How will I cover health insurance? Finding affordable coverage might get easier once Obamacare kicks in next year, but for now you could face some sticker shock if you're younger than 65 (the age when you become eligible for Medicare). If you have employer coverage now, you may be able to extend it via COBRA, but you'll pay the full cost -- not the subsidized fraction you probably pay now. Getting a policy on your own is another option if you're in good health, but people with even minor health problems can find it tough to get coverage and may need to resort to a state high-risk pool. (You can start your search at HealthCare.gov.) Other options include coverage through a spouse or through a professional, alumni or religious organization. Don't go without coverage if you can possibly avoid it, since you would be just one accident or illness away from bills that could bankrupt you.

What will I do next? Ideally, you won't just be running away from a bad situation. You'll be running toward something better. In retirement, the people who are happiest tend to be the ones who have a passionate or sustaining interest in something -- and that something probably isn't playing golf, said Ralph Warner, the author of the excellent book "Get a Life: You Don't Need A Million to Retire Well." If you're not done with work, check out the classic book "What Color is Your Parachute?" for good advice about how to get to the next stage.

What do the people around me say? Your friends and family can provide valuable feedback about whether it's time to move on -- as long as you discount the opinions of the fraidy-cats who abhor any risk and think all change is for the worse. Those who love you also may be able to identify problems you may be ignoring that could be affecting your decision-making, such as depression, anxiety or other health issues. If your job is causing those problems, on the other hand, the people around you could bring that to your attention as well.

What solutions am I overlooking? Another area where your tribe can help you is brainstorming solutions that don't require leaving your job. You may be able to transfer away from a bad boss, for instance, or get help from human resources or a mentor in managing the relationship. If you feel you're being overlooked or your skills aren't being fully utilized, you can ask for new challenges and opportunities to grow. If you're contemplating retirement, you could consider phasing out slowly by moving to part time, or trying the "practice retirement" that Fahlund suggests: Continue to work, but cut back on saving so you can start taking trips, indulging hobbies and doing the other stuff you planned to do in retirement. Working even a few years into your 60s can dramatically increase your retirement benefits, Fahlund said, even if you don't add much to your savings.

Then again: If it's time, it's time. If the idea of quitting fills you with joy, rather than apprehension, that's a pretty good sign you should find a way to follow through.

Patricia Joseph of Pittsburgh was 63 and about to take a monthlong leave of absence from her job as a college professor when she realized she didn't want to conduct the research she had planned -- or to go back to work afterward.

"Within 2 weeks, I submitted my retirement letter," Joseph wrote. "I was DONE!"

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Liz Weston is the Web's most-read personal-finance writer. She is the author of several books, most recently "The 10 Commandments of Money: Survive and Thrive in the New Economy" (find it on Bing). Weston's award-winning columns appear every Monday and Thursday, exclusively on MSN Money. Join the conversation and send in your financial questions on Liz Weston's Facebook fan page.

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