Your Kid Would Rather Miss Than Look Stupid - The Money Lesson Every Parent Needs to Teach
- Will Rainey
- 6 days ago
- 4 min read
I'm not the biggest basketball fan, so it wasn't until I was listening to a podcast that I learned about the NBA legend Rick Barry.
Rick was one of the best players of his era (late 1960s–1970s). He scored over 25,000 points and won an NBA Championship with the Warriors in 1975, being named Finals MVP.
The really interesting thing about Rick was his record for free throw accuracy (for those who don't follow basketball, a free throw is an uncontested shot from the line, awarded after a foul). He scored over 90% of his free throws, consistently, over many seasons. To put that in context, the best team in the NBA today shoots around 82% from the free throw line, the worst around 74%, and the league average sits at about 78%.
How did Rick do it?
What makes this story even more interesting is how Rick took his free throws. He didn't use the conventional approach of raising the ball to head height and shooting from there. He used an underarm technique, holding the ball between his legs and releasing upward toward the basket.
His underarm approach was so effective that it even convinced another NBA legend, Wilt Chamberlain, to try it. Using the underarm method, Wilt scored a record 28 out of 32 free throws in a single game.
You'd think every NBA player would adopt this approach to improve their numbers. But they didn't. Even Wilt Chamberlain abandoned it after a season.
Why? Because people care what others think.
Players avoided the underarm throw because it looked silly, even unmanly. People called it the "Granny Throw."
Shaquille O'Neal, who was notorious for being a poor free throw shooter, famously told Barry:
"I'd rather shoot 0% than shoot underhand."
Think about that. Some of the most elite athletes in the world were actively choosing to miss more shots, and hurt their teams, because of how they looked taking a free throw. Pride was costing them points on the scoreboard.
When I told my daughters this story, they were as surprised as I was when I first heard it.
3 Money Lessons for Kids using the Underarm Story
This story has a powerful link to how people manage their money. There are plenty of examples where people avoid doing the right thing simply because they worry about what others will think. Let's look at three examples:
1. Spending
This is the most direct parallel to the NBA free throw story. If everyone around you is spending on designer clothes, nice restaurants, and luxury holidays, it's hard to do something different. Simply choosing to save feels like throwing underarm.
Take someone who brings their own lunch to work instead of eating out. The financial logic is obvious, but they often feel judged for it. Most people carry a You Only Live Once (YOLO) mindset: spend now, enjoy now, worry later. It takes real conviction, like Rick Barry stepping to the free throw line, to do the less glamorous thing for a better long-term outcome.
(I want to be clear: I'm not anti-spending, and I encourage my kids to spend. What I want them to avoid is spending everything they have, or spending just to impress others.)
2. Debt
Using credit cards and loans has become so normalised that people are now judged for not using them. Take buying a car. If someone has a few thousand dollars saved, the default assumption is that it's a deposit for a loan, not the full price of a car they can actually afford.
The common argument is that a newer financed car means lower maintenance costs. There's a grain of truth in that, but it's also exactly what car salespeople are trained to say. In reality, buying with debt is likely to cost more, not just in repayments and interest, but in the lifestyle creep that tends to follow (I'd recommend reading my blog on the Diderot Effect for more on this).
Buying a car with cash is the underarm throw. Most people won't do it. But it works.
3. Investing
This one I feel most strongly about. The evidence is clear: investing in a low-cost global stock market fund on a monthly basis, and tuning out the noise, is one of the most reliable ways to grow wealth over the long term. The problem? It's too simple. Too boring. And when everyone around you seems to be doing something more exciting, boring feels hard to justify.
I remember when NFTs (Non-Fungible Tokens) took off in 2021. People were convinced they were the future of investing and couldn't understand why I wasn't joining in. My steady stock market fund approach was mocked, theirs were outperforming everything. It didn't last long. NFT values collapsed, and those same people went quiet. Crypto followed a similar pattern for many investors: thrilling on the way up, painful on the way down, and underperforming the "boring" approach over the long term.
The underarm throw of investing isn't exciting. It won't make you the most interesting person at dinner. But it works.
If you'd like your kids to develop the same mindset, grab them a copy of Grandpa's Fortune Fables. The stories are designed to help them understand more about investing than most adults ever learn.
Give Your Kids a Financial Advantage
There are probably many more underarm equivalents out there. I'd strongly encourage you to share the Rick Barry story with your kids and ask them what they would do. Then talk about how the same principle applies to money, and how choosing the "embarrassing" approach often leads to the best results.
The players who refused to shoot underarm missed free throws they didn't have to miss. Let's make sure our kids don't make the same mistake with their money.
On the theme of avoiding money mistakes, I want to share that my new book, Frankie Fortune, is coming out on 27th July 2026 (save the date). The book follows the misadventures of Frankie which will help your kids avoid many of the money mistakes adults make.
👉 What to read next:
Thanks for reading,
Will
p.s. If you have read Grandpa's Fortune Fables, it would be amazing if you could leave a quick review on Amazon. Thank you in advance for the support!
