pexels women entrepreneurs challenges scaled
pexels women entrepreneurs challenges scaled

Women Entrepreneurs: The Baggage We Carry

Imposter syndrome. A lack of respect from peers. Or burnout so severe it led to a car crash. These are some of the struggles women entrepreneurs shared with us. Running a business is difficult for anyone, but women often encounter additional challenges because of gender roles, stereotypes or industry norms.

We asked a number of women running their own companies and those who work with women entrepreneurs to share the challenges that seem unique or particularly hard for women entrepreneurs.

When your hard work isn’t taken seriously; when you’re having a bad day; it’s good to hear from others facing the same issues and know “It’s not just me.”


Kimberly Inskeep, CEO, cabi: “It’s challenging to be at the helm of a business and ensuring neither you nor your colleagues suffer from ‘burnout.’ This is especially pertinent now during a pandemic. Women often ‘juggle’ multiple things simultaneously.”

Lorrie Thomas Ross, The Marketing Therapist and CEO, Web Marketing Therapy; Wild Web Woman, Wild Web Women: “The number one challenge we see our entrepreneurial women face is FOG, which is how I address our debilitating baggage of fatigue, obligation and guilt. A few years ago, I had that ‘perfect’ life on paper. Business was great, I was doing it all, being everything to everyone. I was racing home after a volunteer committee meeting I didn’t really have the energy to attend after a full day of emails, calls, meetings, and parenting. Some ways into that trip back home down the dark road, I felt the car jolt, stop, then refuse to back up. Without even realizing it, I had driven off the road and lodged my car between two trees. As I came to discover soon after, I had been so tired and distracted I had been driving down a dark, foggy, rural road without my brights on and hadn’t even noticed.”

Being Looked Down On

Sarah Wall, Founder, XeraSupport: “As business owners, freelancers and entrepreneurs, women always face an extra challenge. They aren’t taken seriously. ‘Oh, you have a little business, that’s sweet!’ is a phrase I heard often in my early days. Most people – family, friends, men and women – didn’t believe I was actually working, that I made any money doing anything or that my business was anything more than a hobby. I would be asked to babysit, to go out for coffee or to go shopping in the middle of my workday. When I couldn’t, they’d get mad at me, or laugh and tell me to come out anyway, as it wasn’t like I had a ‘job.’”

Valerie Smith, Founder and CEO, Klei: “As someone who manufactures products here in the U.S., I have run into issues with old-school manufacturers and factory owners taking me seriously. I’ve been talked down to, man-splained to and dismissed. When I look to work with factories and suppliers, I’m placing an order for anywhere from 1,000 to 100,000 units. For someone to not take me seriously despite having grown my company organically, without any funding or loans, is extremely frustrating.”

Alexis Krystina C., CPA, Principal Accountant & Founder, Advance Accounting: “In the finance industry, what I’ve observed and experienced is that women have a harder time being taken seriously than men. I’ve personally experienced this because the branding for my company is pink, I have multiple tattoos and I’m a complete goofball. I initially felt that I needed to become someone else when I first entered the industry because who was going to take me seriously if I didn’t act ‘professional’ according to men’s standards. Men can talk and act in any way and not have to worry about being taken seriously.”

Donna Davis, Owner, Pro Video Talent: “When I first started, I had a male partner, and I would notice time and again that when clients met him, they immediately took it seriously that he needed to make money. With me, they would ask for me to ‘do them a favor,’ meaning do work for them at no cost. They never expected a man to work for free.”

Race and Gender

Ramona S. Chaplin, P.A., Owner and Lead Attorney, Law Offices of Ramona Chaplin: “Women face several challenges in the practice of law. Specifically, women of color may encounter prospective clients who believe success and competence are tied to looking a certain way (i.e. usually white and male.) Other prospective clients may attempt to pay female attorneys less than their male counterparts.”

