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Think You're Ready to Retire? 6 Things to Consider

There's a question many 50- and 60-somethings may ponder today as the economy teeters on the edge of recession, retirement nest eggs fail to grow amid a down stock market, and health care costs keep rising as they have done just about every year:

Should I retire around 65 or work a bit longer?

It's not an easy decision, given life's uncertainties. Sure, the thoughts of taking that cruise with your spouse, or maybe playing golf twice a week, fill your head with happy thoughts. But can a life of leisure also make one miserable?

Some people are hitting their 50s and 60s today and either working at or searching for "that one thing" that can boost their sense of fulfillment. In some circles, the one thing is called an "encore career" or "encore job," a later-in-life career change to a field or position that more closely aligns with their interests and passions.

If you're close to retirement or facing it within a decade or two (heck, even if you're already retired and wondering why), here are six questions you must ask yourself to determine where you want to go:

1. Am I doing what I like to do or what I feel I have to do?
If you're a Baby Boomer (born between 1946 and 1964), you probably thrive on accomplishment. Does your current job give you that sense of accomplishment? If not, what kind of job would? If it pays less, and you can absorb the financial hit, think about making a switch to an encore career.

2. What do I (or would I) really like in a workplace? Is it the work? The people? Working inside? Outdoors?
How we like to work can be just as important as where, and it can color our views of our current situation. If, for instance, you hate being stuck in a cubicle all day but like being around people, you may want to consider a change. I've met people past retirement age who worked part-time driving airport limousines because they like being on the road and meeting people.

3. What work skills can transfer to another role?
Are you adept at using many software applications? Windows and Mac operating systems? Do you excel at managing your time well? Prioritizing work? Can you communicate effectively? Many employers want these as much as they want someone with the raw skills to do the job.

4. What shape are you in? (Really!)
If a job requires you to be on your feet for most of the day, or commute a long distance, can your legs, hips, and back handle it? How's your vision? This will be critical if the job requires a lot of reading, driving, or just observation. Although you might like to think otherwise, you're not getting younger. Remember that growing up is optional, but growing old is mandatory. If your present job is starting to cause physical difficulties, a change might alleviate those problems.

5. What shape are you in financially?
Retirement portfolio aside, do you have enough saved to cover three to six months of living expenses, more if you reduce your income by taking a lower-paying job? As for your retirement portfolio, be sure - if you decide to retire - that you have enough that you can add to Social Security to cover about 80% of your current income. If not, best to stay in the job market, at least part time. Investment and financial advice sites have online tools that can help determine your portfolio's future value based on how you invest it.

6. Got good health insurance?
Here's the potential 800-pound gorilla. Does (or will) Medicare provide enough to cover your prescriptions and doctors' visits? Will you need supplemental insurance? Would long-term care insurance make sense to protect your assets if you or your spouse should need more expensive medical care? Also, pay close attention to changes in either the delivery of health care or health insurance in the U.S. now that there's a growing will in both major political parties to change the system.

If, after answering these questions, you decide it's time for an encore, go ahead and update your resume and launch a job search.

Calling all retirees, near retirees, and those merely thinking about retirement! What other issues come into play when you think about life after your last paycheck? Share your views with us.

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