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Do Plans We Make for Retirement Match Reality?

We asked 15 retirees what their life is really like

By Carol LaChapelle

It was my friend Jane who launched me on this quest.

At 67, she was set to retire after nearly 40 years as a medical editor. And unlike many others nearing retirement, she wasn’t looking forward to it.

As we talked, Jane said she just couldn’t “see” herself retired, which got me thinking: Who does? And what do they see?

As a writer who lives in her imagination 24/7, I wanted to know how others lived in theirs, especially as they anticipated retirement. I also wanted to know if there was any correlation between what they imagined and what became real.

(MORE: 10 Secrets to a Successful Retirement)

A Questionnaire to 15 Retirees

I sought answers from friends, colleagues and writing clients, sending a brief questionnaire to more than 15 men and women — two very newly retired, one going on 13 years, most living in my home state of Illinois, others in Arizona, Texas, Utah, New York and Florida.

Most are married with grown kids and grandchildren; the rest are never married, remarried or widowed.

Except for two people, all had retired in their 50s and 60s from long careers in education, banking, journalism, not-for-profit administration and as government employees. As such, all were in a financial position to retire — or near enough.

Besides, the money part is not what interested me. It was a given; I wanted to know about retirement as a process of discovery: Who am I becoming at this stage in my life?

My First Question

So the first question I asked was: What did you think you’d do once you retired? Here's what some of them said:

Patsy, widowed, retired 13 years: “I thought I would retire to Utah with my husband. However, he passed away five years after I retired, shortly before we were scheduled to move. I did move alone to Utah and have been here for eight years.”

Judy, single, retired nine years: I had no specific plans on what I'd be doing. Mostly, I just looked forward to being in charge of my own schedule. I assumed I would travel and volunteer some. This has happened. I also assumed I'd spend more time with family and friends. That, too, has happened.” (See below for what Judy emailed me just hours later.)

Ron, married with kids, retired almost two years: “Whatever — I wasn't worried about filling my time, knowing I’d be spending it with my spouse, kids and friends. After all, my job wasn't my life.”

My Second Question

But it was really the second question, a two-parter, that interested me most: Has what you imagined about retirement materialized? What have been the biggest surprises?

Mike, married with kids, retired six years: “I planned to spend more time with my wife and our family. But as retirement got closer, I decided to fulfill a long-time dream: to ride my bicycle, alone, from Chicago to San Francisco and down to LA. I left on the two-month trip the day after I retired.”

Jack, married with kids, retired nine years: “Looking at a map of the U.S., my wife Jean and I pointed to Florida as the one place we would never, ever want to live. Then, seven years later we moved there, where we still live part of each year.”

Ruth, married, no kids, nine years retired: “A negative surprise was realizing that my regular office work schedule had provided structure to my life. Without it, I get much less done in a day.”

Diana, married, no kids, 11 years retired: “One of the biggest negative surprises was realizing how much of my socializing and friendships were tied to my workplace. And as I retired early (at 58), I was a decade younger than other retirees — out of synch, I felt, in both energy levels and attitudes.”


Jerry, married with kids, one year retired: “If you are a man, when you retire and you no longer go off to work every day, you will find that you have entered the realm where your wife runs things — the home and family. So you will be recruited to do a lot of things your wife has dreamed up and you won't be at work, so you will not have a really good reason to say no.”

(MORE: Why Professional Men Over 60 Keep Working)

Helen, single, nine years retired: “On that first new day of retirement, time just opened up — like a flower, like a space fresh and new and open. I had not that expected at all, that I could saunter through a room and not feel guilty for picking up a magazine instead of a paper to grade.”

And returning to Judy: “For two years after I retired, I continued to work part-time at the place I retired from. These opportunities came as a total surprise. It was certainly nothing I ever anticipated. The initial opportunity was to serve in a consulting capacity, and I worked from home on several special projects. This gave me great flexibility and at the same time helped ease the transition from full-time work to full-time retirement.”

6 Things I Learned From The Retirees

Now, in attempting to extract the collective wisdom in these retirement stories — and to help Jane find herself somewhere in them — I came up with the following:

1. As with most of life, you can expect surprises, some good — “I found the time to live out a long-held dream” — and some not so good — “I’ve lost the person I’d hoped to spend my retirement with.”

2. You can get lucky. Sometimes, what you hoped retirement would be, it turns out to be.

3. Family relationships — especially with spouses, often with kids and grandkids — may have to be re-negotiated.

4. You will have a lot of time to fill and may not always know exactly how to fill it. And that’s fine.

5. The obvious — make new friends, learn new things, volunteer and stay physically fit.

6. And maybe most important: You are not finished growing as a person. There’s more to discover about yourself.

And so I close with Mimi, newly widowed, retired less than a year ago: “To those who are contemplating retirement, I’d both caution and encourage. I’d caution them to expect that, like every developmental stage in our lives, it involves work, worry, pain, puzzlement, fear and risk. It also brings insight, growth, fun, adventure, discovery, joy and love. If you don't expect both, you’ll be blindsided by one. Blessedly, there are plenty of us around to help.”


Carol LaChapelle is a Chicago-based writer who conducts online writing workshops and blogs about the "Boomer and Beyond life". She is the author of Finding Your Voice, Telling Your Stories and is at work on a second book. Read More
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