After running a digital agency for over two decades, I’ve worked with a lot of clients. Most fall somewhere in the middle — fine relationships, reasonable expectations, forgettable in the best way. But a few stick with you, and not always for the same reason.
Two of them have been with me for over ten years. Both started around the same time. Both needed real technical help to build and grow their businesses. The outcomes couldn’t be more different — not in what I built for them, but in what those relationships turned into.
The First One
He ran a daily newsletter — a mailer that went out every morning to a loyal subscriber base. When we started working together, the technical side of things was a mess. Old infrastructure, brittle delivery systems, no real process. We rebuilt it together, and it became something solid.
The relationship was easy in the best sense. He was straightforward about what he needed, fair with fees, and genuinely appreciative. When things broke — and things always break — there was no blame, just a call and a problem to solve together.
Then he passed away. His wife took over the business. The relationship stayed intact. She trusted the work because he had trusted it, and we kept going.
Eventually, the company was sold. A new owner is in the picture now. I’m still serving them — the same systems, the same care — but I don’t know what happens next. That uncertainty is fine. Fifteen-plus years of good work buys some goodwill, on both sides. Whatever comes, I know this relationship was built on something real.
The Second One
She was building a corporate training business when we first connected. There was no tech foundation yet — just a vision and a lot of manual work. I built the online infrastructure from scratch: the websites, the apps, the systems that let her business actually run.
For years, it worked. When she said the business was struggling at one point, I helped anyway. That’s what you do when the relationship feels like a partnership.
Then the pandemic hit. Revenue dried up across the board. Some of my invoices went unpaid. I didn’t push it. Everyone was absorbing losses, and I figured the relationship was worth protecting.
She rebuilt. I helped with that too. At some point, she started learning some of the technical side herself — WordPress basics, some content management — and I thought that was a good thing. Knowing your own systems is smart.
Then she broke something trying to do it herself. That’s also fine; it happens. What wasn’t fine was the phone call on Christmas Day demanding I fix it immediately, with a tone that made clear she thought this was simply owed to her.
I fixed it, because I did what I always do. But that call was the end of something I’d been ignoring for a while — a relationship where the care had never really been mutual.
I ended the engagement shortly after. It was long overdue.
What I’ve Taken From Both
I don’t think the second client is a bad person. I think the dynamics of the relationship were never clearly defined, and I let that slide for too long. When you build someone’s business from the ground up and absorb their hard times without adjustment, you’re implicitly teaching them what to expect. That’s on both sides.
The first client worked because there was a foundation of mutual respect from the beginning. Fees were fair, communication was honest, and when circumstances changed — dramatically, with the death of the owner — the relationship survived because it had been built on something more than convenience.
The lesson for agencies: not every long-term client is a good client. Duration isn’t loyalty. Some relationships persist simply because you haven’t had the conversation that would end them. The Christmas Day call was the clearest possible version of a message that had been building for years.
The lesson for clients: the people building and maintaining your technical infrastructure are not on-call utilities. The ones who stay with you through business struggles, pandemics, and ownership transitions do so because they chose to. That choice can go the other way too.
What’s Still Unfinished
The first client situation is genuinely open. A new owner means new priorities, new budgets, possibly a preference for new vendors. I’m not sure how it ends. I’m showing up the same way I always have and we’ll see what holds.
The second situation is closed, but it left me thinking about how I qualify clients now — not just at the start, but as the relationship evolves. I don’t have a clean system for that yet. I probably should.
If you’ve been on either side of a relationship like this — as an agency or as a client — I’d be curious what the turning point looked like for you.