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.

Stephanie Benedetto Padovani | Business Coach, Storyteller and (Un)Marketer

I don’t often think about “risk” or the cost of doing something. If I want to do something, it seems silly not to try, especially when a simple version can be tested easily before jumping in. I also give myself full permission to stop doing something or change direction if it doesn’t suit. My main stance is, “What have I got to lose?” Read more>>

lori dorfman | actor, musician, poet

being an artist is being a constant risk taker, in every moment of every project. as an actor in a scene, you’re falling off a cliff and holding on for dear life the whole time. as a musician-song writer, you’re a bleeding messy heart and you hope people will like your writing and your sonic tastes. artists create an intimate relationship with risk, it becomes a sort of environment where you hope to thrive and do your best work. risk is a friend, risk is a lover Read more>>

Sapra | Actor, Musician,Filmaker

Hello ! I am writing from my heart so if there are any typos or grammatical mistakes please look out for them and correct as needed ) I am grateful for the opportunity. I have been in Los Angeles for 12 years, I haven’t been back to my home country for last 7 years, I have my health, a car, a rented apartment and about 25 projects to my name. This is what I have earned in the last decade. I have put my youth on the line to peruse my dreams. Read more>>

Fany de la Chica | Filmmaker and Singer

In my case, I think I took the risk when I decided to be a filmmaker and singer. As a filmmaker, I made the risk of making observational documentaries, slow cinema that is not very commercial. And as a singer, to compose songs that mix flamenco with jazz. I come from a working-class family and make a living out of art when your family is not wealthy is very complicated. But I always took the risk of being free and doing my art from this freedom without restrictions. Read more>>

Tanqueray Towns | Performance Consultant

I have always been taught in the environment that I come from (South Central, Los Angeles) that the bigger the risk, the bigger the reward. I have taken that outlook to heart and realize that risk is a major part of building a career, a brand, and in life in general. I took a major risk by jumping out of my comfort zone, moving away from my family to Salt Lake City, Utah to pursue my collegiate Division 1 football dreams. Read more>>

Katherine Diaz | Actor & Post Production Manager

My answer to this question somewhat contradicts itself. I am someone who loves to plan, schedule, and plan some more. When I set a goal for myself, I make a list of all the things I have to do to accomplish it and then proceed to formulate a plan to accomplish said things. Therefore, risk is certainly not something that, at face value, I factor or even allow into the mix. Read more>>

Carla Delaney | Actor & Writer

For me, taking a risk, usually means going outside of my comfort zone. It can mean exposing a vulnerability, taking a leap of faith, or just plain stretching my nervous system and growing my energy field to become larger than what I’m used to being. I’m still working on learning to enjoy risk-taking. Naturally, I’m a fairly calculated person. Read more>>

Anthony Circo | Studio Manager and Music Production Coordinator

Risk is unavoidable and a part of life, I would not be where I am today without taking some calculated, but mostly uncalculated, risks. I feel confidence, belief in your abilities, love of people/relationships and passion can help move through life and career risks successfully. These are skills that develop over time and differently for everyone. Read more>>

Thea Merritt | Owner & Founder at Eco Now

For as long as I can remember I have been a big risk taker. When I was young, I would go on the fastest and tallest amusement park rides, and I moved to California from Minnesota on my own shortly after high school. I believe my fearless attitude has contributed a lot to the success I have had in my life and career. My mentality allows me to act courageously every day and it also attracts risk takers as well, I have been able to surround myself with a team that also takes chances and this has proven to be very helpful for the growth of Eco Now. Read more>>

Ponsée Saa | Entrepreneur & Travel Blogger

I think risks are not only necessary for success, but for personal growth as well. The issue most people have is that they stay in their comfort zone. Comfort zones create and encourage complacency. Taking that risk, doing something that you wouldn’t normally do, something that scares you, can be so rewarding. You can learn something new about yourself in the process or even discover a new passion. It won’t ever be known unless that risk is taken first. Read more>>

Nicole Mitchell | Designer & Founder of Urbane Luggage

Risk is associated with fear, so I’ve training my mind to look at it as a “challenge” that I can overcome instead. “Risk” spearheaded my small business venture to manufacture American-made 100% hemp luggage. Entering the hemp industry in 2016 was challenging since hemp was a Class-1 scheduled drug along with its cousin, Marijuana. Since there is no high demand for hemp fabric, the price per yard is 3-4x higher than other fabrics, and most factories did not have experience working with it. Read more>>

