7 Women Entrepreneurs Share Their Biggest Challenges

By Saige Driver

Women entrepreneurs face challenges that men might never experience, let alone consider. Here’s how they leap over their unique hurdles.

• Women own 1 in every 5 American businesses – that’s 1.1 million businesses.
• Women entrepreneurs often face challenges in accessing funding, feeling respected as business owners, and building a support system.
• To overcome these challenges, women entrepreneurs often create their own support systems, overcome their insecurities, and reach out to other women entrepreneurs.
• This article is for women who own or want to start a business and are curious about how other women entrepreneurs face their unique challenges.

Being an entrepreneur isn’t easy. From cash flow problems and marketing woes to saving for retirement, business owners must overcome myriad obstacles to become successful. These challenges are especially notable for women, despite the increasing share of women-owned American businesses. 

We’ll explore some facts and figures about women-owned businesses in the U.S. and share tips from successful women entrepreneurs on how they overcame their unique challenges.

How many American businesses are women-owned?

were 1.1 million women-owned businesses as of 2019. This figure corresponds to women owning 1 in 5 businesses. These businesses employed 10.1 million people and earned $1.8 trillion in receipts. The SBA also notes that women-owned businesses grew at twice the rate of men-owned businesses from 2014 to 2016.

Did you know?: Between 2014 and 2016, American women-owned businesses grew by 6%. Concurrently, the number of American businesses owned by minority women grew by 14%.

What challenges do women entrepreneurs face?

Aside from the typical entrepreneurial pitfalls, the female business owners we interviewed cited several challenges women entrepreneurs face. These challenges include obtaining funding, growing a support network, and reckoning with feelings of inadequacy and the fear of failure. Some other difficulties are bucking social expectations, being seen and heard, and achieving a positive work-life balance. 

How women entrepreneurs can overcome their challenges

Women have made significant strides in the business world, but they still face obstacles that men don’t encounter as frequently. We talked to a few successful women entrepreneurs about the challenges they face and how they overcome them.

Making authoritative first impressions

“One of the biggest challenges women entrepreneurs face is creating an authoritative first impression. We are often stereotyped by our looks and not immediately recognized as serious entrepreneurs.”

The solution: “To overcome this challenge, I’ve started to introduce myself, my first and last name, and my business as I shake hands. ‘Hi there. Sarah Pendley, Sarah Theresa Communications.’ This establishes authority and immediately clears up any confusion as to my role. I’ve found that conversations go further, and I’m taken more seriously as an entrepreneur.”

– Sarah Pendley, founder of Sarah Theresa Communications

Achieving work-life balance

“As a mom of two and owner of three businesses, my greatest challenge as a female entrepreneur is finding balance. It can feel like your heart and your time are being tugged in a million different directions at once.”

The solution: “However, one thing that has helped me achieve the balance I’ve been craving is by creating schedules and systems.” 

– McKinzie Bean, founder of Moms Make Cents

Finding a support system

“As a mother, most of our personal friends have kids, and a large percentage stay at home – or, if they do work, they don’t have the same business risks and demands as an entrepreneur has. It is easy to feel like nobody feels like you do or has your struggles.”

The solution: “In this day and age, it is helpful to listen to podcasts, read books, and connect outside the geographic confines that may make you feel isolated. There are stories out there that can inspire you, and we all have days we need inspiration.” 

– Tara Youngblood, co-founder and chief scientist at ChiliSleep

Did you know?: Black women business owners are excelling in entrepreneurship. Women of color own more than 2 million businesses and are 4.5 times more likely to start a business.

Getting unsolicited advice

“Everyone and their cat want to give you advice on what to do, especially men and people who are not even remotely in the pit with you. I have been talked down to, not taken seriously, and even ridiculed.”

The solution: “The kindest way I have learned to tackle this is to be graceful and repeat a silent mantra in my head: ‘I am not here to prove anything to anyone. I release this thought from sticking to me or having the need to react to the comment. The people meant for you will understand and find you.’ And I smile and get on with my work because my energy is limited, and I need to show up every day.” 

– Neelam Tewar, founder of Maven Magpie Consulting

Being lonely

“The big thing I didn’t realize was that going from an office of 30, and a position where it was my job to build community, to being a solopreneur would result in feeling really lonely in my professional world. Even though I was meeting with clients and hosting one-on-one meetings, I couldn’t unload my concerns, questions, fears, and doubts on existing or potential clients.” 

The solution: “I started by reaching out to those I had met in the community through the local Chamber of Commerce Women in Business group, then went online to start scouring for other women in business-focused events, meetings, conferences, book clubs, etc.” 

– Christine Flynn, MSW, grant management analyst at Office of Illinois Works

Battling unrealistic expectations

“My crazy expectations were mostly from myself. I expected to be Super Mom, wife of the year, and build a successful business all in the same year. Even though I was (and am) doing great in all the key areas of life, I often felt inadequate, which is exhausting.” 

The solution: “I overcame this by starting a ‘what got done’ list and gauging my success by that, rather than looking at the items still on my to-do list. This one little shift has made a huge difference, and I let the guilt of not getting every single thing done go.” 

– Brie Sodano, personal financial strategist at From Sheep to Shark

Tip: Use an organization app to display what you’ve already crossed off your to-do list instead of fretting over what you still need to do. You’ll feel accomplished and less frantic.

Overcoming self-doubt

“I believe the biggest challenge female entrepreneurs face is their own self-doubt stemming from a past negative experience or relationship … Insecurity can get the best of some and lead to a less-than-supportive community of women. It is only when women support each other that can we squash our self-doubt, take a risk, and breathe 100% confidence into our new endeavor.”

The solution: “The first step to overcoming this challenge is to dig deep and identify the source of any insecurities. Why do you doubt yourself? These are the barriers to our success and cannot be overcome unless they are recognized, validated, and released.”