Failures That Aren't Really Failures At All

A few weeks ago, I set up this newsletter promising you fresh weekly ideas — and immediately fell off the wagon.

Sorry about that.

If you’ll allow me, I'd like to explain what happened.

I will also ask you for a little extra grace, as the complete story probably deserves a full book (which I intend to write in the next year or two)… for today, though, let’s start with failure.

What do you think of when you hear the word "failure?"

To me, even the word itself feels like a big bummer. A let down. A big 'ol 'womp womp' noise. It's almost like an emotion… and not a nice one.

Over the last few weeks, I've been contending with something that could be considered a HUGE failure:

I had to close the business I've been working on for the last 5 years.

This wasn't a quick, painless death, either. It was slow and grueling, often gruesome to watch and heart-wrenching to bear.

At our height, our team was around 20 people from all over the world, kicking proverbial ass and building a seriously cool product. We had crafted a unique solution to a problem that costs global businesses $400B/year. We had a beautiful and diverse self-managing team with tremendous psychological safety, we created all our own content in-house, we had very little outside investment, our tech stack was ready for massive scale, and I truly believed we were building a billion dollar company.

But now it's dead.

Like most things, this closure happened gradually and then suddenly. A few Fridays ago I found myself on a crappy government website paying $10 to file company dissolution paperwork with the Secretary of State.

It was an utterly underwhelming, bland, wholly unclimactic end to the dramatic roller coaster saga that consumed the last five years of my life.

I should also tell you: I’m quite scared to publish this.

I badly want you to see me as a “successful” entrepreneur, a leader who's always "killin' it," a businessperson “crushing it," yada yada.

I find myself wishing I would’ve just raised a pile of money (because for some reason that alone is considered ”a success” but that’s a topic for another day).

I catch myself thinking about all the things I could've done differently.

I feel an intense impulse to skip past these gory details and talk about a brighter future.

But I really think we first have to talk about failure.

Was this closure a failure??

It makes me think of my marriage. I was in a committed relationship with an amazing human for almost 20 years and in 2020 we decided to uncouple. People often talk about ended relationships like mine as “failed marriages,” but I am, frankly, insulted at the very thought. To me, my marriage was the opposite of a failure — it produced nearly two full decades of deep friendship, quite a few fabulous adventures, and two incredible kiddos. I wouldn’t change it for the world.

As I look at this business closure, I find myself with similar reflections.

Because as painful as it is to admit, I already know I could not have learned a fraction of what I have if there had been a “successful” outcome for this project. As annoying as it is (and it IS annoying, because parts of me would greatly prefer the trappings of success), I am unquestionably a better CEO, entrepreneur, and leader — not in spite of this massive “failure,” but because of it.

So… is it really a failure at all, then?

Maybe whatever this is is something else entirely… something we don’t have a good word for.

I think the closest I can get might be a phrase: “Sometimes you win; sometimes you learn.”

Since we’re in confession time, I’ll share one more.

I started speaking around 2011, just before my book came out. I was 30 years old, and though I really did know some things (mostly about leadership and an assessment then-called StrengthsFinder) I mostly felt like I was making it all up, constantly.

I was in hardcore “fake it ’til you make it” territory for YEARS. I leaned heavily on my intuition (which tends to be solid) and probably more than a little on the fact that pre-beard me looked even younger than I was, which I suspect gave me some kind of bonus “wunderkind” shine.

But now… now I’ve been beaten up a bit. By my divorce, by a pandemic, by being a parent for the last decade+, by running a tech startup, on and on. As my middle-schooler will happily tell you, these days there’s quite a lot of gray appearing in my beard.

Now I know many, many things I simply didn’t know before. I have "experience." But as Little Red says in Into The Woods: "Isn’t it nice to know a lot? And a little bit not."

Or... maybe it's actually all nice?

I like to think the adage “nowhere to go but up” will apply to whatever comes next, but then again, I’m starting to see that, in many ways, maybe I’m already “up.”

Like failure, I'm learning it all depends on how we look at it.