Depth in Freedom – art of gig archive

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.