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.

Olivia Lagaly

Taking the leap into entrepreneurship was one of the riskiest, and most rewarding decisions I’ve ever made. I chose a path that looked very different from what most of my friends were doing after college. While many went straight into corporate roles, I decided to bet on myself and build something of my own. It was terrifying at times, especially in the beginning; juggling odd jobs, nannying, and working in retail while trying to figure it all out! My journey was anything but linear, but through the chaos, I realized that entrepreneurship was where I truly thrived! Read More>>

Aurora De Lucia

I’ve been bungee jumping, and diving with bull sharks. I looove taking risks. Some people talk of being “risk averse,” but I think of myself as risk inclined. For instance, the best career move I ever made involved me taking what many would consider a risk, and moving to New York City with no notice. I’d flown in to NY for what was intended to be less than twenty-four hours for an interview to work on “The Nightly Show with Larry Wilmore,” but I ended up not boarding the plane back home. Read More>>

Talula Dempsey

I think risk is a necessary part of any business, whether it’s a bold leap or a small, uncertain step. Playing it safe can lead to stagnation, and I’ve seen both individuals and businesses hold themselves back because they were afraid to take chances. I believe people often thrive when they’re pushed out of their comfort zones. In my personal life, one of the biggest risks I took was leaving college in my junior year to pursue a career in the culinary field. Read More>>

Lisa Henderson

I don’t think of myself as an especially risky person but there have been pivotal moments in my life and career that are definitely categorized as such.

In 1991 I sold everything I owned and moved to Los Angeles to try something new. I came from Canada wanting to get a job in design and literally only had a bag of clothes, my design portfolio and a plane ticket home if it didn’t work out. Read More>> 

Zoya Emami

I reached a point within my career and self journey where not taking risks limited my experience of life and access to opportunities. In the various industries I work in I began to realize you miss every chance you do not take. Being my own support and believing in my abilities and self worth are what help keep me grounded in the whirlwind of it all.  Read More>>

Sergii Leontiev

In art, risk is inevitable and necessary. Some of the most unexpected and beautiful results in my creative work have come from taking artistic risks. In film scoring especially, I often need to step outside my comfort zone, experimenting with new textures, sounds, or emotional tones. Or offering a musical idea that might initially differ from the director’s vision. These moments are always a gamble, but they often lead to exciting discoveries and deeper collaborations. Read More>>

Emma D’Arcy

I’ve been thinking a lot about creative risk recently. I’ve been taking photos for eight years, and you get into a rhythm with your work as time goes on. It’s been very easy to pigeonhole my photography style once I found one. It’s become harder to take creative risks because it feels like it’s higher stakes – what if I lose my clientele? What if it doesn’t work? But when I started off taking portraits in high school, I was trying anything and everything; walking into hotels in San Diego with a camera and a friend in search of the perfect marble flooring, editing with bold colored presets. Read More>>

Miriam Dwyer

I have never taken the conventional path. I grew up in Brainerd, MN, and my main goal in life was just to not live in Brainerd, MN.

When I was 19, I moved to Minneapolis, then shortly after to Nashville, TN where I started acting and hosting, and then finally to Los Angeles, CA, eventually landing a Hollywood agent and hosting a TV show about fashion.
During this time period I met my husband, who was a touring musician, and when we both found ourselves without record deals or TV contracts, that was the point where we stumbled upon a small struggling production company that was doing outdoor events. Read More>>

Qasim Ali

For me, risk is not something to be afraid of — it’s an essential part of growth. Every meaningful step in my life and career came after taking a risk. I come from a simple background with limited resources, but I’ve always had a strong desire to build something of my own. Starting freelancing on Fiverr, learning Shopify, and now planning to launch my own online business — all of these were big risks for me, especially when I had no one to guide me. Read More>>

Amber Aka Princess Datwork Calvin

You have to take risk and not be in fear . In order to achieve your goals you have to get uncomfortable to be comfortable. It’s been risk that I’ve been scared of or intimidated by , regardless of the outcome, I face fear head on . Life is about risk , are u going to take them or fall back ? Me personally I like to fall forward and see what awaits Read More>>

Saransh Sharma

I’ve always viewed risk as a catalyst for growth. It’s never been about recklessness, but rather about believing in a vision deeply enough to step into uncertainty and bet on myself. I don’t jump blindly,I assess potential outcomes, understand what I can afford to lose, and then move forward if the possible growth outweighs the fear of failure. Read More>>