Rediscovering My Roots & Embracing Authenticity: What Women’s Entrepreneurship Means to Me

With Women’s Entrepreneurship Day this month (November 19th), I reflect on my time as an entrepreneur. I technically filed for my EIN in 2009, but my entrepreneurial spirit has burned for as long as I can remember. It felt like I was born to be in business. My mom recounts when I was a quirky little toddler, I approached family members, looked them earnestly in the eye, shook their hands, and said, “Thank you for the business.”

Growing up, I was a serial entrepreneur with several business ideas at every stage of my life:

Water delivery via empty Kool-Aid Bursts bottles to my family in our Southside Chicago home; drawing, assembling, and selling my own flipbooks to classmates in elementary school; crafting and selling origami one-dollar rings for kids in middle school; selling pencil portraits of classmates in junior high; and writing, designing, and drawing my own self-published newspaper that contained the latest family tea. (Fortunately, this garnered more amused giggles than actual controversy.)

I constantly sought opportunities for creativity and commerce.

There was something majorly appealing about the process of creating a concept from scratch and then working to deliver that product or service to others.

I kept that spark alive until school got too busy in high school and college. Then, societal pressure* forged a new, more settled goal. A sensible goal: Becoming a salaried professional. At a place. Any place. Preferably, in a big downtown building like an adult in the movies.

*”Wake up, you need to make money.”

twenty one pilots

So that was the mission. Although I was freelancing as a graphic designer here and there in college, the sole purpose of my time was to prepare for my updated dream of becoming an advertising art director in Chicago’s brightest advertising agencies. So, years later, satisfied with my post-graduate role as a budding art director at a Chicago agency (I did it, yay!), I happily filed away my entrepreneurial days under, “PAST.” No business management for me, thanks!

Now that I had achieved my goal and someone else provided my salary and health insurance, all I had to worry about was showing up at the office every morning and doing my work like a proper, responsible cog.

Then, the 2008 financial crisis hit. Every week that Spring, it felt like my colleagues and I got word of another agency closing its doors. We felt the fear. And every day, we felt the spirit draining from the walls until finally, I found myself walking the streets of River North with a cardboard box.

This wasn’t supposed to happen. I was supposed to start and end my career at a COMPANY—someone else’s company, not mine.

And all throughout college, the biggest fear my mom had for me was that I was going to be a [GASP] FREELANCER. I reassured her that my plan was to secure an illustrious position as a salaried professional. And here I was, a freelancer. [Pearl-clutching gasp!] Worse, a full-time freelancer. [More gasps!] Yes. It was my own, personal F-word.

I hope my facetiousness comes across here. Because my intention is not to disregard or disrespect freelancers or the concept of freelancing. This is merely a commentary on my own initial personal goal of fulfilling my dreams (and yes, my parents’ dreams) of “making it” as a salaried professional and then that ultimately not coming to be. But as my mom always said, “When one door closes, another door, usually a better one, opens.”

“When one door closes, another door, usually a better one, opens.”

Lina Flor Arellano

It makes me chuckle recounting the dramatics of this now, but at that time, the fear of the unknown was visceral. When you think your life will unfold in a very specific and prescribed way and when you’ve been indoctrinated to the belief that the only correct path in life was to report to a BOSS at an OFFICE, I felt like I had failed. The gaping void that was the uncertainty of tomorrow left me scared.

After I took a few weeks to wallow, I then realized that what was scary was also thrilling.

I shifted my perspective. And I rediscovered my natural-born instinct for entrepreneurship.

Entrepreneurship was—IS—in my blood. Both sets of grandparents owned and ran their own businesses and raised their families with their legacies.

I was always meant to run my own business! Those early, quirky years of shaking hands saying, “Thank you for the business,” was not only precociousness, but it was practice!

I found myself relishing the open canvas of the full-time freelancer life. I could wake up when I wanted! I didn’t have to commute! I could pick my clients! I could set my rate! But it took me years to dial in my routine. (For one thing, I quickly learned waking up at 11am was not a great long-term solution.)

I had a lot to learn about a lot. And I am ever-learning still.

For one thing, I have stopped seeing myself as a freelancer but as a business.

“I’m not a businessman; I’m BUSINESS, man!”


Today, I find myself 13 years deep into official entrepreneurship, and I love it. When I involuntarily stumbled into my long-term entrepreneurial path, I thought, “If this freelance thing doesn’t work out, I can always get a job.” But that backup plan ended for me about 10 years ago.

Now, I wouldn’t have it any other way. In fact, I have since started another business, Font Infusions, in addition to Brim Branding.

As an entrepreneur, I set my own terms. I draw my own boundaries.

And that’s what I love about women’s entrepreneurship, specifically. There may be guides or models, but there is no hardline blueprint for running your own business as, not just a woman, but as a human.

We can embrace the fluidity of reality vs. being locked within the rigid molds of outdated, patriarchal structures.

Capitalism was originally built under a patriarchal system. Although there are still many inequities to fight, now, the structure is more elastic, and even more in our post-lockdown world. There is room to earn a living on your own terms while accommodating your family and your dreams.

We can do business and care for our families and our bodies and our minds without silencing our authentic selves.

I write this while acknowledging my privilege. Not all people and not all industries allow for flexible schedules. But I also acknowledge that there now exists the permission to have all of your life roles be visible to the other people in the other parts of your life.

There is no longer a societal pressure to compartmentalize and to silence and to separate.

In my early agency days and even for many of the first few years of having my own business, I quickly picked up on the unspoken rule that talking about your personal life should be kept to a minimum. There was no room for personal needs or boundaries. That meeting time doesn’t work for you? Make it work. Do you have a little sniffle? Unless you have a fever, you can report to the office. Our hours are 9am to 5pm, but can you come in earlier and stay longer? Great, because that’s what the rest of us are doing. And there was no room for schedule fluidity for family or self-needs.

Today, I feel honored to serve an impressive roster of clients who are women entrepreneurs.

And they emerge from different backgrounds. In addition to being business owners, they are mothers, grandmothers, wives, partners, caretakers, political activists, community and sustainability leaders, tastemakers, industry innovators, and more.

We all understand that we might not get to that email ASAP. Or that we have to reschedule that meeting. But it doesn’t mean we don’t value their business.

It means we understand what it means to be an entrepreneur in today’s unpredictable world, and we make room for the messiness.

We are business owners. And we are also human. We can be vulnerable. We can trust. We can look to one another for support and laugh with a wink and knowing understanding. We can voice our needs and set our terms. And when we seal that deal, we can look into each other’s eyes and say with love and openness, “Thank you for your business.”

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