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Optimizing for Learning

by Max

“So, how’s Castle going?”

I get asked this question all the time—by friends, family, acquaintances, strangers, and Tinder dates who Googled me before we met1—and I never know how to answer.

I procrastinated all morning, but a bunch of inbound sales leads came in without my doing any work, so we gained three customers even though I wasted half my day. Good or bad?

An investor told me he’s not interested in our business, but he wants to support us personally, so he’s investing anyway. Good or bad?

We signed some new customers and made some great improvements to the product, but I’m filled with a horrible sense of free-floating anxiety for reasons I don’t understand and can’t explain. Good or bad?

Free-floating anxiety, courtesy of the always-brilliant Garfield Minus Garfield

Most of the time, I can answer the question anyway. I just say “It’s going great.” Or “It’s challenging, but rewarding.” Or, “Everything’s fine, mom, now leave me alone!”

Still, the question begs another: how should we best measure our progress? Yes, we have metrics: new customers, movement on the product roadmap, owner satisfaction. But while those metrics help reveal how the business is going overall, they don’t say as much about how it’s going for me personally.

That’s why lately, my focus has been on optimizing for learning. Whether the tasks I spent my time on succeeded, failed, or hit somewhere in between, my week was a success if I came out knowing a whole lot more than I did when I went in.

Viewing my experiences through the lens of learning changes how I feel about them. Lost a customer? It’s okay, as long as we learned from our mistake. Gained ten customers? Celebrate all you want, but if we don’t know why we closed them, or how we can replicate that success going forward, it’s not much of an accomplishment.

I’ve learned more in 2014 than I have in any other year of my life by far. Here’s hoping—no, planning—to make that rate of learning even higher in 2015.

  1. I swear this actually happened.

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  1. entercastle posted this