March 20, 2019

Working With Loved Ones

In direct violation of accepted wisdom, I’ve found myself in business with both my best friend, and my partner. It’s been five years, and we haven’t killed each other or ruined our friendships yet.

Today, I don’t look back on the decision to go down this path with anything approaching regret or doubt. If anything, I feel relief at not having missed out on the most positive, fulfilling five years of work in my life.

Still, there are good reasons to be wary of mixing work and personal lives in this way. It’s a volatile mixture, but one that can be successfully integrated given a bit of wisdom, a lot of patience, and strong underlying relationships.

Shannon, my partner, suggested we each write about what this experience has been like, and you should go read her piece. For my part, I struggled to figure out what I wanted to write about the subject. It’s not some oddity that I feel the need to justify, nor some elaborate effort that I can unpack…it’s just my life.

Find the People You’re Okay Doing Anything With

Ironically, that train of thought led me to my first realization: work shouldn’t feel like something alien, it should be just another thing you do together.

I’m coming to understand that when I have a true compatibility with someone—romantic or platonic—there isn’t really a set of boundaries around what activities I enjoy doing with them. I don’t have many friends, but the ones that I do have are the kind of people I would be happy to spend time with doing just about anything—even work!

Friendship is the Core, Work is a Layer

Whenever I think about it, I keep coming back to the idea that everything is built on top of the friendship. Adding work to the equation shouldn’t replace the friendship dynamic, it has to be built on top of it. That way, if things don’t work out, you can remove that layer without harming what’s underneath.

Easier said than done, of course.

One thing that took us some time to get right was the need to segregate fun and work time so that we weren’t always talking shop outside of work. When you not only work with friends but also enjoy what you do, the temptation to dwell heavily on work talk is high.

This has some negative consequences beyond the obvious. I noticed that our friend group was affected by it too. It became daunting for others in the group, harder to feel close” to us, since the three of us had the impossible advantage of spending so much time together. This can put unwanted distance between you and your other friends, and it’s something that can only be mitigated by sticking to the rule of not talking about work when we’re out with others.

Wearing Different Hats

Layering comes with its own problems though, one of which is that the underlying friendship changes the dynamics of difficult business conversations. If there’s a dispute or disagreement, it can take longer to resolve because each person is thinking not only about the business implications but also the personal ones—we don’t want to hurt each other’s feelings.

What works for us is making sure to bring up points of discomfort as early as possible, before they fester into something more toxic than a small doubt. The sooner we talk about it, the less damaging it is. Over time, we’ve also come to understand each other well enough to pre-empt certain disagreements and navigate around them before they even come up.

Ultimately though, some conversations have to happen with our business partner hats on and not our friend hats.

Tools of the Trade

On a practical level, there are a few small things I want to highlight.

The first is Basecamp, our project management solution of choice. The specific tool isn’t relevant, only that we use something that allows us to explicitly segregate work conversation from personal conversation. Work stays in Basecamp, so we aren’t always tempted to pick up a work-related thread whenever we open iMessage.

Another important practical item is the use of certain signals to help each of us do our best work. These can be simple things like wearing headphones to indicate a flow state, and making sure the workplace is arranged in a way that facilitates independent, focused work.

Working With Friends

The risks are well established, and the first little while can be difficult while you find your footing, but I absolutely love working with my friends.

The knowledge that my coworkers actually care about me as a human being encourages more open sharing of ideas and fosters a happier workplace mood. And the time we save through simple fact of our shared shorthand communication is a large part of why we can be so nimble as an agency.

I’m grateful to be able to say that I work with my best friends every day.


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