Alisha M. Pennington | Athletic Trainer & Business Owner

I am deeply risk-averse, which may come across as counterintuitive because I am an entrepreneur. But, the way I see it, being self-employed and relying on myself is less risky than having a single employer to rely on for my source of income and advancement of my career. Truth is, my averseness to risk is what has led me to make decisions that some may view as flighty, such as buying and selling 3 homes in 4 years, but actually is what has led to great stability for myself and my family. Being strategic in decision-making is what allows us to hedge against the risk that I do take. Read more>>

E.C. Timmer | Director / Writer / Actor

In hindsight, I realized I happily leap off cliffs… before I realize they’re cliffs. I mean “cliffs” like: taking creative risks. Maybe it’s part of my hardwiring. Or my mom’s incredibly supportive, emotionally buoyant belief in me. Or my dad’s “Why not try?” attitude. But the way I think about creative risk is that I often don’t think about it, I just give it a go. My grandfather used to say: “You’ve already got a ‘no’ if you don’t try, so why be so scared to try? If you try, hey, what the heck: you might get a yes!” (I’ve reworded this. He must’ve said it in a much more polished way.) Read more>>

Keelah Tay | singer/songwriter

It’s important to take risks for growth in life. It can leave me feeling vulnerable when the results don’t go my way. However, it’s important to not remain stuck in the disappointment and acknowledge that I’ve tried my best and to keep moving forward, which is easier said than done. The lessons I’ve learned can elevate my experience by challenging me and encourage me to live an examined life. I really do not want to live a life of regret, so I choose otherwise and take the leaps. Read more>>

Jonathan Rowan | Filmmaker (Director, Writer, Producer)

Risk taking has played a whole role in my film career as it has lead me 3,000 miles away from my hometown of Louisville, Kentucky to Los Angeles, California. Being a dreamer is risky in itself. Nothing happens without a solid plan of action. You have to take leaps of faith to accomplish your goals. Creating your own path is a risk well served. And if you really want to live your dreams bad enough, speak things into existence and make your objectives your reality. Read more>>

Alexandria Valenzuela | Marketing and Sales Coach

I used to be entirely risk-aversive. I hated doing anything that didn’t guarantee some form of security. I didn’t pursue an art degree because I felt it wouldn’t guarantee safety. I stayed in jobs I wasn’t passionate in because it felt comfortable. And then I started my business. Read more>>

Marie C. Zoutomou-Quintanilla | Host, Motivational Speaker and Author

I think in order for us to grow in business and in our personal lives we sometimes have to take risks. I always feel like I’m taking a risk with any new business venture because the initial labor put into the project always seems to conflict with time spent in the family setting. I want my career to grow, but not at the expense of sacrifice of family. Read more>>

Yetunde Oreagba | Lux Balloon Stylist, Event Designer, Project Management Professional & Operations Specialist

I used to consider myself risk averse because I used to be anxious and liked to play it safe to protect myself from failing. Becoming an entrepreneur though pushed me to start taking risks. Taking risks has been the cornerstone of what has propelled me forward as I continue to build my business. I took a risk when I decided to start and run my business full-time and start doing something I had never done exclusively for myself before. Read more>>

Donie Yamamoto | Chief Treat Lady of Vital Pet Life

I think of risk as an inherent part of growth. Every decision I make, whether big or small might involve risk. I believe trust goes hand in hand with risk as well; trusting that whatever the outcome, success or failure, an opportunity to learn and grow presents itself. Risk has brought me to where I am today; creating and growing a brand based on pet wellness and sustainability. Read more>>

Jason Faust | Music Producer and Entrepneur

Risk taking has actually played a huge role in my life as a musician and further into my career as a producer and business owner. I started off my music career playing the trumpet, and due to unforseen dental issues, I had to stop permanently while studying jazz trumpet in school. I had to decide whether I wanted to continue playing music or switch career paths and I had 7 months to do so. Within those 7 months I decided to take a jump and teach myself how to play the piano and within that time period, I was accepted into the jazz piano program and graduated on time. The risk was well worth it in that situation. Read more>>

