On Screwing Up, Surviving and Succeeding

Sooner or later, you’re going to screw up. 

Doesn’t matter how smart or sharp or well-prepared you are, it’s going to happen. That’s just the way it is. But instead of fearing that moment — or running away from it when it happens — I want you to expect and embrace it as a necessary component of your success.

I’ll explain by way of a personal story.

Very early on in my career, I somehow landed a huge opportunity with a very large enterprise organization, with 3 or 4 locations across the country. A $20K project fee, which was 20X more money than I had ever seen on a single project up to that point. 

This was about 2 years in, when I’d just started my own firm. At a time when I still carried the arrogance of a young man like a badge of honor, fueled by an almost desperate need to prove that I was right. 

In other words, I was deathly afraid of looking or sounding unqualified or failing in any way.

Long story short, in complete isolation, I went down a path of making a massive set of recommendations for both their brand messaging and their product design and end-user experience. The kind of thing where you write this massive deliverable report and read it back and are damn impressed with yourself: yeah, this is brilliant. They’re gonna be SO impressed.

So once I got to the point where we were actually doing mock ups with a small group of folks, we had a big sit-down to unveil my brilliant plan to right all their UX wrongs.

And when it came time to sit down with the operations and the product development people and other executives who were never in the room prior to that, I – to put it bluntly — got my ass handed to me. 

These incredibly sharp people basically picked apart every item on my list, explaining why those suggestions were neither appropriate or feasible. From restrictive industry regulations I was completely unaware of to technical infrastructure constraints I never bothered to investigate, I was sinking fast with every minute that went by.

I was basically melting into the floor as this conversation goes on, so after the longest 30 minutes of my life, I just fell on my sword:

“I am truly, deeply sorry. All I can do at this point is apologize to you because there is a LOT of digging that obviously should have been done earlier in this process — and I did not do it.”

I absolutely failed to spend the requisite time figuring out who their customers were, how their industry worked and was regulated, and a hundred other nuances specific to that industry and that business. What I had I proposed was completely inappropriate.

I gave them their $20K back, wondering if I should be doing something else with my life.

And I struggled with this loss for months afterward….but I didn’t quit. As horrible as this was, I never made that exact same mistake again. 

What I learned is that, as the saying goes, you either win or you learn.

This is part of the process — when that grand failure doesn’t kill you, when you don’t die, when your career isn’t over, when you get another project — you realize that you can, in fact, survive things like this. 

Which gives you the confidence necessary to try again.

You also realize that this experience has taught you something important that actually makes you better at what you do. It makes you realize that you cannot and should not be afraid to fail.

You need to have some of those experiences, where you do go down a path and it doesn’t work. It’s a huge part of getting where you need to go. 

It’s not easy, because it hurts.

But, as another saying goes, it absolutely, positively does make you stronger. 

And that strength, that persistence, matters more than any other skill you have in your arsenal.

I am living proof. 

And so are you.