The Midnight Library for Founders: Facing Regret & Failure

Kate Carney
3 min readJul 14, 2022

Startup culture celebrates failure as a necessary part of success. As an inevitable part of the journey. And it is, no doubt.

Success represents the 1% of your work which results from the 99% that is called failure.” — Soichiro Honda, the Founder of Honda

Yet, all too often, the narrative goes a little like “so I made this mistake, or this product or strategy failed, and then …. I reached unicorn/decacorn status or had this flashy 9-figure exit.

That’s not all that helpful. Sure, there are lessons within the failures but there is rarely the critically important discussion of how shitty it felt in the moment! Of how hard that interval between failure and success can be for any founder.

What we need is in-the-moment vulnerability. Vulnerability is not arming yourself with success before talking about failure in the past tense.

The Midnight Library

A few months ago, I read The Midnight Library. Between life and death sits a library, a timeless universe in which a person faces their regrets and has infinite opportunities to explore what could have been.

Each book represents an opportunity to experience the outcomes or consequences of a different choice made in one’s life. Big or small.

In this way, the books, allow one to erase regret. The “what if” or “what could have been”. A forever missed opportunity or loss vs. failure the opportunity for a second chance. An opportunity to extract the lesson and iterate until you find success.

Regret is the unknown; failure a known outcome and data point for what didn’t work. Regret is an opportunity to do better in the future, but the damage is done; failure a lesson that reflects progress.

How to Be More Vulnerable

First, talk about your feelings in the moment. As founders go through this period following a failure or mistake, they can feel shame, depression, isolated, deflated, disappointed, scorn, and/or regret.

This is what is missing from the typical narrative. Sharing those feelings is true vulnerability. Not only if you find yourself on a stage or the subject of an interview, but in the moment with your team.

I am not saying have a break-down or anger fest with the team. In fact, you may also need to explore your feelings with a trusted outsider like a coach, mentor, or advisor, to get that objective perspective.

Share your feelings and ask your team how they are feeling.

For example, in a team meeting, you can ask everyone to say 3 words that describe how they feel. What is true for them in that moment. Fear, frustration, anger, confusion …

Second, find the emotional space to objectively reflect; to do the deep dive, the post-mortem, extract the learnings to be applied to the next business decision, or version 2.0 of your product or service.

As a leader you should do your own objective reflection/assessment and discuss with a trusted peer or advisor. Come to the table with your observations and key takeaways.

But you should also ask your team what they think went wrong and why. What worked and didn’t work? What assumptions were wrong? Ideas for improvements? Vulnerability is about admitting you don’t have all the answers. You make mistakes. You are human.

What most of us fear, in fact, is that lack of control over the outcomes. Yet, every founder knows, startup life is all about embracing risk.

“I knew that if I failed, I wouldn’t regret that, but I know the one thing I might regret is not trying.” — Jeff Besos



Kate Carney

I help women entrepreneurs scale businesses. I am a business consultant and legal advisor.