How Do You Feel When You Contemplate Retirement?

Some people plan their retirement meticulously, some fall into it and others don’t consider it at all until someone carts them away. No matter how it happens, after an adulthood of working, most of us face the prospect of retirement at some point. Facing that prospect is jubilant for some and anxiety-provoking for others. There are serious financial considerations for a lot of us, to be sure, but that’s not all and that’s not the focus of this post. Mental and emotional considerations can play a huge role when you contemplate retirement. After all, you want your healthspan to match your lifespan and an unsettled retirement can torpedo both.

Is Retirement Good For Your Health?

Studies are mixed as to whether exiting the working world is good or bad for your health. Both or either can be true. Factors that affect the effect include the nature of the job from which you’re retiring, your own health and responsibilities, and your socioeconomic status, with, as expected, better-off retirees seeing improvements in their health, and worse-off retirees at greater risk for declines. It seems unfair but retirement can increase the risk for heart disease and other physical and mental health conditions, including depression, by 40%. Experts point to lack of purpose and social connection as the culprits. I’d add potential lack of structure or routine into the mix. Some of the same considerations likely apply to those who work unpaid inside the home when the nest empties. Busyness can get you down and add value at the same time.

Retirement Fantasies

It’s not unusual to fantasize about retirement while you’re still working and then feel unmoored when the time comes. Who doesn’t dream about sitting on an Adirondack chair, gazing out at a lake, sipping from a cold glass of something, going for long, unpressured walks, living and eating off the land, basking in the comfort of the great outdoors, with no alarm clocks or to-do lists in sight? Is it just me? Really?! Maybe your fantasies took you in different directions. Maybe all you fantasized about was the freedom to sleep whenever you want. Even if fantasies of a non-working life were never your thing, surely you’ve uttered “I don’t have enough time to do that” or “I wish I had more time.” So what happens when you have enough time? Why is it a little overwhelming to even contemplate what that will feel like?

Make a Plan

The reality is that, without a plan, the time you have in retirement can serve as both a blessing and curse. Not surprisingly, people who plan their retirement are less likely to feel depressed or have difficulty adjusting. The experts at AARP suggest the following for developing a healthy plan:

• Start early. Begin envisioning what you want your retirement to look like about five years before you expect to retire
• Personalize your plan
• Get your emotional and financial plans in sync
• Find your happy place if relocating is part of your plan
• Explore passions you never had time for
• Consider your relationships. Find your tribes

My Story

I used to imagine what it would be like to be able to freely plan my own days and do whatever I wanted. It always seemed so far off. Then, unexpectedly, the time came. I was dealing with health issues and feeling completely burned out so I stepped away from work. During my “hiatus,” I trained as a coach out of interest and in the hopes it would enable me to better support my health goals and my people. Once my health issues resolved and my burnout subsided, I started to seriously consider what I would do next. The job market proved discouraging and, as much as I grew to love coaching, building a practice requires a level of time and energy that I wasn’t sure I wanted to commit. I volunteered, worked with a few coaching clients, blogged, and started a podcast, all of which sound productive to me now but didn’t at the time. I wasn’t working in the same steady way I used to and wasn’t sure what that meant. My worth and identity had been tied to my working persona and motherhood. I no longer worked and my children were grown up. A lot of life remained ahead of me but I was feeling deeply unsettled about what came next.

With a Little Help From My Friends

My story took an interesting turn on a trip to Vietnam and Cambodia in January 2025 with a group of 12 incredible women who I didn’t know before. At dinner our first night, each person shared a little about themselves. Several of these smart, accomplished, fun, and fabulous ladies were retired. They were all around my age. It had never occurred to me that my status had shifted to “retired.” Almost none of my close friends had retired. But hearing my new friends share their stories, revealing how they’d gotten to where they are and how they were spending their post-work time was eye-opening and liberating for me.

Reframing and Reaping the Benefits

In the days, weeks, and months that followed, I stepped into my own retirement and shifted my mindset, which changed everything. I have reframed blogging, podcasting, and coaching as creative endeavors that align with my values and give me a sense of purpose. They are passion or retirement projects that keep me grounded and bring me joy. As a result of the reframe, I have stopped putting pressure on myself to produce. I have also discovered what it feels like to have time. I have time to exercise, time for myself, time to discover what I want to do and do it. In the course of discovering time, I’ve also discovered boundaries. I have more time than I ever have and I’m so much more protective of it than ever before. As a result, I regularly review the activities and relationships that claim my time.

It took me two years to fully embrace retirement. While that time was put to good use amid self discovery, it was nowhere near as joyful as what I feel now. I share my personal story in the hopes it will resonate with some of you and reassure you that retirement, like midlife, is full of possibilities. Retirement is only an ending if you don’t take the time to meet, greet and celebrate yourself. Take the time. Learn who you are and what interests you most. You are more than the position or title you used to hold. There is purpose beyond a paycheck. Live. It’s your time.

Musical Playlist While You Ponder This Post

When I’m 64 by The Beatles, Take This Job and Shove It by Johnny Paycheck, Take It Easy by the Eagles, 9 to 5 by Dolly Parton, We Gotta Get Out Of This Place by Animal Tracks, Too Much Time On My Hands by Paradise Theater, Celebration by Kool and The Gang

Thinking and Trying

Something to think about: “Half our life is spent trying to find something to do with the time we have rushed through life trying to save.” ~ Will Rogers

Something to try: Whether you’ve retired, you’re contemplating retirement or you’re nowhere near that stage, get to know YOU. Start by asking yourself: If you only had a year left to live, how would your focus change? What would take priority? Who would you spend more time with today? Write it down and read it over.

Join Our Tribe

I always feel smarter and stronger when I listen to and connect with wise people. My friends and fellow coaches Maria and Lorin are among the wisest people I know. The three of us joined together to bring you the Unpacking Midlife With The Wise Women podcast. You can listen on Spotify or Apple podcasts. We share our thoughts, concerns, and joys relating to our journeys through midlife. Whether you’re seeking guidance, validation, or the comfort of knowing you’re not alone, this community welcomes you.

Coaching Can Help

If you’re contemplating retirement or you’re already there but feeling unsettled and unsure how to make the most of it, you might benefit from working with a coach. Contact me here to talk about how coaching can help you develop healthy habits that keep you feeling your best. The first session is 15 minutes over Zoom and it’s free.