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Comeback Careers
May. 10, 2018, 9:03 PM UTC
Career Growth

Returning to the workforce as an entrepreneur

From employee to entrepreneur, Jennifer Scherer discusses her return to work and becoming a business owner with comeback careers contributor Ginny Brzezinski.
Image: A woman works from home
Onest Mistic / Getty Images

Jennifer Scherer never imagined that an event she auctioned off for a school fundraiser would turn into a full time business. For seven years, the mom of four had been home with her kids after a long corporate career. She had just begun interviewing to return to work and surprisingly, her business started almost accidentally.

“It started out as a dinner group where I put together a kind of “Amazing Race” with people on teams followed by dinner,” the 2017 Grow Your Value contest finalist and founder of Magnified Events ( told me recently. “Then someone asked if I could auction that (idea) off for a school fundraiser. It made a decent amount of money, and then someone asked if I could do it again. I began to introduce different themes and options. It was getting to the point where it was raising $5000 - $10,000 for these auctions. Then someone who was attending one of my events in town asked if I would ever consider doing one of these events for her company.”

Jennifer was trying to return to work at the time and almost missed the business opportunity that was right in front of her. “When I was asked to do this, I had been on a parallel path interviewing to go back to work. It was so discouraging and seemed so boring. When I got this request, I thought, ‘I don’t know if I can do this, I don’t know if I have time since I am interviewing.’ When I look back, I can’t believe [this business opportunity] was right in front of my face and I didn’t even see it right away.”

It was 2015, and the company was NBC Sports. That first paid event led to others at NBCUniversal, Citibank, NBC Sports and Healthfirst. Jennifer now has two full time employees - both of whom had been stay at home moms. She also has temporary employees who help with her events.

Starting back after a seven-year career break she says, “It was shocking that someone would pay for what I did. Maybe it’s because I had not been paid a salary in so long.” One of her biggest challenges was simply believing in herself. “I think I got physically ill before my first event.

I met Jennifer last fall at Mika Brzezinski’s Know Your Value conference, and caught up with her again recently. Jennifer says that for her, being her own boss makes sense, giving her more control over her schedule. “For me and my husband both to be in the city all day, it’s not feasible to hire someone to do everything, plus I want to be there (for my kids),” she told me. “For my life right now with four children, one going off to college and my husband working a really demanding job, this is really good. I am making money, my existing skills are getting sharpened, and I am developing new skills. Most importantly, I am able to do it on a time schedule that works for my current situation.”

Scherer is not alone. Recent data show that an increasing number of women who want to control their schedules, pursue an interest, or be their own bosses are starting their own businesses. In 2017, there were an estimated 11.6 million women-owned businesses in the United States, an increase of 114% compared to 20 years ago. Women are launching 849 new businesses a day, an increase of 3% over last year, according to the 2017 State of Women-Owned Businesses Report from American Express, and like Scherer, some of these women had off-ramped for a few years from corporate careers to take care of their families.

Diane Flynn, cofounder of the job training and placement firm for women returning to work, RebootAccel ( says being your own boss has a lot of appeal for women after a career break. “The thing that is really appealing for returners who want to be entrepreneurs, is for the most part you do have a lot more control over your schedule, and you can work where you want and when you want,” says Flynn. “We do have people who want and need full time positions in an office, but that’s not everybody. Lots of people want to work but they don’t necessarily want to report into an office 9-5.”

Flynn noticed that about a third of her return-to-work clients at RebootAccel were interested in starting their own businesses - from consultancies to non-profits to small businesses. In response, in 2017 RebootAccel offered their first workshop on entrepreneurship for women who have taken a career break. The company is now developing an entrepreneur track geared toward women who are pivoting in their careers or have taken a career break.

“A lot of people were approaching us saying: We want to do our own thing. They want to make a difference and they want more control over their schedule and flexibility.” She said the graduates of RebootAccel’s programs have gone in a variety of directions. “Some of them are hanging their shingles (as consultants), we have one who started a college counseling business, one client started a clothing line. We had one who started a mental health service in our community to try to provide services to kids who need help.”

Singari Seshadri, director of the Stanford Venture Studio ( is working with ReBootAccel on their entrepreneur track. She spent more than a decade in venture capital investing, incubating startups, and co-founded an accelerator program for women exploring entrepreneurship as a career path. She says it is critical for potential entrepreneurs to understand their priorities, to find a low risk way to test ideas and to know the difference between a passion project and a viable business.

“What I tell women is the perfect job doesn’t exist,” she told me. “I make it very clear to them that they should know what their priorities are and go in to the entrepreneurial path with eyes wide open. I hear the flexibility piece a lot - I always ask them: how do you define flexibility? Yes, you get a lot of flexibility by running your own business because you are your own boss but it is also a 24/7 job. So, define what flexibility means to you. Make a check list of what your priorities are. Is it important that you are home every day when your children come home from school? Or is money important, or a career path, or impact - figure out your top priorities and see how many boxes you can check. Make sure it checks most of the important boxes.”

For women who have been on a career break there may be fewer downsides - they are not risking paychecks and benefits, and the experience could add something fresh to their resume. “If you are out to the workforce anyhow and you spend a few months testing out an idea - that gives you something to put on your LinkedIn profile.”

Scherer agrees. “I felt even if this business doesn’t succeed in the long run, I am getting skills and taking steps forward to at least make myself look valuable in some ways. My approach was always to keep one foot moving forward.”

Her advice? “I must hear constantly ‘no one is going to hire me’” but it’s not true. Put one foot in front of the other. Figure out what you like. It’s definitely doable.

“Keep your eyes and ears open. Most things that people do, if they’re smart about it, can be a business. If you’re smart and you’re a hustler, you can get creative and find other things to do that actually are so much more rewarding and more profitable than trying to get back into the traditional role (you) may have had in the past.”

“The only thing you know is that if you do nothing, nothing is going to happen. Even if you just try. This is not the first business I started. The other ended horribly. Even if it doesn’t work out well the first time, things that you don’t even imagine can happen as long as you are moving forward.”