Why Starting A Business As A Woman In Your 30’s Might Be More Difficult Than You Think

It never occurred to me that I shouldn’t tell the truth. I unabashedly discuss my age in an entrepreneurial world that I’m not sure accepts it as normal.

I attend lots of meet-ups and conferences where I’m definitely the oldest female founder in the room. (Have I mentioned that I have a strong dislike for the word “female”? I do. It reminds me of an animal but… I digress.)

I’m a 39-year old woman who decided at the age of 34 (ish) to implode my life and start over…on my own terms. Yay for me. Right?

Sort of.

But not always.

Starting a business at the age of 35 brought on a shit ton of challenges that I didn’t expect. And my expectations were lower than most since I never set out to start my own business or empower anyone, other than myself.

Finding community was one of the biggest challenges that I came up against as I transitioned from a corporate job into entrepreneurship, in my mid-thirties.

I was too old for the millennial community who were raised in the age of risk-taking and entrepreneurship. Their technological ability was light years ahead of where I was regardless of the fact that they were 10 years younger. Personal computers (and Facebook) didn’t exist when I was growing up. We played Atari and had TI-83 calculators for math class. And if you were REALLY badass, you had a portable CD player. Using Facebook or Instagram for business?! Wha..what?! I. Had. No. Idea. ***For the record, I learned quickly.

I was often too young and sometimes too attractive to fit in with a lot of male founders that I met. I don’t say this out of vanity either because, quite frankly, I’m not that different than a lot of other women who experience this. I remember having a conversation with one highly regarded entrepreneur worth billions (no kidding) of dollars. You know his companies. Very well. I kid you not when I say that I’m confident he already undressed me by the time he handed me his business card (in his mind, NOT literally.) Younger male founders wanted to take me out for a drink, not taking me seriously at all since I was new to “tech” business and I’m sure didn’t get the language right. I recall describing The Collective in its early stages and one guy said this “It’s interesting because women are so sensitive about business. But I really don’t understand why they’d pay for cheerleading. You may really want to reconsider this model.” Yep, he said that. He also repeatedly told me how “cute” I was. Needless to say, I didn’t take his advice.

Several older male founders didn’t take me seriously either (because “my god, you’re so smart and so…beautiful.) No shit, Sherlock. Thanks for the sincere business advice.

I had nothing to reciprocally offer the community of women business executives who I no longer had much in common with. I was never going to be a high-powered executive. I was never going to wear 4” heels to the office and I wouldn’t be caught dead in a knee-length pencil skirt (anymore.) I didn’t care much about being promoted and I sure as fuck wasn’t ever going to backstab for the sake of a promotion. YES, of course, I recognize that not all women executives behave that way but I know for sure that corporate culture changes people. You do things at work as a “leader” that you would never do outside of work. It’s very easy to allow your morals to shift in the name of the business if your hope is to keep climbing that corporate ladder. I KNOW this to be true. And it just wasn’t in me to want corporate success that badly.

At the age of 35, I didn’t have a community anymore. It was lonely, disconnected and it sucked. I had less and less in common with the folks I spent an entire career working with and I didn’t know where to turn to find people like me;

Uncertain but courageous enough to know that they’d figure it out.

Women needing support but also having a shit ton of expertise to share.

Big-hearted women who sought an understandable strategy for growth but also wanted to help others thrive.

Innovative women who had so much to learn but also wanting to empower others.

The Collective (of Us) was started out of necessity. It’s an on-line small business accelerator and community for women business owners.

I created this community as a platform to connect women like me but different; women who didn’t have a community that they related to as they transitioned from one role (corporate employee, motherhood etc.) to that of entrepreneurship.

Women who wanted to support other women while also growing their own businesses to higher heights.

Need is often the greatest innovator. In this case, I know that to be true.

"Need is often the greatest innovator."

Starting a business at any age is challenging but being a woman in your thirties and starting a business has a whole subset of challenges that we should be talking about a lot more often.

Cheers to you going into entrepreneurship with an open heart, a bold idea, and a kick-ass community.

What are your thoughts on the rarely discussed topic of being slightly older founders in a millennial business world? Leave a comment below. 

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Cyndie Spiegel is a Brooklyn-based consultant, coach, and speaker focusing on strategy for women-led startup founders and small business owners as well as the founder of The Collective (of Us.)