Articles - 13th February 2019

Life as a Freelance Couple

Words by Hilary Oliver
Illustration by Darren Shaddick

Kicking my slippers off my feet and pulling the covers up in bed, I press play on a jazz playlist on my phone, which sits on the nightstand. The sound is to cover the pat-pat-pat-pat of Brendan’s typing on his laptop out at the kitchen table. It’s 10 pm, and he’s wrapping up a few emails while I try to wind down for bed. But that sound—the click of the laptop’s keys—triggers thoughts about all the things I have to do tomorrow, and next week and the week after. Both Brendan and I are freelance writers, and we love the flexibility our jobs allow. But with that beautiful flexibility comes a different kind of responsibility and a host of potential complications to our relationship.

When Brendan and I met, I’d been laid off from a magazine job and had given up on the freelance life. Bills kept piling up while I tried to pitch freelance magazine stories, and I didn’t build my workload fast enough. So, I wound up waiting tables and then assisting at a law office. When Brendan and I were going on our first dates, he was giving his notice to quit a job as a remote copywriter in order to pursue his own freelance writing full-time. I plied him with questions. Why did you start writing for the web instead of magazines? Do you get paid enough? How do you pitch stories and find work? He helped guide me back into the writing world, and I began writing and pitching on evenings and weekends.

Brendan was living out of a van at the time. He’d hit the road after a breakup a couple of years before, and since he was writing mostly about rock climbing and outdoor adventure, it worked perfectly for him. He’d drive from one outdoor hub to another, working in coffee shops and sleeping at campgrounds or trailheads. Six months after we met, I moved out of my apartment and into the van with him. It was one of the biggest gifts he’s ever given me: the chance to live a low-overhead life whilst I scrambled to start up my freelance writing and editing career.

At first, I made barely enough money to pay my credit card bills. But the freedom, for me, was intoxicating.

We drove all over the West, from the Grand Canyon to the California coast. And slowly I built up my career, making contacts, pitching stories and holding down an ongoing editing contract.

I look back so fondly at that time in our relationship. But now, more than six years later, I realize that what felt like a magical time of adventure and opportunity, had been incredibly stressful for Brendan because he felt responsible for me. He had taken me under his wing while his own fledgeling freelance career was just taking off, and he worried each month about whether or not we’d have the money to eat, to put gas in the van and to pay for health insurance.

Being two freelancers trying to make a life together felt like trying to cross a wide, rushing stream on separate footbridges. Each footbridge felt rickety, and were maybe even missing some boards—it took big steps and a little risk to keep moving forward. And it always felt like there was a chance one of the boards might fail, sending one of us crashing through. The beauty was that we could reach out to one another—as long as the other was steady enough to hold us for a minute while we climbed back up.

Sometimes one of us reminisces about when we had a full-time job—how secure that could feel, as opposed to swinging from one gig to the next or trying to keep several irons in the fire at once. But the sting of my layoff in 2008 still lingers in my memory, and the idea of diversifying our income streams actually feels less risky now than depending on a single employer for everything.

Keeping those diverse income streams flowing requires constant effort—which adds a different kind of challenge to our relationship. When neither of us has specific office hours—no 9 to 5, no clocking in or out—work can seep and spread into each minute of the day, if we let it. The beauty of our flexibility is that we can take off midday for a trail run if we want. Or, work remotely while travelling in another country. But the work still needs to get done—and sometimes that means laptops at the kitchen table over dinner, or typing away late into the night. And that’s when things can get overwhelming.

Each couple is unique, and things that work for us might be disastrous to others. I wish I could say our life is 100 percent dreamy—but I’d be lying. Because there are certainly days when the workload feels like it’s threatening to squash me, or days when I worry the jobs will dry up. And days when I wish Brendan wasn’t so busy, because one thing I’m working on is not taking on other people’s stress. I can feel, in my stomach and my limbs, when Brendan is worried about something. And me worrying too, without doing anything to help, isn’t going to benefit anybody.

But over the years, we’ve figured out how to keep things humming along, smoothly for the most part, both in work and our relationship, and last fall we got married. Like the rest of our life together, our wedding ceremony wasn’t super conventional. We picked the traditions that held meaning for us as a couple, but rejected those that didn’t feel true to us. It was simple, but deeply emotional for both of us.

As each of us grows in our work, honing our craft and working with new clients, new challenges will surely sprout up. But I’m so grateful for the unique life we’ve been able to build together, through the work we do and how we spend the free time in between. Here are a few things we’ve learned that we’re hoping will serve us well into the future:

Stay humble, in both work and finances

I know a few couples who choose not to collaborate on projects—which may certainly be a wise choice. But so much of Brendan and my work revolves around shared passions. We’ve occasionally worked together on projects, including a short film released in 2018. We constantly edit each other’s work because each of us values the other’s opinions and skills. But this would never work if we were so in love with our own ideas that we couldn’t bear to feel criticized.

Humility has been a key factor in allowing us to work together and stay friends.

It’s also been crucial for us when making it through tough times financially. For me, accepting Brendan’s help when I was first getting started required me to swallow my pride. And now, each of us cheers on the other as we pitch and accept bigger and better projects and assignments.

Respect each other’s independence

As close as Brendan and I are, it’s been important for us to let each other do our own things and support each other in new opportunities. We are considerate to each other when scheduling our travels and often try to include each other on different trips.

But we also must be comfortable and confident in letting the other travel independently. Whether that’s a week, or a month-long raft trip in the Grand Canyon, or a week-long ski trip in Norway. Sure, it’s difficult to say goodbye, especially if we’re sending the other off on a trip we’d like to go on, too. But we’ve found we’re happiest with a balance of away and together.

Speak up for your needs—and listen to the other’s

I’m a sensitive and generally accommodating person, so it has taken me most of my adult life to learn to listen to my own needs and be able to communicate them. Sometimes it’s the need to say no to social events to protect my alone time, and sometimes it’s the need to put away my work and get outside for a while.

Other times, it’s the need to say no to Brendan when he’s going to do something fun but I have a deadline coming up. I’ve learned that keeping worries and feelings to myself just creates a stress stew inside, and whenever I do communicate my needs, Brendan is supportive. I try to give the same to him.

Make time and space for intimacy and protect it

I wish I could say Brendan and I have some perfect habit or routine for time together outside of work. But in reality, in all six years of freelancing together, our weekly and daily schedules have been all over the place.

Some weeks we do the bare minimum of work and take lots of time for fun—and other times it feels like we’re ships passing in the night, even when we work in the same home office together.

But on the days when we’re super focused on work, we at least shoot to have one sit-down meal together, where our phones are put away and we can simply enjoy each other’s company. Even if that just means giving a “you can do it, I’ve got your back” pep talk while we eat boxed macaroni and cheese. And we don’t let more than a day or two go by without either going for a run or walk together or going out for a meal to catch up.

Always, always support instead of tearing down

If we can’t go to our partner for support and encouragement, who can we go to? Brendan and I depend on one another to be each other’s biggest cheerleader and most consistent sounding board. But if one of us were to shift our attitude from positive and supportive to negative and nit-picky, it would start to rot the foundation we both stand on.

More than anything else, I think, building a strong relationship between two freelancers simply requires believing in each other.

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