Plan Smarter, Pay Less
Are You Leaving Money on the Table Every Tax Season?
Our Tax Strategy Calendar helps you plan ahead to minimize surprises—and maximize your returns.
The Tax Moves That Matter Most Near Retirement
Every situation is different, and this calendar isn’t tax advice — it’s a framework for staying ahead. Here are the areas our clients in the Hagerstown, Martinsburg, and Winchester area consistently find most valuable.
Roth Conversion Windows (Jan–Mar, Oct–Dec)
If your income dips in a particular year — or if current tax rates are favorable relative to what you expect in retirement — a strategic Roth conversion can reduce your future required minimum distribution burden and create tax-free income later. The calendar identifies the right windows to have that conversation before year-end deadlines arrive.
Qualified Charitable Distributions (Oct–Dec)
If you’re over 70½ and charitably inclined, a QCD from your IRA can satisfy your RMD requirement without that amount counting as taxable income. It’s one of the most tax-efficient giving strategies available — but it must be executed correctly before December 31.
Tax-Loss Harvesting (Oct–Nov)
In years with market volatility, there’s often real opportunity to offset gains by harvesting losses in taxable accounts. This isn’t something most people think about proactively — the calendar puts it in front of you at the right moment.
Open Enrollment and HSA Contributions (Nov)
Maximizing HSA contributions while you’re eligible is one of the most tax-efficient moves available — triple-tax-advantaged. The calendar reminds you to revisit this before the window closes each November.
If you’d like to work through your specific tax situation with a fiduciary advisor, schedule a conversation with Hoxton PM. The goal is always to help you retire with more of what you saved.
Other worksheets you may find useful: Retirement Readiness Checklist · Personal Risk Management Audit · Net Worth & Budget Worksheet