In the wilderness

It's tempting to write our own story of an entrepreneurial hero's journey—the truth is more like the Book of Exodus.

Last year, in February, as part of his “Conversations with Tyler” podcast (which is excellent), Tyler Cowen asked Jordan Peterson which ancient myth provides the best guide for today’s modern world. Peterson replied without hesitation that it was the story of the Exodus.

As Peterson had explained earlier in the podcast, the Exodus is about what happens when we are led out of tyranny:

If you’re in a state that’s too tyrannical, you need to escape from it, and that sounds all well and good, that you should escape from the tyrannical conditions that hold you back. That’s fine. So do you escape from the tyrannical conditions and enter the promised land? No, you end up in the desert for 40 years. And it’s a mystery, practically speaking, why it took Moses 40 years to wander through the desert because it wasn’t that big a desert.

Since then, I have not escaped from tyrannical conditions, per se. I was, rather, booted out of a sort of comfortable, useful tyranny. The tyranny of a safe job and a cushy salary and a safe and oh so comfortable established structure. The tyranny of driving through Beltway traffic every morning to take my kids to school and pick them up again. The tyranny of high rent. The tyranny of the known - and, I must acknowledge, entirely of my own making.

My life made sense, and I knew what came next: more of the same.

Being laid off was a shock - a big one. What came next? I didn’t know at the time. As Peterson would say, I was “cast out into horrible, horrible freedom. And that is a desert through which you wander.”

I immediately launched into a job search. What kind of job was I looking for? More of the same. I reached out to my network. I dashed off emails. I leaned into my industriousness, pressing ahead with projects and initiatives on top of regimens and routines.

Six months later, where am I? In the wilderness. Still.

The entrepreneurial hero’s journey

I’m sure you’ve heard this story before, only usually the story goes more like this: I was laid off; I didn’t know what to do; I felt like my life was in crisis; then I searched within myself, I found the answers I had been looking for, and now I’m a successful online consultant with a growing roster of clients that I’m passionate about and a glorious life working from a beach in Thailand. Or Bali. Or take your pick.

This is the entrepreneurial hero’s journey. It comes complete with beginning middle and end. I’ve seen it in Twitter threads and motivational Medium posts. Like all stories, it is invented and invested with meaning by humans. Wherever we are at any given moment in time during the course of our life, we tend to look backwards and form the story of our life in a way that makes sense to us. Wherever we are then, that is the end point - the place where we were meant to be.

I rarely see stories written that only go to the middle: I lost my job, I felt like I was in the wilderness… the end.

And yet, that’s what I am now. I’m in the wilderness wandering somewhere (actually, I’m in Mérida, Mexico working on my Spanish and eating a lot of tacos, but you get the picture). It’s impossible to tell how long I’ll be wandering or how big the wilderness is, but it feels very large indeed. Of course, the wilderness could actually be quite small, and my destination could be right around the next bend. That’s the wisdom of Peterson’s snarky final comment that “it’s a mystery, practically speaking, why it took Moses 40 years to wander through the desert because it wasn’t that big a desert.”

That’s not just Peterson’s humorous afterthought - it’s about how the wilderness is often of our own making.

The desert wasn’t that big and yet it took 40 years to find a way out. Another way to read that: what we perceive to be true about the world around us is often quite far from what is actually true about the world around us, and yet we must move forward.

Things that gain from disorder

In 2012, Nassim Nicholas Taleb published Antifragile: Things That Gain From Disorder. I’ve been reading it all this weekend, and toward the beginning there’s a passage about how we innovate that serves as a nice complement to the wilderness metaphor:

How do we innovate? First, try to get in trouble. I mean serious, but not terminal, trouble. I hold - it is beyond speculation, rather a conviction - that innovation and sophistication spark from initial situations of necessity, in ways that go far beyond the satisfaction of such necessity…

This is ancient wisdom of course, as Taleb points out, and yet it is contradicted by “modern methods and ideas of innovation and progress on many levels.” There are a million books and TED talks and university programs with highly-trained professors dedicated to teaching innovation, but Taleb argues that innovation comes more as a result of conditions on the ground, and certainly not from “experts.” He concludes:

…in spite of the visibility of the counter-evidence, and the wisdom you can pick up free of charge from the ancients (or grandmothers), moderns try today to create inventions from situations of comfort, safety, and predictability instead of accepting the notion that ‘necessity really is the mother of invention.’

Perhaps the problem, then, with my previous attempts at innovation and entrepreneurialism, was that I was operating from a place of comfort and security. I could read a million books on the methods of disruption. I could, and did, read The Innovator’s Dilemma, and many more books on business. I read Peter Thiel’s Zero to One (recommended and not at all political, as Thiel’s current reputation would suggest). Yet I could not truly innovate, Taleb would say, because the necessary conditions in my own life were not present.

Whether they are present now - with no job and no idea about what kind of career might be waiting once I cross the wilderness - is a matter of debate. I have earned myself a kind of comfortable freedom merely as a result of having saved so damn much money. I made hay while sun shone, as the saying goes, and so now I can wander in the wilderness in total comfort, at least for a while.

Midlevel bank employees

Still, I like to think I am capable of the kind of anti-fragility Taleb espouses. In other words, I think I do gain from disorder. As I’ve written, I felt a kind of stagnant professional malaise in my previous job. It was a large, billion-dollar company that had not at all managed to transcend the inevitable bureaucracy which most large companies seem to generate out of nothingness and be unable to escape. That environment stifles naturally entrepreneurially-minded people. I witnessed it in myself and in many co-workers.

Fortunately, writing (in fact, all artistic endeavor) is one of those professions which Taleb points to as having natural properties of antifragility. This is because artists tend to gain from controversy and criticism. There is no bad press. The reputations of artists gain from all kinds of shocks and attention, not just from positive, all-is-well business as usual productivity.

Some jobs and professions are fragile to reputational harm… You do not want to ‘control’ your reputation; you won’t be able to do it by controlling information flow. Instead, focus on altering your exposure, say, by putting yourself in a position impervious to reputational damage. Or even put yourself in a situation to benefit from the antifragility of information. In that sense, a writer is antifragile, but we will see later most modernistic professionals are not.

Taleb recounts an anecdote in which he jokingly threatened to beat up an economist (he rarely has kind words for economists). Sure, he might get a night in jail and a fine, or a highly publicized trial. But what would that do to his book sales? Increase them, of course. Taleb writes:

Now let’s say I were a midlevel executive employee of some corporation listed on the London Stock Exchange, the sort who never takes chances by dressing down, always wearing a suit and tie. What would happen to me if I attack the fragilista? My firing and arrest record would plague me forever. But someone earning close to minimum wage, say, a construction worker or a taxi driver, does not overly depend on his reputation and is free to have his own opinions. He would be merely robust compared to the artist, who is antifragile. A midlevel bank employee with a mortgage would be fragile to the extreme.

All I can say now, as I wander through the wilderness, is this: thank God I have no desire to be a midlevel bank employee. And perhaps more: it sure is nice to be able to string together words into sentences and further into paragraphs and “pieces,” such that I may yet have a future in writing.

But it still feels like wilderness. Even as I sit in an air-conditioned coffee shop in Mérida playing The Cranberries and serving frappes Márago.