Six Rules That Guide Me

I am always tinkering with my lifestyle in hopes of minimizing my mistakes, anxiety, distraction, and discontent. What follows is a personal code of sorts, a collection of others’ wisdom that I try (and often fail) to incorporate in my daily life. I’ve discovered that when something goes wrong, there’s an 85% chance that I’ve broken one of these rules:

1. Prioritize your personal energy

You cannot take care of others until you’ve first taken care of yourself.1 Lack of sleep, strength, flexibility, or calories is a lack of self-respect.2 Impose a schedule on the world or have one imposed upon you. Have faith in others to solve their own problems.

2. Focus on what is under your control

If you can’t control whether you win or lose, you can control how you lose. (Don’t run after buses.)3 Under your control: process, habits, grit, temper, narrative, and exposure to luck. Remember that “virtue, magic, and beauty [are] more important than the trophy case.”4 Don’t take success personally.5

3. Be barbelled

Maintain a 90/10 safety to speculation ratio in investments, art, and life. Your risk of ruin must always be nil. Seek out convexity, but don’t overpay. “Paranoia + aggression = antifragility.”6

4. Say “No,” and impose constraints

“Innovation is saying no to 1000 things.”7 Decline to compete with others. Limit your decisions. Creativity is born of constraint,8 freedom of habit and routine.

5. Privilege actions over speech, control over power, and payoffs over knowledge

More important than what others say is how they behave. Heed Ferguson’s philosophy: “Power is throwing your weight around. Control is making sure things go your way regardless.”9 Ask yourself, “So what?”10

6. Be patient

“Beauty is patience.”11 Beware of “perfectionism in a hurry.” It is your nature to fret, tinker, and experiment.12 Speak less, listen more. Practice the sacred pause.13 Remember that “everything changes, nothing perishes.”14

I do not claim such rules are universally applicable. For instance, few people seem to find eating to be the same intolerable chore that I do, and so probably have no need to cue themselves to consume more calories. Some people may be able to say no to others with such facility that a rule about saying yes may be more relevant to their lives. These rules are only what works for me.

Notes From the Wise:

1. The “energy metric” is recommended by Scott Adams in How to Fail at Almost Everything and Still Win Big: Kind of the Story of my Life.
2. I have adapted this from the wise advice of Maria Popova regarding sleep: “We tend to wear our ability to get by on little sleep as some sort of badge of honor that validates our work ethic. But what it really is is a profound failure of self-respect and of priorities.”
3. Adapted from N.N. Taleb’s advice in Antifragile (“Don’t run after trains”). In general, Taleb’s Incerto series is probably the most impactful work I’ve read with respect to how I live and think about the world.  
4. Corley Miller’s gorgeous summary of Arsène Wenger’s football philosophy
5. The chief lesson of Jim Paul and Brendan Moynihan’s What I Learned Losing a Million Dollars. (Recommended by Taleb.)
6. Paraphrased from N.N. Taleb’s Antifragile.  
7. Steve Jobs, Apple Worldwide Developers’ Conference, 1997. 
8. The wisdom of Jack White, in a nutshell. See, for example, It Might Get Loud, or search YouTube for Jack White and creativity.  
9. David Runciman’s summary of Sir Alex Ferguson’s managerial style
10. The Great Question posed to me, time and time again, by my 11th grade history teacher, Mr. Woods, which has stuck with me for my entire life. There’s an obvious parallel with Taleb’s focus on payoffs over knowledge. 
11. Luis Cernuda, “Lázaro.”  
12. From Malcolm Gladwell’s podcast, Revisionist History,  the “Hallelujah” episode. The episode references David Galenson’s work on creativity.
13. From Tara Brach’s Radical Acceptance. Excerpt
14. Ovid, Metamorphosis

Mistakes I’ve Made

“…he did seem to carry around a history of defeat, of troubles borne and lessons learned. He had an air too of gallant accommodation towards whatever choices had gone wrong or chances hadn’t panned out.” —Alice Munro, “Family Furnishings”

Show me that man who will own his mistakes, and not his successes, and I will call him a friend. Here, in painful detail, are a few of my own:

Why I Am So Blind

I was born in 1979, and so caught between two generations and their illusions. Because I am not quite a Millennial, I did not grow up with computers. I was 16 before my family owned a Windows 95 machine, and I learned to type in high school on an electric typewriter. As a boy, when I would leave the house, my father would always remind me to “bring a quarter” in case I needed to find a payphone to call him.

When I was 10, I was mesmerized by the technology of Star Trek: The Next Generation, from the as yet unrealized transporters and replicators to the approaching realities of tricorders and artificial intelligence. Merely 25 years have passed, and my laptop is already thinner than Captain Picard’s.

