We were lucky to catch up with Jess Carolan recently and have shared our conversation below.

Jess, thanks for joining us, excited to have you contributing your stories and insights. Owning a business isn’t always glamorous and so most business owners we’ve connected with have shared that on tough days they sometimes wonder what it would have been like to have just had a regular job instead of all the responsibility of running a business. Have you ever felt that way?

I am very happy as a business owner. I’m 25 and still establishing my career, so I feel very fortunate to be self-employed at this stage of my life. From a young age, I always envisioned myself owning a business and working for myself, and I’ve been intentionally building toward that since I first entered the workforce.
I built my business while working as a caregiver, which required a great deal of sacrifice and discipline. I’m grateful for that season because it strengthened my work ethic and taught me how to commit to something long-term, even when it’s difficult.
The biggest struggle in my career so far has been finding the balance between pursuing my passions and protecting my stability and future. I’ve been overflowing with passion since I was a teenager. I’m a multimedia artist and spend many hours each week committed to my creative practice. I also have a deep love for travel, which grew in my early twenties after buying an inexpensive camper van and spending about a third of each year traveling around the United States and beyond. I also love gardening, foraging, and learning about the natural world.
There are moments when I question whether it would be better to devote all of my time and energy to those lifelong passions. I feel that most strongly when I’m deep in the creative process. I find my thoughts asking “Should I have started a ceramic studio, become an art teacher or work at the Nelson Atkins?”. I wonder what it would be like to have to make art instead of getting to make it. Would it still feel expansive and alive, or would it start to feel like another obligation? Would the ideas continue to flow as freely? It’s my biggest source of uncertainty in my career if choosing the logical route is truly the best choice.
After a lot of reflection, I’ve come to appreciate that I don’t have to choose one or the other. I’ve intentionally built both a creative videography business and a functional lifestyle Insurance business . My career in insurance provides flexibility and growing stability, and as I continue to expand in that space, it will only create more freedom. The security I’m building through my insurance business allows me to pursue art, travel, and my love of nature more fully — and it allows my passions to remain exclusively passions.

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

My name is Jess Carolan. I’m a 25-year-old Kansas City local, business owner, and creative.
I began my journey as a business owner by launching a videography business, where I execute creative visions for travel companies and their products, primarily through UGC (user-generated content) freelancing. My work in that space operates on a seasonal and as-needed basis for the brands I’m contracted with. It allows me to combine storytelling, travel, and marketing in a way that feels both strategic and expressive.
As I continued thinking about long-term stability and growth, I expanded into a second business as an independent insurance agent. In this role, I am the sole operator and focus heavily on relationship-based, service-driven work, especially within senior communities. I have found my niche in Medicare, and I truly love being able to connect with older generations and guide them through what can often be a confusing and overwhelming process.
One of the things I value most about my Medicare work is that my services come at no cost to my clients. That makes the guidance I provide feel accessible and rooted in genuine care rather than pressure. From the moment I begin working with someone, my priority is ensuring they feel safe, seen, and informed. My business is founded on customer service and education. I want every client to walk away with a clear, foundational understanding of Medicare and confidence in the decisions they’re making.
When someone first becomes eligible, I guide them through a comprehensive Medicare 101 presentation to build that foundation and prepare them for the decisions ahead. For clients already enrolled, I conduct annual reviews to ensure they’re still receiving the best possible coverage and benefits. Throughout the year, I provide ongoing education– I’m available year-round because Medicare isn’t a one-season conversation.
Beyond direct client work, I’m deeply committed to community presence. I host events throughout Kansas City for seniors, including smoothie drives, scam prevention classes, hygiene drives, craft events, and more. Being an engaged and active member of my community comes first. My business is not just about policies, it’s about people.
Outside of Medicare, I also assist individuals and families of all ages with health and life insurance needs. I love helping people gain clarity and confidence around decisions that impact their future and their families.
In my personal life, I am a deeply passionate person. I value my free time because it allows me to explore, learn, and expand. I’m a multimedia artist, primarily working in ceramics, but I also practice videography, photography, painting, drawing, sewing, crocheting, furniture design, and more. I love exploring how different mediums interact and enhance one another.
Travel is another major part of my life. During undergrad, I took every opportunity to road trip out of my small SUV. After graduating, I bought an inexpensive, older van and began traveling for extended periods throughout the year. I often travel solo, sometimes for over a month at a time. Through my travels I have grown my confidence, independence and learned how to navigate the world boldly in my young adult years. Traveling has also given me the ability to become a published writer and photographer for the travel magazine, ROVA. Through my solo adventures, I have been able to express my personal stories and lessons I learned on the road, and my love of travel opened the door to pursue yet another creative endeavor. I am blessed that my travels have opened up the opportunity to grow as a contributor to the adventure industry. One of the greatest gifts of my career is that it allows me the flexibility to travel while still serving my clients thoroughly and responsibly.
I also have a deep and lasting love for the natural world. I’m fascinated by science and constantly learning about ecology and the environment. I garden, forage, and host guided nature walks in my community to teach others about the magic that surrounds us.
At the core of everything I do with insurance, travel, multimedia works, and art, is rooted in my desire to build a stable and enriching life. Since college, I have been working on balancing a thoughtfully structured career to fund my ever growing and passionate lifestyle.

