10 Entrepreneurial Chicago Women on How to Make It in the Windy City

You’ve got this amazing business idea, but you hate networking. Or maybe you have a gnawing sense you’d be happier in another field…but are worried about the money. Guess what? You’re not alone. We asked ten Chicago powerhouses in business and the arts for their advice on building brands, getting through tough days and (yes) networking.

5 Things Chicagoans Can’t Stop Talking About

alex covington chicago
Stacy Rupolo

Alex Covington, Brand Director At The Wing

What did you want to be when you grew up?
I grew up watching Michael Jordan soar, like so many other kids in Chicago, and I always told myself that I was going to be the first woman to play in the NBA. Sometimes your dreams (and your free throws) don’t line up with reality, but what they did do was lay the foundation for my attitude about my career. I made a habit of going after opportunities where I had to outreach people’s expectations of me. Whenever someone doubted me or told me no, I made it my business to make my mark and play my game. And if it didn’t work out, I made it work elsewhere. After eight years of working in advertising, I finally jumped ship to work for a brand that I truly believe in: The Wing, a woman owned and led company that allowed me to build my own path and team.

What’s one piece of advice that’s changed the way you work?
One of my first bosses, a legendary woman in PR, told me that I was in the business of PR, not ER. And while I’m not in PR anymore, it really helped put my relationship with my job into perspective. I’ve always been someone who works hard and who comes from a household that preached the words of “twice as good.” And while that phrase still rings true given the reality of working while Black in America, I realized that I could work hard but not at the expense of my livelihood. I had to prioritize my health, find the courage to say no and not see mistakes as failures but as opportunities to chart new paths forward. 

What’s your approach to networking?
My approach is to embrace the awkwardness and the unnaturalness of it all. Once you recognize that everyone is going through similar feelings of anxiety and hesitation, you can move past it and get to the best part of the process: where you actually connect with new people. That’s why I feel so passionate about the work we’re doing at The Wing. We are a community space physically designed for women to network and make meaningful connections with one another. We just opened in Chicago, and my mom [ed. note: pictured at right above] actually flew in to help us connect with local women and community leaders. I spent the week connecting with so many new women I wouldn’t have otherwise met, and I’ve always found that if you lead with authentic curiosity, the conversation just flows naturally from there.

monica royer chicago
Ponce Photography

Monica Royer, Founder & Ceo At Monica+andy

What’s one piece of advice that’s changed the way you work?
My mom told me, “Fail to prepare, and prepare to fail.” That has changed so much of the way that I work. I now realize that much of life as a CEO is about preparation. Whether that is at work or home. Especially as a mom, I realize if I build in time to prepare, everything runs so much more smoothly. This is still a work in progress, but it is truly helping me to evolve as a human being. In the early days of a startup you need to just do. As time goes on, you have data and teams, which means even more preparation is needed. 

What’s one challenge of working for yourself that no one ever tells you about?  
You are always working. When all the roads lead to you, there really is no downtime. If you really love what you do, as I feel about my work, it works out. However, with managing a team and all the texts and emails, the work is omnipresent. It is hard to carve out time away from it. I feel grateful that I enjoy it so much.

Where do you go for inspiration on tough days? 
I look to my family: my husband, parents, brother and sister-in-law—but most especially my daughter. The light in my 8-year-old is such a beautiful thing. To see the world and all the excitement she sees, even in the small things, is incredible. I also get a lot of positive energy and inspiration from my team. 

stacy ratner chicago
Eileen Molony

Stacy Ratner, Cofounder Of Chicago Literacy Alliance

What did you want to be when you grew up?
A copy editor or proofreader, because I was fascinated with how books are made and didn’t think I had the talent to be an author. Forty-something years later, I’m still happiest when what I’m working on involves books. 

What’s one challenge of working for yourself that no one ever tells you about?
The guilt. On great days (and there are so many of them), you wonder why you get to be so happy in your job when you know that millions of people are miserable in theirs. On bad ones (and there are even more of those), it’s easy to convince yourself that what is happening is all your fault and in your control, and that if you had just worked harder or differently, you could have produced a better outcome for the people depending on you.

