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.

Xixian Wang: Producer

Life is all about risk-taking to me. I like to take on challenges and that is what makes me grow the fastest. When choosing projects, I often choose the ones that seem to be the most complicated. Filmmaking is not an easy job, Sometimes it can be a problem too. However, when I accomplish the task, I feel that I made the right decisions, because of the experience and lessons I learned from doing it. Read more>>

Jeany Zhao: Ex-Corporate Executive, Now Multi-Business Entrepreneur and Journalist

If you’ve ever asked yourself the question “who am I?” or had a hard time “finding yourself”, taking risks is one of the easiest ways to solve these. Additionally, going through the process of taking risks (and learning from them) will culminate in better decisions and an easier path in your life and career. Risk is discovery…you learn about who you are, and who you’re not. Yes, you will make mistakes…but you will learn even more. Read more>>

Kara Udziela: Animal communicator and Animystic

Several years ago, I faced a life-threatening illness. A 1-percent kind of illness where chances of living a year are 50/50. I had been an animal communicator under-the radar for several years while clinging to another business for which I no longer felt any deep passion. But, I was afraid to take risks. It felt risky to proclaim to the world, “This is who I am. I hear the animals. I can help you.” Read more>>

Kate McSwain: Co-CEO of American Ice Theatre

Risk taking has played a fundamental role in the success of American Ice Theatre (AIT). As a one-of-a-kind contemporary skating company in an industry where the Olympics is the only reason people skate, we had to decide to volunteer our time, work against political alignments in figure skating, and speak out against the traditional culture that figure skating inhabits. Read more>>

ROZEN: R&B Artist & Creative Entrepreneur

I feel like “risk” is necessary in order to be successful, period. In order to succeed you have to be able to step out of your comfort zone and keep doing so. Stepping out of your comfort zone is taking a risk. Get comfortable with being uncomfortable. I believe that is how you grow. Read more>>

Ying Chen Shu: Writer/Director

I believe that everything we do in life comes with risks. You can either embrace that fact and take a chance on yourself or live a life in lukewarm water. I’m not saying one is better than the other. Nevertheless, I would always take the risk. For someone who’s lived their life comfortably for so long, it’s not easy to walk away from it all. I started my career when I moved from Taiwan to L.A. three years ago. Read more>>

Samara Bradley: Musician

Everything in my life slowed down from 2020 to now. I feel as though I was really able to sit down and reflect on how I best function as an artist and ultimately came to the conclusion that the way that I was operating was not working in my best interest. I graduated college in 2019 and I, like many recent grads, was feeling a little lost and unsure of where to begin. Read more>>

2020VZN: Songwriter, Producer & Recording Artist

As an artist, you have to be completely vulnerable. If you’re not, it will show through your art. This vulnerability is a risk in itself. Taking risks is important and necessary. Whether I’m experimenting with producing new genres of music or making new types of content for my social media channels, I am always trying new things to better engage with my audience. As I constantly remind myself, you can’t try the same things and expect different results. Take a risk, try a new approach, it will be worth it I promise you. Read more>>

Gemma Doll-Grossman: Cinematographer

As a cinematographer, I live on a see-saw, abruptly rocking between adventure and stability. At age 22, I bought a one-way ticket to my grandmother’s homeland, Italy, tossing myself into a risky abyss of uncertainty. While making Rome my home over four years, I found my film family: a creative hive of multi-lingual, multi-cultural artists. Read more>>

Steffen “Cookie” Cook: Soap maker, beard grower and collector of dad jokes.

Risk is a word that scares some people. It’s a word that harbors doom and failure. Failure has been ingrained into us as something to avoid, but I’m not sure that that is the correct attitude. Why not see “risk” as an extension of “opportunity” instead? Read more>>

Lucy Valentine: Artist.

To me, taking risks is really important. I couldn’t imagine a career without getting out of my comfort zone to create things that haven’t been seen or heard. With the way that music and art has progressed I feel that taking risks is a natural part of my process and has separated me from any similar artists. The only way I plan on succeeding is continuing to take risks and not care about what society “expects” from me. Read more>>

melanie ornelas: Event Designer + Planner

Risk has played a major role in my career. I graduated college with my degree in public relations and upon graduating, I decided to change my career path and go back to school for interior design. I took a risk in changing my life direction and began reaching out to designer. I was hired by a celebrity designer with no previous design experience. Read more>>

Adela Corral – Bustamante: Ayurvedic Practitioner and Wellness Coach

Risk taking has been a drive for me since I left my country at 20. The challenge and the anticipation of entering a new territory guided by my gut instinct has been an important part of my growth as an adult.
In the case of my current path as an Ayurvedic Practitioner, risk taking has taken on a whole new meaning. The stakes are much higher when you pivot from a successful career in the entertainment business to the health and wellness world at 40 and with two small children. Read more>>

