When Having It All Figured Out Becomes the Problem
I remember thinking I had retirement figured out. I had a plan. I was wrong about most of it.
Some of us have a personality that likes to plan things in advance. When we go on a trip, we figure out where we’ll spend each night and make reservations, and what we’ll do each day.
This mentality also applies to retirement. We want to have it “all figured out” before we retire. Having a plan helps us to feel in control.
But having a set plan for retirement can backfire. A rigid plan can hinder your ability to adapt to the unknown realities of retirement.
You don’t know what retirement will be like for you until you’re actually retired. You will change during your retirement; your health, interests, and desires will all change.
The Phase Nobody Puts in the Brochure
It’s normal to feel lost and unsettled during this phase. It will take some time before you find a new identity.
In his short TED Talk video, The Four Phases of Retirement, Dr. Riley Moynes described the second phase of retirement (after the initial honeymoon period) as the time of “feeling loss and feeling lost.” When we retire, we lose structure, identity, relationships, a sense of purpose, and a sense of power.
Finding Your Footing Without a Map
As you go through this process, it’s helpful to establish some basic routines and structures.
So, for instance, on Monday mornings, I go to the coffee shop and write. Every morning, I meditate for 10 minutes. Every Tuesday morning, my wife and I go to the gym and walk two miles. These give some structure and routines to my life, even when things are in flux.
You have to trust that eventually, you will find yourself again.
You Will Find Yourself Again — Just Not on Schedule
Allow yourself to feel insecure and uncertain.
Don’t panic. It’s normal.
Give yourself time and don’t force it.
As Dan Haylett wrote in his Retirement Fix Newsletter, February 15, 2026,
“The ones who do okay aren’t the ones who had it all figured out. They’re the ones who gave themselves permission to be a bit lost for a while, and built small practices to steady themselves while they figured out who they’re becoming.”
What’s one small routine that could anchor your week right now?
AI 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.