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Women-Owned Small Businesses Share Challenges & Offer Tips on How to Overcome Them
by Dean L Swanson
March 31, 2022

Women Entrepreneurs and Small Business Owners Share the Challenges they have encountered and Offer Advice to those Just Starting

In my last business column, I urged more women to consider the opportunities of starting your own business.  Now I want to share what women CEOs have identified as some of their most prominent challenges that they have faced, and how they overcame them as reported by Brett Farmiloe, one of SCORE’s content partners.  He is also the Founder & CEO of Markitors, a digital marketing company that connects small businesses to customers through organic search. He enjoys converting insights from small business owners into high-quality articles for brands.  To help women entrepreneurs and small business owners overcome their challenges, he asked founders and CEOs this question for their best advice.  Here are some of what he found out.

Finding the Right Network

Audrey Hutnick, Smallwave Marketing shared this.  After hundreds of hours spent at various networking groups, I struggled as a woman to find a community where I felt I truly belonged. Time and again, I was told that I was too young and inexperienced or looked down upon because I was a woman networking in an older man's world. This challenge disappeared as soon as I found a group called Women Belong. Even the name told me I was in the right place. As soon as I tapped into a community with other strong and empowered female leaders, I knew I was in the right place!


Beryl Krinsky, B.Komplet reported this.  When I started B.Komplete, I was the one doing just about all of the content development, programming, and more. There would be times when I would work on one PowerPoint slide for hours until I realized that no one besides me would notice if the font were "exactly" the proper size or if the shade of the background was a little too bright. When I let go of the idea of perfectionism, I gained massive productivity and business growth. Perfect is boring! And one of my mantras now is, "good enough, move on."

Achieving a Work-life Balance

Alisha Taylor, Alisha Taylor Interiors responded.  As business leaders, it is often difficult to have a work-life balance. With the added responsibilities of being a wife, mom, and caregiver to our families, there is never enough time in the day. When it comes to business, you have to show up and do your best work every day and support your team in the process. Each day there is so much responsibility on our shoulders that we can't take for granted. While these roles and responsibilities are a blessing, they ultimately challenge our ability to find and maintain a work-life balance.

Fear of Failure

Vanessa Molica, The Lash Professional identified this.  Female entrepreneurs face much more scrutiny than males, preying on their confidence and amplifying the fear of failure. I believe a fear of failure is natural, but giving in to it is never an option for me. I have too much to do and too many goals to achieve to let this kind of fear paralyze me. Rather than let it rule me, I use my fear of failure as fuel for my continued success.

Don't Be Shy, Speak Up

Katie Lyon, Allegiance Flag Supply said this.  Being taken seriously is sometimes a challenge. I'm a blond, Southern woman, so I'm immediately stereotyped before I even utter a word. To overcome this challenge, I entered every business meeting and interviewed prepared. I know my company inside and out, and I'm not afraid to show my expertise. I don't believe you can be shy if you want to be a successful woman entrepreneur. You have to find your voice and speak up for yourself.

Working in a Male-dominated Industry

Saskia Ketz, Mojomox reflected this.  I was working at a tech startup with an overwhelming number of male employees, which occasionally brought in an unbalanced spirit. Meetings, communication, and the entire company culture are different when there's a lot of testosterone on the table. Sometimes that's fun to watch, but it's generally rather exhausting. I had the idea of building a women's group with two other ladies (four, actually, at that time). We mainly discussed our thoughts on how we could have a stronger voice in the company, for example, by bringing in female engineers and promoting more women to leadership positions.

Stereotypical Prejudice

Lisa Richards, The Candida Diet identified this.  Gender-based stereotypical prejudice, including my team, was one common challenge I faced at the initial stages of my entrepreneurship journey. In those early days, I quickly realized that some employees had a problem with a woman making all the decisions and telling them what to do. Such employees were also prone to misconstruing my intentions or actions and actively sabotaging my efforts. I had employees like this in my team who made the work environment toxic and ineffective. I had to let go of some of these staff members because they refused to change and be better. From this experience, I also learned how to identify and dismiss interviewees who would find it problematic to have a female employer if granted employment. This saved the rest of my staff and me the trouble of dealing with such people. As a result, we haven't experienced a problem of this kind since this initial experience.

The Loneliness of Being a Solopreneur

Leang Chung, Pelora Stack named this challenge.  This isn't limited to female small business owners only. Anyone starting as a solopreneur or operating as a company-of-one for many years understands this challenge. You don't have anyone to bounce ideas off of, someone to brainstorm on a new brand strategy, or someone you can turn to when something doesn't work out as planned. When I experienced this myself, I initiated three things to overcome this challenge. One, I joined different communities where I could connect with other solopreneurs. Two, I reached out to people I met within those communities to who I felt an instant connection to chat one-on-one and then set up regular check-in calls afterward to stay in touch. Three, I organized coworking events with other solopreneurs.

Lack of Respect for My Expertise and Experience

Georgia McBroom, Camper FAQS expressed this challenge.  One of the common challenges I face in my industry is the lack of respect for my expertise and experience. Clients are generally more inclined to consult my husband regarding our products and services despite having the same level of experience as him on the field.

Overcoming it was not easy, but working on my communication skills has greatly helped change our clients' views on my role in the company. Commanding the respect I deserve can be translated through clear and confident delivery of my knowledge and expertise in this industry.

Continue Showing Up

Jen Hope, Hey Jen Hope suggested this.  One of the most challenging parts of being a small business owner is staying the course. In 8 years of business ownership, I have found that the least glamorous part about making a business work is showing up every day and doing the work.

We know that consistent action in our vision is how we can get where we want to go. However, as a leader, you often have less external structure and accountability to hold you to your commitments by default. This usually means we have to be self-starting and very disciplined, even on the days we're not motivated.

Building a successful marketing strategy, client pipeline, sales process, cash flow system, product, etc., is all the result of showing up every day and doing the work that needs to be done. It's not glamorous, but it works.

I have the mindset to show up and do the work every day. That mantra keeps me on course to achieve my big dreams, one day at a time.

Bias, Bigotry, and Bullying

Sarah Ratekin, Happiness Is Courage shared these experiences.  These are all part of the same challenge. As a female small business owner, I frequently find myself dealing with people who still, in 2022, think I'm the admin. I've had people breeze past my introduction, hand me their card, and very brusquely say they'd love to speak with the owner. Not only is this incredibly ignorant on their part when women own 31% of small businesses, but if that's how you treat my admin, we won't be doing business. It bothers me that we have to incentivize people through diversity metrics to work with women business owners. Still, until the double standards evaporate (and this is true no matter what non-dominant groups you're a member of), it's sadly true that assumptions like this are alive and well. I overcome it by making it abundantly clear I am a woman-owned business on my website and other marketing materials. We don't necessarily need "Lady Boss" bumper stickers, but we need to represent our organizations as leaders proudly.


Alicia White, Project Petals shared one that many face.  A common challenge that I face is accessing funding. The money allocated to women-led founders is abysmal. The funding that is accessible to women of color is even worse. To gain the funding that I need to run my organization. I had to network, build relationships, and join communities that were not only supportive but offered resources.

About the author
Dean Swanson
Dean L Swanson
Dean is a Certified SCORE Mentor and former SCORE Chapter Chair, District Director, and Regional Vice President for the North West Region, and has developed and managed many businesses. The Rochester Post Bulletin publishes his weekly article on a topic geared toward the small business community. The articles here are printed in their entirety.
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