent-dominant attitudes solve for) or short-term survivability (which Adult-dominant attitudes solve for). Those are important, of course, but moot if you become too disenchanted with the world to even get up in the morning and do something meaningful with your day.

The greatest endemic risk to the psyche in 2021 is not that you’ll end up on the streets next week or fail to fund your retirement in 30 years. The greatest risk is that you’ll feel so relentlessly battered by the weirdness all around that you’ll go numb and simply disengage from the world entirely today.

Short and long-term security are moot if your life minute-to-minute is unlivable due to overwhelming weirdness. And your inner Parent and Adult have no clue how to handle the trauma of weirdness.

The evidence for this is all around us. Around the world, younger generations are reacting to coming of age (which is the same thing as reining in your Child and turning on your Adult and Parent) in a bleak world by retreating.

The Japanese phenomenon of hikkikomori is spreading. The risk of becoming so disenchanted with the world that you retreat into your parents’ basement is high. Ironic, huh? Giveupitis as the mark of growing up.

Some call this a meaning crisis. I’ve lately started thinking of it as an enchantment crisis. The primary reward your Child seeks in the world is an enchanted way of being in it. When this drive is starved, you get disenchanted, and even if your Adult remains competent at functioning in the world, and your Parent has all the right cliches on file for every situation, you lose the will to live. Because that will comes from the id, the Child.

This is becoming increasingly common. It is getting easier and easier to become terminally, fatally, disenchanted with the world and turn into one of the walking dead, a zombie assemblage of functional but pointless Adult/Parent drives, until one day you fall down and can’t get up again because you don’t want to.

See, the thing about the weirdness all around is:

• Most Parent data (the superego is mostly data) has been undermined by recent historical developments. Your Parent is kinda out-of-touch (just as your actual parents likely are). Your hand-me-down cache of cliches to live by has been invalidated.

• Most Adult skills (the ego in TA terms is mainly skills grounded in reason) have become overwhelmed by the sheer complexity and weirdness of our world. The formulas and algorithms don’t work. They’re thrashing. They’ve turned into delusions of competence. Adulting has turned into a non-functional LARP. That’s why you have to learn it like it’s a quaint retro hobby from 1955. If “Adulting” were actually life-critical, you’d be dead already.

• But most Child tendencies (the id is mostly tendencies) are still pretty functional. Children are naturally present in the world as strangers in a strange land; alien beings suddenly dumped into relentless weirdness. Healthy children respond to weirdness with exploration and learning behaviors. They respond to felt incompetence with trial-and-error practice. Healthy children prioritize enchantment, not retirement funds. The worry about making this minute worth experiencing, not making rent.

Though it might seem insanely risky to let your Child lead, with your Adult and Parent biting their tongues and following, under the extreme weirding conditions of today, it’s actually the safest thing to do.

Dump the shaky preconceived notions of the Parent. Dump the flailing and delusions of competence of the Adult. Let the Child lead.

Pay Yourself First: Child Edition

One way to operationalize this observation of the world is to reframe the classic personal finance advice, pay yourself first.

In the traditional form, the advice means paying into retirement savings before budgeting discretionary expenses.

This is classic Parent-dominant advice: long-term oriented, prioritizing social stability (of institutions that underwrite old age for all), etc. It is about saving money for future-you, while trusting that society will endure, and doing your part to make sure it does.

Between 1980-2015, this advice turned into a more Adult-dominant idea with emphasis on short-term risk management, winning in a Hobbesian neoliberal environment, and making sure your retirement was funded even if the world threatened to fall apart by the time you turned 65. It was a kind of Neoliberal Athletics competition.

But how are you supposed to pay yourself first when you are a NINJA? No income, no job or assets? Forget the defined-benefit pensions or lifetime employment of the 70s. You can’t even bet on the defined-contribution (employer-matching) or short-term stable jobs of 1980-2015.

To center the primary risk — of terminally disenchanted retreat from the world — I think of pay yourself first as being about the present-moment you, and in terms of time rather than money.

Pay yourself first in 2021 means prioritizing time for some activity that keeps you positively engaged in the world, through some enchanted mode of seeing, being, and doing that resists disenchantment and retreat to basement fantasies and LARPs. You only retreat to live in a video game world when you can’t find a way to participating in the enchantment available in the real world, no matter how weird such participation looks to traditionalists.

Pay yourself first in 2021 means aggressively nurturing and defending your primary mode of enchanted engagement with the world, even if it means forgoing some money in order to buy yourself the time to do so (something I’ve done very frequently).

Everyday Alchemy

I call this transactional enchantment both as a hat-tip to the Transactional Analysis frame that inspired it, and to point to the idea of trying to bring an enchanted perspective to everything you do, whether it is drafting an invoice, looking for gigs on Twitter, or writing a newsletter.

Enchantment is not just for game nights with friends, or whatever traditional or New Age spirituality you favor. Or something to relegate to hobbies, fiction-reading and TV-watching. It is something to infuse into everything you do.

It’s not about magic or woo. It’s about transacting with the world in a way that makes life not merely possible to live (whether in the long or short term) but worth living minute-to-minute.

What’s the point of short and long-term security if every day you wake up wishing you could just stay in bed, numbly withdrawn from the world, swaddled in blankets?

What’s the point of contributing to retirement savings if, like Bartleby the Scrivener in Melville’s short story, your attitude towards work has degenerated to “I would prefer not to,” and you’re one step away from terminal catatonia?

My own mode of transactional enchantment has been writing. Through good and bad times, cash-flow crises and flush periods, painful gigs and fun gigs, I’ve never stopped writing. I was writing through the euphoria of 1997-99, and I was writing through the Global Financial Crisis. I was writing through the halcyon GFC-recovery years of the early 2010s, and I was writing through the PTSD of the Great Weirding.

Everything I do is informed by my writing, and everything I do feeds into it. It’s where I transform the banalities of my day-to-day activities into an experience of life worth living. It’s my way of staying on top of the everyday alchemy that you simply cannot afford to get behind on. The disenchanted life is not worth living.

Writing is not the only way to achieve this kind of transactional enchantment, but it is one of the most accessible ways. It demands the least in terms of special talents. You don’t need to be artistic, musical, or good at programming to do it.

Just pick your mode (or rather, let it pick you). It’s the enchantment mode of being in the world that matters, not the medium.

If you fail at this absolutely basic housekeeping task of generating transactional enchantment in your life, minute-to-minute — literally Child’s play — everything else is moot. Your retirement fund won’t save your sanity, and LARPing Aurelian stoicism (a popular genre of Adulting) won’t make life worth living.

So pay yourself first. Make the time to stay transactionally enchanted with the world. Otherwise it’s game over.

It’s been twenty years since Dan Pink published his landmark book, Free Agent Nation, or FAN, in 2001. It remains, in my opinion, the most prescient among the many such books that were being published around that time. The other big one was Future of Work, which inspired the development of eLance. Elance, after merging with oDesk, turned what is today Upwork, the default entry-level gig marketplace.

I read Dan’s book in 2007, and it inspired a gig marketplace product I developed at Xerox (during the course of which I had a lot of interactions with the people then running oDesk). I also got to know Dan a bit (he blurbed my book, Tempo).

In the twenty years since FAN was published, the free-agent nation has turned into the free-agent world. It is more than just an economic sideshow now. It is a young, but full-stack model of civilization. A way to run a world. It boasts a relatively full set of folkways spanning culture, politics, economics, and lifestyles. Since Covid, it is beginning to increasingly look like the default along many dimensions, such as working from home (WFH).

Many other big and interesting ideas have emerged in the 20 years since FAN, the most well-known being Tim Ferriss’ Four-Hour Work Week. Among my own favorite ideas are Marci Alboher’s idea of “Slash” careers in One Person/Multiple Careers (here’s my review from 2009), named after the way people tend in the gig economy tend to describe themselves with slash-separated descriptors, like blogger/consultant, and Hugh MacLeod’s Sex and Cash theory.

