Should You Work with Friends? Lessons Learned

Vibe Seven
3 min readFeb 8, 2022
Photo by Surface on Unsplash

Working with people you know is a dangerous game. And I learned my lesson the hard way when a friend almost destroyed my business before it had a chance to get off the ground.

We all know not to mix business and pleasure, but many of us still attempt it anyway. One of the earliest mistakes when founding my new company is one I hope you never have to learn.

I always thought my business associate was like family. We’d worked together for years (although not on this scale). In the past, I trusted him with some of the most important aspects of my business, and he helped me through some really tough times in life. So when I launched my largest business venture to date, he was excited for me and wanted to be a part of the team — but things fell apart almost as quickly as they began.

It was the hardest business lesson of my life — especially since I knew the shortcomings of the arrangement could’ve been prevented.

I’m always the type to mix business with pleasure. From the beginning, I’ve always worked with people I know.

I believe in collaboration and making sure everyone around me who has been a part of my journey gets a chance to rise with me. When working with people you know, that collaboration can be a beautiful thing if the person has the same drive as you do — or it can set your business back further than you could ever imagine.

When collaborating, it’s easy to think of friends as friends first and business associates second. But the moment you mix the two, things can get risky because you’re too comfortable. Missed deadlines, missed payments, sloppy work.

When your friends are involved in your business, they’re no longer your friends during working hours. And they need to understand that you don’t view them as friends in those moments; become business associates, and you’ll need to treat them like one. Once I realized this, however, it was too late. The scope of my years-long relationship changed forever. It wasn’t worth it, and it usually never is.

I eventually learned to hire people based on their skill, not whom I knew, but the sting of damage remains.

In the same boat? You have a question you need to ask yourself. Emotions are obviously ringing hot, but you now have a choice to make: do you want to maintain the social relationship?

If so, you have to get over it in any way you see fit. End the business arrangement early with no hard feelings. Adjust your expectations for their level of work. Complete the job as soon as possible to get back to your platonic routine with that person. And forget about your experience in the office.

And learn this lesson for the next time: when people are involved in business with you — especially friends or family — they can’t be your friends anymore. You’ll only be setting yourself up for problems down the line if you let business relationships blur into friendships. So do yourself a favor and end things as quickly as possible, wish them luck in their future business endeavors, and move on. Accept the lesson learned.

And be more careful mixing the two again.

Hear about my journey experience on: Business Vibrations Podcast: Seven Minutes of Morning Inspiration for the Creative Entrepreneur