I’ll be the first person to admit that I’m quick with the ax when it comes time to get rid of a challenging freelance client. Life’s too short to deal with people who make it more difficult.

But I recently ignored my rule and stuck with a high-paying client simply because, well, he was high-paying—and in retrospect, I’m very glad I did. For the first time, I was able to turn a challenging client into a loyal, lucrative one who’s manageable, if still somewhat high maintenance.

Here’s the Reader’s Digest version of the tale. Challenge number one is that he’s overseas, so there’s a time-zone issue. Challenge number two is that his English isn’t very good, so we’ve had a variety of miscommunications. Challenge number three is that he’s very demanding, and needs stuff done RIGHT NOW or he freaks out. Challenge number four is that I often have to get to double-digit drafts before he’s satisfied.

Not the ideal, eh? But the fact was he pays great, so I stuck with it. Over the course of a few months, I was able to preemptively deal with every single one of those challenges:

• Challenge 1: I make sure I check in with him at 7 a.m., and ask if he’ll be needing my attention that day, and if so, when. I check in on weekends if I know something important is on the line.
• Challenge 2: I’ve learned to repeat back to him what he’s said for clarification, so there are fewer miscues. Like, “So, if I am understanding you correctly, you want me to revise Project B before writing Advertisement C. Is that right?”
• Challenge 3: I know that I need to turn stuff around more quickly for him than for most clients, which is fine because he pays a premium. More important, I ask specifically what day/time he wants things—I don’t wait for the “WHERE’S THE PROJECT A OUTLINE????” email.
• Challenge 4: I don’t care about how many revisions there are, and I don’t take it personally if he doesn’t like something. In fact, I’ll usually assume he’s going to hate it, and then be pleasantly surprised when he’s all hearts and flowers.

Would I want an entire roster of clients like this? Heck no! But the fact is that I’ve learned to tilt the love and money equation in my favor. And it’s going to make for a nicer summer vacation than I would have otherwise had.

Question: Have you ever stuck with a client from hell purely for monetary reasons? Were you able to make any progress in turning them into a better client? If so, how?

Jake Poinier answers freelancer questions at Dr. Freelance.