Kelly Lester (above) runs EasyLunchboxes, a business that generates $1.7 million in revenue.

Do Entrepreneurial Women ‘Have It All?’

Elaine Pofeldt
Work: Reimagined
Published in
8 min readJun 25, 2015

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Judy Travis, 29, records much of her life on camera — from her husband cooking naked in the kitchen to their giggling one-year-old twins trying to talk to one another. In the smartphone era, she’s not unusual.

But what is different, is the fact she brings in more than $1 million a year in revenue from a variety of sources. Since 2012, she has launched three YouTube channels: “ItsJudyTime,” where she gives lessons on how to use drugstore beauty products; “ItsJudysLife,” a video blog about her life and “ItsMommysLife,” aimed at new moms. The revenue comes from advertising. She manages all of this from her home in Seattle, within easy reach of her three small children.

“I love being a freelancer,” says Travis, who previously worked in a foster care agency. “You have flexibility. You are the boss, but at the same time you are still a mother. Once the girls are taking a nap or in bed, that’s when I get a lot of work done.”

Travis’s business is one of a small but growing number of U.S. firms that are breaking through the $1 million mark staffed by no one other than the owners. The number of such “non-employer” firms that bring in $1 million to $2,499,999 is up approximately 30 percent from 2009.

Travis’ experiences — and those of other mothers who run firms like hers — suggest that for many working parents, running a business offers unique benefits that, in some ways, surpass those of corporate job with flexible work arrangements. As many who tap into corporate programs have found, telecommuting and other options can bring a subtle career penalty that slaps a ceiling on your advancement and wages. Even people who work in the office, but log less than the new norm of 50 hours a week, are losing out, a recent study published in the American Sociological Review found.

“Everyone is complaining that they have no flexibility in the corporate world,” says Steve King, a partner at Emergent Research, a firm in Lafayette, Calif., that studies the independent workforce. “For us, it’s an important metric in terms of figuring out how many people are going to quit and become self-employed.”

Kelly Lester (above) at her home in Los Angeles.

The big question is why, then, given the growing success of micro-businesses like Travis’s, is there so little encouragement for women to start them in the first place. When discussions of women’s careers take place, they usually focus on choosing between corporate work and family — or finding some happy medium between them. There’s little mention of entrepreneurship.

And on the rare occasion that these conversations do mention entrepreneurship, they usually focus on superstars like Sara Blakely, the founder of Spanx, and Elizabeth Holmes, the self-made billionaire who started the healthcare tech firm Theranos. There is little mention of the small and midsize businesses that allow women to create successful enterprises while working from home.

Springboard Enterprises, the best known program to help women entrepreneurs, has been very successful in helping women with highly scalable businesses raise money in a world where equity financing still goes mostly to men. But there’s no group with a similar footprint to encourage women who want to start a business but not necessarily one as scalable as Facebook.

With little support, it’s no wonder that some women running solo businesses diminish what they are doing — and fail to reach their potential. A report by Etsy found that only 74 percent of the those running stores on the crafts marketplace — most of whom are women — consider their Etsy shops businesses. That mindset can’t possibly foster success.

Nor is it surprising that fewer women than men start businesses. Only 37.1 percent of the self-employed population is made up of women.

The most common argument I’ve heard against encouraging more women to try running a micro-business is the high failure rate. It’s one that men hear, too, but the message may be counterbalanced by the unambivalent way society celebrates ultra-wealthy alpha male entrepreneurs, from Richard Branson to Mark Zuckerberg. Women who run thriving home-based businesses, well-aware of what it takes to succeed, are often the first to raise it.

Knickknacks at Kelly Lester’s hone in Los Angeles.

“I think it’s dangerous to come up with an idea and walk away from a well-paying job if there is no obvious indication this will do well,” says Kelly Lester, a mother of three and part-time professional actress who, since 2009, has sold lunchboxes she makes at EasyLunchboxes, a home-based online retail business in Los Angeles and generates $1.7 million in revenue a year. “I know a lot of people who put their heart and soul and all of their money and all of their parents’ money into a business that never should have been started in the first place,” says Lester.

