First, consider the following: unless you have a significant, catastrophic-type medical claim, it is unlikely that you will recoup the amount of money you pay in employee contributions for traditional plans (such as a PPO) or even Health Reimbursement Accounts (HRAs).

For example, assume you contribute $550 a month for family coverage, which amounts to $6,600 per year (12 x $550). We’ll come back to this figure. Now, if your family has three doctor visits during the year at $200 each ($600 total), plus four prescriptions at an average of $75 ($300 total), that's a total of covered expenses for the year of $900. Assuming the co-payments for each of the three doctor visits was $20 (3 x $20 = $60) and each of the four prescriptions was $30 (4 x $30 = $120), you will pay $180 out of pocket, taxed. Now let’s look at the whole picture. Your insurance paid for $720 of your $900 in costs. You paid $180 — taxed — along with $6,600 in contributions. 

Compare the numbers of your available plans. The HDHP usually offers lower premiums in exchange for the higher deductible, including the same coverage for significant health expenses as with the more expensive traditional plans. You pay for costs below the deductible with tax-free dollars and employer contributions, if offered, and keep and grow the funds you don’t use each year.