Finding Your Way

Lessons learned on my journey from clinical care to entrepreneurship

“We delight in the beauty of the butterfly, but rarely admit the changes it has gone through to achieve that beauty.”

— Maya Angelou

Photo by Miguel Bruna on Unsplash

How the heck did you figure it out?

Having made a successful leap from clinical medicine to entrepreneurship, I am often met with a variety of questions that all basically translate to “but how did you do it?”

From this side of the journey, my experience might seem clean and straightforward. But it was anything but, and like anything meaningful, my transition required time and work. The prism of time shines light on the successes, but the challenges are reflected back too, the oceans of tears, heart-wrenching “break ups” with academic mentors, the ambiguity of it all. It is in the overcoming where the true learning lies. It is in the bruises and bumps where the real lessons are learned. I know that my journey won’t be the same as anyone else’s, but if there’s some kernel of my experience that resonates for another young clinician bumbling through and trying to find their way in their career, then it will have been worth it to have told my tale.

The first chapter of my career was as an academic cardiologist at Brigham and Women’s Hospital in Boston, MA. I had always intended to become a physician. I grew up the daughter of two immigrant physician parents, an ENT surgeon and an anesthesiologist. I had not one iota of parental pressure, but still I pursued medicine 100% because of my parents, because I witnessed daily how my parents were met with gratitude and love and appreciation of their impact in our suburban Virginia community. It left me with this sentiment: I want to be a person that makes people feel this way. Medicine was an obvious choice, a natural phenotypic expression of that which was already imprinted in my DNA.

So with excitement and anticipation, I got on the train, the doctor train, and it took me via some incredible stations along the journey - Harvard college, Harvard Medical School, and Brigham and Women’s Hospital for internal medicine residency and cardiology fellowship. At the terminus, I was dubbed academic cardiologist and grant-funded clinician scientist. It would not be at all disingenuous to say that I loved it, this combination of caring for patients, teaching, and pursuing scientific research together fulfilling my desire to make people better and at the same time feeding my intellectual curiosity.

But then I started to feel unsettled. At first, I wasn’t quite sure why. I certainly felt I was having an impact 1:1 with patients, but the clinical work was beginning to feel rote, the learning curve asymptotic. The research was starting to feel unlikely to move the needle for patients anytime soon, if ever. Writing papers solely for the sake of another notch in my resume to move me up the promotional ladder no longer felt valuable. What’s a title anyway? Like many, I could have lingered longer, hoping for change, frustrated. Instead, itchy and impatient, I picked my head up, looked around, and started asking myself some hard questions.

Step 1: Know thyself.

So often in life and in career, we just board the ambition train, cede the role of conductor to someone else. Guided by expectation, the word “should” creeps its way into every sentence, every thought. Really the only person who should steer that train is you, but to do that, you have to truly know yourself and know where you are going. What makes you tick? What are your aspirations? What bring you joy?

“I want to be a doctor” proves an insufficient guidepost. “I want to do something different” is not nearly crystal clear enough. To steer yourself on your life and career journey, you first need to know yourself. And to know yourself turns out to not be so easy a task. What is your why? My why back then would have been I want help people be better. It was and still is a pretty solid and sincere guiding life philosophy. So what was wrong? Why were things no longer adding up?

Step 2: Pick your head up. Ask yourself the hard questions.

Being on the medicine train requires grit and perseverance, and survival on the path to becoming a physician requires you to put your blinders on. At some point, you may find you no longer know yourself, or worse yet, you never knew yourself in the first place. The difficult next step is to actually pick your head up out of the sand and reevaluate. That introspection will almost certainly prove uncomfortable, agita-inducing, but self-work is some of the most rewarding and necessary work you will do. Frankly, even absent discontent, we should all be periodically reassessing, asking ourselves: Is this the right job for me, the right environment, alongside the right people? Am I putting my value, my gifts, to best use? Am I still being true to my why? Does this work bring (or still bring) me joy?

