A is for Aggressive: Owning My Scarlet Letter as a Woman in Business

Jennifer Hoffman
6 min readFeb 19, 2020

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The ‘Charging Bull’ and ‘Fearless Girl’ statues on Lower Broadway in New York. Photograph: Mark Lennihan/AP

The concept of the ‘Scarlet Letter’ dates back to 1850 when Nathaniel Hawthorne wrote the book and where the letter was used to evoke the public shaming of Hester Prynne for adultery. However, Hester goes on to challenge societal norms and proudly displayed the Scarlet Letter A on her clothing symbolizing both strength and ability. It also stands to point out the meaningless judgement being imposed on her by the community over her actions which were committed without ill intention. By the end, the ‘Scarlet Letter’ becomes a powerful symbol of Hester’s identity, again representing her strength but also change and transformation.

My scarlet letter is an A and it stands for Aggressive!

Through my own personal experiences, I’ve found that if you are a strong and confident woman within the business world, you get called aggressive. This label ‘aggressive’ has literally followed me my entire career. (Maybe I should start wearing an A on my jackets like a broach?) In fact I recall a situation a few years back where a client decided to express his opinions, stating that it must be tough for me in business and my dating life considering I was 1) An aggressive female 2) An American and 3) A Redhead. I was truly baffled that he had the audacity to say this and in a professional work setting nonetheless. It took every ounce of my patience not to get up and just walk out of the room.

Having ambition and speaking with authority are not aggressive acts. When a woman speaks her mind, she is simply asserting her view and expressing her opinions, however in turn she becomes labeled aggressive.

Recently I had a review meeting for a promotion I had been requesting and the feedback I received was that not only did they (the men reviewing my request) find me to be aggressive, but they also felt I was dominant, too ambitious, difficult and emotional! All pretty horrifying for any woman who’s trying to reach the next level in her career and the executive level nonetheless. But worse, was that despite all of these colorful adjectives used to describe my personality and character, my boss was unable to give me clear examples of said behavior. As you can imagine, this left me even more confused — no clarity on meaning, no examples to substantiate, how was I supposed to improve in order to progress within my career?

Now my younger self, probably would have exploded with anger, validating the aggressive and emotional points, however 15 years into my career I thought to myself, here we go again, being called too aggressive, what does that even mean anyway?

The definition of ‘Aggressive’: ready or likely to attack or confront; any action that inflicts physical or mental harm upon another person.

Now, I am not one to attack or ever intend to inflict harm on anyone else, my nature is quite the opposite, to champion, motivate and support those around me. But of course, these are my own opinions of myself, so I decided to seek validation or at least clarification from others I have worked with over my career on whether or not I displayed these types of behavior.

It was a very interesting and painfully self reflective exercise I have to say. In addition, the colorful adjectives just kept coming to describe my personality and character, really making me realize the magnitude of my energy and impact on others around me. They included terms such as assertive, ambitious, authoritarian, bold, direct, effective, passionate, confident, sarcastic and snarky, but never aggressive! Interestingly though, there was one common thread across nearly all dozen or so people I spoke with, which actually had nothing to do with myself, but everything to do with the committee who had described me as aggressive, dominant, emotional and difficult. The comment that kept being made was — ‘They feel threatened.’

In my experience, feeling threatened usually stems in some capacity from one’s insecurities which ironically enough, brings the whole concept of labelling a women ‘aggressive’ full circle. This label has been responsible for creating tremendous insecurities in women within the business world, more so than just about anything else. It causes us to over analyze and over compensate, constantly worrying that we might come across as ‘too aggressive.’ When this happens, it can be perceived as weakness or lacking confidence and then you’re left with a separate host of problems as a woman trying to advance her career. It’s really such a catch 22 situation, especially if you’re a woman aspiring to hold an executive leadership position. It’s been well documented that the more successful you become as a woman in business, the less likeable you become by both men and women. I feel this is one of the reasons holding many women back from seeking more executive leadership and management positions today.

One of my favorite studies which Sheryl Sandberg, COO of Facebook, talks about often is the research study conducted in 2003 by the Stern School of Business at NYU. Howard vs Heidi is a study where students were asked to assess the likability and leadership capabilities of an entrepreneur by reading about their education and career path. Half of the class received a case study about a female entrepreneur named Heidi, where as the other half received a case study about a male entrepreneur named Howard. The single, solitary difference within these two case studies, was simply the name of the entrepreneur. Howard was perceived to be an ambitious, likeable guy, someone with strong leadership skills whom you would want to work for. Heidi was perceived to be selfish, out for herself, and foreseen as being slightly ‘political’ in her decision making. The most interesting part of all, this was a true story about a successful entrepreneur and Venture Capitalist in Silicon Valley, Heidi Roizen.

The end result from the study was that societally, we unconsciously or consciously believe women should be kind, polite, and helpful. Sadly, the moment women begin to exhibit behaviors traditionally associated with men, strong, confident and out spoken, we get labelled negatively.

So I’d like to propose that we change our viewpoint and make being aggressive a positive thing! Let’s allow it to empower ourselves and the other ambitious women around us by being more intentional with how we are utilizing the term. Not to mention, the liberation that will come from embracing aggressiveness towards uplifting and empowering those around us. Let’s use it to describe women who are achieving great things in both work and their personal lives, because they are aggressively pursuing their goals.

Why shouldn’t we be aggressive about what drives our passion and our ambitions? The goals that we, strong and capable women, want to achieve? I truly believe we should be unapologetically selfish about achieving our lofty goals and to speak our truth for what we believe to be right in this world. Because remember, we only get to do this once, we only have one chance to become who we want to be and to create the life we’ve always dreamt of.

So if being passionate about my beliefs and what I stand for, assertive in speaking my mind and expressing my thoughts, direct with my communication, bold with my ambitions to shoot for the stars and confident in who I am as a woman makes me aggressive, then so be it. I will wear my scarlet letter with pride.

Thanks again for reading more about my journey in business and leadership, if you have questions on the above, or simply want to chat, please feel free to get in touch!

Here are a few of the books which I’ve enjoyed reading over the past few months or so regarding women in business:

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Jennifer Hoffman

CMO: B2B SaaS & FinTech, Hype Woman for Female Founders, Marketing & Growth Advisor, Venture Builder.