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.

KENJI MIYAZAKI | Hair Stylist / Owner

When trying something new, risks are inevitable. In the first place, it is impossible to avoid every risk as long as you are alive. I consider every risk as an opportunity for growth. Even after “accumulation of experiences” or perfecting the skills, the desire for growth and “acting upon it” is essential for hairstylists. Oftentimes, trying out something new “is followed by failures.” I believe that if you can think of them as a goal or a chance for growth instead of a risk, then you can develop as an individual. Read more>>

Moni Boyce | USA Today Bestselling Author & Filmmaker

I’ve always been the type of person that would rather try or do something and fail than not take a risk. I can remember heading off to USC for college and all of my teachers were trying to talk me into pursuing a different career field other than film. They didn’t want to see me end up a starving artist. Thankfully, my parents were super supportive. The risk of following my heart and going after a career path I was passionate about resulted in a successful sixteen year career. Risk taking is something I’ve continued through my life and career. Read more>>

Fevah Rutland | Singer & Songwriter

Most of my friends and family would consider me to be the adventurous one. Now. I had spent a good portion of my life being afraid of failing or what other people would think and it kept me from doing some things I should/could have done in the past. As I’ve gotten older I’ve allowed myself to fail more, to take chances and risks and to really go after the things that I want. Doing this has gotten me more opportunities and blessings than disappointments. Read more>>

Emily Sweet | Actor

I think taking risks, and more importantly, getting out of your comfort zone is extremely important. I think a lot of people find it very comfortable in their routine, their bubbles, which is fine, but I believe you do a lot of growing when you take risks. For me personally, I have always wanted to act – ever since I was little. There was a point in my life post college where I thought I was kidding myself and I would never be able to make acting a successful career. During that “down time,” being in my safe comfort zone, I was miserable! Every job I had, even if it was a good job, I just wasn’t ever happy. Read more>>

Riccardo Constant | Photographer/Film student

When you grow up in a country like Haiti, you learn how to fend for yourself at a very young age, especially when you come from a low-income family. I had to do with what I had, and it wasn’t much. When the massive earthquake hit in 2010, the family house collapsed, and I lost everything. I could’ve gone to live with some relatives, but I didn’t. I decided to take a chance on myself. The earthquake destroyed the city, and the casualties were innumerable, and here I am with no money, no shelter. The only things I didn’t lose were my dreams, skills, and motivation, and I used that drive to build myself back up. Read more>>

Dahlia Lagos | Artist, Songwriter & Producer

As an artist, songwriter, and producer, risk-taking is imperative. My career wouldn’t be where it is had I not taken the risk to learn new skills, throw myself into new projects, and really challenge myself. It’s easy to judge others from the sidelines, but growth happens in the messy parts of life and the scary moments. Read more>>

Samuel Taylor | Fashion Designer and Entrepreneur

Taking risk in my opinion is one of the greatest achievements anyone can accomplish. I believe taking risk is really devoting yourself to understand and work within god’s glory and purpose. People often go through life trying to understand what their true gifts are for their own individual success – rather than understanding that focusing on your gift is, and will be your social contribution to society through Gods plan. Read more>>

Chris Facey | Photographer

When it comes to taking a risk, I like to make sure the end goal is something that wouldn’t keep me up at night. After leaving the United States Army, I had to decide if I wanted to go to school for dental hygiene or for photography. It was a tough decision. I had to choose between making money and not being happy with the job and being happy making images and keep my fingers crossed for money. I chose to go to school for photography and I’m glad I did. I learned so much about myself and I’ve met some great people in the process. It also feels good being able to tell my daughters they can do whatever feeds their souls. How would I be able to tell my kids to be whatever they want to be or believe in and I never tried? I took a chance on me and its been great. Read more>>

Daniel J. Stimac | Film/Media Composer & Music Producer

I feel like the biggest risk I’ve taken yet has been to start this business in the first place — to choose music for film and media as a career. We’ve all heard that there’s always risk in starting your own business. And before deciding to pursue a career in film scoring, I heard that it’s one of the riskiest and most difficult careers to pursue…especially right now, as the industry is flooded with many young composers who are willing to work for next to nothing (or sometimes nothing) because they are desperate to be the next John Williams or Hans Zimmer. Read more>>

Justin Longerbeam | Audio Engineer / Record Producer

I think that learning when and how to take risks has a huge role in both success and personal happiness. I certainly believe hard work and patience are the things that carry us through the bulk of our growth and lives, but that they are also preparing us for the next milestone of risk. When I think back on my own life and career to this point, it’s the moments that I was able to bet on myself and take a leap of faith in to my future that have yielded the most valuable results. Whether that has simply been moving to a new city, or leaving a job that wasn’t building towards my goals, shaking myself out of comfortable routine and diving headfirst in to uncertainty is what has forced me to make the largest advancements towards becoming who I want to be. Read more>>