What’s a lesson you had to unlearn and what’s the backstory?

I like to say that becoming a business owner was the final push I needed to let go of my desire for instant gratification.
One of the biggest lessons I had to unlearn was the employee mentality — the expectation that if I show up and put in hours, I’ll automatically be rewarded. In traditional jobs, effort and time are directly compensated. In entrepreneurship, that connection is delayed.
For the first six months of building my insurance business, I didn’t make a single dollar. Not one. And yet I was working full-time hours growing the business — studying, meeting people, building systems — while also working evening caregiving shifts to support myself financially. It was exhausting, and there were many moments where I questioned whether the delayed payoff would ever come.
Starting any business requires an enormous amount of upfront effort, research, and resilience that goes largely unpaid and often unnoticed. That season forced me to detach from the need for immediate reward and instead commit to my long-term vision.
Patience is a lesson I’ve not only learned but embodied more deeply through becoming self-employed. Entrepreneurship changes how you value your time. No one pays you simply for being present for a set number of hours. Your income becomes directly tied to your discipline, your systems, your expertise, and your ability to stay consistent when results aren’t immediate.
Letting go of instant gratification has been uncomfortable — but it’s also been incredibly empowering. It shifted me from thinking short-term to thinking generationally.

How’d you build such a strong reputation within your market?

There are several key factors that have helped me build a strong reputation within my market.
First and foremost, I owe a great deal of credit to my mentor, Ron Gordon. From the beginning of my journey, he took me under his wing and modeled what ethical, relationship-driven business truly looks like. He places authentic connection at the center of every interaction, and the respect he has earned in our community speaks for itself. When I am out with him, people regularly approach him with genuine enthusiasm and gratitude. Learning from someone so knowledgeable, kind, and principled has been an incredible blessing and has deeply shaped how I operate my business.
Beyond mentorship, I believe my natural appreciation for older generations has contributed greatly to my success in the Medicare space. Long before entering this industry, I found immense value in my relationships with my grandparents and the multigenerational friendships I’ve formed over the years. After college, I developed a close friendship with an 80-year-old retired ceramics professor who became a dear mentor and friend. That relationship taught me how to connect deeply across generations. I genuinely enjoy conversations with older adults — hearing their stories, learning from their experiences, and building meaningful relationships. Combined with my wide range of interests, this makes it easy for me to connect with clients on a personal level. I also believe that asking thoughtful questions is the foundation of meaningful interactions, and that goes a long way in this industry.
Finally, what truly sets me apart is that I have built my business on education and connection. Unfortunately, many people in this industry operate purely from a sales mindset — focusing on volume and commissions rather than clarity and long-term relationships. From my very first appointment, I committed to doing things differently. It is important to me that every client understands the decisions they are making and feels seen as a person, not just a policy. My goal is to serve as a long-term advisor and advocate, not a one-time salesperson.
These principles have allowed my business not only to grow, but to make a meaningful impact. I regularly run into clients in the community and am greeted with warmth and gratitude — which tells me they know I support them well beyond our initial meeting.

Contact Info:

• Website: https://www.sparkadvisors.com/agents/jessica-carolan-7510
• Instagram: https://www.instagram.com/jesss.carolan/?hl=en
• Facebook: https://www.facebook.com/profile.php?id=61580519150391
• Linkedin: https://www.linkedin.com/in/jess-carolan-01b5b4371?utm_source=share_via&utm_content=profile&utm_medium=member_ios
• Other: https://sites.google.com/view/jesscarolancreative?usp=sharing