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.
-
These Stocks Dipped in 2025. Do They Have Value?
If you are looking to add new long-term positions to your portfolio, as you should, this is the time to examine stocks that the market shuns.
-
Striking Gold (or Gas): A Financial Pro Unpacks the Nuances of Energy Investing
Investing in the energy industry, particularly oil and gas, involves understanding the facts about how projects generate returns through cash flow and long-term asset building, while also being aware of the risks.
-
Striking Gold (or Gas): A Financial Pro Unpacks the Nuances of Energy Investing
Investing in the energy industry, particularly oil and gas, involves understanding the facts about how projects generate returns through cash flow and long-term asset building, while also being aware of the risks.
-
Escaping the New Golden Handcuffs: A Financial Expert Has a Plan for Today's Executives
Feeling stuck in your job? It could be your complicated compensation package, but it also could be where you live, your family or even how you view yourself.
-
I'm a Financial Planner: Here's How to Invest Like the Wealthy, Even if You Don't Have Millions
Private market investments, once exclusive to the ultra-wealthy and institutions, have become more accessible to individual investors, thanks to regulatory changes and new investment structures.
-
Four Ways a Massive Emergency Fund Can Hurt You More Than It Helps
Saving too much could mean you're missing opportunities to put your money to work. Redirect some of that money toward paying off debt, building retirement funds, fulfilling a dream or investing in higher-growth options.
-
I'm a Financial Planner: How to Dodge a Retirement Danger You May Not Have Heard About
Timing is everything, and sequence of returns risk can mean the difference between a retirement nest egg that's overflowing … or empty.
-
Caring for Aging Parents: An Expert Guide to Easing the Financial and Emotional Strain
Early conversations, financial planning and understanding the progression of care needs can help to mitigate stress and protect family relationships.
-
I'm a Financial Adviser: The OBBB Is a Reminder for Older People to Have a Long-Term Plan
The new tax bill presents a good opportunity for retirees to revisit tax plans, look into doing some Roth conversions and consider plans for long-term care.
-
I'm an Insurance Expert: This Is Exactly Why Your Insurance Rates Are Soaring (and What You Can Do)
A dramatic rise in the frequency and cost of severe weather and wildfires means you need to prepare, prepare, prepare — no matter where you live — for higher premiums.