Alright – so today we’ve got the honor of introducing you to Jess Roe. We think you’ll enjoy our conversation, we’ve shared it below.

Hi Jess, thanks for joining us today. Let’s kick things off with your mission – what is it and what’s the story behind why it’s your mission?

When I started my blog back in 2018, my mission wasn’t just about creating an outlet for myself as a new mom—it was about building a genuine community. I wanted to connect with and uplift other parents, not just grow a following. Parenting is often portrayed as a beautiful journey filled with support, but in reality, it can feel incredibly isolating. It’s in that gap between expectation and experience where the real challenges lie—the exhaustion, the emotional weight, the unspoken truths of parenthood.

When I lost my full-time corporate content job at the start of the pandemic, this mission became even more important. It was a pivotal moment—transitioning into a self-employed creator reaffirmed my purpose with “The Windy City Mama.” I realized that so many other parents were navigating similar challenges, seeking the comfort and encouragement that my platform offered. This understanding fueled my passion and propelled me forward.

It’s what inspired me to keep growing my community and ultimately led me to launch a social media agency dedicated to supporting small, local, inclusive, women/lgbtq+/nonbinary-owned businesses. It’s also what drove me to take on the adventure of running a coffee shop—all with the knowledge that my work was making a real difference, even if it was just to one person reading my blog or following me on Instagram.

My journey has always been about more than content creation—it’s about connection, support, and creating a space where parents can feel seen and understood. It’s about sharing the raw, authentic moments of parenthood and building a community that celebrates every part of that journey.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m Jess Roe, the creator behind The Windy City Mama and the owner of Windy City Mama Creative, a boutique content creation and social media agency dedicated to helping small, local, inclusive, and women/lgbtq+/nonbinary-owned businesses thrive online. I also run a Chicago-based coffee shop, adding another layer to my deep love for community building.

My journey into organic content creation and social media marketing initially started while I was in college. I received my Bachelors Degree in English with a concentration in creative writing from the University of Iowa in 2015. During that time, I did multiple internships focused on social media content, including an internship with the Iowa City UNESCO City of Literature. This was right at the peak of Instagram coming on the scene as the trendy social media platform. I continued working in content creation (journalism and website content) during my first two jobs after graduation while staying up-to-date on social media.

In 2018, I launched my blog and related social media pages as a personal outlet. As a new mom, I was searching for a space to share the realities of parenthood—beyond the picture-perfect narratives often seen online. I wanted to create a space where parents could feel seen, understood, and supported. What started as a small passion project quickly grew into something bigger: a community of parents navigating the highs and lows of raising kids while also trying to maintain a sense of self.

Then, in early 2020, everything changed. Like so many others, I lost my full-time job in corporate content creation and account management due to the pandemic. But rather than letting that setback define me, I used it as an opportunity to build something even more meaningful. I leaned into what I loved most—storytelling, connection, and digital strategy—and turned Windy City Mama into more than just a blog. It became a full-fledged brand, and eventually, a business that helps other small brands succeed.

What I Do & Who I Help

Through Windy City Mama Creative, I provide social media management, content creation, and digital strategy services for local businesses—especially those run by women and lgbtq+/nonbinary entrepreneurs. I know firsthand how overwhelming social media can be, especially when you’re trying to run a business. My goal is to take that burden off my clients so they can focus on what they do best. Whether it’s crafting engaging social media content, building a brand identity, or creating strategies that turn followers into loyal customers, I help small businesses grow in an organic, authentic, and sustainable way.

Beyond my work in content marketing, I also run a coffee shop in Chicago, another passion-driven venture rooted in community. Coffee shops have always been more than just places to grab a latte—they’re gathering spaces where stories are shared, ideas are born, and relationships are built. Owning one allows me to bring my love for community-building into a physical space, creating a welcoming and inclusive spot for locals to connect and belong.

What Sets Me Apart

There are plenty of content creators and marketing professionals out there, but what makes me different is the heart behind my work. I’m not just about numbers, trends, or surface-level engagement—I’m about real connections. I approach every piece of content, every campaign, and every project with the same mindset I had when I first started my blog: How can this make someone feel less alone? How can this provide real value?

