Are you a risk taker? Do you think you have a stronger appetite for risk relative to your friends and family? We asked some folks from the community about their approaches to risk and have shared their thoughts below.

Erla Dögg Ingjaldsdottír & Tryggvi Thorsteinsson | Founders

If you don’t make mistakes, you’re most likely not making decisions. An educated risk is necessary in both life and growth.. Life as a person, life as a person building a company. Read more>>

Arielle Werblun | Licensed Marriage and Family Therapist

Taking risks is a concept that was once foreign to me. Having grown up in a household where fear and anxiety were prevalent emotions, stability and surviving took more precedence than did taking any sort of conscious risk (whether that be academically, professionally, interpersonally, what-have-you). The idea of pushing limits was awesome; the implementation of it, however, was another story for a long time… It wasn’t until I was in my late twenties that I realized how much risk I actually wanted to take in multiple areas of my life – professionally, most prominently – yet I was keeping myself from doing so. Read more>>

Iona Holloway | Coach & Author

I prefer to think of risk as choosing to be brave. Being brave is choosing to take action in the absence of evidence that your efforts will pay off, or guarantee success but choosing to try anyway. Being brave is something I’ve always been, although I think the energy behind my bravery has changed over the years. I took a massive risk at age 20 when I accepted a field hockey scholarship to play Division 1 field hockey at Syracuse University and moved to the US from my home country of Scotland having never visited before. My coach took a big risk on me. She’d never even seen video of me play. I was brave in that moment because I wanted to escape a life I was struggling with at home. I was struggling with disordered eating and a clean break felt brave at the time. In hindsight, perhaps I was running away. Eight years later I finally cashed in all my bravery to heal my relationship with myself, my food, and my body. Read more>>

David Sheftell | Actor & Voice Actor

As an Actor is has been proven to me time and again that risk is an essential part to anyone looking to venture into a life in the entertainment industry. You take a risk every time you walk out on a stage, in front of camera, in front of an audience, or even just doing an audition. You risk a little part of yourself, and that risk can lead to wild success or tremendous failure. There is one particular instance in my life where I took a pretty big risk and it changed my perspective on the idea of it from that point forward. It was my freshman year at Pepperdine University and I was a brand new Theatre student. At the beginning of the year, you audition for two shows, the Musical which is on the main stage and a drama in the Black Box Theater. The auditions go on for several days in the very first week of school. Read more>>

Charlie Waymire | Recording Engineer & Producer

In the music business everything is a risk. Personally I try not to think too much about what may be a risk or what isn’t. That kind of thinking can keeping you spinning in circles. Obviously there will be some things that are more risky than others but taking risks is a part of anything that is worth doing. If I have an idea for my business I spend more time figuring out if it fits what I’m trying to accomplish. If it doesn’t then I throw the idea out but if it fits I find a plan of action and just go for it. When it works it’s great. When it doesn’t I figure out why, learn from it and move on to the next thing. For me it’s all about action and once that becomes a habit risk isn’t really a factor anymore. You just do it. Read more>>

Billy Kirsch | Grammy and Emmy Nominated, CMA and ACM Award Winning Songwriter, Team Building Facilitator & Interactive Keynote Speaker

As a life long creative, it rarely occurs to me not to take a risk when I’m excited about something. I think I became addicted to risk taking when I began white water canoeing as a kid. Before every river trip, I’d be filled with dread, self-questioning why I’d put myself at risk when I didn’t have to. But I soon learned the thrills that came from navigating the white water and the uncertainty always paid off. In my business life, I’m not a crazy stupid risk taker but when it comes to the big things, I always follow my gut to explore new ideas and if those ideas or challenges seem like they might lead somewhere interesting I’ll go for it. It generally pays off. Falling down a lot, but always getting back up – that’s the key to making things work in the end. Read more>>

Scott Asai | Keynote Speaker

No risk. No reward. That’s a quote that’s stuck with me for several years. I’d like to consider myself a “calculated” risk taker which means I tend to compete in areas I have a good chance at succeeding in. For me risk usually includes relationships: work, personal and family. Investing in people initially is like jumping off a diving board not knowing if there’s water below. Sometimes it works out great and other times you get burned. But life always includes risk no matter what you do. One of my favorite sayings is: I can live with failure, but I cannot live with regret. That must be why I resonate with Nike’s motto “Just Do It.” I’d much rather try and fail, than look back on my life and regret not giving it a shot. The most successful people in any industry fail more than they succeed. The difference is: they don’t let failure stop them. They treat it as a learning experience. I will continue to take risks in both my personal and professional life because without taking risks you’re not truly living! Read more>>

James Ken Blackmon | Actor, Producer & Entrepreneur

I see risk as being absolutely necessary to achieving a life well lived. There’s an abundance of different levels of risk, and I truly believe “the bigger the risk the better the reward”…Growing up I had a disproportionate amount of people around me playing it safe. No one was actively pursuing their dreams, which always leads to bitterness and regret however small. So I promised myself I’d never shy away from taking big risks. In my opinion the pain and regret from never stepping up to the plate at all, was greater than the fear of staring down the pitcher. My life and career are both intertwined with this core belief, everything from motorcycling in Africa, to acting in Hollywood. Read more>>

