What Golf Taught Me About Business and Investing

Sports can teach us so much about life. And if you have kids, I’d encourage you to get them involved early – whether in team sports or individual ones. The lessons you pick up at a young age carry into everything else, including business and investing.

Pulickel Prasad wrote a wonderful book called What I Learned from Darwin About Investing. It made me wonder what I’ve learned from the beautiful game of golf. Over the years, golf has quietly become one of my greatest teachers – not just in patience and focus, but in business, investing, and how I approach life itself.

The Psychology of the Game

Even if you’ve never played, you’ve probably come across studies that use golf to explain human behavior. In Thinking, Fast and Slow, Daniel Kahneman found that professional golfers are more likely to sink a par putt than a birdie putt from the same distance. Why? Loss aversion. We fight harder to avoid a bogey – a loss – than to chase the gain of a birdie. It’s the same instinct that makes investors cling to losing stocks longer than they should.

Bob Rotella’s Golf Is Not a Game of Perfect teaches that success in golf is mostly mental – confidence, resilience, and the ability to forget your last bad shot. Investors need that same discipline when markets get volatile. And Timothy Gallwey’s The Inner Game of Golf takes it one step further – the biggest battle isn’t with the course, but with yourself. Business, investing and entrepreneurship are no different.

A Little Context

I’ve been a member at Ken-Wo Golf Club for over two decades, serving as treasurer for the past ten years. That role has given me a front-row seat to budgeting, capital allocation, and leadership – concepts that translate directly to business and investing.

When I first started tracking my handicap in my late twenties, I was a 12. Today, I hover around a 4 today. If you’re wondering what that means, think of a handicap as the great equalizer – it adjusts scores so golfers of different abilities can compete fairly. The average male golfer in North America has a 14 handicap, and statistically, players only shoot their handicap about one in every five rounds.

That alone says something about life and investing: even when you know what you’re capable of, it’s rare to perform at your very best.

What Golf Taught Me About Business

Golf and business share one thing in common – they both demand patience and reward persistence. Both are wonderful, challenging, and occasionally nerve-racking.

Rebuilding to Move Forward

Golf will test you. There are times you grind, times you experiment, and times you throw mud at the wall to see what sticks. Maybe you add a new club, change your grip, or even rebuild your swing entirely. Anyone who’s done it knows the truth – it takes serious commitment, and before you get better, you usually get worse.

That’s exactly how business feels. Sometimes you have to strip things down to the studs, rebuild your foundation, and put in the time before you come out stronger. We lived that firsthand. Our accounting firm grew from six people to thirty-one, and everything that once worked started to break down. To scale, we had to let go of old habits, get clear on our vision, and rebuild with stronger systems. The short-term regression was real – but sometimes you have to get worse before you can get better.

Discipline, Focus, and Execution

Competition is brutal – on the course and in business. You can’t quit when things get hard. I often come back to The Founder’s Mentality by Chris Zook and James Allen. They describe three traits that sustain growth: an insurgent mission, a frontline obsession, and an owner’s mindset. Those same traits make great golfers. Passion, focus, and accountability are what separate those who play the game from those who master it.

Process Over Outcome

You can do everything right in golf – pick the right club, make a perfect swing – and still watch the ball hit a sprinkler head and bounce out of bounds. You can do everything right in business too – hire well, plan carefully, execute with precision – and still fall short. That’s why outcomes don’t always tell the full story.

What truly creates winners is process – the discipline to refine it and stick with it over time. The golfers who consistently shoot low scores aren’t relying on luck; they’re executing routines with precision. The same is true for business leaders who build lasting companies.

Playing and Working with the Right People

Golf might be called an individual sport, but it’s a lot more fun when you play with the right people. The same is true in business. If you regularly play with golfers who don’t putt out and give themselves every three-footer, that attitude eventually creeps into your own game. In business, if you surround yourself with people who cut corners, those shortcuts eventually cost you.

But when you play – or work – with people who hold high standards, you naturally elevate your own. In golf, as in business, the people beside you shape your performance.

And when you get it right – playing golf with friends on a sunny day or working alongside colleagues who share your vision – there’s no better place to be. Both games are about progress, connection, and the joy of playing them well.

What Golf Taught Me About Investing

The first parallel between golf and investing is track record. In investing, we talk about goals, compound annual growth rate, and benchmarks – but the one thing that can’t be rushed is time. You don’t become a great investor after a couple of good years, just like you don’t become a great golfer after one good season.

The results that matter are the ones sustained over decades.

Cost-Benefit and Effort

If you manage your own money, your baseline is the long-term market return – around 9% before fees. We all dream of compounding like Buffett at 20%, but that kind of performance requires decades of discipline and obsession. I remember Stig (host on We Study Billionaires) once asking Mohnish Pabrai if he’d take a guaranteed 15% IRR for 30 years. He said yes – and joked that he’d quit investing and just play bridge. Fifteen percent compounded for 30 years is hall-of-fame territory. It shows that sometimes good enough is great enough.

Golf has taught me that lesson too. I’m a 4-handicap. Could I get to scratch? Probably – if I practiced more and played more. But at what cost? I’d be giving up time with family, friends, and other passions. The same is true in investing. At some point, you hit the law of diminishing returns. The goal isn’t perfection – it’s balance, process, and sustainability.

Risk-Taking

I remember standing on the 18th tee at my home course, even par, with the chance to break par for the first time. I pulled my drive left into the rough. The ball was sitting down, debris everywhere, and a pond guarding the left side of the green. Do I go for it – the risky shot – or do I chip out, hit the green, and give myself a chance to one-putt for par?

That moment felt exactly like investing. Do you chase the big win or protect what you’ve built? Sometimes the hero shot works and you’re celebrated for brilliance. Other times, it sinks you. The key in both golf and investing is judgment – knowing when the risk aligns with your goals and when it doesn’t.

Stasis and Evolution

In golf, stasis often shows up in your handicap. If you play regularly but don’t practice, you’ll probably stay where you are. That’s not all bad – it means consistency – but it also means you’re not improving. Even Tiger Woods, at the top of his game, tore down and rebuilt his swing multiple times.

In investing, though, stasis is dangerous. Markets evolve, and if you don’t evolve with them, you fall behind. Adam Seessel captured this well in Where the Money Is. He realized his old valuation methods didn’t explain modern tech companies that reinvested through the income statement. By adapting, he improved his process – and lowered his “handicap” again.

The lesson? In golf, stasis can be peaceful. In investing, it’s fatal. You need consistency of process but flexibility to evolve when the world changes around you.

The Final Lesson

Charlie Munger once said, “Investing is hard, and if you don’t think it is, you’re stupid.” I’d say the same about golf. Both look simple from the outside – hit the ball in the hole, buy stocks that go up – but they’re humbling in practice. They test your patience, discipline, and decision-making in ways you can’t shortcut.

And that’s why I love both games. They remind me that the goal isn’t perfection – it’s progress. The process is the point.