Never Miss Twice: A Middle Path to Building Good Habits

Say we’re trying to build a new habit—working out three times a week, for instance. Before long, we’re going to have to answer an important question:

“How strict should I be with myself?”

It’s tempting to take a no-excuses approach: “I just won’t miss workouts.” The problem is, we will miss. Emergencies happen, no-good-very-bad-days happen, and winning streaks can’t last forever. As someone with two kids, I feel qualified to tell you what you already know: life will sometimes get in the way, and it will not ask your opinion first.

The Trap of Endless Optimization

For the last year and a half, I’ve used a program called org-mode to manage my life. It’s a little difficult to explain what org-mode is (and even harder to do it succinctly), but I’ll try.

  • Org-mode is basically a software program within a larger program called Emacs.
  • Org-mode allows you to organize and run your life using nothing but plain text files. You can track to-dos/next actions, take notes, manage projects, create beautiful documents, and do about a bajillion other things---all in future-proof plain text.
  • Org-mode is endlessly flexible and infinitely customizable. You can make it look and behave however you want. And that's kind of the problem.

Optimizing our professional tools (whatever they may be) can feel like a good use of our work time. And it is, to a point—it’s worth making sure our workflow is efficient. But big wins tend to come quickly, and soon we’re scrounging for little increases in efficiency when we’d be better off simply getting to work. Our goal is to produce something valuable, not to create a frictionless productivity system.

On Intentional Communication: Don’t Pick Up the Rope

My wife used to run an after-school program for elementary school kids. She got first-rate training in that job, with most ideas boiled down to a single sentence one could remember when up to one’s eyeballs in third-graders. One such lesson was this:

Don’t pick up the rope.

As in, when a child tries to initiate a power struggle with you, visualize a game of tug-of-war. And don’t pick up your end of the rope.

On Personal Change without Change

Assume your temperament will always be somewhat childish and impatient, and set your rules accordingly.

Tyler Cowen

Many plans for self-improvement rely on the idea of wholesale personality change—that if we work hard enough for long enough, we can overcome a fundamental weakness once and for all.

It’s a romantic idea, and our personalities do indeed change over time. In fact, we tend to underestimate how much we’ll change in the future. We can deliberately improve ourselves, no doubt. But is massive change our best bet for self-improvement?

For Better Performance and an Easier Start, Try a Ritual

teapot and teacupAmong the general population, rituals are underrated.

Professional performers—whose job requires them to do something difficult at a world-class level, at a particular time, and in front of a paying audience—understand the value of rituals.

Some are unremarkable: a concert pianist drinks a particular brand of tea before performing. Others, more memorable: a major league baseball pitcher eats $30 worth of Taco Bell before every start.

The rest of us—who need to perform well on average but don’t need to be absolutely on in a given moment—tend not to bother with rituals.