Freedom Without a Map
Why the generation living longest in retirement is also the first with no cultural roadmap to guide those decades.
What I read: “Most people don’t realize that the generation currently entering retirement is the first to face a 30-year stretch of unstructured time with no cultural script for how to fill it meaningfully” by Farley Ledgerwood. Published March 29, 2026.
A friend posted the article I’m writing about here as a comment on one of my social media posts about someone I met who’s taking classes for a new career at the age of 70. The article resonated with me as soon as I read it.
In late 2022, I took advantage of an opportunity to leave the company I had worked at for 24 years. It was an amicable separation. My management chain, colleagues, and team members were all wonderful people. I was lucky. Many people report horrific working environments and conditions. I had it rather good.
That said, do I miss my former corporate life? Not at all. But I left what I assumed would be my last corporate job as a healthy person with potentially 20-30 years of life ahead of me. That realization can be daunting.
About a month after I left my job, I wrote “So, About Retirement” in which I explained why I now avoid using the word retirement when I can because I dislike its typical connotation.
For the record, I’m no longer using the word retirement in my daily vernacular when referring to what I see more as a sabbatical than retirement. I needed a break from the day-to-day of corporate life. But by no means do I consider myself retired. There are so many things I want to do and retirement seems like an inaccurate word for my life going forward.
Friends often joke that I am unclear on the concept of retirement because I still do so many things. That’s how I’m wired. I like to create, learn, volunteer, and generally do things that bring me joy that perhaps sometimes also help people and humanity in the process.
I highly recommend a slower pace of life once you’re not chained to a highly structured work life. But I don’t think sitting in front of a television for hours or otherwise engaging in such “passing-the-time” activities ultimately do much to bring us happiness or fulfillment.
A little while ago, my friend Rick retired from his longstanding job. When we met for coffee afterward, he articulated his retirement principles that I expounded upon in “Powerful Perspectives on Retirement.”
However, Rick was clear that he sees retirement much like I do. When I mentioned my reticence to use the word retirement, Rick told me that for his first year he also referred to it as his “sabbatical.” He said he experienced his first year “as a ‘walk-about sabbatical year’ during which he got the lay of the land and focused on observation and recharging his depleted emotional batteries and balance.”
During our discussion, Rick articulated Six Principles of a Successful Retirement that I think deserve a wider audience.
If you are amid retirement or staring at it on the horizon, I encourage you to read Rick’s principles. They’re helpful. Although I don’t abide much by his first and sixth principle, the other four align nicely with my own perspective.
Then along comes Farley Ledgerwood‘s article that eloquently framed another aspect of the situation I find myself in as do many people retiring today. Even though I planned for my post-corporate future with many projects and activities I wanted to spend more time doing, I too initially felt somewhat adrift. From the age of 16 until I retired at 68, I was only unemployed for about three weeks. Losing the workday structure was a bit discombobulating.
What nobody prepared me for — what nobody has prepared any of us for — is that freedom without structure can feel indistinguishable from abandonment.
Longer lifespans and social and business retirement age expectations don’t match up as well as they did in the past. We tend to live longer, but there is no script for retirees today to follow that can guide their next 10, 20, or 30 years.
One thing I’m grateful for is that I never formed an all-consuming identity based on my career or job. Many friends have left their work lives and didn’t know what to do with themselves because so much of their identity was wrapped up in their work. That’s not my situation. But still, it took many months for me to properly adjust to a life no longer dictated by an alarm clock and eight or more working hours five days a week. It felt weird. On some level, it felt like I was slacking off. My hardcore work ethic upbringing stuck with me and it was difficult to abandon.
Intellectually I knew I deserved a less structured and more personally fulfilling life. But accepting that was not easy. But a few months into my post-corporate life I began to recalibrate my life into a pattern that works for me and life nowadays is rather good.
Something to which Ledgerwood alludes is something to which I fell prey immediately after leaving my job – the trap of constant busyness. A life of being always busy trickled over into my life and it kept me from creating a structure and cadence that brought me the most happiness with minimal external expectations.
Busyness is the counterfeit of purpose. They look similar from the outside. From the inside, one sustains you and the other exhausts you.
Check out Ledgerwood’s article. It’s excellent and articulates better than I have thus far a dilemma many of us older people find ourselves in today.
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