Vanessa Csordas-Jenkins: Film Director & Writer

I think risk probably plays an inherent role in the way I approach my creative work, in the way that I always end up putting a lot of myself into it. This isn’t a groundbreaking revelation, but the more specific a piece of artwork is, the more it will connect with other people, in my opinion. And if you also write your own work, you naturally take inspiration from your own life and relationships, and revealing those things to other people can be scary. It can feel like there’s risk involved in being open about who you are and how you think and feel. Read more>>

Phil Donlon: Actor/Writer/Director

My whole career has been a risk. I had to put my life on hold, so to speak, to pursue my career. It meant putting a 401k on hold, a savings account, marriage, children, buying a house, having a brand new expensive car, having health insurance, all to pursue this idea I had in my head: being and Actor/Writer/Director and getting paid for it. Read more>>

Anthony Colocho: Musician, Producer & Sound Engineer

Risk taking can take you all the way or leave you with nothing, in my life taking risk has opened opportunities I would have never for seen and experiences that have shaped me and given me deeper insight to the man I am and man id like to be. I’ve traveled the world on a risk. My business and art started from a risk. so I encourage taking risk and creating the life you want even if it means to step into the dark the unknown. Life is risky if you like it or not. Take the risk that can bring you happiness, creativity and wealth. Read more>>

Alejandra Gonzalez Castillo: Digital Artist

As they say, “nothing ventured, nothing gained”. For me and my career, taking the risk to leave my home city (Madrid), the professional path that I was on and move to New York (where I knew no one) to pursue my dream, and finally be the digital artist I am today, it has been life changing. In my case, I feel very lucky to have taken those risks and to have found people in the way who have encouraged me to keep pushing, to keep risking, keep improving, so I wouldn’t change a bit of it. Read more>>

Brian Meert: CEO, Author, and Speaker.

It was self-funded. I used the hustle approach to ensure I had 100% ownership. I used small business loans, friends, and family loans and just gave up things I didn’t need in my life (surfboards, bikes, my car, etc) to ensure the business could move forward. Read more>>

Cameron Barrett: Art Director & Production Designer

Taking risks is essential to developing your skills and confidence as a creative. Without it, you would not push yourself to go to the furthest reaches of your potential. When I started seriously pursuing a creative career during college, it felt like a huge risk. What if I fail? What if I’m not good enough? What if I waste a lot of time trying to do something that doesn’t work out? I knew I had good taste, but what if it wasn’t good enough? I feel that this is one of the first and constant “risks” a creative has to push through. The risk that they won’t succeed. Read more>>

Dérly Barajas: Multi Media Artist

The thought of taking risks, in general, is a scary thought. As creatives, we are our hardest critics so it’s common to stay in your lane. I’m not perfect but I take pride in always getting out of my comfort zone and taking risks. I’m a multimedia artist. I took several risks and believed in myself. I’m a full-time artist trying to make my own lane in the music industry. Read more>>

Eric Leatherwood: Digital Marketing Strategist

Risks are absolutely everything, if you aren’t taking risks, you aren’t striving to be better than you where yesterday. In my field of marketing, risk is everything. That’s how you find out precisely what you audience is, what you ideal conversions are, and what funnels work best. Read more>>

Gina Minuche: Event Planner

Taking risks is the only way anyone can start a business, it’s all a risk! From contemplating if you’ll have enough customers interested in what you offer in the beginning, figuring out when you are making enough steady income to quit your day job, to when you can afford to hire more staff to move forward and take the next big step in expanding your business. Read more>>

Sal Framondi: Entrepreneur

I don’t.  That’s the problem.   While some people question whether they should have done this or that, I’m questioning if I should have given a decade to each of my three business ventures that all had high rates of failure.  Fortunately, one did succeed. Read more>>

Elliott Alexander: Artist

Risk is everything, if you don’t take on those lofty ideas how would you ever know what you’re capable of ? When you can surprise yourself with an achievement that you didn’t know was possible- that is one of the best feelings you can have for yourself. Read more>>

David Snyder: Actor, Model, Composer

Risks have played a key role in my development personally, professionally, creatively, and collaboratively. I desire to continually grow and mature as a husband, entertainer, friend, and musician, and I believe that I can only properly grow by embracing and initiating risks. Risks place me outside my comfort zone and force me to think beyond my current capacity and work beyond my conventional strength. Read more>>

Twin Flame Productions: Ty Kranz and Lucine Ajamian; Co-Founders

We founded Twin Flame Productions in February 2020 just before the pandemic. With all of our plans having to be adjusted, we knew there was so much that we can do and take advantage of our resources. We opened up a brick and mortar in the Arts District of Los Angeles in October 2020 and even with COVID-19 public closure, we still found growth and new opportunities. Read more>>

Heather Ford: Makeup Artist

As a creative and a freelancer, taking risks is a huge part of the job in several ways. The biggest risk for me was starting my career as a Makeup Artist. My first career was an elementary school teacher, so I had to completely start over, which of all the risks I’ve taken in my life that was probably the biggest, with the most at stake. Read more>>

