Be Ambitious

You may not know this, but I took a pay cut and moved my family to mid-Missouri from Washington, DC, to work for Permanent Equity. By any standard measure of success, that wasn’t a good career move. In fact, more than one person thought I was crazy. But I did it because I was pretty sure it was a great career move. I believed in myself, I believed in the organization, and I believed in what I might bring to the organization and what the organization might bring out of me. 

People ask me, “How’s it going?” My answer? “Better than expected.”

Our friend David Perell recently wrote this about ambition: “Ambition isn't about climbing the career ladder faster than your peers — no, that's complacency. An inability to think for yourself. True ambition comes from conviction and the courage to see a grand vision through to completion.”

Before I say what I’m going to say I’m going to say this: Success is not a base state. Things are hard, and I begrudge no one for working hard to make linear progression.

But!

Linear progression is not interesting. It’s satisfying, but not interesting. What’s interesting is variance.

And look, I don’t have a grand vision; I just don’t want to be bored. I think of myself as being in the business of creating upside, both personally and professionally. The catch-22 of that is that the optionality of upside comes with the risk of downside. There’s a world where I got out here and Brent and I didn’t get along and I ended up jobless in Rocheport living in a van down by the river. Thankfully, that didn’t happen or at least hasn’t happened yet. And I think this is also more nuanced than Jeff Bezos’ regret minimization framework.

See, it’s not about doing things you might regret not doing. Rather, it’s about not doing things you wouldn’t regret doing. 

We would have been fine in D.C. And the reason that’s sad is because we wouldn’t have known the difference between what we did and what we might have done.

Along the same lines, I had an interesting conversation with an entrepreneur we know who has ended up being quite wealthy. He took me aside at dinner and said, “Hey, I want you to know that I will never invest with you guys.”

I said, “Oh, why is that?”

He said, “I think what y’all are trying to do is great, but if I am going to give my money to other people then it means that I am out my own ideas, and I have plenty of ideas.”

On the one hand, I thought, “Hell yeah!” On the other hand, I thought, “That’s not a thoughtful approach to diversification.” But as David said, “True ambition comes from conviction and the courage to see a grand vision through to completion.”

We’ve offered people jobs and been turned down because someone didn’t want to move to Missouri or because the base salary we were offering wasn’t high enough. We’ve thought about going back to these people with different offers, but never did. Or at least never really did.

The reason? We’re ambitious. And I think that’s ok.

– By Tim Hanson


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