Exploring Life & Business with Kourtney Roberts of Willow Health Plans

Today we’d like to introduce you to Kourtney Roberts.

Hi Kourtney, so excited to have you with us today. What can you tell us about your story?
Most of my career was spent as a multi-unit leader with a large retail corporation. I started as a seasonal cashier and, through hard work and dedication, worked my way up to district manager. Over 12 years, I gained invaluable experience and truly believed I would spend many more years growing with that company.

Unfortunately in 2021, after years of trying to start a family, my husband and I began the IVF process. During that time, I recognized just how much stress I had been carrying and realized that continuing in a corporate environment was no longer the healthiest path for me. That realization sparked a new direction: going into business for myself.

Three years later, I can honestly say it was the best decision I’ve ever made. Entrepreneurship has challenged me, inspired me, and given me a new sense of purpose and I’ve loved every moment of it.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
It definitely hasn’t been a smooth road. Leaving corporate meant starting from zero, facing doubts, and learning how to balance it all. To make things harder, within the first three months of becoming self-employed, I had to put down my dog I’d had since college, experienced a failed IVF transfer, and lost my grandmother to cancer. It was an incredibly heavy season.

But those struggles reminded me why I chose this path and made the wins that much sweeter. When you’re forced to lean on yourself, figure out a plan, and keep moving forward, you discover a strength you didn’t know you had. The journey of learning about yourself is a rollercoaster of emotions, but it’s also one of the most rewarding parts of entrepreneurship.

Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
Willow Health Plans is all about making health insurance simple, personal, and empowering, especially for people who feel overwhelmed by the process. What is even better is my services are free! I work with individuals and families under 65, as well as small business owners, to find tailored health coverage that truly fits their needs. Many of my clients are self-employed, 1099 contractors, between jobs, early retirees, or simply people who need health insurance for other reasons.

The truth is, the health insurance industry is incredibly confusing. I can’t fix the system, but I can help you navigate it. My goal is to ensure people understand their options, feel supported, and walk away confident in their decisions. What sets me apart is the way I approach it—I’m not just looking at a policy, I’m looking at the person, their family, and their long-term goals. I focus on education, clarity, and ongoing support rather than just selling a plan.

If there’s one thing I’d want readers to know, it’s that health insurance doesn’t have to be scary or transactional. With the right guidance, it can be a tool that gives you freedom and security and that’s exactly what Willow Health Plans is here to provide.

Any advice for finding a mentor or networking in general?
If you’re looking for a mentor, seek out two: one within your industry and one outside of it. A mentor in your own field can give you the blueprint, sharing what’s worked for them so you can learn from their strategies without having to reinvent the wheel. A mentor from another industry brings a fresh perspective, offering motivation and insights that can elevate both your work and your life. Having both helps you stay grounded while also challenging you to see things in new and inspiring ways.

Contact Info:

• Website: https://willowhealthplans.com/
• Instagram: https://www.instagram.com/willow_health_plans/
• Facebook: https://www.facebook.com/WillowHealthPlans

Image Credits
For the headshots: Emily Young CnE Photography