What I Got Wrong
Reflections at the halfway point of medical school
p.s. these are personal reflections only; views are my own and have evolved with experience.
I’m currently at the halfway point of medical school — two years in, just started rotations last week, Psychiatry is my first rotation. These are my thoughts and reflections on the assumptions I had going into medical school, and my reflections on them now, two years in, 50% of the way through. The caveat is that these reflections are all specifically things that I got wrong, because I find it a worthy endeavor to reflect on incorrect predictions and assumptions. People far too often brush those under the rug, which I think is foolish, because I believe what you were incorrect about leaves the greatest opportunity for you to tune your prediction engines and get increasingly better and more accurate with future predictions. In any case, I will soon also share things that I turned out to be correct about. I hope you enjoyed this reflection. I dictated it to my car while driving home to see my parents. Perhaps I will dictate the reflection of things I was correct about on my drive back to Connecticut in a few days.
Thinking that I could run my agency while still doing well in med school.
The whole reason my first business was a services business was because I knew that I had more time than money, so I could sell my time to people who have more money and less time. I didn’t realize that by going to medical school, now I have less time and less money.
Lesson learned: Always be clear about what you have that the other person does not.
Getting attracted to B2C businesses because they seemed more exciting.
I thought maybe B2B businesses were too boring and not something I wanted to do for the rest of my life. And I got attracted to B2C businesses because it seemed like all my friends, anybody I knew, only knew about B2C businesses and nobody really knew about any B2B businesses.
Lesson learned: Alex Hormozi has a good metaphor for this: the idea of distraction, by things that look good in fleeting moments, but in the long run make you lose out on something that was much better. He calls it the woman in the red dress. Do not get distracted by the woman in the red dress.
Thinking medical school wouldn’t actually be that hard.
When I was premed, I used to talk a lot about how premeds just love to complain. It seemed like they socialized — bonded — based on complaining about things. I remember being somewhat annoyed by this because I was also involved in some engineering, computer science, and business classes, as well as an international relations class, and I noticed that a lot of the folks in those other classes were working just as hard, if not sometimes harder than the premeds, especially the engineering kids, but they just weren’t complaining about it as much. This left me with a sour taste in my mouth, thinking that people in medicine just like to think they’re doing the hardest thing in the world. And to be honest, I do think that at the premed stage this was pretty accurate. So I thought it would be the same case in medical school — that it must not actually be that difficult, and it’s probably the same personalities who have just been socialized on getting closer to people based on common misery and complaining.
I turned out to be somewhat wrong about this. Medical school truly is genuinely really hard. A lot of people in my class and the people I know in medical schools across the country are genuinely some of the hardest workers, with an abnormally gifted talent for learning at a rapid pace and remembering at simply superhuman levels — and I say this with no exaggeration. In terms of pure academics, these are some of the most brilliant and talented people, frankly, in the world, if you’re talking about raw horsepower when it comes to learning and remembering.
Lesson learned: No matter what the thing is, becoming “knowledgeable” in it is an immense amount of work. No if, ands, or, buts.
My romanticized vision of what medicine was.
I grew up thinking medicine was the echelon of higher education. I imagined myself among the ranks of the absolute greats. I thought I would feel closer to Darwin, Sydenham, Galen, Hippocrates, Avicenna, and William Osler. I pictured medicine as an intense, serious discipline of excellence—of scientific rigor, exactness, resoluteness, discovery, and the true scientific method: the humble acceptance that we know nothing for certain. We hold what we know lightly, knowing it may be overturned tomorrow, and yet we must still act decisively to heal and protect the vulnerable.
In many ways, it is exactly that. But I was surprised by how much the broader currents of society now shape daily medical practice and training. Doctors are increasingly expected to address not just disease but the full spectrum of social and environmental factors affecting health. This is not to say it’s inherently good or bad—it simply reflects the world we live in today. Still, I’ll admit it wasn’t what I expected when I entered. I had envisioned a sharper focus on pathophysiology, diagnostics, and therapeutics as the core of professional training.
Lesson learned: It is usually foolish to expect that the cultural zeitgeist will not penetrate every aspect of society. Your default assumption should be that it does.
Bringing the wrong mindset from entrepreneurship into medicine.
This one’s a bit of a weird one. After having spent one to two years running my own businesses, much of the confidence a beginner needs to go from zero to one — to launch, make their first sales, put marketing content out there — comes from absorbing this mentality: others do not actually care about you as much as you think they do. People are not observing and ridiculing and thinking about you as much as you think they are. These fears that are preventing you from putting yourself out there are, in fact, a selfish aggrandizement of the role you play in other people’s lives. You have a very minuscule role in people’s lives and they do not think about you. Nobody cares about you, so do what you need to do. They’re not noticing you. Only you think they are.
