By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Hayley Tharp | Music Journalist | Host/MC | Content Creator | Founder of Ear To The Underground

Risk is 100% necessary. Growth can’t happen without discomfort. In every season of my life so far, I’ve had to make the jump and hope I land. Anytime I’ve made a risky move, it has led me to something even better than I imagined or taught me a lesson I didn’t know I needed. I think it’s extremely important to trust yourself when taking a risk and do what feels most authentic to you. My career has been a journey full of ups and downs. I’ve made money, I’ve given up money. I’ve made genuine friendships and I’ve probably made some enemies. I’ve been steadfast and driven but have also pivoted. I always try to stay true to myself and my goals though. I will never jump out of a plane or climb the side of a mountain but when it comes to my career, I’ll take the risk. I’ll bet on myself and my goals. If you don’t advocate for yourself, who will? Read more>>

Keram Malicki-Sanchez | Executive Director, Constant Change Media Group. Actor, Experience Developer. Producer.

I think of risk (measured risk) as the necessary action to undertake when dealing with the bleeding edge, or a concept that has few current analogs or comparables in the surrounding culture. I do suggest to folks that I deal with in the spatial media space not to use terms like “the world’s first,” or “the only one to ever…” because let me tell ya, it’s been done before. But things that tend to become wildly successful are mostly familiar and partially strange to the mainstream. So you are taking a risk, but its informed. Read more>>

Jackie Dallas | TV and Film Actress

I’ve always been a risk taker, but I think it’s important to understand what you’re getting yourself into. I like to take what I call ‘calculated risks’. Going from any career to one of an artist is a risky venture. You give up the stability and security that a scheduled job offers, but in exchange you give yourself the chance to pursue your passions and find a level of personal purpose and satisfaction that a true 9 to 5 may never fulfill. Read more>>

Dark Mark | Creative Creator/Clothing Designer

Pretty much goes hand in hand with business one day I woke up and realized it was my turn to jump off the porch with my idea. Another point that goes risk taking is being dedicated and devising a plan and carrying it out and setting up small miles stones the ONO brand. Read more>>

Terry McNaughton | Pop Art Artist

Everything I’ve done has been a risk. Starting a hobby shop in tiny town in rural Manitoba was huge risk. Something I always wanted to do and tried it. Kept up with my creative side painting my Pop Art pieces. Doing something totally different from societal norms is very risky. Read more>>

Eugene Bennett | Filmmaker & Photographer

I think that taking risks are necessary for growth. Thinking back on things early in my career, I can admit that I played it safe in a lot of ways. It wasn’t until I stepped out of my comfort zone and took risks that I started to see progression, change, and growth. Read more>>

David Jofre | Actor

Taking risks in my acting career and personal life has been crucial. At a personal level feels like we start facing decision-making when we are kids and the way we confront those challenges is what shapes our personalities. In my acting career risk-taking allowed me to embrace challenging roles that helped me grow professionally, and take leaps that propelled my career forward. These risks have helped me evolve, adapt to industry changes, and showcase versatility by exploring diverse characters and expanding my range. Each risk outcome, successful or not, has contributed to my development, teaching me valuable lessons along the way. Read more>>

Esmée Lavalette | Director

I think that without taking any risks you might not get far in life and achieving your dreams. When I first moved to LA back in 2018 there was a sign at my hostel that said: fear kills more dreams than failure. When I saw that I knew I had made the right decision, even though I was so scared because I had taken this huge risk. There were many moments before actually moving when I thought about not going, because so much was at stake. Leaving behind all my family and friends and moving to another city in another country where I didn’t know anything or anyone. Now looking back at it, I’m really glad I did it. Taking this risk allowed me to follow my dreams and to really explore who I am as a person. Over the years I’ve grown so much as well. Read more>>

