No one can teach you to have conviction | Ben Kuhn

Appreciation

Importance

Date Added

8.1.25

TLDR

Learning from others can get you a model that makes 95% of the easy decisions, but the 5% that adds the most value yourself has to come from your own mistakes. Conviction matters particularly when there are long time-horizons (lagging success indicator). Making your own mistakes teaches you what how the world works differently than you expected, rather than how a mentor's model is wrong.

2 Cents

Enjoyed the personal narrative and examples that tied the entire story. Articulated an important intuition for me.

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Then we actually implemented the ideas. Some of them turned out to be net-negative—for instance, we tried changing the way we wrote data models, and ended up reversing course later. Others turned out to be way more helpful than I expected—for example, introducing a rational directory structure made it tremendously easier for new hires to navigate our codebase.

Overall, I probably did a pretty bad job. But, importantly, I was able to see my mistakes play out in the real world. Instead of modeling what other people would tell me to do, I built a model of the problem directly. So when I got negative feedback, it wasn’t “Mentor X thinks this plan is bad” but “the world works differently than you expected.”

The critical 5%

If you join a company where someone else is already making those decisions well, you’ll never get the type of practice that you need in order to build your own models and heuristics. You’ll end up with a good, but not perfect, model of “what would my boss do?”—a model that can make the 95% of easy decisions, but not the 5% of hard ones that add the most value.

Having mentors can help you quickly go from okay to great. But to get from great to exceptional, you’ll need to make good decisions when the stakes are higher and the consequences are longer-term. For that, you need a kind of conviction that you can’t learn from mentors—only from your own mistakes. So get out there and make some!

(Also, what conviction is):

Because the stakes are higher and it takes longer to see the results, all these decisions require what I’d call conviction: the confidence that your idea is good enough that it’s worth throwing a lot of effort behind.

If you’re designing a hiring process, or investing in a particular code migration, or moving people between teams, you’re committing to spending a lot of resources following through: training new employees, finishing the migration, etc. In order for that commitment to make sense, you want to be confident that your plan is optimal before you pull the trigger.

It turned out that, even though I was good at lower-stakes engineering decisions, I was still pretty bad at ones that required conviction—I couldn’t get confident enough to commit to anything.