All this stuff is like water now, so it’s hard to see, but all the ideas we take for granted today were not obvious ten or twenty years ago, let alone engineered into an entire stack of tools and a growing cottage industry of startups that expressly set out to serve our needs in the what Li Jin dubbed the Passion Economy.

Among the ideas that were new and strange ideas to most of us sometime in the last twenty years:

• Looking for gigs on online marketplaces

• Coworking spaces

• Networking on LinkedIn

• Parleying online activity into a speaking career

• Teaching and coaching online

• Managing a personal brand

• Professional website hosted on your own domain

• Showcasing your technical abilities on Github

• Working “under the API” with an algorithmic boss

• Uber for everything

• Turking and crowdsourcing

• Raising money for speculative work via GoFundMe, Kickstarter

• Getting paid via PayPal

• Videoconferencing and VoIP

• Cloud-based subscription software for every business function

• Self-publishing your own paper and e-books via self-serve tools

• All of social media

The list goes on and on. Those of us who grew old alongside this technology learned to work with each new capability as it became available. Seeing it listed all-at-once gives me a bit of nausea frankly. Did I really live through the arrival of all those things on the scene? Am I really that old? Did I really leave the paycheck world I was factory-manufactured to inhabit, and learn a whole new set of work-ways, ways new to humanity, over the course of the last 10 years?

Those of you who are entering the workforce now (whether via a YouTube channel or TikTok at 14, or straight out of college and failing to find a job at 21) are faced with a nearly complete stack of economic life-support technologies, but a mainstream economy that still acts like it is some strange weird new thing that nobody knows how to use, even though to you it is likely already second nature, and most things in it are already over a decade old.

Over twenty years, literally tens of thousands of blog posts and magazine articles were written, exploring the future of work that we now inhabit.

Dozens of them went on to become classics. Remember Kevin Kelly’s 1000 True Fans? That was 2008 and was not obvious before. How about Chris Anderson’s The Long Tail? That was 2004 and again not obvious before. Many individual books and blog posts were faddish, but their cumulative effect was to map out an entire emerging new world. Hundreds of blog posts and books contributed little bits and pieces of ideas, but were then forgotten.

Though this newsletter is under 2 years old, I’ve been part of this conversation for as long as I’ve been writing online. Some of you who were following my writing 13 years ago may remember that in 2008, I won a prize from the audio equipment maker Plantronics for coming up with the term “Cloudworker” to describe the newly emerging class of workers.

All that seems a lifetime ago.

But the conversation started, I think, with Dan Pink and FAN. When you compare FAN and books that came after with books like Michael Gerber’s 1986 classic, The E-Myth (revised and updated in 2004 as The E-Myth Revisited, but unable to shake the pre-2000s vibe — the E- stands for entrepreneurial, not electronic), you can sense that something important changed around 2000, which Dan was among the first to spot.

While E-Myth is a good book for the gig economy, with a lot of good advice for people wanting to start solo small-business lifestyles, it is fundamentally rooted in a pre-Internet world. Just like “executive suites” existed before “coworking spaces” but fundamentally represent a different mindset (and a unit-economics structure that is closer to motels).

Dan realized that the internet changed the game radically, and spotted many of the early signs. Including the important fact that the Bureau of Labor Statistics was not meaningfully tracking free-agents (and still doesn’t), confusing them for either contractors or 1-10 person small businesses. What was remarkable is that he spotted many of the signs before they turned into clear and obvious markers.

Remember, this was when even videoconferencing was a special, expensive thing, VoIP was some sort of new-fangled magic, people actually paid big money for international calls, and getting paid electronically via PayPal was only just starting to become a common thing.

It’s kinda funny that “strategic foresight” people within paycheck organizations still continue to write ponderous “future of work” trend analyses that seem to think stuff we’re doing today is stuff to expect in 2030. The future that Dan Pink foresaw in 2001 is already here, and is not even unevenly distributed. It’s all over the place, and easier to get into than the paycheck economy, which increasingly looks like an exotic science fictional universe that’s harder and harder for ordinary people to break into.

I think we are at another moment like 2001. A phase shift in environmental conditions is being triggered by the exit of Donald Trump and the inauguration of the Biden administration. This time, the changes being triggered today (and early signs and portents are visible) will be mostly around politics, taxes, and other such non-technological things.

It’s time to pay attention again because the game is about to get reinvented again. The Free Agent World is past its technological origin story, and is about to start growing up.

Money is an unseemly topic to discuss in the paycheck world. There is a fairly strong global social taboo around openly discussing salaries.

Less obviously, it is an unseemly topic in the indie consulting world as well. We just don’t notice as much because, conveniently enough, it also happens to be harder in practice to do the math to get to taboo-worthy paycheck-equivalent numbers to compare. But that doesn’t mean we are any more willing to discuss income openly.

But more interesting than the mere existence of comparable taboos in the two worlds is the fact that they exist for different reasons.

In the paycheck world, the taboo exists so it is easier to fake your position in the keeping-up-with-the-Joneses rat race. But that doesn’t explain the taboo in the indie world, since we very theatrically quit the rat race as our opening gambit, often with some holier-than-thou posturing and manifesto-writing accompanying our exits (which is fine; a bit of positive self-talk to work up the courage to quit is perfectly acceptable).

So what’s the deal with our version of the taboo? And should you break it?

The Salary Discussion Taboo

In the above-the-API paycheck world, it is obviously beneficial to employers if employees don’t discuss salaries openly, and though in the US you cannot be legally prohibited from doing so, many employers strongly encourage the norm. Many even institute it as a policy, though it cannot be legally enforced.

The thing though, is that employees don’t really want to discuss their salaries openly any more than employers want them to, whatever the cost in terms of ceded salary negotiation leverage.

Periodically there are calls by well-intentioned people to “normalize” open discussion of salaries, but it never works and never will.

Why?

In the modern world, income, identity, and social status in the middle class are too tightly coupled for talking openly about salaries to be comfortable. Revealing how much you make has social consequences. Gaining salary negotiation leverage against employers is a secondary consideration. Maintaining a social status quo relative to neighbors and work peers is primary. Your neighbor (or coworker in the next cubicle or Zoom window) with a very similar home and car may be making twice what you make, and have half as much debt, but you wouldn’t know it — and it is in both your social interests to pretend the differences are smaller than they might actually be.

The salary taboo is a peculiarly middle-class thing, and there’s a history to it.

Through most of the twentieth century, as the middle class grew and absorbed chunks of the working and wealthy classes, the taboo grew in strength. Socially, the middle class is much more egalitarian than either the wealthy or the working classes. Markers of differences in wealth and income are subtle and understated. The differences are not denied, but their social consequences are consciously minimized. Shared social realities — such as schools and community centers — present a facade of near-absolute equality. Even in the US, where homogenizing norms like school uniforms are uncommon, flaunting your parents’ wealth too openly, or failing to adequately mask their lack of it, marks you for social consequences.

After 1980, as the middle class began to both shrink and socially fragment under economic stress, the taboo weakened, but only slightly. Social life in the middle class depends too much on the pretense of relatively equal, or at least non-traumatically-comparable lifestyles, for the taboo to dissipate. A twinge of envy when you look over to your neighbor’s driveway is not just acceptable, but desirable. But you don’t want such casual awareness of your social milieu to turn into suicidal despair at the unfairness of the universe.

All this tempers the impulse to share salary information, and the impulse is not class-native to begin with. So where did it come from in the first place?

The thing is, the very idea of trading salary information for shared negotiation leverage is fundamentally a working-class solidarity tactic.

