Rock bottom doesn’t bounce you. It drags you. And I had to run this checkup on my own stuff before I had any business running it on yours.
I’m an optimist. To a fault.
My favourite lie has five words in it. “It’ll come back, I’ll hold.”
I’ve said it to myself about properties. About projects. About a website rebuild I’ve been over-engineering for longer than I’ll admit in writing. The story is always the same. Don’t decide. Don’t move. Just wait, and the problem will quietly fix itself while I look busy doing something else.
And the checkup I avoid the longest is the honest one. The real numbers on my own stuff, today’s numbers, not the version I tell at dinner. Because deep down I know the number might hurt. And if I don’t look at it, I don’t have to feel it.
So take my advice on this one. I’m the guy who needed to hear it first.
I’m writing this with my own name already on the list.
The two friends nobody compares
I’ve got a friend. A handful of properties.
He bought them at the absolute peak. The market had gone to Vegas. Everybody was up late betting it would never end, and he got swept up in the same hype as the rest of the room. Then the hangover hit. The mortgages were underwater almost out of the gate. For years, he owed more than the properties were worth. He had two choices, and he names them himself: throw the keys back on the desk… or bear down and work through it.
He bore down. Didn’t panic. Didn’t run. Self-managed every door. Paid them down month after boring month. Rehabbed them when they needed it. Held the line on who he let move in. No drama. No hero story. Just relentless.
Twenty years later, the mortgages are sitting at zero, or close enough it doesn’t matter. He’s walking away with roughly $1.2 million. Virtually tax-free, because he’s not even back to what he paid, so there’s almost no gain to tax.
He didn’t time the bottom. Nobody times the bottom. He decided at the bottom, and then he did the work for two decades.
Now the other story. The one that never makes the highlight reel.
Same kind of start. Same market punch. Same exact wish, that it would come back. Different investor, though. And at the fork, instead of going to work, this one went quiet. Told themselves it’ll come back, and then did the most dangerous thing you can do with a property you’ve quietly given up on.
Nothing.
Stopped doing the work. Stopped updating the units. Let the tenant criteria slip, just a little, just this once, just to keep it filled. And every new tenancy that rolled in was a notch rougher than the last. The properties got tired. The tenant base got harder. The whole portfolio slowly rotted from the inside while the owner sat still and waited for a rescue that never came.
Then the cruelest twist of all. When the market FINALLY started to turn back up, that’s the moment they sold. Bailed right as the wave was forming. Ate the loss on the way in, AND missed the recovery they’d white-knuckled for a decade to see.
Two people. Same hole. Same hope. Both of them wanted it to turn around. Both of them held on. The difference was never the market, and it was never even the holding. One did the work while he held. The other covered his ears and called it patience. That is the whole story.
The picture I can’t unsee
A boat that won’t sink and won’t sail.
Anchor snagged on the bottom. Engine running. Going nowhere. The hull scraping raw across the rocks, season after season, while the captain keeps telling the crew the wind is about to change.
That’s not rock bottom bouncing you back up.
That’s rock bottom dragging you along. Year after year. Purgatory on a ten-year lease.
The part that stung me first
Here’s the truth, and it cut me before it cut anyone reading this:
The loss isn’t what kills you. What you do in the long stretch after it does.
The market took the equity. Fine. Markets do that. It’s the deal you signed. But the market didn’t make you stop doing the work. You did. I did.
And hear me clearly, because this is the easiest thing in here to take the wrong way. I am NOT telling you to sell. Holding is not weakness. Holding for a long time is often exactly the right call. My friend held for twenty years. The question was never hold or sell.
The question is what are you doing while you hold?
Rolling up your sleeves, getting your hands dirty, chasing down every fix? Or sitting in the boat with your hands over your ears going la la la, everything’s wonderful, it’ll all come back?
One of those is patience. The other is denial in a patience costume.
Same problem. Same intention. Both wanted it to get better. One did the work. One didn’t. That is the entire difference, and it sits 100% inside your control.
Rock bottom doesn’t bounce you. It drags you. And the rope doing the dragging is the work you keep finding reasons not to do.
The checkup from the neck up (do this tonight)
You don’t fix this with a feeling. You fix it with a checkup. Checkup from the neck up. Here’s the whole thing, and you can start it before you sleep.
- Lay it all on the table. Every property. Real numbers, today’s numbers, not the comfortable story. Cash flow, debt, equity, what it actually costs you in hours and headspace. The good, the bad, and the ugly. All of it, naked.
- Sort every door into one of three buckets. Good = it’s healthy, it’s working, it’s an asset. Bad = fixable, but it needs a decision and probably some money. Ugly = it’s bleeding you, and somewhere in your gut you already know it.Here’s the move most people are too precious to make. Good does not automatically mean keep. Sometimes the smartest play in the whole portfolio is to sell a GOOD one… the clean one, the one with all the equity… and use that capital to fix the bad and put the ugly out of its misery. You’re not selling the winner because it failed. You’re selling it because it’s the healthiest source of the cash the rest of your portfolio is screaming for. The good property is often the cleanest lever you’ve got. Don’t refuse to pull it just because it’s the one that hurts least.
- Pick a lane on every ugly one. Three honest options, no fourth.
- Hunker down. My friend’s path. Decide to hold HARD, on purpose, eyes open. But hear this clearly, because it’s the whole point: hunkering down is NOT freezing. He didn’t just hold and hope. He kept doing the work. Self-managed, paid down, rehabbed, held his tenant standard like a fence. Holding without the work isn’t a lane, it’s the slow rot from the story above. Choose this only if you’re choosing the work that comes with it.
- Rip the band-aid. Sell it. Take the loss, free the cash, free the headspace. The loss you choose beats the drag you don’t.
- Prune. The hybrid. Trim the ugly, protect the good, restructure the rest. Cut to save the tree.
- Make ONE decision before you sleep. Not all of them. One. Movement creates movement. A frozen portfolio thaws one decision at a time, the same way it froze.
One rule, no exceptions: holding is allowed, hiding is not. You don’t get to put your hands over your ears, call it “wait and see,” and pretend that’s a strategy. That’s not a lane. That’s the drag, wearing a suit and carrying a clipboard.
We’re in the same mirror
I’m not writing this from a mountaintop. I’m writing it from the same mirror you’re standing in front of. I’m the optimist who’s held too long. I’ve got my own ugly column, and I’ve been finding reasons not to look at it. I’m running this checkup on my own stuff this week. I’d bet you’ve been putting yours off for a while now too.
You’re worth the honest number. Even when it hurts. Especially when it hurts.
The investor who decides at the bottom is already on the way up. The one who waits is just getting comfortable being dragged.
Don’t get comfortable.
Run the checkup tonight. Make one call. Then move.
Want a second set of eyes before you decide?
If you’ve got an ugly column you’ve been avoiding, and you want someone to run the hold-sell-prune call with you before you pull the trigger, that’s exactly what I do. No pitch, no pressure. Just an honest checkup with someone who’s been dragged and decided to row instead.
Book a free consultation here and let’s run it together.
In your corner,
Russell Westcott
#Inspire # Encourage #Love
