310: Shadow Careers and Unembracing Failure

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​Happy Monday!

Last week my article on STEPN, the new "Move to Earn" game on mobile kinda blew up so you might wanna check that out if you're interested in crypto gaming.

And that's about it. On to the Medley!

Shadow Careers & Unembracing Failure

In “Turning Pro,” Steven Pressfield lays out how one goes from amateur to professional:

“The amateur fears that if he turns pro and lives out his calling, he will have to live up to who he really is and what he is truly capable of… In his heart, the amateur knows he's hiding. He knows he was meant for better things. He knows he has turned away from his higher nature.”

One of the common habits of an amateur, according to Pressfield, is living out a shadow career:

“Sometimes, when we're terrified of embracing our true calling, we'll pursue a shadow calling instead. That shadow career is a metaphor for our real career. Its shape is similar, its contours feel tantalizingly the same. But a shadow career entails no real risk. If we fail at a shadow career, the consequences are meaningless to us.”

The shadow career metaphor shines light on a trap we can fall into with our work: Doing what’s easy, expedient, or expected, instead of what feels authentic. Instead of our “true calling.”

Pressfield explains we can tell we’re in a shadow career because the consequences are meaningless. The choice of word “meaningless” here is important. It doesn’t suggest you wouldn’t be financially stressed if you fail, or that you wouldn’t be embarrassed. It’s how you would feel on an emotional level. Would you personally feel like a failure if this failed?

For a long time, I thought it was weak to be vulnerable to someone. That you should be emotionally self-sufficient, such that losing someone couldn’t really harm you. I eventually realized that love, like many things, cannot exist without its opposite. If you aren’t willing to be devastated by a loss, you cannot enjoy a gain. Light and dark. North and South. Any pole necessitates some of its opposite.

In the entrepreneurship world, there’s a common sentiment of “embracing failure.” It’s Silicon Valley scripture that you need to become deeply comfortable with failure to build anything of substance. Failure is to be celebrated as part of your education on the yellow brick road to a Patagonia vest and A16Z partnership.

I get the intention, but that’s also kinda loser talk. Why would you celebrate failure? You FAILED, loser. I get that you learned something, sure, but it would have been a lot better to learn something and succeed.

The obsession with embracing failure gives you psychological permission to pursue a shadow career. When you train yourself to treat the downsides as low stakes, you will be pulled in directions that allow for low stakes failures.

But we should want to work on things where failing terrifies us. If you feel nothing when a relationship ends, why were you in it in the first place? If you wouldn’t be devastated by failing to succeed at your mission, what kind of mission are you spending your limited years pursuing?

It’s a bit lofty, sure, but it provides a useful heuristic. Assuming your basic needs are met it might not be worth working on anything where you aren’t terrified of failing. If you know a project is going to succeed, or you’d be fine if it failed, then it’s not a true calling for you.

There’s a concept I think about from time to time, that hell would be meeting the person you could have been. Who you could be if you ignored the shadow careers, the side quests, the failures you were okay with.

Imagining that person can often be helpful. You’ll almost immediately fill in certain gaps, probably related to what you’re most insecure about. What would you expect them to say they did? What would they tell you they accomplished that would make you immediately overcome with self-loathing at your own shortcomings?

I know my answers, and I bet you do too. It’s not fun to think about, but it is certainly useful. Most of us are in shadow careers. Shadow careers are the defaults. We have to spend some time imagining that person, seeing what they could say that would make us the most embarrassed, to start to tap into a potential level of fulfillment we’re passing up for what’s easy.

“What happens when we turn pro is, we finally listen to that still, small voice inside our heads. At last, we find the courage to identify the secret dream or love or bliss that we have known all along was our passion, our calling, our destiny.”

And lest it gets confused, achieving these secret dreams won’t bring any lasting happiness. Finding the right challenge to struggle against, though… that’s a game you can play for life.

Have a great week,

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