Open Enrollment: the 45 Minutes Worth Thousands

Open enrollment is the annual 45 minutes when high earners set thousands of dollars of outcomes with the least attention of their financial year, defaulting last year's elections forward while premiums, plan designs, and family circumstances all changed. The high-leverage clicks: the health plan comparison, the HSA harvest, the disability election, and the handful of voluntary benefits that are quietly excellent or quietly worthless.

The Health Plan Math, Done Honestly

Compare total annual cost, not premiums: (your premiums) plus (expected out-of-pocket at your family's realistic usage) minus (employer HSA/HRA contributions), computed for both a low-usage and a high-usage year. The high-deductible plan frequently wins both scenarios for healthy families once premium savings and employer HSA dollars are counted, and its worst case, hitting the out-of-pocket max, is often within a couple thousand of the PPO's worst case. The tiebreaker is the HSA itself: eligibility for the only triple-tax-free account is worth real money annually. Families with predictable heavy usage, ongoing therapies, expected births, chronic conditions, should run the same math; the PPO earns its premium sometimes, but only arithmetic knows when.

The Protection Elections

Supplemental long-term disability, buying coverage from 50-60% up toward 70%, is usually the best value on the menu, though it inherits group-plan limitations; take it and still consider individual coverage. Supplemental group life is convenient but priced for the average enrollee; healthy applicants usually beat it with individual term, use group amounts as a bridge, not the plan. Legal plans (~$200/year) pay for themselves in any year you execute estate documents, one deliberate year of enrollment can fund the whole document set. Accident, hospital-indemnity, and critical-illness policies are lottery tickets with poor odds for the well-reserved; a funded emergency fund makes them redundant.

FSAs, Dependent Care, and the Calendar Traps

Health FSAs are use-it-or-lose-it (small carryovers allowed) and incompatible with HSA contributions except as limited-purpose (dental/vision) versions, HDHP families should elect limited-purpose or none. The dependent-care FSA ($5,000 household cap) is nearly free money for families already paying for daycare or after-school care, at high brackets it beats the childcare credit; coordinate, not both on the same dollars. Commuter benefits, backup-care days, and employer 529 matches are small but real; claim what matches your actual life.

The Ten-minute Wrap-up

While the portal is open: confirm beneficiaries on the 401(k) and group life (they override wills and drift out of date), revisit deferral percentages against the new year's limits, capture any HSA/401(k) match mechanics that changed, and calendar mid-year qualifying events (birth, marriage, job change) that reopen elections. Bring the confirmation statements to your planner; open enrollment is one of the four annual moments, with tax season, raises, and year-end, when a plan actually gets executed.

Tony Colunga · Founder, Attend Wealth

Tony leads Attend Wealth, a fee-based wealth management firm in Atlanta serving professionals, families, and business owners. Advisory services are held to a fiduciary standard. More about Attend