Art of Gig: 2020 Roundup

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. đź”’

  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.đź”’

  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 đź”’

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

  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? đź”’

  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. đź”’

  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. đź”’

  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” đź”’

  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. đź”’

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

  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. đź”’

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

  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.đź”’

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

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

  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. đź”’

  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.đź”’

  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. đź”’

  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. đź”’

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

  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. đź”’

  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. đź”’

  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. đź”’

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? đź”’

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

  3. Yakverse: Infinity Gig: In which the Yakverse Chronicles head towards a stunning resolution. đź”’

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!

Appreciative Myopia

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.

Depth in Freedom

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.

Don’t Build a Hill to Die On

A reader (I’ll call them X), asked me for advice on a broad situation, concerning someone close to them who is relatively new to the indie game, which I think is of general interest. My summary, generalized version of X’s question is:

Why can’t they see that I have the solution to their problem?

Clearly, if you can answer this question effectively, you’ll make changes in how you position, present, and market yourself, which will result in more leads, which in turn will lead to more gigs, and to you living happily ever after, validated, fulfilled, and rich.

So it’s an existential question. It’s the product-market-fit question for indies.

The account X shared with me is something of a mini-essay in itself, and it walks through their systematic attempt to tackle the question. Their attempt falls naturally into a 5-stage analysis pattern that I think is pretty common among healthy minded, thoughtful and introspective people. It leads thoughtfully and inexorably to building a hill to die on and then… dying on it:

  1. The evidence of value stage

  2. The alignment of valuations stage

  3. The systems lamentations stage

  4. The building a hill to die on stage

  5. The martyrdom stage

The first two stages are great and you should do them. The last three stages are bad, and you should replace them with a road-less-traveled alternative set of stages I will suggest.

I’m going to break up X’s mini-essay into pieces, and respond inline the way I would in a 1:1 email consult (which I don’t offer).

Evidence of Value

Reader X gets off to a great start here describing the situation:

[A freelancer] has evidence that what they do is valuable and useful – some past results that led to happy clients and measurable wins. People they’ve worked with have been challenged and then delighted, and have made more money.

I love this as a starting point for introspection. Many indies just assume what they do or have to offer is valuable, simply because they enjoy doing it, and feel they are good at it. They let go paychecks, but not the dose of validation that comes with it like clockwork.

From there it is a short leap to developing a simmering resentment when the world doesn’t deign to agree with them.

Looking for evidence that what you do is seen as valuable by others, and that they’re not just being nice, or flattering your conceits for their own reasons, or avoiding conflict, is hard to do. But if you don’t start that way, you are at severe risk of extreme self-delusion from Day 1. A delusion that you might never break out of.

So interrogate your presumption of value skeptically.

X believes they did that, and found evidence of value, and I believe them. So let’s call Step 1 done, and done well.

Alignment of Valuations

Our reader gets Step 2 right as well, looking for alignment of valuations, even though they fail to find it:

But … the broader field (copywriting/messaging in this case) is pretty illegible and full of bullshit. Lots of potential clients undervalue the work, assume they can do it themselves and just need extra hands to make it happen, or think it’s a “nice to have”.

Now we’re getting to the heart of the matter. It’s one thing for clients to be happy, and even unexpectedly happy/delighted at having gained greater insight into their needs.

But that still doesn’t mean your respective valuations are aligned. In particular, valuations of work between you and the client have to be aligned in a way that they want to pay you what you want to be paid.

Your client might agree there is evidence of value. They might even agree on the price. But there’s a strong possibility they’ll stop short of agreeing about the need to actually buy right now.

X’s problem here is a special case popularly known as the aspirin vs. vitamins problem.

The indie here thinks they’re selling a must-have service (aspirin, a cure for serious business headaches). The client thinks they’d be buying a nice-to-have service (vitamin, a nice-to-have well-being boost, but not having it isn’t going to kill the business tomorrow).

A client being willing to half-ass something for themselves instead of paying someone with experience to do it right is a clear sign that they think of that something as a vitamin rather than an aspirin.

To make it more stark, think in terms of surgery versus personal training, or even life-saving surgery (for heart disease or cancer for example) versus personal training.

I don’t know about you, but I wouldn’t attempt surgery on myself, or defer urgent surgery simply because I’m cash-stressed. I’d definitely get myself a surgeon and go into debt to pay them if necessary.

