1. Counting any income from investments, pensions, spouse, etc., and given your life expectancy, can you financially afford to retire? Not sure? See an accountant.
2. Do you have a physical or mental health problem(s) that makes retirement wise?
3. If you're currently working, would your next decade feel more rewarding on the job or away from it?
4. If you're unemployed, are your prospects of landing a good-enough job so poor that it would be wiser to spend that job-search time in retirement?
5. If you were to land a job, do you believe you'd do well-enough at it, or would it be cosmically wise to let someone else take the position?
6. Do you have or will you likely find activities to keep you sufficiently busy for the rest of your life: for example, volunteering, hobbies, classes, friends, family activities and responsibilities, including helping others with their health problems?
7. Whether or not you have sufficient activities to fill your time, are you likely to feel okay about ending your paid employment?
8. if you retire, you'll be spending much more time with the person(s) you live with. Would that person(s) and you welcome or resent that?
9. Would retiring give you the freedom to move to a geographic location that you and your partner (if any) would prefer?
10. Would your wiser twin tell you to retire?
Obviously, deciding whether to retire is a huge decision. Take your time. Discuss your answers to these questions with people you trust. And then let all their input float around in your head until you become clear on what's right for you. Remember that although there are exceptions, retirement, alas, tends to be like the Roach Motel: You can check in but you can't check out.
Marty Nemko's bio is in Wikipedia.