Meet Kym Tolson | The Traveling Therapist


We had the good fortune of connecting with Kym Tolson and we’ve shared our conversation below.
Hi Kym, we’d love to hear about how you approach risk and risk-taking.
From transitioning from a traditional therapy practice to becoming a digital nomad, to founding communities like Bill Like a Boss and the Clinical AI Club, taking risks has always been about following my intuition and being willing to step into the unknown. Whether it’s diving into the intersection of AI and therapy or moving to new places regularly while running a business, these leaps have led to some of the most rewarding experiences both personally and professionally.
I view risk as an opportunity for growth. Each decision I’ve made has been grounded in the belief that change and challenge create momentum. Being willing to take those risks has not only allowed me to build thriving communities of therapists but has also given me the freedom to design a life that balances my passion for travel and helping others. Ultimately, risk-taking has empowered me to break free from conventional norms and create a career and lifestyle that aligns with my values.

Alright, so let’s move onto what keeps you busy professionally?
My work revolves around supporting therapists in navigating the complexities of insurance billing, integrating AI into their practices, and even building a life that allows them to travel the world, just like I do. What sets me apart is that I’ve walked the same path. I know the struggles therapists face because I’ve been there—balancing client work, managing the intricacies of insurance, and trying to find the time for a personal life. This lived experience fuels my passion for creating resources like Bill Like a Boss, which helps therapists streamline their billing process, and the Clinical AI Club, where we explore how technology can make running a private practice more efficient.
What I’m most proud of is the community I’ve built. Watching therapists regain their time, grow their businesses, and embrace the freedom to travel and live life on their own terms—like I’ve done as a digital nomad—is incredibly rewarding. It wasn’t an easy journey, though. Transitioning from a traditional therapy practice to this more unconventional lifestyle meant stepping outside my comfort zone repeatedly. There were moments of doubt, especially when I had to balance my personal life with these major career changes. But each challenge became an opportunity for growth.
Overcoming these challenges taught me resilience and the importance of leaning into discomfort. One of the biggest lessons I’ve learned is to trust the process and embrace the unknown because that’s where the magic happens. By being flexible and open to new opportunities, I’ve been able to create a career that merges my passion for therapy, technology, and travel.
What I want the world to know about me and my brand is that I’m here to show therapists that they can build a life that reflects their personal and professional dreams. Whether it’s breaking free from the office to become a traveling therapist or using AI to simplify their practices, my goal is to empower others to reclaim their time, pursue what excites them, and create a meaningful life.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
Since I live in a different city every few weeks, I’ve become a pro at making the most of wherever I am, and I love curating unique experiences based on the local vibe. So, if my best friend was visiting, I’d tailor the trip to the city we’re in—but here’s what a typical week might look like!
We’d start with some exploring—whether that’s wandering through the city’s historic neighborhoods, hiking a nearby trail, or taking a scenic bike ride. One of my favorite ways to immerse myself in a new place is through food, so we’d definitely hit up some local gems for brunch and dinner. I love finding a mix of casual spots with amazing food and fancier restaurants for a special night out. Think farm-to-table brunches and stylish rooftop dinners with a view.
I’d also make time for self-care and wellness! I’m a big fan of ClassPass, so we’d sign up for a yoga or pilates class, followed by a visit to a local spa for some relaxation. Maybe even an afternoon at a cool coffee shop to chill and catch up.
We’d explore the local art scene, whether that’s visiting galleries, checking out a local theater performance, or even a street art tour. I love discovering the creative side of each city, and it’s always fun to find something unique and unexpected.
Of course, I’d also plan some fun evenings out, whether it’s cocktails at a chic bar or a live music venue that captures the local flavor. Each city has its hidden gems, and I love finding those spots where the vibe is just right.
Overall, the goal would be to soak in the local atmosphere, enjoy some great food, and experience the best that the city has to offer at a relaxed pace. Whether we’re in a big city or a smaller town, every place has something special to share!

Who else deserves some credit and recognition?
Megan Gunnell, My Business Bestie & Founder of The Thriving Well Institute. Dr. Amber Lyda, founder of the Online Therapist Group on Facebook who was my mentor and inspiration to take my therapy practice all online back in 2018.
Website: https://www.thetravelingtherapist.com
Instagram: https://www.instagram.com/thetravelingtherapist_kym/
Linkedin: https://www.linkedin.com/in/kym-tolson-lcsw-csac-316aa019/
Facebook: https://www.facebook.com/groups/onlineandtraveling/
Youtube: https://www.youtube.com/@KymTolson

