Open Enrollment Checklist: How to Pick the Right Health Plan at Work

Before You Start: Gather Your Data

Pull up last year's healthcare spending. Check your insurance company's portal or your bank statements and add up: total premiums paid, doctor visits and specialist visits, prescriptions filled, any procedures or lab work, and how much you spent out-of-pocket. This is your baseline — the number your new plan choice needs to beat.

Understand Your Plan Options

PPO (Preferred Provider Organization): Most flexibility. See any doctor, no referrals needed, out-of-network coverage available (at higher cost). Higher premiums but lower out-of-pocket when you use care. Best for people who see specialists regularly or want maximum choice.

HMO (Health Maintenance Organization): Lower premiums but you must stay in-network and get referrals for specialists. Best for healthy people who have a primary care doctor and rarely need specialists.

HDHP (High Deductible Health Plan): Lowest premiums, highest deductibles. In 2026, the minimum deductible is $1,700 (individual) or $3,400 (family). Pairs with an HSA for triple tax savings. Best for generally healthy people who want to minimize monthly costs and invest through an HSA.

The Real Comparison: Total Annual Cost

Don't just compare premiums. Compare total annual cost = premiums + expected out-of-pocket expenses.

A plan with a $400/month premium and $500 deductible costs you $5,300/year if you hit the deductible. A plan with a $250/month premium and $3,000 deductible costs you $6,000/year if you hit that deductible — but only $3,000/year if you stay healthy. If you rarely use healthcare, the HDHP might save you $2,300.

HSA vs. FSA: The Decision Tree

Choose an HSA if you're on an HDHP. In 2026, you can contribute $4,400 (individual) or $8,750 (family), all tax-deductible. The money rolls over forever, grows tax-free, and follows you if you leave the job. Many financial advisors rank HSAs as the best tax-advantaged account available — better than a Roth IRA for healthcare expenses.

Choose an FSA if you're not on an HDHP and have predictable medical costs. 2026 limit is approximately $3,300. But it's mostly use-it-or-lose-it, so only contribute what you're confident you'll spend.

Check Your Providers

Before switching plans, verify that your current doctors are in-network on the new plan. Check your primary care physician, any specialists you see regularly, your preferred pharmacy, and any hospitals or urgent care centers you use. Switching plans to save $50/month isn't worth it if it means losing a doctor you trust.

Don't Forget Dental and Vision

Dental insurance typically costs $10–$30/month and pays for itself with just two cleanings a year (valued at $150–$300 each). Vision insurance is $5–$15/month and worth it if you wear glasses or contacts. Both are usually cheap enough to just enroll.

The 15-Minute Open Enrollment Action Plan