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.

Dino Sardella | Filmmaker, Writer, Producer

I believe that taking calculated risks is essential for personal and professional growth. Throughout my life and career, I have embraced opportunities that pushed me out of my comfort zone, enabling me to learn, adapt, and develop new skills. For example, relocating for a job or taking on challenging projects has often led to significant career advancements and personal satisfaction. Read more>> 

Lisa Liu | Jazz Guitarist & Composer

I think following your gut is the most important skill to have, and that often involves risk and going against what other people think and advise.
Every time that I’ve followed my gut, I’ve made the right decision for myself in my career and personal life. Read more>>

Isabel Siragusa | Actor & Filmmaker

I don’t really consider myself a risky person, but I don’t want to live my life with regret. I took a big risk leaving a full-time job and a life in Northern California to pursue a creative life in LA. I think a lot of people thought I was crazy, but I knew that if I didn’t take that leap, I’d regret it the rest of my life. Read more>>

Emily Maverick

To me, most everything I am seeking is on the other side of risk and fear. Whether I’m seeking love or creative freedom or both, I need to feel at least a little like I’m about to fall off of a cliff.  Read more>>

Carri Chen | Filmmaker

A mentor once told me, “If a decision or situation scares you, it means you’re doing something right.” This statement has stuck with me and often sparks courage when I’m faced with a difficult decision. As a first-generation immigrant in a large family of mostly entrepreneurs, I’ve always felt like I’m on a path of resistance for pursuing a creative career.  Read more>>

Dianna Mateos | Lifestyle Content Creator

I believe taking risks is an important part of our lives in anything that we want to do. If you set your mind and time to a specific goal, nothing can stop you from being successful and making your dreams a reality. The role taking risks has played in my life as a content creator has been immense.  Read more>>

Dave Clark | Filmmaker and Futurist

I think about risk as a necessary part of growth and innovation. Taking risks is about stepping out of your comfort zone and venturing into the unknown. In my career, taking risks has been crucial. Whether it was being an early adopter of Generative AI and integrating AI into my filmmaking process or tackling unconventional storylines, these risks have led to some of my most rewarding experiences. Read more>> 

Sara Adler | Spiritual Mentor + Coach

I LOVE taking risks! (maybe a little too much at times) I’ve always been of the mindset, big risk, big reward, and for me, it has absolutely been the case. I’ve never been one to follow the masses, or “fall in line” with what we’ve been taught we’re supposed to be doing, aka, follow a linear path. Read more>>

Nicky Shane | Surreal and Contemporary Watercolorist, Musician Songwriter, Professional Stand-up Comedian, Comedy Writer

Every day, week, month and year, my goals are an un-calculated risk (LOL). The artist’s emotional connection to life is imperative. Fighting for “Time to create” means everything to the busy innovative mind. Taking baby steps within a conscious and subconscious awareness is the definition of being a surreal artist. Read more>>

Mark Larwood | Actor, Writer, Producer, Director, Filmmaker, Musician, Comedian

In the last 5 years since I’ve lived in LA, one of the things I’ve realized is that me taking risks means that it’s going to cost me something and by cost, I mean getting out of my comfort zone. An example of that was for 3 years, from 3rd grade to 5th grade, I had to transition from to school to school and I honestly was afraid of being the new kid and trying to make friends. Read more>> 

Louise Child | Actor, Model, Presenter and Miss World Australia Ambassador

As an actor, model, and presenter, I take risks in my career – a lot. But before I go further, I’ll let everyone in on a little secret: It hasn’t always been easy for me to take risks! Over time I discovered that embracing the unknown, ignoring the fear of failure and facing setbacks was essential for my personal growth. Read more>>

Indigo Cowherd | Photographer & Digital Artist

Risk is an essential ingredient for any artist. If you’re in the visual arts, something as small as putting something out on social media is a risk, because you lose control of the narrative as soon as you share it. Read more>>

Katya Karlova | Former corporate VP turned Curve Model & Content Creator or just Curve Model & Content Creator is great!

This is an important question, I have taken MANY risks in my life and career, and it’s not just because I have a rebellious streak. I’ve always been adventurous, even as a child, but at some point, in my life, I read something about how growth and the lives we are capable of living begin just outside our comfort zone. Read more>>

Karo Martirosyan | Designer

When I first started Karo Studios in 2014, choosing art as my main source of income was a huge risk. I had walked away from a lucrative management career to pursue what I love, but I knew that there was going to be a great deal of risk that came with that decision. Read more>>

Craig Rosevear | Rockstar Real Estate Agent

For me, the transition from a thriving real estate career in Australia to the heart of luxury in California was not just a leap of ambition but a calculated embrace of strategic risk. As a successful agent back home, the allure of Beverly Hills beckoned with promises of unparalleled opulence and high-stakes deals. Read more>>

Michael Abraham | Real Estate Agent & Developer

My career journey has been an adventure full of twists and turns, driven by passion, curiosity, and a healthy appetite for risk-taking. It all began with a strong foundation in architecture, earning my Master’s degree from Pratt Institute. Read more>>