Medicare Decisions & Your Money: What to Review Before Open Enrollment
Practical steps to wrap up the year with confidence, whatever stage of life you’re in.
As the holidays approach, it’s easy to get swept up in to-do lists that have nothing to do with money—gift shopping, travel plans, and end-of-year celebrations. But before the year wraps up, it’s worth giving your finances a little attention too.
A few smart moves now can make April’s tax season easier, keep your long-term goals on track, and help you start the new year with clarity instead of chaos. Below is a quick, stage-by-stage guide to help you focus on what matters most for where you are in life.
For Those Early in Their Careers
This is the time to build habits and systems that make your financial life simpler down the road. A few quick checkups now can make a big difference later.
W-4 Tune-Up:
If you had a raise, bonus, or job change this year, make sure your paycheck withholdings are still accurate. Adjusting your W-4 ensures you’re not giving Uncle Sam an interest-free loan or facing an unexpected tax bill come spring.
Roth IRA Eligibility:
Double-check whether you qualify to contribute to a Roth IRA for the year. Roth contributions grow tax-free, and that’s one of the best deals in personal finance. Even small annual contributions can add up to a big advantage over time.
Student Loan Interest Documentation:
If you’ve resumed student loan payments, keep your interest records organized. That interest could provide a deduction on your taxes, and having documentation ready will make filing easier.
For Mid-Career Professionals
This is the stage where you’re juggling growth, family, and planning for the future. Efficiency and strategy can really start paying off.
Tax-Loss Harvesting Basics:
If you have investments in taxable accounts, now’s the time to review unrealized losses. Selling underperforming assets to offset gains can reduce your tax bill. Just be mindful of wash-sale rules.
Charitable “Bunching”:
Instead of giving small amounts every year, consider “bunching” multiple years of charitable gifts into one tax year to maximize your deductions. This works especially well if you use a donor-advised fund.
Review Equity Compensation Tax Lots:
If you receive company stock or options, review what you’ve sold this year and what’s still sitting in your portfolio. Understanding cost basis and holding periods can help you minimize taxes on future gains.
For Those Approaching Retirement
With retirement on the horizon, it’s all about timing, coordination, and smart planning.
Pension Decision Lead-Times:
If you’re entitled to a pension, check the deadlines for choosing your payout option. These decisions often need to be made months in advance, and the choice you make, lump sum or monthly payments, can have long-term implications.
Net Unrealized Appreciation (NUA) Feasibility:
If you hold company stock in your 401(k), ask your advisor whether an NUA strategy might reduce your tax burden. It’s a complex but potentially powerful move if handled correctly.
Maxing Catch-Up Contributions:
Once you turn 50, you can contribute more to retirement accounts. Take advantage of those extra dollars because they can make a meaningful difference in your final accumulation years.
For Retirees
Retirement doesn’t mean your financial planning stops. It just shifts focus.
RMD Planning Window:
If you’re age 73 or older, make sure your Required Minimum Distribution (RMD) is complete before year-end. Missing the deadline can trigger steep penalties.
Qualified Charitable Distributions (QCDs):
If you’re already taking RMDs, consider donating directly to a qualified charity from your IRA. QCDs count toward your RMD but aren’t included in your taxable income, a double win.
Estimated Taxes:
Review your quarterly estimated payments to make sure you’ve covered your tax obligations for the year. This helps you avoid penalties and keeps cash flow steady.
For Multi-Generational Families
Financial health isn’t just about you. It’s about preparing your family for the future too.
Beneficiary Updates:
Review the beneficiaries listed on your insurance policies, retirement accounts, and estate documents. Life changes quickly, and outdated beneficiaries can cause real headaches later.
Account Titling:
Making sure your accounts are titled properly is critical to make sure your money is set up to pass to your heirs as intended. It is important to make sure this is coordinated with your estate plan. We can help review your documents and accounts for potential issues and reach out to your estate attorney if necessary to help you address any needs in this area.
Family Vault of Key Documents:
Make sure trusted family members know where to find essential information, like account logins, estate plans, and insurance policies. Whether it’s a secure digital vault or a folder in your filing cabinet, clear organization saves time and stress when it matters most.
The Bottom Line
Financial checklists don’t have to be intimidating. A few small, thoughtful actions before December 31 can bring clarity, reduce taxes, and make sure your money is working as hard as you are.
If you’re not sure which items apply to your situation or want help creating your own customized checklist, our team at On Purpose Financial Management is here to help. Let’s make sure you close out the year confident and on purpose.
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Material Prepared by Tic Tac Toe Marketing, an independent third party. Any opinions are those of the author, are subject to change without notice and are not necessarily those of Raymond James. This material is being provided for information purposes only and does not purport to be a complete description of the securities, markets, or developments referred to in this material and does not constitute a recommendation. The information has been obtained from sources considered to be reliable, but we do not guarantee that the foregoing material is accurate or complete. Investing involves risk and investors may incur a profit or a loss regardless of strategy selected. Neither Raymond James Financial Services nor any Raymond James Financial Advisor renders advice on tax or legal issues, these matters should be discussed with the appropriate professional.