This line of reasoning is absolutely true in the business world, and it helped me immensely. So when I began medical school, I carried the same line of reasoning with me.
In this new environment, it turned out to be oh so wrong.
I stood out like a peacock fanning his feathers — like a tall poppy, like the guy who couldn’t shut up about everything else he was doing. I drew attention—sometimes positive, sometimes not—because the rubric wasn’t built for the personality I had cultivated over the past two years in business. I certainly earned the love and appreciation and respect of many — for the same things people have always known to love and respect me for, which is my utmost honesty, my sincerity, and my willingness to say what I deem to be true with no hedging, to say what needed to be said, and to be the voice for perspectives not in the room when I felt I was able to do so.
But suddenly everything was indeed being monitored. Suddenly everybody did indeed care. Suddenly I no longer represented just myself — I allegedly represented an institution, a profession. I went from being a young underdog with nothing to lose and everything to gain, and instead became more like the egotistical diva on a sports team who doesn’t realize that what they’ve joined is bigger than themselves. I failed to realize this early on. I know it now, and I walk that line much more carefully.
Lesson learned: Always know what game you’re playing, and what the rules are. If you’re playing soccer when everybody’s playing lacrosse, you’re gonna lose badly, look like an idiot while doing so, and your team will suffer. On that note, always know if you’re laying an individual sport or a team sport. Medicine is a team sport.
My guilty secret going in.
This one’s a bit of a weird one. Before I came to medical school, I had one guilty secret—one I was slightly ashamed of and felt somewhat paradoxical about. Deep down, I believed that much of what we do in medicine was less powerful than the fundamentals: consistent sunshine, exercise, real food, sleep, and close human relationships. I thought these alone could help most people live as healthy a life as possible, treat or prevent a huge amount of illness, avoid unnecessary harm, and reach the highest quality of life their genes would allow.
This was my guilty secret as I began medical school and took the oath of Hippocrates. And though I still believe those fundamentals are profoundly important, I’ve simply seen too much to remain that simplistic.
I’ve now witnessed how medications and interventions can meaningfully change trajectories in severe cases where lifestyle measures alone aren’t enough. My early view underestimated the complexity of human biology and the real suffering that requires more targeted help. On psychiatry especially, I’ve been struck by how thoughtfully my attendings and residents approach treatment—working hard to use the minimum effective dose and prioritizing non-pharmacologic tools whenever possible. The patients who stay on medication long-term are usually those for whom the risks of stopping are clearly greater.
Lesson learned: Allow yourself to hold convictions, but stay open to being wrong. People are usually trying to do the right thing to the best of their abilities and judgment. Not everyone has the same tools or data, but that doesn’t make them malicious—it often just reflects the limits of their environment and training.
Thinking medical school would give me an unfair advantage in healthcare innovation.
I thought that being in medical school would give me a massive competitive advantage — that I would have access to decision makers within hospitals, and as somebody who is entrepreneurial with a background in software engineering, marketing, and design, I had the absolutely perfect skill set to develop solutions as soon as I came across problems, get them in front of decision makers, and get them implemented rapidly. It turned out I was absolutely delusional about this. Healthcare might be the slowest moving sales cycle I will ever come across.
Despite being on good terms with some of the most senior people in various hospitals, there are endless steps and gatekeepers no matter who you know and no matter what your entry point is. I developed a system I thought was a guaranteed win — a platform that would preemptively detect billing claim denials before they were denied and auto-suggest ways to get them approved before submission to the clearinghouses, with a billing department trained on a machine learning model using the hospital’s own data locally, to minimize claim denial rates. I built this MVP within a weekend of an email going out to our larger community at the hospital about hiring a consulting agency to address problems in revenue cycle management. I thought this was the best possible timing. I walked straight to the CEO’s office. He directed me to the Senior VP of Billing, who expressed some interest, and then seemed to never quite respond again.
That was my first lesson: healthcare is a very slow sales cycle. Persistence is required. Hospitals don’t want to buy systems that are brand new — they want to buy systems that help them sleep better at night because they know they’re vetted and de-risked. That’s a lot harder to provide, and you have to get a lot more creative in demonstrating that with confidence. I thought all I would need was a degree. I was wrong. I would need much, much more.
Lesson learned: Proximity, credentials, timing, all of these matter. But persistence and relentlessness. Are probably what matter most. You don’t actually need to be an insider if you’re a relentless outsider. And if you think that being an insider alone will give you an advantage you’ll probably won’t do the things that the relentless outsider is doing and they’ll end up winning. So even if you are an insider, it does not substitute any work. You still must do all the work that you would have had to do as an outsider. It is an add-on, not a replacement.