Some mornings, I’m thigh-deep in Texas coastal water before most people have had their first cup of coffee.
There’s a quiet just after sunrise on the flats. The tide’s moving. The wind hasn’t kicked up yet. You can feel possibility more than you can see it.
Retirement, for me, feels a lot like that.
Not loud.
Not flashy.
Just… open.
I Didn’t Retire to Stop
I retired at 57.
Not because I was done working.
Not because I hit some magic number.
And definitely not because I had it all figured out.
I retired because I could — and because I was curious what life might look like if I built it intentionally instead of reactively.
For years, I built businesses.
I started a blog in 2004 that unexpectedly took off. That led to a brokerage. The brokerage led to Zillow. Zillow led to stages, boardrooms, and opportunities I never could have mapped out in advance.
It was a great run.
But it was also heavy. Responsibility always is.
Eventually, I realized I had built a career that fed my family. Now I wanted to build a life that fed my soul.
That’s a different project.
The Weird Part No One Talks About
When you retire, people congratulate you.
They don’t talk about the shift.
- The calendar goes blank.
- The identity softens.
- The structure disappears overnight.
For someone wired like me — systems guy, spreadsheet nerd, framework builder — that kind of open space is both thrilling and unsettling.
Freedom is wonderful.
But freedom without intention can drift.
So I started paying attention.
What Makes Me Tick
Clarity over hype.
Tradeoffs over shortcuts.
Frameworks over hot takes.
I like understanding how things actually work:
- Roth conversion timing
- IRMAA thresholds
- Social Security decisions
- Tax cliffs
- Investment allocation tradeoffs
Not because I’m chasing optimization for sport. Because clarity creates calm.
I’m not a financial advisor. I’m a guy who manages his own money carefully, reads the fine print, and has made enough mistakes to respect the details.
You won’t find clickbait here.
You won’t find “secret tricks.”
You’ll find practical thinking from someone walking the same stretch of shoreline.
Life Now
My wife and I live in a 55+ community nestled in the Texas Hill Country. I hold an active real estate broker’s license in Arizona and am pondering getting licensed in Texas.
Afternoons might mean writing, researching Medicare updates, wading neck-deep into spreadsheets, or talking with someone navigating their own transition. I may have a bit of a problem with sports memorabilia… Naps, which are highly underrated, happen regularly. Since having a heart attack 14 years ago at the ripe young age of 51, I’ve been taking my health much more seriously and love the opportunities moving to our new community has provided through classes like “aqua cardio,” strength training, and Tai Chi. Then there are the darts league and poker tournaments.
It’s quieter now.
But it’s not smaller.
It’s more aligned.
Why I Share This
Because retirement isn’t a math equation.
It’s a life transition wrapped in financial decisions.
You can get the numbers right and still feel unsteady.
You can have enough money and still lack direction.
The early months of retirement can feel wide open in a way that’s both liberating and disorienting.
If something I write helps you:
- Avoid an expensive timing mistake
- Think more clearly about a tradeoff
- Feel less alone in the shift
Then it’s worth sharing.
What Matters Most
At this stage of life, I care less about accumulation and more about alignment.
Does this decision make our life better?
Does it reduce stress?
Does it increase agency over time, money, and energy?
Retirement isn’t a finish line.
It’s just a different shoreline.
Some mornings it’s glass calm.
Some mornings it’s windy and unpredictable.
Either way, it helps to understand the tide charts.
Welcome aboard.
— Jay
Professional Bio
Jay Thompson is a retired real estate broker, writer, and speaker with more than two decades of experience in real estate and writing. He founded one of the early influential real estate blogs in 2004, later ran a brokerage, and went on to work as a director at Zillow during a period of significant industry change.
Today, Jay writes and speaks about retirement planning, Medicare decisions, tax strategy, and the emotional side of life transitions. His work focuses on practical clarity, lived experience, and helping people navigate complex decisions with confidence.
He lives in the Texas Hill Country with his wife and a citron-crested named Tomoe. He spends time reading, writing, traveling, wading neck-deep into spreadsheets, and visiting his two amazing granddaughters.