Do It Jointly

What Happens When Both Partners Own Their Own Businesses?

CJ enjoyed being self-employed so much that he inspired Joslyn to start her own business. But they had to figure out how to make it happen without rocking the family finances.

A few weeks ago, Jointly talked to Lillie and Wayne—married engineers, with an unusual budgeting arrangement. Both partners switch between working day jobs and paying bills for the entire household and being financially supported while taking time to pursue their passion projects—dancing for Lillie and traveling for Wayne.

This time, we talked to two partners who both dreamed of working for themselves but had to figure out how to make it happen in a way that worked for the family income. Ultimately, each partner financially supported the other while s/he built a business.

Here’s their story.

The Therapist and the Designer

Who: Joslyn & CJ
Where:  Chicago
Relationship: Married
Children: Vivian, 9

With a freshly-minted Masters in Social Work, Joslyn got her first “adult” job in the psychiatry ward of a tough county hospital in 1998. (Ever watch the show ER? It’s based on her hospital!) It was a great job—five weeks of vacation, good insurance, a pension, and union benefits. But with her two-hour round-trip commute, Joslyn was “at work” 10 hours a day.

“I thought I had to be wed to a boss and someone who okayed when I took vacations. I never thought I could do something as amazing as what I’m doing now.”

Around the same time, CJ graduated with an environmental science degree and worked odd jobs while he taught himself to code. Later he began coding 70-80 hours a week for start-ups and discovered that his favorite part of the gig was web development. In 2006, he and Joslyn married.

Three years later, he decided to leave the corporate world and work for himself, doing only web development. When he broke the news to Joslyn, she was four months pregnant and stunned.

In her mind, the announcement had come out of nowhere, and it totally freaked her out. “I was so worried about him not having insurance, not having vacation time, but he said, ‘this is what will make me happy,’” she says.

CJ didn’t want to work overtime as a new father. Because she trusts him, Joselyn agreed, but with a caveat. “If you can’t make this work in a few years, you’re going back to corporate America,” she told him.

Deep down, Joslyn suspected it would work. “My husband isn’t risk averse, but he’s also not dumb. When he decides to execute a plan, he goes all in,” she says. (Like how one day, he suddenly started competing in triathlons. And then there was that time he taught himself to code.)

The first year was tough. CJ wasn’t contributing to the family income, and Joslyn was jealous that he got to stay at home with the baby while doing work he loved. But by the second year, CJ had clients, and by the third year, he was making 75% of his previous income.

“That’s when I began just playing with the idea of quitting and doing my own thing, too,” Joslyn says.

Even before she got pregnant, she saw a few private practice clients on weekends. She knew she’d prefer to work for herself, but she also knew her position was enviable. She was steadily climbing the ranks at a public hospital where, eventually, she’d become the Clinical Director of Psychiatry.

But when their daughter, Vivian, started preschool, CJ’s web development company, JellyNeck Solutions, was going strong, and Joslyn began to resent not being around for field trips and class recitals. She didn’t want her daughter to ask, a decade later, “Mom, why didn’t you leave the hospital?” She didn’t want to have to reply, “I was scared.”

CJ was only slightly sympathetic. He kept telling Joslyn, “If this is painful, do something else.”

By the time Vivian finished preschool, Joslyn had an office picked out for a private practice and the paperwork was done. But she was nervous about leaving. If she put in a few more years, her pension would get a big boost, and she liked the dependability of a steady paycheck.

Her financial role models—her parents—had held the same positions, at the same institutions, their entire lives. Her father was a professor and her mother was a medical technician. She was raised on stability.

But Joslyn was tired of triaging patients in crisis. “My passion was to build a therapy practice where I could see people really get better,” she says. So she quit the hospital. She had been there 16 years.

CJ was Joslyn’s biggest cheerleader. He knew he would be the primary breadwinner for awhile, just as Joslyn had been, but he was grateful for the opportunity to pay her back.

A month after she launched her practice, Chicago Human Potential, Joslyn had patients. It took two years for her to match her hospital salary, but by the third year, she was making more than she’d ever made before.

“I never thought I could do something as amazing as what I’m doing now,” she says. “I thought I had to be wed to a boss and someone who okayed when I took vacations. Now I can take my daughter to school when I want, I can go on field trips, I can work nights if that’s better, and my husband is at home doing his website business.”

Joslyn is five years in, and CJ is nine years in. Personally and as a family, things just feel more balanced. Joselyn has five employees, and she recently purchased a health plan for her business, which gives her better coverage at a lower cost than the private insurance she was buying. She is one of six private practice social workers in Illinois who accept the state’s Medicaid, so she’s able to keep her social justice mission alive.

CJ and Joslyn don’t fight about money, but they talk about it casually and often. They have a joint account, as well as separate personal accounts. They’ll discuss investments over dinner, and once a year they meet with a financial advisor. They stash a percentage of their income for retirement, and except for mortgages, try to stay debt-free.

Joslyn stresses about money, but CJ rarely does. Recently, she was worried about an unexpected expense, and CJ asked, “Why do you feel like the direction our finances are going always falls on your shoulders? Every time something comes up, you feel like you’re responsible for steering the ship.”

He’s more comfortable with less stability. When he was a kid, his parents lost a family farm, but his mother went back to school and got a Master’s degree, and they rebuilt their finances.

“My husband could kind of see that you figure things out and make it work. I had this philosophy that no, you had to be hunkered down, earning money,” Joslyn says.

She’s reactive and he’s logical, and because of that, they balance each other, financially and otherwise.

“When we got married I never would have envisioned this. But recently, I did find an essay I’d written in 7th grade, that said ‘I want to be a psychologist, and I want to have my own office.’ So in a way, I’ve come full circle and fulfilled my childhood dream,” she says.

Photo by Julia Franzosa