Take a fresh look at your lifestyle.

When Can I Retire? 21 Questions To Help You Find the Right Time

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Editor’s Note: This story originally appeared on NewRetirement.

When can I retire? It’s a question you probably ask weekly or monthly, if not daily. The reality is that the answer to the question “When can I retire” is highly personal.

And, it is not always all about how much money you have. In fact, money doesn’t always have a whole lot to do with retirement decisions. Lifestyle factors often have more influence.

Here are 21 questions you should ask yourself when trying to figure out when to retire.

1. Do you like work?

Senior worker
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You might be surprised by who is working the longest. Recent research shows that finances aren’t the whole story when it comes to figuring out when to retire.

Guess what: The folks who are more likely to be working longest are those with the highest incomes, greatest wealth, and most education, according to a study from the Center for Retirement Research at Boston College (CRRBC).

So, what gives? Seniority and success at work may offer the kind of rewards that make work fulfilling and enjoyable.

2. When will you start Social Security?

Senior woman weighing whether to file for Social Security
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When you start Social Security is a totally different question than when you stop working. But, you might be able to stop earlier if you wait to start your benefits.

Your total lifetime Social Security payments will likely be greater if you delay the start of benefits until age 70 — whether you are working or not.

3. What are your income needs?

senior couple saving money
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Many people think that they can retire when they have saved enough money. However, most personal finance experts believe you should be asking a different question.

The real retirement question is: How much income do you need in retirement? And, in order to know how much income you need, you must first project your expenses.

How much do you need to spend? How much do you want to spend? And, how will that change over time?

4. How will you fund your income needs?

Senior man using smartphone
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Retirement income planning is another critical part of a secure retirement. According to at least one Nobel Prize winner, you will want to be able to:

  • Guarantee adequate income to cover your mandatory expenses
  • Create flexible income streams for maintaining the lifestyle you would like to live
  • Plan for being able to afford items on your “nice to have” list

Learn more from three steps to a retirement income plan and 18 retirement income strategies.

5. How long will you live?

Shrugging senior confused and worried
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Americans are living longer than ever before. A longer life means that you need to be able to pay for more years in retirement.

According to the latest data, the average 65-year-old man will live another 17 years to age 82. The average 65-year-old woman will live another 19.7 years until 84.7. However, these are only averages, and you stand a very good chance of living longer — much longer even.

What’s important aren’t averages. You need to assess how long you (and your spouse) are likely to live. Try a good longevity calculator to get a more personalized number.

And then, use your personalized projected longevity as part of your retirement planning.

6. What is your projected out-of-money age?

Surprised retiree
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This is a big deal. You obviously want your projected out-of-money age to be after your expected longevity. The NewRetirement Planner makes it easy to identify this number and find ways to improve your situation.

7. Does your investment strategy need to change for retirement?

man helping mom on computer
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You have probably spent much of your working life saving and investing. As you approach retirement, you need to shift from a focus on accumulation (saving, saving, saving) to spending (efficient use and drawdown of your assets).

Retirement is a good time to reassess your investment strategies. Here are 28 retirement investing tips.

8. Are you too dazzled by the allure of retirement?

Senior couple sitting on the couch with laptop and shopping online
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If you spend your days dreaming about what it will be like to kick up your heels during the golden years, you might be more likely to retire sooner than some of your peers, at least by a couple of years, according to a CRRBC study.

The allure of retirement can influence some to leave the workforce early, even if there’s a cost to financial security.

Don’t rush into retirement if you cannot afford it.

9. Have you considered transitioning to retirement?

Older woman at work
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Instead of quitting cold turkey, the ideal might be to transition to retirement — go part time and gradually phase out of work. In AARP’s survey, Staying Ahead of the Curve, older workers indicated essential elements of their ideal job:

  • Adequate paid time off (76%)
  • A flexible schedule (72%)
  • The opportunity to gradually phase into retirement (53%)

Options for transitioning to retirement might include:

  • Retiring from your current job and figuring out how to earn money in a career that would be rewarding to you
  • Taking a job — even a relatively low-paying job — in the field of leisure you most enjoy
  • Working from home part of the time
  • Cutting your hours at work and pursuing your passions now while still earning a paycheck
  • If you could possibly take a year off of work as a retirement trial

You can learn more about retirement jobs here.

10. Are you aware of the many benefits of work?

A black senior man drives a forklift at work
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Did you know that scientists have strong evidence that suggests that work keeps you happy and healthy? There are many benefits of work:

  • Work can give you a place to go every day, which helps keep you feeling young and vibrant.
  • A job gives you social opportunities and mental challenges which keep your brain functioning.
  • Working gives your life a purpose, which actually prevents aging.

11. How is your health?

Senior man with his doctor
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Unsurprisingly, health is one of the top factors that affects retirement decisions.

When you’re planning your retirement, you might have some idea of the age at which you’d like to close up shop for the last time.

However, health can get in the way of those plans. Some may have to retire sooner than originally planned from an abrupt change in health. You’re more likely to retire with poorer health.

Thirty-five percent of people between the ages of 55 and 59 claim poor health for their reason to retire. This is according to a study by the National Institute on Aging.

If you are retiring early due to health issues, you should still use a reliable retirement planner to help you assess your budget.

12. Do you need health insurance from your employer?

Upset senior worried about bills
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Health care is often the most expensive and unpredictable cost to plan for in retirement. In the event of any unexpected health issues, health insurance could protect you from incurring potentially high out-of-pocket costs.

