The Emotional Side of Retirement Planning

Forget finances, you’ll never be ready to retire unless you've thought through exactly what you want your next chapter to be like.

(Image credit: Aldo Murillo)

Historically, people retired when they reached 65, seemed to stay close to home, and typically died within a few years. Today the concept of retirement is very different. It is not unusual for people to work well into their 70s or even 80s at their current job or at a different job. Some work full time and others part time, sprinkling trips and activities like golf games into the routine. I often hear retired clients say they’re busier now than when they worked full time.

What should retirees ask themselves?

The majority of clients who are happily retired spent a great deal of time thinking and planning for it. When clients are in their 60s, I usually ask them if they have given retirement any thought. Most of them have, but are having difficulty formulating a plan. Of course, they all want to know whether they can afford to retire. My typical response is “that depends,” and I follow it with a string of questions such as:

  • Describe what you envision yourself doing the first week of retirement and how does it make you feel?
  • If married, how does your spouse feel about retiring?
  • Do you want to stay in your home or move?
  • Be in warm weather or cold?
  • How’s your current health?
  • Do you want to leave a legacy or spend all of your money?

What does retirement look like?

Before we even discuss whether they can afford to retire, I want to see where they are psychologically and emotionally. If they’re not ready mentally, then all the money in the world won’t buy them a fulfilling retirement.

Subscribe to Kiplinger’s Personal Finance

Be a smarter, better informed investor.

Save up to 74%

Sign up for Kiplinger’s Free E-Newsletters

Profit and prosper with the best of Kiplinger’s expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.

Profit and prosper with the best of Kiplinger’s expert advice - straight to your e-mail.

Sign up

A few years ago, I met with a couple who were long-term clients. We had gotten to know each other quite well. I watched their kids grow up, get married and start to have children of their own. They could afford to do just about anything they wanted. They told me they wanted to move to Arizona and play golf. They wanted a condo on a golf course because the husband was an avid golfer. I asked the wife, who didn’t play golf, what she thought she would do, and she was unclear. My comment was before you make any drastic lifestyle changes, you need a game plan.

The next time I saw them, they had cooled on the idea of moving to Arizona partially because one of their daughters who lived locally was pregnant and they didn’t want to be long-distance grandparents. In addition, they both had good-paying jobs, and they decided they didn’t want to give up the money.

The third time I saw them, they had fallen in love with a condo in Maine approximately an hour and a half from home, near a golf course for the husband, and big enough for the wife to have the kids and grandchildren visit. The wife, a teacher, wants to continue working until she is eligible for her pension and the husband can take time off from work to play golf. At the moment, they plan to stay in their winter home but are thinking of eventually downsizing when the stairs and maintenance become difficult.

What are the stages of retirement?

Today it is not unusual for people to spend 15-20 years in retirement. There are several stages of retirement. Initially people treat it like a long-term vacation. Many go back to school to take fun courses; others decide to get retrained with the idea of changing professions. Most new retirees increase their travel, dine out more and attend the movies, theater or symphony more frequently than they did prior to retirement. They are redefining themselves and their new lifestyle.

After the novelty of retirement wears off, many people tend to settle into a slower, more mundane, lifestyle. They still go out, but are also happy to stay home. Physical issues may start to present themselves. For example, they may not feel comfortable driving at night and switch to meeting friends for lunch instead of dinner.

At some point the majority of people are not able to live independently and need assistance. Some age at home with help, others move to assisted-living facilities, and still others to nursing homes. Each situation is different, and decisions need to be made on a case-by-case basis.

Clearly, the amount of available money influences how, when, and where someone retires. The greater the resources, the more options one might have; however, every potential retiree needs to have a well-thought-out game plan in place that makes sense for them both financially and emotionally.

Securities and Advisory Services offered through Cadaret, Grant & Co., Inc., a Registered Investment Adviser and Member FINRA/SIPC. HMS Financial Group and Cadaret, Grant & Co., Inc. are separate entities.

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.

Barbara Shapiro, CFP®, CDFA®, CeFT
President, HMS Financial Group

Barbara Shapiro is the President of HMS Financial Group located in Dedham, Mass. She is a CFP®, Certified Divorce Financial Analyst and a Financial Transitionist®. She is also co-author of "He Said: She Said: A Practical Guide to Finance and Money During Divorce." Her firm specializes in comprehensive financial planning with a subspecialty in divorce that assists clients' transition from marriage to independence with peace of mind and confidence. Learn more at (opens in new tab).