Most people don’t think about taxes until spring, when the filing deadline is around the corner. But by then, it’s too late to make meaningful changes. The best opportunities happen before the year ends.
With Labor Day right around the corner, summer is winding down and the busy season begins. That makes this the perfect time to pause, take stock, and see if adjustments are needed. Think of it as a financial “halftime review.” You’ve played most of the year, you know the score, and you still have time to adjust your strategy before the clock runs out.
The Window for Roth Conversions
One of the most powerful tools for retirees is the Roth conversion. But the timing matters. Late summer and early fall are when you can look at your actual income year-to-date and estimate where you’ll land by December. If you’re sitting in a lower tax bracket than usual, you may still have room to convert part of your IRA to a Roth at favorable rates.
Wait until January, and that opportunity is gone.
Required Minimum Distributions (RMDs)
If you’re subject to RMDs, now is the time to make sure they’re on track. The penalty for missing an RMD is steep, and scrambling in late December is no one’s idea of fun. Reviewing them now gives you time to confirm distributions, explore strategies to reduce the tax bite, or even consider a Qualified Charitable Distribution (QCD) if giving is part of your plan.
Charitable Giving Opportunities
Charitable gifts often feel like a December decision, but spacing them earlier in the year can give you flexibility. Appreciated securities, donor-advised funds, and bunching strategies (grouping multiple years of gifts into one) all work best when they’re planned, not rushed.
Tax Bracket Management
Many retirees don’t realize how small shifts in income can affect their taxes and even their Medicare premiums. Reviewing your numbers now allows you to smooth income between years, avoid surprises, and potentially reduce long-term tax costs.
Investment Opportunities
If you hold investments in taxable accounts, this is also the time to check whether it makes sense to harvest losses (or even gains) to offset income. Markets move throughout the year, and an early fall review gives you time to be intentional before year-end.
Retirement Plan Contributions
For those still working—or earning consulting income in retirement—this is also the time to check in on your retirement plan contributions. Whether it’s a 401(k), 403(b), or SEP IRA, you still have a few months to maximize contributions for the year.
Why now? Because waiting until December often means cash flow feels tighter, or payroll changes can’t be processed in time. By reviewing now, you can:
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Increase contributions for the remainder of the year to get closer to the IRS limit.
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Confirm you’re taking advantage of any employer match.
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For higher earners, evaluate whether after-tax or Roth 401(k) contributions make sense.
Small adjustments now can make a meaningful difference by December 31st—and give you peace of mind that you’ve made the most of your retirement savings opportunities this year.
A tax checkup at this point in the year isn’t about scrambling. It’s about getting ahead while there’s still time to act.
By taking a little time now—before the holidays, before year-end deadlines—you can make sure the year closes on your terms, not the IRS’s. A small amount of planning now means less stress later, and more freedom to enjoy the months ahead.
