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Off The Record
Betting on yourself

Betting on yourself

Why finding the right place for your unique superpower can help you achieve outlier-level success

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Alex Su
Nov 24, 2023
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Off The Record
Betting on yourself
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Many of us suppress our true career aspirations because we’re afraid of financial instability and loss of prestige. Even though we’ve got strong hunches about the type of work we’d be great at, we soldier on in unfulfilling jobs in the corporate world. At some point though, we face a fork in the road where we’re forced to make a decision. We can either (1) go along the conventional path or (2) do something different that better aligns with our talents, ie. betting on yourself.

Betting on yourself involves doing something that feels risky, but is aligned with what you know about yourself deep down inside. By the time you’re mid-career, you probably have a pretty good idea of what your superpower is. Yet you probably have been ignoring it, because you’re following an approved career path that’s supposed to pay off someday. Betting on yourself involves walking away from that certainty, and following your instincts about where you belong. Very often it involves short term pain, because the new opportunity pays a lot less.

I’m not going to sugarcoat it. It’ll feel pretty scary. Especially since at first, you’ll be generating less economic value. You’re essentially going into uncharted territory as a highly talented generalist. As a result, you will no longer be plugged into a highly lucrative economic engine (e.g.. Biglaw, BigCo, or some other large bureaucratic organization) but be out on your own, alone, trying to figure things out.

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