By Ari Baum, CFP®
EVERY SPRING, I WATCH SMART, SUCCESSFUL PEOPLE WRITE LARGE CHECKS TO THE IRS. THEN COMES THE QUIET QUESTION I’VE HEARD MORE TIMES THAN I CAN COUNT: “COULD I HAVE DONE MORE?” SOMETIMES THE HONEST ANSWER IS NO. BUT OFTEN, THE ANSWER WAS SITTING IN PLAIN SIGHT MONTHS EARLIER, BACK WHEN THE YEAR WAS STILL OPEN.
That’s why some of the most useful money conversations I have with clients don’t happen in April at all. They happen in November, when there’s still time to make a difference.
LOOKING BACK VERSUS LOOKING AHEAD
Most people think of taxes as something that happens to them once a year. The forms arrive in the mail, the CPA puts everything together, the return gets filed, and you find out what you owe. That process is called tax preparation, and it matters. But it only tells you what already happened.
Tax planning works differently. It takes place while the year is still in motion, and it asks a simple question, based on what we know right now, is there anything worth doing before December 31? Preparation is the report card. Planning is the studying you do before the test. Only one of them can still change the grade.
THE QUIET DEADLINE THAT PASSES EVERY YEAR
Many of the decisions that shape your April tax bill have a December 31 deadline. Nobody sends a reminder, so the date often slips by without a second thought.
Take Roth conversions. Moving part of a traditional IRA into a Roth IRA means paying tax now in exchange for taxfree growth and withdrawals later. It tends to make the most sense in a year when your income is lower than you expect it to be down the road. To count for this year, the conversion has to be finished by year-end.
Investment losses can also help. If some holdings are worth less than you paid, selling them can offset gains elsewhere in your portfolio. This is often called tax-loss harvesting. The trades must happen before the year closes, and the wash-sale rule means you can’t buy back the same or a nearly identical investment within 30 days.
Charitable giving is another area where timing and method matter. Giving appreciated stock instead of cash can avoid capital gains tax on the growth. A donor-advised fund lets you take a deduction this year and recommend grants over time. If you’re 70½ or older, a qualified charitable distribution from your IRA can support the causes you care about while keeping that money out of your taxable income. And since 2026 is the first year new charitable deduction rules apply, even long-standing giving habits deserve a fresh look.
For business owners and executives, the timing of income can be just as important as the amount. A bonus, a stock option exercise, or a large sale might be shifted from one year to the next. That choice can make a real difference, especially for someone close to the edge of a higher tax bracket. And if you’re required to take minimum distributions from retirement accounts, those generally need to be completed by December 31 to avoid a penalty.
None of these ideas fits every household. Some years, the smartest move is to do nothing at all. The point isn’t to chase every strategy. It’s to make sure the decision is made on purpose rather than by default.
TWO EXPERTS, ONE CONVERSATION
The best results I’ve seen come from teamwork. Your CPA knows the tax code and your filing history. We know your portfolio, your cash flow, and the goals you’re working toward. When those two views come together before the year ends, the picture gets much clearer.
In one recent case, we sat down side by side with a client’s CPA, walked through several options together, and meaningfully reduced what that client owed. Every situation is different, so results will vary. Still, the lesson stays the same, the conversation has to happen while there’s time to act on it.
NOBODY GETS FASTER ON RACE DAY
I’ve spent a lot of time around endurance sports, and one truth holds up every time. Race day doesn’t make you faster. It simply shows the training you already put in.
Money works the same way. One of my mentors taught me that the best decisions are made in an unhurried manner. A rushed choice during the last week of December rarely meets that standard. A calm, thoughtful one in November usually does.
So before the holidays fill your calendar, set aside an hour to look at the year ahead of its finish line. Bring your questions, and if you’d like, bring your CPA too. April is when you find out how the year went. November is when you can still shape the outcome.
This article is for informational purposes only and should not be considered legal, tax, or investment advice. Investing involves risk including the potential loss of principal. No investment strategy can guarantee a profit or protect against loss in periods of declining values. Past performance does not guarantee future results. Consult with a financial professional regarding your specific situation.
Ari Baum, CFP® is the Founder and CEO of Endurance Wealth Partners. For nearly three decades, he has helped individuals, families, and business owners turn complex financial decisions into plans they can execute with confidence. Securities and Advisory services offered through Prospera Financial Services Inc. Member FINRA/ SIPC. Brokerage and Advisory accounts carried by Wells Fargo Clearing Services LLC.