Mo Maravilla | Founder & Roaster

Risk taking has been a constant in my life. My parents always wanted me to be a doctor or a lawyer, or work a well-paying corporate job, but I was never drawn to such things. I always wanted excitement and non-routine, which led me to be a stagehand and an audio/visual engineer. Once that stopped road stopped giving me fulfillment in life, I looked to start my own business. I view risk taking as it relates to the wholeness of my life, not just financially – how much does this mean to me, will I regret not pursuing this dream? I assess risk within the context of in happiness and meaning in life, never in dollars. It’s never been easy choices or paths, but I’ve never regretted anything I’ve chosen and I know the life I lead is completely my own. Read more>>

Devin Callen | DJ & Music Producer

Taking risks has played a massive role in my career thus far. I would say dating back all the way to 2013. This is when I knew music was what I wanted to do. I attended my first EDC Las Vegas and was instantly hooked. It was during this exact weekend, I looked up at the DJ and told myself in my head, this is exactly what I want to do and that I as going to do whatever it takes to achieve that goal. Let me tell you a little about some of the risks I have taken to get to where I am at today. In 2014, I discovered a school called Scratch Dj Academy located in Los Angeles. I instantly wanted to attend! I showed my parents, and they were fully supportive. I love them to death for allowing me to chase my dreams and to this day am forever thankful for their support. However, nothing was just handed to me. They wanted me to follow my passion, but in order to do so I needed to save up the right amount of money. Read more>>

Ritzy Periwinkle | Creative & Story Teller

I think of risk as something that pays off at the end regardless of outcome. You either get the desired outcome or you don’t and you learn from that. Being a creative means constantly taking risks. I left my well paying music industry job back in 2006 to start Ritzy Periwinkle. Since then I’ve traveled and exhibited around the world, been able to pivot into different creative roles and during this pandemic, took a risk to launch another podcast, Word To Your Mama. I feel you can’t make progress on your dreams if you’re not taking risks. Read more>>

C. James | Singer Songwriter

Ever since I first began making music, I have been deeply insecure and self-conscious of sharing my songs with anyone. I have always been anxious with the thought of taking any major risk to pursue music full time as a career. Instead, I went to college and chose what I thought was a safe career in teaching. This ended up being great as I realized that I loved to teach and watch others grow. However, as life experiences mounted, my desire to share them through song grew. It wasn’t until recently that I began taking more risks with sharing my music (at the strong encouragement of one of my best friends and producer Peter Fenn). My point is, not everyone is programmed to drop everything and chase their dreams. Some people are like me, and learn to accept risk taking as part of life. Either way is perfectly fine. Read more>>

Kaleena Sales | Design Educator & Author

Risk taking means making myself vulnerable. As an author, I write about my intersectionality of being Black and a woman; specifically as it relates to my work as a designer and an educator in an industry that is largely White, and historically underrepresented in minority voices and experiences. In sharing my experiences about teaching at an HBCU (Historically Black College and University) and challenging the industry to expand its view on what defines “good” design, I undoubtedly open myself up to criticism and opposing views. As intimidating as it can be to reveal uncomfortable truths, I find that when I’m honest and open about the challenges of navigating as a minority, most people respond with open hearts and minds, allowing ideological bridges to be built, and authentic relationships to flourish. Read more>>

Lilia Gonzales Chavez | Arts Administrator & Culture Bearer

I do not think of myself as a risk taker. I do not gamble, and I don’t engage in skydiving or mountain climbing because of the risk involved. Yet, risk has been present in many aspects of my career. I think of it as the only way to advance. Whether it is changing jobs or developing a new program a degree of risk is always present. Calculated or unexpected, risk is exists. It is how you approach it and limit your exposure that make the difference from failing or succeeding. Being flexible, able to shift thinking and adjust to doing things a different way and adapting to that new way help minimize the possible negative impact of risk taking. Read more>>

Nicole Holmes | Actress & Filmmaker

Taking risks is one of those things that walks a fine line between success and failure. You commit to taking a risk once you let go of the idea of failure, knowing full well that you may slip and fall. We are afraid of falling and with good reason, falling hurts. It’s when we begin to remain complacent in a world of comfortability that risk is essential for growth. I consider myself someone who is uncomfortable unless I’m continuously trying to better myself and with that comes great risk or what I like to call “a leap of faith”. The idea of leaping and not knowing where you will land is scary, but also exciting. Seven years ago, I took that leap and made the move out to Los Angeles to pursue a career in film and television. I got in my tiny Kia Rio and drove cross country from Rhode Island for a dream. Read more>>

Grace Scuitto | Photographer

My life has been a gamble, entirely driven by a mission to evolve personally & professionally. Every risk requires some level of sacrifice. 9 times out of 10 the outcome is totally worth it and if it’s not well, then you have a better understanding of what you don’t want, and knowledge of self is power. Nevertheless, you learn and grow and that’s what life is all about anyway. Read more>>

Jamie Pesanti | Airbnb Superhost, Boutique Owner & Nomad

I didn’t always know how to take risks. I usually played it safe which is how I ended up making multiple mistakes following my head, more security, and not my heart. I knew that my time as a 5th grade teacher had come to an end after 20 years when I spent all the way to school and back thinking about what was next for me. Don’t get me wrong, teaching was fulfilling and rewarding and I loved so many things about my job. But I knew there was more for me and a next chapter. What I didn’t know was how to do it. It seems I had become an expert of knowing what I didn’t want in life but uncertain as to what was next for me or how to get there. I spent a couple years really dreaming, thinking and stewing about what I could do to combine my talents and adventurous spirit. It didn’t all come together magically one day. Read more>>