Shoot your shot? Take a chance? Society bombards us with messages, phrases, examples and stories of how taking risk is the key to success, but is anything ever that simple? We asked some of the brightest folks we know to tell us about how they think about risk. We’ve shared their responses below.

Rick Shepherd | Actor, Writer & Filmmaker

Risk taking is part of the process. I’ve always taken big risks in my career, a lot of which pertain to location. After going to college in my home city of Cleveland, I moved to London for graduate school and didn’t know a soul. Still I felt compelled to pursue what I thought was the right move at the time. Happily, I can say that my time over there was amazing and the friendships I made were unmatched. Not to mention, the things I learned, along with the personal growth I had, have been massive contributors to the success I’ve seen over the years. Read more>>

Wendy Ortiz | Artist & Craftswoman

My friends and family know me to make seemingly rash decisions – ¡a la voz de ya! (which roughly translates to “do it right now!” I make decisions rather quickly and once I’ve made up my mind, I can usually take action right away. I don’t do pros and cons lists. I rarely ask more than one person for their opinion on something I’m contemplating. And I’ve made “no thoughts, just bops” the unofficial slogan of my life (the quote comes from a print from Los Angeles based artist Ruth Mora). Read more>>

Kirstie Hayden | Comedian

I would say risk taking is one of the foundations of standup comedy. Getting up on stage and never knowing how the crowd is going to respond is incredibly risky in its self. At the beginning your biggest risk is simply not wanting to bomb. Further into the journey, however, several more risk pop up on a daily basis. A few of the risks i have taken so far: trying new jokes in front of large audiences, hours of driving just do an open mic for 4 minutes, going on the road, spending money to do a gig, choosing to work at a comedy club instead of an average day job, and hopping on stage while waiting tables. Read more>>

Carlo Nussio | Tax consultant and Vintege enthusiast

There is no game without risk. For me risk is physiological when you are young, you are more incline to take rash decisions.
Getting out of the comfort zone is the key to growing, that’s what I’m trying to do from day to day, even if it’s not always easy. Read more>>

Sam Donohue | Dancer, Choreographer/instructor, model

I love risk! Calculated risk are great, they open up doors of possibilities. I believe even If you take the risk and fail epically you can learn from that failure and you will have many small wins that you may not notice in the moment, however in hindsight you’ve learned, experienced and grown. This life is about experiencing!! You’ve put yourself in a position you’ve never been before and that requires a different level of self. Let’s say you take the risk and you succeed greatly, you’re still going to have mini failures and wins on that journey. Read more>>

CREEK | artist & songwriter

Risk taking for me, has been crucial. As time goes on and new risks present themselves, I constantly remind myself that they are okay, better yet, necessary. Taking calculated risks can be uncomfortable but I’ve learned that sometimes that’s exactly what we need in order grow and evolve. Everything I’ve been able to experience up until this very moment has been because of the risks I’ve taken, for example, moving to LA from my hometown Springfield, Ma. Best decision I’ve ever made. Read more>>

Ingrid Hernandez | Licensed Esthetician

This whole journey has been based on take risks and taking that leap of faith. It’s so important to not be content and to step into discomfort to grow. Risk taking has been scary because you just never know the outcome you will get but it’s the outcome that made the “risk” that much more rewarding. For sometime, I moved from studio to studio not because of choice but problems in the first building I was in, I could of given up from being overwhelmed with problems but I took the risk of moving and finding a place where I can work out of. Read more>>

Laura Hollis | Founder

I am a calculated risk-taker, and I have always felt this is why I never fit in a traditional job. Without risk, I lose motivation and also experience a lack of enjoyment in my work. Taking risks applies a natural sort of pressure to my day to day work and creates a problem that needs solving. The payoff for managing risk directly impacts my business and therefore my life, so I take huge pride and interest in managing that risk. For example, in 2021 we were having a mediocre year. Read more>>

Nahrin Chowdhury | Education Leader & Entrepreneur

Reflecting on my journey, the younger version of myself would have been shocked to see the fearless risk-taker I have become. Life’s unexpected twists and turns have profoundly transformed my perspective on embracing risks. I grew up in a nice suburban area in New York, raised lovingly by parents who took the ultimate leap by immigrating from Bangladesh in the 1970s. Their experiences, including surviving through wartime, were vastly different from the life they would provide for my sister and me in the United States. They left their families behind to seek opportunities for our future and ensured my sister and I never experienced any feelings of apprehension. Read more>>

