Every fall, I have the same conversation with clients. They think tax planning ends in April, but the real deadline is December 31st. Once the year wraps up, many of the best tax-saving opportunities disappear. The good news is that a few thoughtful steps now can make a real difference. Here's the checklist I walk through with families each year.
1. Make sure you're not underpaying.
One of the most common surprises I see when clients file their taxes is an unexpected IRS bill, sometimes with underpayment penalties. I encourage clients to review their income, deductions, charitable giving, and tax payments now. If they're behind, there's still time to make up the difference through paycheck withholding, an estimated payment, or withholding from a retirement account withdrawal.
2. Know the new rules for charitable giving.
This is one of the changes I'm most excited about because it will help more taxpayers. If you take the standard deduction, as most people do, you can now deduct up to $1,000 in donations, or $2,000 if you're married. If you itemize, there's a small catch: only the portion of your giving above 0.5% of your income counts.
3. Turn losing investments into a win.
Even in a strong year for the markets, most portfolios have a few disappointments. When I review client accounts, I look for investments sitting at a loss, because selling them can offset the taxes owed on the winners. We call it "tax-loss harvesting," but I like to think of it as finding a silver lining.
4. Watch the fine print on Medicare and health insurance.
For clients on or nearing Medicare, I watch how year-end moves might affect income, since higher income can increase IRMAA premiums. If you buy coverage through the ACA marketplace, pay close attention this year. The extra subsidies have expired, so earning even a little over 400% of the federal poverty line could mean losing that help altogether.
5. Build a Roth IRA conversion plan.
The years immediately following retirement are often some of the lowest-income years you'll have. That can make a Roth IRA conversion especially attractive, allowing you to move money from a traditional IRA to a Roth IRA and potentially pay taxes at a lower rate before future income sources kick in.
6. Don't let your cash sit on the sidelines.
I understand the comfort of holding extra cash when the world feels uncertain. But over time, inflation quietly erodes your buying power and can slow down your retirement progress. Year-end is a great moment to make sure your investments still match your goals, rebalance anything that has drifted too far, and confirm your money is working as efficiently as it can.
The most meaningful conversation I have with clients each year has nothing to do with numbers. I simply ask: is your money supporting the things you care about most? For some it's family, for others it's travel, giving back, or the freedom to live life on their own terms. After all these years, I still believe wealth isn't the goal. It's the tool that helps you get there.
As for me, I'll be following my own advice, tidying up my numbers and coordinating with my own advisors this fall. That way, when the holidays roll around, I can set the spreadsheets aside and focus on what matters most: time with family and friends.