Carrie Schwab Pomerantz

Dear Readers: As more and more of the boomer generation heads toward retirement, I get a lot of age-related questions. Can I tap into my 401(k) early? When should I take Social Security? Should I apply for Medicare if I'm still working? The answers all have to do with certain dates and deadlines that you'll want to keep in the top of your mind. 

While you may think by the time you reach your 50s you've passed most of life's major milestones, think again. From 55 on, there are a number of age-related financial milestones that you can't afford to ignore, no matter how young you feel. Miss them and you'll not only miss some of the perks that come with getting older, you may also be penalized for your lack of attention.

So before you declare that you'll never acknowledge another birthday, at least put these ages on your mental calendar -- and keep this checklist handy. 

Age 55: Possible penalty-free early 401(k) distribution.

If you're 55 or older and lose or leave your job, you can take a lump-sum distribution from your 401(k) under what's called separation of service, without paying a 10 percent early withdrawal penalty. And just for the record, if you leave your company before age 55, you can still set up a schedule of "substantially equal payments" and avoid the penalty. You will, however, pay income taxes on either type of distribution.

Age 59 1/2: Penalty-free withdrawals from any of your retirement accounts.

Whatever type of retirement account you have -- IRA, 401(k), 403(b), SEP, SIMPLE, you name it -- at 59 1/2 you can begin making withdrawals penalty free. Once again, you'll pay income taxes on the earnings and any contributions that were tax deductible. However, in the case of a Roth IRA, if you've held it for five years, contributions and earnings are tax free, as well as penalty free. 

Age 62: Early Social Security benefits.

This is the soonest you can file for Social Security, unless you're disabled. But if you do, your benefits will be permanently reduced by approximately 25 percent. Plus, benefits will be further reduced if you're still working and earn beyond a certain limit. You can apply for Social Security when you're within four months of the first full month you turn 62. However, this may not be the wisest choice. has a convenient online calculator to help you determine the best time for you to start benefits. 

Age 65: Eligible for Medicare.

Carrie Schwab Pomerantz

Carrie Schwab Pomerantz is a Motley Fool contributor.

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