Deciding when to retire isn’t easy, especially when you’re in a career you love.

Even if you’re very happy in your work, there likely will come a time when you decide that retirement makes sense. It may be an issue of health or you may take stock of your life and realize there are things you would rather do with your time than come to work each day.

Some people retire because they’re ready to experience life without the daily structure that having a job demands, said Joan Marie Gagnon, a retired accountant and the author of the book “Journal Your Way to Retirement.” They look forward to the spontaneity of being able to make a new plan each day. They also want to explore hobbies and special interests they may not have had time for when they were pursuing a career. When the desire to do new things becomes more important than the desire to continue working, it may be time to make a change.

In contrast, some people retire only because they must, she said. They may have lost their jobs due to layoffs and corporate downsizing, or they may have health problems that make continuing their careers difficult.

William Stack, a financial advisor in Salem, Mo., said some of his clients don’t like to think about retirement. They simply plan to keep working as long as possible. Their decision to stop working often comes when they realize that they are running out of time to do other things they enjoy, such as spending time with family and friends, pursuing hobbies, and traveling.

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Recognizing When You’re Ready to Let Go of Your Job

Many people have no trouble deciding when to retire. Often a job that once excited them no longer holds the same appeal.

You’re ready to retire “when you wake up thinking about things other than going to work, when you find that it’s just not doing it for you anymore and there are so many other things you want to do,” Stack says. “You feel that time is slipping away.”

Howard Rosen, a 65-year-old retired tax accountant who lives in Scottsdale, Ariz., left his job last year. He said he knew it was time to retire when he couldn’t face another busy tax season.

“I just got to the point where I didn’t want to do it anymore,” he says.

Gagnon decided to retire in 2016, after her sister’s husband died and her sister was diagnosed with Alzheimer’s. The stress of dealing with multiple family members’ health issues had left her feeling emotionally drained.

“One morning I woke up and said ‘I have to retire,'” she recalls. “I was under so much stress.”.

Some people never find the perfect time to retire, says Patrice Jenkins, an organizational psychologist in Saratoga Springs, New York. They’re torn between the desire to stop working and the need to continue earning a salary. Sometimes a decision comes down to considering all the pros and cons and making the best choice.

“It’s like any major life transition,” she says. “You do as much research as you can and you take a leap.”

Developing a Financial Plan

Your plan for life after retirement should fit your financial situation, says Gagnon. Plans for a retirement filled with travel will prove disappointing if you don’t have enough money to make it happen.

“You may have ideas about what you want to do, but if the money doesn’t work, it’s a problem,” she says. “There are things you can do to make the numbers work. You may have to cut back on your expenses and you may have to move to someplace less expensive. You need to be realistic.”

Rosen says his goal in retirement is to have enough money to support his wife and himself throughout their lifetimes. He moved from St. Louis to Scottsdale because it’s less expensive and his retirement income will go farther.

Mike Kojonen, a financial advisor with offices in Woodbury, Minnesota, and Hudson, Wisconsin, says having enough money to carry you through retirement is an essential part of deciding when it’s time to leave your job.

“I recommend having 10 times your annual salary saved,” he said. “Just like the spending budget you’ve hopefully been relying on throughout your working years, a retirement budget takes into account income versus spending. Even though you won’t be getting a paycheck, you’ll have income in the form of investment earnings, Social Security and possibly a pension.”

To figure out your monthly expenses, use an average year’s expenses and divide it by 12, he said. “It may sound like a lot of work, but you are not ready to retire until you’ve taken that step.”

Beverley Kimball, 64, a retired physician’s assistant who lives in Webb Lake, Wisconsin says she decided to retire at the end of 2016 when she realized that she and her husband had saved and invested enough money to maintain their lifestyle without working. They want to continue living independently in their rural community.

“We have substantial medical expenses,” she said. “We didn’t want to become a burden on our children.”

When people can’t make ends meet in retirement, Stack suggests that they consider working part-time. Once they get over the disappointment of not being able to stop working entirely, most people adjust well to having a part-time job.

Stack says the decision to work part-time usually comes out of economic necessity. People who decide to do so typically want to maintain their pre-retirement lifestyles, but they don’t have enough income from pensions, investments or Social Security benefits to do so without a part-time job.

“You don’t need to feel like a failure because you’re working part-time,” he says. “It’s just a part of life. There are difficult decisions to be made.”

Gagnon counsels people to closely examine how much money they spend each month to determine if there are ways to cut back before they retire. If your income is going to decline in retirement, you need to reduce your spending accordingly.

She had one client whose lavish pre-retirement lifestyle included a spending $6,000 a year on wine. She convinced him that retirement on a smaller income would require some belt tightening.

Kojonen advises retirees to set aside the equivalent of six months of income in an emergency fund upon their retirement date, for unforeseen expenses.

“It’s that peace of mind money you need to have, so you don’t have to rely on your investments” in case of emergency, he says.

Announcing Your Retirement

Deciding when to tell your company and co-workers that you’re going to retire depends on your work situation.

If you are in a key role at work and your job is complex, you may feel compelled to give your supervisor plenty of notice so he or she can identify and train someone else to fill your job. Once you’ve set a date for your departure, your employer may be reluctant to give you assignments that will require follow-up work after you’ve left the company.

