How Generationally Women Entrepreneurs Differ on Sexism

Does age change a mindset on reality?

In 2019, I had the pleasure of attending the Women In the Black Conference in Harlem. It was my first time to the conference and I randomly learned about it while checking out booths at the Small Business Expo held in June 2019. I was very excited to meet other Black women with successful small businesses and also soak up wisdom and knowledge. I definitely gained in both regards, however something that still plays over in my mind is a moment I shared with an older Black woman during the conference.

Many of the women in attendance were in an age group different from mine. Nearly all had been in Harlem for longer than I have been on this planet. They have seen the ebbs and flows of the community. They have championed for Harlem and worked diligently to maintain the historical area of Blackness, despite the onslaught of gentrification. Most notably, they grew up during a time when societal norms about what men and women are allowed to do now serve as stark contrasts to what are the norms today, and beyond.

Among the various shades, colors, and show-stopping fashions I witnessed at the conference was a different way of communicating, presenting, and discussing business. It was clear to me that a majority of the women knew each other personally and participated in this organization to carry on traditions, legacies, and economic development in their community, in their Harlem. Early on in the conference, I found myself at a table with a woman who had started her own beverage company. Rightfully so, I was intrigued and struck up a conversation with her to learn more about how she started her business, what the struggles had been, and whether she needed any marketing help.

“You should always ensure your appearance is good. You know what I mean right? Dress up, look pretty, and presentable, then they will take you more seriously.”

Being that I already appear younger than I am, I could tell by the initial start of our conversation that this accomplished woman—her beverages are in Walmart as well as several airports—took my youthfulness as an indicator of my naïveté of how business is conducted in our society. As she shared the amazing story of how she had scaled her business, what the conference meant to her as a previous winner of the business pitch competition, and how she managed her business’ social media, we somehow landed on the topic of how a majority of men are able to succeed with limited knowledge, capabilities, and the like—simply for being men.

As I raised a point of how I had potential clients who choose not to work with me because my prices are “too high”—yet I knew from research and lived experiences that if I were a man they would most likely not question my pricing—this accomplished woman turned to me and said, “You should always ensure your appearance is good. You know what I mean right? Dress up, look pretty, and presentable, then they will take you more seriously.” Now, I was raised in the South and the one thing you are always told is to respect your elders. In the moment this accomplished woman made this statement to me, two things crossed my mind: 1) let me see where she takes this, perhaps it won’t stay in this space of what a woman ought to do to be taken seriously, and 2) this thinking is problematic, but I respect her right to express her opinion.

I imagine she must have noticed a slight shift in my demeanor because she followed up with, “When men go out to sale a business or get business, they buy a fancy watch, nice suit and shoes, to dress themselves up and then nobody questions them on their rates or prices.” And there it was, the understanding that sexism seriously undermines the efforts of women business owners. Yet instead of ideas, notions, or actions to dismantle that biased behavior, an accomplished woman was suggesting I do as most men do to hopefully combat the discount-seeking clients who find my prices “too high.” I told her I agree that men do get to use that approach and find success. However, I failed to fully speak my mind with her; likely because I did not want to offend or show my elder any disrespect—yes, another societal norm that should be broken in certain instances. But, I also informed her I do not feel I need to attract clients based on my appearance as those clients looking to make a decision based on my outward appearance are not the kind I want hiring me.

I learned from multiple incredible women that day. The one at the top of my memory is the owner of the beverage company because I want to remember what women entrepreneurs are up against every day we operate our businesses.

The most unfortunate part of this exchange was I found myself thinking, internally, am I underdressed for this conference? Yes. I started to critique myself, in a room primarily filled with women. It’s amazingly wild how women are indoctrinated to doubt and question ourselves. To my credit, I made the attempt to be presentable for the conference outside of my normal jeans and a nice shirt go-to for these sort of events. But wearing high heels or dress sandals? Nope. Wearing any makeup? Nope. Freshly styled hair do? Nope. In that sense, I was failing at what this accomplished woman was putting out there as a means for me to be taken seriously with the pricing of my marketing services.

How did our conversation end? Well, she needed to leave our table to head to the judging panel for the pitch competition and so we said our goodbyes as she did. How did I manage the rest of the conference? Well after I got out of my own way with being unfamiliar with the women in attendance, I garnered garner interest in my services from four women; I spoke during discussions in two breakout workshops about scaling income and how to effectively use social media to market a business; and I made a connection with another accomplished woman who invited me to her entrepreneurship conference, potentially as an affiliate. That one moment of aha!, of this is how different we are as women from different generations—battling the same societal norms and behaviors that hold women back from successful entrepreneurship—did not derail me from my purpose in attending the conference.

I learned from multiple incredible women that day. The one at the top of my memory will be the owner of the beverage company because I want to remember what women entrepreneurs are up against every day we operate our businesses. I also want to remember how generational experiences guide how women business owners view the challenges each of us will face and what choices we will make to see our businesses succeed.

DTC Product Marketer. D&I Researcher. Dog Mom.

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