Roadblock #3: No health insurance

The problelm: Nearly half of large companies do not offer health insurance to their retirees, reports HR consulting firm Towers Perrin. And just a fraction of small companies provide this benefit. So if you'd hoped to quit before 65, when Medicare kicks in, you could be on your own for insurance.

Going without may be the quickest way to blow your nest egg. But buying coverage will take out a bite out too: According to the Kaiser Family Foundation, couples ages 50 to 64 in individual market plans spend an average $8,670 on premiums, and out-of-pocket costs in such plans run $2,690 (in total, a quarter of the suggested 4% yearly draw on a $1 million portfolio!).

Of course, you'll be lucky to get covered at all if you have any pre-existing conditions. Sure, as of 2014, insurers will be barred from denying coverage or pricing based on health. But if you'd like to retire in the meantime? There's no magic bullet.

Solution #1: Go with a group. If your job won't insure you, see if your spouse's will, as the coverage might be subsidized. No luck? Even if your company doesn't offer retiree benefits, you can continue in its group plan for 18 months under the COBRA law. Typically you foot the full premium, but it's often still cheaper than a comparable individual market plan. Note: You must enroll within 60 days of retirement.

Solution #2: Work around the costs. If you'll run out of COBRA before age 65, you might take on freelance or consulting work. Not only will this help pay the bills, but you can also deduct individual health insurance premiums up to the amount of your profit on your 1040, says Carolyn McClanahan, a Jacksonville financial planner.

Note: If you're taking Social Security early, your benefit will be reduced once you earn over $14,160. But you'll then get a higher payment at full retirement age. Before retiring, talk to an independent insurance agent to see if you can get coverage, and if so, what costs to expect.

Solution #3: Pay more out of pocket. "Work" and "retirement" don't go together for you? Get a sense of your options from an agent, and use the T. Rowe Price Retirement Income Calculator at to see if you can afford the costs on your expected draw.

You'll pay lower premiums if you accept a higher deductible. With some high-deductible plans, you can set aside pretax dollars in a health savings account to cover those additional costs. And if you're denied coverage or priced out? Keep working until 2014 or you're Medicare-eligible -- whichever comes first.