In the working class (what used to be called blue collar or service labor, and I call under-the-API work in its modern form) openness about pay harmonizes well with things like unions and fungible labor.

In the traditional working class, people were much more interchangeable. They were valued by role, and by a relatively straightforward correlation between experience (“seniority”) and a worth-in-role perception that was relatively independent of skill (unlike modern white-collar work or pre-modern craft work).

It’s not that the working classes are less socially competitive — it’s that they are too interchangeable at work for work identities to form much of a basis for individually differentiated social competition.

As a result, working-class Joneses around the world compete socially in other ways. In the US, historically, things like Christmas decorations, bowling scores, baking skills, chili recipes, drinking stamina, and dancing abilities have mattered more than income. Neighborhood “Big Man” types dominate local social hierarchies much more than in the middle class.

Among the wealthy, of course, the discussion is moot. Net worth and political power are far more important than salaries (and indeed, among the truly wealthy, living off investment income is the norm, and working for money at all marks you as not-quite-top-shelf).

Now consider the corresponding picture in the indie economy.

Indie Income Illegibility

To be clear, I’m talking above-the-API new-white-collar indies, not Uber drivers. Below the API, if you do particularly well or poorly, there are incentives to brag or complain, since it reflects on algorithmic casino dynamics more than your personal character. Above the API, things are more complex.

To begin with, talking about money at all is basically harder for indies, for several practical reasons:

1. More dimensions: It takes more numbers to capture even a basic picture of an indie consultant’s personal finances. At the very least, you need their effective hourly rate, number of hours actually being billed at that rate, and routine operating costs, all of which are uncertain and radically variable. Most indies don’t even have a good handle on their numbers. Sharing them openly is moot.

2. More complex costs: Unlike paycheck employees, indies may have wildly varying non-routine costs due to things like subcontracting, paying for their own tools, and self-funded spec work which may involve upfront costs like travel and capital equipment, or just drawing down savings and turning down paid work (an opportunity cost) to invest in spec-work with higher potential.

3. Lower lifestyle correlation: You cannot easily guess income from visible markers like type of work (descriptors like “strategy,” “coaching,” and “design” reveal almost nothing), type of car a person drives, or what neighborhood they live in.

4. Lifestyle design: Indies have the freedom to do a lot more strategic lifestyle design, and many make heavy use of that freedom, which makes apples-to-apples comparisons with the Joneses harder. In a sense, it’s closer to comparisons across countries than across fences. Every indie is like a country unto themselves, even if they don’t move to Thailand.

5. Wealth-income blurring: Despite typically middle-class financial profiles, the financial and risk-management style in the indie world resembles that of the wealthy class, with a weird mix of work-for-hire income and cash flows that look like investment income. Once you are somewhat established, there are usually capital-like assets in the mix (such as book royalties, affiliate income, or pre-recorded courses) that have no clear social significance.

6. Tax-optimizing behaviors: Even when indies pay themselves a regular paycheck (such as you’re required to do with an S-corp in the US for instance), the numbers are designed to minimize taxes rather than maximize a vanity number. Other tax-driven behaviors include choices of where to live, renting an office vs. maintaining a home office, how you handle insurance, and so on.

Given all this complexity, indie income is highly illegible.

Personally, I really only get one meaningful snapshot of my income per year, when I do my taxes. And even that is shaky since I sometimes defer revenue or expenses, and at other times, take money in one year for work that will be actually be done in the next year. Once every few years, I sit down and do some analysis, but it’s a pain to actually keep track in any detail.

So the headline — but not the bottomline — is that indie income is fundamentally more illegible.

Now, it wouldn’t actually be that hard to set up systems to do the math and come up with a fairly accurate “paycheck equivalent” number. If you do your books properly, you’d just need to spend more time (or pay your book-keeper more) to generate an additional report in QuickBooks. But doing the math wouldn’t be hard. In the simplest case, it would look something like this.

• Trailing 12-month revenue: $100,000 (accrual basis)

• Trailing 12-month costs (including subcontracts etc): $20,000

• Moving average monthly salary-equivalent: $6667

In more complex cases, you’d have to put some thought into building a good equivalency calculation model (did you account for typical employer-matching contributions to retirement accounts and health insurance? How about any creative (but hopefully legal) expensing you might be doing, to move some costs from your personal to business budget?

But here’s a more basic question.

Why do you want to know this number, let alone share it openly?

What would you do with it if you set up some scripts to compute it every month? How does knowing the number help when you’re facing a cash crunch right now due to late invoices or a dry spell? How does it help you set an hourly rate?

And there are good reasons to not want to know.

Because you see, like our friends in the paycheck world, we don’t want to talk about it either. But for different reasons.

The Indie Income Taboo

The indie consultant class is, socially, part of the middle class. We tend to live roughly middle-class lifestyles in middle-class neighborhoods. Our friends in the paycheck world tend to be middle-class too.

So one obvious reason we share a paycheck-discussion taboo is that we still belong to the class that has such a taboo, even though our economic lives have changed. Sheer force of habit, and ongoing social reinforcement are powerful.

But that’s only a small part of the reason.

The real reason we don’t want to know or discuss our numbers is different: it makes it harder to lie to ourselves.

The way we indies describe ourselves to ourselves, and to a lesser extent to the world via our websites and social media profiles, is some mix of marketing, wishful thinking, and aspirational thinking. Looking too closely at numbers — even when we can’t easily compare them to others — tends to puncture our self-images in depressing and demotivating ways.

• Are you really a “strategy consultant” or did 58% of your income come from intern-grade Excel-monkeying, and 37% from affiliate income, leaving just 5% of your income matching your claimed headline?

• You might claim a half-dozen clients, but maybe 90% of your income came from one anchor client you dislike, for whom you do work that looks nothing like your headline, and you are more than a little embarrassed by.

• Perhaps you claim to do “strategic brand narrative” work, but are really spending 90% of your time crafting clickbait email campaign headlines for a sketchy business.

• Perhaps you claim to do organizational development for Fortune 100 companies, but that was one gig 3 years ago, and now you really mostly run a scammy online workshop for B-players at third-rate companies paying their own way.

• Maybe you’re making a ton of money, but looking at the details of how the sausage is made reveals the utter meaninglessness of what you do, highlighting how it is actually worse on that front than the job you left for not being “fulfilling” enough.

There is a social aspect too. We indies may not compare lawnmowers across picket fences. We may not compare suits and ties on the trading floor of an investment bank. But we do compare, for want of a better phrase, online narratives and postures. We have our own version of keeping up with the Indie Joneses (heh!), where our Twitter bios play the role of the car in the driveway.

We know what sounds fake, and what sounds real, and have finely calibrated bullshit-detectors when it comes to parsing the public profiles of peers.

• We can guess who’s putting on a desperate brave face, and who is understating what they’re making.

• We can guess who is on the brink of penury, and who is on the brink of being able to quit paid work altogether.

• We can see who is a grifter, who is a posturing snowflake, and who is really just a paycheck employee without health benefits.

• We can generally pick out the people who are actually trying to do interesting and meaningful work. We can guess the extent to which they are succeeding.

Our version of the game would obviously be much easier if everybody shared more. But should we?

Is it perhaps a good thing that the game is as hard as it is? Do we actually want to be putting our current moving-average incomes on our Twitter bios?

Should you break the taboo and find ways to talk openly about how much you make? Or should you respect it, and learn the nuances of the game of keeping up with the Indie Joneses?

The Taboo is a Good Thing

This might be a surprising conclusion, but I think for indie consultants, as well as for paycheck types, the taboo is actually a good thing.

A richer, more functional social milieu exists because we have a certain sense of decorum around how we talk money. This sense of decorum is, in my opinion, wiser than the impulse towards what is generally a vanity form of openness.

