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, Malaysia. My primary goal was simply to fit in and not just nerd out. 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 shy and scared to look like a fool as the new kid.
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 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 ankle brace when I play any sport.
After avoiding it for half a year, a fellow dad named John – 6′ 4″, 235 pounds – asked me to come. I gave my usual excuses about injury risk and looking foolish. It's intimidating to play against much larger people than you. 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. We also sorted the teams to better matchup by size, as I wasn't about to guard another fellow dad, who was 6′ 7″ and 240 pounds.
The main way I could contribute was on defense. Defense, after all, is mostly about effort, while offense requires far 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 that’s when 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. At that moment, I figured what the heck. It was my time to shoot the ball and go for glory. I set my feet and let it fly!
I could not believe it. Like one of those slow motion, out of body experiences when you see the ball float through the air, and then swish! I had knocked down the three to win the game!
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 due to inaction. Some are small, like not trying out for your high school basketball team. Others grow heavy, like not asking someone out or not investing in that hot AI startup when you had the chance.
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. And I didn't want to get mocked at and feel rejected on a Sunday evening.
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 still would have had fun. No one made fun of me, as I had feared. I realized I had been stuck in my own head since high school. As a school parent, I belonged there, even if 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 slights. So we may not speak up or participate as often, thereby losing opportunities due to cultural difference. 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.
Get your mind right by believing in yourself. If you don't believe in yourself, then you've already lost.
Time Will Run Out For Making Things Right
Windows of opportunity close faster than you think. You only have so much time with your kids before they’d rather hang out with friends. You only have so long to build wealth before the next bear market hits or a job disappears. And eventually, you’ll be too old to tackle the slippery Manoa Falls trail, let alone the Inca Trail.
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.
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 you 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?
A Conversation With 4X NBA Champ, Shaun Livingston
Given my love of 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.
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Awesome story! I used to be a big basketball fan, but hated MJ (though I respected him). I was a NY Knicks fan so he broke our hearts. I have a similar memory but in HS when there was an intramural league. I was a quiet freshman who hit a winning free throw to make it to the championship game. The next year, they scrapped the intramural league and started a boy’s team. I went to the tryout but walked out because I was scared and saw the competition. My favorite t-shirt at the time from “No Fear” said, Never let your fears get in the way of your dreams” It was also the quote on my yearbook. I wanted to believe it but I often let fear get in the way of my dreams. I loved your story of redemption!
Time to join the YMCA or a local pick up league!
No Fear! Just stretch a lot and warm up at least 15 minutes before hand. Gotta do it as middle-aged guys now.
I am so proud of you for doing the thing! The thing you’ve wanted to do for so long! Somehow we are all still a little kids stuck in our own minds aren’t we? I absolutely love your column but today I feel like a proud mama also. Congratulations, you are really living life well!! have the best time in Hawaii
Great positive post!
Yup, MJ is the GOAT and I’m shocked there is even a conversation around this! The kids don’t know, if only they coulda seen him playing those WGN games where his normal game is like a highlight reel.
Glad to hear you got back on the court! I’m a bit nervous to lace them up again for fear of injury…but now you have me thinking about it.
Give it a go and take it easy!
great post.
Great story and great job getting out there! I very much respect your initial fear. As you point out, I’d say 90% of rec level adult sports is fitness. I played hockey at a high level my whole life (not pro) and guys who didn’t even play until adulthood could still give me problems if they were in good shape and had good mobility. Skill would take over in the long run, especially once they got just a bit fatigued, but I respect the heck out of them nonetheless. Further, having the rec sports to look forward to is a huge social outlet for men and can keep you motivated in the gym. It’s easy to identify fitness weaknesses during sports such as backward or lateral movement, upper body strength or just stamina. As a side note, I think your sport of tennis is probably the best cross training sport there is and the attributes needed apply to many other sports, especially basketball (footwork). I’m having my soccer player daughters play tennis for the cross training aspect as well as the social aspect for adulthood.
The social aspect really is a nice bonus. Fun to meet different types of dads I wouldn’t have otherwise met.
That’s great you’re still playing hockey! I’ve always admired a found intriguing those of you who were able to play at a high level (eg colege), and the psychology behind playing those who didn’t later on in life.
A lot of the people I know who played tennis in college didn’t want to play UsTA tennis anymore. To lose to a non-college player would be too bothersome. Only downside if they compete again, unless they love the game.
