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.

Kelley Katharine | Owner-Custom Home Staging Designer

I was at a crossroads in my life. Newly divorced at 50, last 22yrs in the home raising my children. Needed a new financial vision to create stability for myself and my family. Challenging to find career opportunity with my 20 plus year resume gap. Read more>>

Kammy Burnett | Comedian, Actor, Filmmaker

So many people spend too much time dreaming about what they want in life. And how things could be better. Unfortunately, most never even start the pursuit. Perhaps, because of anxiety and fear. I believe you must take risks in life so you don’t have regrets in the future. We all fail. But we must keep taking risks. Read more>>

Sean Murphy | Photographer

In the beginning… I was a terrible student and floundered a lot until about the age of twenty. A photography class at a community college in Orlando was my first introduction to the craft. The professor advised me to move away and try and go to school in Boston or NYC. I packed up all my stuff and moved to Boston without a plan other than I was going to try and get into a school there. Read more>>

Yasmin Pascall | Actor, Martial Artist, Dancer

For many years, I was taught that I had to wait for someone to open a door for me and tell me I was worthy of being in the room. I have found that the only approval I need as an artist and human is from myself. I am invested in unleashing the inner child; that bold, honest. Read more>>

Jeffrey Reddick | Screenwriter, Producer & Director

My career is in entertainment, which is one of the riskiest career paths to pursue as it’s really hard to break into. But despite all of the people who warned me I was making a big mistake, I took the risk anyway. It was definitely a difficult path. In an industry where the competition is fierce, the industry is constantly evolving and there are no guarantees. Read more>>

Kwesi Mance | Comedian

I think that risk is just whats required of you to be able to get what you want in life. Nobody has gotten anywhere they wanted to be without risking something. Also, I believe risk is something you cant avoid weather its sacrificing stability to pursue your dreams or sacrificing your dreams to maintain stability. Read more>>

noé olivas | Artist & Educator

Taking risks has always been a challenge for me. It can be hard for me to make decisions at times. What has been helpful for me in those moments are to check-in within myself and ask these questions: 1) Can I afford to take a risk? Am I in a healthy position financially, mentally, physically, and spiritually to make a clear decision? Read more>>

Danielle Lindenlaub & Kim Jay | Photographers at Ethos Imagery

Navigating risks in our career and lives has ultimately brought us to where we are today. First off, taking the entrepreneurial ‘road less travelled’ is a risk in and of itself. Trusting our vision is crucial, even when things feel uncertain. Read more>>

GN$ | Music Artist

Five years ago I decided to move to LA to pursue my music career. I was 20 years old, I had no money saved, no family in California, no job lined up for me, and I genuinely had no clue what would happen. In fact, I was so ready to chase my dreams, I paid a deposit to move into a place I found online, I had no clue if it was real or not. Read more>>

Mike Thompson | Art Outsourcing Manager – Zenimax Games

Risk is like a fork in the road. It can lead to a big payoff or a valuable life lesson. Staying in our comfort zone is tempting, but it can also make life feel stagnant. So, what are the risks that have shaped my career? Two stand out: taking on an agent and going solo. Read more>>

Roxane Chabassier | CEO Saya Agency

When it comes to risk-taking, I’m all about diving in early rather than waiting on the sidelines. Trusting in yourself and your own instincts beats letting circumstances or other people call the shots any day. Life’s too short to play it safe all the time, right? Read more>>

Eliza Day | Writer, Speaker, and Intuitive Guide

I think that any decision we make in our lives is entwined with risk. The idea of playing it safe (of playing it small) offers the illusion of certainty and control, but in reality such a decision also risks the possibility that we will never get what we really, truly want because we were not brave enough to ask for it. Read more>>

Bobby Dunn | Entrepreneur

I would say I thrive on risk. All of the best things I have worked on started because I did something everyone else said was a bad idea. For example: one of my projects is a coworking space in San Francisco, called Anchor. It is located right at the main intersection of town. Read more>>

Dr. Susan Swim | Educator, Theorist, Researcher, Author, Clinician

My name is Dr. Susan Swim. I am a risk-taker and I come from a long line of risk-takers. My great paternal grandparents, Irish immigrants, came to America to escape the potato famine, or so it was told. My mother’s great-great great-great- aunt was Mary Todd Lincoln, or so she said. Read more>>

Lisa Song Sutton | Entrepreneur | Venture Capitalist | Former Miss Nevada

The most successful people I know have a high appetite for risk, but that’s definitely coupled with a very optomistic point of view. I ascribe to the idea of mitigated risk. Even when I started my first company (Sin City Cupcakes) I still kept my day job. Read more>>

Natalie Denise Sperl | Actress, Musician, and Activist

No risk, no reward. I live by the motto “Leap, there will be a net!” but if there isn’t a net I know I can fly. Risks always pay off for me, even if I fail. Failure can be a gift, it can steer you in a better direction. I never want to feel “what if..” Read more>>

Sean Yves Lessard | Actor and Writer

Risk is essential. I try my damndest to live my life through curiosity and not fear. I wouldn’t be where I am without risking what was important. Pursuing this career is a risk in and of itself but once you make the decision to dive in you have to commit. I took a giant risk at the onset of covid. Read more>>

Mukhtar Stones | Multimedia interdisciplinary artist, Poly Mathematical, Renaissance Man, Savant

When it comes to risk taking it’s truly a matter of making an uncomfortable decision that’ll challenge you but help you actualize the life you envision for yourself. The first step is by ultimately being yourself. That is one of the biggest risks you’ll ever take and that choice comes with many challenges that’ll make or break you. Read more>>

Devon Green | Writer/Filmmaker

When considering the pursuit of making independent films, the level of risk required- financial, creative, emotional, social- is so high that I feel even thinking about your decisions in terms of risk/reward is debilitating. Read more>> 

Greta Pasqua | Singer-Songwriter, Artist, & Production Assistant

I’m someone who you’d call a Nervous Nelly. I’m very measured and like to play things safe, so on the surface you wouldn’t think I’m a giant risk taker. However, I ended up picking a super risky career path, so it’s kind of funny… Read more>>

Anu Reed | Fashion Designer, Marketing Specialist, Influencer- Fashion, Makeup & Lifestyle

I moved to the U.S at the tender age of 16, not knowing English or anyone here. Looking back from the mature age I’ve now r, it strikes me as one of the riskiest decisions I’ve ever made—second only to marrying a man who lived so very differently (race) from me, which is a story in itself! Read more>>