Jantrice Johnson, CEO, MUKA: “As a female in the real estate business, I have always felt like it has been a man’s world. Coming into the business, I felt like I had to work twice as hard as my male counterparts. The struggle for me is being dominant but yet still feminine. I’ve had to learn to be aggressive but still be gentle, and that balance is difficult. I also struggle with the fact that I am a black female real estate agent, and I try to not come across as a black angry female. I want to go to war with the best of them, but I also don’t want to be labeled as angry while fighting for my clients or business.”

Self-Doubt and Imposter Syndrome

Mollie Newton, Founder & Editor, PetMeTwice: “I recently stumbled across two words that have helped change the way that I think of myself and my business – imposter syndrome. I was shocked to learn that 70% of people suffer from this and that women (as well as people from diverse backgrounds) were especially affected by this, as our internal doubt is mirrored by stereotypes in the world around us.”

Women in Male-Dominated Industries

Iryna Iuzhanina, Founder, Just Click Appliances: “As a female entrepreneur, one of the main challenges I face is that even now I meet people who are surprised to see a woman in a tech niche. There’s still this stigma in our society where people believe women should be bloggers.”

Jamie Klingman, Partner & Broker Realtor, The Klingman Group: “In business brokering, women absolutely face specific issues. This is a highly male-dominated industry. And in international deals, some buyers or sellers are from cultures where women aren’t allowed to do this kind of work. Being younger, and female, creates issues daily.”

Melanie Ocana, Co-Owner, Rustico Tile & Stone: “My industry is a male-driven industry – construction materials. While we sell directly to many homeowners, a vast amount of our clientele is flooring contractors, tile installers and builders. Our direct competitors are primarily male-run businesses. Imagine the change of pace when an established contractor or builder is getting advice from expertly trained women at our company. We’ve faced bumps in the road tackling some male egos.”

Gerianne DiPiano, Founder and CEO, FemmePharma: “Women are generally disregarded by the pharmaceutical industry once they are no longer in the reproductive stage of life. I’ve been in this industry for over 20 years and I have seen it on a personal level from male colleagues and big pharmaceutical companies. My experience ranges from personal harassment to noticing the lack of care and attention for women after a certain age by the industry as a whole.

Pressure from Traditional Gender Roles

Adina Kroll, Business Coach & Sales Expert: “Women have been traditionally praised for being ‘nurturing,’ ‘selfless’ and ‘putting others first,’ which are lovely qualities to have – but when it comes to creating financial independence for women, these can be in the way. Being humble, a good person and asking for money aren’t traditionally taught to belong together. Women tend to face issues of self-worth, people-pleasing and chronic undercharging, which is seen in the workplace and in self-employment.”

Marlene Quade, Co-Owner, Prime Mutual: “Society still values women in their role as caregivers over their role as breadwinners. As women strive to become economic powerhouses, they are often pressured to believe that their success will come at the expense of their spouse and children or their future family ambitions. Rather than choosing one over the other, women tend to take it all on, typically at the expense of their own well-being. Rather than using ‘downtime’ for self-care acts like sleeping or exercising, they’ll use this time to catch up on business demands or household obligations. Society has placed this gender inequality stressor on the shoulders of women, saying that we need to work harder to achieve a better work-life balance.”

Samantha Anderson, President and Co-Founder, Origin 63: “Studies show that women still shoulder a lot of the responsibilities of childcare at home. This is true for all women, but especially difficult for founders who are juggling the responsibility of running a company along with all the day-to-day (responsibilities) that comes with being a woman, spouse and mother.”

What about you? Are there challenges you’ve faced in your entrepreneurial journey that arose just because you are a woman? Share them with us below. You’ll be helping other female founders realize they aren’t alone.

About the author

Laura Grant

As Managing Editor of Lioness, Laura Grant works with the editorial team and a slew of freelancers and regular contributors to produce a publication that offers equal parts inspiration and information. Laura is a graduate of Western New England University with a bachelor’s degree in English Literature and a master's degree in Communications. She spent her undergraduate term developing her writing and communication skills through internships, tutoring and student media involvement. Her goal is to publish a novel one day. Before joining Lioness full-time, Laura was a freelancer herself and wrote many stories for the magazine.

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