Nicole Sciberras Debono | Visual Artist

Art has always been a part of my life, painting was the medium through which I could communicate most effectively. But taking risks can sometimes be a luxury for the privileged. There’s no point in shying away from the fact that pursuing a creative endevour such as painting involves a high amount of risk (among other things), especially if there are several other obstacles in your way or elements that can determine variables: such as where you were born, how you’ve been brought up, who your parents or friends are. Such is life. The stakes are higher when your luck is lower. But I’d like to think that however lucky you were born and the risks you are willing to take, your fate is in your hands. I don’t think many afford to think any other way. Read more>>

Alan Smyth | Actor, Writer, Director

Risk is a vital component of personal growth. Not knowing, or having certainty on how something will play out is fuel to me. It focuses my attention and makes me feel like I actually have a say in my life. It’s almost certainly, on a deep, DEEP psychological level why I was drawn to acting. It’s all risk, being an actor. You don’t know if you’ll ever work; if you do work, you don’t know how if you’ll “get there”; night-to-night, theres no telling how the show/take will go. We are totally affected by our colleagues, audience, the weather. Theres a constant sense of adapting in-the-moment. I emigrated to America from Ireland to pursue my career further. If I didn’t know what to expect before, I REALLY didn’t have a fucking clue how that move would play out. It’s the very reason it made it irresistible. Read more>>

Leonard Bryan | Writer & Director

I’ve always taken risk. As an artist, everything I write and direct has a little bit of me in it. I call it the risky reward. Nobody ever changed the world by not taking risk, I learned that very on. When I wrote and directed my first short film “Subliminal”, I knew it was a risk. A silent film in this day and age is unheard of. The film examines modern day relationships, I just got out of a relationship and was in a dark place . I financed the film, and put it out independently. I risked my pride and turned pain into art. The film was well received and helped me to move on. The universe is funny like that. At some point caution becomes cowardice. No risk, no reward. Read more>>

Emmanuelle Blanc | Emmanuelle Blanc | Self-Love Guide, Rituals Creator & Transformational Storyteller

In my life, risk-taking isn’t just planning or a strategy, I listen to my intuition and follow my heart, which guides me through the unpredictable journey of life. it’s a part of who I am. Read more>>

Beidi Wang | Producer, Director

“I consider taking risks as a way to explore the world. I grew up in an ordinary working-class family, where my parents’ stable jobs and meticulous personalities helped me avoid many risks, even making many life decisions for me directly. However, I found myself not satisfied with growing up under the protection of my parents. I am filled with curiosities about the world; In high school, I would meet people I befriended with online. I used the money my mom gave me for the Olympics math class to get in a pottery class. I argue a lot with my mom, do things outside of my comfort zone, and oftentimes fail. Read more>>

Emre Korkmaz | Writer, Director, Producer

When I reflect on the past 25 to 30 years of my life, the multitude of risks I took overwhelms me today. I left my well-paying corporate job and traveled to the other side of the Pacific Ocean to study filmmaking in a country whose cinematic tradition I admired. However, I didn’t speak the language, except for a few common phrases, and knew absolutely no one on the entire continent. Read more>>

Ziyao Liu | Writer/Director

I believe in the value of taking risks to challenge yourself, mostly because I find it true that when I stretch myself to the next level of challenge, even if I may not be quite ready for it yet, I’m always surprised by how I somehow level up and achieve things that I thought I couldn’t manage. I guess risk-taking is also quite subjective since others often find my experience risky, but I simply went with the flow most of the time and did what felt right to me at the time. For example, I came to the U.S. alone with two suitcases when I was 18, learned how to fly before I learned how to drive, and chose a career in filmmaking, These random events and decisions led to where I’m at and it’s always entertaining for me to imagine where I would be had I taken a different path at some point. Read more>>

Michelle Mary Schaefer | Actor, Screenwriter, CEO of Annabelle Louise Productions, Director, Producer, ASL Consultant, Intimacy Director/Coordinator

Life is all about taking risks. You’ll never know what you can do if you never take risks. Also, if you don’t ask or send the email, the answer will always be a “no.” If they reject you, it’s their loss; you redirect yourself to another direction to achieve your goals and projects. The key is passion, determination, and perseverance. Read more>>