Among my great mistakes is that I did not see the exponential progress in technology happening right before my eyes. Indeed, it was not until the first release of the iPhone that I was shaken from the nightmare of scarcity that so shapes Gen X’s view of the world. All of a sudden, I could, for practical purposes, own a device I had dreamed of having since I was 10.

This may seem a trivial observational error, but for me it carried existential and political consequences. To understand why, it is worth quoting at length an interview between Derek Matravers and G.A. Cohen1:

MATRAVERS: A couple of aspects of Marx’s thought that you touched on there do seem implausible, at least when you first come across them: that communism will be a period of great abundance, there won’t be any scarcity, and secondly, that people’s characters will be such that they will work for the common good and interact in some kind of true community. Do you think there’s anything that can be said to make those two presuppositions of communism seem more plausible, or do you think they’re just hopeless?

COHEN: Well, I don’t think they’re as independent as you might think, when you say there are these two presuppositions. Because if you really think through what I think he intended by abundance, which was something enormous, absolutely amazing, where you could just take anything you want from the common store, then, the human nature premise is very weak. It just says people aren’t going to be ordinary and needlessly destructive. It doesn’t ask them to sacrifice anything. I mean, I’m saying the abundance premise is so extravagant that the second premise can be taken on board because the extent to which people need to work for the common good in circumstances like that is very modest.


But the abundance premise is ecologically puerile. I mean, it’s clear that unless somebody invents something we don’t know about yet, like a so-called fusion gun that operates directly to change the sub-molecular structure of matter so that you could turn, you know, camel dung into tiramisu. Failing a technological breakthrough that might come, the premise of abundance is just absurd. I mean, it contradicts everything we know about the limits there are on the planet earth. And therefore, Marxists can’t rely on it the way they did through the tradition. So I’m saying, it’s not that we’re saddled with two difficult premises; we’re saddled with a choice with respect to what would make communism possible. And much more than before, we have to go for the human nature facilitation rather than the abundance facilitation.

Cohen’s interpretation of Marx above seems to me to be correct. Previously, like Cohen, I considered the abundance premise to be absurd. (Unlike Cohen, I was even less optimistic as to the malleability of the human character.) The iPhone changed that because however imperfect the original, I could see what it might evolve into and I better understood how quickly that could happen. And if today I nearly have a tricorder, why not nearly a replicator or a fusion gun tomorrow?

Moreover, if the technological constraints I previously took for granted were not realities but ideological illusions, might not my pessimistic view of human “nature” have been yet another mirage?

Why I Am So Sorry

In grad school, I had the luckiest experience of my life: I flunked a statistics test (to such an extent that I wasn’t quite sure what half the questions were asking), suffered an anxiety attack, and left school, leaving behind a not ungenerous amount of funding.

I took some time to focus on my health and on my writing, and in the process worked a variety of jobs as an editor, an English teacher, a server, a porter, a cleaner, a postal clerk, and a caregiver to name a few. Subconsciously, I suppose, I took Harlan Ellison’s sage advice: “If you want to really write, what you should do is you should get yourself an honest job; not one of these, ‘I’m a computer designer’ or ‘I’m a systems analyst’—oh, bullshit!”2

What honest employment taught me—for I think that at least a few of my jobs have been honest—is that class deeply matters. So too does power. I saw the best minds of my generation destroyed by menial work—scraping gum out of the carpet after posh corporate dinners, for instance. I had a front row seat to the hollowing out of the middle class and the evisceration of the vulnerable.

bullI saw too the insulation of the elite and the W.E.I.R.D.,3 and I saw it on an international scale. I spent months commuting each day from S.M.P. to San Isidro, teaching the rich yet being fed by the poor. A remark of one of my students has stuck with me. When I asked him how long it took him to prepare the elaborate lunches he would bring to work, he stared at me in bewilderment. His maid made them, he told me, as a man might patiently explain to a child that the sum of two and three is five. “Everyone has maids in Perú.”

If you think that same level of insulation does not prevail amidst Canada’s upper class, well, friend, you know neither them, nor likely, yourself. “Oh, yeah? Well, how do you know them so well?” Because I went to school with them. Because their illusions were, to some extent, my own. And because I’ve served their dinners and cleaned their carpets with people far better than myself, people whose fates were determined not by their merits, but by want of resources, connections, sociopathy, and luck.

Why I Am So Neurotic

As a young man, I failed to follow my instincts and took too much to heart the advice, opinions, and influence of the Baby Boomers. (I exclude here my parents, and speak in general.) Indeed, I have never overcome the anxiety of the Boomers’ influence. The advice that generation received from their parents was generally sound: “Get a degree, any degree, and you’ve got it made.” And so that advice was amplified and passed down to us with, at best, underwhelming results.

I cannot say I regret my business degree, exactly, because I met almost all of my dearest and closest friends at university. I chanced upon a few spectacular professors who made important personal impacts on my life. But the piece of paper itself, and the importance I attached to it, was a mistake that set me back immeasurably as an artist.

