5 top struggles for women in business that we dont talk about enough

When I first started my business in 2004, I didnt participate in women-centric business groups or organizations. I firmly believed I would be hired because my work was great, it was priced competitively, and I could deliver a wide range of services.

I was wrong.

All Aboard the #StruggleBus:

A few years ago, maybe in 2012 or 2013 I hit a wall in my business. As a result of our rapid growth, our minimum project size grew from $5,000 to around $20,000 and I suddenly found myself competing against bigger firms, most owned by men who were not full-time parents. And I kept losing.


I saw women in womens tech and business Facebook groups refer male-owned competitors and never refer my firm.


I saw other business owners, with less experience than me, invited to speak.


As a member of the Chicago Chamber, I saw them host a panel of do good companies with all men and no B Corporations.


When introducing myself with a male friend who owns a similar agency to mine, another man in the room asked my friend about his business and then looked at me and said: So, you must work at home then.


Now, each of these instances by themselves are almost no big deal.They happen all the time! But when they happen consistently, added??up over 13 years of business, it means significant revenue and opportunity losses.

There are many obstacles you will face at some time in your career. But that doesnt mean you cant overcome them. Here are five big ones I experience on a regular basis and some thoughts on how to thrive when the odds are stacked against you:


#1 ??Your age will matter.

Both men and women will make assumptions about your level of experience because you are too old or too young.

What breaks that apart? A polished presentation. Most of the agism argument will come from how you present your knowledge, so work on those presentation skills. Do you apologize needlessly? Speak with vocal fry? Use crutch words like really um or so? Record yourself and eliminate them from your presentations. If you have the time and resources, work with a consultant who can help you refine your skills. I worked with Ita Olsen from Convey early in my career and it made all the difference in the world.


#2 ??People will make assumptions about your success.

To break this one apart, I like to have success-based talking points on hand. Recently, another woman challenged my qualifications??to lead a branding session and I had a list of relevant success stories on hand to list. I was able to mention several high profile clients and projects I had recently worked with. Prepare??your elevator pitch, a list of successes, names to drop, and other bits that confirm your success. Just being invited to the table isnt enough all the time, which is unfortunate but true. Practice, practice, practice.


#3 ??You will be judged on your appearance.

This is tough one for me, because in my experience it comes mostly from other women. People say dress for the job you want, and they are right. I regularly show up in jeans and our office is pretty casual. Being in tech and design, the rules are also a little more lax. But people have in their head a vision of what a leader should look like, for better or worse. Ive fought against this for a lot of my career, and Im just now realizing while doing a lot more politically ??that dressing for the role is more important than I ever thought.


#4 ??There arent enough women to pull you up.

If you are a woman in business, you must seek out and hire woman-owned companies. You must recommend them for speaking gigs. Connect them to resources, promoters, and promote their businesses yourself. Help build the network.

There arent enough women at the top to pull us up, so we have to pull each other up constantly.


#5 ??You will have to promote yourself constantly without looking like you are constantly promoting yourself.

Im terrible at self promotion, even having done a lot in my 20-year career. I’m regularly passed over for speaking gigs, even from women-run organizations, because I dont speak up enough. The squeaky wheel does get the grease and we have to be better at self promotion. With the plethora of channels available to us, in social media and online platforms, we just have to get out there.


Heres my (uncomfortable) list:

  • Ive run a successful business for 13 years
  • Ive helped MANY other businesses position, test, and launch
  • Ive mentored other business owners
  • I will be teaching at Columbia College in the fall
  • I regularly speak on business, leadership, UX, and branding
  • I also run a lobbying organization for womens rights in Illinois
  • I am a leader, a coach, an activist, and and activator
  • I am good at my job
  • I am powerful


All five of these issues are intertwined. You can promote yourself and other women at the same time. You can polish your pitch and your public appearance. When you know the established rules inside and out, you can write the rules for your own game. We can lift each other up.


If you try and do all of this yourself, as I did in the beginning, you have a much steeper hill to climb. But together, TOGETHER, we are stronger.


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