Open enrollment is usually two weeks long, but most of the decisions you'll make are reversible only once a year. Here's a 30-minute plan that gets you to a good answer without disappearing into a 60-page PDF.
Minutes 0–5: Pull last year's numbers
Open your insurer's portal and find your total claims and total out-of-pocket for the past 12 months. That's the single most useful number for predicting next year's spend. If you're new to the company, estimate based on doctor visits, prescriptions, and any planned procedures.
Minutes 5–15: Pick the health plan
Compare HDHP and PPO using last year's actual claims. The break-even rule:
- If your claims came in below the HDHP deductible, the HDHP usually wins on annual premium savings alone.
- If you exceeded the PPO deductible last year, the PPO usually wins on predictability.
- If you're in between, the employer's HSA contribution often tips it.
See our HDHP vs PPO guide for the full break-even math.
Minutes 15–20: Fund the right tax-advantaged account
- HSA (paired with HDHP): Contribute up to the IRS limit if you can afford it. The HSA is the only account that gets a triple tax advantage and rolls over forever.
- FSA (paired with most PPOs): Estimate predictable medical spend (glasses, copays, planned procedures) and fund only that. FSA funds usually expire at year-end.
- Dependent Care FSA: If you have kids in daycare, this saves real tax dollars — fund close to the cap.
Minutes 20–25: Life and disability insurance
- Basic life (1–2× salary) is usually free — accept it.
- Supplemental life is worth a look if you have dependents and no other coverage. Compare the group rate to a term-life quote outside work.
- Short-term and long-term disability: If your employer offers a buy-up, the math usually favors taking it. Disability is one of the most under-bought protections.
Minutes 25–30: The "easy to forget" line items
- Beneficiary designations: Confirm your 401(k), life insurance, and HSA beneficiaries are current. After a marriage, divorce, or birth, this is the single most-skipped update.
- Commuter benefits: Pre-tax transit and parking — easy to add.
- Voluntary benefits: Legal plans, pet insurance, identity theft — usually optional, usually safe to skip unless you have a specific need.
What to ask HR
- Are there changes to plan design or networks this year?
- Has the employer HSA contribution changed?
- What's the deadline, and what happens if I miss it? (Most plans default you to last year's choices — but not all.)
The Department of Labor maintains a plain-language summary of common benefits — DOL benefits and leave overview (affiliate link — OffbookHR may earn a commission if you buy through this link. It does not affect ranking.).
This page reflects general information and is not tax, insurance, or legal advice. Consult a licensed benefits advisor or your HR team for guidance specific to your plan.