From Corporate Grind to Creative Freedom: Gretchen Reese’s Path from Side Hustle to Entrepreneurship
Have you ever wondered what turning your side hustle into a fulfilling career would be like? For Gretchen Reese, that wasn’t just a distant goal—it was a challenge she embraced and ultimately mastered. Over eight and a half years, her blog became the foundation of a thriving business. Gretchen’s journey of self-growth, persistence, and evolving priorities highlights how unwavering determination can transform your side hustle into a profession. Her story proves that with the right mindset, you have the power to shape the course of your career.
The Beginning
In 2015, while studying at the University of Wisconsin-Eau Claire, Gretchen started her blog, Monochrome Minimalist, as a creative outlet outside of her schoolwork. She wanted to create a platform to write about trends, coffee shops, and style. When I asked about her early inspiration, she shared:
“I’ve been a writer my entire life, but I first realized I wanted to do something in media—whether writing, photography, or being the creative force behind it—when I used to watch Project Runway with my mom. I remember thinking, ‘I want to have something to do with a billboard in Times Square. I want to look up and say, I did that.’ I didn’t know at the time if it would be writing, photography, or modeling, but I knew I wanted to express creativity that way.”
After studying abroad in the UK, Gretchen expanded her blog to cover travel, wine, and fashion. I asked if there was a moment when she realized her side hustle could be her career, she responded:
“It was when I was getting involved with traveling and writing about it. It came so easily—especially the photography. It felt like breathing, like something that fit without question. When you get that feeling, it’s hard to let it go.”
Transition from School to Career
Like many recent graduates, Gretchen felt the pressure to take a corporate marketing job after college despite knowing it wasn’t her true passion. Yet still, she never abandoned her blog, running it on the side while balancing her corporate responsibilities. Her job allowed her to travel, and during these trips, she developed a more profound knowledge of how to connect with different audiences, which showed in her writing. Always proactive, Gretchen also began pitching new ideas to her boss- one of which, a podcast, became a huge success. As she put it:
“I told my boss, ‘I could talk your ear off all day or start a podcast.’ My goal was to bridge the gap between newbies and seasoned professionals in the industry, because I was learning it too.”
Although her podcast was industry-specific, it reinforced her belief in the power of meaningful connections. She found joy in expanding her reach and knew these skills would serve her well in the future.
Corporate Life to Full-Time Entrepreneur
After a few years in her corporate job, Gretchen felt stuck but was hesitant to leave behind the stability it provided. It wasn’t until she was laid off that she embraced the opportunity to fully commit to being her own boss. “I knew I didn’t want to return to corporate life,” she said. “It was hard to leave, but I never looked back. I didn’t want to work for someone else’s dream that I wasn’t passionate about”. At this point, she had already built a strong portfolio, giving her the confidence to pursue her creative passions full-time.
Reflecting on her time in corporate, Gretchen appreciates the lessons and skills it taught her, particularly in confidence and mentorship. “I wouldn’t have had the confidence to pitch myself or understand my ‘why’ if I hadn’t gone through it [the job]. I also learned to speak on stage in front of 100s of people as well as the importance of mentorship and teaching others,” she reflects.
Her advice to anyone wanting to follow a similar path? “Figure out your ‘why,’ and remember that it’s allowed to change. If your dream job doesn’t let you live your dream life, it’s not your dream job. Don’t be afraid to start over, fail, or try new things.”
Gretchen’s ‘why’ changed in her late twenties when a close friend’s father fell ill. The realization that life could change instantly prompted her to reevaluate her priorities and rethink how she approached her work. “I realized I don’t want to miss out on life or say no to something because I had to work,” she explained.
Shifted Purpose
With this new approach to her work, Gretchen focuses on projects that align with her values and bring genuine joy. When I asked her what success means to her now compared to when she first started, she told me, “Back then, success was about how much money I could make or how many places I could travel to. I focused a lot on external validation. Now, success is about what feels most aligned- what makes me feel giddy. For example, does it feel like a struggle to make it work, or does it flow without resistance? Time and freedom are also a big factor for me- not having to constantly trade my time for money but having the flexibility to live my life the way I want, without being bound to a schedule.”
These Days
Since she transitioned to full-time self-employment, I asked Gretchen how her relationship with her passion has evolved now that her side hustle has become her career. She explained: “I’ve had to put better boundaries on it. I used to work at all hours of the night on my blog, but now that it’s part of my job, I have to set clear boundaries between work and play”. Still, she emphasizes that “staying connected to the joy means sometimes just grabbing my camera or writing for myself; not everything has to be published.”
These days, Gretchen’s blog has since evolved from niche content into a personal brand with infinite possibilities. She is focused on growing her community, traveling to new places, and coaching others. She also plans to relaunch her podcast, Passione!
When asked what she loves most about her work now, she said, “Connection! I want to connect with people passionate about their work, whether it’s a small cheese shop in Italy or a family-run winery. It’s about the connection that’s been passed down for generations”.
In Reflection
Gretchen’s journey—from a college blog to a personal brand built around her love for fashion, travel, and food—inspires me in many ways. As a longtime childhood friend, I also see her as a mentor. She’s shown me how to build a career around what you value while emphasizing the importance of flexibility, persistence, and finding joy in the process. Our conversation reminded me that turning your passion into your profession isn’t about following a linear path but about being able to navigate unexpected turns and discovering new possibilities along the way. But for Gretchen and so many other entrepreneurs, they wouldn’t have it any other way. In this way, I feel confident that her story will resonate with anyone looking to turn their side hustle into a full-fledged career.
About Gretchen:
Gretchen is a travel writer and online educator based between Puglia, Italy and Minnesota. She has been featured in Cohley, Travel Age West and Wild Bum. Sign up for her weekly travel stories and tips via her website.