Bethany Simpson | Social Media Influencer

I firmly believe that taking risks is essential for longtime success. The first big risk I took was moving out-of-state for college at age 18. Only 15 of the 460 students in my graduating class decided to go to move out of Kentucky. My friends thought I was crazy, not only for moving to Chicago, but for pursuing a career in the arts (musical theater). But moving to the city sparked a series of events I never could’ve seen coming– all of them leading to my current career success. It opened doors and doors of opportunities, connections, and jobs that wouldn’t otherwise be accessible to a teenager living in a small town in Kentucky. It also taught me the importance of creating and growing a network of people in every city who will consistently support my craft. A unique fact about myself is I thrive off of feeling uncomfortable. The more comfortable you get in a place, more boring it becomes. This is why I’m spending 2021 living out of 3 different cities: Chicago, Austin, and LA. This trait makes it easy to consider myself a “risk-taker.” I mean, if you never try, you’ll never know, right? Read more>>

Stefan Costa | Real Estate Agent/Developer

That question takes me back 12 years ago, when I decided to move to United States, I was a 23 years old just Graduated in International Business. The unknown gave me butterflies in my stomach, but I knew deep inside that some major shift was about to happen… A few years here in US, after reading books and documentaries I realized how powerful the mindset and law of attraction are. These two, brought me to a leadership role in the corporation I wanted 8 years ago, not only knowing that so much more was still to come, I kept pushing myself to do better and grow year over year…. Read more>>

Ben Kasulke | Director, Director of Photography, Screenwriter

My relationship to artistic risk taking is rooted in finding a way to feel financially stable in the moment. All of the members of my immediate family worked in the medical field, and my setting out into a creative career in film as young adult seemed like a gigantic risk. I had no one in my life that had any practical advice on how to make ends meet as a freelancer in a field that seemed competitive and financially irresponsible. After college I was idealistic enough to jump into a career in film and have taken it one step at a time for the past two decades. Read more>>

KOBI | Photographer/Filmmaker

I think that taking risks are essential to our growth. How I take risks is by constantly investing in my self financially despite there being a possibility of going without a meal or missing a bill because I believe that my craft can make a difference in the world and in the process make me millions. I am expecting a child in December and I want to be able to teach them that the greatest investment they can make is in themselves and the people they care about! Read more>>

George Holliday | Founder of Made On The Road & Music Producer/Songwriter

I feel like risk is the only way to innovate and stand out from the crowd. The music industry drowns most creatives purely on the amount of competition, so without innovation I fear a lot of artists/creatives miss out on opportunity. But I don’t think that’s unique to the music industry, I feel every business sector is a crowded market and Risk is the only way to cut through. Most people will play the safe cards but, although many will make a good career from doing so, I feel that to be an innovator in your area, risk is the only way to create a new space for yourself. On a personal level, my biggest risk was investing in a library bus (bare with me). Read more>>

Pedro Asfora | Artist, Session Musician and Music Educator

I think risk taking is the make-it or break-it part of life as an artist. If it’s not a big risk, it’s probably not worth doing, but if it’s too big a risk, it’s probably just a bad idea! In my life in general, risk taking has been a somewhat calculated game. The most recent and crazy one is I left the safety of my home in Brazil to meet again with my fiancé in Russia so we can move somewhere else afterwards. Both of us weren’t satisfied with the professional opportunities we had in our native countries, so we decided to go after them together. Read more>>

Jazzman Collins | Super model Jazzmoneè

I do not think one should take RISK but instead one should take a LEAP OF FAITH. To take a risk is to be totally unprepared for the act and to compromise ones morals. To take a leap of faith is following something all the way to the end even when it seems impossible. For example with my experience, at the age of 16 I made up my mind , my home town had nothing left for me . I had gracefully dominated and accomplished everything that could be done in the modeling world in the state of Texas. Read more>>

Duane Jones | Artist and Designer

I fear the thought of living a life unfulfilled more than I fear failure. At the same time, I’m fairly risk averse. I haven’t sunk all of my attention and resources into my business because I want to make sure that I can support my family before I get to that point. Right now there are too many unknowns to make me feel comfortable enough to quit my day job. That said, I’ve structured my business so that I can pivot to earn revenue in multiple ways in the event of a downturn. The idea of putting all of my eggs in one basket is not appealing to me. Read more>>

Sebastian Betancur | Influencer & Actor

I think risk is something you HAVE to be ok with when achieving your goals. Staying safe and complacent won’t get you anywhere in life. You have to be willing to risk everything for your dream. I moved to LA on my 18th birthday and I didn’t even know how I was gonna pay rent the next month. But after taking that risk I found that I was willing to do whatever it takes to make it work. Put your back against the wall, and I can promise you, you will make it work. Read more>>

