Unlearning the Grind
A year of experiments, dead ends, reinventions, and unexpected beginnings
Everyone knows about the “gap year” you take between high school and college. I decided to take mine in my late twenties.
Since moving to the U.S. in 2017, I’ve been in what the internet lovingly calls the grind: an MBA, early employee at three startups, and then Associate Director at MIT’s Entrepreneurship Center. By October 2024, I finally paused long enough to ask myself: What do I actually want to explore if I give myself a year?
The year started beautifully. I ran two AI workshops for high school students in Boston at one of the oldest public schools in the country. Then I reconnected with an old friend who became my co-founder. Together, we explored a simple insight: everyone wants to learn AI, but few know where to start or how to build real, career-advancing skills.
After helping build an AI tool at MIT that unexpectedly reached 13,000 users in its first year, I was eager to bring those learnings to the workforce. So we began.
I did over 120 user interviews. When we launched, 350 people signed up in the first two months. But then came the hard part: finding a business model. End users loved it. Business leaders didn’t see it as mission-critical. It became a “nice to have,” not a “must have.” We even had professors using it to evaluate their students’ AI skills, but translating interest into revenue was tough.
Four months in, I pitched at New York Tech Week. The ecosystem loved the idea but validation didn’t translate into traction. We interviewed with every major accelerator we applied to—Pear, Techstars, Neo, and others—but we were still too early, still figuring out the GTM. Eventually, when the runway ended, so did the co-founder chapter.
That’s when I learned one of my most important lessons: I had the product and engineering chops, but not the go-to-market muscle. You can build the best product in the world, but if you can’t sell it, it doesn’t matter.
So I reached out to a founder I had met only once but deeply admired, and pitched myself as their GTM lead. Ten days later, I was leading GTM at a Series A company selling into pharma and health insurance.
The past four months have been a crash course in everything I was missing: customer segmentation, ICP definition, speaking with experts across pharma and biopharma, building partnerships, crafting GTM motions, and running campaigns for beta programs. It’s been an intense, humbling, energizing education.
As the year comes to an end, I can honestly say: this was one of the best years of my life. A year of learning, unlearning, and growing. My late-twenties gap year didn’t take me to a new country but it took me exactly where I needed to go.