Two Entrepreneurs Share Advice on Leaving a Corporate Role and Becoming Self-Employed

UPDATED: April 6, 2023
PUBLISHED: April 6, 2023
self-employed woman working from home office

As a workforce, we’ve spent a great deal of time the last few years reflecting on what we want out of our careers, and how to go about achieving it. After experiencing an unparalleled shift in many corporate jobs from cubicle life to couch adjacent (via the pandemic), some employees realized they wanted to make this work-from-home situation permanent. Many also began considering leaving corporate life altogether and becoming self-employed.

It’s a carefully considered decision, and one that certainly carries risk. However, Stephanie Levinson and Jeff Lerner are shining examples that taking a chance on yourself can pay off.

What to consider before becoming self-employed 

If you’re thinking about pulling the ripcord to become an entrepreneur, here are some tips from them.

Decide if becoming self-employed is really something you want to do.

Communications professional Levinson spent her early career at various companies and agencies. In 2019 she had a child, which changed her perspective.

“I longed to have a job that allowed me the flexibility to spend more time with my daughter, but still scratch my creative itch by working part time,” she says.

During the pandemic, Levinson’s agency went through a restructuring, and her role was eliminated. While she considered finding another agency or in-house communications position, her husband encouraged her to explore striking out on her own and become self-employed.

“He saw firsthand that the last two years had been difficult for me being away from my daughter nine-plus hours a day, and working for myself would give me more freedom to focus on her,” she says. 

For Lerner, the pandemic gave him a renewed focus on family and spending as much quality time together as possible.

“As the world was opening back up and returning to some sense of normal, I questioned the idea of working on someone else’s schedule,” he says. “I didn’t want to travel as much, I wanted to continue to coach both of my kid’s Little League teams, I wanted to help out in their classrooms, etc.”

He decided that rather than being a full-time employee in someone else’s company, he would build his own. In 2022, he officially started Misnomer LLC.

Reach out to your contacts and build a support system.

Levinson began the decision-making process by reaching out to a handful of other women she knew from her agency days who were now running successful businesses, after having children. 

“It was still scary at first, but in working with several startups and innovative entrepreneurs I learned from them that sometimes the best way to start a business was to ‘build the plane while you’re flying it.’ So that’s just what I did,” she says.

Lerner attributes the success he’s found thus far to the great support system and advisors he had that helped him with the decision along the way.

“We certainly discussed the pros of being your own boss, from tax benefits to scheduling flexibility, or simply the ability to meet so many new professional contacts,” he says. “We also talked about the challenges that are sure to arise, such as months of less-than-expected revenue, building a pipeline of business or even chasing clients for payment.”

Keep in mind that there will be growing pains when becoming self-employed.

Levinson found her first client quickly, and has since followed him to his second company where she now functions as their director of public relations. 

“I spent the first two months on my own just networking and letting practically everyone I knew in both my personal and professional life that I was doing PR consulting solo,” she said. “There were some growing pains as I learned to both service an account and also be a business owner at the same time. I hired an accounting firm to handle my books and finances. I also had to learn to pitch new business at the same time as handling the day-to-day of my clients, something I’ve not been as comfortable doing in the past.” 

Do what works best for you.

Levinson has been her own boss for two years, and has built a mutually beneficial relationship with her clients.

“My clients know that I am available to them whenever they need me during my working hours, and I get a contract and stability in return,” she says.

For budding entrepreneurs, Levinson says she’s learned that it’s better to look in than out. 

“Sometimes it’s better to just begin and sell what you know, then learn more along the way and eventually sell that too, whether that’s your knowledge, a service or a product,” she says.

Know that becoming self-employed is a struggle—but it’s worth it.

Lerner cautions budding entrepreneurs to be aware that the struggle is real

“While this first year has been a success financially, it also comes with the realization that there are no guarantees of continued success. It takes time, energy, commitment and even money to start a business and to do it well. It is not for everyone, that is for sure. But if you have the drive and passion to build something amazing, you should dive right in,” he says.

Photo by SaiArLawKa2/Shutterstock

Jill McDonnell is a Chicago-based content writer and communications professional. She has a bachelor's degree in magazine journalism from the University of Missouri-Columbia and a master's degree in public relations and advertising from DePaul University. She is currently at work on a psychological thriller novel.