Unconventional Productivity: Do Business With Friends

The productivity strategy of Jessica Holsey, the entrepreneur

This post was selected for inclusion in our Future of Art and Work series in December 2016. The series, sponsored by Microsoft Surface, selects some of our best posts exploring the topics of how art and work will look in the 21st century. This post was originally published in January, 2016.

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After three years working on Wall Street, I was twenty-five and starting to feel restless. The problem was what to do about it. So when I randomly met a stranger named Emily Doubilet at a party, and she casually told me about the business she was planning on starting, things started to come into focus.

Emily was calling her business Sustainable Party, and it was all about giving people tips, resources, and all the material goods necessary to host parties without breaking the world. I was like, tell me more.

I like parties—a lot—and I was pretty sure I liked sustainability. Most of all, I liked Emily’s obvious passion for what she was doing. It was contagious. After I started to learn more from her about the world of plant-based and sustainably-sourced materials, I quit my job so that the two of us could embark together on a quest to make parties more sustainable, and sustainability more fun. We launched the Susty Party line of disposable party tableware in May 2012, and since then have even expanded beyond party products: we just launched our home collection this past month.

At first, my relationship with Emily was sort of hard to figure out. We were business partners who had met by circumstance at a party, and while we were friendly, we were really different from each other too. Like, really different. I was a former college athlete, economics graduate, and Wall Street refugee who lived on the Upper East Side. Emily was an environmental studies grad who hosted burlesque shows and was a member of an electro-pop music duo. And the two of us were working together out of a tiny, shared office space. Basically, it was the Odd Couple meets Girls, but instead of living together we were trying to run a business.

I’ll admit, there were moments when I worried. But we got lucky. Whether despite or because of our differences, Emily and I quickly became friends.

The problem turned out to be the opposite of what I had worried about: as our friendship developed, it became harder to focus on the reasons we were supposedly there in the first place.

Our important “lunch meetings” began to run long while we gabbed, and longer when we decided to cap them off with a trip to check out that new store around the corner. Soon, it dawned on both of us that if we wanted to be successful, we had to learn how to find the right balance between work and play to maximize our productivity, without sacrificing all enjoyment. After all, one of the reasons I’d left Wall Street in the first place was because I wanted more freedom. And we were a company that made party supplies. Shouldn’t fun be part of our business plan?

One obvious solution would have been compartmentalizing our relationship: vowing to focus on work while at the office and save the socializing for when the workday was over. But this approach can get complicated fast. When you’re sitting two feet away from each other all day long, it becomes overwhelming and difficult to make rules about the different ways you’re allowed to interact with each other, and it can lead to misunderstanding. On top of that, I think both of us knew that, for entrepreneurs, socializing can be productive. Some of the best ideas happen when you’re just chillin’.

After a little bit of trial and error (and some days where we found that we were spending way too much time chatting) Emily and I found the approach that works best for us: we started making an effort to incorporate fun, social activities into our work schedule. Call it structured socializing. It allows us to focus while at the office, but also have some fun activities to work towards throughout the day.

For instance, in the summer we always try to set aside a few days to work by the pool. One of our very first business planning sessions happened while we were lying by the pool at the West Hollywood Standard wearing bikinis. Say what you want, but it was super-productive.

We also plan weekday trips to go camping, and to surf together on some mornings before work starts. In the winter, a good ski trip is always welcome getaway. We also make sure to do fun things in the office—we’re particular fans of “90s Flava Filled Dance Aerobix Workouts” with Viva Bodyroll.

Carving out time from the workday and designating it towards activities we enjoy helps us focus on work, while still knowing that there will be some time to take a break and have fun with each other when the time is right. It doesn’t just keep us on task, but has taught us how to use our friendship to increase our productivity. Mixing work and play into something that kept us even more focused on the tasks at hand, and more creative in our approach to our entrepreneurship.

Contestants on reality shows are always saying they’re “not here to make friends.” Whatever. When you actually like the person you work with, you work better.

Unconventional Productivity is a five-part series of stories written by creative professionals about their best rule-breaking advice.

Jessica Holsey the co-founder of Susty Party.