When Winning Isn’t Winning,
In Youth Sports or In Life
This past weekend, I had one of those parenting moments that sticks with you. Not because it was heartwarming, but because it revealed something deeper about how we raise kids and how that echoes all the way into adulthood.
My daughter plays fourth-grade lacrosse. At this level, the rules are simple and intentional: no stick checking, and teams must make two passes before they can shoot. The idea isn’t to win at all costs. The idea is to teach these 9- and 10-year-old girls how to actually play the game. Cradle. Pass. Catch. Communicate. Learn the fundamentals
The score doesn’t matter. The growth does.
But this weekend, we played a neighboring town, and their coach had a very different philosophy.
Instead of encouraging his players to run offensive sets or work on clean passes, his “strategy” was for two girls to literally drop the ball into each other’s sticks twice, technically meeting the two-pass requirement and then hand it off to their best player to go score.
That was it. Over and over again. No team play. No development. Just a shortcut to a scoreboard that, let’s be honest, nobody is even really tracking.
It wasn’t just lazy coaching. It was a missed opportunity, and it sent a message to those young girls: We don’t trust you to try. We don’t think you’re capable. Just do the bare minimum and let someone else carry the team.
And that message? It doesn’t stay on the field.
The Long Shadow of Bad Coaching
Youth sports, when done right, teach us the fundamentals of life. They teach us to try, to fall, to get back up. To communicate. To lose with grace. To win with humility. And to believe that effort and not shortcuts build real success.
But when a coach decides that winning is more important than teaching, they rob kids of those lessons. They replace growth with fear. And whether we realize it or not, that kind of coaching plants a seed of insecurity that grows up right alongside us.
Because if your coach didn’t have enough faith in you to try, and if the parents around you didn’t push back on that, what is the message we are sending our young daughters?
You start to believe that trying isn’t worth it unless you’re guaranteed to win.
You learn to play it safe. You learn to defer. You learn to stay quiet and let someone else take the shot.
And Then You Become an Adult…
Fast forward 20 years, and that same kid is now an adult who’s terrified of asking financial questions. Not because they’re lazy or disinterested, but because they’ve been trained to believe that asking for help means they’re losing at life.
They sit in meetings, nodding along, pretending they understand what an “RMD” is or how their taxes really work all because somewhere along the way, they were taught that not knowing something is shameful. That asking for help is weak. That someone else is better equipped to “score.”
I see it all the time in financial planning. Adults who feel behind. Who are scared to admit what they don’t know. Those who have been handed off to their own version of the “best player” an advisor who talks over them, sells them something shiny, and tells them not to worry about the rest.
That’s not a strategy. That’s dropping the ball into someone else’s stick and hoping for the best.
Financial Confidence Is Built the Same Way We Teach Lacrosse
Here’s the truth: financial planning isn’t about “winning.” There is no scoreboard. There’s no one right path.
What it is about is learning the fundamentals.
- Making intentional choices
- Asking the hard questions
- Understanding what you’re doing and why
- Being willing to drop the ball and scoop it back up
- Passing with purpose — not panic
- And believing that you are capable of playing this game
You don’t need to know everything. You just need a coach who believes in teaching — not winning on your behalf.
Parents: We Have to Do Better
As parents, it’s our job to call out bad coaching. Not because we care about a Saturday morning lacrosse score but because we care about the messages our kids are internalizing.
A coach who doesn’t let your child try is teaching them that effort isn’t worth it. That it’s safer to step aside. And that mindset doesn’t just impact their relationship with sports, but it shapes how they show up in school, in friendships, in work, in money, in everything.
We should be outraged when a coach cares more about their own “win” than our child’s growth. Because long after the game is over, the consequences of that mindset stay with them.
And in our adult lives, we should be just as frustrated when we see the same thing; advisors, bosses, or leaders who want to win for you, instead of with you.
Let’s Play the Long Game
I don’t know what the score was in that lacrosse game, and I couldn’t care less. What I care about is that my daughter made real passes, hustled for ground balls, and walked off the field a better player than she was the week before.
She’s learning the game and that’s the win!
And that’s the same win I want for every client I work with. Financial planning isn’t about being perfect or pretending to know it all. It’s about building confidence. Asking questions. Learning the plays. And finding someone who believes in your ability to figure it out.
Whether it’s lacrosse or life, the goal isn’t to look like you’re winning.
It’s to actually grow.
Stock market calendar this week:
| Time (ET) | Report |
| MONDAY, MAY 5 | |
| 9:45 AM | S&P final U.S. services PMI |
| 10:00 AM | ISM services |
| TUESDAY, MAY 6 | |
| 8:30 AM | U.S. trade deficit |
| WEDNESDAY, MAY 7 | |
| 2:00 PM | FOMC meeting |
| 2:30 PM | Fed Chair Powell press conference |
| 3:00 PM | Consumer credit |
| THURSDAY, MAY 8 | |
| 8:30 AM | Initial jobless claims |
| 8:30 AM | U.S. productivity |
| 10:00 AM | Wholesale inventories |
| FRIDAY, MAY 9 | |
| 5:55 AM | Fed Governor Michael Barr speech |
| 6:15 AM | New York Fed President John Williams speech |
| 6:45 AM | Fed Governor Adriana Kugler speech |
| 8:30 AM | Richmond Fed President Tom Barkin speech |
| 10:00 AM | Chicago Fed President Austan Goolsbee speech |
| 11:30 AM | Fed Governor Christopher Waller and New York Fed President John Williams on panel |
| 6:45 AM | Fed Governor Lisa Cook speech |
| 7:45 PM | Fed Governor Bowman, St. Louis Fed President Alberto Musalem and Fed Cleveland Fed President Beth Hammack on panel |
Most anticipated earnings for this week
Did you miss our last blog?
Why Market Volatility is a Crucial Opportunity for Couples to Strengthen Their Financial Connection
About Amit: I am a first generation American, the son of a working-class Indian family, and I lived through my parents’ struggle to find their place in this country, to put down roots that would sustain them as well as their children in a new land. As they encouraged me to excel in school and fostered my hobbies and interests, I was keenly aware of the dynamic between them. I understood that there was a difference between where they came from individually and where we were now. They worked hard in their individual capacities, but they weren’t always on the same page about financial issues – and that can make or break a family’s future. I didn’t know it at the time, but this laid the groundwork for my passion towards financial services and helping families succeed.