As I watched my children rip open their Christmas presents, I felt an unexpected sadness. I knew that the joy of that toy they wanted for so long would pass. Soon, it would be replaced by the next obsession. Having children has a way of pulling you back in time, forcing you to think about your childhood and the regrets that still linger.
One of my biggest regrets was never trying out for my high school basketball team.
I was a freshman at McLean High School in Northern Virginia, fresh from Kuala Lumpur. My main goal was to just fit in and not just be a criminal. I made the varsity tennis team as a freshman, but when basketball season came around, I was frozen.
I had told my PE teacher that my goal was to make the basketball team. We practiced regularly. He believed in me. I believed in myself. Then the tryouts came, and I didn’t show up. I was very scared.
Basketball has been my passion since I was in sixth grade in Malaysia. Michael Jordan was my hero, the unquestioned Goat, and I wanted all his shoes. My family couldn’t afford them, so my best friend Todd Adams gave me his Jordan 5s, two sizes too big. I looked silly walking around in them, but to me, they were magic.
That regret stayed with me for thirty-three years. Until now.
Finally Shot My Shot
Every Sunday night at my children’s school, there is an open basketball game in the new gym. Free for dads, friends of dads, and employees. When I first heard about it, I was intrigued but also terrified. I have known my fathers torn ACLs, and my left ankle has sprained over twenty five times. I always wear an ASO ankle brace when I play any sport.
After avoiding it for half a year, a father named John – six feet, two hundred and thirty-five pounds – asked me to come. I gave my usual excuses about risk of injury and looking stupid. He waved and said I’ll be fine.
When I finally arrived, I was surprised. About 70% of the players were under the age of 35, and almost half were under the age of 30. The pace was much faster than I expected.
Since I hadn’t practiced in over ten years, I focused on self-defense. At 5′ 10″ and 168 pounds, I was on the smaller side, but I embraced my inner Draymond Green and locked in.
I caught two players winless in two different games. I then identified the leading scorers, set up screens, and passed the ball to open up my teammates. We won the first game, and I knew I could hang on.
You’ve Got an Amazing Gift
On the last play, the best player on my team drove to the basket, kicked the ball away from me at the top of the key, and I sank a three for the game winner.
I couldn’t believe it. Like one of those slow motion, out of body experiences where you see the ball go through the air, and then you swing! It was one of the best feelings I’ve had in a long time. I’d put it up there with negotiating my divorce in 2012, which felt like winning the mini-lottery and escaping the corporate grind.
Showcase Action Changed Everything
As you get older, regrets pile up. Some are small, like not trying. Some survive, like not asking someone or not investing money if you have money.
My biggest fear about playing was getting injured, followed by looking like I didn’t belong. If I got injured, I wouldn’t be able to play with my children, which would be bad and add burden to my wife.
But apparently, everything changed. I got to know an editor, an eighth grade teacher and a guidance counselor who helps with high school applications. I met four other fathers that I truly admire. And I finally let go of the regrets I had been carrying for over thirty years.
Even if I played badly, I would still have fun. No one could make fun of me, as I was afraid. As a school parent, I belonged, even if I thought otherwise.
Not feeling like you belong is a common thing, perhaps even more so for the young and outsiders. We fear being laughed at, criticized, ostracized, and looked down upon. But the more you practice showing up, the more often life rewards you.
I am also surprised
My biggest surprise was realizing that I was faster and in better shape than about 75% of players because of playing tennis and water polo three times a week for over 20 years. But in my mind, I had told myself that I couldn’t go on. Fitness becomes a great equalizer as you get older.
When I played four years of 5.0 USTA tennis, most of my opponents were former college players who were more skilled, but fitness allowed me to compete. I even watched one of my teammates play for William & Mary while I was there, only to be on the same court with him 23 years later.
I had a bad record, but at least I came. In contrast, my 4.5 team mate decided to quit after bumping into 5.0.
It’s Time to Fix Things
Windows of opportunity don’t stay open forever. They close faster than you think. You only get so much time with your kids before they prefer hanging out with friends. You only get so long to build wealth before the next bear market hits and you lose your job.
I knew that if I didn’t try organized basketball at age 48, I might never have another chance. And if I ever tried, I would take that regret to my grave.
Now my goal is to stay healthy and continue to play without injury. I’m still wary of twisting an ankle or sprain, but I’ll continue to show up as long as my body is healthy.
Related: The Healing Power of Returning to Your Childhood Home
Life Regrets and Money Regrets Feel Surprisingly Similar
Solving this 33-year regret costs nothing. All I did was show up. Interestingly, these “life regrets” almost stuck with me as financial regrets, like aggressive day trading early in my career. They both expressed disappointment in me for not doing it right.
As I move through the second half of my life, I encourage you to write down the regrets that are still holding you back and resolve them before it’s too late. Every time you do that, your soul feels lighter.
Personally, I will cherish the feeling of hitting that first game with three wins forever. And two weeks later, I even hit a third step back from the side to win another game. You never know until you try!
Readers, what life regrets have you fixed, and how? Are your life regrets as much of a concern as your finances?
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