What We Actually Check With Clients in September, Before the Year-End Rush

Every December, the phone at the Sandusky office starts ringing a little harder. Someone forgot their required distribution. Someone’s Medicare plan dropped their doctor. Someone wants to make a gift to the grandkids and the check has to clear by the 31st. All of it is fixable. Most of it is fixable more cheaply in September.

September is the quiet month. The boats are still in the water, Cedar Point is running weekends only, and the kids are back in school. Nobody is thinking about taxes. That’s exactly why it’s the best time to look.

Below is what we actually go through with retirees and pre-retirees at this time of year. It’s not a generic checklist. It’s the list we’d work through at your kitchen table if you asked us to.

1. We Read the Medicare Mail Before October 15

If you’re on a Medicare Advantage or Part D plan, your plan’s Annual Notice of Change arrives by the end of September. Most people toss it in the pile with the seed catalogs. Don’t.

That notice tells you what’s changing next year: premiums, copays, which pharmacies are preferred, and whether your prescriptions are still covered at the same tier. Open Enrollment runs October 15 through December 7. If you wait until you’re at the pharmacy counter in January to find out, you’re stuck for the year.

Two local resources worth knowing. Ohio residents can get free, unbiased plan counseling through OSHIIP, the Ohio Senior Health Insurance Information Program. Florida residents have the same through SHINE. We’re happy to sit in on that conversation, too, because your Medicare choice and your income plan are connected. More on that in section 4.

2. We Look at the Drift, Then Decide Where to Fix It

A good year in the market quietly changes your risk. Here’s the math on a hypothetical couple with $800,000 and a 60/40 target between stocks and bonds.

• Target stock allocation: 60% of $800,000 = $480,000
• After a strong run, stocks now make up 67%: $536,000
• That’s $56,000 more in stocks than the plan calls for

If stocks then fell 20%, which has happened more than a few times over the past 50 years, that extra $56,000 alone would give back $11,200 your plan never signed up to risk. (Hypothetical illustration only. Not a projection.)

The fix is rebalancing. The question we care about is where you do it. Selling winners in a taxable brokerage account can create a capital gains bill. Making the same trades inside an IRA doesn’t. And if you’re taking a required distribution this year anyway, we can take it from the side that’s overweight. You were going to withdraw the money regardless. Might as well let it do some housekeeping on the way out.

While we’re in there, we look at your cash. Most of our clients have a Happy Number, the balance that has to be sitting in the bank for them to sleep at night. We respect that number. We also show you what it costs. Every dollar above what you actually need in cash is a dollar earning bank rates instead of working inside your plan, and on six-figure balances that gap adds up to real money every year.

3. We Schedule the RMD and the QCD Now, Not December 28

If you’re 73 or older, your required minimum distribution has to be out of your traditional IRA by December 31. Miss it and the IRS penalty is 25% of what you should have taken, reduced to 10% if you correct it quickly. That’s a steep price for forgetting.

If this is your first RMD year, you technically have until April 1 of next year. Be careful. Waiting means taking two distributions in one tax year, which can push you into a higher bracket and a higher Medicare premium at the same time.

If you give to your church, the Lake Erie Nature & Science Center, or anywhere else, and you’re 70½ or older, look hard at a Qualified Charitable Distribution. The money goes straight from your IRA to the charity. It counts toward your RMD, and it never shows up in your taxable income. That last part matters more than most people realize, because lower income can also mean a lower Medicare premium two years from now.

QCD checks are made out to the charity and often mailed. If the charity doesn’t cash it until January, you may have a problem. Set it up in the fall.

4. We Check What the Rest of the Year Does to Your Tax Bill

For working people, “check your withholding” means updating a W-4 after a wedding or a new job. For retirees, it’s a different animal. Your income is coming from a pension, Social Security, IRA withdrawals, and maybe a part-time job at the golf course. Each one withholds on its own, and none of them talk to each other.

Three things we look at in September:

The new senior deduction. For tax years 2025 through 2028, taxpayers 65 and older can take an additional deduction of up to $6,000 each, or up to $12,000 for a married couple where both qualify. It phases out once modified adjusted gross income passes $75,000 for single filers or $150,000 for joint filers. If you qualify and your withholding hasn’t been adjusted, you may be sending the IRS more than you need to all year.

The Roth conversion window. If you’re in a lower bracket this year than you expect to be once RMDs start, a partial Roth conversion can make sense. But every dollar you convert counts as income, and Medicare looks back two years to set your premiums. Income you report in 2026 sets your 2028 Part B and Part D costs. For 2026 premiums, the first surcharge (called IRMAA) kicked in at $218,000 of income for married couples filing jointly. Go $1 over a threshold and you pay the higher premium for the full year. So we run the conversion number and the Medicare number together, and we’d rather do it in September than guess in late December.

