👋 Hey, it’s Wes. Welcome to my weekly newsletter where I share insights for high-performers in tech, based on 15+ years as a marketer, operator, and a16z-backed founder.

I originally published a version of this essay in March 2019. Enjoy.

Read time: 3 minutes

One day, Seth Godin was making lunch for the altMBA HQ team in Hastings-on-Hudson, New York. Guess what was on the menu?

Scallops. I’ve hated scallops since I was a kid.

I said, “That looks great! I'm not a huge fan of scallops. I'll pass, but thank you.”

I've responded that way dozens of times over the years. It was habitual at that point to say no to scallops.

He said, “Really? Give them a try. They're fresh caught from a boutique grocer in Chelsea Market and they are delicious. Just cut a tiny piece and see if you like it. If you don't, I’m sure Alex or Willie will eat it.”

The scallops were right there, and I could cut a tiny piece. So I thought, “What’s the harm? I’ll try a little.”

To my surprise, it was the most drool-worthy seafood I’ve ever had. I not only finished that scallop, but had two more—and secretly hoped my coworkers wouldn’t take their share so I could eat more.

So what happened there? I was 100% certain I didn’t like scallops, until I liked them. I’m sure you’ve had a similar experience of discovering one day that something you had written off wasn’t so bad after all—or was even, dare I say, good.

Sometimes we think we don’t like something, or it doesn’t or won’t work for us, because we had a bad experience with it in the past.

But consider this: it’s possible what you experienced was a very limited sample size of what this thing is or could be.

How does this apply to sharpening your mental models? The purpose of mental models is to have shortcuts that help you make sense of a noisy world without having to think from scratch.

For mental models to be useful, they should help you make smarter decisions. But the outside world is constantly changing. Your inner world is constantly changing. Something you once believed might not apply anymore.

That’s why I believe you should break your own rules once in a while. You should constantly be testing your rules, boundaries, hunches, intuition, and hypotheses.

When you test or break your own rules, there are two things that can happen:

1. You’ll have a bad experience. You’ll say, “Wow I’m so glad I have this rule.” Then you can re-subscribe to your rule and continue on your merry way.

2. You’ll realize the result was better than expected. Maybe your rule was overly broad. Maybe in certain situations, the rule doesn’t apply. Then you can come up with a more accurate, nuanced rule that better serves you.

A caveat: You should hold true to your values and avoid doing anything that hurts others. Aside from that, try to break your rules in as low-cost of a way as possible. Don’t do it in an area that’s irreversible or expensive to fix.

It’s extreme to say no to an entire category forever. Remember how at one point, everyone said, “I like all kinds of music, except country”? It was just something people around me said, so I said it too. Years later, I realized country is awesome and it’s been one of my favorite genres for two decades.

I’m giving non-work examples here, but you can easily see how this applies to mental models for your work, function, tactics, etc. This practice of regularly questioning my own rules and updating my hypotheses has brought many good things into my life.

To be clear, from a practical perspective, I get that you can’t constantly update your mental models because the whole point of heuristics is to limit thinking. If you had to think from first principles each time, what’s the point of a rule? So you have to use your wisdom and judgment here. You can have heuristics, but hold them lightly. You should have a point of view, but stay open to changing your mind and admitting that what you know might be limited.

What are some “scallops” in your life? The next time you reflexively say “no,” think about whether you could be more nuanced with your approach.

You might say to yourself, “I thought X didn’t work for me. But now, I realize it could work in certain situations. Therefore, I’ll update my mental model, which should lead to better decisions over time.”

If this newsletter resonates with you, here are three more ways I can help:

1. Follow me on Twitter or LinkedIn for bite-sized tips throughout the week (free).

2. Work with me for 1:1 executive coaching or advisory consulting. Hit reply and I’ll send you a few questions to see if we’re a fit.

3. Book me as a keynote speaker. Reach out at wes (at) weskao (dot) com

Thanks for being here,
Wes

PS See you next Wednesday. To binge-read in the meantime, check out these essays:

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How to on-board yourself when you join a new team Wes Kao · October 18, 2023 Read full story

11 ways to get better feedback from your manager Wes Kao · Mar 20 Read full story