This morning I got a call from my tenants: a squirrel had gotten into the house. Turned out to be a baby chipmunk, but either way, it had to go.
It had wedged itself into the crack beside the dishwasher. I tried to coax it out with the shop-vac, which did not work. Eventually I got it free, at which point it bolted into the living room. So there I was, grown man chasing a chipmunk around with a broom, a couple of my tenants half-helping and half-jumping onto the couch. It was a scene. We finally got the little guy out the door. He was actually pretty cute.
That's how my day started. And somewhere in the middle of the broom chase, it struck me how differently I feel about all this than I used to.
I used to be all in
When I started buying rentals, I was a hundred percent convinced it was the right move. And in fairness to my younger self, it was.
The thing people forget is what I was comparing it to. This was the era of stocks like Nortel going all the way to zero. Against that, a building I could stand in front of felt solid. My projections were deliberately conservative, and we ended up doing far better than I'd penciled out.
There's also a quieter advantage nobody talks about: it's forced savings. A monthly contribution to a mutual fund is optional. You can always skip it when money's tight, and most people do. A mortgage payment is not optional. It gets made, and bit by bit you're building something whether you feel like it that month or not.
When governments print money, it lifts the dollar price of a house. Notice I said dollar price, not value. That distinction took me a while to appreciate.
Why I feel differently at 54
A few things have shifted, and honestly it's partly just where I am in life.
I watch my dad's stock portfolio do very well without anyone ever calling him at 7 a.m. about a chipmunk. There's something to that.
I've also done enough renovations to know the one rule that never breaks: it always takes longer and costs more than I expect. Every time. Even now, with all my experience, I still get surprised.
And the math has softened. Rents in my buildings simply haven't kept pace with what the properties are worth anymore. The returns that looked great fifteen years ago look different today.
So I've been selling one off every year or two. Slowly winding it down. At this stage of my life, owning a pile of rentals just doesn't make the same sense it used to.
I'll be honest about one thing: maybe I'm a little jaded from the recent declines. Mood and timing color how any of us see our investments, and I'm not above that.
This is just my story
I'm not telling anyone what to do here. I'm not in the business of giving investment advice, and I won't pretend the right answer is the same for everyone.
Because it isn't. Being a landlord made complete sense for me at 35 and makes less sense for me at 54. The deciding factor was never really the property. It was where I was in my own journey, what I needed my money to do, and how I wanted to spend my time.
If you're somewhere in that question yourself, I'm always happy to compare notes over a coffee. No pitch, just a conversation. You can reach me here.