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Business Inspiration, Leadership, Women in Business

9 Female Entrepreneurs Tell Us About the Moment They Got Over Trying to Be “Likable,” and Why it Paid Off

10 Female Entrepreneurs Tell Us About the Moment They Got Over Trying to Be "Likable," and Why it Paid Off

Do you worry about being “likeable” over standing up for yourself? Jennifer Lawrence recently penned a powerful essay on the pay gap between her and her male co-stars, saying she takes responsibility for not getting a higher paycheck because she was too caught up in being “likable” instead of advocating for herself. We talked to 10 women business owners/entrepreneurs who decided to put revenue and reputation before rapport, and began advocating for themselves.


I am currently in the middle of a major shift in my ability to advocate for myself and our organization’s needs. I just wrote about this shift on our blog. Here’s an excerpt from the blog post: “I’ve realized recently that no one has ever accused me of stepping on their toes. So I don’t know why I worry about it so much. In fact, I had a wake-up call a couple of years ago when I was about to speak up in a team meeting where I was working at the time. I prefaced what I said with “I don’t want to step on anyone’s toes but…” And my friend and co-worker at the time interrupted me to say “Leslie – you ALWAYS say that and you NEVER step on ANYONE’S TOES…just tell us what you want to say! We really want to hear it!’”

Leslie Coles, Co-founder/Executive Director, The Moms as Mentors® Project

I’m known as the “friend,” although I’m the boss and the owner of the company, and I’ve always been overly-friendly with my staff. I was trying to be the likeable “nice boss,” but I was not seeing results and my business was suffering. Two years ago, I started working with an executive coach to change that. Last month, after 16 years in business, I finally started changing things and let half of my staff go in a move to restructure and start over. No more Mrs. Nice Gal! The result so far has been wonderful (on a side note, the office is so much quieter, and I’m able to get so much more done). My husband, who manages a number of employees, pushed me to not be everyone’s friend – he said I have plenty of friends, and they shouldn’t be my employees. Now, as I’m starting over, I’m cognizant of doing it the right way, in a friendly, but not overly friendly, and firm way. In the past, staff would take advantage of my kindness and misconstrue it as a way to be underproductive.”

Georgette Blau, Owner, On Location Tours

I am now a small business owner, but have experienced this issue when I worked full time for another business. I made the mistake of taking the first salary I was offered and not negotiating a higher pay (as women often do). For the first six months, I really focused more on being an asset to the company and showing the value I brought to the table over trying to make friends or being likable. After that, I gathered research based on my skill and highlighted how I helped the business successfully grow. This allowed me to negotiate an $8,000 raise. Which interestingly enough, after two months, I quit and launched my own company anyway.”

Octavia J. Gilmore, Owner/Chief Creative Officer, Creative Juice

Unfortunately, advocating for myself often lands me in the unlikable category. As a black woman, inherently, I am not received in the same way as my counterparts. It’s not easy to speak up about a topic that is not in line with the opinion of others; it leaves you feeling vulnerable. In the past I would choose not to express my thoughts because I feared I would create a reputation that would harm my professional advancement. Furthermore, I felt like what I had to say didn’t matter and was convinced that I didn’t have the power to make a change. Ultimately, I discovered that holding back not only results in me losing 100 percent of the time, it impedes on the progress of the next generation working to achieve their dreams. I have no choice but to speak up. It’s my responsibility.”

Sarah Juma, Cofounder/Managing Director, StyleID

A force to be reckoned with: I stopped being frightened of advocating for myself when my husband passed away, leaving me with four little kids to raise, financially and otherwise. It is amazing how trading that fear for ones that are more real (starvation and homelessness) liberated me. I’ve since become a successful media and tech entrepreneur, award-winning children’s television creator, author and CEO/owner of THREAD MB, and my children are all highly-successful budding surgeons and scientists.”

Laura Wellington, CEO, THREAD MB

I was an elementary school teacher in a small private school for many years. I never pushed or advocated for a higher salary, even though I knew I was liked and respected among the parents and administration. Looking back, I think there were a couple of reasons I didn’t push. One, of course, was discomfort. Another was an intimate understanding that the school didn’t have much money. And finally, as both a teacher and a mother of a student in the school, I received a tuition discount on top of my salary.

I now run my own book publishing and book coaching business. I am unapologetic about my fees, and anyone who isn’t ready to make that investment in themselves is not the right client for me. I think the difference may be that I’m now in the position of power. If someone isn’t ready to pay my asking price, I can move on. There are other clients who will. And though I never questioned my job security at my former school, the ultimate reality was that if we didn’t sign a contract that they liked, I was the one who would have to face the hassle and challenge of finding another job.”

Esther Goldenberg, Owner, Three Gems Publishing

I write proposals for small businesses who are interested in getting into government contracting by selling their products and services to the federal government. When I first started my business, I was concerned about likeability. Many small companies live or die based on their awarded work to the federal government, so when working with small businesses, it was difficult at first for me to assert myself and be more demanding when it came to my customer providing me the information I needed in order to produce their proposal. Many customers did not want to hear bad news or be told that their information was lacking. At first, I found myself being very apologetic and not pushy enough. These customers hired me to push them and ensure that their proposals were compliant with government standards. I knew I needed to get over my problems with being liked and just do my job, even if I got my customers upset or irritated. It was honestly the connection I made with one of my customers who showed me that I needed to forget about being liked and just do the work. He was a no-nonsense kind of person who got things done by being incredibly honest with his customers, rather than tell them what they wanted to hear. After experiencing the results of this kind of approach, I modified my interactions with my customers. I learned to be more demanding, tell them the truth about their proposal and care less about feelings or my ‘niceness.’”

K. J. Gillenwater, Owner, KJB Writing Services LLC

I’m fortunate in the sense that I grew up with a father who ran a business and was always very candid with me about the challenges of doing so. I’m proud to say that I’ve never signed an employment agreement without negotiation, but when I was younger I certainly didn’t negotiate as well as I should have (although I quickly recognized that negotiating at all meant that I was getting paid more than many of my peers).

Now as a business owner, I certainly see situations where prospective clients expect me to be a pushover. I try to be both diplomatic and scientific in these instances, and if a client pushes too hard, I simply welcome them to go to the market for additional quotes. Those that come back are generally grateful that I was candid with them, and I am always glad that I didn’t commit myself or my staff to a project that doesn’t make sense financially. In the short term, it’s uncomfortable to say no, or to ask for more – but trust me, it gets easier over time, and the rewards are cumulative.”

Amber D. Scott, Founder/Chief AML Ninja, Outlier Solutions Inc.

Early on in my career I was working for an extremely established company that was very comfortable to work for, and I had a ton of great colleagues, but not a place where “strong” personalities were common. One of my first performance reviews pretty much said that I needed to be “nicer.” That is, I should keep sharing my opinions, but temper down my approach. That was one of the last signals I needed to know that established organizations would never be my thing, and that I wanted to be my own boss somewhere down the line. I went on to attend Harvard Business School, join a series of start-ups as one of the earliest employees and most recently start my own business. And one thing is for sure: it’s been years since I’ve “been nice”.”

Laura Troyani, Founder/Chief Editor, PlanBeyond.com

Do you advocate for yourself instead of worrying about being “likeable” at all costs? Tell us about your experiences in the comment section below.  If you’re interested in learning more about Kabbage, visit our business loans for women page.