Seventeen Seasons
A pool guy, a postcard, and the second job most contractors never meant to take.
The Jump
I found a new pool guy in our town's Facebook chatter. Talking to him last week, he told me he'd gone out on his own after 17 seasons with the same local company.
The catalyst wasn't some dramatic falling out. Nobody got fired. Nobody got cheated. The company hired another technician last summer, and the available work got split between two people instead of one. His routes got smaller. His income got smaller. By his estimate, his earnings eventually dropped by about half.
At some point, he looked at the math and made a decision that was equal parts terrifying and responsible.
If he was going to work this hard, he'd rather do it for himself.
So he started paying for his own gas. His own insurance. His own equipment. He traded the security of being an employee for the uncertainty of being an owner.
He also gained something.
Control.
Nobody decides how many pools he services this season. Nobody decides whether he gets the better routes. Nobody decides if another hire cuts into his livelihood. The wins are his. The mistakes are his. The customers are his.
I asked him how his first solo season is going: "I wish I'd done this years ago."
The Second Job
When you go out on your own, you don't just take ownership of the work. You take ownership of everything surrounding the work.
The pool guy already knew how to clean pools.
The electrician already knows how to wire a panel.
The HVAC technician already knows how to diagnose a system.
The challenge isn't the trade. It's all the other jobs that suddenly come with it.
You become the person who follows up on estimates. The person who remembers to send invoices. The person who answers the phone, schedules work, keeps track of customers, and somehow knows where everything stands at any given moment.
Most owners don't realize how much time that second job eats until they're doing it at night. And then they discover that business growth has less to do with being a great technician than they thought. In slow seasons, you become a marketer. In busy seasons, you become a delegator. Either way, the work extends far beyond the trade itself.
The Postcard
Because I can't help myself, I started tinkering.
In exchange for a few pool cleanings and a free pool closing this fall, I built him a few things.
One of them keeps an eye on new pool permits. When one appears, our little agent friend sends a postcard.
That's the entire strategy.
A homeowner who is putting in a pool today is a homeowner who may need pool service tomorrow. The technology involved is far less interesting than the timing.
Our postcard shows up before the competition in town has even reached out.
We built a few other little helpers, too. The kind of things that keep opportunities from slipping through the cracks. The kind of things that make sure work keeps moving even when you're busy doing actual work.
I'm intentionally being vague because the specifics aren't really the point.
What Changed
For years, the answer to almost every problem was another person.
Need better follow-up? Hire someone.
Need help staying organized? Hire someone.
Need somebody to remember all the things you're forgetting? Hire someone.
Sometimes that's still true.
What's different now is that there are suddenly a lot more options between doing everything yourself and hiring another employee.
That's what I find interesting.
Not the demos. Not the jargon. Not the predictions.
The pool guy doesn't need a robot. He needs help with the second job he never meant to take.
And more and more, that's possible.
The Real Story
It's tempting to make this story about AI.
It isn't.
It's a story about a tradesman who spent 17 years building someone else's customer base before finally deciding to build his own.
The postcard matters. The automations help. The little systems are useful.
But they're supporting characters.
The real story is a guy who bet on himself and wishes he'd done it sooner.
The technology just makes that bet a little easier to make.