Open Enrollment Isn't Just HR Paperwork — It's a Tax Planning Opportunity
It's that time of year again. Somewhere between the kids going back to school and the leaves starting to turn, an email lands in your inbox: “Open Enrollment Begins October 1.” For a lot of successful people, that email gets a quick skim, maybe a forwarded note to a spouse, and then... nothing. The deadline creeps up, and the path of least resistance wins: you just re-elect whatever you had last year.
We get it. You're busy. Open enrollment feels like a chore, not a strategy session. But here's the thing — some of the most underused, tax-efficient tools available to you aren't buried in your brokerage account or your estate plan. They're sitting right there in your benefits portal, and most people click past them every October.
If your income has changed, your family situation has changed, or your employer has changed what's offered (all of which happen more often than people think), last year's elections may not be this year's best move. Let's walk through four benefits worth actually reading about this year: HSAs, FSAs, dependent care accounts, and prepaid legal plans.
Health Savings Accounts: The Most Underrated Account You Own
If you have access to a Health Savings Account through a high-deductible health plan, this is the one benefit we'd ask you to stop and really think about — because most people treat it like a checking account for copays, when it's actually one of the best long-term wealth-building tools in the tax code.
HSAs are triple tax-advantaged, and there's genuinely nothing else like it:
● Contributions go in pre-tax (or you get a deduction if you contribute outside of payroll)
● The money grows tax-free while it's invested
● Withdrawals for qualified medical expenses come out tax-free
No other account — not your 401(k), not a Roth IRA — gives you a tax break coming in, growing, and going out.
For 2026, the contribution limits are:
● $4,400 for self-only coverage
● $8,750 for family coverage
● An additional $1,000 catch-up contribution if you're 55 or older
Worth noting: the IRS typically releases 2027 limits in the September–October timeframe, so keep an eye out — those numbers will be public right around the time you're making your elections.
“But I don't want a high-deductible plan”
This is the objection we hear most, and it's worth addressing directly, because it usually stops people before they ever look at the HSA itself: to be eligible for an HSA, you have to be enrolled in a qualifying high-deductible health plan (HDHP). The word “deductible” makes people picture skipping care they need because they're worried about the bill. In practice, that's not how these plans work.
Under the Affordable Care Act, most health plans — including HDHPs — are legally required to cover a long list of preventive services at no cost to you, before you've paid a dime toward your deductible. That includes things like annual physicals, standard cancer screenings, immunizations, cholesterol and blood pressure checks, and well-woman and well-child visits. You can see the full list directly from the federal government here: healthcare.gov/coverage/preventive-care-benefits.
So, the deductible on an HDHP generally applies to non-preventive care — treating an illness or injury — not to the routine checkups and screenings that keep you healthy in the first place.
Once that objection is out of the way, the actual trade-off is pretty straightforward: HDHPs typically come with a noticeably lower monthly premium than a traditional PPO, and that premium savings — combined with the ability to fund an HSA — is the whole rationale for choosing one. You're paying less every month, your preventive care is still covered, and you get access to the triple-tax-advantaged account described above. For a lot of higher-income households who don't have significant ongoing medical needs, that combination often works out favorably compared to a richer, more expensive plan.
The strategy most people miss: don't spend it, invest it
Here's where it gets interesting for someone in your situation. If you have the cash flow to cover your current medical expenses out of pocket, consider leaving your HSA balance alone and investing it instead. Most HSA providers let you invest the balance above a small cash cushion, similar to a 401(k) — index funds, target date funds, and the like. Left invested over 10 or 20 years, that account can grow into a meaningful tax-free pool of money.
And here's the part that surprises even sophisticated clients: you don't have to reimburse yourself for a medical expense in the year it happened. As long as the expense was incurred after your HSA was established, you can pay for it out of pocket today, save the receipt, and reimburse yourself from the HSA years — even decades — later, completely tax-free. There's no expiration on that reimbursement right.
That means an HSA can quietly double as a retirement account with a longer runway than you might expect. Practically speaking, that requires one habit: keep your receipts. A simple, organized folder in a cloud storage account (Google Drive, Dropbox, iCloud — whatever you already use) labeled by year is enough. Snap a photo of the receipt when you pay, drop it in the folder, and you've created a paper trail that lets you pull tax-free money out of your HSA whenever you actually want or need it — even if that's 20 years from now.
