Poolside Planning (Yes, Really)

Michelle Kuehner, ChFC® 

There’s something about summer that makes people collectively forget how numbers work.

Temperatures go up, discipline goes down, and suddenly “budget” becomes more of a suggestion than a plan. Pool floats multiply, weekend trips appear out of thin air, and no one seems overly concerned that their credit card is quietly training for a marathon.

But here’s the thing: summer is actually one of the best times to get a little strategic with your tax planning. I know—nothing says “poolside reading” like tax strategy. Stick with me.

First, let’s talk about income. If your year is shaping up differently than expected—maybe business is booming, maybe it’s…not—summer is the perfect checkpoint. Waiting until December to realize you owe more than expected is like realizing you forgot sunscreen after you’re already burnt to a crisp. Painful and entirely avoidable.

This is where proactive moves come in. Adjusting withholdings, making estimated tax payments, or even accelerating or deferring income can make a meaningful difference. It’s not glamorous, but neither is writing a surprise check to the IRS when you’d rather be booking a beach trip.

Then there’s the classic summer wildcard: bonuses, commissions, or side hustle income. Summer tends to bring out the entrepreneurial spirit—think Airbnb rentals, freelance gigs, or turning a hobby into cash flow. That’s great…until tax season reminds you that the IRS also enjoys your hustle.

Setting aside a portion of that extra income now (yes, now, not “later”) can save you from a financial hangover next spring. A good rule of thumb: if it feels like “extra” money, it’s probably partially the government’s money.

Let’s not forget about capital gains. Summer often comes with a little more time to review investment accounts—ideally from a shaded patio with a cold drink. If you’ve got positions with gains (or losses), this could be a smart time to rebalance. Harvesting losses to offset gains isn’t exactly thrilling, but it is effective. Think of it as financial sunscreen—quietly protecting you from future damage.

Charitable giving also deserves a quick cameo. While year-end tends to get all the attention, spreading out donations during the year can help with cash flow and planning. Plus, it feels slightly less like a December panic decision and more like actual generosity.

And then there’s retirement contributions. Summer is a great time to check whether you’re on track. If you’re self-employed or have variable income, you’ve got flexibility—but that also means responsibility. Waiting until the last minute to figure it out is like cramming for a final exam you forgot you had. Technically possible, but not ideal.

Here’s the bottom line: summer doesn’t have to be a financial free-for-all. You can enjoy the trips, the cookouts, and the questionable amount of money spent on things that inflate and deflate…while still making smart tax moves behind the scenes.

A little mid-year planning now can mean fewer surprises later—and fewer regrets when the tan fades but the tax bill doesn’t.

Because nothing ruins a perfectly good summer memory like realizing it came with interest and penalties.