He said it before I even got through the intro.
“My friend built my website and I can’t tell him it’s not working.”
Tongue-in-cheek, kind of laughing about it — but not really. This was a contractor, a guy who knows how to have hard conversations on job sites all day long, and the one conversation he couldn’t figure out was the one with his buddy who built him a website that wasn’t doing anything.
The Part Nobody Talks About
It’s not that the site was terrible. That’s almost never the problem. The problem is the person who built it put their heart and soul into it. They told the business owner every chance they could, you wouldn’t believe how hard that was for me. And they meant it — because it was hard. They weren’t good at it, and they pushed through anyway, and now there’s this thing sitting online that doesn’t work but carries the weight of someone’s best effort.
That’s what the guilt is made of.
It’s not really guilt at all, most of the time. It’s that this person isn’t going anywhere. They’re not a vendor you can cut loose and never think about again. They’re gonna be at Christmas. They’re gonna be at Thanksgiving. You can cut ties with someone you paid money to do something and it doesn’t hurt you — but this isn’t that.
When the person you’re leaving is a stranger at a company, switching from a bad web company is simple. When it’s someone you love, everything changes.
What Happened on the Call
So we strategized together. This contractor and I, on the phone, figuring out the best way to break it to his friend. I’m dropping little hints — your business is more important than hurting your friend’s feelings — and he’s nodding along but you can hear it, that pause where someone knows you’re right but doesn’t want you to be.
It’s amazing how we feel these devotions to family and friends, but at the end of the day it’s just business. If someone’s better for your business, you might have to hurt someone’s feelings.
That’s not cold. That’s honest.
Why It Was Broken in the First Place
You got to build 50 or 100 websites before you get good at any of this stuff. It’s like anything else — if you’re a contractor that just got out of school, you’re gonna build crappy houses versus the one that has already built 50 or 100 houses. By the 50th or 100th house, you’re building great houses. The first five or ten, you’d be ashamed that you even built them.
Exact same with websites.
The friend’s site might look okay on the surface. You can use Squarespace or any of these other platforms and make something pretty. But they won’t know how to write compelling content unless they’re writers — and even if they’re writers, they won’t know how to make sure the development side, the side you don’t see, is correct. Schema markup, navigation structure, all of it. Nine hundred ninety-nine out of a thousand websites built by friends or family are going to have massive development issues underneath.
The business owner doesn’t see any of that. They just know it’s not working and they can’t say it out loud.
That contractor? He figured it out. The friendship survived, and the business got what it needed. Most people sitting on this exact situation just need to hear that they’re not the first person to be here — and that leaving someone who means well is not the same thing as being ungrateful.
Nobody wants to fire a friend who built their website. If you’re reading this and your stomach just dropped a little — you already know. And we’ve already had this conversation a dozen times with people in the same spot. You’re not the villain in this story. You’re the person who finally decided their business matters, too.
Yeetish Question
What if my friend or family member gets upset when I switch?
They might. And that’s okay. The people who care about you will understand that your business needed something different — and the ones who built your site because they wanted to help will eventually get that helping also means letting go when it’s time. You can cut ties with a vendor and feel nothing. This is harder because the relationship is real. But making the switch doesn’t erase what they did for you — it just means your business outgrew it.