Failure #5: When Your Biggest Failure Becomes Your Legacy

Unless you’ve been living off the grid without internet access (which seems unlikely if you’re reading this), you’ve probably seen the video.

You know the one: a Coldplay concert. Gillette Stadium. The Kiss Cam.

It zooms in on a couple mid-embrace and when they see they are on the big screen, they immediately hide. The crowd murmurs.

Chris Martin pauses on stage and says: “Either they’re having an affair… or they’re very shy.”

Unfortunately, Chris Martin’s first guess was right.

It was Andy Byron, CEO of Astronomer, a $1.3 billion tech company, kissing his HR chief Kristin Cabot not his wife.

The moment went instantly viral.

100 million+ views. Even more memes made about the situation.

Byron resigned two days later. 

On the surface, it might seem like a guy who was otherwise successful and respected made one mistake and lost everything including his reputation. But that’s not true. 

This wasn’t one mistake. It was the end of a long chain of misaligned decisions.

Because what actually breaks your legacy isn’t failure, it’s the choice you make to live out of step with who you claim to be.

When Failure Stops Feeling Redeemable

At this point, you might be wondering: how does a story like this — messy, embarrassing, and morally complicated — fit into the Learning to Fail framework?

Surely this kind of failure is just… bad. Shameful. A cautionary tale. There can’t be any growth here. This was a guy pretending to be something he wasn’t, and that’s just crappy, right?

What if I told you I’m not so sure? What if I told you even failures that feel irredeemable can teach us something. In fact, those are often the most instructive of all — not because they’re brave or courageous or admirable, but because they force a reckoning.

In this case, we’ve got an incredible lesson — for anyone willing to listen — about the cost of sustained misalignment. In fact, Byron’s story is a great example of how failure isn’t always the result of risk. Sometimes it’s the result of pretending.

Pretending to be someone you’re not.

Pretending you’re fine when you’re not.

Pretending your actions won’t catch up with your identity.

Byron’s failure wasn’t that he got caught. His failure was that he’d spent too long building a life that couldn’t withstand the truth. And when the truth showed up — quite literally on a jumbotron — everything else collapsed.

We might not experience our unraveling in front of 60,000 people and 100 million viewers, but the lesson still applies.

The Kind of Failure That Saves You

The truth is, failure doesn’t have to be noble to be valuable. It doesn’t even have to be public. It just has to teach you something honest enough to change how you live.

This is how even a story like the Astronomer CEO getting caught cheating on a Kiss Cam at a Coldplay concert — a string of words I never imagined writing a week ago — fits perfectly within Learning to Fail. In our minds we can easily distance ourselves from people who fail that badly, the reality is: all of us are capable of living out of alignment.

That’s not a question of morality. It’s a question of momentum.

You keep saying yes to the wrong things long enough, and one day, you’ll find yourself standing on a stage you never meant to build, performing a version of your life that no longer feels like yours.

So no — not all failures are brave.

Not all failures are strategic.

Not all failures are survivable in the ways we want them to be.

But every failure, no matter how complicated, has the potential to reveal something we couldn’t see before.

And if we’re willing to look — truly look — then maybe that failure becomes the thing that stops us from living in hiding.

- Dr. D