By Bobby Garon
Managing risk is something I think about constantly in my work as a finance and insurance professional here in Naples, Florida, but some of the clearest lessons on the subject have come from a golf course, not a spreadsheet. I’ve spent a good amount of time on courses around Southwest Florida over the years, and the more I play, the more I notice how closely the game mirrors the decisions I help clients make every week.
Every Golf Shot Is a Risk Management Decision
Golf forces you to make a risk decision on nearly every shot. Do you go for the green over the water, or lay up short and take the safer approach on your next stroke. Do you pull driver on a tight fairway, or hit something more controlled off the tee. None of these choices are about talent alone. They’re about how much risk you’re willing to accept for a potential reward, and whether that risk fits the situation you’re in.
I see the same pattern with clients constantly. Someone wants to chase a higher return without stopping to ask whether their coverage or savings can absorb a bad outcome. Golf makes that tradeoff visible in a way a financial statement rarely does, because you watch the consequences play out in real time, shot after shot.
Playing the Course, Not the Pin: A Lesson in Financial Planning
One of the better pieces of advice I’ve heard on a golf course is to play the course, not the pin. Chasing a flag tucked behind a bunker might look tempting, but a good player reads the whole hole first, the wind, the lie, the trouble lurking on either side, before deciding where to aim.
Financial planning works the same way. I wrote more about how budgeting and financial planning depend on the same kind of consistency, and the same principle applies here. A single aggressive move might look appealing in isolation, but a good plan accounts for the whole picture first, income, obligations, timeline, before deciding how much risk makes sense.
Insurance as the Layup: Managing Risk Without the Hero Shot
If there’s one place golf and insurance line up most closely, it’s here. A layup isn’t exciting. It won’t get mentioned after the round. But it protects your score from a disaster that a riskier shot could have caused.
Insurance is a lot the same. It’s rarely the exciting part of a financial plan, and most people would rather not think about it at all. But I laid out the fundamentals in Insurance Basics Everyone Should Understand, because understanding your coverage before you need it is the financial version of choosing the safer shot when the smarter play calls for it. Nobody regrets the layup after it saves their round.
Golf Handicaps and Honest Risk Assessment
A golf handicap exists because honest self-assessment matters. You can’t play smart risk decisions on the course if you’re pretending your game is better than it is. The same goes for money. A financial plan built on an inflated sense of what you can absorb if something goes wrong is a plan waiting to break.
This ties into something I explored in why community matters so much in raising a family. A support system, whether it’s a group of golf buddies who’ll tell you your swing looks off, or a network of people who help carry you through a hard financial season, tends to keep people honest about where they really stand. Managing risk well usually depends on having people around who’ll tell you the truth.
The Nineteenth Hole Conversations
Some of the most honest business conversations I’ve had happened after a round, not during a meeting. There’s something about spending four hours outside with someone, watching how they handle a bad shot or a good one, that tells you more about how they make decisions than a formal pitch ever could.
I think this connects to something I’ve written about banking too. In Banking Basics Everyone Should Understand, I talked about how much of good financial guidance comes down to an actual relationship, not just a transaction. Golf just happens to be one of the more natural settings where that relationship gets built. I got to expand on that idea more personally in a recent interview with VoyageMIA, where we talked more broadly about how I try to show up for people, on the course and off it.
Key Takeaways: Managing Risk On and Off the Course
Managing risk, whether on a golf course or in a financial plan, comes down to the same handful of habits. Know your actual position before you commit to a decision. Choose the safer shot when the smarter play calls for it. Surround yourself with people who’ll be honest with you about how things really look. None of it requires being an expert. It requires paying attention and being willing to lay up when a hero shot isn’t worth the risk.
If there’s one thing I’d want someone to take away from a round with me, it’s that managing risk well isn’t about avoiding it altogether. It’s about knowing which risks are worth taking and which ones deserve the safer play, on the course and everywhere else.
About Bobby Garon
Bobby Garon is a finance and insurance professional based in Naples, Florida, where he lives with his wife and son. He writes about financial education, leadership, personal growth, family, and community involvement. You can find more of his writing at bobbygaron.com.
Frequently Asked Questions about Managing Risk
What can golf teach someone about managing risk?
Golf forces a risk decision on nearly every shot, whether to play it safe or go for a riskier reward. That same tradeoff shows up in financial decisions, and golf makes the consequences visible in a way a spreadsheet usually doesn’t.
Why does Bobby Garon compare insurance to a layup?
Bobby Garon finds a layup isn’t exciting, but it protects your score from a bigger mistake. Insurance works the same way. It’s rarely the exciting part of a financial plan, but it protects the progress you’ve already made.
How does honesty about your own limits factor into managing risk?
A golf handicap only works if it’s honest. The same goes for financial planning. Overestimating what you can absorb if something goes wrong leads to decisions that don’t hold up under pressure.
Why does Bobby Garon mention having business conversations on the golf course?
Spending hours with someone outside a formal meeting reveals how they handle pressure and setbacks, which tells you more about trustworthiness than a pitch ever could.
What’s the main takeaway from comparing golf to financial risk?
Managing risk isn’t about avoiding it entirely. It’s about knowing which risks are worth taking and choosing the safer path when the smarter play calls for it.