Where do you go for inspiration on tough days?
Outside with my dog, into a library or down to the lake. If none of those are possible, a solid murder mystery works too.

halle borden chicago
Hallie Borden

Hallie Borden & Dana Karlov, Sisters & Co-owners Of Honey Bridal

What’s the biggest lesson you’ve learned in your career?
People can tell when you love what you do. We have fun at work, feel good about supporting creative women and take pride in the environment we create for our brides. That passion and contentment is contagious, and it resonates with our customers.

What’s your approach to networking?
Community over competition. We refer customers to our “competitors” all the time, and they give us that love right back! And we’re so over the traditional style of networking—we don’t want to exchange business cards, we want to talk about how we can collaborate. We’re so lucky in this business to be surrounded by talented women. Let’s get those creative juices flowing and work on a project together. 

What’s one piece of advice that’s changed the way you work?
Don’t procrastinate. Just don’t. Tackle things in order of importance and don’t let the to-do pile get too high.

courteney phillips chocago
Ashley Fischer

Courtney Phillips, Project Manager + Entrepreneur + Cofounder At Gumbo Media

What did you want to be when you grew up?
When I was younger, this question was always answered from a place of wanting to please others and make them proud. It wasn’t until my early twenties that I reflected on what I really wanted and cared about. In the time since, I’ve come to see myself as a curator. I’m a creative like others, but my expression isn’t the art itself, but the intention, execution and inclusion that push art forward. I’m most in my element when I’m creating community and space for others.

What’s one piece of advice that’s changed the way you work?
Don’t be afraid to fail. You have to be willing to put yourself out there. It’s often better to try, fail and pivot than it is to wait for everything to align. Perfectionism is dangerous in entrepreneurship. If you’re constantly waiting for the perfect moment or thought or concept, it may never come. You have to create it by doing the work, learning from it and improving based on experience. As soon as I learned this, I became happier and more productive and started enjoying the process of creation more than the expected end result.

What’s one challenge of working for yourself that no one ever tells you about?
Putting a price on my time and work. Not all projects are the same or have the same budget or value, so I prioritize what I want to work on and go from there. It’s obviously important to make money, but it’s also not the only factor. It’s a delicate balance between passion and security. Ultimately, the money will come to those whose energies align because it’s just an extension of our values in practice. But it doesn’t necessarily come by itself. At some point, we all have to learn to value our time and to ask for what we think that time and energy is worth publicly. It’s hard for many entrepreneurs to do this when starting out, especially for many women and people of color. It was for me. But I’m getting better at it.

katy lynch ulliott
Daniel Kelleghan

Katy Lynch Ulliott, Cofounder & Cmo Of Codeverse

What’s the biggest lesson you’ve learned in your career?
Stay focused. I’ve seen entrepreneurs fail because they deviated from their mission, got distracted by what their competitors were doing or didn’t follow their business model.

What’s one challenge of working for yourself that no one ever tells you about? 
That you have to be self-motivated every single day. Since there’s no one to tell you when to wake up, when to report to the office or when to finish writing or sending a contract, you—and only you—are responsible for making these things happen.

Where do you go for inspiration on tough days? 
Energy is contagious. I get inspired when I surround myself by what I call good energy. Whether that’s a concert or a food festival or SoulCycle, I am drawn to places that attract a lot of people having fun.

ziba sarabia lennox chicago
Frank Rocco

Ziba Sarabia Lennox, Co-owner Of Mazi Dance Fitness + Blogger At Dancing Mama Style

What’s the biggest lesson you’ve learned in your career?
Thanks to technology, today’s world can feel transactional, but relationships are everything. Respect, manners and genuine interest in others’ lives really matter. For MaZi Dance Fitness, we’ve had some relationships that are going on ten years. They mean everything. With Dancing Mama Style, I’ve realized that online relationships can be just as strong as IRL. There are people on Instagram I’ve never met that I am in touch with daily and are real friends.

