The Tricky Business of Mixing Friendship with Work

Starting a business with your friends sounds great on paper, doesn’t it? You trust each other, you get along, and you think alike—what could go wrong? As someone who’s been down this road, let me take you through what it’s really like to mix friendship and business, because it’s not always the smooth sailing you’d expect. 

First off, starting out with friends is pretty fantastic because of the trust factor. You’ve got each other’s backs, making those early uncertain days a bit less daunting. Decisions feel easier because you’re all on the same page, right? This was a huge plus in my experience. It’s like having a built-in support system from the get-go. 

But here’s the thing—when you’re in a business with friends, lines can get blurry. Mixing friendship and work means you might avoid the tough conversations for fear of rocking the boat. I learned this the hard way. It’s tough to tell a friend they’re slacking on their responsibilities or that their latest idea isn’t as brilliant as they think. You want to keep the peace. But sometimes, keeping the peace means you’re not making the best decisions for the business. 

Then there’s the whole issue of expectations. Everyone comes into the business with their own ideas about what they’re going to do and how things should run. When these expectations don’t line up, things can get messy, and because you’re friends, it feels personal. We had a few rough patches where misaligned expectations led to real tension, and it was more painful because these weren’t just colleagues—they were my friends. 

One of the biggest wake-up calls for me was realizing just how much of our friendship we were gambling. If the business failed, would our friendship go down with it? That thought kept me up at night more than any business problem did. 

So, what’s my take on all this? If you’re going into business with friends, treat it with the professionalism of any major business venture. Set clear boundaries and expectations right from the start. Have the hard conversations about roles and responsibilities. Don’t let problems fester because you’re afraid of a little conflict. 

And communication—this is non-negotiable. Be honest and upfront with each other. When issues come up, address them head-on. Conflict is part of any business, and how you handle it can make or break both your business and your friendship. 

Most importantly, remember why you started. You need to preserve that friendship because it’s precious. Sometimes, that might mean making tough choices for the good of the relationship. Don’t be afraid to redefine roles or even step back if it means saving the friendship. 

Mixing business with friendship is definitely a ride. It’s challenging and risky, but also rewarding in ways I never expected. My advice? Go in with your eyes wide open, communicate like your business depends on it (because it does!), and whatever happens, look out for each other.