But I’d probably be willing to design my own fitness routine rather than hire a personal trainer if money is tight. In fact, even if money isn’t tight and it’s just simpler to do my own routine. Under some very special conditions, I’d pay (and have done so) for personal training (someone I find easily and get along with, easy scheduling at a gym I go to anyway, etc etc).

There are other ways alignment of valuation can fail besides the vitamin-aspirin impasse, but however it fails, the work is usually not being undervalued so much as being judged unnecessary, in a strictly logical sense. It is being contingently valued, its value locked away behind an if statement.

Every business person probably contingently values something like copywriting at a fair market value, but with an if clause: I should pay the market rate for quality copywriting if such and such vague conditions hold.

Undervaluation is easy to walk away from. If you don’t have identity hangups or insecurities, a lowball offer is both easy to walk away from, and easy to accept without damage to self-esteem if you’re really under cash stress. Oddly enough, the less lowball offers offend you, the less likely you are to get them at all. People can sense when somebody is not attached to a fixed idea of their market value, and don’t even try to lowball them.

But contingent valuation is a different game altogether. Contingent valuation means you disagree on which world you inhabit.

You think you live in aspirin world. They think you live in vitamin world. The two pills might even cost the same, and you might agree it’s a fair price.

Yet the aspirin will almost always get bought, the vitamin almost always will not. As sales people like to say, people only buy two things: happiness (vitamins) and solutions to problems (aspirins). Most above-the-API indies are in the vitamin game.

The mistake they make is trying to cast vitamins in aspirin roles. This leads to Stage 3: Systems Lamentations.

Systems Lamentations

A contingent valuation impasse will inexorably draw you into dangerous territory, where analysis starts turning into paralysis. Here’s X going there:

When they ARE looking, they’re usually focused on the symptoms, rather than realizing that there’s a deeper malaise.

This sort of sentiment commonly comes up in assessments of why clients are making the (unfavorable to you) decisions they are, like doing things poorly themselves, hiring cut-rate alternatives, trying to lowball you, or perhaps most galling of all, signing up for some scammy overpriced offering next door to yours.

Versions of this sentiment include:

  • “They’re focused on band-aid fixes”

  • “They only care about the short-term/next quarter”

  • “They are not seeing the root cause”

  • “They have a culture problem of not valuing X”

  • “They just want to act like they want to solve the problem”

  • “They want to sweep it under the rug/paper over it”

  • “They just want the theater”

These are what I call systems lamentations. Systems theory analysis conducted by way of predictable laments.

If these laments sound familiar, and you often trot them out in your analysis of failed gigs or leads that don’t convert, I have bad news for you.

Usually, when you lament that the client is missing some “root cause” or “deeper malaise,” (or doesn’t care as you think they should) you are the one who is missing something by being trapped in a functionally fixed perspective.

Ie, this is the “when you have a hammer in your hand, everything looks like a nail” stage of paralysis. Of course if you offer good copywriting, you’ll be primed to see something upstream of bad copy as the root cause or deeper malaise behind the client’s troubles. Of course if you offering sparring services, the answer is sparring about root causes. Of course if you offer to crunch data in R, the root cause is insufficient data-drivenness in their culture.

The funny thing is, if you’re smart and good at wielding your hammer, you are probably even right.

The problem is, you being right doesn’t mean they are wrong.

See, to be an indie, you have to internalize the Five Noble Truths of systems thinking:

  1. Thar be blind men and elephants: There are many correct ways of looking at a system, all of them partial, none strictly superior to others.

  2. Everybody has a root-cause lament: Everybody always believes the system is broken in some fundamental way, and has an opinion on what the “root cause” is from their point of view. This is nearly always an opinion that renders them helpless, and is therefore expressed as a lament.

  3. Nothing is broken: Complex systems are almost never actually broken. They’re just not always working for you. Even Covid hasn’t “broken” healthcare. It has just revealed that healthcare systems generally aren’t working to protect the health of citizens.

  4. There are no bad systems thinkers: There are just people who are looking at the system from different perspectives, subject to different incentives, and each with a different opinion on how, why, and where it is “broken” in some fundamental, root-cause way. Systems thinking isn’t a skill. It’s a scope of interest.