Flexible Spending Accounts: Use It for What You Already Know You'll Spend
An FSA works differently than an HSA — it's a “use it or lose it” account (with a small carryover or grace period allowed by some plans), and you can't invest the balance. But for predictable, known expenses, it's a straightforward way to pay with pre-tax dollars instead of after-tax dollars.
The math is simple, but it adds up. Say you're in a combined federal and state marginal tax bracket of 35%, and you know you'll spend $3,000 next year on out-of-pocket dental work, contacts, or prescriptions. If you pay that $3,000 with after-tax income, you actually had to earn roughly $4,600 to have that much left after taxes. Run that same $3,000 through an FSA, and you pay for it with pre-tax dollars — putting about $1,050 back in your pocket that would have otherwise gone to taxes.
The key is being realistic about what you'll actually spend, since unused funds are generally forfeited. If you know braces are coming, a procedure is scheduled, or you reliably spend a certain amount on contacts and prescriptions every year, an FSA is close to free money.
Dependent Care Reimbursement Accounts: Don't Forget This One
If you have children in daycare, after-school care, or a summer camp that qualifies, or you're covering care for an aging parent who's your tax dependent, a Dependent Care Reimbursement Account (DCRA) lets you set aside up to $5,000 per household pre-tax for those costs.
This is one we see high earners skip, either because they forgot to re-elect it or because they assume it's not worth the paperwork. But the savings are real: at that same 35% combined bracket, running the full $5,000 through a DCRA instead of paying out of pocket saves roughly $1,750 in taxes. That's real money, for an expense you were going to pay regardless.
One planning note: if your household income is high enough to phase out of certain child tax benefits, the DCRA is one of the few remaining levers you have to get pre-tax treatment for care costs. It's worth a second look even if you skipped it in years past.
Prepaid Legal Services: The Benefit That Quietly Handles Your Estate Plan
This one isn't about tax savings — it's about closing a gap we see constantly. A lot of successful families have investment accounts, retirement accounts, and real estate that's all meticulously managed, but no updated will, no current power of attorney, and no healthcare directive. Or they had documents drafted 15 years ago, before a divorce, a move to a new state, a new grandchild, or a business sale.
Many employers now offer prepaid legal services as a voluntary benefit during open enrollment — often for a modest monthly payroll deduction. These plans typically include access to an attorney network for drafting or updating wills, trusts, powers of attorney, and healthcare directives, often at no additional cost beyond the plan premium, or at a meaningfully discounted rate.
If you've been meaning to “get around to” updating your estate documents, this is about as low-friction a way to do it as exists. You're not choosing between paying an attorney's full hourly rate or doing nothing — the plan gives you a built-in, affordable path to actually finish it. If your plan offers this benefit, it's worth electing this year and putting a reminder on your calendar to actually use it.
The Real Takeaway: This Is a Ten-Minute Decision With a Multi-Year Payoff
None of this requires a financial degree or hours of research. It requires ten focused minutes during open enrollment, ideally before you're staring down the deadline on the last day. A few questions worth asking yourself before you hit “submit” on your elections:
● Has my income, family situation, or health coverage changed since I last looked at these elections?
● Am I treating my HSA like a spending account when it could be a long-term, tax-free investment account?
● Do I have a system — even a simple one — for saving medical receipts so I can reimburse myself later?
● Are there known, predictable expenses next year I could be paying with pre-tax FSA or DCRA dollars instead of after-tax income?
● Do I actually have current, accurate estate planning documents — and if not, is there a benefit sitting in my enrollment portal that could help me fix that?
Open enrollment isn't just an HR formality. For a few minutes of attention each October, it's one of the more reliable ways to reduce your tax bill and shore up your financial plan — and unlike a lot of tax strategies, this one doesn't require you to do anything complicated. It just requires you to actually look.
All investments contain risk and may lose value. Past performance is not an indication of future performance. Information contained herein has been obtained from sources believed to be reliable but not guaranteed. This material has been distributed for informational purposes only and should not be considered as investment advice or a recommendation of any particular security, strategy or investment product.
Statements concerning financial market trends or portfolio strategies are based on current market conditions, which will fluctuate. There is no guarantee that these investment strategies will work under all market conditions or are appropriate for all clients and each client should evaluate their ability to invest for the long term, especially during periods of downturn in the market. Outlook and strategies are subject to change without notice.