As I watched my kids tear through their Christmas presents, I felt an unexpected twinge of melancholy. I knew the thrill over that one toy they had wanted for so long would be fleeting. Soon enough, it would be replaced by the next obsession. Having kids has a way of pulling you backward in time, forcing you to reflect on your own childhood and the regrets that still linger.
One of my biggest regrets was never trying out for my high school basketball team.
I was the new kid at McLean High School in Northern Virginia, having just moved from Kuala Lumpur. My primary goal was simply to fit in and not just study hard. I made the varsity tennis team as a freshman, but when basketball season arrived, I froze.
I had told my P.E. teacher that my goal was to make the basketball team. We practiced every period. She believed in me. I believed in me. Then tryouts came, and I didn’t show up. I was too scared.
Basketball had been my obsession since sixth grade in Malaysia. Michael Jordan was my hero, the unquestioned GOAT, and I wanted every pair of his shoes. My family couldn’t afford them, so my giant friend Todd Adams gave me his hand-me-down Jordan 5s, two sizes too big. I looked ridiculous flopping 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 run in the new gym. It is free for dads, friends of dads, and staff. When I first heard about it, I was intrigued but also nervous. I knew dads had blown out ACLs, and my own left ankle has been 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 fellow dad named John – six foot four, two hundred thirty five pounds – asked me to come. I gave my usual excuses about injury risk and looking foolish. He waved it off and said I would fit in just fine.
When I finally showed up, I was surprised. About 70% of the players were under 35, and nearly half were under 30. The pace was far more intense than I expected.
Given I had not practiced in over ten years, I focused on defense. At 5′ 10″ and 168 pounds, I was on the smaller side, but I embraced my inner Draymond Green and locked in.
I held two players scoreless in two separate games. Then I identified the best scorers, set screens, and passed the ball to open teammates. We won the first game, and I realized I could hang.
Received An Amazing Gift
In the final game, the best player on my team drove to the basket, kicked the ball out to me at the top of the key, and I sank a three for the game winner.
I could not believe it. Like one of those slow motion, out of body experiences when you see the ball flow through the air, and then swish! It was one of the best feelings I have had in a long time. I would rank it right up there with negotiating my severance in 2012, which felt like winning a small lottery and escaping the corporate grind.
The Act Of Showing Up Changed Everything
As you get older, regrets accumulate. Some are small, like not trying out. Others grow heavy, like not asking someone out or not investing when you had the money.
My biggest fear about playing was injury, followed by looking like I didn’t belong. If I got hurt, I would not be able to play with my kids, which would be terrible and add a burden to my wife.
But by showing up, everything changed. I got to know the organizer, an eighth grade teacher and guidance counselor who helps with high school applications. I met four other dads I genuinely like. And I finally let go of a regret I had been carrying for over three decades.
Even if I had played terribly, I would still have had fun. Nobody would have made fun of me, as I feared. As a school parent, I belonged there, even if I thought otherwise.
Not feeling like you belong is a common experience, perhaps more so for minorities and foreigners. We fear ridicule, criticism, exclusion, and slights. But the more you practice showing up, the more life tends to reward you.
Surprised Myself Too
My biggest surprise was realizing I was faster and in better shape than roughly 75% of the players due to playing tennis and pickleball three times a week for over 20 years. But in my mind, I had told myself I wouldn't be able to keep up. Fitness becomes the great equalizer as you age.
When I played four years of 5.0 USTA tennis, most of my opponents were former college players who were far 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 terrible record, but at least I showed up. In contrast, my 4.5 teammate decided to quit after he got bumped to 5.0.
Time Will Run Out For Making Things Right
Windows of opportunity do not remain 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 arrives and you lose your job.
I knew that if I did not try organized basketball at 48, I might never have the chance again. And if I never tried, I would carry that regret to my grave.
Now my goal is to stay fit and keep playing while avoiding injury. I am still wary of twisting my ankle or blowing my achilles, but I will keep showing 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 cost nothing. All I did was show up. Interestingly, this “life regret” almost weighed on me as heavily as financial regrets, such as day trading too aggressively early in my career. Both reflected disappointment in myself for not performing in the right way.
As I move through the second half of my life, I encourage you to list the regrets that still nag at you and resolve them before it is too late. Each time you do, your soul feels lighter.
Personally, I will treasure the feeling of hitting that first game winning three forever. And two weeks later, I even hit a step back bank three from the side to win another game. You never know until you try!
Readers, what life regrets have you addressed, and how? Do your life regrets nag you as much as your financial ones?
Subscribe To Financial Samurai
Pick up a copy of my USA TODAY national bestseller, Millionaire Milestones: Simple Steps to Seven Figures. I’ve distilled over 30 years of financial experience to help you build more wealth than 94% of the population—and break free sooner.
Listen and subscribe to The Financial Samurai podcast on Apple or Spotify. I interview experts in their respective fields and discuss some of the most interesting topics on this site. Please share, rate, and review.
To expedite your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter. You can also get my posts in your e-mail inbox as soon as they come out by signing up here.