  5. There is always a righteous HiPPO: Every system will evolve to an equilibrium that validates, but does not actually address, the specific lament underlying the highest paid person’s opinion of what the root cause is. Every thoughtful person looking at the system is right about their view of the root cause in some way, but the HiPPO is in addition, uniquely righteous, representing the default morality of helplessness enveloping the situation via a default lament.

In other words, most complex systems in equilibrium are a case of a blind HiPPO touching an elephant.

Okay, I admit, this whole newsletter issue has been about trying to set up that particular joke (I was going to make a cartoon of it but couldn’t draw a good blind hippo).

You cannot dislodge a system from a hippo-default-lamentation equilibrium by convincing the hippo that your lament is superior to theirs. If you’ve come this far, and begun circling a pet lament that seems to apply to every failed gig or unconverted lead, you’ll almost certainly move on to the next grim and futile stage: building a hill to die on. Often in the form of a website.

Building a Hill to Die On

Having gotten stuck trying to win gold in the Lamentation Olympics, in a rigged game that’s designed to award gold to the HiPPO on the scene (silver is a set of steak knives), X reports:

The freelancer has created some valuable assets that go towards proving their expertise –- articles, a tool. And they’ve put those “out there” a bit. But there’s not a great deal of traffic to their website, and little response from those who do find it. Most of the work they’ve won is through contacts, and it feels like all the work they’ve done on creating a corpus of work and putting themselves “out there” hasn’t really made any impact at all.

Clearly the problem isn’t that they don’t understand marketing tactics — they offer copywriting and messaging services after all, and have evidence that they’re good at it. And like I said, I believe them.

So what’s going on?

When you find yourself competing for steak knives in a Lamentation Olympics contest; when you find yourself trying to boil an ocean by identifying root causes; when you find that trying to sell vitamins has led you to arguing about the kind of world we live in — you’ve fallen into the trap of building a hill to die on.

You’ve fallen into the trap of trying to “prove” that your way of looking at the system is the “right” way. That your lament is superior to the HiPPO’s lament.

“Proofs of expertise” are often works of lamentation art (though I’m not saying that’s the case here). Design fictions from the world you wished you lived in. A world where what you offer is aspirin, not vitamins. Necessary pills rather than contingent.

A manifesto section on a website providing context for the showcase of expertise is often a reliable tell that you’re looking at a lamentation artwork gallery.

In the parable of the blind men and the elephant, this would be like the blind man touching the tail of the elephant trying to “prove” that the system is a rope, while the client, a blind man touching a leg, is convinced the system is a tree. So the marketing exchange is essentially:

Blind Consultant: Here is a blog post and calculator tool showing how to fix broken ropes

Blind HiPPO Client: Interesting, but I’m working on fixing my broken tree here. If I’m ever in broken-rope world, I’ll call you.

This is not a winnable conversation because there isn’t one right way to view the system, and no absolutely compelling reason to view it in any particular way. So most people are naturally attached to their way of viewing it.

The best tactics — great website, great SEO, scintillating copy, a great little calculator tool — none of it matters if the client doesn’t share your systemic view.

So what happens next? Well you built a hill to die on, so what do you expect?

Martyrdom

Naturally the next step is to actually die on it. Often the sign that you’re doing that is taking solemn note of the Triumph of Evil over Good in your neck of the woods. It’s a sort of martyrdom speech from the gallows.

Lo and behold!

Finally, this freelancer is also scrupulously honest and diligent. One of the big challenges is seeing a load of people who appear to be complete chancers or lemons raking in loads of money, while they have turned away or lost work through being honest. The fact that scammers seem to win while this freelancer can’t seem to catch a break … There’s a sense of how unfair that is that forms at least part of the general “work is dry” challenge.

This martyred analysis is not wrong (in fact it’s more right than they seem to realize for reasons I’ll get to), and of course being scrupulously honest and diligent is a wonderful thing. It just doesn’t save you from the dying on the hill you’ve built. It merely cloaks your martyrdom in honor and nobility.

I mean of course there are scammers and grifters raking in loads of money from suckers everywhere.

Of course there is going to be a lemon market right next door to every real value exchange around deeply stuck systems.

Of course the world seems unfair because the bad actors chase out the good.

