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Thrice, I’ve been involved in business-related lawsuits.

The first time, an agency subcontracted my agency SuperFriendly to do work for a client through them. The work was ambitious and exciting, and it had a ridiculously tight deadline. Our team came up with some pretty creative solutions that worked within agreed-upon constraints. In the meeting where I was supposed to present the ideas to the client, the agency’s CEO—who hadn’t been involved in the work at all—took over the presentation and promised all sorts of outrageous things to the client that were nearly impossible to pull off and certainly by our very real deadline. The client was thrilled; my team was mortified. The next day, we decided to withdraw from the project. I asked the CEO to pay us a prorated amount that they owed per our contract for the work we had done. He threatened to sue me instead for leaving them in a tough spot with their client.

The second time, we finished a project for a client. We delivered everything as expected and sent a final invoice for $12k. The client, who, to this point, had constantly showered the team with compliments and assurances of how thrilled he was with the work, said how unhappy he was with the work and refused to pay the final invoice. I decided I would eventually be willing to sue him to get that money.

The third time, I hired a team to do some work for me. They made a serious error in their work that I didn’t learn about until months later, costing me tens of thousands of dollars. I decided I would be willing to sue them for at least the incurred fees and the fee for their service.

As an added kicker, all three of these things happened within weeks of each other.

I never thought I’d ever sue anyone in my life, or even consider it. I’m generally a “it’s not worth it” kinda guy. I tend to see most things as a learning experience, even at my own expense. Typically, I would have walked away from all of those scenarios: I would have tried to convince the first CEO to call it even, I would have accepted that I’ll never get that $12k, and I would have ate the fees and concluded that the lesson was to “never hire that company again.” Add to that my childhood belief growing up in church that suing someone was un-Christian-like.

So what made me decide to go through with these lawsuits?

A conversation with my wife.

Em said, “You’ve never been through a lawsuit before, so you don’t know what it’s like. Why not go through it enough to know what it’s like? You won’t be any worse off than you are now. It’ll only cost a little bit of money and time, and you’ll learn a lot more than you would by walking away. If it gets to be too much time or money, you can always walk away then, which would still have you learn more than if you walked away now.”

She was totally right. I was afraid of being in a lawsuit, because it’s scary. But, I realized that I didn’t even know what was actually scary about it. The idea was scary, but was there actually anything to fear? It seemed worth finding out.

When you’re facing something you dread, consider doing it just enough to know if you’d do it again.

—Dan

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