Great story Sam! Glad you conquered a lingering regret. I’m 59 now, but your story reminds me of when I moved to Santa Barbara in my late 20s. I was a huge football fan, and though I never played organization ball, I played for years in the sandlot leagues with friends. I ended up joining an adult flag football league and played for 3 or 4 season into my early 30s. Most of the guys were former high school stars reliving their glory years and they were pretty dang good. A couple of guys were current college players, and they were phenomenal; actually unstoppable. But I learned a few techniques from these players and improved my game.I was likely the oldest player on the field playing against guys 10 years younger than me with league experience. I was assigned to the second worst team in the league (the worst team was a bunch of stoners that smoked weed before the game…lol) and we only won a couple of games each year, but I had a blast! It was like golf. You suffer through a miserable game and somehow you end up with a PGA grade putt for birdie that keeps you coming back!. There was the occasional game that I managed a pick six, or the time that only 4 guys showed up on our 8-man team (which was a forfeit) but we told the other team we wanted to play anyway. I played QB, but what the other team didn’t know was I played sandlot QB for more than a decade and had a nice finesse to my west coast offence passing game. A couple of touchdown passes later and we made it competitive. Good times! Glad you drained that 3 pointer for the win!
Haha, awesome! That sounds like so much fun. All the cool kids at my high school played football, and that is another sport. I also didn’t have the guts to play. But I grew up overseas for 14 years and we didn’t play American football in Japan, Malaysia, Taiwan or the Philippines.
I’m sure Beating the young guns in a couple of those games I was extremely satisfying. Maybe nothing more satisfying, right?
And I’m sure the young guys reliving their glory days was also equally satisfying to them. To be able to maneuver, the older and slower folks must’ve felt so fun for them.
Good for you, Sam! As a fellow late 40’s guy who’s always had a love for basketball, I too started going to open gym, but with my to be teenage boys. We’ve been playing together for 2 years now (2 dad’s and 3 kids per team) and run full court. Being able to help guide the kids playing up with adults and seeing their growth has been such a joy and blessing. And yeah…the dad’s get in a few plays here and there while getting some good exercise. To your point, as we get older, consistently working out and staying fit is the biggest differentiator and is the prerequisite to being in the position to show up. As we head into the new year, I would encourage all the fellow Samurai’s to step into the game of working out consistently in 2026! Keep up the great work, Sam!
What a great father son activity to do. I’m sure looking back, your kids, and you will think fondly of the times you practiced and played together. I think Golf might be another really nice activity, which I haven’t introduced my kids to yet.
May the Fitness God’s bless us and the injury demons stay away!
Good afternoon,
I completely agree with you, the window is small so move forward. I didn’t want to put my name in the comments of the article, but I have had a very similar experience recently.
When I graduated college 41 years ago, I wanted to do 3 things with my time and money. Learn to scuba dive, parachute and learn to fly a plane. I did the first 2 immediately after graduation but didn’t have the discretionary dollars to fly. I was married and traveling and then kids who needed me to be a stable provider and not taking unnecessary risks, then I retired at 57 and started doing paid Board and Advisory work. This past year at 63 I decided it was time to earn my wings. It has been an amazing experience even though I am about 40 yrs later than I thought it might be. It is still one heck of a fun time. I did my solo flight next week and should have my license in 1 month or 2.
I am a lifelong learner, and this has truly been a wonderful experience. My instructor tells me that I have been a fantastic student; diligent and serious about learning the whole process. So I guess we should live our dreams and take the opportunity to expand our windows of learning any chance we get. I have always challenged myself to be better, to learn and to stay relevant. This is one more step in that process.
Have a very good new year.
PS
So awesome! Thank you for sharing. Better late than never, of course. No regrets!
I really enjoyed this article. Thank You for sharing. As a 61 year old male, it hits hard. I have many regrets from High School. However, I have learned to tell myself, “we learn and grow” from every difficult situation. Thanks again!
That’s great you’ve been able to play basketball. Sounds like a lot of fun.
When I was younger I had an enormous bucket list and so many things I had fomo about and felt I had to do. Interestingly enough my bucket list is like a fraction of the size now. Maybe it’s also because I’m in a very hectic period of my life with so many responsibilities that I don’t have mental bandwidth to daydream about things anymore. Or it could just be that my interests and priorities have shifted a lot.
In any case, it’s great to be able to fulfill dreams when opportunities arise and also adapt our wish lists as we change and evolve as people over time.
Thanks Sam for the article. I’m long time reader. You inspired me to get back on the court. I’m a dad with a toddler, and a basketball fan. Hearing your story reminded me to restart playing bball and not live with regret. Cheers and happy holidays!
Great to hear! And don’t forget to stretch and do some warmups first!
My physical trainer friend tells me that she sees so many “weekend warriors“ who don’t do anything physical during the week (just desk work) and then go out and play pickle ball and stuff on the weekend and then get hurt.
Have fun!