Many retirees rely on Medicare for their health coverage. Those who retire before age 65 may not be eligible to begin receiving benefits.

And, finding affordable health insurance can be difficult for people who lose group coverage provided by an employer.

“Working longer to continue benefiting from employer health coverage is a common reason investors choose to delay retirement,” says Ken Sutherland. He is president of LifePlan Group, a fee-based financial advisory firm in Raleigh, North Carolina.

This strategy is also popular among more than half of American workers. They say they plan to work longer to maintain access to their current employer-sponsored health plans, according to the Employee Benefit Research Institute.

Here are nine ways to cover health care if retiring before Medicare eligibility.

13. Have you seriously evaluated your projected health care costs?

Senior couple upset about money issues
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It may seem that if you have seriously considered health care costs, then you might not ever be able to retire.

The expected out-of-pocket health care spending for an average couple in retirement is estimated to far exceed the average savings of those households reports the Center for Retirement Research.

According to Fidelity Investments, a 65-year-old couple retiring in 2023 can expect to spend $315,000 in out-of-pocket health care and medical expenses throughout retirement. And, this estimate does not even include the possibility of needing to fund long-term care.

14. What’s your plan for a long-term care need?

Worried retirees reviewing finances
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About 70% of people who turn age 65 will need some type of long-term care in their lifetime, according to the U.S. Department of Health and Human Services, but few are prepared to pay for that care.

The costs of long-term care are exorbitant — ranging, on average, from $51,000–$102,000 a year according to this survey — and are not covered by Medicare.

However, long-term care insurance is also extremely costly.

So, what is your plan for these costs? Explore 10 alternatives to long-term care insurance.

15. How are you planning for other unknowns?

Mother and daughter discuss estate plans
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Inflation, stock market crashes, natural disasters, car accidents, and more. There are so many potential risks that could impact your financial well-being.

It is important to have a best-case and worst-case retirement plan.

16. When to retire? Have you calculated potential family needs?

Happy people of many generations
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Many around retirement age are members of the sandwich generation — you have dependent children as well as elderly parents. And they all may desire emotional and financial care.

If you are a member of the sandwich generation, then you need to calculate the future costs of supporting your children and your parents.

Costs can include college and weddings for your children and health care for your parents.

17. Have you met with a financial adviser?

Worried senior reviewing bills
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The best person to ask, “When can I retire?” is probably a professional. You only get one chance to completely retire, and it is not something you can afford to get wrong.

Meeting with a financial adviser about when you can comfortably retire can give you peace of mind.

Choosing a retirement date is like solving a very complicated puzzle. There are lots of unknowns, trade-offs, and complex financial math. Many people do it on their own, but the right financial adviser can give you the reassurances you need.

18. Have you explored trade-offs?

Senior man working on a laptop
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Any retirement date is possible — especially with trade-offs.

There are so many different ways to retire. For some retirement means having millions in savings. Others can cut costs dramatically and live on Social Security alone. There is no one right way.

Hundreds of different levers can be adjusted to help you discover a plan to retire at an age that suits you — part-time work, downsizing, delaying the start of Social Security, relying on passive income, etc.

19. How will your housing needs change over time?

Senior couple happy at home
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From finally getting to spend time in your vacation home to downsizing, retirement abroad, or moving to a continuing care residence, it is not unusual to spend your retirement outside of your long-time residence.

Explore eight ways to cut housing costs for retirement.

20. Do you know what you want to do next?

Retiree outside his house in sunny weather
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When you ask yourself, “When I retire,” are you trying to get away from something or to something?

A study from Merrill Lynch found that 9 out of 10 boomers see retirement as an opportunity for a new beginning — not an end of something. Retiring to something can be critical to your retirement happiness.

It is even better if what you choose to do in retirement is meaningful. Research from Oxford University finds that a meaningful life lessens the effects of aging.

In fact, people with a sense of purpose had a 15% lower risk of death, compared with those who said they were more or less aimless.

And it didn’t seem to matter when people found their direction. It could be in their 20s, 50s, or 70s — even when controlled for other factors that affect longevity like age, gender, and emotional well-being.

The study found that a sense of purpose led to a longer life. Explore six ways to find meaning. Need some inspiration? Here are 120 ideas for what to do in retirement.

21. Have you fostered the life skills you’ll need?

Older woman smiling and looking out a window
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You are probably thinking, “What in the world? Life skills? I am a grown person on the brink of retirement. I’ve made it this far.”

Yes, you have made it to retirement, but this new phase of life is enhanced with the right life skills like a knack for dealing with uncertainty, resilience, being a good friend, self-motivation, a purpose and more.

Explore the eight unexpected skills you need for a happy future.

The Ideal Retirement Age Is Whenever You Have Financial Freedom and a Good Idea of What You Really Want To Do With Your Time

Happy Senior Man At Home
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We are all asking ourselves, “Should I retire?” “When can I retire?” “Can I retire now?” … “What about now?” While the answers to these questions are highly personal, you are probably ready if:

  • You have a strong financial plan.
  • You know how you want to spend your time.

If you are not sure about these factors, then perhaps you’ll benefit from delaying retirement. A delayed retirement can indeed make you happier, healthier and certainly wealthier.

Delaying retirement provides you with extra time to work longer and build a greater nest egg. It also allows you to claim higher Social Security benefits, which can boost your quality of life.

It may surprise you to learn that delaying retirement can enhance your happiness and health. Let’s not forget lifetime wealth.

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