Every fall your employer sends you an email that says something like "Open enrollment closes November 15th. Review your benefits." And every fall you skim it, pick the same plan you had last year, and move on.
That autopilot decision might be costing you $1,000-3,000 a year. Health plans change. Your family's needs change. The math that worked last year might not work this year. And unlike most financial decisions, you only get to make this one once a year. Miss the window and you're stuck for 12 months.
Here's how to actually compare your options in about 30 minutes.
Download the benefits comparison worksheet
Side-by-side plan comparison. Built-in formulas for total annual cost. HSA vs FSA calculator included.
Get the worksheet (free)The 5 numbers that matter
Every health plan has about 40 line items in the summary of benefits. You need to compare 5 of them. The rest are noise for this decision.
1. Monthly premium. What you pay per paycheck. Multiply by the number of pay periods (usually 24 or 26) to get the annual cost. This is the most visible number but often the least important one.
2. DeductibleDeductible:What you pay for covered care each year before your health insurance starts sharing the cost.. How much you pay out of pocket before insurance starts covering things. A $500 deductible means you pay the first $500 of medical bills yourself.[1] For families, there's usually an individual and a family deductible.
3. Out-of-pocket maximumOut-of-pocket maximum:The most you will pay for covered care in a plan year. After you hit it, the plan pays 100% of covered costs.. The most you'll ever pay in a year. Once you hit this number, insurance covers 100%. This is your worst-case scenario number. For families with young kids who visit the ER occasionally, this number matters more than the premium.
4. CopayA fixed dollar amount you pay for a covered health service. Example: $25 for a primary care visit, $50 for a specialist. You pay this at the time of the visit regardless of your deductible. for common visits. What you pay for a regular doctor visit, specialist, and urgent care. If your family goes to the pediatrician 8-12 times a year (normal for families with young kids), the copay difference between plans adds up fast.
5. HSA eligibility. High-deductible health plans (HDHPs) let you open a Health Savings Account. This is tax-free money for medical expenses that rolls over every year.[5] It's one of the best tax advantages available to families. See our HSA guide for the full breakdown.
The formula most people miss
Don't just compare premiums. Compare total annual cost under three scenarios:
Best case: Annual premium + maybe 2-3 doctor visits. This is the year nobody gets hurt, nobody needs surgery, just routine checkups and a couple sick visits.
Typical case: Annual premium + deductible + copays for 8-12 visits + one urgent care trip + prescriptions. This is what a normal year with young kids actually looks like.
Worst case: Annual premium + out-of-pocket maximum. This is the year someone breaks an arm, needs an ER visit, or has a baby. Your total cost is capped at premium + OOP max.
The worksheet calculates all three scenarios for each plan. The plan with the lowest "typical case" number is usually the right choice. The plan with the lowest "worst case" number is the right choice if you're risk-averse or expecting a big medical year (pregnancy, planned surgery).
The HDHP + HSA play
A high-deductible planHDHP (High-Deductible Health Plan):A health plan with a higher deductible and lower premiums that meets the IRS minimums, which makes you eligible for an HSA. For 2026 the minimum deductible is $1,700 for self-only and $3,400 for family coverage. looks scary because the family deductible has to be at least $3,400 in 2026, instead of something like $500.[2] But the premium is usually $200-400/month cheaper. That savings goes into your HSA, which is tax-free going in, tax-free growing, and tax-free coming out if used for medical expenses.
For 2026, families can contribute up to $8,750 to an HSAHSA (Health Savings Account):A tax-advantaged account for medical costs, open only to people on a qualifying high-deductible health plan. Contributions are pre-tax, growth is tax-free, and withdrawals for medical expenses are tax-free.Learn more →[2]. That's $8,750 of income that's never taxed. If you're in the 22% tax bracket, that's roughly $1,925 in federal income tax savings alone. Plus the money can be invested and grow tax-free forever.
The worksheet has a separate tab that models the HDHP + HSA math against a traditional PPO. For most healthy families, the HDHP wins. For families with chronic conditions or planned surgeries, the PPO sometimes wins. Run the numbers. The spreadsheet does the hard part.
Example: PPO vs. HDHP side by side
Numbers are easier than concepts. Here's what two real-ish plans look like when you run the math for a family of four with one employed parent.
| PPO Plan | HDHP + HSA | |
|---|---|---|
| Monthly premium | $650 | $380 |
| Annual premium | $7,800 | $4,560 |
| Deductible (family) | $500 | $3,400 |
| Out-of-pocket max | $6,000 | $7,050 |
| Copay (primary care) | $25 | $0 after deductible |
| HSA eligible | No | Yes ($8,750 limit) |
Now run the three scenarios:
| Scenario | PPO total cost | HDHP total cost | Winner |
|---|---|---|---|
| Best case (3 checkups) | $7,875 | $4,860 | HDHP saves $3,015 |
| Typical year (10 visits + urgent care) | $8,550 | $7,160 | HDHP saves $1,390 |
| Worst case (hit OOP max) | $13,800 | $11,610 | HDHP saves $2,190 |
*Totals are premiums plus out-of-pocket costs. They leave out the HSA tax savings, which would make the HDHP column cheaper still. The worksheet models this for your exact bracket.
