Two kinds of practice

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The first is quite common. Learn to play the notes as written. Move asymptotically toward perfection. Practice your technique and your process to get yourself ever more skilled at doing it (whatever ‘it’ is) to spec. This is the practice of grand slalom, of arithmetic, of learning your lines or c++.

The other kind of practice is more valuable but far more rare. This is the practice of failure. Of trying on one point of view after another until you find one that works. Of creating original work that doesn’t succeed until it does. Of writing, oration and higher-level math in search of an elusive outcome, even a truth, one that might not even be there.

We become original through practice.

We’ve seduced ourselves into believing that this sort of breakthrough springs fully formed. What always happens (as you can discover by looking at the early work of anyone you admire), is that she practiced her way into it.

How to have your Better instincts….

“Go with your gut,” is occasionally good advice.

More often, though, it’s an invitation to indulge in your fear or to avoid the hard work of understanding the nuance around us.

Better advice is, “invest in making your gut smarter.”

The world is a lot more complex than our gut is likely to comprehend, at least without training. Train your gut, get better instincts.

How do this?

Practice going with your instincts in private. Every day, make a judgment call. Make ten. Make predictions about what’s going to happen next, who’s got a hit, what designs are going to resonate, which videos will go viral, which hires are going to work out. Write them down or they don’t count. It makes no sense to refuse to practice your instinct and to only use it when the stakes are high.
Expose yourself to more deal flow. If you want to have better instincts about retail, go work in a retail shop. Then another one. Then a third one. If you want to have better instincts about hiring, sit in with the HR folks or volunteer to help a non-profit you care about do screening of incoming resumes.
Figure out how to talk about your instincts so that they’re no longer instincts. A thinking process shared is inevitably going to get more rigorous. Ask your colleagues to return the favor, by challenging each other to expose their thinking as well.