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 many people use to get to a good answer without disappearing into a 60-page PDF. The specifics depend on your situation, and plan designs and figures change year to year.
Minutes 0–5: Pulling last year's numbers
A common first step is to open your insurer's portal and find your total claims and total out-of-pocket for the past 12 months. Many people find that's the single most useful number for predicting next year's spend. If you're new to the company, some people estimate based on doctor visits, prescriptions, and any planned procedures.
Minutes 5–15: Picking the health plan
Many people compare HDHP and PPO using last year's actual claims. A break-even pattern people often look at:
- 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. Which plan fits best depends on your own claims and your family's situation.
Minutes 15–20: Funding the right tax-advantaged account
- HSA (paired with HDHP): Many people contribute up to the IRS limit if they can afford it. The IRS treats the HSA as the only account that gets a triple tax advantage, and HSA balances generally roll over indefinitely (per IRS Publication 969). The annual contribution limits are set by the IRS and change each year.
- FSA (paired with most PPOs): A common approach is to estimate predictable medical spend (glasses, copays, planned procedures) and fund only that. The IRS generally treats most health FSA funds as use-it-or-lose-it at year-end, though some plans offer a limited carryover or grace period — your plan's terms may differ.
- Dependent Care FSA: For people with kids in daycare, this often saves real tax dollars. Many people fund close to the cap, which the IRS sets separately from the health FSA limit.
Minutes 20–25: Life and disability insurance
- Basic life (1–2× salary) is usually free, so many people accept it.
- Supplemental life is worth a look if you have dependents and no other coverage. Some people compare the group rate to a term-life quote outside work before deciding.
- Short-term and long-term disability: If your employer offers a buy-up, many people find the math favors taking it. Disability is one of the most under-bought protections.
Minutes 25–30: The "easy to forget" line items
- Beneficiary designations: A common step is to 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, and many people skip them unless they have a specific need.
What should you 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, so it often helps to confirm yours.)
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.). For the current HSA and FSA rules and contribution limits, many people check the source directly in IRS Publication 969 (Health Savings Accounts and Other Tax-Favored Health Plans).