The Dad's Guide to Open Enrollment

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.

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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. Deductible. 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. For families, there's usually an individual and a family deductible.

3. Out-of-pocket maximum. 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. Copay 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. 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 plan looks scary because the deductible is $2,000-3,000 instead of $500. 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 $8,550 to an HSA Source: IRS.gov HSA Contribution Limits . That's $8,550 of income that's never taxed. If you're in the 22% tax bracket, that's roughly $1,880 in 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.

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 directory for any plan you're considering.

Are your prescriptions covered? Check the formulary. 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. 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.