Winning at mistakes: How to be a resilient founder even in the face of loss

Allison from Juniper
2 min readMar 8, 2023

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If the thought of making mistakes as a founder sends a shiver down your spine, you should read this.

[Picture from pexels.com]

First, let’s rip the band-aid off. You will make many mistakes as a founder. It may be scary at first, but the sooner you accept that the more forgiving (and, therefore, resilient) you will be.

In fact, making mistakes and bouncing back is a muscle that you can build. The trick is learning to return faster and getting really good at discerning what loss matters and what wins matter. Most people view them all with the same weight.

I will never forget being at a wedding weekend with my husband’s friends when we were playing some outdoor sports. I was up at bat with a Wiffle ball and striking out. Over and over I was striking out. I thought it was kind of funny, but everyone around me was getting increasingly uncomfortable. They kept shouting ways for me to improve, all of which I tried and didn’t work. My husband, who is annoyingly good at everything (including baseball, which he played in high school), was dying inside. I struck out a gazillion times, thought it was funny, and then let someone else go. I felt zero embarrassment and zero regret, but I noticed that OTHER people were uncomfortable with witnessing straight up loss.

I seem to be missing that gene. I like to take big swings. I can withstand enormous loss, and I don’t have as much loss aversion as other people seem to. If you don’t have these traits and want to be a founder, I encourage you to build them up. Do things you’re terrible at until it doesn’t matter that you’re awful at them. Laugh when you’re bad at something, and figure out how much it matters. Work obsessively on the ones that do matter and leave everything else behind.

Even if you’re not a founder, I encourage you to do some “loss/failure practice” every now and then on purpose. Put yourself in scenarios you will suck at. See what happens.

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Allison from Juniper
Allison from Juniper

Written by Allison from Juniper

Starting a new company in the pet space!

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