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What was your worst freelancing experience?

Sharing bad experiences isn't just about venting--we can usually learn from others' experiences.

I made my worst client mistake quite late in my career, just a couple of years ago. I cleared a substantial chunk of my schedule for a new client--not just reserving time, but cutting ongoing clients.

Of course, I've said over and over that you should never make changes based on hypothetical work, and I was conscious of that when I made the decision, but I did it anyway because:

  • The new client was a respected player in my industry; I'd known of him by reputation for many years and had many trusted colleagues who had worked with him in the past
  • The gig he pitched was long-term (permanent, if it worked out for both of us) and would have allowed me to shift about half of my work to my favorite slice of my niche, which was currently only a small percentage of my work
  • He gave me a long lead time to make room for him, so that I could phase out, refer out, or rework schedules with current clients and not leave anyone hanging.
  • I had the financial buffer for it not to be a catastrophe if it fell through.

What I underestimated was the catastrophe it had the potential to become in terms of stress, frustration, and reputation. It wasn't that the client didn't come through; he wanted to move forward, and eventually did. But, he pushed our anticipated start date by nearly three months, and never gave me a new date, so I spent a couple of months working at half-capacity waiting to see what was going to happen as he gave me "almost there" sorts of responses. Then, when it finally came time to move forward (I'd lost more than $10,000 in income at that point, but still would have seen it as an investment if everything had gone smoothly from that point), the entire project changed into something I wanted nothing to do with.

So, I basically spent five months rearranging my roster and waiting, cut out several ongoing clients, lived in a constant state of stress with the ongoing "almost ready to move forward" keeping me from commiting to anything else, and experienced crazy-making frustrations with the way the potential client handled the whole thing, only to finally have it come together as a job I didn't want.

I think the key takeaway here is that we can always find a reason to deviate from what we know are best practices, and sometimes it IS warranted. But extensive experience and bulleted lists of reasons it will be okay in this situation don't necessarily make it so.