In this example the HDHP wins in every scenario. That's common for healthy families. But if your family has a chronic condition that needs frequent specialist visits before hitting the deductible, PPO can win on the typical-year math. Plug in your real numbers before deciding.
Benefits most dads skip over
Health insurance gets all the attention during open enrollmentOpen enrollment:The yearly window, usually in the fall, when you can pick or change your employer benefits. Outside it, you can only change after a qualifying life event, such as having a baby.Learn more →. But there are five other benefits buried in the packet that most dads either ignore or accept the defaults on. That's leaving money on the table.
Employer life insurance. Most companies give you 1x salary for free. Always take it. But don't confuse this with real coverage. If you make $90K, your family needs $900K-1.3M in coverage, not $90K. Employer life insurance also disappears the day you leave the company. Get a separate term life policy for the full amount. Work out your own number with the life insurance calculator.
Dependent care FSADependent Care FSA:An employer account for childcare costs (daycare, preschool, after-school care, day camp) for kids under 13, paid with pre-tax money. The federal limit rises to $7,500 per household in 2026, but your employer's plan may set a lower cap.. If you pay for daycare, preschool, or after-school care, you can set aside pre-tax money for it. The federal limit rises from $5,000 to $7,500 per household in 2026, but your employer's plan can set a lower cap, so check the enrollment packet.[3] At a 22% bracket, $7,500 saves about $1,650 in federal income tax. If your childcare costs that much (it almost certainly does), max it out. This is separate from your health FSA.
Short- and long-term disability. Most dads think about dying but not about getting hurt. The Social Security Administration estimates that more than 1 in 4 of today's 20-year-olds will become disabled before reaching retirement age[4]. Long-term disability insurance replaces 50-60% of your income if you can't work. Some employers offer it free. Others charge $10-30/month. If the option exists, take it.
Legal plan. Some employers offer prepaid legal plans for $10-20/month. Sounds useless until you need a will, a real estate closing, a name change, or a dispute with a contractor. If you don't have a will yet (and you should — see our emergency binder guide), a legal plan pays for itself the first time you use it.
Vision and dental. These are usually cheap ($5-15/month each) and they cover the stuff that adds up quietly: two cleanings a year, glasses or contacts, kids' orthodontics. Dental plans especially tend to have low premiums relative to what you get. If the premium for family dental is under $40/month, it's almost always worth it.
Things to check before you click "enroll"
Is your doctor in-network? Plans change networks. Your pediatrician might have been in-network last year and out-of-network this year. Check the provider directoryYour insurance company's list of approved doctors, hospitals, and specialists. In-network providers have pre-negotiated rates. Out-of-network providers cost significantly more or may not be covered at all. for any plan you're considering.
Are your prescriptions covered? Check the formularyYour insurance plan's list of covered prescription drugs, organized by tier. Tier 1 (generics) = cheapest. Higher tiers = more expensive. A drug not on the formulary may cost full price.. That $20 generic might jump to $80 on a different plan. If anyone in your family takes regular medication, this is a big variable.
Did your employer add or remove plans? Sometimes a new plan option shows up that's better than everything else. Sometimes the plan you're on gets worse. Read the whole email, not just the "your current plan" section.
Did your family change? New baby? Kid turning 26 and aging off your plan? Spouse got a new job with their own insurance? These changes shift which plan makes sense.
Do this right now
If open enrollment is approaching: download the worksheet, pull up your benefits guide, and spend 30 minutes comparing. Don't just look at health plans — check the five benefits above that most people skip. If open enrollment already passed: bookmark this and set a calendar reminder for October. Next year, you'll be ready.
And while you're thinking about benefits, make sure you're not leaving money on the table with your HSA or your life insurance.
Get the comparison worksheet
Side-by-side. Three scenarios. HSA calculator. All formulas built in.
Download now (free)References
- HealthCare.gov, Glossary: deductible, out-of-pocket maximum, copayment. healthcare.gov/glossary/
- IRS, Revenue Procedure 2025-19: 2026 HSA contribution limits and HDHP minimum deductibles. irs.gov/pub/irs-drop/rp-25-19.pdf
- 26 U.S. Code § 129, Dependent care assistance programs (exclusion limit $7,500 as amended by Pub. L. 119-21, for tax years beginning after Dec. 31, 2025). law.cornell.edu/uscode/text/26/129
- Social Security Administration, Disability Facts poster: "More than one in four 20-year-olds will become disabled before reaching retirement age." ssa.gov/disabilityfacts/materials/pdf/poster-1.pdf
- IRS, Publication 969: Health Savings Accounts and Other Tax-Favored Health Plans. irs.gov/publications/p969
