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Stay centered around learning.

I have control issues. I feel like most founders find that statement relatable. One reason people become entrepreneurs is because they are anti-institutionalists seeking freedom from the status quo. They want to take back control over a system and/or liberate others from one.

What people don’t usually tell aspiring entrepreneurs though, is that the path of starting a business is full of obstacles and variables that you can’t account for or control. And building a team is literally the process of trusting others and relinquishing control to them.

Dealing with this reality was extremely difficult for me. I took challenges and setbacks very personally. I would constantly ruminate on my own failings and beat myself up when things didn’t go “according to plan”. However, the worst part about this habit was how it affected my relationship with my girlfriend, Sarah, who joined our team as a frontend developer for a short time.

Sarah came onto the team because we needed help doing a big rewrite of the app. She was a frontend web developer, but didn’t have any experience with the tech stack we were using for the web-app. She needed a lot of support and guidance to get up to speed and make progress, but it was a high-stress time in the company, and I had no patience left to give. It was horrible.

Anytime she asked a question, I was a total ass and made her feel like shit for not already knowing the answer. I was condescending, rude, and hurtful in my interactions with her. There were multiple weeks where we did not want to speak to each other at the end of the day. I’d apologize and tell her I’d try to be better, but I was so insecure and distrusting we eventually decided to have Sarah collaborate with Keith on the rest of the rewrite.

Sharing this failure as a leader and, more importantly, a partner fills me with so much shame, but I feel it’s important to be honest so that others might learn from my mistakes.

If I could go back, I’d tell myself to breathe and stop taking to heart what can’t be controlled. Some people just won’t like or understand your product. Some people won’t respond to your emails. Some people will unsubscribe from your newsletter. No matter what you do, these outcomes will happen.

The important thing to do is to control what you can control - your outlook and approach moving forward. I’ve found recently that focusing on learning is a helpful guide to keeping your head up and staying positive in these moments of failure. Recognizing that the current obstacle gifts you the opportunity to know more today than you did yesterday - whether or not you overcome it - is an empowering inner monologue. As a leader, that modality also enables you to operate in service of your team’s learning over domination and control of their output.

This is very hard to actually practice, though. It takes self-discipline, patience and personal stability. However, the compounding benefits of this line of thinking are invaluable to me. It allows me to approach problems with genuine curiosity instead of the spiraling anxiety that plagued me when I felt I had failed myself or others.

It allows me to control what I can control - instead of allowing what I can’t control to control me. And that’s freedom, baby.

Note: This is part of a larger blog series on 10 Things I Learned From My First Failed Startup. Checkout the rest of the series and tweet your thoughts at me.

Drew Lyton
Drew Lyton
Friday, February 4, 2022

I'm a software engineer, ex-founder and writer who cares deeply about creating a better relationship between technology and society. I'm currently writing a book about early stage entrepreneurship.


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