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Aaron Levie, the co-founder of Box, offers simple but powerful advice for entrepreneurs: If you feel comfortable, you're probably not doing it right. Business is full of tough decisions—who to work with, how to compete, whether to raise money, or even whether to drop out of school. Levie believes that discomfort is a natural part of the process and often a sign that you’re pushing yourself to grow.
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Why Being Uncomfortable is a Good Thing
In Levie’s view, when you’re stepping outside of your comfort zone, you’re entering the space where real growth and innovation happen. It's when you're unsure, facing tough choices, and wrestling with uncertainty that you’re most likely on the right track. Those moments where you take a leap without knowing the exact outcome are crucial to personal and business growth.
Examples of Entrepreneurs Who Embraced Discomfort
One less well-known but successful example is Lynda Weinman, co-founder of Lynda.com (later acquired by LinkedIn). She left her teaching job to start an online learning platform at a time when the idea of e-learning was still new and unproven. She had to make tough choices, like betting her future on an untested market, but that leap into the unknown paid off.
Similarly, Chris Barton, co-founder of Shazam, was working a comfortable job at Google before he ventured into the music recognition business. He faced the difficult decision of leaving the security of Google to build a product that many thought was impossible at the time. His discomfort with the decision turned into success, as Shazam became a revolutionary app in the music industry.
Making the Leap
Levie’s message is clear: if everything feels safe and easy, you're likely not pushing hard enough. It’s the tough calls and the uncertain moments that challenge you to think creatively and take risks. And, as we've seen with entrepreneurs like Lynda Weinman and Chris Barton, those uncomfortable decisions often lead to the most rewarding outcomes.
Listen to Aaron Levie:
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