The Best Time To Start a Business is Never O'Clock

Last week I was invited to a women networking group that was meeting in Uptown to watch a documentary on Ruth Bader Ginsburg and have some dinner and discussion. I honestly didn’t know much about Justice Ginsburg other than the memes and marketing hashtags I see occasionally on Instagram. It was a great documentary, and I was glad to learn about her amazing fight for gender equality in the 70’s.

After the documentary, we broke into small groups with discussion questions. One of the questions asked, “Were you the first woman to chart an unfamiliar territory?” And, I had to pause. I was. But I hadn’t realized it.

I shared with the women in my group what had happened when I went to my dad about starting my own business. I remember exactly where I was (pacing on the back porch of my boyfriend’s house), weighing the option on what my next career step would be. I could submit my resume for a job that I was semi-interested in at a non-profit, or I could start my own business. I was staring at the red clay earth dug up around the houses’s new foundation when he said what I knew he would say, “If you were married, it would be a much easier decision to start a business. Then you would have the support.”

My dad began a business when my sister and I were very young - like before we were in school young. Perhaps it would be easier to start a business when you are married… but with two little kids and a wife who was raising them, is that a good time?

“Or,” I replied, “it’s better that I don’t have a family, because if I fail, it will only affect me.”

My father, not one to agree easily, replied with, “Yes, but you would at least be on someone else’s insurance.”

Rebuttle: “I can always get my own health insurance. I don’t think it’s that hard.” (It wasn’t.)

The reality is: there is no one perfect time. Family or not. Married or single. It’s all a gamble, as are most big decisions in life.

In modern America, I felt like I was unique to this experience. Aren’t women raised to be independent here? Don’t they have the support of their family to do amazing things - husband or not? But our family isn’t special. I’ve met several women my age who struggled with this conversation with their families as well. Because family wants you to be secure, to have stability - no matter if you’re Italian, Irish, Polish, or Colombian. And I would imagine that whether you have a son or daughter, you want them to be successful and support them in that process no matter what it looks like.

I don’t know if it’s my generation, or maybe just my geography, but there are many of us who are the firsts in our family to start a business, to leave the corporate safety net, and to try something on our own. We are firsts to cement our claim in an industry that is as familiar as the Wild West. We are pioneers in our own way - regardless of gender or marital status. And that, to me - no matter the final outcome - is a success.

Cassandra D'Alessio