16 Moves, 15 Homes, and One $250k Tax Bill: What I've Learned About Letting Go

by Rebecca Monson

I've moved 16 times, and I still cry every single time we sell a home.

My husband and I have built 15 homes together over the past 25 years. You would think by now I would have this whole "selling a home" thing down. But nope. It still feels like a breakup.

Take our last move.

We lived in a home that I absolutely loved. The neighbors became friends. The walking trails were just steps from our door. The location near town meant we could bike to Truckee Thursdays, the Air Show, and even run errands on two wheels. I knew every creak in the floorboards. I could navigate that house in the dark without stubbing a toe.

And when it was time to sell? I mourned it.

That is the part people do not talk about.

The Mourning That Comes With Selling a Home

Homes are more than just four walls and a roof. They are vessels for memories.

First steps. Birthday parties. Quiet mornings with coffee on the porch. The spot where our dog Angus loved to nap in the sun. The kitchen island where we made pancakes on lazy Sundays. The garden we planted and watched grow.

Saying goodbye to a house means leaving behind all the routines and rhythms that made it feel like yours. It is not just a transaction. It is a transition.

I have seen this same feeling in so many of my clients. Especially those selling second homes in Truckee.

They bought the cabin for ski weekends and long summers. Their kids grew up there. The memories are woven into every room—the bunk beds, the fireplace where they roasted marshmallows, the deck where they watched fireworks over Donner Lake. And then life shifted. The kids got older. Work changed. The house stopped fitting the life they were living.

That is when the hard conversations start. The guilt of letting go. The fear that selling means losing something irreplaceable. The anxiety about timing the market, paying capital gains, and navigating a process that feels overwhelming.

What 16 Moves Taught Me About Letting Go

After 16 moves, I have learned something that changed everything.

You are not saying goodbye to the memories. You are saying thank you. And then you are making space for a new chapter.

The memories do not stay in the house. They stay in you. The home was just the container. You carry the important parts forward.

And here is the truth I share with every client who is hesitating:

If the house no longer fits the life you are living, holding onto it is not honoring the past. It is delaying your future.

The Tax Mistake That Cost Me $250,000

I mentioned I have built 15 homes. What I did not mention is that I once wrote a check to the IRS for $250,000 because I did not understand the tax implications of a sale.

Yes. A quarter of a million dollars. Because I timed a sale wrong and did not ask the right questions.

That mistake is why I do what I do now.

I am not just a real estate agent. I am someone who has paid the stupid tax so you do not have to. I know the capital gains rules. I know the 1031 exchange loopholes. I know what happens when you sell a primary residence versus a second home. And I know the questions most agents are too afraid to ask because they do not want to admit they are not sure.

I am not guessing. I have bled equity. I have made the mistakes. And now I use those scars to protect my clients.

Why Vulnerability Is My Competitive Advantage

Here is something you will not find on a Zillow bio.

No other agent in Truckee is posting about crying over a sale. No other agent is admitting they paid a massive tax bill. No other agent is struggling publicly with their own mom's move and sharing what that felt like.

That vulnerability is my edge. And I own it.

Because selling a home is not just about comps, staging, and negotiation. It is about emotion. It is about trust. It is about walking alongside someone during one of the most significant transitions of their life.

I am here to advise, guide, and help you navigate not just the transaction—but the emotion that comes with it.

The best partnerships view the whole picture. And the whole picture always includes the heart.

If You Are Feeling the Shift

Maybe you have been in your Truckee home for 10 years. Maybe you bought it for ski weekends and now the kids are grown. Maybe you are looking at the repairs and wondering if it is time to let someone else take over.

If you are feeling that shift—that quiet whisper that says it might be time to let go—you are not alone.

And I would be honored to walk alongside you.