Stack cautions his clients to keep their retirement plans to themselves until they get close to their departure date. In some cases, supervisors worry that people who are close to retirement will develop “short-time syndrome” and no longer do their best work, Stack says.

It’s traditional to give employers at least two weeks notice before you leave a job, Stack said. Not doing so could cause hard feelings and make your former employer less likely to recommend you if you decide to work for another company after you retire.

It’s important to make sure you’re truly ready to leave your job before you begin discussing your retirement with your employer. After you’ve made an announcement, it may be difficult to change your plans. For example, once your employer has hired someone to replace you, changing your retirement plans could cause your company a major inconvenience and upset the plans of your replacement.

Stack says about 20 to 30 percent of the retirees he advises change their mind and wish they had not retired within a year and a half of their departure from the workplace.

Typically such people are in their early 60s and in good health, he added. “They get bored. Work was more than money for them. They had their friends there. If they had to do it over they would have worked for a few more years.”

If you’re planning to work in retirement, you may want to personally notify your colleagues and business associates that you’re leaving your present job. You can do this in person or with a personalized email that is sent after you tell your employer you are leaving. It will provide an opportunity to tell people about your future plans. If you’re going to start a business or you’re willing to consider offers of work, this is a way to let people know.

If you need to reach a wide range of business and personal contacts with your retirement news, you may want to consider using social media platforms, such as Facebook.

Some people decide to continue working in a less structured environment after they retire. Depending on their profession, they may find work as consultants or independent contractors. This may enable them to set their own hours and work only as often as they would like to. If you retire on good terms with your employer, he or she may send business your way or become a valuable reference who helps you find work from other companies.

Working in retirement is a tradeoff. You may bring in extra money and get to work on your own terms but you also are giving up leisure time and time with the people you care about. Before you decide to continue working you may want to consider the following questions:

  • Do you need the money? If not, it may be more important to you to stop working and enjoy the retirement you’ve earned, Stack said.
  • How much time will it take? If you don’t have the time to pursue personal interests in retirement, it may not be worth it to you.
  • Is it what you really want to do? Just because you can work in retirement doesn’t mean it’s the right thing to do. You should consider whether it will make your life better, Stack said.
  • What does your spouse or partner think? If your husband or wife was looking forward to spending more time with you, will they be happy with your post-retirement job?

Approaching Your Spouse About Retirement

Before you leave your job it’s important to confer with your spouse to make sure your retirement plans are in sync. Not all couples retire at the same time. When one spouse retires, his or her partner may decide to keep working for the extra income or because they enjoy their job and aren’t ready to quit.

If you have a spouse who isn’t ready to stop working, you may decide to postpone your plans to leave your job so you can retire together. In cases where one partner is a stay-at-home spouse, he or she may have a hard time adjusting when their partner retires, said Gagnon. That person may feel constrained when they suddenly have a wife or husband making suggestions about how to run the household.

“If the retired husband or wife is going to be around all day, it can cause problems,” Gagnon said.

Kojonen agrees that retirement can put a strain on a marriage. Couples who spent much of their time working must adjust to being together more often.

“When a couple retires together, they suddenly have a lot of time at home together, which can be a difficult adjustment,” he said.

It helps if people involve their spouses in their decisions to retire, said Jenkins.

“This is a conversation that needs to happen long before the date is set,” she said. “When both people retire at the same time, that is the best case scenario because they can figure out this transition together.”

Not every relationship can withstand constant togetherness. If people have marital problems, she advises them to attempt to resolve them before retirement.

“Retirement magnifies the condition of a relationship,” Jenkins said. “If the relationship is healthy, it tends to get better. If not, it tends to deteriorate.”

According to Rosen, the secret to contentment in retirement is staying busy. He and his wife fill their time with travel and taking classes.

“You need another passion,” he said. “When you retire your life doesn’t stop, it just changes. You need to stay active.”

Creating Your Bucket List

Jenkins says it’s a good idea to set goals for what you want to accomplish in retirement. She advises people to take stock of what they want to do most, since many people have a limited amount of time and money to realize their goals.

Not everyone creates a “bucket list” that includes visiting exotic places in retirement, she added. There are other fulfilling ways to spend your time. Perhaps you’ve always wanted to hike a certain trail or learn a skill, such as speaking a foreign language — that’s bucket list material too.

When you make your list, consider your hobbies. If you enjoy collecting coins, working with wood or playing an instrument, retirement can give you time to develop your interests. Money also is a consideration. You’ll be disappointed if your bucket list is full of activities you can’t afford to pursue.

You may like to travel, but don’t forget about the bucket-list activities that are available locally. Perhaps you’d like to volunteer at a local museum or get involved with community theater.

Retirement also can provide opportunities to build stronger bonds with friends and family members. The pressures of life while working lead some people to neglect their personal relationships.

“We don’t plan extensive traveling,” said Kimball. “We plan to continue our lives the way they are. Top on the list is being able to spend time with our grandchildren.”

Rosen and his wife have created two lists of retirement goals. One is traveling to countries they have never seen. The other involves finding ways to give something back to their community.

Stack said some retirees find it fulfilling to donate their free time to charities and nonprofit organizations. Many organizations recognize that retirees have gained knowledge and wisdom that can be useful in volunteer work, he added.

“They still have a lot to contribute to society,” Stack said. “There is a younger generation that needs their input and wisdom.”