It’s been almost two years since I’ve become my own boss, and I am still fairly bad at it. Any real boss would fire me. I take long lunches and don’t come back sometimes. I defer important tasks till the next day because it suddenly seems more important to go get groceries in the middle of the afternoon. It takes me eight hours to do three hours of writing. If you’ve ever emailed me, you may have first-hand experience with my near-glacial correspondence speed.

This is classic severe procrastinator behavior, and as bad as it is, it used to be worse. But I’m improving only about as quickly as a guitar player who takes six days off a week.

Not all areas of my life are as inefficient as my desk work though. When it comes to fitness I have become the opposite. For more than a year now I’ve been on top of my fitness programs, with no interruptions or start-overs. In the gym, I get my work done, with no compromises and no wasted time. I make real progress consistently and feel awesome about it.

I was talking this through with a fellow self-employee the other day, and wondered aloud, “Why can’t I be as good at my work-work as I am at my gym-work?”

Since then, this question—why does X go so well and Y so badly?—has become fascinating to me. Clearly something is seriously different about the way I approach each, the way I perceive the work.

You probably have a different X and Y than I do, but with a similar disparity in success at doing them. What part of your life do you handle well? What part are you perpetually botching?

It doesn’t seem like a comparison between lifting and working habits would yield any insights. Pressing a barbell over your head is nothing like outlining a book. But on a fundamental level, the two operations are the same: I have a list of stuff to do. At the gym I do it all. At my desk I don’t.

So I sat at the table with a cup of coffee and broke it all down. Why do I lift better than I work? Lots of reasons. Here are a few.  Read More

Time travel is just like regular travel, except you move around the fourth dimension instead of just the other three. I will explain how. It doesn’t take any special talent but you do need to practice it. You can do it anywhere, even when you’re regular-traveling.

The first thing you should do when you get to a new city, I remember reading in a travel guide, is find the highest point where you can see the whole thing. Before any other sightseeing, you’re supposed to get yourself up to the observation deck at the CN Tower, Christ the Redeemer, Top of the Rock or the Space Needle, and look at the city from there.

The writer claimed this ritual totally transforms a visitor’s experience of a city, because everywhere you go afterwards, you know roughly where you are in the landscape. Otherwise, knowing where you are is a completely abstract exercise. You’re picturing yourself on the map instead of in the territory, navigating colored lines and rows of rectangles instead of the actual streets, hills, waterways and boroughs that make up a real-life city.

This sounded like a great idea and I planned to do it in every city on my big backpacking trip. But I forgot to actually do it until years later in New York, near the end of my trip. I went to the top of 30 Rock and saw the city for what was, I realized, the first time. I took about 500 pictures, but none of them really capture the sense that the city is a great big physical thing, a surreal carpet of buildings growing over what was once probably a very quiet natural harbor.  Read More

Dear 15-year-old self,

The first thing to know is that high school, and everything that comes after it, is impossible to get right. When you’re a kid you don’t have to be anything except what you are, a kid. But when you’re an adult, or training to be one, all aspects of life seem to become concerned with trying to be a certain way: sufficiently cool, successful, independent, respectable, charitable, productive, original, normal, healthy, sexy, or whatever else you currently are not. This impossible goal is the great joke of human life that I will try to explain in this letter.

In high school, this mostly means one thing: don’t try to be cool. You will not be cool until your late twenties. It isn’t actually possible to be cool in high school—all high school students are hopelessly uncool, especially the cool ones. This will be obvious the moment you graduate, but in the meantime you might have to make a point of remembering it.

None of the respect you earn in high school will buy you anything after you leave high school. It’s like working at Canadian Tire for a summer and getting paid only in Canadian Tire money. Waste no energy earning respect in high school. Spend it instead wandering every sidestreet of geekdom and subculture you pass by. Instead of finding scraps of approval from uncool people, you will end up finding something real and lasting in Brian Eno or Nietzsche or Margaret Atwood or Public Radio. Find those grooves of meaning that you can follow into adulthood. When people give you a hard time for liking what you like, that’s a sign you’re on the right track. You are uncovering veins of precious metals; they are scrounging for nearly-expired coupons.

Get a shitty job. Work in a grocery store, steering shrink-wrapped pallets of cola through cramped warehouses. Spend hours daintily arranging shelves that you will later see customers destroy in minutes. This will pay for your food court lunches and headphones, and also impress on you the nihilistic reality of most of the work out there. Get a good, long, nasty look at how impersonal and irrelevant your role on this earth can be if you’re not careful. Get your face right into it, right into the filthy shelves and bins of expired yogurt and the empty eyes of your manager and make a vow that whatever you do with your life you will always be moving away from all of that.  Read More