Shadow careers

08 Aug 2022

Steven Pressfield’s idea of “Shadow Careers” has influenced every career decision I’ve made since I first came across it as a college student.

The actual text only takes a minute to read, so I won’t bother paraphrasing, just go read it here.

As soon as I learned of the shadow career, I began to see the immense gravity it imposed all around me. Shadow careers especially ensnare fresh grads from competitive universities because they carry, at least superficially, high status, high optionality,¹ and low risk.²

In giving a name to the failure mode I had only vaguely sensed up to that point, Pressfield clarified for me why certain career paths can seem so enticing, yet so hollow. Pursuing a shadow career is as unsatisfying as running an unfalsifiable science experiment. In exchange for the impossibility of "failure," you lock yourself into living the deferred life plan.

When I think of shadow careers, I think of professional critics. Being a film or food critic takes work, for sure, but it’s a hell of a lot easier than making a film or running a restaurant. Whenever I find myself on the side of the critic, I know it’s time to reassess the decisions, beliefs, and external influences that led me there.

In the world of startups, the shadow career that gobbles up the most ambitious talent, by far, is venture capital. VCs appear on the same podcasts, attend the same parties, and are congratulated on exits / IPOs in much the same way as company builders. As Pressfield puts it, “its contours feel tantalisingly the same” as building and growing companies. While that might be what attracts many young people towards the profession, I believe that’s also its biggest danger.

Here’s a useful reminder for us all — The shadow career runs in parallel with your true calling. However small the gap in between the two, they’ll never intersect.