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Balancing the Grind with Ben Hughes VP, Creative at Squarespace

Ben Hughes is the VP, Creative at Squarespace, where he oversees the creative team, responsible for all advertising, brand design, social content and integrated production.

1) To kick things off, could you tell us a little about your career background and current role?

I’m the VP, Creative at Squarespace, a website building and ecommerce platform based in New York, where I help lead the team that creates our advertising, brand design and content.

A lot of companies do this kind of work with external partners like ad agencies and design studios, but given how central design and creativity are to our brand, we think it’s important to make as much as we can in-house. 

I got my start as a copywriter at ad agencies, worked my way up to creative director, then took a few left turns into filmmaking, entrepreneurship and tech. Something I love about my current role is that it lets me leverage all of those different experiences on a daily basis. 

2) What does a day in the life look like for you? Can you take us through a recent workday?

I generally wake up around 6:30am (or even 7:00am, if my kids are feeling especially generous), put the coffee on, and peek at my calendar and to do list so I can start mentally dividing up my day.

Now that the weather is starting to get nice again in New York, my family and I will eat breakfast together on our little patio, and then my wife and I start getting the kids ready for school.

That can mean in person or remote, depending on the week, but either way they get settled by around 9:00am and that’s usually when I start working.

There are three major types of work I do: managing people, managing projects and occasionally getting hands-on myself. The people part often means checking in with my creative directors to see how their own projects are going. We troubleshoot problems and make sure everything’s on track.

On the project front, there’s always a variety of assignments at different stages moving through our department. Early on, it’s about setting the project up for success with the right people, goals, timeline and process. In the middle, I’m reviewing creative work and socializing it with counterparts on other teams.

Then we get into the making—whether that means shooting a commercial, building a website, creating social content, expanding our core brand design language, or all of the above. 

Managing creative work is very different from doing creative work, but I’ve never understood how to do one without the other, so I also try to reserve at least a sliver of my time to get my hands dirty. I’ve always worried that if I stopped altogether I would lose the feel for it, and you can’t be a good creative leader without that. 

From my calendar’s point of view, my new normal looks pretty similar to my old normal, but what isn’t captured there is having to jump out of a call to help with schoolwork, or make lunch, or (sigh) break up a fight about whose turn it is to choose the afternoon cartoon show.

That all contributes to making my working hours a bit less productive than they used to be, so I usually have to play some catch-up after the kids are in bed for the night. 

3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?

Pre-COVID, our expectation was five days a week at the office. When the pandemic hit, I really didn’t know how we would get anything done remotely, but I’ve been consistently surprised over the last year at the quantity and quality of work we’ve been able to create from our kitchen tables. That’s a huge credit to the team. 

Post-COVID, I imagine flexible working is something we’ll seriously consider, although there are still a lot of unanswered questions around it. Creative work is incredibly collaborative, which is why we’ve always placed a premium on having everyone together in a room.

Working from home hasn’t been as disruptive as I initially thought, because we just moved everything to digital rooms like Slack, but what happens when some people are live and some are virtual? Do you have to have every conversation twice? Can work only happen in places where you can get part of the team on a Google Meet?

We’re all unwittingly participating in one of the biggest social experiments of all time and we’ll continue to learn as we go.

4) What does work-life balance mean to you and how do you work to achieve that goal?

Work-life balance is a tricky thing for creative people because we’re lucky to have jobs that let us do things we would want to be doing anyway.

I love to write. I love making films. I love solving problems. I love thinking about where technology is taking us. The borders between my work and the rest of my life have always been permeable, which I really enjoy, although I also acknowledge it can lead to unhealthy situations.

I’ve experienced burnout in the past and the only good thing I can say about it is that it’s made me very focused at this stage of my career on creating work environments where everyone can achieve some level of balance.

There’s another reason for that, too, which is that work-life balance makes creative work better. The human brain is an assembly line and your inputs are eventually going to show up in your outputs. To make good work, creatives need the right raw materials from art, films, books, music, relationships and experiences.

That’s what we build new things out of. If all you do is work, the only input you’re going to have available to you is other work, which is a recipe that usually results in something derivative and undercooked. 

To be honest, I have a very hard time turning the work part of my brain off, but I try to compensate for that by making sure I’m always feeding it inputs I wouldn’t encounter on the job.

Today, I read a chapter of a book about fungi (Entangled Life by Merlin Sheldrake — it’s an excellent and eye-opening look at a mostly-invisible kingdom of life that makes our lives on this planet possible), listened to the new Floating Points album with Pharoah Sanders, did some research on where to plant a rose garden for my wife, and helped my kids with an art project.

I also did a bunch of work. It may not be what we classically think of in terms of balance, but it keeps me energized.

5) In the past 12 months, have you started or stopped any routines or habits to change your life?

During the pandemic, my friends and I started having a standing bi-weekly Zoom call to catch up.

It’s not a great experience, to be honest—video calls are somehow even more awkward with people you know well—but it has made me think about the importance of prioritizing friendships.

In your twenties, your friends are your entire world, but as life gets busier it’s easy to drift apart without realizing it. When the world opens back up, I hope we can keep it going IRL and defend that time against all of the other things competing for it. 

6) Do you have any favourite books, podcasts or newsletters that you’d like to recommend?

I love this newsletter called Essential Ephemera that my former co-worker Lauren Epstein writes. It’s a great and very personal mix of, in her words, “content, culture, campaign, technology and trend information—plus, some poetry and weirdness.”

She’s a brand strategist by training and has an incredible knack for connecting the dots between seemingly disparate pieces of information. I always learn something and I always laugh out loud.

7) Are there any products, gadgets or apps that you can’t live without?

I’ve tried every piece of productivity software there is, but always return to this dead simple iOS app called Captio. It only does one thing, but it does it incredibly well: you type a note, hit send, and it emails it directly to your inbox.

From there, I can add it to my to do list (I use Things, but regularly default to TextEdit), file it away in Evernote, or take care of it directly from email. Unlike other apps, where your notes can easily get lost, it forces you to deal with them because they’re in your inbox. 

8) If you could read an interview about work-life balance by anyone, who would that be?  

I’m always interested in how other creative people think about and create balance, especially busy ones at the peak of their careers, so I’ll put in a vote for my favorite living artist, Olafur Eliasson.

9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?

My grandparents owned a dairy farm. They worked seven days a week, from before dawn until after dark. Often, they would have to get up in the middle of the night to take care of a sick animal. They never took personal days and rarely took vacations. There were also some of the happiest people I’ve ever known. 

My grandparents had no work-life balance—they literally lived at their workplace!—but they found their work so meaningful that it didn’t matter. To me, that’s what’s missing from the conversation. We treat our work and our lives as if they’re opposing forces, while meaning offers a way to integrate them. 

It’s impossible to achieve balance when you hate your job, because even in your free time you’re going to dread and resent it. In the US, studies show that over 50% of workers are unhappy at work, and all of the resentment finds an outlet in (among other things) our politics. It’s a crisis. I think if you offered people a choice between working less at their current jobs, or working the same or more at a job they found meaningful, many would choose the latter. 

Finding balance is critically important, but I think we should also be talking about how we can create a world where more people can find meaningful work, and meaning at work. 

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About Author

Balance The Grind gives me a platform to talk to these people about how they're achieving their ideal lifestyle. I'm inspired by the passion, the work ethic, the hustle; and these conversations motivate me to live life the way I want to live it.