Updated June 14, 2026
I’ve been very lucky in my career. The vast majority of my clients are wonderful people — smart, communicative, collaborative, and a genuine pleasure to work with. I don’t take that for granted for a single day.
But I did once take on a client I shouldn’t have. And I stayed far longer than I should have. This is that story.
The opportunity that wasn’t
During a period when work was harder to come by than usual, I met a potential client who seemed to represent exactly what I needed — a continuous stream of projects that could keep me busy for years. It was the kind of opportunity that, under normal circumstances, you’d be excited about.
Except that during our very first meeting, my gut started talking. Loudly.
Here’s what I noticed right away:
- An unfounded suspiciousness that had no basis in anything I’d done
- Complaints about the previous designer — detailed, pointed, and delivered with relish
- Demands for a non-compete agreement that I later learned was actually unlawful
Red flags everywhere. And I chose to ignore every single one of them.
Why I stayed
We got the work. And for a period of time, it kept us afloat. I am genuinely grateful for that — it was a difficult time and the projects were real. But with that relief came something else entirely, because this person turned out to be one of the most difficult clients I have ever encountered.
Here’s what working with them actually looked like:
- Never satisfied with anything, no matter how much effort went in
- Constant requests for deeper discounts — despite already being offered preferential pricing
- Demands for free work, from me and from others I brought in
- Pressure to take on more and more scope with no corresponding increase in pay
- Chronically late payments
- Ongoing unwarranted suspicion and an “or else” atmosphere that permeated every interaction
- Massive overreaction to any pushback, however mild
- A pattern of scapegoating and triangulation that made every project harder than it needed to be
I stayed anyway. I kept thinking that if I just tried harder, communicated better, delivered more, the relationship would eventually turn a corner. That this person would see me for what I was — someone working in good faith, with integrity, doing their best every single day.
That corner never came.
The real cost
I finally quit — and I quit while this person still owed me a significant sum of money. That’s how done I was. The feeling of relief when I walked away was immediate and profound. Giddy, even, despite the financial hit and the thin pipeline I was walking back into.
But here’s what I hadn’t fully reckoned with: the true cost of that relationship wasn’t just the money I never collected. It was the time I had spent trying to please someone who couldn’t be pleased — time I wasn’t spending on finding better clients, building better relationships, and preparing for the inevitable day when I’d have to leave. I had let one difficult client consume so much of my attention that I’d neglected my own business in the process.
That’s the real cost of a difficult client. Not just the hours. Not just the unpaid invoices. It’s the opportunity cost — everything you could have been doing instead.
Trust the gut
There’s a line from the film “The Apartment” — Shirley MacLaine’s character says “Some people take, some people get took. And they know they’re getting took and there’s nothing they can do about it.”
I beg to differ. We may get took once. But we can learn not to get took by the next taker.
The lesson I carried out of that experience is this: no short-term opportunity is worth the long-term cost of a client relationship that your gut is already telling you is wrong. The gut does not lie. If it shouts at you — or even rumbles quietly — pay attention. Back away. Let the opportunity go to someone else.
I’ve passed on projects since then that gave me that feeling. I don’t know for certain whether my instincts were right in every case. But I didn’t stick around to find out — and I haven’t regretted a single one of those decisions.
I’m out of that situation now, and I have no regrets about leaving. It was a hard and expensive lesson. But I am stronger for it, my business is healthier for it, and I have met so many wonderful clients since then who remind me why I do this work.
Those are the people I want in my corner. And those are the people I want to be working with when I show up every day.
If you’d like to know what the red flags look like before you’re in too deep, this post is worth a read. And if you’re a good client looking for a designer who will show up fully for your project — let’s talk.
And that’s the way it crumbles, cookie-wise.
Transcript
MacLaine: Do you mind opening that window?
Lemmon: Now don’t go getting any ideas, Miss Kubalek.
MacLaine: I just want some fresh air.
Lemmon: It’s only one story down, the best you can do is break a leg.
MacLaine: So they’ll shoot me, like a horse.
Lemmon: Please, Miss Kubalek, you gotta promise me, you won’t do anything foolish.
MacLaine: Who’d care?
Lemmon: I would!
MacLaine: Why can’t I ever fall in love with someone nice like you?
Lemmon: Yeah, well, that’s the way it crumbles, cookie-wise. Go to sleep.
