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There are two kinds of readiness: emotional and financial. If you are burned out and sick of everything about your job, you are emotionally ready. If you have been saving money and investing wisely since your first job, you are probably financially ready. To be sure, ask yourself these five questions.

1. Can you afford to retire based on the money or investments you have?
A general rule of thumb for retirement planning is that you should have, at least, 70 to 80 percent of the yearly salary you earned while you were working.
2. How much money will you need to live close to the lifestyle you’re living now?
Take a hard look at your current expenses. Then, add up all your sources of income—Social Security, savings accounts, investments, pension, 401(k). If what you need is far more than what you have, consider postponing retirement.
3. How healthy are you and your spouse if you have one?
If you are in excellent health and your family has longevity genes, you can keep working if you want to. On the other hand, if you or your spouse are in poor health, you probably don’t want to put off retiring.
4. How much do you need to cover your healthcare now and in the foreseeable future?
If you are a sixty-five-year-old couple and planning to retire soon, you will need between $200,000 and $400,000 to pay for healthcare—in addition to what Medicare covers. At the very least, you will need savings, private health insurance, or a Medicare supplement policy.
5. Are you planning to live on your Social Security alone?
Retiring with no income other than Social Security may sound next to impossible. Yet, 23 percent of married retirees and 43 percent of single retirees do it. The question is how can you make it work?

• Be aware of what your benefits are likely to be.
• Do a Social Security do-over.
• Eliminate debt.
• Move to a less expensive location.
• Don’t let your tax bill catch you by surprise.
• Buddy up. Think about getting a roommate or sharing your home.
• Be aware of helpful state and federal programs.
• Take advantage of free services.

My son-in-law boils it down to three questions: Have you had enough (of working)? Do you have enough (money to live)? Will you have enough (to do in retirement)?