Failure Sucks. Give it a try.
- Matt Fitzsimmons
- Apr 14, 2025
- 5 min read
Let's not pretend failure is a good time. The motivational industry has done a lot of
work to rehabilitate it, to dress it up as a necessary step on the journey, a badge of honour, proof that you were brave enough to try. And while there's something to that, it skips over the part where failure is genuinely awful.
It costs money. It costs time. It costs sleep, relationships, confidence, and sometimes things you can't replace. Anyone who tells you otherwise either hasn't failed at anything significant or has tidied up the memory enough that it no longer resembles what actually happened.
So let's start there. Failure hurts. It really does.
Now let's talk about what it's actually worth.
What Failure Teaches That Nothing Else Can
There are things you can only learn by getting them wrong. Reading about cash flow problems is not the same as living through one. Understanding intellectually that a difficult conversation delayed becomes a crisis doesn't prepare you for the specific, personal experience of watching it unfold. Knowing that a market might not respond to your product is different from finding out, with your own money on the line, that it won't.
Experience compresses time. But failure compresses it faster than success does, because failure forces a level of examination that success rarely demands. When things go well, there's not much reason to pull it apart. When they go badly, you have no choice.
The owners I've worked with who are genuinely sharp, who make decisions quickly and well, who don't repeat expensive mistakes: almost without exception they've failed at something significant and done the work to understand why. That's not coincidence.
Success lets you move on.
Failure makes you sit with it.
The sitting is where the learning happens.
The Difference Between Useful Failure and Wasteful Failure
Not all failure is created equal. There's a meaningful difference between failing at something new, something you couldn't have fully anticipated, something that required a risk to attempt, and failing at something you've already failed at before because you didn't pay attention the first time.
The first kind is the price of growth. The second kind is expensive stubbornness, and it deserves less sympathy than people usually give it.
The variable is reflection. A failure you don't examine is just a loss. A failure you examine properly, honestly, without the ego protection that usually shows up in these moments, becomes an asset. It changes the way you approach the next decision. It recalibrates your instincts. It makes you better at the thing you're trying to do.
The question after any significant failure is not how do I move past this as quickly as possible. It's what is this telling me that I need to hear. Those are very different questions, and most people ask the first one.
The Identity Problem
One of the reasons failure hits business owners harder than most is that the business and the person are often the same thing, at least in their own heads. When the business fails, or when a significant decision fails, it doesn't feel like a commercial setback. It feels like a personal indictment.
This is understandable and also dangerous. Because if failure means you are a failure, the natural response is to avoid it at all costs. You stop taking risks. You stop trying things that might not work. You start making decisions based on what's safe rather than what's right, and safety has a very specific cost in a competitive market.
The owners who recover from failure fastest, and who build the most interesting things on the other side of it, tend to be the ones who've developed the ability to separate what happened from who they are. The decision was wrong. That doesn't make them incompetent. It makes them a person who made a decision that didn't work, and who now knows something they didn't know before.
That's not semantics. It's the difference between learning from an experience and being defined by it.
The Ones Who Never Fail
Worth noting: the people who never fail aren't succeeding. They're not trying anything interesting enough to fail at. Their businesses are safe and small and carefully managed within the boundaries of what's already been proven to work. Some of them are fine with that. Most of them, if you sit with them long enough, aren't.
There's a particular kind of regret that belongs to the person who played it safe and watched someone else do the thing they were thinking about doing. It's quieter than the regret that follows failure. It's also harder to recover from, because there's nothing to learn from it and no way to redeem it.
At least failure gives you something to work with.
The person who never fails isn't winning.
They just haven't tried anything worth failing at.
What To Do With It
When you fail at something, give yourself a reasonable amount of time to feel bad about it, because you should. Then do three things.
First, write down what actually happened. Not the story you'll tell at dinner parties in five years, but the actual sequence of events and decisions. Where was the first wrong turn? What did you know and when did you know it? What did you ignore because it was inconvenient? Be honest with yourself in a way you probably won't be with anyone else.
Second, separate the things that were within your control from the things that weren't. The market shifted. A key person left. A supplier failed. Some of what happened wasn't your fault. Some of it was. The goal is to be clear about which is which, because you can only learn from the part you owned.
Third, decide what you're going to do differently. Not a long list of resolutions, just one or two concrete changes in how you approach decisions or manage risk. Write them down. Come back to them.
That's not a complicated process. It's just the work most people skip because it's uncomfortable. The ones who do it build something genuinely useful from the wreckage. The ones who don't just carry it.
The Long View
Every business owner who has built something worth building has a failure in the story. Usually more than one. The failure is not incidental to the story. In most cases it's load-bearing. It's the thing that sharpened the thinking, changed the direction, or revealed the character of the person building it.
That doesn't make it good. It makes it useful, which is a different thing, and a better thing to aim for.
Fail occasionally. Fail at things worth attempting. Then do the honest work of understanding what happened, and use it.
The alternative is a very tidy, very small life.




Comments