Learning to Fly by Missing the Ground

Earlier this year, I turned forty.

I’ll give you a moment to choose between “crap I’ve been listening to an out-of-touch old dude who looks younger than he is” and “crap, I’ve been listening to a ponderously self-important kid whose picture I never bothered to look at.”

Forty is an milestone in the middle of the uncanny valley of life. At forty, you’re supposed to be silently suffering the mistakes of the previous generation and making mistakes for the next generation to suffer. It’s a time of life to be shutting the hell up and doing Real Things in short.

Some of my old college friends are doing that. And making obscene amounts of money, collecting titles and stuff.

Failing that, it’s a time to be raising kids by way of apology for not doing Real Things (implicitly hinting that your kids will do Real Things, which seems to involve teaching them to play the piano for some reason that has never been entirely clear to me).

Many more of my old friends are doing that. Clearly, the next generation will not suffer from a lack of piano players.

Forty is not an ideal age to be blogging. Because it’s not an age anyone is particularly eager to hear from. At twenty-five, you’ve got inspiring dreams and ideals to share. At fifty, you’ve got complete stories to tell and lessons to convey.  At forty, if you’re not overworked and too busy to blog, you’re just a distraction for everybody.

As far as I know, none of my old friends is blogging. One is a journalist, but that’s different.

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Crash-Only Thinking

A few weeks ago, I learned about something called crash-only software  (ht, Robert Greco). This is software that has no normal “start” or “stop” mechanisms. It can only be stopped by crashing it. Often this means unplugging the computer physically. It can only be restarted through some sort of failure-recovery routine, with a hard reboot being the most extreme kind. There’s a whole theory of crash-only software design apparently.

The idea of crash-only design  steelmans a strawman idea of mine that has cropped up in multiple recent posts. In  How To Fall Off the WagonI argued that falling-off-the-wagon is the right focal point for understanding self-improvement efforts.   On the Unraveling of Scripts was about why major life transitions are necessarily messy. In The Adjacency FallacyI argued that career transitions necessarily involve a period of anomie caused by status and value disorientation. Crash-only is the more powerful version of all those ideas. From a crash-only perspective, falling off the wagon (and getting back on) isn’t the main thing. It’s the only thing.

A self-improvement system, or a management model for a business, that doesn’t solve for crash-only constraints isn’t a solution, because it will cost more in crash-recovery effort than the value it creates. Transition management of any sort has to be entirely about crash-only mechanisms.

Software ideas of crash-only design don’t port well to human lives and businesses. So how do you port the thinking?

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The Adjacency Fallacy

Lately, I’ve been having quite a few conversations with people who are trying to reinvent themselves for the new economy. The most common pattern is MBA-types trying to reinvent themselves as entrepreneurial types. The second most common pattern is mid-career types who would normally be moving into either middle management roles trying to reinvent themselves as online lifestyle business types.

It took me a few data points to spot the pattern, but I eventually realized that most people navigating such moves don’t get stuck trying to acquire new, relevant skills. That is actually not quite as hard to do as people think. In many cases, you barely need any skills retraining at all. Often you need no new skills at all. You might even be able to drop some skills and get by with a subset of the skills you had to use before.

The sticking point tends to be something I call the adjacency fallacy: the idea that the roles that suit your personality and soft-skill strengths are likely to be socially adjacent to the one you are leaving behind. “Nearby” roles in some sense.  What sense precisely, we’ll get to.

Adjacency thinking works poorly even if you stick to the old economy. Over the years, we’ve seen the metaphor get increasingly complicated: from the “career ladder” to “lateral moves” to Sheryl Sandberg’s  notion of a “career jungle gym.” The last is a concept so byzantine, merely thinking of it exhausts me to the point of wanting to take a nap.

But adjacency thinking does not work at all if you’re navigating a path from old economy to new economy.

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We Have Them Surrounded in Their Tanks

“We have them surrounded in their tanks.”

So spoke Muhammad Saeed al-Sahhaf, the infamous Iraqi Information Minister in the first days of the American invasion. His missives should be an inspiration to public relations personnel everywhere; he was unshakably on-message even as the foundations on which he stood collapsed. His clueless investment in Saddam Hussein’s regime ended swiftly but not poorly (he was reportedly captured and released by the Americans, and is now living in the United Arab Emirates).

