"We're Both Freelancers”: How Self-Employed Couples Make it Work

My husband and I have never been freelance at the same time but we’ve both suffered and supported each other’s dreams multiple times during our marriage. There’s the good (“You’re following your dreams!”), the bad (“If you’re going to be home all day, can you at least do the laundry?”) and the very ugly (“please tell me that you put aside the money for taxes”).

There is so much to celebrate about freelance life. There’s flexible hours, the chance to choose your projects, and if you’ve got a wise accountant, you can write off that ergonomic chair. The same goes for those brave enough to start their own businesses. Is there anything more exciting than having a vision and pushing it through to reality?

There are also headaches and perils that come with living life in the self-employed or freelance lane, even if you're a dual income household. All the things that are plusses for some freelancers (example: no boss ordering them to be at a desk at 9am) are challenging for others. Structure, keeping on top of finances, taxes (yikes), and hunting for new business and getting paid on time, well, it’s not always so easy.

If both members of a couple are freelance or self-employed, it can double the freedom or double the anxiety. There’s no handbook for freelance couples, so most have to figure it out on their own.

We spoke to four freelance and self-employed couples about what they’ve learned, how they cope with difficulties, and how they celebrate victories.

You both need to take some (work) space

Lindsey Evans and Andrew Lindaas of Walnut Grove, Calif., aren’t just life partners, they’re also business partners. In 2019, Evans, 30, and Lindaas, 33, decided to quit their 9-5pm jobs and start their own lifestyle podcast network together. For them it’s been rewarding being able to pick and choose who they want to work with and how much work to take on.

They credit making designated workspaces for working together and separately for keeping their sanity in check.

They recommend making sure you and your partner have designated office spaces whether that be in your home, an office, or a co-working space.

“Working together from home and living together can be a struggle. Being around someone 24/7 and having to switch from personal mode to business mode isn't always easy,” said Evans. “We spend at least 2 hours a day working in separate rooms and have desks set up in three different rooms in our house so we have mutual workspace, as well as, shared work space.”

“It's hard to be productive from the bed or couch."

Lindsey's top tip: Start creating a nest egg as you start to earn money. “We've been putting at least 30% of our income into savings every month so if business does decrease we have time to figure out a plan B,” said Evans.

There’s no such thing as too much communication

Caitlin Kelly, a writer, editor, and coach, and her husband Jose Lopez, an archivist, photographer and photo editor, have owned and operated their own businesses since 2006 and 2015, respectively.

The couple, who is based in the suburbs of New York City, credit extreme communication for keeping their 20-year marriage on track through all of life’s many crises.

“We're much more candid about our finances and what shape they're in than when he had a good staff job, steady paycheck, paid sick, vacation days, and affordable health insurance,” said Caitlin.

They have monthly "financial summits" to discuss their finances in detail. On the agenda: What they’re each bringing in, what they owe, what they need to focus on. Knowing their assets and liabilities; that alone is a stress reliever.

“We talk a lot!” said Caitlin. “It really helps to have each other's back in every way and to be able to talk things through. Companionship, especially with COVID cutting out almost all social life, is essential. We give each other good ideas for our respective businesses.”

Another communication tip from the couple is to know when, well, not to communicate -- especially when space is at a premium. Caitlin and her husband work in a one-bedroom apartment with no dedicated office space.

“Be extremely respectful of your partner's time, space, privacy and need for their own downtime alone. We always ask "Can I talk to you?" before starting a conversation,” said Caitlin. “I can't see his desk nor can he see mine, so we're as careful with one another as we would be with co-workers in a shared office setting.”

Caitlin's top tip: Appreciate each other for the skills you don’t have. “It's made us much closer because we see how hard we each work and the specific skills each of us brings, and they are quite different. He's very, very skilled at quickly joining any team and fitting in. Me, less so. I'm a more aggressive marketer and negotiator.”

Have confidence in each other

Freelance life can have a lot to do with serendipity vs. planning to go at it alone. For example, Madeline C., a 32-year old executive based in Baltimore, a furlough from her job as a marketer for a craft beer company, became an opportunity to partner up with another entrepreneur's PR business. Her husband Chris, a 33 year-old sales executive, is transitioning to self-employment in January 2021.

The Caldwells began their journey to self-employment by sitting down with a financial advisor.

“Our advisor helped us understand whether one of our incomes could cover our daily expenses, and project how much money we should have in the bank as a cushion while the other starts rolling,” said Madeline.

For the Caldwells, it comes down to confidence in oneself and in one’s partner that you can figure out how to make it work, both separately and together.

“We have proven in life that we know how to make money. Whether it's waiting tables, or rolling in millions, we will be able to provide for our family,” said Madeline. “And if we go down a path that isn't working, we'll shift gears.”

Couples who are freelance have to take leaps of faith, which isn’t always for the faint of heart.

“One of the toughest parts so far has been moving our respective dreams forward without knowing exactly where (or when) the other will land,” she said, “We have two little kids and are adopting a third, so matching up our respective salaries to what we earned with our corporate jobs--and the timing of it all-- has been an adventure.”

Madeline’s top tip: “ You don't need to take all of the advice from everyone. Filter it with your lens, and pick and choose what to implement (or to avoid). Then, always find a way to return the favor.”

It has to be an equal partnership (no, really)

Leela Corman, 48, and her partner Tom Hart, 50, are both Providence-based artists. Corman transitioned from “permalance” to freelance cartoonist and illustrator in 2004. Hart is the executive director of The Sequential Artists Workshopa non-profit art school.

Corman said that before COVID-19, the biggest struggle of being a freelance artist married to another freelance artist was the endless back and forth of “are we making enough money and are we contributing enough.”

Freelance work means waiting for others to get around to paying you. That can be a major disruption to planning household expenses. In order to cope with his, Hart made the decision to change the way he pays himself from his business.

"This was the main reason I converted my income to salary from portion of proceeds, to have some stability, however small," he said.

Now there’s all of the above, plus having their child home with them all the time. Recently, Corman has looked back on her years of juggling family, career ambitions, and finance with clearer eyes.

“I would say that the biggest struggle with being a freelancer, the one that has taken years for me to even see, has been the gender and income inequality,” said Corman. “I had babies and it had a massive impact on my career that it just did not have on my male partner.

“We had our first child in 2009 during that recession, so my illustration work was already dropping off a bit," she said. "But once I had a baby, I was out of the market. It took years for me to begin to get any illustration work at all.”

When both members of couple are freelance, money and careers comes down to a lot more than just paying the bills together. There’s a lot of categorical unfairness in how life turns out and often, women find their careers taking the backseat in order to deal with child care.

“The only thing that's helped us is being extremely categorical about money. We started having regular meetings about finances, at least every month, and more often when we can, and talking about every expense and every gig,” said Corman. “We also had to get very categorical about our bank accounts - having a joint account and each of us having our own independent one, and clearly delineating which expenses come from which account. This has been very helpful in dispelling a lot of foggy and vague-ery stuff around money.”

Hart recommends talking about money early and often, "even when you don't know what you are talking about yet."

"If you feel dumb about, let the feeling dumb allow you to find answers you need," he said.

Leela's top tip: Corman urges freelance couples (and all couples, frankly) to think not only about how they treat each other but how the world treats them differently.

“You may be equals in one another's eyes, but you aren't in the world outside your home,” she said. “Gender inequality will eventually seep into your carefully constructed home and undermine your most intimate relationships. Be ready to understand it together, so that you can at least try to keep it outside of your household.”