You can’t really plan for your retirement because you’re planning for a person who doesn’t exist yet.
That person will meet opportunities you couldn’t have imagined and may want different things than you do now.
The best move is to make a plan, hold it very loosely, and give yourself explicit permission to throw it out once you’ve actually met the retired version.
I Did Almost None of What I Planned
I had a plan when I retired. I had prepared a mind map filled with activities and possibilities.
I’ve done almost none of them in my retirement.
After retiring, we moved to Sun City West, an adult community in Arizona. Within a year of my retirement, I joined the Sun City West Sheriff’s Posse and stayed with them for five years. I was a board member and a shift supervisor. This was never even on my radar until after I retired.
After moving to South Dakota three years ago, I worked part-time one winter as a ranger for the National Park Service. I now volunteer for the National Park Service. I also work part-time for a creator friend, and I write two blogs on different topics. None of these were on my pre-retirement list.
You’re Planning for a Self You’ve Never Met
The core problem was that my plan was built for a person who didn’t exist yet.
You are planning as the busy working version of yourself on behalf of a retired self you’ve never met. The fact is, you don’t know who you’ll be when you’re retired.
Retirement isn’t just a change in activity — it’s a change in self. Your energy, your sense of time, and what feels meaningful all shift, and none of it can be known from the outside looking in. You have to live it and discover what retirement is like for you.
A Cambridge study of retirement transitions found that retirees who plan extensively reported their plans bore little resemblance to their actual experience.
Retirement coach, writer, and podcaster Dan Haylett wrote about how retirement is different in his newsletter, “The Retirement Fix” for March 15, 2026:
“Retirement isn’t just a change of schedule. It’s a complete identity shift. You’re not the same person you were when you were working. Your energy is different, your sense of time is different, and what feels meaningful or worth doing is different, and you won’t know what any of that actually feels like until you’re in it.”
Retirement Keeps Handing You New Selves
New circumstances you encounter once you’re retired will provide new options. And you’ll have the time to take advantage of those opportunities if you choose to when you’re retired. You’ll find yourself doing things in retirement you never imagined before retiring.
Retirement keeps handing you new selves.
And things keep changing. There’s no static “retired Jim” to arrive at.
I’ve always been interested in many things. My core personality has held steady through retirement, but its defining traits are openness to new opportunities and a readiness for surprise.
Why We Cling to Detailed Plans
We want to have detailed retirement plans in advance because retiring is scary, and having a plan gives us a sense of control.
Dan Haylett names the trap directly in The Retirement Fix:
The plan “feels like control, like you’re taking charge of this massive life transition instead of just letting it happen to you” — but “the more detailed the plan, the less likely any of it actually happens.”
The planning impulse isn’t really about foresight. It’s about soothing the discomfort of not knowing.
We build detailed retirement plans for the same reason we build any plan: to feel in charge of something that’s fundamentally uncertain.
Make a Plan You’re Willing to Abandon
The answer to uncertainty isn’t “don’t plan.” It’s to make a plan you’re willing to abandon.
Its value is psychological. It calms the fear long enough for you to start. The value of a plan is preparation and reassurance, not prediction.
The skill that actually predicts a good transition is comfort with not knowing — being able to say, “I don’t know yet, and that’s OK.”
It’s not about doing the most research, coming up with the most detailed plan, or having the most certainty. It’s being comfortable with stepping into the unknown and knowing you’ll work it out.
Schedule Permission to Toss It
Go ahead and plan for a stranger, then be willing to burn it. Build it, hold it loosely, and schedule permission to toss it.
Make an agreement with yourself that, six months or a year into retirement, you’ll review your detailed retirement plan and give yourself permission to toss it if it’s not really working for you.
That’s not a failure; that’s just recognizing that, when the plan was made, it wasn’t with who you’d be in retirement in mind, but someone else.
Go Meet the Stranger
I planned for a man who never showed up, and the one who did has had a far more interesting retirement than the one I drew on paper. The Sheriff’s Posse, the ranger uniform, two blogs — none of it was on the list, and all of it found me because I left room for it.
That’s the quiet promise underneath all this uncertainty: you don’t know who you’ll be, which means you get to be surprised by him.
Make your plan, hold it loosely, and mark a date to let it go. Then spend less energy bracing for retirement and more getting curious about the person you’re about to become.
Note: I wrote this blog post myself using my own words and thoughts for the initial draft. I used AI only to suggest headlines, section headings, images and text improvements.
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