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NOTE TO READERS: I’ll be presenting a workshop on “Developing Meaning and Purpose in Your Next Act” at the 2026 Re/Imagining Retirement Summit at Towson University (Maryland) September 25, 9 am – 4 pm. Check it out!
Last week I had a dream about work. You would think that my subconscious wouldn’t still be obsessing about work nine years after retirement, but apparently this is still a topic of chatter behind the scenes.
In the dream I am back at the workplace I left behind in my early 30s. My boss – the best boss I ever had, as it happens – has arranged for me to address the staff about a “legacy publication” and how we produced it in its early days – like, 40 years ago. I start speaking, but nobody gives a flying fig about legacy. Aside from my boss, I don’t recognize anyone, nor can I figure out what work these people do. It doesn’t resemble the publication work familiar to me. There are cocky, self-important producers, executive producers, and creative directors parading around, but I can’t figure out who is responsible for the publication. Where are the editors, I wonder. Finally it dawns on me that whatever they’re doing today is so far beyond me that I no longer have a role in the organization. Then I wake up, ecstatic that I am still retired.
I thought about this dream when I spoke to a friend who is in the throes of a transition from working to not-working, and she is having a hard time. She has always been a Type A, an active person proud of her ability to get things done. But less than two years into retirement, she hasn’t found a channel for her restless energy. The residents in her new senior living facility seem content to enjoy their leisure pursuits, which leaves her cold. She wonders whether retirement has been a big mistake and whether she should jump back into full-time work.
I understand where my friend finds herself, having been there myself once. I offered a few lame suggestions and a platitude or two. What I wanted to tell her – but she was not ready to hear it – is that what she is going through is a normal stage of the transition process sometimes called the “messy middle.” It feels awful, but in time it passes.
The Messy Middle
The original theorist of transitions, William Bridges, declared that transition was a three-step process: an ending (of one reality, such as working), a neutral state (i.e., the messy middle), and a beginning (of a new reality). But when you’re hip deep in the muck and mire of the messy middle, you can’t imagine that anything good awaits you on the other side.
My friend, like many people who committed all their energies to their careers, is discovering that retirement caused losses she had not anticipated – loss of identity, loss of structure, loss of social connections.
People whose identity is closely tied to what they do may find themselves confronting existential questions: Who am I now without work? What am I supposed to do with the rest of my life? What do I even want? Without the structure that a workday provided, they may have lots of time but no idea what to do with it. Their social connections may be missing too, if they consisted primarily of work colleagues.
It’s akin to stepping off the work train and waving goodbye, as the train pulls away with all your co-workers still aboard. As it slowly recedes from view, leaving you on the platform, it hits you that the work train – and your former co-workers – will function perfectly well without you, and soon you’ll be out of sight and out of mind.
That shocking realization is exactly what my dream felt like – that sinking feeling of being left behind, of no longer belonging, of being useless. But I am among the fortunate. In my waking world, I have made peace with all of that. I have no desire to go back.
Now if I can just convince my subconscious of that.
Off the Train
My friend, if she stays open-minded to all possibilities, will eventually make her own peace with stepping off the train. But often it takes time to sort it out. In my own case, I needed four years to find a path that worked for me. Individual mileage may vary.
It may be helpful to remember that all transitions are not smooth. Stepping away from work is a major life event – one of what author Bruce Feiler calls “lifequakes.”
Finding yourself in the messy middle, as stressful as that experience may be, is a good sign that you’re grappling with the big issues: finding a new identity, finding what gives your life meaning, finding how you want to live your next 30 years. Those are the elements of a new beginning.
As for the dreams? Just the occasional reminder that your new beginning is exactly where you are meant to be now.
I wrote my first book while still in biotech. My job was writing submissions to FDA and negotiating about clinical trial requirements. Was so glad to move on to being an author. If I had work nightmares, they’d be about negotiating with the FDA as it exists now. I have lots of compassion for the folks still doing the work I did.
I'd say your writing is a meaningful new reality, and you are far beyond the messy middle!