Reflecting on the Challenges I’ve faced as a Woman Entrepreneur


by Katy Dwyer


Girl admiring a peaceful landscape by the sea feeling mindful

I’ve often referred to myself as an accidental entrepreneur.

When I was mapping out my life plan, my intention was to be a graphic designer. It was something that anyone, any business, anywhere might need, and I was good at it!

In my first real design agency position, I was given the opportunity to work directly with clients, and I found that I really liked that interaction. I worked my way up the ladder from Graphic Designer to Senior Designer, Art Director, Senior Art Director, and Creative Director. In 2008, the company I was working for was a niche real estate marketing firm, but that was not the year to be in real estate. I also happened to be on maternity leave after the birth of my first daughter. So, when the company I worked for asked me to come back part-time, I thankfully accepted, excited for this extra time with my newborn but worried, nonetheless, about our livelihood. There’s no better time to start a business than when you have a part-time job and a new baby, right?

Katy Dwyer Design started off as just a freelance business, a sole proprietorship. But over the course of the years, it grew into much more than that. Eventually, I found that I was able to bring in more work for myself than my part-time position offered me, and I took the leap and left the agency I worked for. I got busier and busier, eventually making the decision to move out of my attic and into office space so I could hire my first part-time employee. Making that decision to invest in my business was the catalyst for building what KDD Marketing is now. Once I started taking risks and putting money behind my business, we flourished and haven’t looked back since.

Enough about my backstory.

I’ve heard it said that women do business differently. I don’t entirely subscribe to that notion. Women must do business in the same marketplace as everyone else, therefore we can’t do business differently. Our goals are still to make a profit; we still must pay Uncle Sam, and we still have to follow the same general guidelines and laws around finance and HR and, payrolls and, banking, and so on. We may run our businesses with more compassion, flexibility, and respect, but the principles of business do not change because we are women.

But women do face different challenges in business, some of which I have experienced myself and others of which I’ve been a witness.

Minimizing Ourselves

The first challenge that I’d like to address is that as women, we have a tendency to minimize ourselves. And that affects us in business. This can come in so many different forms.

Imposter Syndrome is how I believe it shows up most for me. Regardless of all my successes as a business owner, I’m often in a room with more men and fewer women. I’m in an executive peer group which keeps me accountable, but currently, I’m one of the 2 female members of that group of 9. And since I’m an accidental entrepreneur, I didn’t get my MBA as part of my life plan, nor did I minor in business like my father always said I should… (you were right, dad!). So, it’s very easy for me to question: Do I belong here? What makes me think I can do this?

Other ways we minimize ourselves:

  • Self-doubt!
  • Fear of Failure!
  • Undervaluing ourselves!

As women, we are often shy about our accomplishments. We are afraid of being labeled as PROUD or BOASTFUL.

Men are called CONFIDENT. Women are called VAIN.

So how do women overcome this challenge? We need to build up our own confidence individually, and how we do that can be very personal. Some of the ways I work on this are:

  • Focusing on the positive and not the negative. If I focus on the bad in the day, week, or year, I will perpetuate all my self-doubt. But if I make an effort to look at the good that I have achieved, I am reminded that I am NOT an imposter.
  • Remembering that you can’t have SUCCESS without FAILURE. I look at some of my greatest failures as moments in time that led to my greatest successes, and that reminds me that it’s OK to fail. In fact, it’s only from failure that we can learn and grow.
  • Finally, sharing my challenges and accomplishments in this article is me challenging myself to be confident, acknowledge that I have achieved something, and not be shy about what I’ve built. Sometimes, simply putting your mind to doing the opposite of what comes naturally helps break down those barriers that keep you from growing.


Our Very Full Plates

The next challenge I have faced as a woman entrepreneur is that we tend to have too much on our plates.

Remember the story I told about my entrepreneurial journey? I had a job. I had a new baby. A husband. A house. I had plenty of responsibilities then, yet I decided to start a business. Throughout my career, those responsibilities have only grown. I have two daughters now, one in middle school and one in high school, and they have busy lives too. I’ve joined boards and school groups; I teach other entrepreneurs how to market their businesses. Oh, and I also run a business.

Finding a way to balance running a business and family life is challenging. Social and traditional restraints, like the assumption that women will be the primary caregivers for children, hold women back in the workforce. It is a challenge usually unique to women. As someone who works with clients, I have experienced this multiple times, where a female client calls to say they need to take a pause in their business or a pause in our work together or change their hours or services available because of a family crisis, a difficult pregnancy, or an aging parent. I have never had a male client call to say that.

