Looking Within

“True self-awareness remains in short supply. When I mentor on career, the first question I ask is what are you optimizing for? Ends up being a difficult question to answer, with folks looking to me for what they should be optimizing for. But only looking within can answer that.”
— Sachin Rekhi, Twitter
This essay was originally published as the introduction to Good Work—Edition Nº 4 on Holloway.com.
Everything is Free by Gillian Welch

Answers to what we’re optimizing for can be troublesome. They’re often not even the real answers. “I want to move to New York City” can really mean, “I want to work with people who challenge me to think in new ways.” “I want to start a company” can really mean, “I don’t want to work for my boss anymore.”

In their book, Designing Your Life, Bill Burnett and Dave Evans talk about the importance of finding your “north star.” The phrase is a bit too Disney for me, but I like the distinction that a north star is something you optimize for over decades whereas goals are stepping stones towards your north star. We’re never optimizing for one thing, and these layers of wants, goals, and north stars interact with each other. Knowing what we’re optimizing for can be the real challenge, and the most rewarding one to figure out.

It might feel like a lot of work to look within, to ask uncomfortable questions, to find habits that keep you tuned in to what’s important to you, but if we don’t look within, we’re likely to find ourselves bouncing around the world like a pinball hoping not to fall into the gutter. Whether you’re starting a team, joining a team, or hiring onto a team, knowing what you’re optimizing for will help you determine whether an opportunity is a fit or not, possibly saving you months or even years of time spent working on the wrong thing.

So how do you figure any of this out? In the next two editions of Good Work, we’ll share thoughts, ideas, and frameworks. Stay tuned.

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