Muhammad was a true believer in Saddam Hussein’s Baathist government, and its collapse was inconceivable. In this respect his belief functioned much like that of those apocalypticists whose rapture passes them by, an evaporative cooling effect separating the doubtful from the doubling-down. al-Sahhaf was clueless to be sure, but clueless need not mean unintelligent, nor is the ability to stay on message dependent upon cluelessness.

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How to Fall Off the Wagon

Self-help ideas generally belong to one of three schools of thought, whether the originators realize it or not: values-first, goals-first or process-first. Norman Vincent Peale (Power of Positive Thinking1952), Wayne W. Dyer (Erroneous Zones, 1976) and David Allen (GTD, 2002) are the authors of the pioneering mainstream classics of each sub-genre. Those dates are significant: the schools evolved and matured in that order, each building on the last to some extent.

In the process of exploring the question, “what’s the best way to fall off the wagon in each school?” I accidentally created a visualization that turned out to capture a grand-unified-theory of self-improvement. Well, at least a unification of the parts that interest me personally. I knew triangles would eventually be of actual use in my visualization tool-kit.


Note that self-help types have a tendency to use people and values interchangeably. It is a very revealing conflation that I might explore someday, but for the moment assume that they are the same thing: that people can be reduced to their virtues and vices. They similarly conflate habits and processes, which is also a revealing conflation I might explore some day. In a business/organizational context, goals and values are generally called visions and missions, but that’s irrelevant for this post.

The arrows represent destabilizing forces that act on each of the three schools.  The green triangle of arrows, going clockwise, represents a pattern of falling off the wagon that feels natural to reformers (those who work within a prevailing social order) and wrong to disruptors (those who work from outside). The red triangle of arrows, going anticlockwise, represents a pattern of falling off the wagon that feels natural to disruptors and wrong to reformers. Equivalently, disruptors are exit people (leaving a social order is a primary problem-solving technique), reformers are voice people (driving reform within a social order is a primary problem-solving technique). If you’re not familiar with the exit versus voice model, check out the Wikipedia page.

Hidden in the diagram, there is actually a pragmatic right answer to the question in the title: continuously, and in a circular fashion. The only question that remains is this: clockwise or anticlockwise? Reformers fall around clockwise, disruptors fall around anticlockwise.
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The Physics of Stamp Collecting

Ernest Rutherford’s famous line, “all science is either physics or stamp collecting,” has bothered me ever since I first heard it. I’ve used it to make fun of biologists, and I’ve used it as a critical perspective on physics.

Rutherford almost certainly meant it as an insult to non-physicists, but there is a deeper and non-prejudiced philosophical thought underneath the dichotomy. To get there you have to ask: is there such a thing as a physics of stamp collecting?

I’ve discussed the quote once before, in my extended post on foxes and hedgehogs (short version: foxes are stamp collectors, hedgehogs are faux-physicists), but let’s dig a little deeper.

Turns out, the distinction between sustaining and disruptive variants of deliberate practice, which I discussed last week, is a consequence of the distinction between physics and stamp collecting.

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Saints and Traders: The John Henry Fable Reconsidered

I only recently learned (from Sarah Constantin, whose new blog is worth checking out) of the American folk legend of John Henry, a steel driver who raced against a steam drill and won, only to drop dead right after. Wikipedia tells the story thusly:

He worked as a “steel-driver”—a man tasked with hammering a steel drill into rock to make holes for explosives to blast the rock away. He died during the construction of a tunnel for a railroad. In the legend, John Henry’s prowess as a steel-driver was measured in a race against a steam powered hammer, which he won, only to die in victory with his hammer in his hand and heart giving out from stress. The story of John Henry has been the subject of numerous songs, stories, plays, books and novels.

The amazing thing about John Henry is not that he chose to race against a machine. The amazing thing is not even that he won a Pyrrhic victory. The truly amazing thing is that he was turned into a folk hero rather than a cautionary tale, and a symbol of human dignity when in fact his behavior was what you might call morally robotic: based on non-negotiable values that killed him.

The key word above is prowess. It’s a rather archaic word, one I’ve never heard used in conversation, but a useful one. It has connotations of both skill and valor, bundled together in a notion of dignity. On a level playing field with a closed and bounded set of fixed rules, prowess could also be considered synonymous with competitive drive. 

