As I watched my children tear up their Christmas presents, I felt an unexpected pang of melancholy. I knew the excitement over that one toy they had wanted for so long would be fleeting. Soon it would be replaced by the next obsession. Having children can pull you back in time, forcing you to think about your own childhood and the regrets that still linger.
One of my biggest regrets was never playing for my high school basketball team.
I was the rookie at McLean High School in Northern Virginia, having just moved from Kuala Lumpur, Malaysia. My main goal was to just fit in and not just be left out. I made the varsity tennis team as a freshman, but when basketball season came, I froze.
I had told my gym 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 shy and afraid to look like a fool as the new kid.
Basketball was my obsession since sixth grade in Malaysia. Michael Jordan was my hero, the undisputed GOAT, and I wanted every pair of his shoes. My family couldn’t afford them, so my great friend Todd gave me his hand-me-down Jordan 5s, two sizes too big. I looked ridiculous walking around in them, but to me they were magical.
That regret stayed with me for thirty-three years. Until now.
Finally got my shot off
Every Sunday evening at my children’s school there is an open basketball run in the new gym. It is free for fathers, friends of fathers and staff. When I first heard about it, I was intrigued but also nervous. I knew that fathers had had their ACLs blown out, and that my own left ankle had been sprained more than twenty-five times. I always wear an ankle brace when exercising.
After avoiding it for six months, a fellow dad named John — 6-foot-4, 235 pounds — asked me to come. I gave my usual excuses about the risk of injury and looked foolish. It’s intimidating to play against people much bigger than you. He waved it away and said I would fit in just fine.
When I finally showed up, I was surprised. About 70% of the players were under 35 years old, and almost half were under 30 years old. The pace was much more intense than I expected.
Since I hadn’t practiced in over a decade, I focused on defense. At 6-foot-4 and 168 pounds, I was on the small side, but I embraced my inner Draymond Green and locked in. We also sorted the teams to better match for size, since I wasn’t about to guard another fellow dad who was 6-foot-4 and 240 pounds.
The main way I was able to contribute was on defense. After all, defense is mainly about effort, while attack requires much more skill. I held two players scoreless in two separate games. I then focused on identifying the best scorers, setting screens, and moving the ball to open teammates. We won the first game, and then I realized I could hang around.
Received a great gift
In the last game, the best player on my team drove to the basket and kicked the ball out to me at the top of the key. At that moment I thought, what the heck. It was my time to shoot the ball and go for glory. I put my feet down and let it fly!
I couldn’t believe it. Like one of those slow-motion, out-of-body experiences where you see the ball floating through the air, and then it swooshes! I had defeated the three to win the game!
It was one of the best feelings I’ve had in a long time. I would put it right at the top when negotiating my layoff 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, the regrets pile up because you don’t do anything. Some are small, like not trying out for your high school basketball team. Others get tough, like not asking someone out or not investing in that great AI startup when you had the chance.
My biggest fear when playing was injury, followed by the feeling that I didn’t belong. If I got hurt, I wouldn’t be able to play with my kids, which would be horrible and would be a burden on my wife. And I didn’t want to be mocked and feel rejected on a Sunday night.
But showing up changed everything. I met the organizer, an eighth grade teacher and guidance counselor who helps with high school applications. I met four other dads that I really like. And I finally let go of the regrets I had been carrying for over thirty years.
Even if I had played terribly, I still would have had fun. No one made fun of me, as I had feared. I realized that I had been in my own head since high school. As a school parent, I belonged there, even though I once thought otherwise.
Not feeling like you belong is a common experience, perhaps even more so for minorities and foreigners. We fear ridicule, criticism, exclusion and contempt. So we may not speak up or participate as often, missing out on opportunities due to cultural differences. But the more you practice showing up, the more life will reward you.
Surprised myself too
My biggest surprise was that I was faster and in better shape than about 75% of the players, having played tennis and pickleball three times a week for over twenty years. But in my mind I told myself I wouldn’t be able to keep it up. Fitness becomes the great equalizer as you get older.
When I played 5.0 USTA tennis for four years, most of my opponents were former college players who were much more skilled, but my fitness allowed me to compete. I even saw one of my teammates play for William & Mary while I was there, only to be on the same field with him 23 years later.
I had a terrible record, but at least I showed up. My 4.5 teammate, on the other hand, decided to quit after being bumped to 5.0.
Get your mind right by believing in yourself. If you don’t believe in yourself, you’ve already lost.
Time will run out to put things right
Windows of opportunity are closing faster than you think. You only have so much time with your kids before they prefer hanging out with friends. You only have a limited time to build wealth before the next bear market hits or a job disappears. And eventually you’ll be too old to hike the slippery Manoa Falls trail, let alone the Inca Trail.
I knew that if I didn’t try organized basketball at age 48, I might never get the opportunity again. And if I never tried, I would take that regret to my grave.
Now my goal is to stay fit and keep playing while avoiding injuries. I’m still wary of twisting my ankle or blowing my Achilles tendon, but I will continue to show up as long as my body is healthy.
Life regrets and money regrets are surprisingly similar
Resolving this 33-year regret cost nothing. All I did was show up. Interestingly enough, these “life regrets” weighed on me almost as much as financial regrets, such as day trading too aggressively early in my career. Both reflected disappointment in myself for not performing appropriately.
As you move through the second half of my life, I encourage you to identify the regrets that still haunt you and resolve them before it is too late. Every time you do that, your soul feels lighter.
Personally, I will cherish the feeling that I won that first game forever by winning three. And two weeks later I even stepped back on bench three from the side to win another game. You never know until you try!
Readers, what life problems have you tackled, and how? Does your life nag as many regrets as your financial ones?
A conversation with 4X NBA Champion Shaun Livingston
Given my love for basketball, I was thrilled to speak with NBA champion Shaun Livingston about his journey from high school standout to four-time NBA champion with the Golden State Warriors. My, how time flies.
Subscribe to Financial Samurai
Pick up a copy of my national bestseller USA TODAY, Millionaire Milestones: Easy Steps to Seven Figures. I’ve distilled more than 30 years of financial experience to help you build more wealth than 94% of the population – and get unstuck faster.
To accelerate your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter. You can also receive my posts in your email inbox as they arrive sign up here.
#regret #eliminated #childhood #dream #fulfilled #free