Is It Too Late to Start Over? One Surgeon's Bold Career Pivot

Could your daily frustrations actually be pointing you toward your next purpose?Dr. Matt Jones shares his remarkable journey through what he calls a "triple transition"—moving his family from Chicago to Denver, leaving his medical career, and launching towlos, a peer-to-peer trailer sharing marketplace. His parents taught him not to feel boxed in by expectations. That courage serves him still. Matt reveals the power of a "frustration journal" that transforms daily annoyances into entrepreneurial opportunities. "Difficulty doesn't mean bad," he reminds us. His story challenges the belief that life must always go "up and to the right," showing how curiosity and authenticity can lead to unexpected fulfillment.Dr. Matt Jones is a former orthopedic surgeon turned entrepreneur and founder of towlos, a peer-to-peer trailer sharing marketplace connecting trailer owners with renters across the U.S. After completing his residency at the University of Arizona and sports medicine fellowship at UCLA, he practiced orthopedic surgery for a decade in Indiana and Chicago. In 2021, Matt made the bold pivot from medicine to full-time entrepreneurship. Since 2023, he's also served as Managing Partner at AJM Development. He lives in Denver with his wife and three children, where they enjoy the Rocky Mountains and active outdoor adventures.About The Show: The Life in Transition, hosted by Art Blanchford focuses on making the most of the changes we’re given every week. Art has been through hundreds of transitions in his life. Many have been difficult, but all have led to a depth and richness he could never have imagined. On the podcast Art explores how to create more love and joy in life, no matter what transitions we go through. Art is married to his lifelong partner, a proud father of three and a long-time adventurer and global business executive. He is the founder and leader of the Midlife Transition Mastery Community. Learn more about the MLTM Community here: www.lifeintransition.online.In This Episode: (00:00) Introduction and Opening(05:11) The Triple Transition of 2022(15:29) Introducing towlos: A Trailer Marketplace(20:31) The Five-Year Decision to Leave Medicine(27:10) Midlife Transition Mastery Ad(30:37) Why He Left: Burnout and the Healthcare System(41:15) Transition Mastery Coaching Ad(50:50) Finding Support and Resources to Transition(1:00:26) Staying Curious and Not Feeling Boxed In(1:04:56) The Frustration Journal Tool(1:08:43) Closing and How to ConnectLike, subscribe, and send us your comments and feedback.Resources:Email: [email protected] Website: towlos.com  (peer-to-peer trailer sharing marketplace)LinkedIn: https://www.linkedin.com/in/matthew-d-jones-11b34372/Email Art BlanchfordLife in Transition WebsiteLife in Transition on IGLife in Transition on FBJoin Our Community: https://www.lifeintransition.online/My new book PURPOSEFUL LIVING is out now. Order it now: https://www.amazon.com/PURPOSEFUL-LIVING-Wisdom-Coming-Complex/dp/1963913922Explore our website https://lifeintransitionpodcast.com/ for more in-depth information and resources, and to download the 8-step guide to mastering mid-life transitions.The views and opinions expressed on the Life In Transition podcast are solely those of the author and guests and should not be attributed to any other individual or entity. This podcast is an independent production of Life In Transition Podcast, and the podcast production is an original work of the author. All rights of ownership and reproduction are retained—copyright 2025.