Susi Cabello | Podcaster & Entrepreneur

When it comes to risk-taking, I have a clear philosophy: it’s the lifeblood of progress. Taking risks has been the driving force in my life and career. Mistakes and failures? They’re not something to fear; they’re opportunities to learn and grow. I’ve learned to be friends with failure because it’s in those moments that we gain invaluable insights, embrace failure, befriend it, and use it as a stepping stone. Remember, in the game of life and entrepreneurship, if you don’t risk it, you can’t win it. Read more>>

DJ Sammii Blendz | DJ , Instructor , Event coordinator & Entertainment Director

I’m a huge believer in ” With no risks there’s no story” . In everything we decide to do in life it’s all the risks we take in which creates the grand story of your journey . Whether it be risk taking to join that college your not to sure about , jumping into a job you have no experience with , trying to trust your intuition. Down to branching off as an entrepreneur and taking the steps into believing in what you do before you can convince anyone else . It all starts with risks. I started my career as a very young entrepreneur like most teenagers my age it was nothing but a dream I had no idea how to make a reality. Read more>>

Kimberly Butler | Photographer/ Creative Advisor to Brands & Start-Ups.

Deciding to become an artist for a living, is a very risky move. It is not deemed “practical” by almost everyone from family to society. I never gave it a second thought when I decided to get educated in the arts, and follow the one thing I truly loved and never lost interest in. The the most IMPORTANT reason was fear of being locked in an office, dealing with politics, and being a slave to corporate whims. THAT FEAR gave me the energy to push through any obstacle in pursuit of my dreams. Read more>>

Melissa Schainker | Fine Artist and Musician

To be a fine artist is an inherent risk. We’ve all had the term starving artist drilled into our skulls. For me, the rewards always outweighed the risks. At 18, I packed up my car and moved myself 5 hours from my hometown on a full-ride scholarship and a dream. To say being an artist came without hiccups would be a lie. I worked in design for a decade in Saint Louis. I felt this was a more marketable way to use my illustration skills. After that, I worked my way through a graduate program in Web Design and New Media in San Francisco at the Academy of Art University, before my son was born. Read more>>

Kristen Thomasino | Global Humanitarian, Social Good Warrior, Author, Show Host, CEO, Data Scientist

I learned how to play many strategy games as a child. My father loved to challenge my brothers and me to think strategically. We used to play a game called, “Risk.” I started playing when I was 5. I also learned how to play poker around the same time from my grandfather and father. I really believe that their teaching me to take strategic risks through games allowed me to become the risk-taker I am today. Having a career in promoting goods and services plus working on designs for early market products I have had the pleasure of learning about various ways to get business done. Read more>>

Abiodun Koya | Classical Singer & Poet

I think of risk taking as a source of growth, challenge and development. My philosophy is that if you’re passionate enough about your art, you will take risks. Looking at the way, I know I am wired, I am a bona fide risk taker, and I can confidently say that I love taking risks. I am way too much of a curious artist. because I like to see and experience what lies on the other site of risk. When I look back at some of the decisions and steps I have taken so far for my career, I am indeed happy that I took risks, because honestly, they have formed production brands that have come to stay. Read more>>

Lilan Yang | Artist + Experimental Filmmaker

Every decision I’ve ever made has been about embracing risk, pushing the boundaries of my comfort zone, and embarking on journeys into the uncharted. Before becoming an artist and experimental filmmaker, I studied computer engineering during undergrad but I didn’t quite find my calling there. My journey into the realm of creative expression began with a deep fascination for data visualization – I was very fascinated by how different visual presentations shape stories differently. I delved into the world of geographic data, particularly how film locations carried layers of cultural significance when viewed through the cinematic lens. Read more>>

Alexander Heller | Writer-Producer

For whatever reason, when it comes to my life and career I’ve been much more willing to take risks than in other aspects of my life. When I was a kid I literally didn’t step on a crack in the sidewalk for all of elementary school. My parents thought I had problems. Come to think of it….maybe I did have problems. Maybe I DO have problems. But when it came to major decisions like “where do you want to go to school” or “where do you want to live” I would- for lack of a better term- YOLO it. I know nobody says YOLO anymore. Read more>>

Julissa Serrano | Beauty Product Developer

When it comes to risks, I tend to focus on the aspect of my career. Taking risks has unlocked cumulative rewards and career success for me. Over the years, I have taken many risks, but nothing can compare to making the big move to California from the East Coast to focus on my career in the beauty industry. At an early stage of my life, I analyzed the risks and rewards of a big move across the country. Despite the lack of friends, family and job leads, I realized that to change my life drastically, I must make drastic changes. Nothing truly prepares you for the long journey ahead. Read more>>