Filling my days isn’t my concern. Milking them is.

By Joel Dresang

Mere weeks from retirement, I’m in an extraordinary position to know what to expect. I’ve been working 16 years with professionals who help people build toward and thrive in retirement. Much of my job has been helping those professionals educate their clients.

But retirement is like childbirth. Everybody tells you it’ll change your life, but you don’t really get it until you go through it yourself.

Based on what I think I know and the discussions my wife and I have had with our advisor, I’m more confident about what’s going to happen financially. It’s the existential non-financial parts where I have questions. Like, how can I make the most of what’s left of life? (Or at least, minimize messing it up?)

Welcome insights

No two experiences are the same. But collectively, I figure, the impressions of other retirees can help me transition.

I’ve been noting friends who recently retired. One is publishing a book of poetry; another is setting reading goals; some are taking classes; others are posting snapshots of their travels on social media. Some are getting more involved in civic and charitable groups; some are devoting more time to parents or grandchildren.

I’ve sampled surveys, too. On a podcast called yes2next, I watched a former colleague of mine interview a retirement author who has gathered experiences from other retirees. I also found a retired retirement researcher who drew together academic literature and reflections from former colleagues.

Retiree remorse

Riley Moynes, the podcast guest, says retirees typically treat the first years after work as vacation. Or maybe more like a college kegger because he found that after a couple of years living it up, many retirees wake up feeling lost and confused. They miss the routines of work, the socialization, the sense of purpose.

Moynes suggests that the most satisfied retirees are those who can connect their past achievements to new pursuits that tap into their passions and talents. Once retirees figure that out, he says, retirement becomes joyful and fulfilling.

I’ve already begun to connect the dots. I’ve been taking acting classes and getting involved in theater, something I enjoyed in high school. To feel more involved in the community, I’ve volunteered and served on boards. My association with one nonprofit landed me as a co-host on a radio program, which I find particularly gratifying.

Of course, the advice to stay busy, be social and do good doesn’t surprise me. Steve Giles covered all that at the 2025 Investment Outlook Seminar. Steve also spoke about taking care of oneself. To that end, I’ve joined a gym to fit more fitness into my retirement regimen.

Slowing down, shortening outlook

What threw me for a loop, though, is an observation by Terry Mitchell, an emeritus professor at the University of Washington. Mitchell has researched why people leave work and since retiring in 2024 has focused more on folks in retirement.

In one study, Mitchell discovered that retirees have “the absence of almost all long-term goals.” He writes (his emphasis):

“In retirement you will find that many of your goals are in the moment. Pay attention to what is happening to you now. Take pleasure in events and happenings that are self-encapsulated: time talking to a friend, listening to music, reading a book, walking with a grandchild on a sunny day. Much of your happiness will come from such experiences.”

That’s a phase of my retirement planning that I’ve overlooked: Ramping down.

But it makes sense. After decades of having goals set by employers or prescribed by career ladders, retirees can set their own course. And instead of scanning the horizon, they focus on what’s near.

Working on not working

I’m not good at downshifting — so people have told me throughout my working life. “Save some work for tomorrow,” my wife has said more than once when I’ve been working from home and she returns from her workday to find me at the computer, right where she left me in the morning.

Working from home has suited me because I’ve never been much of an office socializer. Whether it’s awkwardness or work ethic or impostor syndrome guilting me into staying busy, I’ve tended to opt out of coffee breaks with colleagues or joining them for lunch. (My loss, I know.)

Even at home, I set a timer to remind me to step away from my desk, then hit snooze when the alarm chimes.

Learning to tap the breaks

Having realized that I suck at slacking, I’ve been trying to be more conscientious about calling time outs.

I’ve played at retirement on weekends and other days off, trying to imagine what it’d be like to face every day without deadlines and tasks and accountability. (Or at least none related to work.)

But weekends are too short, and the occasional vacation has been purposely organized with travel, events, family obligations and so on. In the end, I still had work to catch up on, projects to finish, email to answer.

Lately, I’ve been trying to practice the art of idling. For instance:

• I’m reading more. (I keep count.)
• I’m arranging to meet some friend for coffee now and then. (Less often for beer.)
• I’m attending more theater. (Partly because I’ve started ushering.)
• I finally got a Milwaukee Film membership. (Although I haven’t used it yet.)

Trying to both back off and push myself 

In challenging myself to slow down, I’m realizing that now’s the time to try new things or to retry old ones. Moynes identifies a trial-and-error phase in which successful retirees pursue a balance of making impact and taking enjoyment. That appeals to me because when I reflect back on the risks I’ve taken in my life, I wish I would have taken more.

I expect my retirement to be a work in progress. Better yet, an “infinitely perfectible art.” That’s how my favorite theater instructor described acting.

I want to make the most of retirement knowing that it won’t be perfect. That gives me permission — it requires me — to keep taking risks (trying and sometimes failing) to discover ways to fulfill myself and maybe make a difference to others.

Joel Dresang is vice president-communications at Landaas & Company, LLC.