We’re excited to introduce you to the always interesting and insightful Kelsey O’toole. We hope you’ll enjoy our conversation with Kelsey below.
Hi Kelsey , thanks for joining us today. We love asking folks what they would do differently if they were starting today – how they would speed up the process, etc. We’d love to hear how you would set everything up if you were to start from step 1 today.
I would start earlier! It wasn’t until I turned 30 that I allowed myself to fully embrace my creative side and think beyond traditional paths. Before that, I wove small creative moments into my work. When Connecticut Kelsey came to life, I began challenging myself to think boldly, inspire others to explore new possibilities, and serve as a resource for Connecticut’s movers and shakers. Looking back, I can’t help but wonder how much further I could have gone if I had embraced this mindset sooner.
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
I’m Kelsey O’Toole, the creative mind behind Connecticut Kelsey—a platform dedicated to celebrating all things local and connecting our communities. My journey here has been anything but linear. I started as a classroom teacher and later moved into a corporate role, but I always felt pulled toward something more. I found inspiration in the people building businesses and lives they envisioned for themselves. You could say I was a “maker groupie,” following market and pop-up schedules, swooning over product launches, and cheering on their success stories. Eventually, I embraced my passions and built a space to collect and connect all my local loves.
Connecticut Kelsey offers endless candor and collaboration. In short, I collect and connect Connecticut’s makers and bakers with the movers, shakers, and adventure takers. My work involves finding, following, and supporting local creatives through markets and adventures, and then sharing those discoveries with my community through social media, conversations, and creative events. Here’s a peek at the kinds of questions I love getting—and answering—from my community:
Q: “Where can I take my little out for a fun birthday brunch today?”
A: “Ooo! A new restaurant opened in Stratford. They serve early brunch and have heated outdoor igloos!”
Q: “I just finished the semester and want to take the girls out on an adventure. Where to?”
A: “I just planned an amazing day in Old Wethersfield—here’s the agenda, boo!”
Q: “A customer just approached me for a bulk wedding buy. How should I handle it?”
A: “Take a deep breath and figure out how YOU want this opportunity to work for your business.”
Q: “I’m visiting [town] next weekend. What can I add to the agenda for fun?”
A: “Please hold—I’ll do some recon!”
Q: “I’m planning a [theme] party. Who can I use for cookies?”
A: “Here are my cookie girls!”
The positive feedback I’ve received has been incredibly rewarding:
“This is the first year I’ve made an income off my passion. Thank you for all the connections.”
“What’s the next project you’re planning? I want in!”
“You’re ready to go legit—you bring so much value to the maker community.”
“You always have a person.”
What sets me apart is my ability to infuse a sense of adventure and wonder into everything I do. I don’t just provide services—I create opportunities for people to connect, grow, and discover something new, whether through community events, collaborative projects, or tailored solutions.
I’m most proud of the relationships I’ve built along the way. Seeing people walk away inspired or with a renewed sense of possibility is what drives me. For potential clients and followers, I want them to know that Connecticut Kelsey is more than a brand—it’s a community. It’s a space where creativity and connection come alive, and I’m committed to helping every person feel seen, supported, and inspired.
How’d you build such a strong reputation within your market?
I believe my reputation was built on authenticity and connection. From the start, I’ve approached my work with genuine enthusiasm and a deep love for the local community. I leaned into my spooky-cute style, rocked my space buns, and hit the circuits. Being unapologetically myself—however extra—has not only set me apart but also encouraged others to embrace their own individuality.
Connection has been equally important. I’m not just a passive observer—I actively and consistently engage with my “boos.” Whether it’s attending markets, sharing my favorite finds, or creating custom itineraries, I make it a point to show up, listen, and provide real value. This hands-on approach has allowed me to build strong, meaningful relationships that are at the heart of everything I do.
Any resources you can share with us that might be helpful to other creatives?
In my very specific Connecticut bubble, I discovered two amazing resources. First and foremost, Connecticut Wonderful – a seriously safe Facebook group that shares amazing recommendations and experiences. Second [recommended by the first] is The Connecticut 196 Club: Your Passport & Guide to Exploring Connecticut by Martin Podskoch. Tis a fabulously organized book on the 196 towns in CT. I’ve been pouring notes into the margins with all my favorite spots and hidden gems.
Contact Info:
- Instagram: https://www.instagram.com/connecticutkelsey
- Other: [email protected]
Image Credits
Marie Drost with MD Media