A deductible is the amount of money you and only you must pay out-of-pocket for healthcare services before your insurance starts contributing. For example, if you have a $1000 deductible, you’d pay the first $1000 of your medical bills before insurance kicks in. But reader beware: some insruance plans have multiple deductibles (like for prescriptions or out-of-network care), and not all expenses (like premiums or cosmetic treatments) count toward your deductible.