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A 5-Year Diary Can Help You Chart a Successful Retirement

These tools of reflection can keep you on track during this major life transition

By Bart Astor

When my friend Marty Guthrie learned that another friend, Mike McPherson, was starting a five-year diary, Guthrie told him that she was now on her second one.

These daily journals, with five spaces for each date to jot down a few lines about the day’s activities, make it easy to look back at each of the previous year’s entries, and Guthrie had found it useful tool for reflection and figuring out her next steps.

McPherson was planning to use his to get through retirement after announcing that he'd be stepping down from his position as president of the Spencer Foundation in Chicago. The diary would give him a chance to see, in a year’s time or maybe two or three, whether he was actually retiring successfully.

“Next year on this date,” he said, “I’ll look back at what I wrote this year. And if I see essentially the same kind of entry, I’ll realize I haven’t really retired.”

A Mindful Retirement

For those in the 50-plus demographic, maintaining a daily journal to track your progress can be especially enlightening — and quite a different pursuit from the diaries we kept in our youth.

“When I first started my five-year diary, I was in the beginning stages of thinking about what my life would be like after I stopped working and after the kids were grown,” Guthrie said. “But unlike Mike,” she said, “I was still planning to work for at least another five or six years, maybe more.”

For Guthrie, the diary was a personal growth opportunity. An avid photographer, she had chronicled her life and her family’s lives through thousands of pictures, which she posts on Instagram. Similarly, "the diary is a placeholder for memories," Guthrie says. “It’s always fun to reminisce. Sometimes when I write an entry and look at what I’ve written three or four years ago, I smile and I can remember almost exactly the mood I was in when I wrote that note."

But the diary has also served a different function than her photographs. “Writing it down, noting what I did, and maybe adding a brief note about what was in my head, was altogether different than taking a picture," she says. "It was almost like the diary was using one part of my brain while my photography used the other side.”

Guthrie says she’s learned a lot about herself through the five-year diary because it tracks her own growth and charts her progress, providing insight into whether she's moving toward her goals.


Keeping a diary may even help you establish new priorities.

Setting a Course for Success

McPherson confesses he doesn’t know what his life will be like a year from now when he’s not the president of something, has no meeting to go to and no reason to wake up at a particular time. That's where the diary comes in. “I expect that I’ll see some kind of progression where I’m heading in a direction — even if I don’t realize it at the time I’m writing the entry," he says. "And my guess is that when I’m trying to figure out new goals, looking at the path I’ve taken over the last year or two will help guide me.”

For her part, Guthrie cherishes the moment just before she writes her daily entry, when she takes a few seconds to glance at what she put down in the preceding years.

She and McPherson have two pieces of advice for others started their own five-year diaries:

One, it doesn’t hurt if you skip a day.

And two, aim to write one "good thing" about each day — to focus on the positives in your world when things in the bigger world don't make sense.

Photograph of Bart Astor
Bart Astor, an expert in life transitions and elder care, is the author of the book AARP Roadmap for the Rest of Your Life: Smart Choices About Money, Health, Work, Lifestyle and Pursuing Your Dreams and Baby Boomer’s Guide to Caring for Aging Parents. His website is and he can be reached at [email protected]. Read More
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