A Riff on the “When-Then Trap”

Last week, Khe Hy wrote succinctly about the dangers of the “when-then trap.”

We’ve all been there:

When I have X dollars, then I’ll be happy.

When it’s less busy, then I’ll hit the gym.

And and old bugaboo of mine:

When my work is totally on track, then I’ll make time for life.

Of course, at $X, we want $X+Y. It never gets less busy. The more on-track work looks, the further down the track I’m determined to drive.

Even though the premise is obviously flawed — the purpose of moving ahead is more motion, not stasis — this trap is extremely difficult to avoid. After a strong start to the season on my old skis, I’m mostly fantasizing about what kind of skier I’ll be on new boards.

Reflecting on this trap, I finally made the connection to my journey out of school. After spending the majority of my first three decades being good at school, it’s easy to see all the when-thens I accepted: when I get to college, then I can be me. When I get a little professional experience, then I can get a master’s. When I get another degree, then …

The point isn’t that school is the only or even the primary source of this myth. Rather, it’s that this myth comes from somewhere, and it makes sense that such a widely shared idea is something we’re exposed to from an early age.

This year, I’m planning to double down on turning pro rather than getting another degree. But, in the spirit of Steve Pressfield, here’s a little note to self:

The purpose of turning pro is to turn ever more professional, not to simply transfer the when-then fallacy from school to work.