Sometimes the stars align and I’m rollin’ with a client base that I love. They inspire me daily, and we collaborate in a way that is otherworldly. “You’re the miracle … ” “No, you are” kind of stuff. This is the sweet spot. It’s exactly why my freelance ass gets up every morning to get down to business. I crack my knuckles, write a love letter/to-do list, and get on with my day.

But there’s always a black sheep. You know, that client that you just aren’t jiving with. It’s tough to concentrate on them because they feel more demanding due to the lack of chemistry. It’s tough to meet their needs because you’re on two different pages It’s even tough to take their calls at times—you know every conversation will be a problem-solving, brain-sucking, nightmare. (Open mouth, insert whiskey.)

Over the years, I have had many of these. The green freelancer moment is when you assume that it’s all them (been there), or you suck it up and get through as fast as possible without learning anything (done that). I am old and senile now, so I see things a little differently. As Seth (pimpdaddy) Godin says when referring to dealing with someone who doesn’t seem to care about your side of the street: “The reason they don’t care isn’t that they don’t know what you know. The reason is that they don’t believe what you believe.” Preach.

Here are some things that I do to work through the process:

Client Derailment

There comes a point in the life of any client relationship when things start to change. It can happen at the jump, right after the paperwork is signed and you press go. But too often it happens after you have been in the trenches together. Fast-paced deadlines make for post mortems on the fly over shots and the next brief.

Getting to the bottom of things

The best thing to do is catch it as early as you can. As soon as you see that there’s an issue:

1. Reflect. Think back to those happy days when you were getting all of the things done together. Where did it change? Was there a specific event or situation? Self-honesty will do wonders here. The trigger may have been you, so it’s important to be ready to admit that.
2. Strategize. I tend to process with my mentors, or write in a journal. Whatever you end up doing, this is the step where you ask the tough questions. What could I do better? Where might I have effed this up? How can I improve? I always mull the client’s actions, as well.
3. Communicate. This is where the rubber meets the road, and it’ll get easier with more experience. I use the compliment sandwich approach, along with a healthy dose of , “Hey, it could be my fault, too.” In short:

– Present briefly what has been working.

– Touch on the changes that you have noticed taking place.

– Come back to a positive note and add in some suggestions that you have for a strategy on how to improve the situation.

– Put the ball in their court

Be honest, be clear, be tolerant, and have a line in the sand. I will certainly compromise, but if it means I have to feel like crap because I just threw my self-respect out the window, I won’t budge.

Getting on with the thing

This process can strengthen your synergistic bond, moving the client from the black-sheep pile into the everloving “I would do this shit for free” group. Hallelujah!

Sometimes, though, you have to cut your losses and get the heck out. When I do this, I try to suspend judgment and grab every damn thing I can take with me (pencils, laptops, those fucking sticky notes that do that accordion thing) … I kid, I kid. I just take all of the lessons and move on *insert power song*.

What’s next?

Get up, crack your knuckles, and get on with it. It’d be boring if things like this never happened, and now you are that much closer to being an actual adult or something.