When someone tells me they’ve found a great property, I don’t automatically agree. I usually want to know what they’re seeing.
Are they seeing the building? The land? The price? The potential? Or are they already seeing the dream of what they want it to become?
There’s a difference.
Sometimes, the property isn’t what people are attached to yet. It’s the picture they’ve already created in their mind.
I can say that because I’ve been that person.
So before I call something a good deal, I want to know the purpose behind it. Is it for your business? Your family? An investment? A long-term hold? A future sale? Or is it something you just fell in love with before you asked enough questions?
The property’s only one part of the decision.
The real deal is what that decision requires from you after you own it.
I’ve learned this through real estate, construction, land development, brokerage, and business ownership. I’ve been through enough real estate decisions to know that a property can look good on paper and still become heavy if too much of the decision is built on assumptions.
I’ve also seen ordinary properties become strong assets because the deal was set up the right way.
I learned this one from my own life.
Years ago, I was out driving on a Sunday afternoon and saw a farm property. There was a large unfinished horse barn on it, and it needed work. But that’s not what I focused on. I saw the possibility.
I’d wanted horses since I was a little girl. Not just one horse. I wanted land. I wanted a barn. I wanted room for horses. I wanted my boys to be outside. I wanted them to have chores, animals, room to run, and a different kind of childhood. So when I saw that farm, I wasn’t looking at it with clear business eyes.
When I saw that property, I was already personally attached to it.
I wasn’t thinking about selling it later. I wasn’t thinking about splitting it someday. I wasn’t thinking about what would happen if life changed.
I was thinking about horses, land, my boys being outside, and waking up every morning with a barn to walk out to. I could see my boys outside. I could see the horses. I could see myself working on that farm and not wanting to be anywhere else.
When something’s been in your heart that long, you don’t always look at it the same way you’d look at someone else’s deal.
To me, it wasn’t just real estate. It was my dream.
And for a season, it really was one of the best times of my life.
I wouldn’t trade that experience. I still wouldn’t trade that season of my life. But I’d ask more questions today than I asked then. When we bought it, I wasn’t thinking about an exit. I was thinking about the life we were creating there. That’s what excitement can do. It can make the dream loud and the practical questions quiet.
If I could go back, I’d tell myself, “Deb, take one more night. Write down what could happen if this doesn’t go exactly the way you think it will.”
- What if life changes?
- What if the work becomes more than we’d thought?
- What if the property needs to be split someday?
- What if the buyer we’re counting on later never comes back?
- What if the part we keep is harder to sell than we think?
Those aren’t negative questions. They’re real estate questions.
People say, “We can always sell it later,” and I understand why they say it. I’ve thought that way myself.
But later still has to have a buyer. And later doesn’t always bring the value you thought it’d bring.
A property can be affected by choices you make early. How it’s divided matters. What happens next door matters. The economy matters. The city matters. The future buyer matters. And sometimes one decision changes the way the whole property lives after that.
That’s what happened to us.
Over time, life changed. The work, the responsibility, and the pressure of carrying that kind of property became real. Then we had an opportunity to sell part of it. At the time, it looked like a good answer. It solved one pressure point. The buyer had a plan for the part they were buying, and we believed there was a good chance they’d buy the other part later. We also believed the remaining property would hold its value on its own.
That didn’t happen. And once the property was divided, we had to live with the way it was divided. That’s the part people don’t always think about.
When you split a property, sell part of it, lease part of it, finance it a certain way, or give up control, you aren’t just making a decision for today. You’re creating a different situation for later.
Once our property was divided, we no longer controlled the whole picture. The use next door, the future buyer, the traffic, the resale options, and the value of what we kept were no longer tied together the same way. What looked practical in the moment created a different set of problems over time.
Looking back, I don’t see that property as a mistake. I see it as one of the clearest lessons I ever had in real estate.
The property itself wasn’t wrong.
The lesson was that every real estate decision has to be tested beyond the opportunity in front of you. That’s why I like to know what the city is planning before I get too far into a property. Most cities have a comprehensive plan. They have to think years ahead because they’re planning for water, sewer, roads, growth, and where they believe the city is going. That information matters.
I don’t want to only look at the piece of ground I’m buying. I want to know what could be coming around it.
That’s also something I learned from new construction.
When I worked with buyers building homes, I’d always talk to them about where they were putting their money. A light fixture can be changed. The carpet can be changed. Countertops can be changed. Trendy finishes can be changed. But the lot can’t be moved. The location can’t be changed. The way the house sits on the lot matters. The floor plan matters. The square footage matters. The quality behind the walls matters. Those are the things that’ll still matter years later.
A lot of people want the exciting choices because those are the fun choices. I understand that. But I’ve always believed that traditional and timeless choices usually serve you better over time than chasing whatever’s popular right now. That doesn’t mean boring. It means thinking about value later, not just what looks good today.
The same thing applies to a real estate deal.
I know how easy it is to get attached to a property. Sometimes it’s the view. Sometimes it’s the building. Sometimes it’s the land. Sometimes it isn’t even what’s there yet, it’s what you can already picture in your mind. That was me with the farm. Vision matters. Creativity matters. But at some point, the excitement becomes the day-to-day responsibility. That’s when you find out if the decision really works.
When I’m working with buyers or sellers, I don’t want to hear from only one person if more than one person is going to live with the decision.
I want to know why the property matters to each of them.
One person may be thinking about the investment. Another may be thinking about the family. Another may be thinking about the work it’ll take, the stress, the payment, or what happens if life changes. Those answers matter.
If they aren’t talked about early, the deal can start moving before everyone’s told the truth about what they really want and what they can really handle. That’s also why I believe you need someone outside the excitement. Not someone who’s trying to sell you something. Not someone who just wants the deal to close. Someone who can look at it and say, “Have you thought about this?”
Looking back, I was too close to the dream. I could see what I wanted it to become, but I wasn’t asking enough about what could change. If I could talk to myself back then, I’d say, “Deb, sleep on it. Ask someone outside the deal what they see.”
Ask more questions. Get another perspective before giving up control of something that may not be easy to put back together later.
The deal isn’t only what you buy.
It’s what you keep. It’s what you sell. It’s what you control. It’s what you give up. It’s what you may not be able to change later.
Before you ask whether the property is a good deal, ask whether the decision still works if life changes. Ask what happens if the first plan doesn’t happen. Ask who the buyer would be later. Ask what the city has planned. Ask what you get to decide later, and what you’re giving up the right to decide.
Then I’d ask the question I wish I’d asked more clearly:
If everything in my life changed in five years, would this property still be a good idea?
The building may be what people see first.
But the decision behind it is what they’ll live with.
