I Owned Four Houses and Couldn’t Sleep. Selling Two Gave Me My Life Back

A reader writes:

I want to tell you something that I have not been able to explain properly to my own brothers, or to the men I play dominoes with, because every time I try, they look at me like I have lost my mind.

Two years ago I owned four properties. The house we live in, in Mandeville. A two-bedroom flat in Kingston that I rented to students. A small house in May Pen that I bought from my wife’s cousin when he migrated. And a piece of land with a half-finished building on it near Santa Cruz, that I was going to turn into four apartments. I built it up over about twenty years, working as a quantity surveyor in the week and doing my own property business in the evenings and weekends.

I was proud of it. I will not lie. When I was a boy we rented two rooms at the back of a yard in Spanish Town and my mother used to say, “One day, Winston, you will have your own.” I had my own four times over. At church people called me for advice. My nephews asked me how to start.

But I was not sleeping. That is the plain truth. My phone would ring at night and my heart would jump. A tenant in Kingston had a leak coming through from the flat upstairs. The man in May Pen was three months behind and every time I went to see him his wife cried and I left without the money. The building in Santa Cruz had stalled because I did not have the cash to finish it and I did not want to borrow any more, so it sat there with rebar sticking out of the top like it was mocking me. Every weekend was spent driving between four parishes. My wife said she had not had a Sunday with me in years. She was right.

Then I had what the doctor called a warning. Not a heart attack, but close enough that he sat me down and asked me what I was doing with my life. I was fifty-eight. I went home and I could not answer him.

It took me the better part of a year to decide. I prayed about it, although I will be honest, a lot of my prayers were more like arguments. I talked it over with my wife many nights at the kitchen table. I sat with an accountant and an attorney and looked at the numbers properly for the first time in a long time, not the numbers I liked to tell people, but the real ones. What the properties were bringing in after repairs, rates, insurance, the time I spent, the fuel. Some of them were not doing nearly as well as I thought.

In the end we sold the land in Santa Cruz with the unfinished building, and the house in May Pen. The May Pen tenant, I gave him plenty of notice and helped him find somewhere else. I felt bad about it for a long time. Selling the land hurt the most, because that was going to be my big project, my legacy, the thing that would show everybody. I got less for it than I had put in. My brother told me I was a fool to sell at a loss.

Maybe I was. But I paid off what I owed. We kept the house we live in and the Kingston flat, which has a good tenant and a good management arrangement now. I put some aside. And for the first time in maybe fifteen years, I sleep through the night.

I do not want anybody to read this and think I am saying property is bad or investing is wrong. It is how I paid for my children’s education and it is why my wife and I will be all right when I stop working. I still believe in it. But somewhere along the way I stopped owning the properties and they started owning me. I was collecting houses the way some men collect cars, and I was calling it building a legacy when really it was about showing people I was not that boy in the back room in Spanish Town any more.

Now on Sunday I go to church and then I come home and I sit on the verandah with my wife. Last month my grandson came to stay for a week and I taught him to play dominoes instead of driving to May Pen to argue with a tenant. My mother would have been proud of the houses. I think she would have been prouder of that.

I still do not know how to explain it to my brothers. But maybe somebody reading this will understand.

— Winston, Manchester

Editor’s note

Winston’s letter raises a question few of us ask plainly: how much is enough? Scripture does not condemn owning property or building wealth; it warns against letting them rule us. The writer of Ecclesiastes observed that “when goods increase, they increase who eat them”, and that the sleep of a labouring man is sweet while the abundance of the rich will not let him sleep (Ecclesiastes 5:11-12). Winston discovered that truth the hard way. His decision was not about quitting, but about stewardship: looking honestly at the real numbers, the real costs to his health and family, and choosing what he could care for well. If you are building a portfolio, it is worth asking regularly what it is costing, in hours, in rest and in relationships, not only in money.

This article is general information only and is not financial, legal, tax or other professional advice. Please speak to a qualified professional about your own circumstances.

Reader letters may be edited for length and clarity, and names and identifying details are changed.

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