Friends With(out) Benefits: Mixing Business With Pleasure Working with friends, working for friends, and working as a favor to a friend can come with pitfalls, difficulties, huge arguments, and even tears.

It is often said that friends are the family we choose for ourselves. And while that may apply to nearly every aspect of our lives, with friends providing support, laughter, and unconditional love, the ties that bind friends together can become strained, and sometimes break, when confronted to something we're all eventually called on to do: work. It might seem a good idea at first, working with our friends– we imagine the complicity, the fun, the sweet life we will lead if we ever hit it big. But reality is not as utopian as the images our imagination comes up with at the start of such a venture, and while some friends make amazing business partners, and go on to make millions that they spend together as best friends forever, it is not always the case. Working with friends, working for friends, and working as a favor to a friend can come with pitfalls, difficulties, huge arguments, and even tears. Let's talk about mixing business and pleasure.

Friend or foe

When you and your friend both get accepted to work in the same place, it starts off magnificently. Commuting together! Lunch breaks together! Meshing ideas together! Fight for one promotion, together! Competitiveness has proven efficient in stimulating creativity and pushing people to work harder for their goal, but sometimes working at the same company (or even in the same field) as a person you once considered closer than a sibling can place a strain on your friendship as you compete to one-up each other. Friendships moved to the workplace can suffer from passive-aggressive moves, boredom of seeing each other in every facet of your lives, and the destruction of your relationship as one of you tramples the other to get a project, a promotion, and a better deal.

Top-to-bottom approach

When your friend is starting a business or launching a new endeavor as part of an existing company, it is tempting to agree to working as an employee under their direction. You think you'll be familiar with the way the boss thinks, you won't have to suffer through the anxiety of making a good impression, and you'll bring the positive elements of your friendship to work to enhance the entire experience. But things risk going sour when you call out the boss on something as a friend, but in front of other employees. It goes sour when the boss doesn't treat you as well as your colleagues for fear of nepotism accusations. It goes sour when something at work affects your personal relationship, and you start arguing about it during a common friend's dinner. And it goes sour if the venture fails, and you're stuck with your disgruntled friend-slash-former-employer-slash-former-employee (who might even still owe each other money and apologies).

Do me a solid

"I don't know how to say this…" is a common phrase you'll hear when a friend or a colleague in the same field as you calls to ask for a favor. You see, they took on too many projects and can't complete them all, so they need you to help them out. The only thing is, it's for a friend of theirs. Working as a favor for a friend can lead to new business contacts and broaden your horizons, but it can also embitter your friendship when you have to work for a lower rate. Your friend agreed to it, and later it gets tough when you have to tell your friend to ask their friend to please pay you because it's been a year, and your friend starts making excuses for their friend or calls you impatient. It gets weird when you slip up and whine to your friend about how demanding, ridiculous, and cheap your new client is, and they take to defending their other friend and chastising you.

I'm not saying that working with friends is a complete disaster every single time. I'm not saying that you can never work for a friend, and that favors for friends are categorically terrible ideas. I'm just saying that the benefits of friendship can sometimes disappear when work is involved, and that, sometimes, your friends and your work life should not mesh. In any case, if friends are like your family, think about this: would you really want to work for your crazy great uncle or bring your impossible, whiny cousin to work with you? No, you wouldn't.