Hey there,

At the start of my business, in classic people pleaser fashion, I took whatever gig came my way. Extra meetings, extra deliverables, extra feedback rounds, all without extra pay? Sure. I thought the more I agreed to, the more work would come my way. Right?

Nearly seven years into this business, I’ve learned to stand up for my time, advocate for my compensation, and trust my judgment instead of twisting myself into someone a client might find more palatable.

In all that time, I’ve learned that my own people pleaser mode can be a nightmare. It’s talked me into saying yes when I wanted to say no, and staying long after I wanted to leave.

And yes, I still catch myself slipping. These days, I pay attention to how a potential client approaches working together, and how quickly I start accommodating them before we’ve even signed anything.

So let’s talk about three kinds of clients who helped me learn all this the hard way. Some were a bad fit. Some tested my limits. All gave this recovering people pleaser something to work on.

My first real client was preparing to launch a product. I was coordinating a small team of five people, putting together the marketing calendar, and creating social media assets. I submitted the work for feedback. Three weeks went by. Nothing.

Then came the complaint that “nothing was happening.” Meanwhile, he wanted more deliverables and two meetings a week instead of our agreed-upon one. The work was sitting there waiting for his input, and somehow the solution was to give me more work.

He was the first client I ever fired. And it put me in a spiral. After rejection after rejection, I finally got a client and I decided to walk away? Fuck. Was I even cut out for this?

It cost me time, energy, and more confidence than I’d like to admit. I learned that I could do my part, but I couldn’t also be the person giving feedback and approving the work.

These days, I’m direct about what’s included in the work I do, what isn’t, and what we can add for an extra fee. All of that I include in the contract, and I say it out loud in sales calls before we start. And after trying it a few times, I realize that it doesn’t really have to be awkward at all: “No, that’s not included in the current proposal. But yes, we can do that. Here’s what it would cost.” After seven years, it became as simple as that.

Ah, a classic. I worked with one for two years. For much of that time, they represented the majority of my income. I was living in Amsterdam, building a business as an immigrant. You can imagine what I was willing to put up with when that much was on the line.

Every little thing needed approval. Decisions we’d already made kept reopening. I’d recommend an approach, they’d insist on another, and when the results weren’t there, I’d be asked why my work wasn’t working.

Look, clients can question my recommendations. But it’s hard to guide the work when your judgment is constantly overridden, and you’re still responsible for where it ends up.

It wore down my confidence. I spent so much time defending decisions and second-guessing myself that I started losing sight of what I actually knew how to do.

These days, I pay attention to how a potential client responds when I explain my approach or disagree with theirs. Questions are welcome. Repeatedly reopening settled points and wanting to dictate every step gives me pause. I need room to do the work they’re hiring me for, and I’m much more willing to say that upfront.

With this kind of client, the expectations only become known when someone is already upset. By then, you’re trying to resolve a problem you didn’t know existed.

One client asked me to write and publish a few blog posts while they were away for three weeks. The editorial direction was vague, but the permission was clear: go ahead. They told me they didn’t know much about SEO or marketing and trusted me to handle it.

When they returned, they were unhappy with the posts. As I tried to explain the approach and discuss changes, the conversation turned into questioning the value of my work altogether. When I explained that additional revisions would cost extra, the response was essentially: “So what did I pay you for?”

They were allowed to dislike the work. But suddenly I was defending my expertise against expectations that hadn’t been shared with me. I thought we had an understanding, and then I was replaying conversations, wondering what I’d missed and how much more explaining would make things okay.

These days, I make room for feedback and try to be as honest as I can about the work. I also pay attention to how concerns are raised. If the conversation turns hostile, I need to protect myself instead of pouring more energy into trying to fix it.

This recovering people pleaser still needs reminding that I can’t do both sides of the communicating.

So there you have it: my nightmare clients, anonymously exposed. These experiences helped me figure out what I need to do good work: clear expectations, honest feedback, and room to use the expertise I’m being hired for. I’ve had plenty of collaborations like that, too… and those deserve a little exposure of their own (make sure you’re subscribed to get that exposé next month).

Want a taste of what we can create when working together is a great fit?