Far from improving me, my education from K-12 to university made me a worse thinker, a less moral person, and a psychologically frail human being. It wrecked my faith and self-confidence, and taught me to overthink and to second guess my every instinct.

feelingsI by no means think that a university education is inherently detrimental. I say only that, on the whole, it was detrimental to me. What I needed most at 19 was simply to take photographs, to work with my hands, and to be engaged in activity that induced a psychological state of flow. Moreover, I needed to learn how to love, to pray, to fight, to forgive, to choose, and to laugh at myself. The last thing I needed to learn was how to think any more “critically.”

In the end, it took me a torturous decade to earn a bachelor’s degree. Even when I was not in school I was stuck there psychologically. I would have recurring dreams of having been absent from a math class for an entire semester and having to write the final exam cold in order to pass. Could any nightmare possibly be more trivial, ridiculous, or unfrightening?

The nights are long, and I’ve had the time to revisit, rethink, reverse, and regret every decision I’ve ever made. Rarely was there a “correct” or “most correct” choice, as my years of diligent test-taking taught me. In almost every case, however, the most fulfilling and personally enriching choice was my first instinct. But I seldom had the courage to follow it, or if I did, to stick to it.

Why I Speak So Seldom

How much confusion I might have saved myself had I studied Wittgenstein earlier! Like many young people, I longed for a sense of certainty through my 20’s: I wanted words to have clear meanings, for concepts to have sharp edges, and for right and wrong to be so mathematically precise that it was impossible to step astray, except by nefarious choice.

I will always love Plato’s definition of love: “Love is wanting to possess the good forever.”4 In my salad days, I longed for love and permanence to such an extent that it ultimately detached me from the world. (It also led me to serious errors of judgement.)

“Don’t think, but look!”5 Wittgenstein’s exhortation was a blow to the chest that knocked the wind out of me for years. His approach to language, philosophy, and life humbled me so profoundly that I have never quite recovered. I looked at the work I had produced, the book I had written, and the path I was pursuing, and I was ashamed. All were hopelessly inadequate, foundationally unsound, and flawed beyond repair.


A diagram illustrating only my hopeless confusion about language and epistemology.

Wrote Wittgenstein, “We are unable clearly to circumscribe the concepts we use; not because we don’t know their real definition, but because there is no real ‘definition’ to them”6: that is not a statement of relativism, but a great victory for common sense. Morality is not like math; nor incidentally, is math like math, for the curious, ultra-Platonic view I once took of it.

Wittgenstein freed me from the chains of philosophy and pushed me back into the embrace of the passions. Together with Kierkegaard, he taught me the great importance of instinct, feeling, emotion, mood, and faith. Plato had it backwards: philosophy leads us into the cave, not out of it.

Why I Am So Uncivilized

Perhaps my most embarrassing mistake is that I once thought that what I believed derived directly from reason, that I had thought through matters of morality and politics and come to my own a priori conclusions, much like Ivan Karamazov.

I failed to recognize the deep influence of Christianity, social class, and English Canadian culture on my thinking, to cite but a few. The genetic predisposition of my personality I never fully considered. I might as well have conceived of myself as a brain in a jar. Visions of “freedom” preoccupied me enormously. I had not yet felt “the weight of too much liberty.”7

Having lived with different families belonging to different cultures, I’m now much more interested and aware of the subtle influences and tensions often present in my judgments. Culture is a messy concept which I leave to the concern of the anthropologists. But, to my peers who insist that “we don’t have a culture,” I would ask, first, “Who then is we?” and second, whether that sentiment itself might not be a kind of meta-cultural confusion.

Spend some time being the outsider,—and so called—having your illusions (politely) pointed out to you on a consistent basis, and you might be forced to concede that you are not a brain in a jar after all. For me, that was a liberating insight: It meant that every decision did not have to be made in the vacuum of reason, ad hoc and on spot, stripped of tradition and context. It made me less apologetic and more introspective about where I come from and why I see the world the way I do.

In Short

Here is a brief list of lessons I had to learn the hard way:

1. Marx was right about technology
2. Class matters, and so does power
3a. Don’t discount your instincts
3b. Not everyone should go to university
4. “Don’t think, but look!”
5. Culture matters, yours too


1. “Derek Matravers and Gerry Cohen on The German Ideology.” Podcast by the Open University, published 22/8/2009
2. Stanley Wiater interview with Harlan Ellison. Dark Dreamers (tv), 2000.  
3. i.e. “white, educated, industrialized, rich, and democratic.” 
4. Symposium 206a, Alexander Nehamas and Paul Woodruff translation. Plato: The Complete Works. Hackett Publishing, 1997. 
5. Philosophical Investigations (66), G.E.M. Anscombe translation. Blackwell Publishing, 2008. 
6. The Blue Book (25).  
7. Wordsworth, “Nuns Fret Not…”