In the case of indies, the important thing is to not lie to yourself, but the salary-equivalent number does not actually matter for its own sake. Unlike for paycheck types, it plays no meaningful role in your life. Since you don’t use it as the basis for negotiating anything, it doesn’t matter. On the other hand, component numbers of the illegible formula, like an hourly rate, are meaningless to compare on their own.

So for your own needs, the important thing is to develop ways of looking at your books that keep you honest about the questions that actually matter:

1. Does the headline of the work you claim to do match the contents? It is okay for there to be a gap so long as you understand clearly why it exists and should exist.

2. Does your income mix reflect your actual or desired posture? Both are fine — so long as you know which it is.

3. Are you doing too much of work you don’t want to, and too little of work you do want to? Are you able to say yes/no to gigs wisely, assuming you can say no at all?

4. Are you able to invest as much as you want in spec work and non-consulting income assets?

5. Are your finances lifestyle-optimized and tax-optimized?

6. Are you saving at a reasonable rate — like paycheck types, you too will grow old, less able to work, and needing to retire.

7. Should you accept this gig at this hourly or project rate? Will you learn something new that’s worth any discount you might be offering to land the gig?

8. Is your runway healthy? How about your health insurance situation?

9. Do your risks look good? Are you betting on things with a range of upsides?

10. Are there things you want to buy that you are not able to afford? Material quality of life matters.

The thing is, the paycheck-equivalent number doesn’t actually matter for any of these questions; it is a pure vanity metric of no consequence.

The only reason to want to know it is to have something to compare with others, and with your former paycheck self (and former colleagues still in that world).

So there is no personal reason to answer that particular question of paycheck-equivalent income.

What about social reasons?

We don’t play the keeping-up-with-the-Joneses game for neighborhood status, but we do play something that looks a lot like it, and it is not meaningless.

Learning to present yourself, and parse how others present themselves, is an important skill. You have to look enough like other people that potential clients understood who you are and what you offer (ie don’t call it “customer delight wrangler,” just call it “marketing”), and unique enough that they want to hire you specifically.

Part of learning this skill — and teaching it to newer indies who might find your experiences useful — is being able to talk compassionately and usefully about these things while being kind to each other, in terms of not overtly challenging the personas we all try to present and inhabit, where it would do more harm than good.

To the extent taboos foster healthy patterns of mutual support, they are good. To the extent talking about numbers out of vanity, some misguided sense of openness, or an inapplicable sense of solidarity, actually hurts others (by drawing them into unwise candor or demotivating them) violating the taboo is actively bad.

Reveal what you’re comfortable revealing, when and where you’re comfortable revealing it. You’re an adult. You don’t need rules/boundaries of the sort designed for children where thoughtfulness is called for. But you don’t need idealistic taboo-breaking for its own sake either.

It is entirely fine to tiptoe around sensitive matters with euphemisms and obfuscations. For example, I rarely ever share my income details even 1:1 with highly trusted friends (on the one day of the year that I actually have a sense of it), but I’m happy to share hourly rates pretty freely (but usually only 1:1) and advise others on where to set theirs, or how to price project-style bids.

I’m typically open about approximate narrative indicators like “I am making more than I did at my last job, but not as much as I probably would be by now if I’d stayed in it and progressed at the expected rate.” That sort of thing, I think, helps others calibrate in useful ways, and make their own quit/stay decisions.

It is somewhere between childish and clueless to hold to arbitrary standards of openness as a value for no good reason.

This is particularly a lesson struggling, early-stage indies need to internalize, because they often don’t recognize the costs of openness. Some seem to believe they have so little, they have nothing left to lose.

It is certainly okay to ask for help, even publicly on Twitter. It is okay to share some of what you’re going through. But there are costs. You don’t exist in a bubble of security and unconditional positive regard as you might within a healthy family. You exist in the real world, where what you say affects how you are perceived, and determines who is willing — or not — to deal with you. You exist in a world where visible vulnerability can be exploited.

There are real costs to posting a highly detailed confessional laying out all your deepest financial life secrets in the misguided belief that such openness will be seen as “authentic” and lead people to magically open doors for you.

That doesn’t happen. The world doesn’t work that way.

In the adult world, there is always a balance to be struck between vulnerability and guardedness, openness and discretion, managing perceptions versus presenting an unedited self to the world, solidarity with others, and pragmatic self-interest.

Wanting to be completely open financially — whether the picture is one of abject despair or obscene success — is more often an exhibitionist impulse or a reaching-out for human connection than it is a useful tactic in improving your financial condition.

So yes, talking about money is fraught — and it should be. Don’t let misguided idealism draw you into talking about money in ways that don’t feel either right or wise.

Well it’s only January 7, 2021, and the Big Bad Wolf is already huffing and puffing more powerfully than in 2020, threatening to blow our houses down. There’s an insurrection being held at bay in the United States, a more virulent mutated SARS-CoV-2 abroad, and the vaccination effort is running into a wall of distribution snafus and vaccine hesitancy.

What’s a precarious free-agent to do in this environment? Turns out the folk tale of the Three Little Pigs and the Big Bad Wolf sheds some interesting light on the problem. It is a good allegory for resilience in turbulent times — the Big Bad Wolf huffing and puffing like it’s 2021.

Which of the three little pigs should you try to be: the one in the straw house, the one in the stick house, or the one in the brick house?

• The pig in the straw house is the typical free agent, with the flimsiest of protections

• The pig in the stick house is the typical paycheck employee, with a little more apparent resilience

• The pig in the brick house is the one with a strong liquid cash position and deep savings, whether as a free agent or an employee

Here’s a perhaps counter-intuitive idea: if you can’t live in a brick house, the straw house might actually be a better bet than the stick house.

As I noted in my first Covid-response post on March 12, 2020, Gigging in the Time of Corona, cash, control, and community is the best formula for resilience. If you’re strong on all three fronts, you have a brick house. If you’ve got that, you’re in good shape.

But if you compare paycheck employees with poor reserves to free agents with poor reserves, who comes out on top?

Superficially, it might seem like the stick house is better. It buys you a little extra time against the huffing and puffing of the Big Bad Wolf. That’s good, right?

Maybe not. In 2020, we saw huge numbers of people on paychecks being laid off or furloughed. They were reduced to running up credit card debt, and desperately trying to get through to the unemployment office for weeks and months on end. They had more time, but were less prepared to exploit that time.

On the other hand, the gig economy not only seemed to weather the storms, but even grew, becoming the backstop for people who had lost paycheck jobs.

Paychecks, as many have pointed out, have something of an addictive quality to them. They tempt you into unsafe cash-flow management behaviors through their very predictability. I certainly used to live less safely back when I was on a paycheck.

As an indie, I learned early on that I was in a glut/famine unpredictably cyclic economy. I learned the coping behaviors — build up higher reserves, keep multiple income options alive, and react fast to threats and opportunities. Paycheck people often never learn any of these disciplines.

So when storms hit, they are often caught unprepared. They’re living mindlessly paycheck-to-paycheck (even the well-paid ones; it’s the cost of keeping up with the Joneses), and when the layoff risk suddenly skyrockets — as it did last year — they have no contingency options in place that they can exercise.

Last year, white collar information workers were largely safe, and service workers bore the brunt of the fallout (a double jeopardy of being both more exposed to the pandemic, and to losing their jobs). This year, as longer-term impacts start to kick in, I think the blast radius of 2020-21 will only spread. Nobody is safe in this environment. Not even people celebrating Bitcoin nudging $40,000. Too many things have been disturbed too much.

For paycheck workers in their stick houses, in the cash, control, and community formula for resilience, ALL three elements turn out to be illusions linked to the paycheck.

• Cash: the paycheck is predictable, but not actually reliable. You could be laid off easily in a crisis. Your employer might simply buckle under the stress.

• Control: you don’t actually have control over your destiny. Your project, the darling of several VPs, could suddenly get canceled.

