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.

Simone Leon

I’ve taken a lot of risks in my life, making an abrupt career change in order to pursue a life as an artist. To a lot of people it seemed crazy, unwise, and out of nowhere. I have had people tell me they never imagined that I would become an actor. Read More>>

Adam Francis Scott

Risk is the main engine of my art practice. Painting is risky. Going to the studio every day is risky. Painting serves no purpose other than delineating porous zones of becoming. The artists I look up to, have all taken major risks with their work. I see risk as an ethical necessity within my studio practice. Read More>>

Davyd Markovich

We have one beautiful, complex life, at least as far as we know. The idea of reaching the end of it and realizing I never jumped off the highest diving board is far more terrifying than the ten seconds of free fall. I think about risk all the time. In my pursuit of happiness, I’ve chosen to dive headfirst into an artist’s life. Read More>>

Zanele ZIMU

I think risk is one of the most important parts of growth especially in a creative career. If I hadn’t taken the risk of putting myself out there as both a model and an actress, I would’ve missed out on some of the biggest moments of my journey so far. Read More>>

Ann-Christin Brune

I’ve learned that the artistic path isn’t always bright or easy. There are times of struggle and uncertainty — but those moments are opportunities for growth. Seeing challenges as chances to become stronger and better has shaped both my mindset and my art. One of the main themes in my work is this: There is a strength, an inner light within you. Read More>>

ilayda celebi

I’ve always believed that real growth happens outside of your comfort zone. I was born and raised in Istanbul, Turkey, and when I was 18, I decided to move to Russia to study art in a completely new environment. I didn’t know anyone there, and I wasn’t familiar with the language or culture, but I immersed myself fully. Read More>>

Ranella Ferrer

If it wasn’t for risk, I wouldn’t be here. My whole life has been a risk, from leaving the Philippines to chase my dreams in Los Angeles, to stepping on stages without knowing where the next opportunity would come from. Every major moment in my career came from betting on myself when no one else could see the vision yet. Read More>>

Armida Lopez

Taking risks has been part of every decision I have made to get to where I am now. The first risk I saw was my mom taking a risk to move from another country of El Salvador to move me to the United States when I was 9 years old. Read More>>

Ruben Sebban

I love my career as a film and TV editor, and honestly, I wouldn’t be where I am today without taking risks. The biggest one? Leaving a steady job as a sports editor in the Netherlands to move to the U.S., where I knew absolutely no one, to start over as a student at the American Film Institute (AFI). Read More>>

Sade Moore

Since taking chances is a big part of life, I believe it’s necessary to do so. Try new things; go after what you desire. Failure is something you cannot escape. Most individuals, I believe, dislike taking chances, but I have done so on multiple occasions in my life, both in terms of my education and my career. Read More>>

Bud And The Night

For me, risk has always felt less like stepping off a cliff and more like stepping into the unknown with a sense of wonder. Bud and the Night is built on that—on exploring new worlds, new sounds, and new parts of myself. Read More>>

Evan Bergman

I like to quote Bob Dylan “When you ain’t got nothing, you got nothing to lose” This sentiment removes the risk of failure. Emotional support from family and friends is also everything. Read More>>

Alice Castro

What is art without risk? As an immigrant, one of the biggest risks I’ve taken is leaving everything behind at home to move to a new country and pursue my dreams. Read More>>

Tramar Mercadel

Risk-taking has always been a major part of how I grow, both personally and in my career. I look at risk as an opportunity—something that can either push me forward or teach me a lesson that sharpens me for the next step. I don’t take risks blindly, but I also don’t let fear stop me from moving toward something that could elevate my life. Read More>>