As women, we tend to wear “busy” as a badge of honor. We may not be comfortable sharing our successes, but we have no problem basking in our multitasking abilities. We compete with other women based on our busy schedules… who had the busier day? Who has more on their plate? Who had a more mind-boggling taxi schedule for their kids over the weekend?

But that “trying to do it all” mentality is draining, and it really holds us back more than anything else.

As our careers and lives grow, we get better at multitasking and adding more to our plate, but what we should be getting better at is delegating. We need to recognize we can’t do it all ourselves.

Did you know, according to Global Entrepreneurship Monitor, women are more likely than men to start a business with ZERO employees?

For an entrepreneur, one solution comes in the form of hiring! That can mean hiring a new employee or an assistant or hiring a bookkeeper or lawyer or marketer to do the tasks that truly drain you in your business. Or maybe even hiring a babysitter, mother’s helper, or nanny. It’s true that you need to spend money to make money. And hiring is a great way to do that.


Underfunding Ourselves

Another challenge unique to women entrepreneurs is that women are underfunded.

Money can be a challenge for anyone in business. But statistics continue to show that women are underfunded. While I don’t have the solution to getting banks and investors to better fund women, I can speak to the fact that as women, we are sometimes responsible for underfunding ourselves.

Attempting to start and run a business while ignoring the need for money undercuts everything women in business are trying to prove. Trying to barter instead of spending, providing a service or product for less, or not investing in your business are some of the traps I often see women falling into. Talking about money, asking for more money, and sourcing money can be uncomfortable, but when you are in business, you need to overcome that.

Surrounding yourself with mentors and other people who have succeeded in your field is one way to keep yourself in check in this area. Leaning into other’s experiences can help make the idea of sourcing or spending money less uncomfortable.

Here are some of the things I remind myself of regularly:

  • Consider Raising Prices! Inflation affects everyone, and your business needs to keep up too. You shouldn’t be eating those increases.
  • You can’t grow a business without growing your expenses.
  • You have to spend money to make money. (I say this a lot)
  • Growth is Risky! There’s no reward without risk.


Unrealistic Expectations

The fourth challenge is that women have unrealistic expectations. These may be unrealistic expectations of ourselves (guilty!), unrealistic expectations of others (guilty!), or unrealistic expectations of our business.

The worst way I see this come through for me is the unrealistic expectation that as a woman, I can do it all, be it all, and I don’t need anyone. There was a time when I tried to be everything in my business. The bookkeeper, the admin, the salesperson, the designer, the IT person, and so on. I woke up early, got kids up and off to school, started my work day (didn’t leave my desk for 8 or 9 hours), picked kids up, fed them, bathed them, put them to bed, and sat back down to work until 1 am in the morning. All that led to was burnout and a business that basically stayed put. I wasn’t growing, I wasn’t earning more money, I was getting by.

I am also challenged to not have unrealistic expectations of others. I thought the best approach was to do it all myself and I believed that if I could do it all, so could everyone else.

Building a team has been a wonderful and rewarding experience for me and it has challenged me to change my expectations. I have learned in the process of cultivating my team:

  • how to hold space for others
  • how to relate to people who don’t work like you do
  • and how to set realistic expectations for them within the business.

Lastly, there are unrealistic expectations in business. For instance, if you believe you can do it all yourself, your business will grow exponentially, and you will be making six figures in a year without help from anyone, you are setting yourself up for failure! I’ve seen many women-owned businesses fail because of these unrealistic expectations.

Doing the work of building a business plan, running financials, setting a budget, and looking at your numbers monthly can go a long way to setting reasonable expectations and lead the way to real (and reasonable) business growth and success!

Those are four of the most challenging aspects of being a female entrepreneur that I’ve experienced in my journey. What am I missing? What challenges are you facing? I’d love to know!

There are many people to thank who have helped me overcome some of these challenges because I don’t do it alone. To my mentors, my peer group, Team KDD, and my family, thank you for being there for me and with me through this wild ride of entrepreneurship!


Katy Dwyer is the Founder & Creative Director of KDD Marketing. She started KDD in 2009 to bring her creative and marketing experience to hyper-local businesses. With 25 years of design and marketing experience, she is now proud to share both her talents and the talents of her team with many small- and medium-sized businesses in the tri-state area.