If the answers to these questions are a resounding yes, then that is outstanding. Put your head back down in the sand and keep at it. We’ll see you again in a couple of years when you do your next self-evaluation.

But if asking yourself these questions leaves you sensing a hollow in your belly, you owe it to yourself to figure out why. What’s missing? What changed? How did you fall off the track? These sticky questions require personal work, but being better, feeling better, change is never easy, is it? You owe it to yourself do this work.

Personally, I discovered that my why had never changed. I still loved people. I still craved the goal of making people feel better, be better. But while the mission was unchanged, the strategy and tactics for how to achieve it weren’t working any longer. I needed to do it faster (academia was too slow a burn); I need to do it bigger (1:1 with patients was delightful and impactful, but not scalable); I needed to be growing again (the learning felt stagnant).

Step 3: Be curious and you will build your web.

When I opened the aperture, I discovered a whole world of healthcare outside my little bubble - tech, digital health, tech-enabled services, venture capital, private equity, integrated delivery systems, value based care, employers, payers, government, you name it. For me, it never felt like job hunting. I was just curious. Frankly, I was just looking for inspiration.

I started with one conversation and another and another. I cold-emailed interesting people. I opened up with patients. I met with the wife of a patient who is a serial healthcare entrepreneur. I reached out to leaders of digital health companies, a then nascent space. I met with a venture capitalist patient of mine to learn more about their work. I built my own website and started a blog. I became a regular contributor to the Harvard Health Letter. I reached out to the media relations team at the Brigham and even did a few spots on local news.

Bit by bit, I learned what I liked and what did not resonate. At the same time, I was building a network of connections, friends, supporters, some of whom would later become dear mentors and sponsors. I liken it to a spider building a web. With just a single measly strand of web, the chances of catching a next meal are pretty slim. But build a whole web, an intricately crafted, interlacing network of threads, and the likelihood of nabbing something goes up exponentially. Some conversations were dead ends. Others led to more introductions, new doors to be opened. Eventually, something stuck. Eventually, I found AbleTo.

Step 4: Leverage your expertise, but stay humble.

Chapter 2 of my career was a deeply satisfying, decade-long, ride as Chief Medical Officer at AbleTo, one of the first virtual mental health companies. I started in 2013, when the “office” was the founder’s living room, when we were fewer than 10 employees, when the world didn’t understand “virtual” and certainly didn’t seem to care much about mental health at all. As a cardiologist, I was in a supremely powerful position to push for change. I could help the payers and providers see the impact we could have on physical health outcomes for patients with both medical and co-morbid mental health needs, something I witnessed so commonly in my clinical practice. As a data nerd and former researcher, I could clearly articulate the financial opportunity, the data clearly demonstrating significant and potentially avoidable greater utilization and medical spend when behavioral health needs of patients with medical conditions went unmet.

I had enough comfort and confidence in myself and my basic intelligence that I was also free to not know things, and there was certainly a lot I didn’t know. Like basic acronyms such as LTV, CAC, COGS, ROI, EBITDA, the difference between fully insured and self-insured commercial books of business, the role of the employer in driving healthcare benefits decisions, participating preferred stock, agile product development processes, rules and regulations around delegated credentialing. I had to remind myself, “I am not dumb, but I just have never been taught these particular topics.”

Confidence in my strengths enabled me to be humble about my blind spots, and that in turn allowed me to learn with ferocious curiosity.

Step 5: Rinse and repeat

Self-exploration is a constant game. At several junctures even during my ten-year AbleTo tenure, I had to pick my head up and re-evaluate. So I contend that career is not a one-time decision, but a constant game of reassessment with micro and sometimes macro adjustments.

How the heck did I figure it out? Well, though my path almost certainly won’t be the same as your path, the core principles will be the same. I started by being willing to ask the hard questions, doing the difficult personal work, developing a new network conversation by conversation, being confident but humble and curious, and doing it all over again. As I write Chapter 3 of my career, I’m trying to heed my own advice, rinsing and repeating, exploring and learning, building a new web, and we shall see what sticks.

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“You find the path by walking it.”

— Maya Angelou