19 | STAY INSURED Leaving your job next year? Switch to the lowest-cost plan during this year's open enrollment. Then, after you quit, federal rules (known as COBRA) will let you stay on your employer's health plan for up to 18 months, although you'll usually have to pay the full cost, plus 2%. Once you've tapped out COBRA, you must sign up for a new policy within 63 days or insurers can legally turn you down or refuse to cover pre-existing conditions.
20 | BE FLEXIBLE Add up your co-pays, deductibles and other out-of-pocket medical expenses from last year to figure out how much to put into your flexible spending account (your benefits department can tell you what's eligible). For every $1,000 you put in, you'll slash about $300 in taxes.
21 | DON'T LOSE IT You'll forfeit any funds in your FSA that you don't use by the end of the year or by March of the following year (depending on your company). Need to get rid of some bucks? Stock up on over-the-counter medical supplies like Band-Aids, cold and flu tablets and aspirin; order a six-month supply of contact lenses and solution; or schedule an extra session with your shrink, if you've exceeded the number of therapist visits covered by your health plan.
22 | GAME THE SYSTEM If you're close to the dollar limit for doctor or, more likely, dental visits in a calendar year, book half your appointments in December and the rest in January.
23 | TAKE THE WRITE-OFF The IRS allows you to deduct medical bills that exceed 7.5% of your gross income. That's a high bar, but the list of eligible expenses is extensive, including insurance premiums, dental X-rays, fertility treatments, prescribed weight-loss and stop-smoking programs and even LASIK eye surgery. See irs.gov/publications/p502 for the details.