• Community: Sure you have a nice bunch of coworkers, with whom you used to get lunch pre-Covid. But if you lose your job, you’ll lose all of them too.

The last part came as a forceful shock to me when I quit my last job in 2011. I ended up keeping in touch with almost none of my friends from Xerox. I had lunch a couple of times with a couple of old colleagues, but then the entire work social network, which was such a huge part of my life before, just seemed to evaporate into thin air. If I hadn’t had my online life, I’d have become radically isolated overnight.

You don’t realize how fragile the paycheck situation is until you lose it for the first time. That’s what life in the stick house is like.

Life in the straw house, on the other hand, is paradoxically more resilient because it is more precarious. Random cash flow shocks are routine. A hoped-for gig doesn’t materialize. Another doesn’t pay. That invoice is delayed. This “passive” income stream is suddenly broken due to a billing bug.

Keeps you on your toes.

Now, I wouldn’t say I’m personally in a straw house situation right now. I’ve been at this long enough that I’ve actually managed to accumulate enough savings to count as a bit of a brick house. If all my income evaporated overnight, I could last quite a while before I got into real trouble (much longer than I could have back when I was on a paycheck). But I’ve definitely endured many a straw-house year.

To mix metaphors, you could say my house is a barbell house of straw and brick. I’m set up to be highly sensitive to the economic environment, but also have a savings runway.

But one thing I’ve carefully avoided for a decade now is getting reliant on anything that looks like a stick house — a paycheck-like income stream that is just predictable enough to lull you into a false sense of security, but not actually reliable enough to buy you enough time to reorient in a real crisis — once you wake up to it. While I’ve enjoyed bouts of pseudo-paycheck security in the last decade (like the year-long fellowship last year that ended just as Covid hit), I’ve never become reliant on them.

We’re only at the beginning of what promises to be a drawn-out economic crisis around the world. In the United States it is also a socio-political and cultural crisis. You’re going to have to pay careful attention to how your life is set up, what risks you are exposed to, how those risks are shifting week-to-week, month-to-month, and quarter-to-quarter, and how your option set is evolving.

So yes, it’s 2021, the Big Bad Wolf is up to his old 2020 tricks, huffing and puffing, trying to blow our houses down. But humanity has endured far worse, and through periods when almost the entire economy was a gig economy. These are bad times, but not apocalyptic times.

There’s only a small chance this environment will kill you (literally or figuratively, via livelihood destruction), but there’s a good chance it can make you stronger if you’re properly open to it.

We’re all pigs in this kind of environment, but if we build the right kind of house to ride it out in, we don’t have to get slaughtered.

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

Main Series

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

The Yakverse Chronicles

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

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

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

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

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

The Yak Collective

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

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

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

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

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

Looking Ahead at 2021

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

So if you have ideas or suggestions, do share.

See you in January!

Many years ago, I can’t recall where, I read an interesting remark about a cultural difference between the United States and Japan. Americans tend to seek out wide-open outdoor spaces when they are looking for perspective. The Japanese, on the other hand, tend to withdraw to small, intimate indoor spaces. I don’t know how true this is, but it strikes me as an intriguing distinction.

It certainly seems more natural, when seeking perspective, to head towards high ground. Towards places that afford you the opportunity to see as much of your environment as possible at a glance.

Like this view of the Los Angeles cityscape from a high viewpoint in Runyon Canyon. You can take in the sprawling scale of the city at a glance, and get a sense of your own place within it.

It seems less natural to head to places where your view of your environment is more restricted. Like this view from inside Descanso Botanical Gardens, a small park featuring a variety of micro-habitats but no views of the city.

This is a view in which, quite literally, you cannot see the forest for the trees. This is still outdoors, but closer to what indoor perspective taking feels like.

Call the two panoramic versus myopic perspective-taking. Depending on my mood, I enjoy both, but 2020 is a year that I think calls for the latter.

***

These literal, spatial understandings of perspective are what we unconsciously bring to the more conceptual exercises like annual reviews.

There are panoramic ways of looking out at your life in time — looking at the past and future at a scale of years or decades, in terms of long-term goals and plans. And there are myopic ways of doing so, in terms of the here-and-now entanglements that enmesh you viscerally in the present. Systems like GTD attempt to bridge the two, allowing you to zoom in and out to some extent.

But truth be told, you can’t adopt panoramic and myopic views at the same time. And trying to alternate rapidly just leads to nausea. Life is not quite as fractal as some wish it were. You must choose.

If you think about it, neither perspective — panoramic or myopic — is more natural in any absolute way.

Panoramic perspective-taking allows you to take in more at a glance — but at the cost of detachment. You can see the forest, but you’re not involved in the forest (or in this case, the cityscape). The view is missing a certain element of subjectivity; it lacks a certain calibration of personal distances; a certain set of distortions that make it your view.

Myopic perspective-taking on the other hand, limits the total scope of what you see, but gives you a richer sense of your own involvement and entanglement with the environment. A more visceral sense of your own personal relationship to what is around you. Perspective is even the wrong word, since it is a tactile rather than visual sort of sense-making.

Panoramic perspectives give you the best view of the contents of your life, but myopic ones, arguably, give you the best feel for the meanings of your life.

2020, it strikes me, is about meanings more than it is about contents. It is a year for myopic rather than panoramic views of your life.

***

Life in the indie consulting world is naturally more myopic. In 2020, it’s been doubly so, as we’ve been forced indoors and inwards, towards solitude and privacy.

The lifestyle drags your attention towards minutes, hours, days, and weeks, rather than towards quarters, years, or decades. Money is a gig-to-gig, invoice-to-invoice uncertain variable, not a promotion-to-promotion quasi-stable constant. Three, five, or seven-year plans — natural for larger organizational contexts — seem either deluded or self-aggrandizing in the indie context. Your clients may have such plans, but you are likely on the margins of them. You’re not truly a part of them.

I don’t know about you, but my life doesn’t have much long-term logic to it, and I like it that way. I like my days and weeks to be predictable, but my months and years to be unexpected surprises. I like the illegibility. It is anxiety-provoking, but still oddly satisfying.

The anxiety-provoking everyday uncertainty of indie life is perhaps why people in our world seem more attracted to exercises like annual reviews. It is less about perspective-taking, and more about imposing a temporary legibility and short-lived order onto life, before it all falls apart again by the end of January.

That doesn’t mean perspective-taking impulses are bad. It merely means you should be skeptical about panoramic perspective taking outside of the large institutions where they are natural. Do panoramic perspectives actually do anything for you? Or do they merely serve a palliative function?

The older I get, the more I suspect they function in palliative ways, especially for free agents.

The more of a free agent you are, the more the function is palliative, because freedom is sometimes just the flip side of anxiety, and panoramic perspectives, paradoxically, allow you to lock yourself up in a less free life for a while.

But there’s an alternative: what I call appreciative myopia.

***

Many of you are likely planning on doing some sort of annual review exercise, or have already completed one.

Chances are, you’re doing it the panoramic way — trying to rise above the weeds and climb to a hard-earned panoramic perspective of your life and work. If you are a fan of GTD for instance, you might start down in the weeds by taking stock of your various inboxes (while driving them to zero), assessing the state of play of various activities. You might be attempting to rise above it all to a grander view of your life. Framed perhaps in terms of missions, visions, five-year plans, and other such panoramic mental constructs. The effort is not unlike the effort of climbing up a hill.

This approach is perhaps especially tempting this year, given all the uncertainties around us. Setting 2021 goals will definitely provide some relief for a few weeks. Hell, maybe you’ll even set interesting decadal goals, for things to get done by 2030.

Those are not bad things to attempt, but let me suggest an alternative that you could try instead of, or in addition to, such panoramic reviewing: an appreciative-myopic perspective.

