Many of us have freelanced for friends. Perhaps a friend was getting married and needed a photographer or event planner or maybe a different friend wrote a book and needed an editor. It is not uncommon that friends and strangers alike seek out our services. In an ideal world, friendships will remain intact long after freelancing opportunities have faded.

But unfortunately, it doesn’t always work out that way. Mixing expectations, money, deadlines, and a friendly bond can be disastrous as I recently learned. In fact, a 20-year old friendship ended over an unpaid invoice.

A cautionary tale

In early 2017, a dear friend asked if I would be willing to help, in a freelancing capacity, with his book project. Prior to that point, I had worked on several projects for him with no problems. So I did not hesitate. I also did not adhere to my own process — the first of many mistakes that I would make.

Like many of you, typically before starting any project I follow a process — a phone consultation/proposal, legal contract, deposit, deadlines established, project delivered and final payment. The process is seamless and clients are informed throughout.

In this particular case, at my friend’s request, I agreed that I’d invoice him once the project was finished and that he could pay 30 days net. After several versions of the project were created; he accepted the final product and I invoiced him. From there, this story should have ended happily ever after — wrong!

The waiting game

30 days passed by, then 60, then 90, and my friend did not pay the invoice. I sent invoice reminders; I inboxed him on social media and I even reminded him during our sporadic phone calls. His reply was one of disbelief, “Have I never paid you?” In response, I would recoil with guilt because he was right; he did always pay.

My life kept going and his invoice remained unpaid, tucked away in my electronic system until one day, I saw an advertisement for his book. Using the ad as a springboard, I sent him a congratulatory text and reminded him that I still hadn’t been paid. He asked me to send the invoice directly to his accountant and cc him. I did.

Another 90 days would pass by and still no reply. My accountant thought that I was being too gracious and that I needed to treat this as I would any other unpaid invoice — especially one for this amount. I volleyed back and forth with her and continued to make up excuses for my friend. She finally blurted out, “I don’t think he is going to pay you.”

As soon as she said it, my heart sunk. Clearly, he would not use our friendship to avoid his financial obligation? But that is exactly what he did. It wasn’t until my lawyer sent a demand letter that he paid the invoice. By that time, it was almost exactly one year since the original invoice was sent. A few weeks later, he sent me a text stating that I let money come before our friendship; I also learned that he said some disparaging things to some mutual friend. His version of the story failed to include the unpaid invoice. Needless to say, we haven’t talked since this all transpired.

Lessons learned

Although I miss my friend, I know that the erosion of our friendship over business was much bigger than an unpaid invoice. It was a valuable lesson about following my own protocol and procedures, regardless of whom my transaction is with. It was also a valuable lesson about true friendship and integrity. A real friend would never take advantage of a friendship for personal gain.

Since that time, I have freelanced for several other friends and those interactions have been healthy and mutually beneficial. Well after the freelancing has ended, the friendships have maintained. The key is to be clear about boundaries and treating the business-side of the relationship as if it is transactional — because that is exactly what it is. Another valuable lesson is not to deviate from a system that works for you and your freelancing business.

Realistically, if someone is not willing to adhere to your policies or wants to alter things, including payment terms, in ways that you are uncomfortable with then you may need to walk away from that transaction. Ask: Is this really worth changing the nature of how I freelance? Our friendship?

Friends who value your gifts, time, and talent will respect your boundaries and understand what many of us have advocated for years — freelance isn’t free, nor should it be.