The Circuitous Path to Compelling Work

These three interviews, along with many others in the Roadtrip Nation archive, all undermine the notion that you should simply follow your passion, and you’ll immediately be happy. For Glass, Steele, and Merrick, the path was more circuitous. This doesn’t mean, however, that their success is entirely serendipitous. Instead, a pair of related ideas recur in their stories:

  • Don’t expect fireworks on your first day. Glass, for example, talked about the importance of forcing yourself to develop skills when you’re new to a job. “That’s the hardest phase,” he said.

  • Once you’re good — and only then — start looking for your niche. Glass found editing-driven radio programming. Steele found astrobiology. Merrick found surfboard shaping. In all three cases, they were drawing from a deep reservoir of relevant expertise when they made their moves into the work we know them for today. None of them had identified these specific pursuits at an early age. “I had no idea what I was going to do,” said Steele.

This advice is less sexy than the popular notion that with a little self-reflection you can identify your dream job right away. The interviews emphasize instead that the reality of finding compelling work is ambiguous. (Interestingly, even though their archives emphasize this ambiguity, the manifesto page for Roadtrip Nation exclaims, in contradiction to the insights of their own interviews: “It’s up to you to define your road in life based on what you’re truly passionate about.”)

These compelling careers unfold as follows: You choose something. You work hard at building skills. You fail at some things and respond by shifting your attention to other things that work better. Over time, as you become more valuable to the world and confident in your ability, interesting opportunities finally start to arise. It is here, it seems, surprisingly late in the process, that passion reaches full bloom.