Deciding to sell your home after 20, 30, or even 40 years is like strapping in for a rollercoaster ride. There’s the slow climb of making the decision, the breathtaking nostalgia, the dizzying twists of negotiations, and the final sigh of relief at the closing table.

 

As a real estate broker who specializes in working with Baby Boomers, I’ve been on this ride many times—right in the passenger seat with my clients. Here’s a guide so you can enjoy the view along the way.

 

The Anxious Climb: “Should We or Shouldn’t We?”

This is often the hardest part. You’ll feel a mix of excitement about the future and fear of leaving the familiar.

 

• What it feels like: Uncertainty, endless pro-and-con lists, and sleepless nights.
• My advice: Talk it out. Discuss your fears and hopes openly with your partner. Data can help, too—understanding your home’s value can make the decision feel less abstract.

 

The Big Drop: The Bittersweet “For Sale” Sign

The moment the sign goes up in the yard, it becomes real. This is when the wave of nostalgia hits hardest: bringing your babies home, neighborhood parties, and quiet mornings with a cup of coffee.

 

• What it feels like: Sadness, sentimentality, and maybe a touch of panic.
• My advice: Lean into it. This feeling is a testament to the wonderful life you built there.

 

The Twists and Turns: Showings, Offers, and Negotiations

Keeping the house perfectly clean, having strangers walk through your private spaces, and the back-and-forth of offers can be draining.

 

• What it feels like: Stress, invasion of privacy, and impatience.
• My advice: Find a partner you trust. A good agent acts as your buffer, managing schedules, filtering feedback, and handling tough negotiations so you don’t have to carry that emotional load.

 

The Final Stop: Relief and Reflection at Closing

Handing over the keys is a strange mix of relief, exhaustion, and a quiet sense of accomplishment. The ride is over.

 

• What it feels like: A new beginning, tinged with the sweet sadness of an ending.
• My advice: Celebrate! Look forward to the future to come.

 

No one should ride this rollercoaster alone. Having a steady hand to guide you can make all the difference.