In a world where we’ll spend nearly 80,000 hours at work, how do you choose a career you won’t regret?
That question was at the center of a recent fireside chat hosted by the NYU Stern Berkley Center for Entrepreneurship featuring Bill Gurley, general partner at Benchmark, in conversation with bestselling author and journalist Malcolm Gladwell. Inspired by Gurley’s new book Runnin’ Down a Dream, the discussion explored why so many people end up dissatisfied with their careers, and what it actually takes to build one rooted in curiosity, purpose, and long-term fulfillment.
The conversation ranged from the stories behind Gurley’s book to broader reflections on ambition, mentorship, and experimentation early in one’s career. Gurley shared examples of individuals who built extraordinary careers by pursuing deep interests and starting at the lowest rung of their industries, while Gladwell reflected on how observing people who genuinely love their work can shape how others think about their own professional paths.
A recurring theme was the power of curiosity. When someone is fascinated by what they do, Gurley explained, the learning becomes energizing rather than exhausting, creating an advantage that compounds over time as enthusiasm attracts mentors, collaborators, and new opportunities.
The conversation sparked thoughtful questions from students, founders, and members of the broader NYU community, touching on everything from career experimentation and mentorship to how emerging technologies like AI may reshape the future of work. Gurley encouraged attendees to stay curious, seek out environments where they can learn from others, and remain open to the pivots that often lead people to the work they ultimately care about most.
The evening drew an extraordinary turnout. Close to 600 guests filled Stern’s Paulson Auditorium to watch the conversation unfold. When the discussion ended, the excitement didn’t, the line to meet Bill and have him sign copies of Runnin’ Down a Dream stretched out the door. He stayed well after the event concluded to meet attendees, talk with students, and sign books for everyone who waited, keeping the energy of the night going long after the final question was asked.
Tips & takeaways
- Curiosity fuels great careers. When you’re genuinely fascinated by a field, the learning becomes energizing rather than draining.
- Start anywhere, but start learning. Many impactful careers begin at the lowest rung with a focus on mastering the fundamentals.
- Seek mentors close to you. The most valuable guidance often comes from people just a few steps ahead in their careers.
- Experiment early. Trying different paths early in your career helps you discover what truly energizes you.
