How to Prepare for An Off-Road Adventure

Lena Cheng, MD
6 min readDec 17, 2020

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When people hear about my career as physician-turned-marketer, the most common question I get is “How did that happen?”

My answer? I finally decided to go off-road.

Throughout high school and college, I saw a path ahead of me that seemed so clear: Medical school → internship → residency → practice medicine happily ever after. Being a doctor was something I’d wanted (or so I thought) for much of my life. But from that very first day in medical school, I felt lost. The direction was predetermined yet I felt directionless and less like myself than I ever had.

The first half of medical school, I told myself, ”This doesn’t feel right, but just get through the basic sciences and labs. It’ll get better after that.”

The second half of medical school, I was rotating through different medical specialties and getting a chance to treat patients, but still felt out of place. I convinced myself that I just needed to endure school and that it was understandable that, as a medical student, I didn’t feel as strong a connection to practicing medicine as I’d expected. School isn’t “real life.”

During my internship and residency, I powered on down the path. Three years of more training and education, and closer to the destination of independence as a practitioner.

For years, I pushed doubts aside and justified my decision to stay on course. You’ve put in so much time and effort. It’d be a shame to waste all those years of studying and training. Think about the debt from medical school. You’re not qualified to do anything else. Just. Keep. Going.

Then the path took me to the completion of my residency and, shortly thereafter, passing my internal medicine board-certification exam. At that point, I expected to experience a magical moment where I felt whole, passionate about my vocation, and more like my authentic self.

But that moment never came. For months after my board certification, I wrestled with acceptance. Acceptance that I no longer wanted to settle down at the destination of being a practicing physician and that it was time to go off-road.

And so after eight years of putting one foot in front of another on the traditional path, I took my first step into unknown territory. It was one of the most difficult decisions I’ve made in my life. As with many decisions of this magnitude, I made this one amidst a great deal of angst, contemplation, and fear — but I also did it with great resolve. I knew deep to my core that I deserved to reimagine the course of my life.

Knowing there would be uncertainties aplenty, I embraced a range of strategies and tools in preparation for the off-road adventure. Here are three important steps that helped me get the most out of those early days of transition:

#1 See the entire map.

Shortly after making my decision to leave clinical medicine, I began identifying and researching physicians who’d successfully pursued non-clinical careers. Some I already knew and for those I didn’t (this was before LinkedIn) I tried to get an intro through my network or would simply cold call.

I asked every one of those physicians on my list for informational interviews. These were structured, 30-minute discussions during which I explored exactly how they made their decisions to leave clinical medicine and the concrete steps they took to do it. They were entrepreneurs who’d started their own companies, medical directors at biotech companies, medical writers, hospital administrators, and healthcare consultants for industry. I was fascinated with the stories people told about their transitions and felt a strong sense of tribal connection.

The process enabled me to zoom out and see the entire map, not just the path I was on. By shifting my perspective, I could see that there were different journeys to be explored. Others before me had gone off-road, so why couldn’t I? It also filled me with hope that I could have a life filled with intention, passion, and meaning, well beyond treating patients. For the first time in years, the world seemed full of possibility and promise.

#2 Ask for directions (aka get help)

One of the physicians I interviewed said he’d worked with a career coach on his transition, a concept that, as a practicing physician, I’d never heard of before. A few referrals later, I found myself meeting weekly with a woman who’d begun her own career as a registered nurse and transitioned into career coaching.

These meetings helped me see the countless clues from the past eight years — clues I’d ignored — that I might be happier going off-road:

  • Throughout medical school and residency training, I constantly sought distractions from the work at hand, whether it was student leadership, art contests, short story writing, and even a sculpting class
  • I explored a broad range of specialties within medicine, greatly hoping each time to find “the one” but the fit was never right. I thought for a while that I was destined for a plastic and reconstructive surgery residency, only to make a last-minute switch to internal medicine. Even within internal medicine, I considered various specialties, including occupational medicine, endocrinology, hospital medicine, alternative medicine, and even field medicine such as with Doctors Without Borders. But none of these felt compelling or engaging enough. Overall, the path was the same, even if the scenery was slightly different
  • As I reached milestone after milestone in medical school and residency — everything from delivering my first baby to receiving my MD diploma to passing the boards — the celebration would be short-lived and then inevitably I’d settle back into feelings of unease, anxiety, and dissatisfaction
  • I was often physically and mentally exhausted, even after the deepest sleep and longer periods of rest

Through guided discussions, exercises, and career tools, my coach helped me see in plain sight that this path wasn’t serving me well and that I deserved to dream about a different way forward and, in fact, that my physical and mental health depended on it.

#3 Find the right travel companions

Once I decided to go off-road and leave clinical medicine, I felt compelled to share the news with colleagues, friends, and family. Immediately, I was bombarded with reactions of skepticism, disbelief, and fear that I was making a massive mistake. In my mind, I was celebrating this momentous decision, yet outwardly I was spending an enormous amount of effort defending and explaining that decision.

Quickly I learned to shut down conversations with naysayers — however well-intentioned they were — and surround myself with a support system of people who had faith that going off-road was an adventure I needed to take and that I’d find a way to succeed. This was a small group of people, but one that helped me embrace the risks I was taking and allowed me to be vulnerable about my stumbles, fears, and dreams. Having those people by my side as I paved an off-road path for myself was essential, particularly in those first few years when I (and all the skeptics around me) wasn’t always certain where I was going.

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Years later, I look back on this time with gratitude for the people who gave so generously of their time and support, and prepared me for my adventure. My trusted “travel companions” rallied around me, my career coach showed me compassion and patience through many trying discussions, and so many busy physicians, the ones with non-clinical careers — many of them strangers — took time to share their insights, stories, and advice. It’s hard for me to imagine where I’d be today without the inspiration and courage they all bestowed on me.

Whether you’re preparing to go off-road in your own career or have been off-roading it for years, I’d love to hear from you. How did you know it was time? What’s working for you? What or who have been your sources of strength and resolve? Drop me a line.

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