Two enrollment windows open at the same time every fall. Benefits packets land in inboxes across Metro Detroit, and Medicare’s Annual Enrollment Period runs October 15 through December 7. Both ask people to make decisions that hold for a full year. Both tend to get decided in a hurry.
The mistakes I see are rarely exotic. Most come down to treating a benefits election as a form to clear rather than a financial decision.
Fifteen Minutes for a Decision That Lasts a Year
The packet arrives, you skim it, you keep last year’s elections, you submit. Fifteen minutes, maybe less.
Consider what you just decided: how much of each paycheck goes to premiums, how much income your family would have if you could not work, how much life insurance your spouse would receive, how much you can set aside pre-tax for medical costs, and which network your family sees for the next twelve months.
No engineer re-specs a system by copying last year’s drawing without checking what changed. Plans change every year. Deductibles move, out-of-pocket maximums move, hospitals leave networks, and carriers get swapped.
Give it an evening. Pull last year’s elections, what you actually spent on care over the past twelve months, and this year’s summary of benefits, then compare what changed instead of electing from memory. That hour belongs to the same category as any other financial planning decision you would not make in a hallway.
Where Group Disability and Life Coverage Fall Short
This is where I see the widest gaps, and they are rarely visible from the enrollment screen.
Group long-term disability often replaces a percentage of base salary. Base salary may be a modest share of total compensation if you are paid heavily in bonus, incentive, or production. For a physician, an attorney on a variable structure, or an automotive executive whose pay leans on annual incentives, the covered figure can be far below what the household actually lives on. Definitions matter too. A policy that pays only when you cannot perform any occupation is a different instrument from one written around your own occupation, which is a distinction that matters enormously for medical professionals.
Taxes change the arithmetic again. The IRS treats disability benefits as taxable income when the employer paid the premiums and you were not taxed on them, and generally tax-free when you paid the premiums with after-tax dollars. Sixty percent of salary reads differently once you subtract taxes from it.
Group life has its own edges. The first $50,000 of employer-provided group-term life coverage is excluded from your income under IRC Section 79, and the cost of coverage above that is added to your W-2 as imputed income. Group life also generally ends when the job does, which is worth knowing before you treat it as your family’s whole plan. All of this belongs in a risk management conversation rather than a benefits portal.
HSAs and FSAs Are Not Interchangeable
People use these two acronyms as though they were the same account. They behave very differently over a long horizon.
An HSA requires an HSA-qualified high-deductible plan. For 2027 the IRS set contributions at $4,500 for self-only coverage and $9,000 for family coverage, with an additional $1,000 for those 55 and older. The balance rolls over, follows you between employers, and can be invested. Some households pay current medical costs out of pocket and let the account compound for later, which makes it part of your investment management and retirement planning strategy rather than a spending account.
An FSA is tied to your employer and largely use-it-or-lose-it. Your plan may offer a carryover or a grace period, but not both, and some offer neither. The IRS sets these amounts in a revenue procedure each fall. At the time of writing, the 2027 health FSA limit had not yet been published; the 2026 limit was $3,400 with a carryover of up to $680. Use the figure in your own plan materials.
One interaction catches people every year: enrolling in a general-purpose health FSA generally disqualifies you from contributing to an HSA. So can your spouse’s FSA, which brings us to the last mistake.
Medicare: October 15 Through December 7
Medicare’s Annual Enrollment Period runs October 15 through December 7, with changes effective January 1. Each fall your plan mails an Annual Notice of Change. It is dull reading, and it is the most useful document you will get all year.
Worth checking before December 7:
- Whether your prescriptions are still on the formulary, and at what tier
- Whether your physicians and preferred hospitals are still in network
- Total expected cost for the year, not the premium alone
- Whether a plan you chose at 65 still fits the care you use now
If you are in a Medicare Advantage plan, a second window runs January 1 through March 31 to switch plans or return to Original Medicare. Doing nothing is itself a decision: without a change by December 7, your current coverage generally continues into the new year. For retirees weighing this alongside housing, taxes, and time on the water, our article on planning your Great Lakes retirement covers the broader picture.
