Your Fall Financial Check-In: 5 Things to Tackle Before Year-End
There’s a particular feeling that shows up in October — the air gets crisper, the pumpkin spice everything reappears, and somewhere in the back of your mind a little voice starts whispering, “the year is almost over.” That voice is worth listening to, at least when it comes to your finances.
The fourth quarter is quietly one of the most important stretches of the financial year. A handful of deadlines are real and firm (not “get to it eventually” firm — actually firm), and a little planning now can save you some scrambling later. So grab a warm drink and let’s walk through five things worth putting on your radar before ringing in 2027.
If you’re on Medicare, mark your calendar for October 15
Medicare’s Annual Open Enrollment Period runs from October 15 through December 7, and it’s the one window each year where you can freely switch Medicare Advantage plans, move between Advantage and Original Medicare, or change your Part D prescription drug plan for the coming year.
Here’s the thing most people don’t realize: your plan can change even if you don’t. Drug formularies shift, premiums adjust, and provider networks get updated every year. A plan that was perfect for you in 2026 might quietly become a worse fit for 2027 without you ever getting a dramatic notice about it. It’s worth a 20-minute review — check your plan’s “Annual Notice of Change” letter, compare your prescriptions against next year’s formulary, and make sure your doctors are still in-network. If this doesn’t apply to you yet, feel free to skip ahead — but if you have a parent or family member on Medicare, this is a kind thing to help them check.
Check your HSA and FSA balances
Health Savings Accounts roll over year to year, so there’s no rush there — but Flexible Spending Accounts are a different story. Most FSAs operate on a strict “use it or lose it” basis, sometimes with a short grace period or a small carryover allowance depending on your employer’s plan. If you’ve got a balance sitting there, now’s the time to check the rules and use it on eligible
expenses — glasses, dental work, that physical therapy co-pay you’ve been putting off — before it disappears.
Know this year’s retirement account numbers
Every year, the IRS updates how much people are allowed to put into retirement accounts like a 401(k), 403(b), or IRA. The 2026 numbers brought some meaningful increases, and it’s worth knowing them even if investment decisions aren’t something we work on together.
For 2026, the IRS set the employee 401(k) deferral limit at $24,500, with an additional $8,000 catch-up contribution allowed if you’re 50 or older, and a special $11,250 catch-up if you’re between 60 and 63. The IRA contribution limit is $7,500, plus a $1,100 catch-up for those 50 and older.
One additional wrinkle: starting this year, IRS rules require that if you earned more than $150,000 in the prior year, any catch-up contributions to a workplace plan must go into a Roth account rather than pre-tax. If that applies to you, it’s worth a conversation with your tax preparer or whoever manages your investment accounts, since it can affect your year-end tax picture.
These are just the numbers to be aware of — decisions about how much to contribute and where those dollars are invested are best made with your investment professional or plan administrator. I’m always happy to be part of the conversation about how retirement savings fits into your broader financial and insurance picture.
Give yourself time to think about charitable giving
If giving to charity is part of your year-end plans, October is a good time to start thinking it through rather than scrambling during the last week of December. There’s more than one way to approach charitable giving — direct gifts, giving through a donor-advised fund, or strategies involving investment accounts — and the right approach depends on your full tax and financial picture. If you work with a tax preparer or investment professional, it’s worth starting that conversation now so you have time to be thoughtful rather than rushed.
Put a year-end review on the calendar
Last but not least — if we haven’t already found time to talk before the end of the year, let’s get something on the calendar. A year-end review is a great chance to check in on your insurance coverage, your goals, and how everything is fitting together — especially if anything changed for you this year, like a new job, a move, a growing family, or a milestone birthday. If your plan includes investment accounts, this is also a natural moment to loop in whoever manages those so everyone’s working from the same picture.
As always, I’m here if you want to talk through any of this in more detail. Wishing you a cozy, low-stress start to the fourth quarter.
Warmly,
Jason
This newsletter is for general informational and educational purposes only and does not constitute individualized investment, tax, or legal advice. Jason Arseneault is licensed to offer insurance products and does not provide investment advisory or securities-related services; nothing in this newsletter should be construed as a recommendation regarding the purchase, sale, or management of any investment or security. Contribution limits, tax rules, and Medicare guidelines are current as of the publication date and are subject to change. Please consult a licensed investment professional, tax professional, or attorney regarding decisions specific to your situation.
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