Ohio’s side of the return. Ohio doesn’t tax Social Security benefits, but it does tax pension and IRA income. If you split time between Sandusky and Madeira Beach, where you’re legally domiciled matters a great deal here. That’s a conversation to have with your tax advisor before you change anything.

5. If You’re Still Working, We Look at the Last Four Paychecks

For pre-retirees, September leaves roughly four months of payroll to hit this year’s limits. The 2026 numbers:

• 401(k), 403(b), or 457 contributions: up to $24,500
• Catch-up at age 50 and over: an additional $8,000
• Ages 60 through 63: a larger catch-up of $11,250 in place of the standard one
• IRA: up to $7,500, plus $1,100 at age 50 and over

One new wrinkle for 2026: if you earned more than $150,000 in FICA wages from that employer last year, your catch-up contributions now have to go in as Roth, not pre-tax. Some payroll systems handle this smoothly. Some don’t. Check your pay stub.

If you have a Health Savings Account and you’re planning to start Medicare soon, stop contributing six months before you enroll. Medicare Part A coverage can be backdated up to six months when you sign up after 65, and HSA contributions made during that window can create a tax problem.

If your employer offers a Flexible Spending Account, most of those balances are use-it-or-lose-it. Schedule the eye exam and the dental work now.

6. We Pull the Beneficiary Forms Out of the Drawer

This is the one that causes the most heartache, and it takes about ten minutes to check.

The beneficiary named on your IRA, your 401(k), and your life insurance policy overrides whatever your will says. We have seen ex-spouses still listed. We have seen a spouse who passed years ago still listed as primary with no contingent behind them. We have seen minor grandchildren named directly, which in Ohio usually means a court has to get involved before a dime moves.

A few Ohio-specific tools worth knowing about:

• Transfer on Death Designation Affidavit. Ohio lets you name a beneficiary on your house through a recorded affidavit, so it can pass outside probate.
• Transfer on Death for vehicles. Ohio also allows a TOD beneficiary on a vehicle title through the BMV. Yes, that includes the boat trailer and the collector car in the garage.

Also keep in mind that most non-spouse beneficiaries who inherit an IRA now have to empty it within 10 years. If your plan is to leave a large IRA to adult children who are in their peak earning years, the tax hit on them may be bigger than you think. That’s worth a planning conversation.

We review designations and titling with you. We don’t draft legal documents. When something needs to be written or recorded, we work alongside your estate attorney.

7. We Talk About the Grandkids Before the Holiday Spending Starts

The original version of this checklist said to set a holiday budget. Fair enough. For our clients, the bigger question is usually what you want to do for the family this year, and how to do it in a way that makes sense.

The annual gift exclusion. In 2026, you can give up to $19,000 to any one person without filing a gift tax return. A married couple can give $38,000 to each child or grandchild.

Ohio’s 529 deduction. Ohio residents who contribute to Ohio’s CollegeAdvantage 529 plan can deduct up to $4,000 per beneficiary per year on their Ohio return, and any amount over that carries forward to future years. Grandparents qualify. If you’re a Florida resident, there’s no state income tax to deduct against, so the math is different.

The FAFSA change. Under the simplified FAFSA, distributions from a grandparent-owned 529 no longer count against the student’s financial aid the way they used to. That removed one of the old reasons grandparents hesitated.

One honest word on this. We see a lot of generous parents and grandparents. We also see some who help the family so much that their own retirement starts to wobble. Helping is wonderful. Just make sure the gift fits the plan, and not the other way around.

And with the holidays coming, the scam calls pick up. Fake grandchildren in jail, fake IRS agents, fake bank fraud departments. If anyone calls asking you to move money quickly, hang up and call our office first. Every time.

The Preach

You’ve been handling your own money for 40 years. You know what a stock is and you know what a bond is. You don’t need a lecture.

What most people don’t have is the time or the software to see how all of this connects. The RMD affects the tax bracket. The tax bracket affects the Medicare premium. The Medicare premium affects the monthly budget. The budget decides how much you can give the grandkids. Pull one thread and the whole sweater moves.

December is when everybody tries to fix it at once. September is when there’s still room to do it right. Give yourself the gift of time on this one, because in our experience, the people who plan in the fall almost NEVER wish they had waited.

If you’re already a client, call Kristin and get on the calendar before October fills up. If you’re not a client yet, why not? What’s holding you back? A first meeting costs you nothing but an hour, and you’ll leave knowing exactly where your numbers stand.