I bought a property years ago for $350,000. Today it’s worth $700,000. Someone asks me: “Would you buy it today for $700,000?” And suppose my answer is: “Hell no.”

Well, then why the hell do I still own it? Every day I don’t sell, I’m effectively choosing the property over the $700,000 I could have instead.

That’s an uncomfortable way to look at something I’ve owned for years. And maybe that’s part of the problem. You get tired of your own stuff.

I’ve had this property forever. I know every room, every repair, every tenant problem, every stupid little thing that goes wrong. Meanwhile, another property comes along and looks fresh and interesting. Maybe I’m not actually tired of my property. Maybe I’ve just owned it long enough to know all its faults and forgotten all the reasons I wanted it in the first place.

We do this with cars. Guitars. Houses. Probably marriages, if we’re not careful. The thing we have becomes ordinary. The thing we don’t have still has some mystery left. So I have to be careful not to mistake familiarity for a bad investment.

There may also be very good reasons to keep it. Maybe I have a 3% mortgage I’ll never see again. Maybe selling means taxes, commissions and closing costs. Maybe the tenants are reliable. Maybe I know the building so well that when a pipe makes a strange noise in February, I know exactly which pipe it is. That knowledge has value.

But there’s a trap on the other side too: “I only paid $350,000.” Who cares? If the property is worth $700,000 today, then I have $700,000 tied up in it today. What I paid is history.

So I don’t think the rule should be: "If I wouldn’t buy it today, sell it." Too simple. But I like the question because it forces me to defend the decision I’m already making. If somebody handed me $700,000 cash this morning, would I use it to buy this exact property?

Maybe yes. Maybe no. But if it’s no, I should know why I’m still holding it. Cheap financing is an answer.

Taxes are an answer. Reliable tenants are an answer. Knowing the property inside out is an answer. Even realizing I’m just bored with something good because I’ve owned it too long might be an answer. “Because I already own it” isn’t.

Buying is a decision. Selling is a decision. And holding is a decision too. It just doesn’t feel like one because nobody puts a contract in front of me and asks me to sign it again every morning.