Youth Sports, Challenges, Failures, and the Fuel for Life

Lately, I’ve been having a lot of conversations with my longtime friend and York IE co-founder Adam Coughlin about our kids. They’re reaching that age where youth sports stop being about orange slices and start being about winning and losing, roster spots, cuts, tryouts, playing time and stars and role players.

It’s an adjustment to watch as a parent and can create flashbacks for those who grew up playing sports. Oftentimes, kids equate “making the team” or “getting minutes” with self worth. And many parents, let’s be honest, tend to live vicariously through those realities. The sidelines can feel more intense than the games themselves.

But here’s the thing Adam and I always come back to: the point of playing sports, the ultimate value in it, isn’t the trophies. It’s the lessons.

I look back at my own childhood. Sure, I was one of the better athletes in my grade, but I didn’t always make the team or get all the fanfare when I did. I was told I was the last kid cut from the Little League All-Stars, the same team that went to the regional finals and had a blast winning games. I remember feeling left out and being heartbroken. In basketball, I was passed over for travel teams because the coaches’ kids were slotted in. In high school I got cut from JV baseball and never played again and in track I didn’t make the relays so hung those spikes up too. Some things, to me back then, were insurmountable when paired with indifference. 

In football, my chosen sports obsession, I pushed to play at the highest levels of competition in high school and college and I achieved a great deal of accolades individually and part of a team – but I also quickly realized I wasn’t going pro (blog post about my college football coach Peter Yetten, a legend). In college I learned how to go from “star” to “role player.”

We all must retire from sports at some point of time and find our path with the lessons as a foundation. Those learnings above were all hard pills to swallow. But they were also the most important ones, even if at the time I struggled to see that.

Because here’s what playing sports growing up really teach:

How to build camaraderie with a group of people
How to prepare for big life events
How to be resilient when things don’t go your way
How to embrace a role for the good of the team
How to work harder when talent alone isn’t enough
How to keep showing up after setbacks and failure

These lessons have shaped me far more than any MVP plaque or state title. They’ve shaped Adam too. And they’re the same lessons we carry into York IE every day as we help entrepreneurs navigate the toughest game of all: building companies. 

Failure fuels success

With that, I will say we do try to try and chase the thrill of the Friday Night Lights and the big touchdown. We feel lucky that we’ve found a career as fulfilling and rewarding that takes us back to that adrenaline and euphoria from time to time. 

Here’s the truth: failure in youth is a gift. It’s the chip on the shoulder, the log on the fire, the fuel you carry with you into adulthood. Michael Jordan’s NBA Hall of Fame speech was on point on this topic. Doubt me, slight me, I’ll remember in this activity or the next. And when channeled the right way, that fuel can power successes far bigger than a game-winning shot or on the field glory.

So parents, I challenge you:

Encourage your kids to play sports. Encourage them to have fun. But don’t rob them of the hard lessons by making it all about winning or being the star. Let them fail. Let them sit on the bench. Let them play pick-up, club or recreation. Because those are the moments that prepare them for the real world.

For me, those failures weren’t the end. They were the beginning. And they still drive me today.

That’s the startup game in a nutshell. You will get cut. You will lose customers. You will watch competitors win deals you thought were yours. And if you’re serious about building, you will put your head down, keep grinding, and become the kind of teammate who makes the whole team better and perseveres with grit and a long game view.

Adam and I carry this mindset into York IE every day. We know the wins feel great, but the lessons come from the setbacks. Those chips on your shoulder, those logs on the fire — they’re what drive you to build bigger, better, and stronger.