We were lucky to catch up with Kendra Cherrington recently and have shared our conversation below.

Kendra, looking forward to hearing all of your stories today. We’d love to hear the backstory behind a risk you’ve taken – whether big or small, walk us through what it was like and how it ultimately turned out.

Betting on myself and choosing to build a business while supporting my husband through medical school and raising three kids has been the riskiest and craziest thing I’ve ever done! Most people don’t realize just how heavy that season is (financially, emotionally, mentally, and even physically). Medical training is all-consuming. There are stretches where it feels like I am doing life alone, carrying the weight of our home, our kids, and our future. It’s almost an unspoken rule that if your spouse/partner is in medical school or residency, your own dreams go on pause. You don’t have the time, the support, or the financial margin. In our case, we were living on loans, relying on food stamps, and every dollar had to stretch farther than it should have.

For about three years, I sat in that tension — wanting something of my own but feeling guilty for even imagining it. After postpartum depression and anxiety with my third child, I realized I needed something that fulfilled me again. My husband had been encouraging me to sell my art, and friends had been asking for custom drawings and logos for years, so I finally listened. In 2021, I opened my Etsy sticker shop from my bedroom floor with borrowed tools: my husband’s medical school iPad, a TV tray, and a Cricut machine I’d gotten for Christmas.

Because we didn’t have the means for big investments, I built slowly and scrappily. Every dollar the shop made went right back into the business: better paper, bulk supplies, a desk, a chair. When I finally felt ready to upgrade to my own iPad, I didn’t have the money, so I opened a small business credit line and prayed I’d be able to pay it off. It took years to break even with the important investments I knew I needed to take, but I kept showing up.
By 2023, a business coach nudged me into brand design. Something that, in hindsight, had been calling me all along. I had rebranded my sticker shop three times, not because it needed it, but because I loved the process. That nudge unlocked a path I never even imagined. Now, in 2025, I own a small design agency and have designed and strategized for over 100 businesses. I get to help women exactly like I was, build brands that support their life’s dreams.

That original risk of opening a sticker shop with borrowed tools, zero safety net, and a whole lot of hope… became the catalyst that changed everything. It has allowed me to support my family through an intense medical school journey while building a career rooted in the things I love most: creativity, psychology, and helping other women step into their own next level.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I went from ‘Etsy shop sticker maker’ to ‘Brand Designer and Agency Owner’ in the span of 4 years! I know firsthand how hard it is to balance product creation and child-rearing, and making it all happen in the little moments between toddler nap times, snack times, and soccer games.

Now, I am the founder and brand designer behind Covarra Studio™. A laidback luxury brand studio that helps product-based businesses embody the credibility and connection their products deserve.

What sets my approach apart is the mix of high-end design with psychology, all shaped by my own experience as a product business owner. Brand is what deeply connects a business to its customers. My goal is not designing something that only looks the part but one that *feels* true to the experience brands want their customers to have. It’s very common for my clients to cry happy tears when they see the reveal because I took a feeling they couldn’t fully articulate and turned it into a reality (something they weren’t sure was even possible). My goal is always to make the rebrand process feel like a vacation— refreshing, but most importantly, completely transformative.

I am most proud of the ripple effect my work has in other people’s lives. My clients’ wins feel like mine too! Seeing their products stocked in major retailers around the world, featured in news or magazines, or shared proudly in gift guides is incredible. But it’s even more than the monetary wins too. I’m proud of creating a space where women feel, not only supported, but seen in their entrepreneurial journeys.

At its core, I created Covarra to be an experience. I want every woman founder who works with me to feel like she’s finally found her creative home where someone gets her vision. A place where strategy meets soul, luxury feels like ease, and growth finally feels like a “when” and not an “if”.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

My business journey has been full of juggling motherhood, medicine, and entrepreneurship without a roadmap.

Every successful person has a crossroad; a difficult season of pressure that either makes them give up or pushes them forward with a rekindled passion. Summer of 2024 was that season for me. My husband had just started residency, which meant uprooting our family from a life and friends we loved for his three-year residency in emergency medicine.

During that move, I had to pause my bookings so I could focus on settling my family in a very new area. That pause led to a pretty significant lull in business for a few months. I was overwhelmed, unsure how we would make ends meet, and facing a choice I didn’t want to make: between doing what I loved or doing what felt “safe”.

Random to me at the time, my sister called to invite me to be her plus-one on an all-inclusive (and free!) work trip to Puerto Rico. By some miracle, my husband would actually be home for the kids, which meant I could say “yes!” to the first real vacation I’d had in nine years. What I thought would be just a sister getaway ended up being a reawakening of my creative flow and the philosophical blueprint for Covarra.

The term ‘solo-preneur’ is romanticized to the point of burnout. I believed I could do everything alone for far longer than was healthy. The truth is, no one builds a successful business in isolation. It’s not sustainable to wear all the hats and expect growth. The answer wasn’t working harder; it was working smarter, with support and more brain power than just my own. Somewhere between the quiet mornings, the turquoise water, and business brainstorming over piña coladas, I realized that if I wanted Covarra to succeed, I had to stop trying to do it all myself. Business — like a good vacation — is better with company!

When I got home, I put every one of those realizations into action. I networked intentionally because my business depended on it, and so did my family. The connections I made that year became invaluable. They propelled me forward faster than I ever imagined, and they’re a constant reminder that success is less about pushing through the difficulties and more about letting yourself be supported.

Let’s talk about resilience next – do you have a story you can share with us?

Resilience, for me, is about learning when to wade, when to float, and when to ride the wave. Every business has fast and slow seasons, and what they choose to do with them is what actually determines their success. When I first transitioned into building Covarra, I was in a season where passion and pressure lived side by side. I loved the craft deeply, but there were times when the weight of responsibility (being a mom, homemaker, breadwinner, and wife) made me question whether I could keep going. But to me, quitting wasn’t even an option. Not because I’m fearless, but because choosing another path would have meant walking away from the very thing that would change our lives and the lives of people I wanted to serve.

I can now appreciate the slow seasons of pivoting. Instead of treating them as proof that I had ‘failed’, I learned to use them as an advantage. Whether that was a chance to refine my process, elevate my skills, or build systems that would help me scale and support the growth I was working towards. Most people back down when things get quiet, but that’s where I double down and step inward. Yes, there were doubts, but I never allowed myself to live there. Even when everything felt uncertain, I trusted that I could rebuild or reimagine, and that belief has carried me through every wave since.

Contact Info:

• Website: https://covarrastudio.com
• Instagram: https://www.instagram.com/covarrastudio/

Image Credits

BreakRoom Marketing