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.

Ariel Walker

Taking risks has played a major role in my life and career. I believe growth happens when you step outside of your comfort zone and pursue opportunities that challenge you. One of the biggest risks I’ve taken was pursuing acting later in life while balancing other professional responsibilities. There were no guarantees of success, but I knew I would regret not trying. Read more>>

Alfio Longo

Risk is an essential part of creativity and innovation. Without risk, there is little opportunity for growth, excitement, or meaningful achievement. However, risk should never be taken blindly—it must be calculated and evaluated based on the vision, goals, and desired outcomes. Throughout my career, particularly when developing new restaurant concepts, I have learned that every decision involves a degree of risk. Read more>>

Ramiro Gastelum

i think taking risk should be something people try way more often. it’s exciting to push these new boundaries and see where that can take me. Taking risk has been something i’ve practiced since i was little, and i think it’s shaping the way i create and think in my life. Read more>>

John Stanley

I suppose I have always been pushing boundaries when it comes to taking risks. In my younger years, I enjoyed all things having to do with speed and racing, so in the summers I raced motorcycles, eventually at the professional level, and in the winters I enjoyed downhill ski racing and became pretty good at that as well. Read more>>

Lindsay Luttrell

Risk has played a major role in my life, both personally and professionally. It’s funny because I wouldn’t actually classify myself as a risk-taker, but looking back, I wouldn’t be where I am today if I hadn’t taken so ​m​any leaps of faith. Read more>>

Jennifer Sims

I don’t think of risk as something typically dramatic. It’s more about staying aligned with my Creative vision and goals. In this industry, one of the biggest risks can be staying in situations that no longer serve you or reflect your value just because they feel familiar. Read more>>

Tamara Gould

Risk has been ever present in my career as an artist and graphic designer. I feel like most of what I endeavor comes with uncertainty – will this work? how can I make it work? how will it be received? Read more>>

Nidhi Naroth

I think anyone would tell you having a career in art is a gamble. Making a living as an artist is far from easy. The industry is always in flux, and when the waves come crashing down, it’s tough to keep your head above water. Read more>>

Ava Crozier

Risk has completely shaped both my life and my career. I honestly believe that every major turning point in my life has come from being willing to leap before I felt fully ready. At eighteen, I made the decision to move alone from Australia to Los Angeles to pursue acting professionally. Read more>>

Rebecca Cox

I mean, like so many of us, I’ve had a complicated relationship with risk in the past, but the more you work that muscle, the stronger it is and I think it’s really just about having a foundation of trust in the concept of the unknown and understanding it won’t swallow you whole, moving forward in spite of trepidation. Read more>>

Rita Aldridge

When I was 19, I got on a flight from my home in London to LAX with little to no plan. Nine years later, I consider Los Angeles my home. That leap of faith allowed me to discover the life I had always dreamed of. I got sober, applied to art school, and this May graduated with a BFA. Read more>>

Cat Sherwin

One thing I’ve learned is that growth and risk are inseparable. Every major chapter of my life and career began with a leap of faith. I left a successful corporate career in the UK to completely reinvent myself in Australia and retrain in the beauty industry from scratch. Read more>>

Justyn Caze

Risk, as a drag performer, is part of the job. We have a very unique position. We are usually the first thing people see, the people rallying the crowd. We inspire and take the brunt of the heat since we are what prejudice folks see. As a public figure, in a sense, we are also in the crowds interacting with folks. Read more>>

Morgan Tomasetti

Risk taking is perhaps the most essential thing to do when you are working toward your dreams. Big dreams and goals must be supported by actions, and any action that will actually get you to where you want to be is likely out of your comfort zone, thus involves some sort of risk. Read more>>

Isabella Knight

I’ve discovered that risk-taking in my personal life is directly tied to my creative process. I’m naturally impulsive, so I don’t hesitate to do things that feel unexpected or unconventional, and that’s usually where my best songs come from. Being fearless, and sometimes even reckless, has led to some of my strongest creative moments. Read more>>

Alice Kao

People often tell me that I’m a big risk taker in business, but honestly, I don’t really experience it that way. When I believe deeply in something, I have a tendency to talk myself into it so completely that I stop seeing obstacles as reasons not to do it. I just see them as problems that need to be solved along the way. Read more>>

Cassandra Hepburn

Risk Didn’t Make Me. Redemption Did. They told my mother not to have me. Let that land for a moment. Before I ever drew a first breath. Before I ever made a single choice. Before I knew what risk even was — I was already one. I was the risk my mother was told not to take. And she took it anyway. Read more>>

Marissa Alaníz

I love risk, I love mistakes! I have always been a big believer that failure and discomfort are where the most growth happens. If something seems a little scary to me, I feel that I am more inclined to run towards it and not away from it because it is often rewarding. Read more>>