Elect With Your Spouse, Not Beside Them
Most households complete their elections separately and discover the overlap in February. An hour at the kitchen table in October is cheaper.
- Whether two plans are genuinely needed, or whether one family plan costs less
- Which plan covers your dependents and your usual providers better
- Whether one spouse’s FSA election affects the other’s HSA eligibility
- Beneficiary designations on life insurance and retirement accounts, which control who receives those assets regardless of what a will says
- Total disability coverage across both incomes, measured against what the household actually spends
Build the Year Before It Starts
Open enrollment is one of the few financial decisions that comes with a deadline attached, which is exactly why it gets rushed. The elections you make this month set your household’s coverage, cash flow, and tax treatment for the next twelve, and they land in the same season as year-end tax planning decisions worth coordinating with them.
At The Valletta Group, we review benefits elections alongside the rest of the plan for executives, business owners, and professionals across Northville and Metro Detroit, and coordinate with your CPA where the tax treatment matters.
To schedule a meeting, call (248) 720-1780, email mswiecki@vallettagroup.com, or book a time directly.
Disclosure: This material is for informational purposes only and should not be considered individualized investment, tax, or legal advice. Benefit plan provisions vary by employer and plan year, and tax rules may change. Review your own plan documents and coordinate with a qualified tax professional. The Valletta Group does not provide legal or tax services. Investing involves risk, including possible loss of principal.
Frequently Asked Questions
When is Medicare open enrollment in 2026?
Medicare’s Annual Enrollment Period runs October 15 through December 7, 2026, and any changes you make take effect January 1, 2027. Your plan must receive the request by December 7. This window is open to everyone with Medicare, whether you have Original Medicare, a Medicare Advantage plan, or a Part D drug plan. A separate Medicare Advantage Open Enrollment Period runs January 1 through March 31 for those already enrolled in an Advantage plan. If you make no change, your current coverage generally continues into the next year.
Should I choose an HSA or an FSA?
They are not directly comparable, because eligibility depends on your health plan. An HSA requires an HSA-qualified high-deductible plan, and the balance rolls over year to year, follows you between employers, and can be invested for the long term. An FSA is tied to your employer and is largely use-it-or-lose-it, though some plans allow a limited carryover or a grace period. Enrolling in a general-purpose health FSA generally makes you ineligible to contribute to an HSA, and a spouse’s FSA can have the same effect. The right choice depends on your plan options, expected medical costs, and whether you want the account to function as savings or as a spending tool.
Is my employer’s disability insurance enough?
It depends on how you are paid and how the policy is written. Group long-term disability commonly replaces a percentage of base salary, which can leave a meaningful gap for professionals paid substantially in bonus, incentive, or production. The policy’s definition of disability matters as well, since coverage tied to your own occupation differs from coverage that pays only if you cannot perform any occupation. Taxes matter too: benefits are generally taxable when the employer paid the premiums, and generally tax-free when you paid them with after-tax dollars. Reviewing the actual policy language against your household spending is the only way to answer the question for your situation.
Sources
1. Internal Revenue Service, Revenue Procedure 2026-24 (released May 29, 2026): 2027 HSA contribution limits of $4,500 self-only and $9,000 family, $1,000 catch-up at age 55, HDHP minimum deductibles of $1,750 and $3,500, and out-of-pocket maximums of $8,700 and $17,400. (irs.gov)
2. Internal Revenue Service, Revenue Procedure 2025-32: 2026 health FSA salary reduction limit of $3,400 and carryover maximum of $680. The 2027 figures had not been published as of October 8, 2026. (irs.gov)
3. Internal Revenue Service, Publication 15-B, Employer’s Tax Guide to Fringe Benefits, and IRC Section 79: exclusion for the first $50,000 of group-term life coverage; cost of coverage above that is included in wages. (irs.gov)
4. Internal Revenue Service FAQ, Life insurance and disability insurance proceeds: disability amounts received under an employer-paid plan are reportable as income; amounts under a plan paid for entirely with after-tax dollars generally are not. (irs.gov)
5. Medicare.gov, Open Enrollment: October 15 through December 7, with changes effective January 1; Medicare Advantage Open Enrollment January 1 through March 31. (medicare.gov)