By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Lucy Robinson

Risk-taking has played a huge role in my life and career because I’ve realized most people live controlled by fear, especially fear of the unknown. Leaving stability to work for yourself is scary and full of uncertainty, but growth only happens when you step outside your comfort zone. Some of the biggest breakthroughs in my life came from doing things I once thought were impossible. Read more>>

Via Monk

I actually think people are sometimes surprised by my answer to this because in my personal life, I’m not naturally a huge risk taker. Even with things I enjoy like snowboarding or other more extreme activities, I’m still very calculated and focused on safety, preparation, and minimizing unnecessary risk. That mindset honestly carries over into business too. I don’t view risk as being reckless. Read more>>

April Washinowski

I think risk has played a huge role in both my personal life and career. I’ve learned that growth usually comes from stepping into situations that feel uncertain but aligned with your bigger vision. For me, risk-taking has looked like entering highly competitive spaces, building and expanding businesses, stepping into leadership positions, and trusting myself enough to learn as I go. Read more>>