Unfortunately, a human racing against a steam drill is not exactly a level playing field and the economic activity of building profitable railroads is not exactly a cleanly circumscribed Olympic competitive sport. Asymmetric and open-ended conditions separate prowess from competitive ability and turn it into a liability. A large fraction of the labor force today is in a John Henry situation within protectionist sectors of the economy, so it is important to knock down this particular idol with some unsentimental revisionism.

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A Life with a View

There is a memorable exchange in the Seinfeld episode The Keys, between Kramer and George on the theme of yearning. Unlike much of the show’s humor, which seems dated in the digital era, this little existential joke has improved with age:

Kramer: Do you ever yearn?
George: Yearn? Do I yearn?
Kramer: I yearn.
George: You yearn.
Kramer: Oh, yes. Yes, I yearn. Often, I…I sit…and yearn. Have you yearned?
George: Well, not recently. I craved. I crave all the time, constant craving…but I haven’t yearned.

You can imagine a more poignant version of this conversation over an iPad showing a Facebook feed. The Internet, with its constant parade of lives-that-might-have-been-yours and classmates-not-dated, is a jungle of yearnings. Yearnings that were once confined to fading and static memories of childhood, occasionally awakened by petrichor, now sneak into your life as a steady, colorful stream of living confusion, via windows in present realities. There was no equivalent in the past to being a silent spectator of other lives by default. You either had active, evolving relationships of mutual influence, or mutual invisibility. Like passengers on subways, we only saw people on other routes at stations. There were no relationships of continuous mutual spectatorship.

There was no such thing as a life with a view. 


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Authors and Directors

Sam is a 2014 blogging resident visiting us from his home blog at Moore’s Hand.

I grew up in Michigan, the older of two kids, but the second-oldest of all of my cousins. Every Thanksgiving we would drive to Cleveland for our family gathering, where I would hear about my older cousin Amruta’s exploits, and a couple years later, reproduce them.

She went to Penn; I went to Stanford. She spent a year living in India, I spent two. Post-graduation she started in management consulting; three years later, I followed suit.

Our paths led us both to San Francisco, but while Amruta got a J.D. and became a law associate, I quit my consulting job, taught myself to code, and became a programmer.

If you ask Amruta, she’ll say that the common thread of McKinsey and Big Law has been learning to operate in tough workplace environments. Her one-on-ones at McKinsey gave her detailed personality feedback; she was told point-blank to focus on her assertiveness.

Amruta was receiving training about how to effectively implement ideas in an organizational context — engaging with stakeholders, overcoming opposition, and so on.

My main job perk, on the other hand, is being able to sit on a couch all day and think. I give substantive status reports once or twice a week, as opposed to multiple times a day in consulting.

Amruta is a knowledge worker who primarily implements her ideas in an organizational context. I am a knowledge worker whose ideas primarily execute, and replicate, themselves in browsers and on servers.

We’ll call Amruta’s type Directors and my type Authors.

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Free, as in Agent

A few weeks ago, I rented a spare desk from a small, local company and returned to cubicle-farm land after five feral years in the  wild coffee shops. Two as a virtual employee, three as a free agent. Looking further back, I’ve been writing about virtual and mobile work, lifestyle design and free agency from the earliest days of this blog. My earliest (and most embarrassing) posts on the subject are from October 2007. I was also researching the subject for work and leading a technology project inspired by it at the time. And looking even further back, I was flirting with the ideas and practices at least as far back as 2004.

Strangely though, cubicles feel different to me now that I’ve voluntarily chosen to return to one. Amazing though it might seem, I can actually work in them now. Apparently, I’ve returned to cubicle-dom with superpowers acquired in the wild.

There’s nothing particularly unique about my path though. For the better part of a decade, somewhere between 20 and 40% of working adults in America (depending on how you count) have been doing something similar. Dan Pink’s Free Agent Nationpublished in 2002, is now more than a decade old. And he was calling out a phenomenon that was already nearly a decade old at the time. The book now reads like a history book rather than an account of a contemporary phenomenon.

The transformation is over. We are no longer pioneers establishing a new lifestyle pattern. We are a twenty-year-old demographic, sandwiched between the creatively unemployed and the paycheck class, complete with our own stereotypical behaviors, vanities and delusions.  We just haven’t acquired a Dilbert strip to mirror our lives yet.

So it’s about time we defined free agency on its own terms, rather than as a reaction to, or exile from, the paycheck world.

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