Where do you go for inspiration on tough days?
Both of my businesses are all about self-expression, so the answer usually lies in getting back to work to figure stuff out. The studio is my happy pill: I can be having the worst day, and after teaching my class, I feel just fine. With the blog, it’s fulfilling when my followers message me about an outfit I helped them find or relate to something I shared about being a mom. When all fails, my boys are a grounding force that I cling to, because nothing matters more than hearing their giggles and getting tackled by their big bear hugs. I also pray and fiercely believe in miracles.

What did you want to be when you grew up?
I wanted to be a ballerina and in fashion. I resisted giving them my all because it made me nervous to love something so much. What if I failed? When I left my ballet company, the artistic director said that I would come back to dance because it’s what I truly loved. While in business school, I wasn’t very true to myself. I wanted to be a banker because I was good at math, and it sounded lucrative and exciting. After a couple of years of that, I realized that you can’t be good at something you don’t love even if you have the capacity to do it. That’s been a guiding light for me ever since: Don’t chase the money, chase the passion. If you put in the work and you would do it for free, the money will come.

jocelyn delk chicago
Ali Stone

Jocelyn Delk Adams, Founder Of Grandbaby Cakes

What did you want to be when you grew up?  
I wanted to be a cross between an attorney and a movie director.

What’s one piece of advice that’s changed the way you work?
I’ve heard more than once that exercising self-care is as important to your business as anything else. Doing so has helped me focus more in my professional life.

What’s one challenge of working for yourself that no one ever tells you about?  
Maintaining the proper mind-set is such a challenge. Staying self-motivated and changing your perspective from that of employee to owner is a huge challenge, but it’s so necessary to master for success as an entrepreneur.

sona jones
Courtesy of Sona Jones

Sona Jones, Coo Of Chicago Ideas

What’s an important lesson you learned recently? 
I’ve spent the past year working on getting better at living the serenity prayer, and it has changed how I approach work and life. In concert with that, I’ve been pushing myself and my team to get better at understanding the difference between an annoyance and a blocker. It changes everything when you start to view challenges through that prism.

Where do you go for inspiration on tough days?  
I listen to my young children talk and interact. I learn so much about human nature. But also, last night I snuck out of the house after they went to bed to buy myself an ice-cream sundae. 

What’s one piece of advice that’s changed the way you work? 
Don’t worry about whether they like you; worry about whether they think you’re effective. 

emily achler chicago
Courtesy of EMILY ACHLER

Emily Achler, Ceo & Cofounder Of Italic Type

Where do you go for inspiration on tough days?
On tough days (of which there are many) I go back to a comment I read once in an interview with Nora Ephron. She said, “It takes this huge amount of will and energy for anything to happen to you.” And on days when I struggle with motivation, direction or self-doubt, I revisit that quote. I remind myself that I have to apply sheer force of will, every ounce of scrappiness and all of my creative energy to bring my ambitions to life.

What’s your approach to networking?
My approach to networking is simple: I help others where and when I can. This karmic-centered approach means that I’m always happy to spend time taking a call or meeting with someone, taking a survey, voting in a contest, posting on social or whatever else I can do to help. I know that eventually I will need people to do the same for me, and so I hope by putting as much positive energy and helpful vibes into the universe as I can, some of that will ultimately come back to help me when I need it.

What’s an important lesson you learned recently?
One important lesson I’ve learned recently is something that isn’t often discussed in professional advice settings, but I think should be. I recently did the Whole30 diet, and among the things I learned was what it was like to attend professional happy hour events without consuming alcohol. I realized that if drinks were available somewhere, I’d probably have a couple glasses of wine without thinking too much about it. But it was actually a revelation to realize that it was a better experience to mix and mingle without drinking and maintain more clarity and less fogginess the next day. As a founder of an early-stage startup, I need to be my sharpest, most positive self as often as possible. Being more mindful of my alcohol consumption has been an important lesson.

Interviews have been edited and condensed for clarity.

amanda nyren

Writer, yogi, mom to about a dozen houseplants

A lifelong Chicago resident, Amanda started covering the local scene for PureWow in 2016. She's a freelance writer and content strategist.