But it’s still you, the Good Guy, dying on the hill you’ve built yourself. Not them. Planting a flag and making a little speech isn’t going to change that.

So let’s back up to where things started going off the rails.

Validate, Resonate, Create

As I said in the beginning, the 5-step analysis model that derails thoughtful introspection and sucks you into martyrdom actually begins with two goods steps, but then falls apart at the system lamentations step and goes downhill from there.

To short circuit that, you need to go down a different path once you’ve assessed the alignment of valuation situation. Instead of:

  1. The evidence of value stage

  2. The alignment of valuations stage

  3. The systems lamentations stage

  4. The building a hill to die on stage

  5. The martyrdom stage

We’re going to go:

  1. The evidence of value stage

  2. The alignment of valuations stage

  3. The renouncing validation stage

  4. The building a resonance stage

  5. The creation stage

Ie, at the fork in the road after Stage 2, we’re going to go down a road less traveled.

Renouncing Validation Stage

Systems lamentations (go back and review the “tells” in the form of pet diagnostic phrases that go nowhere) are a kind of learned helplessness.

They are a mark of attachment to a helpless perspective of a system rooted in the misguided belief that it is the only true perspective.

We tend to get attached because the perspective has the happy property of casting us in a permanently valuable light.

If the world is always this way, then what I do is always worthwhile (even if nobody actually pays me to do it).

Renouncing validation is a simple idea. You let go the need to have others validate your view of the world you both inhabit. So when faced with a valuation misalignment…

Instead of mounting a principled defense of your perspective, you simply abandon your perspective and go validate theirs.

You’re both likely right about your diagnosis of root causes, and neither of your laments really matters. You don’t get systems unstuck from bad equilibriums by finding the right way to lament, or by getting validation for your specific lament.

So renounce the need for validation, and commit 100% of the validation budget to the client. They need it more than you do.

Operate as if their way of viewing the system is the only correct way, modulo things like simple factual errors. Assume you live in the world they believe they live in. It’s almost always a harmless assumption.

For bonus points, sing their laments more exquisitely than they do, to the point that they trust your voice more than their own. Not only do you see the world their way, you see it their way better than they themselves do. There is no disingenuousness in doing this because laments simply don’t matter. Every lament points to a roughly equivalent possible world you could inhabit around a complex system that feels broken. You’re equally helpless in all of them. Laments represent distinctions without differences among a set of possible worlds.

Just don’t get attached to any lamentation, yours or theirs. Renouncing validation for your laments in favor of unconditional validation of theirs leads to trust, which leads to the possibility of the next stage: resonance.

Resonance Stage

The next stage is building resonance rather than a hill to die on.

What do I mean? I mean you simply try to jam with them while tapping into your personal nerd energy. You’re not trying to “prove” anything. You’re not getting into vitamin versus aspirin arguments. You’re not doing ROI assessments or showcasing expertise at anything.

Now that you’re seeing the world from their point of view, by simply adopting it rather than arguing about it, you have enough of a common ground to start jamming.

Whatever it is you do — writing good copy, analyzing data, developing architectures, analyzing strategies, fixing technology roadmaps, writing code — show them the joy of doing it your way. The unbridled nerd energy that can be unleashed by going down an energizing bunnytrail of positive-feedback action. The exuberance and generativity you yourself feel when you get a good gig that allows you to nerd out in your favorite way. They’re not paying for a specific service. They’re paying to unleash broader reserves of energy from somewhere, and they probably don’t care much about where. If they can vibe with your nerd energy, they’ll pay.

The mark of building a hill to die on is planting a flag on that hill. A proud flag that flutters in the wind, proclaiming the values and truths you hold dear to all the world, while you die slowly clutching the flagpole.

In the indie world, you either die a martyr, or survive long enough to see yourself turn into a nerd. And to turn into a nerd is to open up a unique portal.

The opposite of planting a flag is opening a portal. Building resonance is about opening portals instead of planting flags.

I wrote about this in a 2014 blog post that is one of the few I revisit myself to keep myself reminded of (and energized by) this principle. If these ideas are new to you, I recommend you stop here and go read that post before continuing. It’s a brain-dead obvious idea — but only after you’ve learned and internalized it for the first time.

