Listing while the leverage is on your side makes sense
One of the reasons car dealerships are so frustrating is simple: they understand leverage.
If you’re on a car lot, odds are you need a car more than you just want one. Maybe you’re not desperate enough to drive off today, but you’re on a clock.
They know it. They use it.
The best time to buy a car is when you don’t need one. You could walk away from anything less than a great deal. But then, it often doesn’t make financial sense to make a big purchase before you have to—even if it’s technically a screaming deal.
The job market works the same way. Most people don’t start looking until they’re unemployed. That’s the worst time—because you have no leverage.
My take? Your “real job” is always finding your next, better job. Even while you’re working. That way you only move when the deal is clearly in your favor. If it’s not better, stick where you are.
Spare me the “loyalty” speeches from employers. If it makes good business sense to cut you loose, it would happen yesterday. You know it, I know it, and they know it. Beat them to the punch.
Residential real estate? More like cars. When people sell a house, they usually have to do it now—because they’ve been transferred, are building, or have already bought something else. They take what the market gives them.
Could they make better deals by selling when they didn’t need to? Sometimes. But moving costs, timing, and logistics usually mean they’re stuck navigating the pressure game.
Land is different. It’s more like the job market—if you approach it right. If you own property you’re not living on, there’s usually no deadline. You don’t have to sell—but that doesn’t mean a deal can’t come along that makes sense.
And land values swing more than most people notice. Sometimes a property just checks the boxes for a buyer, and they surprise you with what they’ll pay.
In the residential market, pricing too high almost always backfires. It won’t appraise, loans won’t work, and you either get offers at market—or nothing.
With land, a price above market might still work. You’re under no pressure, so it doesn’t hurt to put it out there and wait.
Not stupid high—if it’s worth around $1M, I’m not putting it out there at $5M.
But 25–30% above recent comps? That might be worth a shot.
Because you never know.
With low holding costs, most people think waiting to sell land doesn’t cost anything. But missing the perfect buyer because your hook wasn’t in the water could cost plenty.
The only real way to miss out is to not try at all.
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