Me sitting in my backyard contemplating the big question: “To sell or not to sell?”

We listed our house.

The thinking was this: our youngest son is heading off to college, we’re about to be empty nesters, and now seemed like the right time. We live in a great school district — people want to buy in this neighborhood, especially this time of year. If we didn’t list it now, we’d likely have to wait another year to get the price we want.

So we did what everyone does. We painted. Power-washed. Staged the house. Made it shine. We made it look its absolute best.

And that’s when it hit me.

Why the hell did we wait to make our home this good?

Why save the upgrades, the polish, the love for the next guy?

We’ve lived here over a decade. We deserved this version of the house. Not some stranger. That stung.

Then came the second blow: the timing sucked. Our son’s leaving. My wife’s already navigating the emotional weight of that. And here I am, piling on with a rushed plan to sell our home and upend everything.

What happened next?

One showing. Full-price offer. Boom.

And I panicked.

We weren’t ready. The buyers wanted to close fast. We had no clue where we’d go. The dream was to try something new—maybe rent a high-rise, simplify, travel, ditch the homeowner headaches: taxes, maintenance, landscaping. But with a real offer on the table, my wife was upset, the broker was annoyed, and I was spiraling.

I tried to salvage it with two options:

  • Pay us way more to move out quickly.

  • Lease the house back to us until September so we could get our son settled and figure out our next steps. Oh, and the gym equipment and furniture they wanted? Not part of the deal.

The result? Total implosion.

The buyers felt played. The broker was livid—she’d hustled to list fast, showed it privately, and landed the offer. My wife was frustrated by the chaos. And honestly, 

I don’t blame any of them.

I screwed this up.

Looking back, I think we underpriced it. That’s why the offer came so fast. But instead of feeling smart, I got defensive, annoyed at the advice I got, and went into scarcity mode—fear, pressure, counterpunching. The opposite of what I wanted: simplicity, clarity, a smooth transition into this next chapter.

What I Learned

  • Slow down. I didn’t need to counter so aggressively or respond in 24 hours just because they demanded it. A simple, “We need a few days,” or “My wife’s not ready—can we lease back until September?” would’ve avoided the drama. My “pay me enough and I’ll make it worth it” vibe? Not my style. It felt wrong.

  • Upgrade for you. Don’t wait to make your space awesome. New floors, fresh paint, decluttered closets—do it now, for yourself. Enjoy it while you’re living in it. And yeah, this is a metaphor for life, too. Be the best version of yourself now, not just for the next chapter.

So, we’re back to square one. The house didn’t sell. Stress levels are calming down. I didn’t win, but I learned.

That’s midlife—messy as hell.

I still feel like I’m faking this adult thing half the time. But I’m trying. Making better choices, not faster ones. This chapter taught me that creating space—emotionally, physically, mentally—takes time.

Maybe we stay put.

Maybe we breathe.

Maybe we enjoy this home, now that it feels more like home.

And maybe we don’t need to leave to feel lighter.

In Health,

Greg

Midlife Male
52. Husband. Father. Entrepreneur. Coach. Student of the game.
Still walking the walk.

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