We often tell ourselves that childhood dreams are meant to fade. They are relics of a simpler time, outgrown like old shoes. But what if that lingering ache isn't nostalgia, but a roadmap?
That realization hit me while watching my children tear through their Christmas presents. I saw the fleeting joy of a long-awaited toy and felt a sudden melancholy. It forced me to confront a regret I had carried for thirty-three years: never trying out for my high school basketball team.
The Weight of Inaction
Regret rarely stems from the mistakes we make; it festers in the opportunities we let pass by. Back in high school, I was the new kid, having just moved from Kuala Lumpur to Northern Virginia. My goal was simple: fit in. I made the varsity tennis team, but when basketball season arrived, I froze.
I had told my P.E. teacher I aimed to make the team. She believed in me. I believed in me. But when tryouts came, my shyness won. I was terrified of looking foolish as the new kid. It is a fear that many people, especially minorities and those from different backgrounds, know intimately: the fear of ridicule and exclusion that keeps us silent.
Basketball had been my obsession since sixth grade. Michael Jordan was my hero. My family couldn't afford his sneakers, but a friend 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, a quiet ghost haunting my sense of self-worth.
Showing Up Is Half the Battle
Decades later, I heard about a Sunday night open run at my children's school gym. It was free, but I avoided it for six months. My excuses piled up: the risk of injury, the intimidation of playing against larger men, the shame of being the worst player there.
My left ankle has been sprained over twenty-five times. I wear a brace for everything. I had watched dads blow out ACLs. But then a fellow dad, a towering 6'4" man, asked me directly to come. He waved off my fears.
When I finally walked into that gym, I was surprised. The pace was intense, and the players were younger than I expected. I realized immediately that if I didn't adapt, I would fail. I decided to embrace my inner Draymond Green. At 5'10", 168 pounds, I was small, but I focused entirely on defense and effort.
Psychological research on the "belongingness hypothesis" suggests that humans have a fundamental need to belong to a group (Baumeister & Leary, 1995). By simply showing up, I was fulfilling that need, dismantling the isolation I had built around my fear.
The Moment of Truth
Defense is mostly about effort; offense requires skill I hadn't honed in years. I held two players scoreless. I set screens. I moved the ball. We started winning. And then, the moment arrived.
The best player on my team drove to the basket and kicked the ball out to me at the top of the key. I hesitated for a split second--old habits die hard--then I thought, what the heck. I set my feet and let it fly.
It was a slow-motion out-of-body experience. The ball floated, rotated, and dropped straight through the net. A swish. I had knocked down the three to win the game. The feeling was euphoric, a rush of dopamine and validation that I hadn't felt in years. It wasn't just a basket; it was the closure of a three-decade-old wound.
Fitness: The Great Equalizer
The biggest surprise wasn't the shot; it was my stamina. I realized I was faster than 75% of the players. For twenty years, I have played tennis and pickleball three times a week. In my mind, I had told myself I was too old and too slow. But fitness becomes the great equalizer as we age.
I once watched a college teammate play at William & Mary, thinking I was worlds apart from him. Twenty-three years later, I found myself on a court with him again. I had a terrible record that day, but I showed up. My 4.5 tennis teammate, in contrast, quit after he got bumped to 5.0. He couldn't handle the new level. The difference between us wasn't skill; it was the willingness to stay in the arena.
As noted by sports psychologists, self-efficacy--the belief in one's ability to succeed--is the strongest predictor of performance (Bandura, 1997). If you don't believe you can keep up, you've already lost before you start.
Closing Other Regrets
This experience taught me that eliminating regret is a transferable skill. The act of showing up applies to every area of life where fear holds us back.
Consider the fear of public speaking. Many people avoid Toastmasters or networking events because they fear stumbling over their words. But just like the basketball court, the room is usually supportive. The regret of silence often hurts more than the momentary embarrassment of a mistake.
Another common regret is avoiding a physical challenge, like running a marathon. I met a man who put off training for years because he was afraid he wouldn't finish. He finally signed up for a 10k, not a marathon. He didn't win, but the act of training and crossing the finish line eliminated a decade of "what ifs."
These examples mirror financial regrets. Just as I avoided the basketball court, many people avoid looking at their investment portfolios during a bear market. The avoidance creates more anxiety than the reality. Eliminated regret fulfilled childhood dreams are often just a single decision away.
The Ticking Clock
Windows of opportunity close faster than we think. You only have so much time with your kids before they prefer their friends. You only have so long to build wealth before the next economic shift. And eventually, you will be too old to jump for a rebound.
I knew that if I didn't try organized basketball at 48, I might never have the chance again. The physical requirements of the game are unforgiving. By addressing this now, I eliminated regret fulfilled childhood aspirations before time ran out.
Now, my goal is simple: stay fit, play, and avoid injury. I am still wary of twisting my ankle, but the joy of the game outweighs the fear of the sprain. This mindset shift is crucial for long-term happiness. When you actively eliminated regret fulfilled childhood goals, you create a positive feedback loop that encourages you to tackle bigger challenges.
Life Regrets and Money Regrets
Solving this 33-year regret cost nothing but time and courage. Interestingly, this life regret weighed on me as heavily as financial regrets, such as day trading too aggressively early in my career. Both reflected a disappointment in myself for not performing in the right way.
Financial Samurai often writes about the importance of taking calculated risks. Whether it's investing in the market or investing in yourself by showing up to a tryout, the principle is the same. You must play the game to win.
As you move through the second half of your life, I encourage you to list the nagging regrets and resolve them. Each time you do, your soul feels lighter. The goal isn't to become an NBA star; it is to eliminated regret fulfilled childhood memories so you can move forward unburdened.
Two weeks after that first game-winner, I hit a step-back bank three from the side to win another game. You never know what you are capable of until you try. The biggest barrier to eliminated regret fulfilled childhood dreams is often just the front door of the gym. Walk through it, and the rest takes care of itself.
