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. 

Rebecca Stieb

Before founding my nonprofit, I did not consider myself much of a risk-taker. Looking back, though, I have realized that some of the best chapters in my life were the direct result of a leap-of-faith moment. In 2022, I made the decision to leave my 13-year career to start my own organization. Read More>>

Emily Menegatti

I believe that if you’re not taking chances, you’re not growing. Throughout my life and career, I’ve learned that real progress happens outside your comfort zone. I’m naturally driven and goal-oriented, so I’m always looking toward the next challenge or opportunity. When things feel too comfortable, that’s usually my cue that it’s time to push myself, learn something new, or take on a bigger responsibility. Read More>>

BRICE Young

I’ve learned that meaningful opportunity almost always lives on the other side of risk. Entrepreneurship has brought its share of stressful moments, but it has also delivered some of the most rewarding experiences of my life. Read More>>

Moses Chavez

The biggest risks I take are with cash flow. I’m willing to put myself in uncomfortable positions by reinvesting back into the business to get hard assets. It’s not always easy, but those calculated risks have consistently led to growth. As we invest, we’ve seen our cash flow expand, which reinforces that stepping outside of comfort is necessary to move forward. Read More>>

Laurie Pokin

When I sit down to write, in fact, when I’m thinking about sitting down to write, there is a thought (almost every time) that ‘no one will ever read your writing and if they do, they’ll either dislike it, or worse, not care anything about it! You’re wasting your time, this is pointless!’ Those things are risks I must take because I must write. Read More>>