Dominic Duarte: Freelance content creator

I believe taking risks is a huge part of being successful. You don’t know if you’ll pass or fail when chasing a dream, yet every success story is full of failure. Failure teaches, success spoils. If you want to be successful, failure will come follow close behind you but facing it head on will set you further apart than your peers. Plus if you fall flat on your face and nothing works out you’ll look back and can say “at least I have it my best shot” Read more>>

John Liang: Screenwriter and Film Director

Being in the entertainment business is by itself a huge risk, and so my attitude, is while it’s clichéd, it’s really true that, the greatest risk is not taking one. Read more>>

Ken Gregory: Actor

Risk taking, my personal definition, is the opportunities presented by life that define us as a person. And there are two types of Risk-takers. Low and High. High risk-takers, like myself, thrive on the ability of being able to step out on faith, unaware, or better yet uninhibited by the numerous pitfalls and extremely high uncertainty that comes with taking risks. Read more>>

F. Tiffany Fleming: Concept Creator & Published Photographer

Everyone takes risks. Some smaller than others but nonetheless it’s still a risk.I truly believe taking risks is what lead me to where I am today as a person and as an artist. I risked certainty for uncertainty and I’m grateful for it. You can choose to live a normal basic life and be content with it or you can take risks that make average moments in life absolutely incredible… Read more>>

Bryania Beauford: Licensed Esthetician & Beauty Brand Owner

I believe that not taking the risk is taking a risk. You cannot and will not be successful in anything that you want to do without it. I’ve always been a risk taker. I have never been afraid to just go for it. I’ve invested my last dime into my business on multiple occasions and didn’t think twice about it. Why? Because I know what is for me will always find it’s way. Read more>>

Laura Salcido: Artist & Business Owner

As the saying goes “Life’s a Risk” Taking risks is necessary to move forward and build. If you don’t take the risk you won’t know if it works or not. I love taking risks in what I do. Putting out new merchandise or adding a twist to my art, will it work out? Maybe, Either way it’s a learning experience for me. I have no fear of failure because I know I’ll keep moving forward and finding ways to make it work for me. Read more>>

Zakiya Murphy: Model/Actress/Makeup Artist

Taking risks is the only thing that brings any sort of flavor or excitement into my life. I believe that taking risks shows the universe (or whatever higher power you believe in) that you’re willing to trust the process of life and venture off into the unknown. Growing up, my life was pre-planned by my parents, community, church, etc. Whether that was an optimistic perspective or a pessimistic one. Technically speaking, I wasn’t supposed to make it this far in life on my own. I wasn’t raised to take risks. Read more>>

Alice Gonzalez-Trejo: Illustrator

I think life is all about risk. My entire career path has been a huge risk. Training to be an artist can be very expensive, frustrating, and even disheartening at times. Art Schools has helped a lot, but it has never been cheap. That itself was a risk, an investment, though I don’t regret going. I think I did at first, doubting myself because I would compare myself to others, couldn’t keep up with the workload, and afraid of failure. Read more>>

Frankie Barrios: Artist

I think taking risks is essential to living a fulfilling life because playing it safe will only get you so far. When I say taking risks, I don’t mean being careless in your choices. I mean listening to yourself and being honest with yourself. Ask yourself- what do I really want out of this life? What are the experiences I would like to have? Your answers maybe very different from what you’ve be told you should want, and that can be scary to go against. But then that’s the risk. Do you take the safe route set out for you or do you make a plan and go for it? Read more>>

Audrea V Heard: Risk taking pays off with Direction & a Plan

Risk taking has produced so many AMAZING results! The risks associated with my current business have paid off in a tremendous way. In 2019, I decided to expand and grow my business. With that decision came a life altering decision to give up my home and relocate so that I could receive financial support from my family. Read more>>

Mike Lindle: Founder + Creative Director

Taking risks can define your success, so I embrace calculated risks. Deciding when to take the leap of faith was the hardest decision for me to make. Planning ahead and focusing on my goals enables me to stay on track and build something I am proud of; I am still growing. Though most wouldn’t know, the risky decisions I’ve made over the last decade have been meticulously planned. Read more>>

Emily Sangder: Artist & Songwriter

Risk taking has never been easy for me, but it’s something that I’ve had to learn to take control of. In order to pursue a career in this industry, I strongly believe that you have to feel comfortable taking risks, or else you won’t get very far. Being an artist is about putting yourself out there constantly, and you have to be able to live with the fact that some people may not like you or enjoy your music, and that is okay. Read more>>

Danielle Bankz: Owner of a Lash & Brow Beauty Lounge

My thoughts towards taking risks has changed many times over the past few years as I have taken more and more risks to grow my business . At first, taking a risk or making a leap from one stage of your business to the next can be terrifying. BUT, I have learned that if you don’t take the risks you are presented with you will never know how far it will push you and how much you can grow from it. Read more>>

Kobe Boateng: Visual Artist

I think of risk as sacrifices you have to make if you really want to make it to the next step in your career. Risk are hella scary and the fear alone can make you think twice about the “absurd” decision you’re about to make. But in reality that risk you make can change your whole life for the better. I took a bunch of risk when I first started my photography journey. Read more>>