Rather than attempting to rise above the fray of action by forcing it into a transient legible state, consider just pausing and taking a close-up, myopic look at how you’re entangled in your world. At least for a while.

Stop doing things for a bit, but don’t step back. Instead step aside. What does that look like? What does your life look like in profile view, from a close adjacency, as opposed to a panoramic top-down view?

Curiously, there seem to be no systematic techniques for this. But I have a few ideas, based on what I seem to do naturally when I get stuck and panoramic perspectives don’t get me unstuck.

***

Look at your desk and your chair. What do they say about your life? Which books are within arm’s reach? Why? Which books seem untouched and forgotten? Why?

Pick up one of those long-untouched books and live in that adjacent possible life for a moment, in which that book was one of the heavily used ones.

How many pens and pencils are in your pencil stand? Why that number? What’s the story of each pen or pencil? If you favor pens, when was the last time you used a pencil, or vice-versa? Try writing something with the less-used instrument.

Do you have a favorite shirt? What about a shirt you almost never wear anymore? How about trying that on for a couple of minutes?

How has your life environment been disturbed by Covid, and what has that taught you about your life?

Where do you hang your masks? Where is the bottle of hand-sanitizer? What used to be where those new things are? Where are those things now?

Forget your five-year plans for a minute, and look around at your furniture. Did you buy any new furniture in 2020? How did it alter the flows and energies of your life? I bought a whiteboard and workbench after we moved to a new place this year, with a full-room home office for me, and that has definitely radically rewired the energy flows of my life.

Take a look at your inbox without attempting to drive it to zero. Who is emailing you and why? Look at your Sent and Drafts folders. Who are you emailing and why? What would a forensic investigator think about your inbox? What might they find sad about it? What might they envy about it?

Take a little walking tour of all your inboxes — the paper ones, the places where bookmarks accumulate, the various messaging apps. If you do any sort of journaling or writing, dip in randomly into the contents.

Forget processing any of it. What do the patterns of your communications say about where your attention naturally flows? Before you dive in to judge, reshape and optimize those patterns, ask yourself — what do those patterns mean?

If a novelist were to weave those patterns into a character study, what sort of literary invention would emerge?

***

Pretend you’re a consultant in your own life, attempting to make sense of it from the outside, based on the clues in the arrangement of things. You’re not trying to organize things, but interpret them, like tea leaves. Look at your life, but imagine the risks and responsibilities embodied by those things belong to someone else. What sort of person are you looking at? What detached advice would you give them?

You’re looking at the potentialities of your life, asking what-if questions about it, like any good consultant. What are the lives-not-lived next door to the one you’re living? What are the latent possible worlds adjacent to the one you inhabit everyday? The worlds that would take you only a slight shift in perspective to inhabit?

Because one of the weird things about the gig life is the amount of readily accessible potential you can access right next door to the life you live, but don’t. The meanings latent in your life environment are much less constrained than those in a salaried person’s life environment. Going indie is the big step, but it is often easy to forget that it is a big step primarily because so many smaller next steps open up once you take the big one.

There are many lives you could live, but none you have to live. All next door to the one you are living.

Yet despite the close presence of potentialities they work so hard to access, indies often end up living lives that are no more complex than the ones they left behind. All that risk, so little to show for it. All that extra optionality, so little extra dimensionality.

Forget about what sort of life is a five-year plan away. What sort of life is just a rearranged bookshelf away? Is anything really stopping you from living that life instead of the one you are?

Look at your life environment like a crime scene or an archaeological dig. Does it reveal your life to be neat and tidy or messy and chaotic? Does an anxious or serene person sit in that chair?

What sort of person lives here? What other kinds of persons could possibly live there? Could you be one of those adjacent possible alt-yous instead of the person you are?

Try messing with things a bit. Turn your chair around so it faces the other way. Does it make you anxious or feel surprisingly more right?

Drink coffee from a mug you haven’t touched in a while.

Rearrange the icons on your computer screen. If you’re an everything-in-folders type of person, open all the big folders up and tile them so it’s overwhelming. Stay with that feeling for a while.

If you’re an everything-in-view type, try shoving it all into a directory to experiment with what a clean desktop makes you feel. Stay with that feeling for a while.

Disturb your life ever so slightly, and watch how it vibrates around in its adjacent possible band. Listen to the music of those vibrations. What key is it in? Could it be tuned to a different key?

Resist the urge to judge, organize, make to-do lists, or tidy up. Hold off on those resolutions and goals. Don’t ask yet whether it sparks joy.

Ask what all of it means. And what else it could mean.

***

Rather than taking stock of your world, to reshape it top-down, which is the point of panoramic perspective-taking, appreciative myopia is about re-sensitizing yourself to the flows of your world, by making yourself a stranger to it.

Surprisingly, even though we spend hours and hours every day in our life environments, we get so used to inhabiting them with an action-oriented mindset, seeing them only in instrumental ways, in light of the next thing we want to do (or worse, our five-year plans), we rarely ever see them for what they are, and what they reveal.

The older (and more set in my ways) I get, the harder it gets to see the grooves and ruts of my life, but the easier it gets to just flow along in them. Even though changing course would not be as hard as it once was, in another life.

The panoramic perspective is easy. I don’t have to stop to take stock to simply rattle off all my major projects and activities, and their respective current states. Off the top of my head, I can approximately tell you the state of various gigs, and the overall financial condition of my consulting practice.

What I can’t see is all the little things that have crept in and accumulated unnoticed, as the emergent ruts and grooves. The fields and flows shaping the tempo of my life.

The big picture is not the hard picture to stay aware of. It’s the little picture. The close-in, close-up environment of life. The tip of your own nose. The weeds are hard to see, both when you are caught up in them in the heat of action, and when you attempt to step back from them, in a spirit of earnest contemplation, rationalization, and optimization.

Stepping back from your life is easy. Stepping aside from your life is hard.

Stepping back inevitably takes you towards the detached view, the panoramic view. And the legibilizing, confining, palliative intervention.

But stepping aside? It makes you a stranger to your own life, able to see it once again for what it is and could be, rather than what it does. As a state of being rather than instrument of doing. As a functionally unfixed situation that can mean many things, rather than the state of play of a specific grand plan that can mean only one thing.

So in a year when visiting family and friends is going to be hard for most of us, maybe the thing to do is to visit a very familiar stranger you probably haven’t visited in a long time — yourself.

One of the subtler perks of institutional life is that there is something it is like to go deep.

• If you are in the private sector, you can go deep in a particular business function (such as marketing or finance) or in some satisfyingly rich domain expertise area, such as say semiconductor processes, supply chain operations, or esoteric financial instruments.

• If you’re a career public servant in government, you can go deep in some area of public policy or administration with a long history, and a satisfyingly complex nerd-out domain structure, such as housing or wildfire management.

• If you’re in academia, you can get your PhD and tenure, and then go deep on something nobody else has gone deep on before (though many don’t actually do that, choosing instead to become conference/journal scenesters and fund-raising mavens).

• If you’re in the nonprofit world, you can hope to go deep on issues and problems of a particular domain, be it is huge and mainstream like healthcare, poverty, or education, or obscure and marginal, like the fate of some uncharismatic threatened species the public doesn’t care about.

Depth in this institutional sense is something free agents often miss about the paycheck life without realizing it. It manifests as an urge to try and develop sectoral or functional expertise, write a book, or seek professional accreditations.

But often, such efforts (which ultimately emerge as unconscious responses to a felt lack of depth) fail to scratch the itch. They remain unsatisfying. Your life as a free agent feels trapped in the shallows.

Depth in Captivity

The possibility of depth in institutionally organized sectors is a function of their being institutionalized. It is, in a sense, depth in captivity. An indoor sort of depth.