Portals eat flags for lunch. The offer seductions that offer an escape from your client’s pet laments. Instead of saying “my view of why your world sucks is better than your view of why it sucks,” you say “I agree the world sucks, in exactly the helplessness inducing way you say. Here is an energizing place to escape to, and maybe find a way out.”

Portals don’t just offer escapes from helplessness, they offer energizing escapes and the possibility of empowered returns with newfound agency.

When you go through a good portal along with a good guide, you emerge refreshed. Your own laments weigh less heavily on you. You likely still see the “system” the same way, and diagnose the “root cause” the same way, but now you bring fresh energy and imagination to the party. Instead of feeling helpless, you feel you can take it on and perhaps win or at least shake things up. Or if not, at least make dealing with the suckage worth it.

This incidentally is the lesson in the existence of lemon markets next to yours. People are hungry for anything that offers respite from the bleakness of the laments they are helplessly attached to.

A HiPPOs lament is hugely powerful precisely because everybody tends to agree with it out of pragmatism, if not faith, and share in the learned helplessness of their leader.

You’re going to agree with the lament too, and even validate it powerfully, but you’re not going to share in the helplessness. Instead you’ll open an escape hatch.

A good rule of thumb for doing this is: first follow the nerd energy, then follow the money.

If you can nerd out over something, anything, in your own unique way, you can probably open a portal into an energizing alternate dimension that people will want to pay to access. More people will come to you, and say, “shut up and take my money.”

Open up a portal and they will come. Plant a flag and you will die on the hill you built to plant it on.

Create Stage

Finally, once you’ve got good energy going and flowing into the stuck system from your portal, you can begin to create with your clients.

You need clients in the right stage in relation to a complex problem to want to do this.

They’re sick of being stuck. They’re bored of their own lamentations, even if they’re the HiPPO in the picture. They certainly aren’t in a mood to listen to your competing lamentations. They are tired of thinking in terms of disease. They don’t want to hear about malaises and symptoms and root causes and band-aids and other draining imagery that reinforces their sense of helplessness.

They want to feel new streams of agency surging through them.

They want to find a new source of vital energy and inject it into the system, to shake it loose from stuckness.

Your job as an outsider, no matter the specifics of what you offer, is to help dowse for the hidden ley lines of that energy, and then serve as a channel for it through the specific thing you do. Think of it it this way: you only account for 5% of the energy flows you help them tap into. You’re not draining your batteries to charge theirs. You are helping them plug into new renewable energy flows you help them find.

As an outsider you are free to stand in a place from where you can lever a stuck system into being unstuck.

It is that freedom that you are offering to share with your client, by inviting them into the portal you’ve built.

It’s right there in the two-word phrase we use to label ourselves: free agent. You’re free, they’re not. That’s the main source of your value. If you choose to tap into it and share it.

So don’t build a hill for yourself to die on.

Open up a portal for them to walk through.

Going Indie is Going Amateur

Welcome back.

In October, I hit pause, and took around six weeks off from writing this newsletter. It was a much-needed break for me, and gave me an opportunity to reflect, both on the newsletter, and on my consulting practice. During the break, I also turned 46, landing on the “undeniably” side of “middle-aged.” My 10th anniversary as an indie consultant is also coming up. That will be March 1, 2021. Mark your calendars so you remember to please clap.

In a traditional job, I’d be expecting some sort of cheap plaque marking the anniversary, a “personalized” note from the CEO, and perhaps colleagues taking me out for a beer and roasting me. In the free-agent world, nobody would even know if I didn’t tell them. That’s kinda how I prefer it. Which explains why I’ve already lasted twice as long as a free-agent than I did in my only real job (4.5 years).

During my break (unpaid vacation?), I found myself thinking particularly hard about the next ten years. Do I want to continue doing more of the same sort of thing? Will I still be sparring with executives in 2030? Or will I be up to something different? If so, what?

Whatever I do, one thing I already know: I’m going to maintain my amateur status. No matter how long I play the indie game, I’m never going to turn pro at it, whatever that might mean. If you are thinking of going indie, I recommend you think of it as going amateur.

Nearly ten years into the game, I’ve convinced myself that an amateur posture towards work is central to the idea, appeal, and value of free agency. In fact, going free agent is going amateur, even if you were once a professional in some sense.

For a free-agent, being an amateur, as opposed to a professional, is more important than being paid by the gig rather than with a salary.

