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emotional real estate decisions in retirement and remote work

From Sunshine Dreams to Midwest Clarity: What a Florida Condo Taught Me About Real Estate and Relationships

In early 2023, after returning from an overseas work trip, I had what I thought was a brilliant idea: swing through Fort Myers, Florida, and scout for a vacation condo. I was working remotely, the area offered sunshine year-round, and there were direct flights to Des Moines—where our kids live. What could go wrong?  

I found a condo on a golf course and moved quickly—made an offer, started renovations, and envisioned a life of warm winters and peaceful mornings. My wife, Debbie, wasn’t entirely on board, but she was open to seeing how it might play out.

The First Visit: Reality Hits Hard

Debbie’s first trip to the Florida condo wasn’t exactly the picture I’d painted.

  • Strike 1: It was blistering hot—Florida in full summer mode.

  • Strike 2: The surrounding neighborhood felt tired and a bit run-down.

  • Strike 3: The condo wasn’t just outdated—it was dirty.

  • Bonus Strike 4: No sidewalks meant no safe or scenic walking routes.

Still, I doubled down. I poured time, energy, and resources into renovations. The place looked great by the time I finished. But here’s the truth: I only fixed one of the four problems. The rest weren’t cosmetic—they were about connection, comfort, and lifestyle. 

The Big Lesson: Real Estate Is Emotional, Not Just Financial

Even after a wonderful Christmas in Florida with our kids, it was clear: the condo wasn’t home for Debbie. And if it didn’t feel like home to her, it couldn’t be a long-term win for us.  

By early 2024, we shifted focus. We bought a beautiful home in Iowa—walkable, close to family, and filled with joy and alignment. That move felt right, instantly.

Meanwhile, my dream of a “south camp” began to unravel:

  • The golf course closed down—slated for development.

  • Traffic worsened.

  • Property values declined.

Now, I’m preparing to list the condo—and I’ll likely take a $60,000 to $75,000 loss.

But Here’s What I Gained

âś… Clarity
âś… Emotional alignment
âś… A deeper connection in my marriage

Sometimes, clarity is more valuable than cash.

Your Takeaway: Emotional ROI Matters

When it comes to big life decisions—buying a home, transitioning to remote work, or planning for retirement—don’t overlook the emotional return on investment.

📊 A deal that makes sense on paper can still be wrong in practice if it doesn’t feel right.
❤️ Home should feel like home—to everyone who lives there.

One Simple Exercise Before Your Next Big Decision

Ask yourself:

  1. Who needs to love this decision for it to truly work?

  2. What are the real problems I’m trying to solve—not just the obvious ones?

  3. If this fails, what will I regret most?

Final Reflection: As I Sit in This Florida Condo One Last Time

Right now, I’m writing this from the living room of that same Florida condo—on my final trip here before listing it.

The sun is setting. The palm trees still sway. The air is warm. But something’s different now.

This place gave me clarity. It reminded me that real estate isn’t just about property—it’s about people.
And while I may be closing this chapter, I’m heading into the next one with more alignment, more trust, and more understanding than ever before.

Thanks, Fort Myers. You taught me more than I expected.

What about you?
Have you ever made a smart decision on paper that didn’t feel right in real life?
Let’s talk. 👇

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