For the first 90 days of retirement, I wandered around my house looking for problems to solve. The pantry got reorganized. Twice. Several aspects of my husband’s business suddenly seemed to need my input. (He was thrilled — NOT.) Nobody warns you about this part — the strange disorientation of stepping off a treadmill you’ve been running on for over 30 years.
Nearly three years have passed since I quit my job at 59. Like many others during the post-COVID “Great Resignation,” I was fed up — but leaving wasn’t the hard part. Finding happiness in retirement when your entire identity was built around being a career woman? That was the hard part.
Calling myself retired felt like giving up, so I refused for a long time.
Now, three years in, I say it proudly. Real joy has found me in this chapter — not the Pinterest version of retirement with infinite beach walks, but something more textured and intentional. It didn’t happen overnight, and I will admit, sometimes I do get bored. Here’s the honest story of how it unfolded.
Year One: Navigating the Retirement Identity Crisis
The First 90 Days
Phase One hit hard: “Oh sh*t — what did I just do?” — I’m only 59!
No paycheck. No defined purpose. Endless, unstructured time. The first 90 days were rough in a way I hadn’t anticipated. Boredom set in fast. Restlessness followed. Quietly, I was terrified I’d made a terrible mistake.
What I Tried
Experimenting became my survival strategy — partly out of curiosity, mostly out of desperation:
Volunteering with Breakthrough T1D. Southwest Florida’s chapter drew me in, inspired by my daughter’s battle with Type 1 diabetes. Helping plan their annual gala was completely different from corporate life — messier, more emotional, and surprisingly meaningful. Something to care about finally existed outside of work.
A real fitness routine. Serious weightlifting got added to my workouts — not just for aesthetics, but to stay strong enough to chase grandkids, carry groceries without wincing, and remain healthy into my 70s and 80s.
A reading commitment. A list got made, and one book a month became the goal. Twelve books a year turned into one of the anchors of this whole chapter.
A summer golf league. Surprisingly, this one wasn’t really about golf. Showing up somewhere regularly, seeing familiar faces, and having something active to look forward to — that’s what it gave me.
Not everything worked. Some volunteer roles didn’t fit (and several got tried). Early mornings proved impossible to sustain. But trying things kept me moving, and slowly, something shifted.
If you’re in Year One and feeling lost: that feeling is normal. It doesn’t mean you made the wrong decision. Keep going.
Year Two: Building a New Sense of Purpose After 60
Midway through Year Two, things started clicking.
More than six months a year in Florida became our new normal, which meant building a new life from scratch — new gym, new social circle, new routines. Exhausting, honestly. But an unexpected kind of intentionality came with it that I found myself enjoying.
The Wins That Defined Year Two
The Breakthrough T1D Board invitation. Being asked to join wasn’t just an honor — for the first time since leaving my career, someone was saying you have something valuable to contribute here. The national One Conference in Houston followed. Coming home, I felt energized in a way that had been missing for years.
Joining a golf course community. Easily one of the best decisions of retirement. Wonderful people, a real social circle, and an improved golf game. Two wins for the price of one.
Portugal’s Douro River. A scenic river cruise in May — our first real international trip since leaving work. Highly recommend. The wine alone is worth the flight.
SPENGA fitness studio. Spin, strength, and yoga combined improved my workouts, yes — but more importantly, new friends came with it, some of whom also played golf. Finding your people in a new place is everything.
Downsizing and decluttering. A new townhouse meant clearing out 20+ years of accumulated stuff to sell our old home. Not fun — but incredibly freeing on the other side. Moving on from our working life finally felt real.
Year Three: Settling Into What Retirement Happiness Actually Feels Like
Recently, sitting in our new townhome, something settled over me that I can only describe as contentment. Retirement doesn’t feel uncertain anymore. It feels intentional.
What Year Three Brought
Taking Social Security. With market uncertainty this year, it gives us breathing room without touching our investments — a decision I’ll write more about soon.
The Amalfi Coast and Sicily. Three weeks abroad — and when would I ever have had three weeks to travel before retiring? Incredible doesn’t cover it.
More grandkid time. This one doesn’t need elaboration. If you know, you know.
Advocate Chair for the Breakthrough T1D Board. Washington, D.C., members of Congress, and a push for critical research funding — three years ago, I would have said that kind of role was behind me. Wrong.
This blog — OverSixtyInsights.com. Which, if you’re reading it, you already know about.
What I’ve Learned About Finding Happiness After a Career
Everyone’s retirement looks different. After three years, here’s what I actually believe:
It Takes Time — And That’s Okay
The identity crisis is real — and temporary. Losing the structure of work will knock you sideways if your life was built around your career. That’s not weakness — it’s just what happens when something that defined you disappears. Grace is what you owe yourself in that disorientation.
Purpose doesn’t retire. The shape just changes. Mine went from managing spreadsheets to advocating for diabetes research funding in front of Congress. The second version matters more, I’d argue.
What Actually Makes the Difference
Connection is everything. Gym friends, the golf community, board colleagues — every good thing in the last three years traces back to people.
Bravery is underrated. Joining a new fitness studio alone, moving to a new city for half the year, saying yes to a board role — none of it felt comfortable at first. Do it anyway.
Recently, a list of 7 Keys to Happiness as We Age from @growingbolder on Instagram stopped me: have purpose, embrace change, stay curious, be kind to yourself, find joy in the little things, stay connected, and practice random acts of kindness. Reading it, I thought — yes, that’s basically the last three years, stumbled into one experiment at a time.
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