Chuck Oliver of The Hidden Wealth Solution on Your 2026 Year-End Retirement Checklist

Chuck Oliver of The Hidden Wealth Solution urges retirees to do more than check their account balances before December 31. He suggests they also take time to review bills, deadlines, taxes, and the family decisions that retirement plans need to address.

Gather five key documents: your spending record, investment statement, Medicare notice, retirement account withdrawal record, and beneficiary forms. Lay them out together. Before you buy another product or move money, check if these documents match and tell a consistent story. This is a practical starting point for your year-end retirement and tax review. Your balance sheet should support the life you want, with enough spendable income and explicit instructions for anyone who may need to step in and help manage your affairs.

As the year ends, ask yourself: What needs attention now, and who will handle it? Examples: taxable events that need to be addressed, Roth conversion planning, tax exposure, being able to save, planning required distributions, etc.

Your spending record should explain next year’s income needs  

Chuck Oliver and his team at The Hidden Wealth Solution recommend you begin by listing what you spent this year. Separate regular expenses from one-time costs, then mark which expenses are likely to return in 2027. For example, a roof repair might be in the past, but property taxes, insurance, groceries, and prescriptions still need a spot in your budget.

Fidelity’s retirement budgeting guidance recommends reviewing bank and credit card records and distinguishing necessary expenses from discretionary spending. Use that exercise to identify the gap between dependable income and the bills your portfolio must cover.

“It’s not what you make; it’s what you keep,” says Chuck Oliver. Build the budget around income available after taxes and deductions, rather than the gross figure on a statement.

List irregular expenses separately. Travel, dental work, helping an adult child, or replacing a car should not be hidden in a monthly average. Decide now which of these expenses you could cut back on if costs go up or investments underperform.

Next, figure out how much cash you have for upcoming bills and surprises. Check if you would need to sell investments, pay a fee, or wait for a transfer to access it. Set aside a reserve that fits your household’s needs. There is no one-size-fits-all answer; every pension, mortgage, and health situation is different.

Your investment statement must match the risk you agreed to take  

As Chuck Oliver notes, a good year in the market can change your investment mix from what you started with. Review all your accounts, even those at different firms. You may realize you own the same investments in more than one place.

The SEC’s Investor.gov guidance on allocation and rebalancing explains that the right mix depends on your time horizon and risk preference. Rebalancing brings a portfolio back to its intended allocation, but you still need to consider transaction costs and tax consequences before you trade.

Be sure your portfolio supports your withdrawals if the market drops. Which assets would you use for spending? Which could stay invested? Would you need to sell more than planned for a big purchase?

Check how concentrated your holdings are, any access restrictions, and your returns. Ask for a clear explanation of what each investment does for you. If something no longer fits your plan, talk about alternatives before making a change.

Use the end of the year as a signal to review your risk, not to try to guess next year’s best investment. Make sure you leave your meeting with a written plan and a clear explanation of any changes.

Your Medicare notice has an earlier deadline  

December 31 is too late for the regular fall Medicare enrollment window. Medicare’s annual Open Enrollment runs from October 15 through December 7. Changes made during that period generally take effect on January 1 of the following year.

Your plan’s Annual Notice of Change describes coverage and cost changes that take effect in January. Chuck Oliver recommends reading it with your current medication list and the names of the doctors and pharmacies you use.

Compare the expected annual expense, including premiums, deductibles, and what you would pay when you need care. Check drug coverage and all relevant provider or pharmacy networks. A familiar plan name alone does not tell you whether the coverage still fits.

If you are considering returning from Medicare Advantage to Original Medicare, review your supplemental coverage before making the change. Medicare cautions that there are limits on when you can add Medigap insurance.

Give yourself enough time to get answers and submit your enrollment before December 7. Keep proof of any changes with your retirement paperwork. Ensure your coverage choice fits both your expected care and your budget.

Your withdrawal record should confirm what is still due  

Check your required minimum distributions based on what you have withdrawn, not just what you planned to do. Ask each account provider what is still outstanding and when it will be processed.

The IRS’s RMD guidance states that subsequent annual distributions are due by December 31. For a traditional IRA owner turning 73 in 2026, the first RMD may be delayed until April 1, 2027. That can push both the first distribution and the next annual RMD into 2027, so compare the income consequences before postponing it.

Chuck Oliver stresses that account type matters. The IRS’s RMD FAQs explain that an owner’s traditional IRA RMDs can generally be totaled and withdrawn from one or more of those IRAs, while 401(k) RMDs generally must be taken separately from each plan. Inherited accounts need their own review. “Don’t take my word for it. Run the math on your own situation,” says Oliver.

Treat this as a final check. Confirm the rules, the amount left to withdraw, where the payment is going, and who is responsible for making it happen. Save the acknowledgment once the withdrawal is done.

Your beneficiary forms should reflect your family today  

Ensure you have the right beneficiary forms for your retirement accounts and insurance policies. Check the names, shares, and backup beneficiaries. Do the forms reflect any recent changes in your family, like a marriage, divorce, death, or new grandchild? Make sure they match your wishes.

Fidelity’s estate-planning checklist explains that beneficiary designations can supersede provisions in a will or trust. Signing estate documents does not automatically update the forms held by financial institutions. Review any changes with your attorney, particularly when a trust or retirement account is involved.

Next, check the documents that apply while you are alive. Fidelity’s estate-plan review guidance includes financial and healthcare powers of attorney and stresses communicating with the people expected to carry out your wishes.

Ask the people you have named as beneficiaries if they are willing to serve and if they know where to find the documents. Make a secure list of your accounts, insurance, professional contacts, and where your documents are kept. Your family should have a clear starting point.

“Love is spelled T-I-M-E,” Chuck Oliver says. Schedule the family conversation while you can answer questions. That meeting belongs on the retirement checklist alongside the account reviews.

Chuck Oliver of The Hidden Wealth Solution on bringing the review together  

With Chuck Oliver and The Hidden Wealth Solution, the first step is to reduce your tax burden. Then, the focus shifts to protecting your wealth, building reliable tax-free income, and preserving your legacy. To reach these goals, your budget, investments, insurance, and family instructions all need to work together. The question one needs to answer is whether you have a portfolio or a holistic plan.

For each item still on your list, write down the next step, its deadline, and who is responsible. Keep the December 7 Medicare deadline and the December 31 withdrawal requirements separate from other reviews you want to finish before year-end. Ask your advisor, tax preparer, and attorney to help.

For more retirement planning ideas, visit The Hidden Wealth Solution’s insights library. End the year with fewer questions and a plan that protects you and your family.

About Chuck Oliver  

Chuck Oliver is the founder and CEO of The Hidden Wealth Solution, a nationally recognized wealth strategy firm specializing in tax-efficient retirement and legacy planning. A two-time best-selling author, national radio host, and lifelong entrepreneur, Chuck helps clients across the U.S. reduce taxes, minimize market risk, and create lasting financial confidence. His passion for empowering others to overcome financial uncertainty drives his belief that true wealth is built through clarity, confidence, and capability.

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