Last Updated: March 30, 2026
This article originally appeared in The Tennessean.
t’s college football season and my team’s on a losing streak.
This is nothing new for me. No matter what team I have hitched my wagon to over the years, a national championship has never been in the cards. Losing, whether by a lot or a little, has been a consistent theme.
I grew up a Vandy fan and experienced a profound sense of loss for years on end. We had a few upsets and some moral victories, but even in our best seasons, suffering through a decent number of losses felt inevitable. It was sometimes tough to be around friends whose teams seemed to always be winning—but I was happy for them (at least sort of) as they got to celebrate while I sulked.
Why couldn’t I experience the thrill of victory like they did?
It took me only a few decades to have an epiphany: I didn’t have to root for just one team. Although I consider myself a very loyal person, celebrating a win is much more fun than suffering over a loss. Why not find a winner to root for?
At the bequest of a friend who bribed me with a free team jersey and some hot wings at a watch party, I decided to become an Oklahoma Sooners fan.
At first my friends and family laughed at my sudden life-changing decision. Given the fact that I’d never actually set foot in Oklahoma, they all thought it was weird. But I theorized that the Sooners have had great teams for decades. Following a team that had a history of winning more than losing seemed like a logical way to make Saturdays in the fall better. I was all in—Boomer Sooner!
But it was only a few games into the season when something shocking happened. They lost a game. No matter who you root for, it seems that losing never completely goes away.
It’s the same way in business. Over time, no business has ever gone undefeated. Just like the top football teams, even the most successful companies don’t win 100% of the time. Whether you run a big corporation or a one person startup, the way you deal with setbacks and losses can determine your long-term success.
When I first got into the IT consulting and software development business 30 years ago, losing really hurt. Whether it was losing a sale or losing an employee, I reacted by losing sleep.
But somewhere along the line I came across a great quote that changed my attitude:
“When you lose, don’t lose the lesson.” — Dalai Lama
This sounded simple enough. If a loss can teach you something that helps you improve, you will ultimately come out ahead. Maybe this Dalai Lama guy was on to something?
Given the competitive nature of business, it took me years to fully embrace this. Even with the silver lining of a lessoned learned, losses are hard to feel good about. So it takes some practice and humility to follow the Dalai Lama’s advice. But long term, it’s paid off.
Now, whenever we lose a big sale or lose money on a bad investment, I have found it helpful to literally write down the lesson learned. We then use these lessons to proactively tinker and tweak to help us win the next time.
So, as of this writing, my Sooners have lost three in a row. It’s not fun, but like every team and every business, the lessons learned from the losses will pay off. If your team has had some losses this year, as the Dalai Lama says, “Choose to be optimistic, it feels better.”
