4 questions to ask yourself before retiring

The retirement checklist
The retirement checklist

The transition from career life to retirement can be awfully bumpy. Before you decide to proceed with such a major life change, it's a good idea to ask yourself certain questions to confirm that you're ready to leave the working world.

Will I have enough income to support myself?

You may be psychologically ready for retirement, but if you're not financially ready, you'll have a pretty miserable retired life. Before taking the final leap, review your retirement savings accounts, your Social Security statement, and any other sources of retirement income you have lined up. Add up your annual sources of income to see how much you'll have coming in each year (for retirement savings accounts, assume you'll be taking 3% to 3 1/2% per year), then compare the resulting total to your current income. If your projected retirement income is significantly lower, ask yourself if you can really get by on that much money without being miserable. If you're not sure whether your projected income is sufficient, use a retirement calculator to add up your likely expenses and compare that number to your projected retirement income.

What will I do with my time?

The more involved you are with your career, the more jarring it will be when you retire and leave that career behind. It's important to come up with something before you retire that will take the place of your career in retirement. Don't assume you'll be fine just hanging around the house catching up on your reading. You might enjoy such a relaxed lifestyle for a few weeks, but many people find that boredom quickly sets in. One way to ease the transition to retired life (assuming your employer agrees) is to switch to a part-time schedule for a while, either right before or during the first part of your retirement. Another option is to look for other activities to fill the void: hobbies, classes, volunteer work, travel, family activities, and so on.

Where will I live?

Your current living situation may or may not work for you in retirement; it's certainly something that you should consider in advance. For example, if you own a big house it may be more home than you really need, and the time and energy that you currently spend on cleaning and upkeep may be more of a commitment than you want to make as you get older. Selling a too-big house and moving into smaller living quarters is also one way to supplement your retirement income. Even if you are currently in good health, you might want to think about moving into an assisted living community. Some of these communities allow you to start out in independent housing and then move you into a higher-care part of the campus if your health deteriorates later. If you do eventually require long-term care, being able to get that care in a familiar living environment can be very reassuring.

Do I understand how my financial life will change in retirement?

Switching over to retired life is pretty jarring for your finances, too. And it's not just a matter of changing over your sources of income and the kinds of expenses you'll incur (although that's certainly a factor too). For example, once you retire you'll no longer have an employer withholding income taxes for you. You'll have to calculate and pay your own income taxes. Most retirees are required to make quarterly estimated tax payments to the IRS and sometimes to their states as well. You'll also be responsible for calculating and taking required minimum distributions (RMDs) from your tax-deferred retirement accounts according to the IRS's schedule. And if you have multiple types of accounts -- for example, a tax-deferred IRA, a Roth IRA, and a standard brokerage account -- you'll have to decide how much to take from each account every year to provide the income you need. If you are unsure on any of these points, consider scheduling an appointment with a financial adviser with experience in retiree income.

Other factors

Entering retirement also comes with some significant one-time decisions that may be irrevocable. For example, you'll have to decide whether to claim Social Security benefits early, at full retirement age, or late. This decision will affect your entire retirement, because the date at which you choose to claim Social Security benefits will determine how much you get in your benefits checks as long as you live. You'll also have to decide whether to choose original Medicare (possibly with a Medigap plan) or to go with Medicare Advantage.

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Start researching and thinking about these decisions well in advance, so that you are totally prepared when the time comes to make them. The more you know about the possibilities, the wiser your final decision is likely to be.

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