When free agents who have experienced institutional settings feel an unconscious lack of depth in their work, but react to it without conscious processing, it leads to a grasping towards ersatz signifiers of depth that resemble those available in institutional settings, but don’t actually point to deep substance the way intra-institutional “real” ones often do. That’s why they are unsatisfying. Depth in freedom, an outdoor sort of depth, does not work the same way as depth in captivity, so trying to model the former on the latter fails.

It’s like calling yourself a CEO when you’re a one-person company. The title simply doesn’t mean anything close to what it means in a Fortune 500 company. It lacks depth.

But people try anyway. You can take the free agent out of the institution, but it’s not easy to take the institution of out of the free agent.

Indoor depth is easier because institutions supply a generally thoughtful extrinsic coordinate system, a map of sorts, of expertise within a particular territorial scope. They define a down direction where things get deep, difficult, and satisfying to master. And they supply an environment that automatically values the fruits of such mastery, and provides adequate extrinsic rewards if you do succeed in going deep (and care about the extrinsic rewards, which many don’t, despite getting them).

If you’re inside an organization, generally all you have to do is work up the courage to test your talents in the local depth direction. These depth vectors are often shared and portable across a sector. So for example, in the computer industry, “down” points towards the silicon level for engineers, and if you’re recognized as “full-stack” deep in one company (in a silicon-to-cloud sense), you’ll be recognized as deep in another company if you switch jobs.

The gig economy is not like this. Outdoor depth is not like indoor depth. Depth in freedom is not like depth in captivity. From gig to gig, very little carries over in any obvious way.

It is not at all clear what it even means to be deep in the gig economy. I’ve spent nearly a decade in it, and worked for dozens of clients in a dozen sectors. I have certainly experienced freedom. But have I acquired “depth” in freedom in any sense?

I think so, but it wouldn’t be obvious from the outside even if you’ve known me and my work well through the whole decade (as a couple of long-term clients have). Whatever depth I might have developed is not very legible.

Möbius strip. Source: Hamish Todd, Wikimedia Commons.

The thing is, the gig economy has no natural orientation with an obvious, but meaningful sense of up, down, or sideways. At best there is “above the API” and “below the API.”

Some parts of it can even seem like they’re not orientable at all, like a Möbius strip (mathematically, “up” is an ill-defined idea on a Möbius strip because if you go 360 degrees around the strip, “up” will be pointing the other way. This is demonstrated by the one-clawed crab in the animation above).

Is this a problem for the gig economy?

Certainly not for everybody in it.

Bound in Shallows

There is no denying that at least the voluntary and above-the-API part of the gig economy has more than its fair share of shallow dilettantes. People appreciate and enjoy the freedom to skip from topic to topic, sector to sector, exulting in whatever superficial drive-by value they can add (or scams they can get away with).

With apologies to Shakespeare, their lives are bound in shallows, but not in miseries. They don’t suffer angst due to a felt lack of depth.

Lucky for them. This is not about such blithe spirits. This is about you and me, the kinds of self-scrutinizing snowflakes who are likely to be miserable in the shallows. I’ve served enough time in the shallows to know what it feels like, though fortunately not enough for it to have damaged me significantly.

So what is it like to be bound in shallows?

Let’s say you went and did a glossy presentation/workshop for a company, along with a few exercises for participants. You got the gig because the VP of HR is your buddy, and you don’t think too hard about why he gave you the gig. You got paid $10,000, and felt really good about yourself. It’s not just a nice payday, it’s affirmation!

Yay, your XYZ Master System™ got validation! It is now a Proven Process™ used by a Fortune 500 company. Quick, get those professional headshots done and put up a sales page!

On the strength of that first sale, and some vigorous and glossy marketing, you convert a few of the leads, and sell a couple more instances of the workshop. They go less well. Things get harder from there on out.

You hear whispers from the participants that your workshop was a waste of their time and the company’s money; that you don’t really understand anything about anything that’s important to them or their work.

Hmm, maybe the fact that you got paid, and even got further leads, doesn’t actually equal value? Maybe vanity metrics don’t measure depth?

But wait! It’s not all grumbling by the sour old curmudgeons! You do get a small handful of eager, enthusiastic participants reach out to you later and thank you effusively for the inspiration and great ideas. But as you meet more of these people, in the back of your mind, a gnawing thought begins to grow — these people praising or thanking you — they don’t look or act like the players in the client organizations. In fact, they look and act like the opposite of the players. They look like the insecure, clueless NPC types who are not in any significant conversation, inner circle, or tribal cabal. Nothing is riding on their success or failure. Are these really your people?

Maybe the unsatisfying response to your workshop demonstrates your own lack of appreciation of what depth means in the world outside your own head?

This is a moment of truth. Setting aside the grifters, who simply move on to the next scam once the last one runs out of steam, reactions to this kind of moment of truth pick out two kinds of people.

The first kind is those who go into immediate rationalization mode. Phrases like these tend to crop up in the rationalizations:

• “They are trapped in their silos, they don’t appreciate fresh thinking.”

• “I only deliver insights and inspiration, it’s for the clients to follow through.”

• “I am a generalist/polymath/connector. I connect ideas across domains.”

• “The ones who appreciate me, they should be the players. The actual players are just focused on quarterly results and have no imagination.”

• “It’s a hidebound old-fashioned company; they’ll never change. But I guess I’ll take their money. I know what I’m worth.”

These phrases sometimes (but vanishingly rarely) point to real truths about what you’re doing, but far more often, point to a lack of genuine depth in what you’re up to. They’re a sign you’re possibly seeking second-rate affirmation from the wrong people and ignoring the warning signs of being ignored by the right people.

Where the “right” people — call them players if you will — are the ones who have figured out what “depth” means in a specific world, and are pursuing it.

The first kind of person never seems to stop to ask: If what I offer has no relevance to what is “deep” in any given neck of the woods, why am I doing it?

The second kind of person is the kind that doesn’t attempt to rationalize or repress this feeling of lack of depth, but instead, decides to chase it down.

The Cost of Depth

Depth is an ambiguous concept in the gig economy, so let’s try to understand the simpler case of depth in institutionalized settings.

Here’s a handy heuristic to navigate by: Deep recognize deep. Shallow recognize shallow.

Depth is costly. Depth demands thankless, invisible, solitary effort. Depth takes time. Depth demands that you master difficult, significant, matters that others are not even aware are important in the world, let alone appreciate or praise, even if they recognize the value of the end results of depth:

• Do you know what it takes to make a Covid19 vaccine?

• Do you know what it takes to harden electronics to work in outer space?

• Do you know what it takes to work compassionately with homeless people to improve their lives?

• Do you know what it takes to spend a decade trying to prove a single theorem?

Depth. Depth. Depth. Depth.

Certainly, being in an institutional setting makes it easier to pursue depth in some ways, by removing certain time or money constraints. But the choice to pursue depth, and the temperament it takes to actually do so, have nothing to do with being in an institutional setting.

Navigating depth of any sort lends a certain paradoxical combination of lightness and substance to how you carry and present yourself. A twitter buddy has the awesome handle @gravitylevity that really captures this state. Depth looks like gravitas and lightness in the same package. Not surprisingly, he is a well-regarded theoretical physicist. One of the institutionalized callings that is recognized as “deep” right out of the box in our society.

Depth in this sense is unmistakeable to others who have also been navigating depths of their own. But to those bound in shallows, it can be hard to tell apart from imitations.

This is why I like to say, depth recognize depth.

Even when people are from very different worlds, where depth means very different things — like say a trauma surgeon with 20 years experience meeting a musician with 20 years experience — they will recognize in each other the ongoing growth and accumulating substance that are the mark of an active pursuit of depth.

Often this is even true when two people are mutually hostile and don’t value the depth represented by the other, like theologians of competing religions who have each spent a lifetime mastering their respective religious texts.

