The Hidden Power of Career Zigzags

As a professor at Brandeis International Business School and host of the "From the Dorm Room to the Board Room" podcast, I've had the privilege of interviewing hundreds of professionals about their career journeys. One pattern consistently emerges: the most successful careers rarely follow a straight line.

The Power of Unexpected Beginnings

Take Jim DeCicco, who graduated from Colgate as a philosophy major and writing minor. He never planned to become a beverage entrepreneur. Yet those seemingly unrelated liberal arts studies, combined with his experience as football team captain, gave him the perfect foundation for building Kitu Life Inc. As Jim told me, "Really, the only way you learn and grow is by doing hard things — hard, uncomfortable things."

The Value of Productive Discomfort

One of my favorite interviews was with Ryder Carroll, creator of the Bullet Journal. His story perfectly illustrates what I call the "productive discomfort zone." After graduating with degrees in Creative Writing and Graphic Design, his planned career in music video directing evaporated. He found himself in post-9/11 New York, taking a job he disliked at a publishing company. But that very discomfort pushed him to explore web development on the side, eventually leading to his creation of the Bullet Journal method.

The Beauty of Career Experimentation

Sarah Green Carmichael's journey from Brown University to becoming an Executive Editor at Harvard Business Review demonstrates something I consistently see in successful professionals: the willingness to experiment and pivot. She tried teaching, retail, and freelance writing before finding her path in business journalism. As she told me, what seemed like "selling out" for a steady paycheck turned into a 12-year journey she loved.

Key Patterns I've Observed

Here's what I tell my students based on these real-world examples:

1. Start Before You're Ready As Jim DeCicco says, "Don't wait until you're qualified. Don't wait until you're ready. Just get going, because the real world is going to validate your idea."
2. Secure Your Base Ryder Carroll's advice resonates here: ensure you have basic financial stability before pursuing entrepreneurial ventures. You can't do good work when you're constantly dreading rent.
3. Value Transferable Skills Sarah's experience shows how skills like empathy, developed through studying literature, can become leadership assets in unexpected ways.

The Real Lesson

The key isn't finding the perfect path – it's making the most of each experience and remaining open to unexpected opportunities. As my podcast guests consistently demonstrate, the most interesting careers are built on the foundation of diverse experiences, willingness to adapt, and courage to take calculated risks.