***

Sherlock Holmes, consultant detective, was technically an amateur in the sleuthing business. Doyle’s creation spawned an entire genre of fiction built around the premise of amateurs beating professionals at their own game, despite the handicap of fewer institutional resources.

A hundred years later, the appeal of the amateur sleuth as a literary invention remains strong. My favorite detective shows in the last couple of decades — Psych, Monk, Castle, and of course, the reimagined Sherlock — all feature amateur free-agent (or in the case of Adrian Monk, failed-professional), protagonists.

The conceit of classic detective fiction as a genre is that the amateur sleuth outwits the criminal, while outdoing the professionals, through an unconventional superior intelligence. But I want to offer you a contrarian take: it is the amateur posture that does most of the work, and looks like inscrutable genius to the professionals when it works out. As such, it is available to anyone with the courage to “go amateur.” Which, I like I said, is almost the same as going indie.

To understand why, you have to first understand the amateur in relation to the professional. After all, there would be no amateurs if there were no professionals to define them through negation.

***

It is easy to construct and tear down a strawman view of professionalism as an artifact of empty credentialism and risk-aversion standing in for credibility, but that would be neither fair nor interesting. Professionalism is a deeper idea, and amateur status only has meaning to the extent professional status has genuine complementary worth.

To be viewed as a professional is enjoy a certain earned dignity in default perceptions; a certain presumption of default value that makes for a great deal of psychological security.

The most subtle part of the security is not the esteem itself, but the certainty of esteem. Within certain institutional contexts, to be a professional is to give yourself permission to suspend your insecurities and let go of imposter syndrome. Nobody will ever wonder why you exist, because under the right conditions, it will be self-evidently obvious why it is good thing that you do. Nobody wonders why Anthony Fauci exists, and most of us in the United States are glad he does.

That’s what it truly means to be a professional. It’s not about credentials, empty or otherwise. Being a professional means you know your worth, and others do too — and not because you brandish your degrees and certifications. To be a professional, in the best sense of the word, is to care genuinely, and try sincerely to do the right thing, and for that to translate automatically into societal value and meaningful validation through the magic of effective institutions.

This is a condition that is worth something both to professionals, and to the society that views them as such. Something that is not to be set aside lightly.

To be an amateur, in the worst sense of the word, is to be an insincere bullshitting dilettante, and for that to result in casual destruction and pain for others.

The last few years have been a battle between professionals in the best sense of the word against both professionals and amateurs in the worst sense of those words.

But what interests me is the missing quadrant: what does it mean to be an amateur in the best sense of the word?

***

What it does not mean is striving mightily to create an ersatz version of the perception of trust enjoyed by professionals. That road leads to cringe personal brands: campy, failed faux-professionalism for free agents based on anxious, over-wrought perception management.

Thar be personal demons, not trusted brands.

No, being an amateur in the best sense of the word means embracing the lack of guarantees as a feature. Amateur status means you represent no guarantees — but people want to work with you anyway because you bring something else to the party. Something the professionals cannot bring, by virtue of being professionals.

When you are an amateur, there is no no guarantee that caring genuinely, and trying sincerely to do the right thing, will automatically lead to anything good anywhere.

It is this lack of automatic, default positive consequences (and expectations of such consequences by others) that leads to the neutral noun amateur turning into the pejorative adjective amateurish. When something is done amateurishly, the best you can usually hope for is “no harm done.” Amateurishness is not lack of skill necessarily. It is lack of predictability in outcomes.

The presumption is that even sincere, caring amateurs are at best inept bunglers who occasionally get lucky. They do not embody any deterministic causal relationship between effort and outcome.

That’s the downside.

The upside of being an amateur is freedom. Freedom from the confining expectations that accompany perceptions as a professional. Freedom from institutionally rigid notions of value. Freedom from the limiting self-perceptions that inevitably accompany ascriptive professional status. Freedom from the conflation of skills and guarantees. Freedom from standing on ceremony. Freedom to wonder and play without a lurking sense that it is undignified for “someone in my position” to do so. Freedom to take strange risks. Freedom to operate with insufficient gravitas (hehe, bet you didn’t think that link would go where it does).

In this freedom, there is certainly the power to destroy. But there is also the power to see and do things that wouldn’t even occur to professionals.

