Differing Views on Retirement

Not everyone loves it (although I do)
Reflections
Retirement
Retiring
Author

Sharon Machlis

Published

September 27, 2026

I had the chance to chat with a few people about retirement recently, including acquaintances and strangers in addition to family and friends. And, viewpoints were mixed. Some thoughts on those encounters below.

First, to set the stage properly: These all involved people with decent health, financial resources, and no crushing caregiving responsibilities. Experiences can be very different if not all of those are true.

One man I met at a party said of retirement: “I tried it. I didn’t like it.” He had been a manager, and it makes sense that if your work satisfaction came from managing a large team with important responsibilities, it might be tough to replace that.

He decided to go back to school and returned to work in a different but adjacent field. Good for him to figure out a new career in his next chapter! There’s no one path to post-main-career happiness. I sometimes need to quash the voice in my head that says it’s our unhealthy, work-obsessed American culture that drives some people to need paid employment in order to be happy.

As we chatted more about retirement, that man also told me someone else he knows retired more recently and still needs to figure out what to do with himself. There can be a lot of newly free time if you worked a demanding job!

Most of my retired friends see this as a gift, not a problem. We’re incredibly grateful to have so much more control over our own time. But that’s not how everyone views it.

Lesson here: Think about what you liked – or loved – about your job. Can you replace that with something similar?

For example, one of my favorite work activities was writing breaking news on deadline. I don’t do that for commercial media anymore, but I do run a neighborhood blog and email list where I occasionally write time-sensitive news; and a weather email list (long story) that’s been around for 30 years or so. My audience now may be hundreds (or dozens) instead of tens of thousands 😅, but this public-service work is still satisfying. It also takes a lot less of my time and is considerably less stressful.

I do remember some times in my career when I enjoyed my job and people I worked with so much, that I looked forward to going into the office. I even recall being restless during one vacation where I mostly sat on a beach for a week. It’s hard for to imagine now! But that would have been a terrible time for me to retire, had I been able to.

Toward the end of my career, I worked mostly remote and had less opportunity to actually write or edit. As much as I liked many of my colleagues, it wasn’t the same, since many were in Europe and we wouldn’t have been together in person even if I’d commuted in to the local office.

Another issue to ponder for retirement: Will you be happy hanging around and relaxing for large chunks of your week? If not, are there things you’ve wanted to do that you never had time for when working full time? Or can you think of any? A hobby, a sport, volunteer work, time with family & friends, travel?

Friends who are enjoying their retirement usually tell me they’re doing one or more of those things, whether travel, taking up a sport like pickleball, spending time with grandchildren, doing meaningful volunteer work, catching up on lots of reading, and perhaps doing part-time work or consulting in their field. Although many of my former co-workers who started off freelancing / consulting in early retirement tell me that tends to peter out or at least lessen in frequency after a few years, either because of waning interest on their part or the current economy where organizational budgets are being slashed and non-full-time workers are often among the first to be axed.

Robert Laura, founder of the Retirement Coach Association, “encourages people to first ask themselves three questions,” according to the Kiplinger Retirement Report:

  1. What feels timeless when I do it?

  2. What can I relentlessly pursue without ever growing tired of it?

  3. What is a constant source of energy in both my words and actions?

Others might put it more simply: When are you so much “in the zone” that all other thoughts and distractions fall away?

Another person I chatted with told me he’d been retired for several months and still wasn’t sure if he liked it. And maybe that’s not so unusual either. Retirement is a huge change if you’ve been working full time for decades, and it understandably can take some time to adjust.

However, many of the people closest to me seem to feel like I do: loving this new stage of life. And, for some of us, wondering why we didn’t figure out how to do it a little earlier.


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