We asked some of the most interesting folks in the community to open up about how they think about taking chances and the role risk has played in their lives and careers. Risk is by far the topic folks talk to us most about and we hope the responses below will help shed light on many different perspectives.

RAWx | Luis Garcia Grech, Orin Torati, Santiago Ceballos, and Dana Shaviv

We’re a team of four architects, who have spent years designing physical spaces. But here’s the thing—we believe the most profound architecture exists in fiction more so than in practice. With a shared sense of an untapped creative outlet, we dreamt of architecting not just buildings, but the very fabric of stories. Read more>>

Michael Johnson

“Burn ships, build bridges.”

I’ve taken a lot of leaps throughout my professional career. I had always been taught to always weigh out the consequences for career changes, relationships, and daily decisions. There are benefits to considering the pros and cons of every major change in your life but over analysis usually leads to decision paralysis. At some point, you have to ‘just make the choice’ and sometimes knowing 70% is better than trying to get to 100%. Read more>>

Raine Roberts

I think there’s a difference between blind risk-taking and informed risk-taking. Depending on where I’m at in life this will influence me either blindly making decisions – perhaps impulsively – or intentionally making decisions. When I was feeling particularly lost, I was open to “larger” risks, or more out-of-character moments. This tends to lead towards a more chaotic style of living, which I have learned I don’t thrive in and it builds to nowhere. I like structure, I need it. However, the chaos informed me on so many important things. It was during this time of chaos that I decided to go back to school, the most structured thing I could think of at the time. Going back to school allowed me to reconnect with my artistic goals and creative passions, and I met so many wonderful people who are now an integral part of my life. Now, I’m living a structured lifestyle with risk taking choices that are informed and are directionally built upon themselves. Read more>>

Haylie Peacock

Throughout a lot of my adolescence, I dealt with severe social anxiety, which prompted my parents to embed messaging of bravery in me. Confidence is a sense of belonging. All you need is the first twenty seconds of courage (thanks, “We Bought A Zoo”), and then you can do anything. Them pushing me to take risks like saying hi to a new person or showing up to a basketball open gym so that I may get a result I wanted – make a new friend or the basketball team – outfitted me with a positive perspective on risk taking. I firmly believe that if something doesn’t scare me at least a little bit, it probably isn’t worth doing. Moving to LA from Montana was a huge risk. I wanted to pursue my career in film and acting, but I had no job, I didn’t really know my new roommate (or anybody for that matter), and I wasn’t sure how I was going to get onto a set. Read more>>

Karla Gudeon | Artist

You won’t ever catch me mountain climbing, sky-diving, bungie jumping, or even walking alone in the woods after dark. I am the person that will trip over nothing and find myself laid out flat, scraped up and laughing on the ground. So I do my best not to put myself in any unnecessary peril. However, even with my aversion to physical danger, I still consider myself a risk-taker. For me, there’s a big difference between thrill-seeking and risk taking.  Compared to thrill seeking, risk taking is…well….riskier.  Read more>>

Alma Ramos | Speaker, Mindset Coach, & DEI Specialist

Taking risks was something that was not encouraged of me growing up. There were many reasons for that. 1. I’m a woman of color, therefore all the messaging around me has been to be cautious and aware of all the danger that lurks around every corner that will take advantage of me. 2. I’m a grandchild of immigrants, therefore any risk I take will not only affect me but could also impact my community. 3. I’m Black and Mexican, consequently the odds are stacked against me for the risks to work to my advantage. 4. I’m a first-generation college student, white-collar worker, and eldest daughter in a BIPOC family, therefore I have the responsibility of leading my siblings and cousins to the “pathway towards success.” So in short, the expectation was to take the “safest” path: get good grades, go to college, and get a stable 9-5 job. Read more>>

Sean Sobash | Musician – Touring & Session Bassist

I’d rather feel the regret of taking a risk and “failing,” than the regret felt of never knowing the outcome of a risk I never took. In saying that I constantly take huge risks, and not all turn out ideally but you learn a lot from every risk and that’s priceless. This goes hand in hand with me not taking life very seriously, and looking at the positive side of experiences. Read more>>

JISEOB LEE | TATTOO ARTIST

All areas of art are the same, but you don’t know how much more time you have to spend to get the results Read more>>

Jennifer O’Neill | Fashion Stylist & Costume

I guess I try to live by the mantra ‘feel the fear and do it anyway’. I believe taking risks is how we grow and if you’re not taking some form of risk then we are in danger of becoming stuck. When I do take a risk and its pays off it brings me confidence if it doesn’t then its a case of having no regrets Read more>>

Sarish Khan | Actor, Producer, Go-Getter!

