A Reluctant Entrepreneur: My Mom's Unlikely Path To Becoming A Small Business Owner

There’s an old saying, “The more things change, the more they stay the same.” Even as we evolve, there is basic continuity in the human story. As I join Fairygodboss this month as Editorial Director, I've been thinking about my experiences as a female student in fully coeducational settings and how those compared to my experiences upon joining the workforce.

Throughout my education, my classes were generally comprised of equal numbers of males and females, and my teachers seemed to have equal expectations of us regardless of gender, race, or ethnicity.

Out in the real world, the playing field has never seemed quite as level. I've benefited from working in offices (in the fashion industry and in the arts) with predominantly female colleagues, many of whom became mentors; when I ventured into publishing, where the staff was an equal mix of men and women, I quickly worked my way up to a management position. 

Yet I've also had to say goodbye to some highly talented women who have guided me — women who, while raising young kids, were forced to look for new jobs that offered more flexibility. And many of my friends, working in fields including business, education, and law, are employed in offices where the majority of managers are men, even when women constitute a substantial percentage of the staff. 

When my parents met as colleagues early in their law careers, they were complete equals, both with Ivy League credentials behind them. So I wondered how it evolved that my mother left her legal career to raise my sisters and me while my father continued working as an attorney. And how did my mother end up pursuing an entirely new business venture, eventually bringing in my father when he was ready for a change?

I decided to interview my mother to give me some historical context regarding the realities that working women face.

"Owning my own business was not an easy step for me," my mother told me when I inquired about her unconventional career path. When she left her job as a criminal defense lawyer to raise my sisters and me, she certainly did not expect that she would end up as an entrepreneur, eventually opening a tutoring business working with students preparing for their college entrance exams.

After graduating from Yale in 1978, relatively early in its history of coeducation, my mother studied law at UC Berkeley; she landed a job in New York City as a criminal appellate lawyer at the Legal Aid Society, where she met my father. Several years after my older sister was born, they moved to the suburbs looking for more affordable space, access to the outdoors, and good public schools. My mother’s temporary leave of absence from Legal Aid turned into retirement when I arrived.

Years later, as my sisters and I were increasingly independent, my mother struggled to find a way to re-enter the workforce. She had held a multitude of volunteer positions, including chairperson of the PTA at our elementary school, and she had taken on various part-time paying gigs along the way. But by the time she was ready to re-start her career, technology had drastically altered some of the fundamentals of the workplace and even the process of searching for work. A chance conversation with a PTA colleague led to a job at a neighborhood pre-school. Soon afterward, my mother was hired by a local company to tutor high school students, before she eventually partnered with another woman to open their own tutoring company in Northern Westchester County.

My mother shared with me the ups and downs of being her own boss and recalled how some experiences she had as a stay-at-home parent unexpectedly helped shape her trajectory. 

When I headed off to college, I thought about teaching as a profession, but my father dissuaded me because wisdom had it that there would be a shortage of teaching jobs available. Although women comprised a good percentage of my law school class, almost none of my female friends from high school and college chose to go into law.

After law school, I went to work at Legal Aid as a criminal appellate lawyer. Our office had a good mix of men and women in staff positions; however, men predominantly held the supervisory positions. From what I could gather from my friends’ experiences and from going through the job interview process, there were even fewer women in partnership positions at private law firms.

Interestingly enough, our office allowed for maternity and paternity leave. Your dad I both worked halftime initially when your older sister was born. However, your dad did not find much of a community of other fathers at home, and he ended up preferring to go back to work fulltime. I was happier as the stay-at-home parent, although I did continue to work part-time at Legal Aid when we only had one child.

I was anxious about re-entering the work force after spending time at home. For one thing, technology had changed my profession. I learned to do research in a law library, but during my years at home, legal research had gone online.

At the point when I left the office, we handwrote our briefs and brought them to a secretary for typing. With the development of word processing, those patterns changed as well.