Trent Walker | Actor/Singer/Writer/Songwriter/Content Creator

I started taking risk when I was a kid. I felt the fear and did it anyway. I think this might have come from watching my parents. One who is very shy and the other who had so many demons that he took his own life. That will make you wake up and wake up fast! I read a book growing up called “Go For It”. It was basically a “you never know until you try” mixed in with positive thinking and the law of attraction. I’ve always liked people and loved stories. As a kid I’d go to the older people’s houses and listen to their stories. I loved hearing all the tails and most of the time they had candy and I like candy too. Read more>>

Grey Coutts | Abstract Artist, Designer & Director

Risk-taking has shaped and changed my entire life and career. Fear is very persistent in all of our lives and once we learn how to push through it and not worry about the outcome of our risk-taking, we discover our real talents and who we really are beyond the limitations of our minds.  The biggest struggle I used to have when making art was actually starting the process.  Read more>>

Briana Danyele | Fashion Designer & Fine Artist

No risk no reward. Simple as that. Sometimes it doesn’t work out but sometimes it does. As Momma Ru Paul says, “And if I fly, or if I fall Least I can say, I gave it all And if I fly, or if I fall I’m on my way” Read more>>

Dennis Nelson | Entrepreneur & Business Owner

Risk is an integral part of everyone’s lives. Whether directly or indirectly, consciously or otherwise, risk and risk appetite is one of the leading determinants of people’s outcomes, and how they assess moments and choices ahead of them. Read more>>

Joshua Han | Actor, Writer, Director, Coach… with Clown on the side

They say: Without risk, there is no reward… I can dig that, but failure should be sought out in order to find out who you are and your optimum self. If you never take risks, you will never truly know yourself or what you are capable of. But for the most part, I’m kind of a leap first then tuck and roll type of guy. I get my fair share of bumps and bruises:) Read more>>

Jacki Ueng | Title Rep & Travel Blogger

I believe that taking risks is the key to breakthroughs and living outside a structured, pre-planned, mediocre lifestyle. I have taken several risks since I became a free adult (my parents were extremely strict growing up and it wasn’t until I left home was I able to spread my wings): Read more>>

Karissa Montaner | Actress, writer, photographer

Risk has been the impetus in my life. I was sheltered from an early age and then when life hit me in the face I knew I had to make decisions that made impact in order to create change. I’m a person who likes to move forward, so I’ve heard that doing the same thing over and over with different results is the definition of insanity, and I think it’s true. That expression is how I keep myself in check. We as humans have to risk sometimes to find another way. Read more>>

Jonathan Tumblin | Actor, Comedian, Musician + Writer

I’ve always been a risk taker, my parents and peers would attest to that. In high school, I was an athlete in arts programs which was considered a huge “no no” where I’m from. After college I joined the Air Force, instead of going on the job hunt in corporate America, in order to have the benefits and stability I would need to pursue the life of an artist. So I’d say taking risk has definitely set me up for the freedom to play and pursue a career in the arts. Read more>>

Sharice Chaney | Entrepreneur & Community Event Planner

There is a quote that I love and I live by, and it says “The only thing permanent in this life is that everything is temporary.” I believe I appreciate this quote so much because it reminds us that our time here is limited, and our circumstances can change at any moment! Which tells me it is THAT much more important to live in the present and outside of those comfort boxes we create for ourselves. Read more>>

Liel Kolet | Singer/Songwriter and Performer

Throughout my career I had to take many risks in order to fulfill my dreams and achieve different goals. As a young girl when I was only 13 years old I decided to give up a normal childhood in order to sing and perform around the world. Even during performances I had to take risks sometimes, and one of my most memorable ones was at a huge Peace concert with many world leaders, when while on stage right before I was about to start singing I decided to ask former US President Bill Clinton to join me on stage to sing ‘Imagine’ together. Read more>>

Vasundhara Gupta | Music Composer, Producer & Vocalist

I believe there is a certain amount of risk in almost everything we do, right? Be it the beginning of a new relationship or the beginning of a new venture. I think about risk as part and parcel of most of my life moves. And I think that has made me more able to ‘go with the flow’ and treat what might be major life decisions in a calm manner, keepings emotions at bay. Read more>>