This freedom does not come for free. Merely declaring yourself to be an amateur does not buy you the freedoms of a consciously held amateur posture.

What does it take to earn the freedom of amateur status? What would a non-pejorative sense of amateurish look like?

***

In A Study in Scarlet, Dr. Watson describes Sherlock Holmes’ knowledge as follows:

  • Knowledge of Literature: Nil.

  • Knowledge of Philosophy: Nil.

  • Knowledge of Astronomy: Nil.

  • Knowledge of Politics: Feeble.

  • Knowledge of Botany: Variable. Well up in belladonna, opium, and poisons generally. Knows nothing of practical gardening.

  • Knowledge of Geology: Practical but limited. Tells at a glance different soils from each other. After walks has shown me splashes upon his trousers, and told me by their color and consistency in what part of London he had received them.

  • Knowledge of Chemistry: Profound.

  • Knowledge of Anatomy: Accurate but unsystematic.

  • Knowledge of Sensational Literature: Immense. He appears to know every detail of every horror perpetrated in the century.

  • Plays the violin well.

  • Is an expert singlestick player, boxer, and swordsman.

  • Has a good practical knowledge of British law.

What is notable about Holmes’ knowledge is that though he demonstrably possesses a lot of hard-won, high-value knowledge, to Watson’s eyes, it is unsystematic and idiosyncratic, with what seems like glaring gaps and odd lacunae.

Holmes wouldn’t pass a standardized test except as a side-effect of knowing things his own way (in a episode of Psych, the police detectives Juliet and Lassiter engage in a friendly rivalry over who scored higher in the detective exam — until the amateur protagonist Shawn reveals in a casual aside that he got a perfect score on it as a teenager — which could oddly be read as proof of validity of the test).

Watson’s list says as much about his own status as a true professional twice over — a medical doctor, and an army veteran — as it does about Holmes.

Note that he thinks in categories that sound like a combination of a university course catalog, gentlemanly worldly wisdom, and a finishing school designed to teach polite conversation.

Despite his clear esteem for Holmes, Watson is unable to see a pattern in Holmes’ knowledge. Watson is Seeing Like a State personified.

The only area where Watson dimly senses the gestalt of Holmes’ mastery is one that is not an institutionally recognized subject — “sensational literature.”

Today that sort of knowledge might translate, for instance, to being Very Online and having a vast knowledge of every meme that ever went viral on Twitter. Which actually indicates interesting things if you are not fatally wedded to a professional self-image and institutionally validated patterns of knowing.

In most areas in Watson’s catalog, Holmes is “unsystematic” or “limited” or “practical” (as in, vocationally rather than liberally educated on the topic), and somehow comes up short. In one case — chemistry — Watson characterizes Holmes’ knowledge as “profound,” which is an oddly mystical and exoticizing term to apply in an area where he himself, as a doctor, would be expected to have some expertise.

Note that there is nothing natural or necessary about Watson’s map of knowledge; it is as arbitrary as Borges’ encyclopedia, and arguably no more fundamental than Holmes’ own hidden scheme.

The whole list summarizes Watson’s essential puzzlement over the very essence of Holmes, despite being his admiring lifelong companion and biographer. The charm of Watson as a narrator of the Holmes stories is that he never does figure Holmes out. This is something Holmes himself often points out, in noting that Watson’s accounts of cases invariably miss what Holmes sees as essential, while emphasizing sentimental and romantic aspects he himself is indifferent to.

***

Is Holmes a genius? Or does his amateur status merely present him as such to professionals like Dr. Watson and Inspector Lestrade?

One good definition of genius is: talent hits the target others can’t hit, genius hits the target others can’t see.

Or as Alan Kay once put it, perspective is worth 80 IQ points.

Could it be that Sherlock Holmes is not a genius, but simply a talented amateur whose ways of seeing are inaccessible to the professional eyes of Watson or Lestrade?

Holmes is clearly no insincere dilettante in the stories, so we can eliminate the possibility that he’s the bad kind of amateur. He has accumulated a great deal of knowledge over many years of practice, so his is not a Zen-lucky beginner mind. He is not young, so he cannot be labeled precocious. But his knowledge is not systematic or disciplined, so he’s not a professional.