It was largely thanks to the volunteer positions I took on when I was out of the workforce that I eventually mastered the computer for creating documents, doing research, and using email. As an attorney, I had to appear in court to argue my cases; when I chaired the PTA, I again tackled public speaking.  For both the PTA and my work on the board of a local youth theatre company, I learned to analyze and manage an organization’s budget and to tackle online research.

Of course, I also took on few paid positions along the way — helping with marketing at a local music company and doing some editing and file reports for your dad and uncle. Those jobs helped with our finances, but more importantly, they added to my skillset and sense of self-worth.

I gravitated toward some of the service professions, which did generally attract a relatively high percentage of female employees.

By contrast, in my economics class at Yale, I was one of just three women. I observed that the graduate school teaching assistant (a man) called on me during every class. When I approached him to suggest that he was calling on me out of proportion to the men in our class, he mocked my concern by fake crying.

While my decision to go into the public sector in my legal work was not consciously related to the relatively higher percentage of women at Legal Aid, it was probably not entirely accidental that I was drawn to a field that attracted more women than did some other law jobs.

When I went to work at the pre-school, the connection came about thanks to the recommendation of a woman I knew through the PTA. When I was hired for my first tutoring position, I knew the company’s owner because you had tutored with her and because she and I were active in the same volunteer organization [a summer scholarship program]. So I have certainly benefited from a network of women with shared life experiences and concerns that are shaped by those experiences.

In fact, at that first tutoring job, my boss immediately remarked that as a mom herself she understood the demands of parenting, and that she would find someone to cover for me if I needed to be elsewhere for my kids.

Last year, we employed a mom with young children: she thanked us for our understanding when she twice had to leave suddenly due to emergencies with her young kids. So I am very cognizant of the realities of balancing parenthood and workplace duties. I also recognize the great talent pool available in that pool of young mothers who may have had to leave their full-time jobs.

Owning my own business was tough — I had very few business skills, and I’d never had dreams of becoming an entrepreneur.

In fact, I joined with a female math tutor whose background was in accounting, so she handled much of the financial aspects initially. She was the one who took the first steps toward opening the business.

While I have loved the chance to be my own boss and to have autonomy, it remains challenging for me to find the right voice when I have to direct and occasionally criticize employees — men and women.  A young male employee once accused my former partner and me of sounding like his mom!

I took a long time before I would even consider running my own business. I was expert at following rules, but much less comfortable with making them!

I quite enjoyed the time I took off from work to be home, so I have absolutely no regrets. However, I think that if I had followed the career I originally wanted in teaching, I would have found a way to get back into the work force earlier and with less fear. That’s partly because the workday would have meshed more easily with my desire to be home in afternoon/early evening with my kids. I also would have had easier access to local teaching jobs. I have noticed that many female lawyers I meet end up leaving the profession once they have a family.

Volunteering was a great way to do meaningful work that took me out of my comfort zone and thereby expanded my skills. Chairing the PTA — a nearly entirely female organization — allowed me to take a leadership role that I might not have had the chance or confidence to take on in a traditional work environment. In the same way that at least some young girls might benefit from having some experience in some single-gender environments (whether in a classroom, a club, or a team), it was helpful in my current work to have had those volunteer experiences in some largely female-dominated arenas.

In other words, not only did volunteering provide enrichment during my years out of the workforce, but I also think that by volunteering I had developed some skills I would not have taken on as readily in a traditional workplace setting.

I should also add that my experience was certainly colored by the fact that I entered college in the relatively early years of coed education at schools like Yale, when the student body was still heavily male.  When your sister attended Yale decades later, I could see that women made up fully half the population and nobody questioned their place in the community.

So the picture is changing for the better, but I do think it remains tough in many workplace situations for women to rise to leadership — that could be because the idea remains threatening to some men, or as a result of institutional bias, or the outcome of the years taken off from work to raise families.