You Didn’t Overpay Taxes in April. You Under-Planned in October

By: Jack Strulowitz

A client sat down with me last week, frustrated. He’d just filed his taxes and owed way more than he expected. “What went wrong?” he asked. The honest answer? Nothing went wrong. His CPA did the return perfectly. But nobody looked at his situation back in October when we could have actually done something about it.

That’s the thing about taxes most people don’t realize. By the time you’re sitting in your accountant’s office in March, it’s already too late. You’re not planning; you’re just reading the score. And if you don’t like the number, tough. The clock ran out months ago.

Here’s how it usually goes. You meet with your CPA sometime around Purim. He tells you what you owe. You either kvetch about it or breathe a sigh of relief. Then you put your tax return in a drawer (or more realistically, somewhere in your email you’ll never find again) and you don’t think about taxes until the following March.

That’s not tax planning. That’s tax reacting. And the difference between the two can be tens of thousands of dollars.

Real tax planning happens in September, October, and November, when there’s still time on the clock. Can you accelerate a deduction? Harvest a loss in your portfolio? Make a charitable contribution through a donor-advised fund instead of writing a check in December? Convert part of a traditional IRA to a Roth while your income is temporarily lower? None of these are exotic strategies. They’re basic, well-known plays. But they all require you to pay attention before the ball drops on December 31st.

My client from last week? If we’d had a conversation about it in the Fall, we could have likely reduced his tax bill significantly. Not through anything aggressive or complicated. Just by being proactive instead of reactive. That’s what frustrated him the most. It wasn’t that the system failed him. It’s that nobody was quarterbacking it.

Your tax return is one of the most useful financial documents you’ll ever receive, and almost nobody treats it that way. It’s not just a bill. It’s a scorecard. It tells you exactly where your money came from, where it went, and what you paid for the privilege.

Think of it like the box score after a basketball game. If your team lost by 20, you don’t just say “tough game” and move on. You look at the stats. Where did we turn it over? Who wasn’t shooting well? What do we adjust for next time? Your tax return answers the same kinds of questions, just with dollar signs instead of field goal percentages.

But most people never look at it that way. They check the bottom line, what they owe or what they’re getting back, and close the file. That’s like reading the final score and skipping the whole game.

The good news? This year’s planning season starts today. Not in September. Right now. You just filed, which means your 2025 numbers are fresh. That makes this the single best time to sit down and ask a few honest questions:

Was my tax bill what I expected? If it was way higher, what drove it? A big capital gain? A distribution I forgot about? Side income that wasn’t being withheld?

Am I maximizing retirement contributions? A lot of people leave money on the table here, especially business owners who could be using SEP IRAs, solo 401(k)s, or cash balance plans.

Is my portfolio actually tax-efficient? Where your assets set (either taxable or tax-deferred vs. tax-free) matters just as much as what you owe. It’s like real estate: same house, different neighborhood, completely different value.

Do I have a strategy for charitable giving? If you’re already giving generously, and in this community most people are, you might as well do it in the most tax-smart way possible. A donor-advised fund, for example, lets you front-load a deduction now and distribute the gifts over time.

Nobody’s going to knock on your door in July to remind you to think about taxes. That’s what makes this so easy to ignore and so expensive when you do. The families I work with who pay the least in taxes aren’t doing anything wildly complicated. They’re just planning in October instead of panicking in March.

So, before you put 2025 in the drawer for good, take one more look. This time, use it as a playbook, not a receipt. 

Jack Strulowitz is a Financial Advisor at Bernath & Rosenberg in Cedarhurst, NY, where he helps high–net worth individuals and families manage their investments and build comprehensive strategies for retirement, tax, and estate planning. For questions or to schedule a consultation, please contact [email protected] or 847-962-3352.

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

Securities and advisory services offered through LPL Financial, a registered investment advisor, member FINRA/SIPC.