On the flip side, shallow recognize shallow.

Insecure people who lack a depth dimension in their life tend to recognize each each other’s insecurities and voids, and cluster together for mutual comfort and support. Underneath shared ritual complaints and games, bemoaning a world that has somehow failed to appreciate them, at some level they recognize that they bear part of the responsibility for never having gone deep on anything. Whether through lack of courage, lack of confidence in one or more of their talents, or inability to care enough about something difficult, deep down, shallow people know they’re shallow.

In the institutional world, depth is a recognition of an intrinsic pattern that is then verified by extrinsic markers and signifiers, like titles, credentials, wealth, and so on. The additional verification step makes it easier to recognize depth. Equally, shallow is a pattern marked by certain tendencies of mutual association, and a different set of extrinsic markers.

Either way, shallow and deep are easy to tell apart inside an institution. The paid-up costs of depth are hard to fake, and easy to detect if you’ve paid them too.

Depth in Free Agency

The principle applies to the free agent world too, but is much weaker and more probabilistic: depth recognize depth, shallow recognize shallow.

Take a hard look at the sorts of people you attract. The sorts of people who provide validation for what you do, and the sorts of people you secretly wish would provide validation.

Are you attracting deep people? If so, you too are deep.

Are you attracting shallow people? If so, you too are shallow.

There is no dishonor in being shallow — so long as you own it, and do it in a principled way without turning into a grifter. I have nothing but respect for people who take on light, undemanding roles in the world, know it, and accept that they’ve chosen to live a life that is depth-limited in some sense.

This is fine. Really. I’m that way Tuesdays and Thursdays myself.

Less honorable is people running scams and grifts, pretending that shallow things are deep, and doing so long enough to make personal gains and move on. This is distasteful, but not too bad in my book. There is something charming about grifters and scam-artists who know they are grifters and scam artists.

The people I find… troubling shall we say?… are the ones who are in deep denial about the lack of depth in what they’re doing, go down a self-destructive spiral of rationalization about it, and yet do nothing to meaningfully pursue depth instead of (or at least, in addition to) self-destruction.

The free-agent world is full of such people, and there’s a reason for that. Many are people who left the institutional world because they failed to access the depth dimensions of wherever they were, due to whatever fair or unfair reasons. They either lacked the capacity for shallowness or self-delusion required to hang around as an NPC where they were, or were kicked to the curb at some point during a round of fat-cutting.

Either way, they now find themselves in the free-agent world, acutely (if unconsciously) sensitive to the lack of depth in their lives, the psychological toll of that condition, and in addition, newly aware that they now have absolutely nobody to blame but themselves.

There are no more evil bosses to blame. No soulless large corporate bureaucracies crushing your spirit.

Your lack of depth is now 100% your own problem.

And if you lack the blithe spiritedness to not be bothered by it, or are burdened with too much of a conscience to make a happy grift of it, you are in trouble.

You must find a depth dimension or suffer the consequences of being bound in shallows and miseries.

Seeking Depth

Obviously, seeking depth in the non-orientable Möbius-strip wilderness of the non-institutionalized world is no easy matter.

Not only is it hard to define what it means, or recognize it when you find it, you have to accept that you’ll never again receive any sort of entirely legible extrinsic validation for it.

Your depth, or lack of it, will have to remain entirely a matter of intrinsic substance that is either recognized or not by a scarce handful of people you yourself consider as possessing depth of the sort required to see you.

Tough, huh?

Let me offer you one very easy hack to start with — don’t make the mistake of trying to be all deep, all the time.

Depth is not the same as continuously inhabiting a humorless, relentlessly “on” high-gravitas persona that never lets you off the hook.

Depth is not the weight of the world on your shoulders. Depth is not identifying with Atlas Shrugged.

Depth is not about self-importantly retreating from social media to do “deep work.”

Depth has room for downtime, shit-posting, jokes, silly and absurd tiltings at windmills, and so on.

Depth has time to tweet if that’s what it wants to do with its downtime.

Depth does not need the protection of artificial attention walls. It is only shallow work that can be disrupted by a lack of walls around it.

In fact, it is the security of having access to a depth dimension, which you can retreat to anytime you start feeling too shallow, that creates the light-heartedness necessary for your chosen forms of restorative shallow silliness.

In fact, being all serious, all the time, is a clear tell that you lack a depth dimension, or are straining too hard to cast a relatively shallow life endeavor in a “deep” light.

How do you seek depth?

As I said, it is not about “Deep Work” (see my old post Semicolon-Shaped People on my other newsletter, Breaking Smart, for my critique of what I’d call shallow understandings of the idea of depth).

The trick to depth is compounding. The external heat signature of depth, even without an extrinsic coordinate system or frame of reference, is the presence of a compounding phenomenon. Something is building on itself, and snowballing. I wrote a blog post about this almost a decade ago, The Calculus of Grit, that has remained one of my most popular ever. The short version — memorize the 3R’s formula. To quote myself:

In endeavor space, field, domain and years of experience get replaced by three variables that lend themselves to a convenient new 3Rs acronym: reworking, referencing, releasing (well, technically, it is internal referencing and early-and-frequent releasing, but let’s keep the phrase short and alliterative). I believe the new 3Rs are as important to adults as the old ones (Reading, wRiting and aRithmetic) are for kids.

If this approach works for you (there may be others, but this is the playbook I know and can vouch for), then for extra credit, try and find the right small group context that can accelerate your depth-seeking. What I call a crucible (see another old post of mine, The Crucible Effect) — a group of people vying with each other and making each other better at something.

Think of a crucible as a small, local, informal depth-vector consensus of under a dozen people. It may or may not also be a collaborative squad, or a full-blown scene, but it will help you dowse for your own sense of “down and deep.”

Those pointers are all you should need to get started exploring the vast topic of seeking depth, so I’ll just close with a bit on managing your expectations.

Managing Expectations

Depth is something you’ll eventually start recognizing in yourself. And you’ll know is not delusional because compounding phenomena are hard to fake, especially to yourself. If something is snowballing in your life, there will be a positive energy to it, a growing sense of substance to it, that will feel real to you.

But that’s it. That’s all you get for sure. The feeling of no longer being “bound in shallows.” The feeling that there is something it is like to be you, defined by a certain pattern of depth-seeking, a certain sense of riding a real tide out to sea.

Nothing else is guaranteed.

If you expect more — validation from others, extrinsic markers widely acknowledged to be impressive, praise, acknowledgment that what you do is in any sense “important,” or “historically significant” or “making a dent in the universe” — you’re expecting too much.

If you expect to summarize it for others in a compact way, in the form of something like a life-mission statement, you’re probably expecting too much, though some people seem to manage it.

What about deep recognize deep?

You may get some of that, though not as much as you can expect in an institutional setting.

And it will never feel like validation or valuation. It will never be more than a look, a glance, a double-take, a certain underlying seriousness in how people engage with you, even if they do so lightly.

But that recognition is, in a sense, content-free. It carries no value-judgment, respect, validation, or praise. It is what is philosophically/poetically known as “being seen.” A sign from others you see as existing that yes, you exist too.

Occasionally, there is an energizing positive valence to it when it comes from an older person who has logged more depth than you simply by virtue of having been alive and digging longer (hence the “senpai notice me” meme). Obviously this gets less frequent and more neutral as you yourself age, and diverge away from the trajectories of potential senpais.

Other times, it is no more than a momentary sign that you’re not entirely alone in your little world. You yelled can you hear me now? at the universe, and somebody answered yes.

And sometimes that is all you need to take yet another swing, to wake up to see yet another day as a new day, because you made it so, starting with that first consequential decision to go free-agent.

Because that’s ultimately what seeking depth in freedom is all about: making every day feel like a new day, rather than bound in the shallow reruns of days already lived.