Please open the boring benefits email

ISSUE #46 • MONDAY, NOVEMBER 2, 2026 • 5 MIN READ

Good morning. Welcome back to Still Monday. Somewhere in your inbox is an email with a subject like “2027 BENEFITS ENROLLMENT INFORMATION.” It looks boring because HR has discovered the perfect camouflage for thousands of dollars.

This is one of the few times a year when twenty minutes of reading can materially change your household finances.

Please resist the urge to archive responsibly.

KFF's 2026 employer health benefits survey puts the average annual premium for family coverage at $28,303. Workers contribute an average of $7,471, up $621 from 2025. Single coverage averages $9,804. KFF

For many households, health coverage is one of the largest financial decisions made with the least attention. People will spend three evenings comparing televisions and fourteen minutes selecting a health plan that can change annual spending by thousands.

Benefits documents are written in a dialect negotiated between lawyers and spreadsheets. Premium. Deductible. Coinsurance. Out-of-pocket maximum. HSA. FSA. PPO. HDHP. By page eight, a normal person is willing to pay anything to stop reading.

Marsh says employers expect health-benefit costs per employee to increase an average 8.2% in 2027, the highest projected increase since 2003 even after planned cost controls. Without changes, employers said costs would rise about 11%. Marsh

That does not mean your premium will rise 8.2%. Employers can absorb some cost, change plans, increase deductibles, alter networks or shift more of the premium to employees. It means the default choice deserves inspection.

Start with expected total cost, not the premium alone. Multiply your paycheck deduction by the number of pay periods. Add the deductible you are realistically likely to use. Check prescription costs, specialist copays and whether your doctors remain in network. Then subtract employer HSA contributions or other credits.

For people eligible for HSAs, the IRS set 2027 contribution limits at $4,500 for self-only coverage and $9,000 for family coverage. IRS

There is no universally best option. There is a best option for your expected usage, cash-flow tolerance and risk. The boring email is asking you to decide all of that before Friday.

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The average family premium is now $28,303. Your employer may pay most of it, but it still belongs in your mental picture of total compensation.

KFF found workers at smaller firms contribute a larger share of family premiums on average than workers at larger employers. Company size can materially change the value of the same salary offer.

Many employers require employees to re-elect flexible spending accounts each year. Check your plan instead of assuming last year's choice follows you into 2027.

For each health plan, estimate a low-use year, a normal year and a bad year. Compare annual premiums plus likely out-of-pocket spending in each scenario. Then look at the worst-case number: premium plus out-of-pocket maximum.

You are buying both healthcare and financial risk protection. Compare both.

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Check employer HSA contributions, retirement matches, wellness credits and any benefits that require an election. A benefit you forget to activate is compensation your company budgeted and you declined by accident.

This is one of the rare financial tasks where procrastination can literally change the paycheck.

HR: Please carefully review 73 pages of benefits information.

EMPLOYEE: When is it due?

HR: Friday.

EMPLOYEE: I will make an informed decision.

EMPLOYEE, FRIDAY 4:57 PM: Same as last year.

The default option is still a financial decision. It just happens without the satisfying feeling of making one.

Vote below and tell us how you choose benefits: spreadsheet, spouse, HR webinar, last year's plan or pure panic.

Technically Monday. Emotionally reading the deductible.

— The Still Monday Desk