Law school had been my plan since early high school. I participated in mock trial and Model UN, loved rhetorical argumentation, interned at multiple law firms, and assumed the path forward was obvious. I studied History, Creative Writing, and Entrepreneurship in college because I loved them and thought that studying topics I was genuinely interested in would help me get a good GPA, which, alongside the LSAT, were the two most important metrics determining the caliber of law school I would go to (and resulting career I would start after law school). But it was the process of studying for the LSAT that caused me to pause. Even with tons of practice tests and an expensive prep course (I spent more time in the library working on practice questions during the first semester of my senior year than my entire college career combined), I couldn’t improve my score to a competitive range, which meant that pursuing a law career would be exponentially more difficult. I had to pivot. Looking backwards, I can connect the dots. But at the time, it was hard to see how a liberal arts foundation would prepare me for anything, let alone a career in technical product management.
After graduation, I took my first real job: a pre-sales consultant role at an Electronic Health Records (EHR) company, working with software that had been developed in the 1980s and barely updated since. I knew nothing about healthcare. I knew almost nothing about technology, especially “old” green-screen command lines. And yet this moment of profound uncertainty became the springboard for everything that followed in my career. What saved me wasn’t domain expertise. It was the ability to ask good questions, understand how systems evolve over time, and translate between what customers needed and what technology could do. In other words, my liberal arts education had taught me how to learn. And that skill, I would discover, was far more valuable than any specific knowledge I might have learned in school.
Most people in my position would have focused on memorizing the user guides. Learn the features, understand the workflows, be able to demo the system. But I couldn’t stop asking questions that weren’t in the manual. Why did the healthcare system in the US develop this way? Why was this technology built like this? Why did decisions made decades ago still constrain what we could do today? The EHR software had been designed in the 1980s, a world where technology’s job was to track billing, categorize balance sheets, and digitize paper medical records. When user experience started to matter, UIs had to be bolted on. The result was a fragmented system that reflected its evolutionary history. Understanding this wasn’t just intellectually satisfying, it was strategically essential. Once I understood why the software was built this way, I could help customers see not just what it did, but what that meant for them and their unique workflows. This is what liberal arts had trained me to do: look beneath the surface through deep research, understand systems as products of their time, and trace the threads that connect past decisions to present realities.
I discovered that my super power wasn’t just knowing healthcare or understanding technology. It was being able to translate between domains. Customers described problems in the language of financial office workflows. The software was designed in the language of database architecture and billing compliance. I stood in the middle and made those two worlds understand each other. That translation requires empathy, genuinely understanding how others live their lives and what they’re trying to solve. It requires historical perspective, knowing why things are the way they are. And it requires communication skills, making complex ideas accessible and translating insights across many domains. Anyone can read a manual. Not everyone can understand the why behind it and translate that understanding into actionable insight for other humans. This ability to work backwards from customer problems to technical solutions became the foundation of my career in product management. But it started with liberal arts teaching me to ask questions across disciplines, synthesize information, and communicate clearly.
What I didn’t know at my first job was that this skillset would become the most valuable thing anyone could bring to work. We’re all living through a moment when AI can summarize documents, generate code, and answer factual questions with increasing accuracy. The knee-jerk reaction is to double down on technical skills. Learn to code (vibe-code even), master prompt engineering, become AI-proficient. But that misses the point: as AI handles more routine cognitive tasks (and ever-more impressive ones), distinctly human skills become more valuable, not less. AI can retrieve information but can’t ask the right questions. AI can identify patterns but can’t understand why those patterns emerged or what they mean in context, even as the context windows of AI tools grow ever larger. AI can generate text but can’t translate complex ideas across domains in ways that resonate with different audiences. AI can optimize for known variables but can’t imagine what questions we should be asking in the first place. These are exactly the skills liberal arts develops: curiosity, critical thinking, historical perspective, empathy, communication, and the ability to work across disciplines. Most importantly, liberal arts teaches you how to learn. That is the primary skill we all need in this new AI era. It’s a muscle that takes practice, but it’s so worth it to actually understand other humans, their motivations, and the best way to translate insights to them.
Walking into that first job, I didn’t have answers. Instead, I had a framework for finding them. Studying history and creative writing had taught me to ask questions, understand systems holistically, and communicate what I learned. Liberal arts doesn’t hand you a manual to memorize. It teaches you how to figure out what the manual doesn’t say and what to do when there is no manual at all. It shows you where the bias is. It teaches you to be curious about how the world works, to question assumptions, to see connections others miss. It teaches you that understanding the past helps you navigate the present and imagine the future. Most importantly, it teaches you that once you’ve figured something out, the real work is communicating it clearly to others. Because understanding means nothing if you can’t help others understand, too.
My pivot away from law school felt legitimately like failure at the time. But that first job taught me something essential: the most valuable thing I brought wasn’t what I knew. It was how I thought. In a world where machines can know everything, the people who thrive will be the ones who can think critically, ask better questions, and help others understand what it all means. Curiosity is what turns history into insight and insight into action. That’s the muscle worth building, now more than ever.
Adam F. Caplan is a technical product leader with a background in logistics, workforce development, and healthcare technology; wellness and fitness enthusiast.