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.


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.
From just $107.88 $24.99 for Kiplinger Personal Finance
Be a smarter, better informed investor.

Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
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.
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

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 HMS-Financial.com.
-
Kickstart Your 2026 Retirement Plan Now
Retirement can feel far-off, or too close for comfort, depending on where you’re at. But one thing’s clear — now is the ideal time to get your retirement plan in order.
-
Four Clever and Tax-Efficient Ways to Ditch Concentrated Stock Holdings, From a Financial Planner
Holding too much of one company's stock can put your financial future at risk. Here are four ways you can strategically unwind such positions without triggering a massive tax bill.
-
Four Clever and Tax-Efficient Ways to Ditch Concentrated Stock Holdings, From a Financial Planner
Holding too much of one company's stock can put your financial future at risk. Here are four ways you can strategically unwind such positions without triggering a massive tax bill.
-
Beyond Banking: How Credit Unions Serve Their Communities
Credit unions differentiate themselves from traditional banks by operating as member-owned financial cooperatives focused on community support and service rather than shareholder profit.
-
Answers to Every Early Retiree's Questions This Year, From a Wealth Adviser
From how to retire in a crazy market to how much to withdraw and how to spend without feeling guilty, a financial pro shares the advice he's given this year.
-
The Risks of Forced DST-to-UPREIT Conversions, From a Real Estate Expert
Some new Delaware statutory trust offerings are forcing investors into 721 UPREIT conversions at the end of the hold period, raising concerns about loss of control, limited liquidity, opaque valuations and unexpected tax liabilities.
-
I'm a Financial Adviser: You've Built Your Wealth, Now Make Sure Your Family Keeps It
The Great Wealth Transfer is well underway, yet too many families aren't ready. Here's how to bridge the generation gap that could threaten your legacy.
-
Want to Advance on the Job? Showing Some Courtesy and Appreciation Could Help
Two business professors share their insights about the impact of digital communication on the social skills of some in Gen Z and the importance of good manners on the job.
-
From Job Loss to Free Agent: A Financial Professional's Transition Playbook (and Pep Talk)
The American workforce is in transition, and if you're among those affected, take heart. You have the skills, experience and smarts that companies need.
-
A Financial Planner's Top Five Items to Prioritize When Your Spouse Is Ill
During tough times, it's easy to overlook important financial details, but you'll be so much better off if you take care of these things right now.