Still, many corporate careers sputter out, too, with similar financial fallout. Losing a job can be just as devastating as watching a business sputter if you can’t replace your income quickly. Meanwhile, many self-employed people do earn a corporate-level income in businesses ranging from internet retail stores to professional services firms. In 2013, the Census Bureau found there were 221,815 nonemployer firms bringing in $500,000 to $999,999; 530,274 generating $250,499 to $499,999 and 1.7 million bringing in $100,000 to $249,999.

These tiny businesses, which can be designed around the owner’s lifestyle, offer some relief from the work-life conflicts that go with either corporate life or running a venture-backed startup bent on hitting a $1 billion valuation.

Jamie Klein (above) started Inspire Human Resources after quitting her job at American Express.

Jaime Klein knows this well. In 2007, after leaving a career in human resources at American Express, she founded Inspire Human Resources, a New York City consulting firm. “I literally started the company with the concept that I wanted to have the flexibility to raise my twins,” she says. Although American Express offered family-friendly work options, she says, “the level of flexibility I wanted at that time exceeded their very generous program.” Still, she loved her career and wanted to continue to do “very interesting” work — something that can be hard to find in a part time job.

Working from the corner of her living room at first, the River Edge, N.J., resident intended to do flexible, project-based work. As demand for her services grew, she gradually brought in other 1099 contractors like herself. Today, Inspire’s network has grown to 25 consultants, all of whom are independent contractors. “I work 40-plus hours around what the house needs,” says Klein, who toggles between working in Manhattan and at home, so she can be involved in her children’s busy schedule of activities. She was planning to run the dunk tank at her children’s school fair right after our interview.

She currently oversees 18 projects run by her consulting partners. “I love being able to work at that altitude,” she says.

Jamie Klein (above) with her children at home in New Jersey.

Meanwhile, she has plenty of time for her children during the hours they need her most. “Having kids who need to go to bed around 8:30, that 3 pm to 8 pm period is key,” she says. “That’s where I hear who they sat with, did they see someone being bullied and how they handled it, and what test is tomorrow. When I roll in the door at 7 pm and say, ‘How was your day?’ their day is done. They’ve processed it with the babysitter.”

Perhaps what will really encourage more women to try solo entrepreneurship is not a formal program alone but a tax structure that is more favorable to entrepreneurs. If microbusiness owners could put a certain percentage of their revenue each year, tax-free, into an account that they could tap as an emergency fund in lean times, they would have more money to invest in growing their businesses and a greater shot at long-term survival. This would be especially helpful to women, who have historically had less access to capital than men and, upon having children, often sacrifice income that entrepreneurial types might otherwise set aside for funding a startup.

The need for an option like this is only going to increase, with more Americans surviving on what’s called “contingent” work — a category that includes self-employment. Many people are now driven to start a business by a yearning similar to Klein’s for a flexibility greater than what any large-scale company program — even an excellent one — can allow. For others, it is the act of “doing the math” regarding their corporate jobs and finding it doesn’t add up in their favor, as King puts it.

“In the old days, if you had a corporate job, you were more secure, made more money and had good benefits,” King says. “You had to give up a lot, but if you did the math it very much favored a corporate gig. Today, benefits have been cut, pay has been cut, work-life balance has been harder. Suddenly the math has moved to self-employment.”

That could mean there are a lot more mothers like Travis, Lester and Baxter who decide to run businesses their way in the future — well-prepared to make the tradeoffs — and plenty of men happy to join them.

Kelly Lester photos by Jessica Chou | Jaime Klein photos by Cait Oppermann

Work: Reimagined is a series of sponsored stories dedicated to exploring the evolution of the workplace.

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Elaine Pofeldt
Work: Reimagined

Former FORTUNE Small Business editor turned freelance #journalist for CNBC, Fortune, Money, Inc., Crain’s New York Business, etc.