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.

Vera Jigalova

I’ve always embraced risk — it keeps me sharp and on track. I move a lot, I dive into new environments, and I consistently take on projects outside of my comfort zone or without prior experience. That’s where I grow the most. Risk has played a huge role in shaping my career — it’s pushed me to learn fast, adapt, and trust my instincts. Honestly, without risk, I wouldn’t be where I am today. Read More>>

Jacquelyn Frohlich

Risk taking has been integral to my life and a determining factor to the opportunities that have come my way. This is as true in my personal life as it is in my career. I am not quite reckless though, but almost. Read More>>

Erik Fellows

I’d say that I have taken huge risks from an early age and constantly challenged myself and tried to get over my own fears and lacking of confidence. Over the years I’ve had a lot of success but also a lot of failure. I struggled with a lot throughout the years. Having money, going broke and repeating the process hasn’t made any easier either, also being in the position of your career taking off multiple times and being let down, you start to question if you’ve made the right choices and if this is the right career path for you. Read More>>

Keenan Ysaguirre

With no risk there is no reward . That quote changed my life at 13 years old . While I never quite fully understood the magnitude and depth of it; it’s a mantra I’ve basically followed and kept alive within self all these years . I feel risk is important, everywhere your eyes touch there was someone doubting someone’s risk to take things somewhere not seen, felt, heard or experienced before . Risk taking has been extremely beneficial throughout my life and career; I guess now at this point in time of my career I’m just able to make better sense of each of them . Read More>>

Randeep

For me, risk has never been about adrenaline—it’s always been about alignment: spiritual alignment, personal truth. I’ve never been someone who takes leaps just to feel alive. I take them when something deep inside me insists that I must. It’s an inner push, sometimes a whisper, other times a scream. And I’ve learned to listen to that voice, even when it makes no logical sense. Especially then. Read More>>

Iveth Rodriguez

For me, risk is a mix of temporary feelings. I’ve come to realize that making mistakes is part of the process… I mean, what’s the worst that can happen? I used to get stuck even before hearing no, and that held me back, kept me in my bubble. Read More>>

Dan Balcaban

Risk has been a part of my life since I was a teenager growing up in Australia in a single-parent household. Just surviving paycheck to paycheck was a kind of risk — one we didn’t choose, but had to navigate daily. My brother and I worked minimum wage jobs and supported each other through that uncertainty. So I learned early on that risk wasn’t optional — it was how you moved forward. Read More>>

Alex Peña

Risk has always been a part of my life. The way I assess risk and choose to act on it has definitely shaped my life and the decisions I’ve made—personally and professionally.

I believe risk is what marks the difference between fulfilling your dreams and reaching your goals, or spending your life haunted by “what if” scenarios. Read More>>

Ana Milena Rojas

Risk has shaped every chapter of my career—it’s honestly how it all started. I got my first job in the industry just ten days after I started studying design. I had no real knowledge yet, just curiosity and the decision to jump into the deep end. I figured, why wait? And I’ve been learning on the spot ever since.

Every project I take on is one where I’m still a student. I never really know if it’s going to work or what it might lead to, but I’ve learned that without taking that risk, I wouldn’t be where I am now. I’ve always said, “We all carry a NO in our pockets, so we have nothing to lose.” That mindset keeps me moving—keeps me saying yes even when things feel uncertain. Read More>>

Anni Spacek

Risk-taking, for me, is inseparable from curiosity. As a documentary filmmaker, my work lives at the intersection of storytelling and truthtelling. The medium is inevitably subjective, yet grounded in a pursuit of authenticity—a grey area I’m drawn to. I gravitate toward ideas that feel a little risky or uncertain, and it’s in those moments that I want to point my camera. Read More>>

Jenna Lee

I see risk-taking as closely connected to imagination and creativity. When I stay within what I already know—things that feel safe and familiar—the results tend to be just as expected. There’s comfort in that, but not much room for surprise or change. I’ve found that real creativity often begins just outside that space—where the outcome isn’t certain, but there’s room to discover something new. Risk makes that space possible. It asks us to let go of what we know and follow curiosity instead. Read More>>

Austin Warnock

I feel like risk taking is a necessity. Fear is often times the single biggest thing that holds people back from taking risks or taking action and pursuing their passions in life. I feel like I’ve taken a lot of risks in life, and have often found that things work out, because even when they do not seem to, you still learn a lot in the process and it is very valuable to learn along the way. Read More>>

JAYASHREE

Ultimately, I’m not going to glorify risk or pretend that I love it. I don’t walk into uncertainty without fear I still get shivers down my spine, I still wrestle with self-doubt. But the key thing is: I don’t let it stop me. Read More>>

Bre Gonzalez

I think that I am a risk taker. A lot of owning your own business is a huge risk. This business can be feast or famine at times, depending on the time of year. This is not a career for the faint of heart. I’ve never been afraid to try something new, even if I don’t really know what I’m doing. I almost get a thrill out of it. But you have to be somewhat of a risk taker to be a Colorist. It’s how I’ve become the Hairstylist that I am today. Read More>>

Vincent