Working with Your Spouse: How We Got Started and How to Keep Going


I was sitting in Star of Siam, a small restaurant a few blocks away from the Chicago Tribune, sipping a Singha and reading a new eBook on my phone while trying to catch stray Pad Thai noodles with my chopsticks. The book was the Unconventional Guide to Freelance Writing, and I’d just paid $50 for it, hoping it would unveil the secrets of the universe. I’d been working as a writer for years, writing online content for peanuts and struggling as an aspiring playwright and novelist. It wasn’t going anywhere, so I ended up at Tribune Publishing, writing print advertising and classifieds for chihuahua puppies in Orlando, cemetery plots in Baltimore, and every god damn yard sale in Allentown, Pennsylvania. 

I was desperate to get out, run like hell from the 10th floor, and finally escape “The Tower.” But I had been writing a play for the past two years, and pouring every penny I had into producing it at The Den Theatre in Wicker Park. The best collection of storefront theatre performances in Chicago happen at The Den, and I’d been there for years, taking classes and talking shit at the bar. The place was home, in a sense, and I just had to bring my play there - but that took money. 

So, there I was with this eBook, it’s tan background grinning at me from my iPhone, “You really want to go back to writing for a living?” 

A part of me didn’t want to. I was finally getting a minuscule sliver of respect from family and friends back home in Louisiana. At least they’d heard of the Chicago Tribune! That name had weight, promise, and significance in their minds. They’d never heard of The Den, or any other writing or performance venue for that matter. Plus, I finally had a steady paycheck. I was able to go to the store and buy brie and wine and pork tenderloin. I didn’t want to give that up, not to go back to writing articles for $15 a pop, trying desperately to keep everything afloat while performing and working with theaters for free - running all of their marketing campaigns and building their websites in exchange for stage time, help, or notes.

But this eBook was telling me that I could be a copywriter, something I’d never really thought about. I’d seen Mad Men off and on, but I never really got into it. I didn’t know anything about Leo Burnett or David Ogilvy for that matter. But for whatever reason, I decided to go for it, and I brought my main squeeze with me. 

John had been working at the Tribune for a few years before I arrived, toggling between display advertising and working as an account executive for the paper’s real estate division. His cubicle overlooked mine, and slowly we built a friendship which eventually turned into a promising relationship. Together, over cold mugs of Schlitz and hot double stack burgers at the Billy Goat Tavern, we plotted our escape. 

The day we finally left the Tribune was June 1st - Marilyn Monroe’s birthday. I would know because I’d just closed my solo show detailing her life. I’d quit my job roughly six weeks before (long story), but John was finally quitting the Tribune, once and for all. I was still in full makeup, waiting in the lobby, shooting the shit with the woman working at reception as John went upstairs, cleaned out his desk, and left his key card on the table. We skipped down Michigan Avenue beneath the lights in the trees - finally free from those constantly ringing phones and the smell of panic that had invaded daily life at the struggling newspaper. We were ecstatic, drunk with anticipation, and unsure of what the future might bring. 

To think that was almost four years ago… 

Crazy how time flies! 

John and I have been working together ever since, collaborating with some of the best software development companies in California, the most dedicated non-profits in Chicago, and some of the most inspiring artist entrepreneurs and small business owners working online today. It is truly insane how far we’ve come from that day at Tribune Tower, rushing through the door as two newly-freed creatives. But working with your spouse isn’t always easy. And after nearly four years of working together 24/7 on every project, piece of writing, and bit of strategy, here would be our advice to you other couples looking to work together:

1. Play to each other’s strengths. 

I’ve been writing for alot longer than John has; but he’s been in sales for a hell of a lot longer than me. I was building websites as soon as template sites became a thing; whereas John never even had a website to manage before we started our business. John always found himself in collaborative environments as a professional drummer; whereas I had always worked in competitive environments where only one could win. I was raised in a damn near militaristic family; John was raised in a much more chill environment. John is great with numbers and mechanics; I shine with abstract concepts and themes. In so many ways, we are two sides to the same coin, and we’ve struggled in finding balance. But if you are starting a business with your significant other, make a list of your strengths and weaknesses, individually and as a couple. Use that as your guide for determining who is in charge of what, and how you can best work together to move your business forward. 

2. Find balance between pushing and nurturing. 

When I look back on my days working solo, it’s easy to fantasize about being responsible for only myself and the work. My living expenses were lower, my schedule was different, and there was no one to blame but myself if something went wrong. However, even back then, I was spending more time at the theatre than working on my content - and it probably showed. But part of the beauty of working with a spouse is that you can share some of the responsibilities, while also having an accountability partner for quality control. Even then, it’s hard to find that line between pushing too hard, having unrealistic expectations, and maintaining a healthy relationship, especially when you’re just starting or still figuring out how to build your wings on the way down. And it’s really easy to point fingers or blame your partner when things don’t go as expected, but as partners, both of you are responsible for everything that leaves your desk, office, or computer. And at least in our experience, yes, you have to push each other, but you also need to be a friend and ally when things don’t work out according to plan. Remember: you’re in this together. 

3. Listen to each other and respect boundaries.  

When you’re working alone, you don’t really have to listen to anyone outside of customer feedback. You’re figuring it out on your own, so there’s no one to really talk to or teach. When you’re working with your spouse or partner, it’s a very different situation. Each of you are constantly taking in information, filtering it through your personal experiences, and applying it to your joint efforts in different ways. For that, you absolutely must have open communication and empathy for the other person's point of view. More importantly, you must respect the other’s boundaries. No two human beings are exactly the same. Everyone has limitations in some way or another, whether they’re physical, mental, emotional, or intellectual. For instance, I’m never going to be great at math. It’s just not in the cards for me. On the other hand, John will probably never be a fan of social media (he’s never even had a Facebook account, which, looking back, was probably a very wise decision). The trick is to understand each other’s limitations, truly listen to your partner’s reasons for why they don’t want to do a specific task or have a certain role, and respect their boundaries. You can always find a compromise if you try. 

4. Teach each other. 

I love to learn. In fact, knowledge is probably my favorite asset and I’m borderline obsessed with acquiring it. Incidentally, so is John. But we’re interested in different areas of knowledge. For me, ancient civilizations, philosophy, tech & morality, history, business strategy, case studies - I love them enough to roll in them like a dog in freshly cut grass. John, on the other hand, is more interested in music, ensemble, sales, people, pop culture and the like. The beauty of our differences, however, is that we can both teach each other about our passions, and this extends to our business. For example, if I’m writing an article about cryptocurrencies, we might learn different things about it and teach each other. If John is heading up a project for a nonprofit, he might learn everything about it, then communicate that knowledge to me. That way we’re always on the same page, and able to critique each other’s work in the best interest of the client, publication, or whatnot. It’s a team effort, right down to what we learn and understand as a partnership. 

5. Remember to have fun. 

It can’t be work-work-work all the time. You’ve got to find balance and have fun too! We do this by cooking together, watching standup specials, quoting our favorite comedies in jest, and maintaining a long list of inside jokes that no one else could possibly understand. In a sense, we’ve developed our own language of references, and that’s part of what makes working together great. We’re with each other far more frequently than we are with anyone else, and if it wasn’t fun, it wouldn’t work. And there will be days when it’s dark and gloomy, a client is asking for xyz, and you’re struggling to keep your wits about you. When that happens, laughter truly is the best medicine. So have fun, enjoy each other’s company, and keep happily trudging along. That’s why you went into business together in the first place, right? 

-Written by Amber; John approved.