261: Making Gut Calls

"You have to trust your gut"

You've heard this advice many times over the years, probably from some successful person on a big stage or talking into a big podcast mic on Youtube.

But here's what they never seem to mention:

Your gut intuition is only built when you actually go with it.

That might seem a little obvious. But consider the implications.

To be able to trust your gut, you have to have experiences where you went with what you thought was right, especially when it conflicted with conventional best practices or the advice of others.

Because if you only ever do what is supposedly the right thing, you never really internalize a mental model for making decisions and building conviction in yourself.

A solo founder client of mine has been trying out potential cofounders.

After a number of founder dating chats, he identified one viable candidate and had been working with him for two months. The first few weeks were great, but over time my client noticed his would-be cofounder took a while to reply to messages, and would push code that had minor but obvious flaws.

His gut was telling him this might not be the right person. Then the doubts came in:

• But that first week had gone so well...
• But we've already met with so many people and he was the best so far...
• But if we break it off we'll have to go back to doing all those coffee chats...
• But his visa situation now depends on being a founder of a US company...

So he hesitated. He tried to give feedback. And then an minor emergency occurred with this potential cofounder that cost the company nontrivial time and money.

Together we talked through the situation and whether my client ought to give the guy one more chance.

"I'm not sure. What would you think of an employee who communicated in this way? Would you want to promote them or give them a raise?"

Still, I emphasized that this was his company and his decision.

But next week when we met he had made the decision to break it off. Immediately a huge weight fell off his shoulders.

"What did you learn from this situation?"

"That I need to trust my gut more. I knew that something was off but I didn't want to be mean or overly harsh about it. But I realized that I was allowed to have high standards in my company and hold people to them."

Cedric of Common Cog talks about this phenomenon of how sometimes getting too much narrow feedback (aka direct guidance) can improve skill acquisition but harm the important skill of sense-making (aka gut intuition)

You may know folks who are smart, and very good at school, who struggle in the world — in messy, unstructured, chaotic domains.

Conversely, you may have noticed folks who are perhaps less smart, that don't do well at school, but yet seem to rack up a track record of effectiveness in a broad span of 'real-world' domains.

This paper gives us a mechanism for why: they simply have better sensemaking skills.

Or, to use the words of businessman and Asian tycoon Robert Kuok, they're better at "distilling wisdom from the air."

The thing is, your gut will sometimes be wrong. It's not a magic genie. And it sucks to bet on your own ideas and fail. But every time it is, you learn something.

If you only follow the conventional playbook and you succeed—awesome.

But you'll never know if that crazy idea that came out of your gut could have been 10x better.

And you won't have any more proof that you should trust your gut next time. Which means you'll only perform at "above average" levels (because you know some people don't even know or can't perform the current best practice).

So don't bet the farm on your initial gut instinct. But try to always follow it when you can. Start small. But keep going.

And one day, a very special opportunity will emerge. And your gut will scream "go for it!" And in that moment, you'll have the clarity and the track record—the conviction—to trust your gut.