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Career Pivot

What I Found on the
Other Side

the unexpected lesson that had nothing to do with my career

December 20, 2025 9 min read

I told you about the leap. The decision that didn't make sense, the door I walked through even though part of me wanted to dig my heels into the dirt and hold on to everything I had built.

I promised I'd tell you what I found on the other side.

Here's what I couldn't have predicted: the hardest lesson wasn't about medical education at all. It was about something I thought I'd already learned.

The Physician Who Had to Know

Before I tell you about my first failure in medical education, I need to tell you about how I was trained to practice medicine.

My allergy program director was brilliant. There's no other word for it. He taught me to take the most thorough history imaginable. After I examined a patient, he would grill me with questions. What do you want to do? Why? What does the evidence show? Is it supporting your plan?

He played devil's advocate, challenging me to think critically. Then he'd enter the patient room, ask his own questions, and suggest a plan.

He had the questions. He had the answers. That was the model. Clear-cut. Patriarchal. Effective.

So when I began practicing on my own, I felt the need to be exactly like him.

I had to have all the right questions so I could get all the right answers so I could make my recommendations. That was the job, wasn't it? That's what I'd been trained to do.

But something wasn't working.

My patients saw my "right questions" as me seeking answers in disguise. When my questions were targeted and structured, they seemed frustrated at the long visits. They didn't feel heard. They felt interrogated.

The Shift I Almost Missed

So I tried something different.

Instead of asking pointed questions to get to my answer, I invited them to tell their story. I asked open questions that let the narrative unfold. From that narrative, I could pull what was relevant and dive deeper.

Everything changed.

My patients started telling me they felt heard. They thanked me for taking such a detailed history, the same thoroughness that had frustrated them before. The difference wasn't the time I spent. It was who was guiding the conversation.

I remember a moment in clinic, moving from room to room, everything flowing. I wasn't doubting myself. I wasn't worried that when I entered a patient room I'd be stuck, not knowing what to say or what to recommend. I felt that even if I didn't have the answers, I knew how to handle that with confidence.

I can still remember exactly where I was standing. What clinic, what hall, when I realized: I've transformed.

It wasn't until I gained the confidence that I could handle anything that came through those clinic doors that I finally let my guard down. Imposter syndrome was melting away. The real me was beginning to show through.

I was more comfortable with ambiguity. I was okay with not having the right answers, and equally okay with admitting it.

Here's what surprised me: that vulnerability, saying "I don't know," didn't make me a weaker physician. It brought me closer to my patients.

The answer is something that comes to you. Not something you chase after.

I thought I had figured this out. I thought I had learned the lesson.

Then I leaped into medical education.

The Fall Down the Competency Ladder

When I changed from primarily clinician to primarily medical educator, I felt as though I had fallen down a literal competency ladder.

I knew how to teach. But I didn't know how to teach the way I needed to teach.

I had no training in educational theory. No significant experience building curriculum. In only nine months, our first class of students was arriving.

I had never put together a syllabus. Never written course objectives. Never provided faculty development. I truly had no idea what I had gotten myself into.

Yet I still loved it.

The newness of it. The feeling that something great was ahead of me. It was similar to that feeling we all have when we turn on our away messages and shut our laptop the last day before vacation. Every moment of that vacation is ahead of you. You haven't made any mistakes yet. You have no regrets. There is only potential in front of you.

When the students arrived, we celebrated them. Posters. A parade-like show of faculty and staff in the auditorium. It was a celebration that they were there, that we were all in this journey together.

I threw myself into building something from nothing. When the first course launched, it worked. Students enjoyed it. The ratings were good. I had evidence of success.

I had the answer.

Or so I thought.

The Feedback That Landed Wrong

My first failure in medical education wasn't in what I had done. It was in how I received feedback.

Those with more experience and training in medical education began offering me advice. Suggestions for improvement. Ideas for how I might do things differently.

I became defensive.

I HAD the answer already. How could someone tell me it was wrong? It was working, wasn't it? There was proof. Evidence of success. Why would they do this to me?

I didn't see what they saw in me. They saw potential to grow. They saw something I didn't see in myself at the time.

I wasn't ready to hear what I needed to hear.

The armor I thought I'd shed in clinic? It had gone right back on the moment I felt competent again.

The Meeting That Upended Everything

The shift happened in my first meeting with my mentor to review my course.

He suggested what felt at the time like a thousand changes. That all the work I had put into the course over the past years was wrong and needed to be completely revised. I only had a couple of weeks to make them.

I felt something break inside me.

Everything I had built, my identity as a medical educator, was being thrown on its head. Everything within it was spilling out into a jumbled mess.

I wanted to defend what I had built. I wanted to explain why my approach was right. I wanted to point to the evidence that proved I didn't need to change.

The truth is, I wasn't ready to receive help. I wasn't ready to be vulnerable. I wasn't experienced enough to even recognize what I didn't know and needed to learn.

Here's what I finally understood, much later:

He wasn't telling me my work was wrong. He wasn't attacking my success. He was truly invested in my success. Invested enough to force me into vulnerability. He saw more in me than I saw in myself.

they weren't telling me i had to change. they were telling me i had permission to change.

I wasn't ready to accept it.

Learning to Ask Again

What happened after that meeting?

I felt a positive challenge. I wanted to prove I could approach my course differently. I worked on it, asked for feedback (which still hurt to receive), made revisions.

We met weekly, sometimes more often, reflecting together on what I had done, what I could do next. Some things were easy to learn and implement. Others, not so much. There was trial and error. Some things worked well; some did not.

It was the feeling that he was in it with me. That he was always available. That he allowed me to try without micromanaging. Just asking me questions, getting me to think, sometimes making suggestions to start me down the right path.

That changed everything.

Now I invite feedback at almost every conversation. Rather than presenting the answers to my team and my colleagues, I share my thoughts and ask them questions. I present problems not as negatives but as puzzles, challenges we can work on together.

We all ask questions, debate suggested answers, and ask more questions. We don't necessarily find the final answer in these meetings, but that's okay. We are exploring various paths, forks in the road, weighing the options, with the knowledge that we can turn back at any time and try a different path together.

It forces me to be vulnerable. A leader is often seen as the one with the answers. But really, a leader's role is to help others be better, be successful. How can I help others be better and be successful if I'm standing on a soapbox pretending I know all the answers when everyone knows that's impossible?


If you're receiving feedback right now that feels like an attack, and you're wondering whether it might actually be an invitation, this is the kind of work I do as a coach. Sometimes you need a thinking partner to help you hear what you're not ready to hear yet. Book a free discovery call if you'd like to talk.

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Lauren Fine, MD

Lauren Fine, MD

Coach · Speaker · Story Strategist

Lauren Fine is a coach, TEDx speaker, and story strategist helping people at every inflection point identify, shape, and tell the story of who they're becoming. She is a physician, medical educator, Harvard Macy Institute faculty, and the founder of ReasonDx.

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