Every fall, millions of Americans click through open enrollment in under 20 minutes and lock in thousands of dollars of consequences for the year. Employer windows mostly run October–November; ACA marketplace enrollment runs November 1 to mid-January in most states. Here's the decision framework worth those 20 minutes.
The core choice: HDHP + HSA vs PPO
- Pick the math, not the fear. Add each plan's annual premium to its worst-case out-of-pocket maximum. Surprisingly often, the high-deductible plan wins even in a bad year once the premium gap and employer HSA contribution are counted.
- The HSA is the best tax account in America: deductible going in, tax-free growth, tax-free out for medical costs — and payroll HSA contributions even skip FICA. 2026 limits: $4,400 self-only / $8,750 family.
- PPOs earn their premium when you have ongoing specialists, planned procedures, or medications that would blow through the HDHP deductible anyway — estimate your real usage from last year's claims history.
FSA: powerful but booby-trapped
Health FSAs (for those without an HSA-eligible plan) shelter about $3,400 pre-tax in 2026, but most plans forfeit unspent money past a small carryover — fund it to your predictable expenses (glasses, dental work, copays), not your hopeful ones. Dependent-care FSAs (up to $7,500) are separate and huge for daycare families.
The commonly-skipped checkboxes
- Disability insurance — group LTD at 50–60% of income is cheap and underrated; check whether you need a supplemental amount.
- Supplemental life insurance — compare the group rate against an individual term quote; healthy people often beat the group price outside. Size the need with the life insurance calculator.
- 401(k) contribution refresh — enrollment season is the natural moment to push your rate up 1%; see what it does to your paycheck with the paycheck calculator and to retirement with the 401(k) calculator.
One hour with last year's claims and this framework typically beats defaulting to last year's elections — plans change under you even when you don't change plans.