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Why Financial Planning is Like Pickleball: Lessons for Independent Contractor Physicians

If you know anything about me, pickleball is definitely my favorite sport to play. It’s not just a trend – it’s an outright obsession. And before you say it’s just a game, not a sport…that just means you’re not very competitive at it and play the wrong way! I used to be a high-level tennis player, but since picking up a pickleball paddle (not racket but paddle), it’s taken over my life. I even went to pickleball camp by myself in Florida when my family went to Chicago during the winter. True story!

So why is pickleball so great? Because it’s easy to pick up – you can grab a paddle and start playing immediately – but it’s really, really difficult to master as you understand the advanced strategies. Unlike tennis, where you can’t just pick up a racket and start playing (it’s too hard), pickleball is accessible yet deep.

The Pickleball Approach to Financial Planning

What does this have to do with financial planning for physicians? More than you might think.

Pickleball is all about patience. When you watch a match, you’ll see a lot of what players call “dinking.” Unlike tennis, where you’re often at the baseline just pounding away at the ball as hard as you can, pickleball is largely a finesse sport. You start in the back, but you make your way up to “the kitchen” (also known as the non-volley zone).

When you’re at the kitchen line, you’ll often see players just dinking it – getting that yellow wiffle ball over the net, but just barely onto the other side of the kitchen. This isn’t directly winning points – you’re setting up. You’re never winning a point per se on a dink. Instead, you’re putting the ball in a position where your opponent has a really difficult time retrieving or attacking it. It’s low, it’s at their feet, so they have no choice but to dink it back.

So you’re dinking, dinking, dinking. At a certain point, if you win that dink battle, your opponent is going to scramble and “pop it up.” That’s when you smash the ball, and that’s when you win the point. If you can do this consistently, you’re going to win more points and more matches than not.

Financial Planning Requires the Same Patience

Financial planning isn’t about being aggressive and just “smashing the ball” at every opportunity. It’s about being patient. It’s about working with the market, playing the slow game, playing the soft game, having the patience where you’re dinking it.

For physicians, this might mean making monthly contributions to your Solo 401(k) or brokerage account on a consistent basis. Slow dink. Slow dink. But when there’s a downturn in the market – like a tariff-driven selloff or another “liberation day” volatility event – that’s where you identify those opportunities. The ball has popped up, and then you smash it!

That’s what we try to teach our physician clients: recognize when the opportunity is there. When it appears, that’s when you tag it. That’s when you speed up the ball, and that’s when you win the point, the game, the match, etc.

Sometimes Defense Is the Best Strategy

When it comes to pickleball, sometimes it’s not about attacking. Sometimes it’s about just playing defense and getting the ball back over at all costs. You know what? Sometimes when you get that ball back over, you make your opponent hit one extra shot – and they mess up.

Sometimes, financial planning isn’t about winning the point directly; it’s about making your opponent (in this case, market volatility or unexpected expenses) miss or hit the ball into the net. And that’s just as effective.

For our independent contractor physicians who deal with variable income, self-employment taxes, and the complexities of your own retirement plans, this defensive strategy is crucial. Having adequate emergency funds, the right disability insurance, and a tax strategy that doesn’t leave you exposed – these are all ways of playing good defense.

The Difference Between Average and Advanced Players

What makes the difference between an average pickleball player and an advanced one? It’s the amount of patience you have at the kitchen line, playing what we call the “soft game” – dinking it, dinking it, dinking it, smash!

Similarly, what makes the difference between average and advanced financial planning for physicians? It’s not constantly changing your investment strategy or chasing the latest hot stock. It’s having the patience to consistently contribute to your retirement accounts, maintaining adequate insurance coverage, and then recognizing those moments when you should be more aggressive – like maxing out a defined benefit plan in a particularly high-income year.

Capturing Opportunities Without Beating Yourself

Just like in any sport, you’ve got to capitalize on the opportunities your opponent gives you. You don’t want to beat yourself. You want to limit the unforced errors and then win when the time is right.

As a physician, your financial game plan should follow this same philosophy. Avoid the unforced errors (inadequate coverage, missed tax deadlines, or ignoring retirement planning), maintain consistent contributions to build your wealth (the dinking game), and be ready to capitalize when opportunities arise (market dips, new tax-advantaged strategies, or career advancement).

Remember, it’s not always about being the most aggressive player on the court – sometimes it’s about having the patience to set up the perfect shot. And that’s true whether we’re talking about pickleball or your financial future.

Whether you’re a dinker or a smasher — on the court or in your financial plan — Ben Yin offers a free 30-minute “Zero Call” to help you figure out which physician strategies you should be patient on, and which you should attack. Book your Zero Call here. (And yes, pickleball tangents are welcome.)

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