What March Madness Can Teach Us About Taking Risks

And how to live and invest like the shot clock matters

When the interns at my office who don’t watch college basketball start voicing strong opinions about why a 12 seed will upset a 5 seed, I know what season we’re in.

March has its own rhythm. Brackets show up in my inbox. The office is quiet on Thursdays and Fridays. By the end of the first weekend, half the country’s predictions are already destroyed.

That’s March Madness.

Every year the NCAA tournament reminds us of something most investors would rather ignore: nobody actually knows how this is going to play out. The best teams lose. Unknown schools make runs. One strange bounce or a half-court prayer can flip an entire season. It’s chaotic by design.

In a strange way, that’s why it feels familiar. Markets run on the same operating system—uncertainty.

But there’s another rule quietly shaping every game that matters even more: the shot clock. Forty seconds. That’s all a team gets to make something happen. Pass too much, hesitate too long, wait for the perfect play, and the buzzer goes off. Possession over.

March Madness is chaos, but the shot clock forces action inside that chaos.

Investing works the same way. Most investors behave as if there is no clock. They wait for perfect information, the right valuation, a cleaner signal from the Fed, a more stable economy, or a moment when the risks feel lower.

That moment rarely comes. Days, weeks, and even years run out like empty possessions until the buzzer eventually sounds.

The uncertainty paradigm

Years ago I started describing the world to clients using what I call the uncertainty paradigm: the future isn’t predictable, but it is navigable. The people who do well don’t try to eliminate uncertainty. Instead, they operate within it.

March Madness is a perfect illustration. If you wait until you know who’s going to win the tournament before filling out your bracket, you’ll never fill out the bracket.

Same with markets. You never get the signal that says, “All risk has been removed. Now would be a perfect time to invest.” Instead, you operate with incomplete information and take intelligent bets, adjusting as you go and taking the shot before the buzzer.

You’ll never fill out your bracket if you wait to see who’s going to win.

Why urgency clarifies things

A shot clock eliminates fake complexity. At the beginning of the clock, players run a system. When there are only a few seconds left, everything simplifies: Get the ball. Create space. Shoot.

With investing, when people act like there’s unlimited time, they overcomplicate everything—entry points, macro forecasts, timing models, endless “what if” scenarios.

When you acknowledge the clock is running, however, priorities quickly become obvious:

Is your capital deployed?
Is it aligned with your plan?
Are you actually participating?

This is why I like the idea of designing your days and weeks like possessions.

Designing days as possessions

Basketball possessions have structure: bringing the ball up the court, initiating action, taking the shot.

Your days—and your investing behavior—should work the same way. Here’s a simple three-step framework you can follow.

1. Start with the play call

Every basketball possession starts with intention, with the team knowing what play they’re running. Most investors start their days the opposite way. They react—to headlines, market moves, notifications, and other people’s opinions.

Get out of that reactive mode by calling a play. Ask one question: What financial decision or action actually matters today?

Maybe it’s rebalancing.
Maybe it’s adding to a position.
Maybe it’s finally putting idle cash to work.

I know this isn’t as easy as it sounds, because while I freely give this advice, I still resist it myself. I like having room in my day to think, write, react. The problem is that flexibility can crowd out the one decision that actually matters.

The key is pace over perfection. Call the shot early and see what happens. Think of it like going to the gym—consistency and letting the reps compound is what matters more than a “perfect” workout.

2. Move the ball with small bets

While heroic moves in basketball are memorable, the vast majority of basketball possessions succeed because of a series of small actions that create space that lead to an opportunity.

With investing, the best outcomes rarely come from one perfectly timed decision. They come from a series of smaller decisions that compound over time. In uncertain markets, that might look like:

Gradually allocating capital instead of waiting for the “perfect entry.”
Increasing exposure in stages.
Rebalancing incrementally instead of making all-or-nothing shifts.

Small bets create options, keep the offense moving, and prevent paralysis. Invest in stages and adjust as new information arrives. Then let time and compounding do the heavy lifting. This is almost always how you work toward progress in the markets—stringing together smart, modest decisions instead of one dramatic call.

3. Take the shot

Here is where most investors fail. The setup is there—cash available, plan in place, opportunities visible—and then nobody wants to pull the trigger.

Why? Because a missed shot feels like failure.

But in markets, not investing is often worse than being imperfectly invested. If you never take the shot, your capital doesn’t grow.

I see this especially during volatility. People hesitate because they wait for stability. They tell themselves they will invest when things calm down.

The problem is they miss their shot. Volatility is often when long-term returns are set up. It’s not about taking reckless risk. It’s about accepting that taking action under uncertainty is part of the game.

A client who needed the shot clock

Years ago I had a client named Ben who illustrated this perfectly. He built a successful business and accumulated a significant amount of cash. He was smart and analytical, but he was too careful. For years, a large portion of his wealth sat on the sidelines. When markets dipped, he was afraid they’d fall further. When markets rose, he was afraid they were too expensive.

He was always waiting for the perfect moment—which never arrived.

Eventually we reframed the conversation using the shot clock. “You don’t need to make the perfect shot,” I told him. “You just need to run the possession.”

Instead of trying to predict the market, we built a plan of staged investments—small allocations over time. Each one was a small bet, not a grand prediction.

Ben’s shift was not just financial. It was psychological. Once he understood that the goal wasn’t perfection, but simply taking the shot before the buzzer, his anxiety dropped. Within a year, his capital was finally working instead of sitting idle.

The difference wasn’t information. It was the clock.

You can’t stop the shot clock, but you can play the possession

In the NCAA tournament, uncertainty is the game. Good teams know this. They don’t wait for the perfect shot. They run the play, move the ball, and take the shot. They miss some, sure, but they keep shooting because they know they’ll get another chance on the next possession.

Investing is also a long game of short possessions. Decisions, allocations, rebalances. Missed opportunities. Capital deployed.

You can’t control the market, but you do control whether you’re in the game and what you do when you have the ball.

Because the real discipline with investing isn’t more research or forecasting. It’s knowing that a possession is ending and you have to act on the cash you’ve been holding, the allocation you’ve been avoiding, and the plan you’ve been delaying until you “feel comfortable.”

The truth is, the shot clock is always running. You can pretend it isn’t and keep turning over your opportunities. Or you can play the possession.

Photo Credit: Meleck Eldahshoury/Michigan DAILY