How Do You Know When You’re Ready to Retire?

There is no magic age, but there are three things you need to be prepared for, and once those stars align, you can be confident that it’s time.

Man sitting under The Milky Way Galaxy with light on his hands.
(Image credit: bjdlzx)

There has long been this image — perpetuated by advertisements, TV shows and movies — of a guy in his mid-60s who just can’t wait to retire.

He’s excited to move to Florida. Or finally travel to Paris. Or to golf … or gamble … or just sit on his couch and read books about the Civil War.

Of course, that guy was never totally representative of his generation — or any generation. There have always been holdouts who couldn’t imagine not working and stayed on the job into their 70s or longer. And there have always been the eager beavers who took a buyout or simply bailed out as early as their late 40s or 50s.

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Even in the days when it was commonplace to grab your pension, your Social Security and your gold watch at 65, and then hit the road, not everyone was set on doing it that way. But it seems to be more commonplace these days, this all-over-the-map mindset and nervousness about reaching certain goals.

Without a pension to count on, workers are less sure of where they stand financially. And though we’re mostly grateful for the health care that’s helping us live longer, we’re not entirely convinced we can afford a retirement that might last three decades. As politicians play with what benefit programs they might pull or privatize, the idea of quitting grows ever more daunting.

Many do quit, don’t get me wrong. Maybe they’re bored, burned out or simply ready to do something else. But the decision seems to be getting more difficult all the time. It’s probably the question I’m asked most often: When will I be ready to retire?

Of course, there is no right answer. It’s different for every person I meet with. So, we talk about all the things that should be considered, including:

Are you ready financially?

If you haven’t already, it’s time to do some accounting work. If you have a pension, how much will your monthly payments be? Will you need to start Social Security right away — and if not, what will the payment be at different ages? How will you generate reliable lifetime income from your retirement savings accounts? And, most important, will these income sources provide enough money to pay all your expenses? If not, you may want to keep working awhile longer. Or, if you’re determined to retire now, you could get a part-time job, but be aware that there are repercussions if you’re taking Social Security and you make too much in one year.

Are you ready physically?

Make sure your retirement plans include activities that will help you stay fit so you can enjoy these years at full bore. Couch potatoes have more health problems and usually don’t live as long as active seniors. If you aren’t healthy, you may wish to ignore all the people who will tell you otherwise and take your Social Security right away, to make the most of it.

A lot of workers delay retirement until they qualify for Medicare (at 65). If you don’t want to wait, you’ll have to look into various health care options. And while you’re at it, think about how you’ll handle any long-term care issues. Health is one of the biggest unknowns in retirement, but there are financial tools that can help you plan for that worst-case scenario. Talk with your financial planner to determine which tool works best for your situation.

Are you ready mentally?

Even the happiest employees complain from time to time, but if you’re still enjoying your job when you’re 65, there’s no need to give it up just because that’s the way you think it should be done. There’s no age when you’re “supposed to” retire.

Think about how retiring will affect you — good and bad — and include your spouse in that conversation. Will there be resentment if one of you retires and the other doesn’t? If you’re both home more, will you get on each other’s nerves? Do you grow bored easily, and if so, will you be able — physically and financially — to travel or pursue new hobbies?

You don’t have to make this decision on your own. Financial advisers who are retirement specialists can assist you. You’ll feel better about the future if you’re content with your decision. So, don’t be afraid to ask for help — then do whatever works for you!

Kim Franke-Folstad contributed to this article.


This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

Gary Mastrodonato, Investment Adviser Representative
Founder, CEO, Masters Wealth Management Group

Gary Mastrodonato is founder and CEO of North Carolina-based Masters Wealth Management Group. In over 40 years of service, Gary has led hundreds of clients through the ever-changing financial markets. His services are specifically aimed at helping retirees and pre-retirees master their financial goals. Gary Mastrodonato is the longtime host of the "Mastering Your Money" radio program.