Should I Feel Guilty for Failing?

No one will ever create more guilt over startup failure than the Founder.

Startup Founders have an insane ability to manufacture epic amounts of guilt over their own failures. It's almost like we do some magical alchemy that takes every pound of failure or criticism and turns it into a metric ton of guilt.

But should we really feel this guilty over failing at our startups?

There are two answers here. The first is — everyone does it. But that is of very little help. The second answer is just "no." Failing at a startup is painful but should not be a source of guilt. Guilt comes from our misunderstanding of what actually just happened.

Startups Typically Fail

For those that are unaware, most startups fail. Most Founders are doing this for the first time with a product that has never existed, run by a team that just got assembled, and heading into a market that's unproven. It's a recipe for disaster.

The anomaly is when it works. The problem is that in order for things to work, we would have to time so many variables in such a way that they all turn up positive at the same time. It can happen, but... it usually doesn't.

The problem is that, as Founders, we only see the lens of startup success through our own singular effort. We essentially have one "at bat" where we either hit it out of the park or strike out in grand fashion. Start enough of these companies, and "failing" will become common. I'm 4 for 9 in successful startups over a 30-year period, and I teach Founders how to build startups for a living. This shit is hard.

We Sentence Ourselves to Prison

What we all invariably do is create a mock trial in our heads where we are clearly found guilty by everyone involved. In this fictitious trial are staff members, customers, investors, and even our friends. They are all standing up and testifying about what a horrible job we did and how incompetent we must be.

Collectively they set our sentence to a "lifetime of guilt to be served with nonstop panic attacks and perennial depression." The startup judge bangs his gavel while his olde tyme gray wig while those curly things bounce up and down. I have no idea why we have a caricature judge from 1820 in this fantasy, but it's all bullshit anyway, so just run with it.

We run this fantasy so many times and so passionately that, at some point, we actually believe it's true. We believe those testimonies happened, and our fate was decided. But here's the thing - it was all just a fantasy. Unless our name also happens to be Elizabeth Holmes, absolutely nothing really occurred. We made it all up.

Write a Different Eulogy

The answer here isn't to spend more time intellectualizing it. The answer is to write a final ending. Every failed startup needs a eulogy, whether it's ever shared or not. Think of this as not just a thought exercise but also an emotional endpoint.

Write down what we set out to do. Detail what we thought was going to work and where it went wrong. List the lessons we could take away for the next one. Some Founders will be so bold as to create the typical "Here's how it ended" Medium post for others to learn from. But it doesn't matter — we just need to get it out of our heads.

Should we still feel guilty? No. We didn't set out to harm anyone; we set out to build a company. It didn't work, as is typically the case, but it was not out of intentional harm. We can feel sad, we can feel remorseful. But we should never, ever feel guilty for trying to build something great.

In Case You Missed It

How to Make Potential Failure Less Scary (podcast) While your mind can make it seem bigger than it is, most people won’t remember when a business shuts down — and processing your emotions include assessing your failure to get back up!

The Emotional Cost of Being a Founder When we talk about building startups, we talk about lots of costs: Staffing costs, the cost of capital, cost per acquisition, and opportunity cost. But we never talk about the biggest cost — the emotional cost.

Why Do I Feel So Alone? No one ever tells you in the “Starting a Company” brochure that the journey will not only include crippling anxiety, drowning in personal debt, and endless challenges — but also a healthy dose of personal loneliness.