What If Failure Doesn’t Teach You Anything?

October 10, 2026

Earlier this week, I posted a quote from a podcast I was recently on:

“The things that may look like failures, and quite frankly oftentimes are failures, are also the same things that give us lift.”

I liked the line when I said it. I still do. But it got me thinking about failure.

We talk about failure all the time. Fail forward. Failure is the best teacher. What doesn’t kill you makes you stronger. You miss 100% of the shots you don’t take. We all know the lines.

But I’ve been listening to Mark Manson’s Solved podcast lately, and his episode on failure got me thinking about whether we actually believe all the things we say about failure. More importantly, are we actually any good at failing? Because I’m not sure I am.

Sometimes Failure Just Hurts

When I started thinking about the failures in my own life, one thing became pretty obvious: they aren’t all created equal.

There are failures I can look back on now and clearly see what I learned. There are others where I can point to a behavior I changed or a decision I would make differently today. There are plenty of little failures that really don’t matter much at all in the grand scheme of things.

And then there are failures that are still messy. I think we’re sometimes too quick to clean those up. We want the lesson. We want the redemption story. We want to be able to explain how this terrible thing happened but ultimately made us better. Maybe it did.

But maybe we’re just controlling the narrative because the alternative is admitting something painful happened and we wish it hadn’t. Sometimes there isn’t a clean lesson or one moment you can circle and say, “There. That’s where I failed.” Sometimes you can retrace every step, look at what you could have done differently, and still not know exactly what the lesson was.

That doesn’t mean we shouldn’t learn from failure. I absolutely believe we should. It just means we don’t have to immediately turn every painful thing into an inspirational story about how much better we are because of it.

Maybe I Was Chasing the Wrong Scoreboard

Professionally, I’ve had a lot of success. But I’ve also wondered whether one of my biggest professional mistakes was leaving a very good company to become a CEO. That sounds crazy even writing it. Who turns down the opportunity to become a CEO? But I’ve thought a lot about why that title mattered so much to me.

My career started as a PE teacher in the mid-1990s. Back then, there was this narrative in education that coaches were dumb. They don’t understand the curriculum and pedagogy. They couldn’t become principals. They weren’t instructional leaders. It was mostly B.S., but I think some part of me spent a long time trying to prove it was B.S.

I went from teacher to assistant principal, principal to the district office, then into the private sector, eventually becoming an executive and then a CEO. There was always another rung. Maybe somewhere along the way I started confusing climbing the ladder with winning.

I thought becoming a CEO might prove something. Maybe to other people. Maybe to myself. I don’t really know anymore. I even thought reaching that pinnacle of professional success might somehow make other parts of my life better. It didn’t.

The title didn’t make me happier or more valuable as a human being. In fact, it came with plenty of additional stress. I had reached one of the biggest professional goals of my life and discovered that the title couldn’t deliver most of the things I had unconsciously asked it to deliver.

That’s a heck of a lesson.

Being Comfortable in Your Own Skin

On that same recent podcast, I said something about success that I’ve kept thinking about: success is being comfortable in your own skin.

Maybe that’s one of the smarter things I’ve said, because who really cares? You’re ultimately the only person who knows what success means in your life.

Success can be money. It can be freedom. It can be happiness, great relationships, good mental health, building a company or leaving one. It’s different for everybody. The problem is that for a long time, I think I was asking different questions. What does everybody else think a successful career looks like? What does everybody else think a successful life looks like?

And here’s where I’ve landed:

If you’re having to be somebody else to think that you’re successful, then you probably have failed.

That’s a very different definition of failure than the one I had at 30.

Does Failure Actually Teach Us?

This is probably the biggest thing I’ve been wrestling with. We love saying failure teaches us, but does it?

I think you know you’ve actually learned from a failure when you’ve changed your behavior. Otherwise, there’s a decent chance you’ve just changed the story. I’ve certainly done that. Something happens and we tell ourselves it happened for a reason, it led us somewhere better, or we’re stronger because of it. Maybe.

Or maybe we’re just controlling the narrative because the alternative is admitting something painful happened and we wish it hadn’t.

There’s also a difference between wanting to change and wanting to talk about changing. You can keep saying, “I’m going to do this,” over and over again, but at some point, if something really matters, you have to take action. You have to build different habits, communicate differently, make different decisions or actually behave differently.

And even that isn’t permanent. You can learn something, change your behavior for a year, and then fall right back into the same old patterns. You can know exactly what’s better for you and still not do it.

Failure doesn’t hand you a lesson on a schedule, and learning the lesson once doesn’t mean you’ve learned it forever.

The Hamster Wheel

I think there’s another kind of failure that’s even harder. It’s when you already know the lesson and you just don’t want to hear it.

You really want something to work. You see all the potential in it and all the reasons it could work, but you also see the pattern. Maybe that pattern keeps causing pain, and you keep going around the hamster wheel hoping this time the answer will be different.

Sometimes it will be. Sometimes persistence is exactly what gets you through. Sometimes you’re being resilient. And sometimes you’re just being stubborn. I’ve been both.

For me, one of the differences comes down to the data. We rarely have all the information we want when we’re making big decisions, but we usually have some information.

When I left public education, I gave up an incredibly stable career with a pension, a predictable retirement, and a clear path forward. But I also saw an opportunity to grow professionally, challenge myself in new ways, and explore possibilities that simply weren’t available to me in my current role. There were no guarantees it would work out, but I had enough information to believe the opportunity was worth the risk.

The problem comes when we stop looking at the data because we desperately want a different answer. That can happen in a job, a relationship, our health or almost anything else. Sometimes resilience means continuing despite difficulty because there is real evidence that what you’re doing can lead somewhere better. Stubbornness is continuing because you’ve already decided what you want the answer to be.

So Does Failure Give Us Lift?

After thinking about all of this, I still believe the quote that started this whole thing. I really do. I just think it’s more complicated than it sounded when I said it.

Not every failure gives us lift. Some failures don’t really matter. Some are dumb things we did and hopefully won’t do again. Some hurt like hell. Some take years before we understand what they were trying to teach us, and some may never provide the clean lesson we’d like them to.

But the failures that really change us force us to examine something deeper: our habits, our relationships, our identity, our definition of success, our behavior and, maybe most importantly, the scoreboard we’re using.

I’m 53 now. If I’m lucky enough to still be above the dirt at 73, I don’t think I’ll judge the next 20 years by whether I collected another title. I’ve already proven I can do things. Failure would be spending another couple of decades chasing something that doesn’t actually matter to me just so I could prove something to somebody else.

I want to live life the way I want to live it. There will still be jobs, bills, responsibilities, zigs and zags, and I’m sure plenty more failures. But success for me now looks a lot more like being comfortable in my own skin, having fun, having good people around me, feeling good about my life and spending a lot less time worrying about what everybody else thinks.

Maybe that’s what failure has actually taught me. Or maybe I’m still learning.

Probably a little of both.