I also understand the unique challenges of balancing business and motherhood because I live it every day. I know what it’s like to juggle a million responsibilities, to put everything into a passion project while raising kids, and to navigate the messy, beautiful reality of being a parent, partner, and an entrepreneur. That perspective allows me to approach my work with empathy, creativity, and a deep understanding of what my clients and followers need.

What I’m Most Proud Of

Looking back, I’m most proud of the community I’ve built—both online and in real life. Whether it’s the parents who have found comfort in my content, the small business owners who have gained confidence in their marketing, or the customers who feel at home in my coffee shop, every connection means the world to me.

I’m also proud of the way I’ve grown my business on my own terms. I didn’t follow a traditional path. I pivoted, I took risks, and I built something from the ground up that aligns with my values. That’s something I hope inspires others—especially other moms—to chase their own goals, even if the road isn’t linear.

What I Want You to Know

If you’re new here, here’s what I want you to know:
– The Windy City Mama is more than just a brand—it’s a community. Whether you’re here for parenting content, Chicago recommendations, small business insights, or just a place to feel seen, you’re welcome here.
– My social media agency is built on a passion for helping small businesses succeed in an authentic way. If you’re a local business owner looking for digital marketing support, I’d love to help.
– My coffee shop is an extension of everything I believe in—community, connection, and creating spaces where people feel like they belong. If you’re in Chicago, come by and say hi!

At the heart of it all, my work is about storytelling, connection, and helping others thrive. I’m so grateful for every person who’s been part of this journey, and I can’t wait to see where it goes next.

Any insights you can share with us about how you built up your social media presence?

Building my audience on social media was a mix of passion, strategy, and a lot of trial and error. I started by focusing on what I genuinely love—Chicago, family life, and sharing unique experiences. I wanted to create content that felt both authentic and valuable, whether it was highlighting hidden gems in the city, sharing relatable mom moments, or offering practical lifestyle tips.

One of the biggest turning points was developing a consistent posting strategy. Instead of just sharing randomly, I created a content plan that balanced Chicago-based recommendations with glimpses into my everyday life. I also prioritized engagement—responding to comments, connecting with other creators, and truly building a community rather than just chasing numbers.

For those just starting, my advice is to find your unique angle and stick to it. The social media space is crowded, but your personal voice and perspective will set you apart. Stay consistent—even when growth feels slow, keep showing up. And most importantly, engage with your audience. Social media is a two-way conversation, and the more you connect, the more people will invest in your journey.

It’s not about overnight success—it’s about showing up, refining your content, and building something that genuinely resonates. Stay patient, stay authentic, and the growth will come

We’d love to hear the story of how you turned a side-hustle into a something much bigger.

Yes! What started as a side hustle eventually became my full-time career, and it’s been an incredible journey.

I originally began creating my own organic content as a creative outlet after having my first child—sharing my experiences as a mom in Chicago, exploring the city, and offering recommendations for places to go and things to do. At the time, I was balancing it with my full-time job in corporate content creation and managing, so it was something I did on the side, purely out of passion. But after losing my corporate job during the pandemic, I knew it was time to become more intentional with my content—developing a strategy, posting consistently, and engaging with my audience—I started to see real growth.

A major turning point was when brands began reaching out for partnerships. At first, it was small collaborations, but over time, I started working with bigger companies that aligned with my values and audience. Another big milestone was launching Windy City Mama Creative, which allowed me to officially turn content creation into a business, offering not just my own social media presence but also services for brands looking to grow their digital presence. This also led me to the opportunity to start running my own coffee shop.

Scaling up wasn’t instant—it took a lot of refining my approach, investing in learning, and treating it like a business rather than just a hobby. The biggest lesson I’ve learned is that consistency and authenticity are key. If you show up regularly and provide value, people will connect with your content.

For anyone looking to turn their side hustle into a full-time career, my advice is to start with what you love, stay patient, and be open to evolving as you grow. It takes time, but if you’re passionate and strategic, it’s absolutely possible to turn it into something bigger than you imagined!

Contact Info:

• Website: https://Thewindycitymama.com
• Instagram: https://instagram.com/thewindycitymama
• Linkedin: https://Linkedin.com/in/jessicaeroe
• Other: Pinterest: @thewindycitymama
  TikTok: @thewindycitymama

Image Credits

Jessica Roe