Risk requires courage, perseverence, and the humility to learn from both successes and setbacks. I don’t like using the word “failure” because I strongly believe that every experience and decision adds value to your life. I come from a background in economics and law, many of my decisions in my life subconsciously run through a cost-benefit analysis. If the projected benefit and value-add of a decision outweighs the financial and emotions costs associated, it’s a YES! Read more>>

Sean Carson | Singer-Songwriter & Artist Developer

The word “risk” is often associated with fear and danger. I’ve always tried to keep an open mind with respect to the fact. Everything we do in life comes with risk. The best risk to take is always a calculated one. Read more>>

Cathy Crosby | “Global Students Science Alliance” Entrepreneur, Writer, Philosopher

I have always been a risk-taker, following my heart, and often at odds with ‘norms.’ For example, during college, I took off to Germany and worked on an island with school children. My family thought I was mad but its value and warm memories have remained with me always. Returning home, I completed a chemistry degree at a Jesuit university of wall to wall males, at a time when companies said straight to your face that they didn’t hire women. I was also a risk-taker in developing a science program in two L.A. schools, got sponsors to donate materials for experiments, microscopes to see crystals and fascinating specimens, and even a Greenhouse to understand ‘The Greenhouse Effect.’ The reward was a school of children with sparkling eyes, who would spot me coming into the school, and line up to hug me and ask, “When is our next science experiment?” Read more>>

Hilary Bilbrey | Co Fonder, People Consultant & Keynote Speaker

Risk-taking did not come naturally to me. I was an adult before I even learned to ski. My husband, an amazing skier, would patiently encourage me down the slopes, as my legs shook in the obligatory pizza shape, and my ego became battered and bruised. Looking down that little green run, it still looked terrifying. I thought of 10,000 things that could go wrong. Meanwhile, my husband, seeing the terror on my face, started falling and laughing next to me. I stared at him, trying to decide if I should be mad or laugh with him. He finally turned back and said, “If you don’t fall, you aren’t trying hard enough. Don’t be afraid to learn to fall, because that is when it gets good.” Sure enough, I took a deep breath, let go, and was skiing double black diamonds by the end of the day. Read more>>

Karan Shah | Producer and Development Consultant

I believe that taking risks is essential for growth and success, especially in the film industry. Embracing uncertainty is a big part of this industry and has always been a part of my journey. For instance, transitioning from a computer science background to film / Bollywood in India to pursuing a career in film in Hollywood was a significant risk. Moving to the U.S. and joining the University of Southern California’s Stark Producing Program required a leap of faith, but it was a risk that paid off, allowing me to work with esteemed companies like A24 and Plan B. Every project I take on involves some level of risk, whether it’s choosing unconventional stories or working with new talent. These risks have been crucial in shaping my career, pushing boundaries, and fostering innovation. My slate of projects all imbibe these values of taking risks. I am currently in post-production with an experimental Bengali short film with elements of magical realism, an Indie drama based in post Roe v Wade Texas showcasing the American landscape through the eyes of two South Asian women, a social thriller, subverting the Romeo & Juliet trope against the honor killings in Haryana to name a few. Read more>>

Nai’vasha Grace | Global Hairstylist & Founder of Curl Queen

Taking risks has been the cornerstone of my journey. Without the audacity to dream, the opportunity to take those risks would have never happened . I moved to NYC with five young children and no solid plan, starting from earning $250 every two weeks in a Fifth Avenue salon with no clients. Through relentless determination, I became an award-winning hairstylist. During the uncertainty of the COVID pandemic, I self-funded my now award winning haircare company. This was all because I dared to dream and take risks. Success demands risk-taking. If you don’t believe in your own brand, how can you inspire others to? Read more>>