Marijane Chuang | Owner & Pet Nutrition Specialist

The biggest risk is not taking any risk. — Mark Zuckerberg. In order to grow, we must take risks in our lives. Taking risks will take me outside of my comfort zone, pushing me to do what I am afraid of doing. It is as an opportunity to make something happen, and embracing the journey it takes me on. I’ve learned to take risks as a young girl to the present. At 18, I left Hawaii to go to college on the mainland, knowing that I would need to make new friends in a new state. Read more>>

Jaseida Mojica | Actress

I’ve always followed my heart first, then my gut and finally my mind. It’s important to take big risks in life in exchange for big rewards. I originally graduated premed with a degree in Biochemistry and a scholarship in the Performing Arts. I knew my dream was to open up a performing arts studio called WESPAC and later become an actress. This would mean not going on to medical school, but the performing arts were my dream from the age of 10 years old. Read more>>

Lucy Wright | Hairstylist/Salon Owner

For me Risk is more like adventure. I always think of all the things and decisions that may have made me nervous or unsure and some have been successful and some have just been experiences but I do not regret any of it. I am currently Building my own salon in westlake village with my long time friend Tasia. We are so excited for the future especially after such a trying year for us all. The Mix of nerves and excitement is real lol but i know it is my next adventure. Read more>>

Optimus Grind | Writer, sound designer & engineer

I think life is all about taking risks. Some work out, and some do not. I took the risk of coming to Los Angeles 20 years ago and it’s all turned out nicely. If I hadn’t taken the risk of coming to the west coast a lot of my dreams couldn’t have been realized. I had a lot of failures along the way, but they have all helped to guide me to new places and help me grow. It’s been a fun journey, and I’ll continue to take risks. Get’s pretty boring not going out on a limb. Read more>>

lynette rios padilla | L (Crunch Pod Label Recording Artist)

Risk taking is very important when it comes to the process of success. You need to take risks. There is no success without risk taking and thats just how I see it. However, you MUST take calculated risks, think of the different outcomes, and hypothesize results as best as you can. I’ve taken risks since I was a child, from leaving my fathers house at a young age, to signing up for Art College, to starting these L and famblood projects, to forwarding my executive decisions at the daily office. Read more>>

Alba Morera | Filmmaker & Photographer

Risk-taking is stepping out of my comfort zone to explore new territories and experience new perspectives, allowing for growth. It’s about the human experience and the openings that come when I embrace the unknown. As an artist, I create from that space. In life, I grow when I take risks. Read more>>

Dom Bournés | Creative Producer of Acute Animation

My entire life has been about taking the creative risks and making bold decisions that go against what everyone else is doing. In order to stand out, I believe you have be loud and bring that energy. Risks are only risks when you don’t study and do your homework prior to making a decision so I love researching an idea before the execution phase. Risk essentially is challenging the norm to do something new. Read more>>

Nadav Peled | Musician, Guitarist, Composer

I think you can’t really be an artist without taking some risks. You risk not having financial stability, an ordinary lifestyle , you risk people not understanding your most personal creations. For me, maybe the first thing was moving to NY from Israel. I grew up in a pretty small town but always had the inclination to move to New York. That move at a young age was definitely not easy but I’m so happy I took that chance. I’ve found more inspiration that I could’ve imagined, opportunities and made connections with some of my dearest friends/ collaborators. Read more>>

Pierre Tsigaridis | Film director/writer/producer

As a director/filmmaker I feel like I have to constantly take risks. Filmmaking like many creative and artistic fields has always an unknown outcome. As for directing, taking risks means exposing my vision, my project and my sensitivity to the world and to people’s criticisms. It can be very intimidating and I have to be willing to take these risks from the very start. Read more>>

Allen Kass | Musician, Artist & Producer

I think risk is one of the biggest aspects you encounter when it comes to this journey with music. I’ve been making music for over half of my life, and what I learned is nothing is ever guaranteed. I released a mixtape back in 2012 called Free Falling. Read more>>

Pedro Mancillas | Musician, Producer, Freelance Audio Engineer, FOH, Studio and Venue owner

I personally believe that in life we all need to take risks or chances. My philosophy is you have to fail in order to win. Its not common you hear how many times an entrepreneur has failed. We only hear what made them successful. Success makes us feel good and accomplished. Read more>>