So having eliminated the impossible, we must conclude, however improbably, that Sherlock Holmes is an amateur, but not amateurish.

He is effective, but his effectiveness comes with no guarantees. He has depths, but his depth-dimensions are invisible to professionals (this is a theme I keep returning to; I first wrote about it almost a decade ago in my ribbonfarm post, The Calculus of Grit).

And it doesn’t matter what kind of professional. Lestrade is a policeman, and in theory should have a better read on Holmes. In practice, he is even more befuddled than Watson.

So it is not the subject matter of expertise that is the problem, it is professionalism as a posture and perspective. Watson and Lestrade both suffer from Seeing Like a Professional syndrome.

The unconventional workings of Holmes’ best-kind-of-amateur mind seem like mysterious but unreliable genius to professional policemen like Lestrade.

For Lestrade, Holmes is something like a magic Deep Learning AI algorithm. Not to be entirely trusted, and full of biases, but someone with unpredictable and sometimes uncanny input-output behaviors. Holmes appears to Lestrade as AlphaGoZero must appear to professional Go players.

So when he gets stuck, despite his confused mix of contempt and awe for Holmes’ methods, Lestrade trudges over to 221B Baker Street, accepts a cup of tea from Mrs. Hudson, sets his professional conceits and insecurities aside, and puts his case to the inscrutable oracle.

***

So I put it to you — Holmes is no genius. He is something better: an amateur in the best sense of the word. As everybody in the stories notes, his silly acts of abductive reasoning are no more than parlor tricks. His apparent genius is actually a lack of the professional blinders and attachment to institutional systematicity — the book in “by the book” — that limits what Lestrade or Watson can see or do.

And this is something all the characters are aware of. So it is not as though Lestrade or Watson are clueless about their professional blinders. They are aware of them, and aware that Holmes represents a way around their own limitations.

We see this, for instance, in the television adaptation of The Abbey Grange, starring Jeremy Brett (probably the portrayal of Holmes that is most true to the original stories). The episode features the following exchange, after Holmes achieves an unconventional resolution of the case:

Sherlock Holmes : It’s almost as though you disapproved of the happiness we have fostered today.

Dr. Watson : Oh, no. I approve of that; of course I do. I am uneasy that you took upon yourself the duties of advocate and judge.

Sherlock Holmes : You are too bound by forms, Watson!

Dr. Watson : Forms are society.

Sherlock Holmes : Hmph.

Dr. Watson : Manners maketh man.

Sherlock Holmes : Hah.

Dr. Watson : It’s just as well you are unique.

There is a resignation in the conclusion that Holmes is “unique.” The professionalism that is leveraged capability for Lestrade and Watson in the right institutional contexts turns into a sort of learned helplessness outside those contexts.

Even when Holmes demonstrates that they need not be helpless, and strenuously asserts “you know my methods,” (implying they are learnable), Watson and Lestrade insist on casting Holmes in the role of a sage with access to esoteric methods forever denied them.

***

It might be a self-congratulatory conceit, but Sherlock Holmes, I would argue, is the model every independent consultant ought to aspire to. Not in the sense of affecting the posture of a genius, but in the sense of ignoring the contours of knowledge held to be self-evidently meaningful and important by professionals, and navigating by your own amateur — but grounded — maps of the territory.

If you keep feeding your insecurities about your lack of a title and clear markers of professional credibility, you’re doing it wrong.

Whether you draw a salary or bill by the hour, the choice to view yourself as a professional is just that. A choice. It just happens to be an easier and more effective choice in more situations.

But it is not the only choice available.

You can always choose to go amateur. The more you know, the more courage it takes.

In a way, you don’t get to experience the essence of independent consulting — consulting as a mercenary calling — unless you go amateur and maintain amateur status.

Amateur status at work, play, and life. There’s just you, the wide-open universe, settling memories of what you have done, animating expectations of what you might do, and no guaranteed expectations for anyone involved.

Going amateur and maintaining amateur status. That’s it. That’s the whole game.

Note to subscribers: Billing, which was paused during my break, will resume starting today.

Heads-up: The annual meeting of the Yak Collective will be held on Thursday December 10th at 8 AM Pacific. It’s a public Zoom event, so do drop by if you’re curious to hear what we’ve been up to and what we are hoping to do next year. Here is the public calendar invite.