Eric Williford | Producer/Writer/Director

I make films. So honestly, my entire career is a risk. I’m laughing as I say this, but the truth is, anybody that wants to earn a living by creating art in any capacity is taking a risk. It’s not steady. It’s not easy. Many people in your life won’t understand, but it’s a crazy thing to try and do. You have to be a little insane to pursue it. That’s why I love it. If it was easy, everyone would do it. It takes a special kind of crazy to earn your living with art. You have to embrace the journey, and find fulfilment when and where you can. What role has risk taking played in my career? Risk taking is my career. Just joking. Okay, not really. Read more>>

Dani Blau | Songwriter & Artist

Risk taking: how do you think about risk, what role has taking risks played in your life/career? Risk is the backbone of my career. You risk being turned down, over and over again, even if your work is amazing. You risk investing all of your time and having no significant income for years and years. You risk not fitting in sometimes, or never being truly understood by your traditional friends or family, because you choose the path less traveled. You risk any sort of protective layer between your soul and the outer world, because if you don’t embrace vulnerability, the writing might suffer. As in most careers and life paths, we risk so many things every day. But once we make the decision to take on the risk, it somehow makes the will to achieve much much stronger. Read more>>

Coz Con | Visual Artist

I think risks are imperative to creative growth. I’m definitely a creature of comfort and I constantly have to remind myself that too much comfort can be a killer. The challenge I face now as time goes on and my art gets more attention is figuring out how to both maintain a certain consistency with the path I’m on while also jolting myself here and there to keep the juices flowing. That challenge keeps things new. Read more>>

The Ceasars | Music Producers

It’s as important as talent right now. For us specifically, the simple fact that we decided to move 10.000 miles from our home country, where we were already established was a huge risk. Risk of losing what took years to build there but also of not being able to find a way to succeed here in the US. It was extremely difficult, especially at the beginning but it slowly payed. Read more>>

Benjamin “Ben Jovi” Cunill | Owner LeftCoastLabel Recording Studio

Had I not been willing to take what seemed like an overwhelming risk at the time, I would not be on the path I am today, operating my own business/recording studio, getting to do what I love, while meeting and working with talented and creative people on a regular basis. I had been working in a solid trade for 8 years and decided to take night classes (while working) to learn audio engineering. After graduating from the school, I quit my day job and was interning at studios for free, while driving Uber and delivering pizzas to pay my bills. Read more>>

Amani Roberts | DJ, Professor, Author & Music Producer

I believe taking risks is crucial to having a successful life and career. As the saying goes …” Nothing ventured, nothing gained …” In the past, I have played it safe with no risks and was not able to fully succeed or be happy. It was only when I decided to take risks, say yes, and step outside of my comfort zone that I was able to really “level up” and gain some professional and personal success. I would not be in the position where I am right now if I did not adopt a risk-taking attitude. Read more>>

Ruy Folguera | Music composer, producer, pianist

Starting out as a musician inherently means risk taking. Risk of balancing your talent and your social skills associated with creating and nurturing work relationships. Ever since beginning to study music we are faced with the missconception that it’s not a “real” career, just a hobby or a hope of making it big. Later on the specialization of composer even further outlines the search for the abstract.. and even more so when it’s applied towards film music, where instinct and people skills form a huge part of the craft. So I guess it’s immensely risky and bold as a life choice, but at the same time it’s one usually with no real escape path since it involves a passion to which there’s no clear option. It’s imperative we follow it and therefore no real risk arises since there’s no alternative. Read more>>

Rebekah Laur’en | Singer, Songwriter, Producer and Composer

I see risk taking as getting out of your way, and out of your fears and just going beyond yourself. Risk taking is the necessary crazy you need to get any where in life. We’re scared to do the things that we really want to do because many times going after what we really want is placed outside of our comfort zones and fears. Which is made up of all excuses to not take the risk. Risk taking is the step that every successful man and woman have to take! If we never take the risk to move forward we’ll never exactly move forward. Opportunities don’t come on our time…if we wait for when we believe we’re ready or for things to come when we want them to come, or even for when it makes sense to us and everyone around us it will never happen. Risk taking is that crazy thing called faith, truly believing in yourself and trusting the Devine Universe. Read more>>

Danielle Benavides | Luxury & Coastal Real Estate Agent

Taking risks can be daunting especially when it comes to your livelihood. I have learned over the years that taking calculated risks, and sometimes just going for it, has much better results than over thinking with no action. So far in my life and career I have chosen to take risks, and I could not be more happier with the results. I am all about taking action, it sometimes can be a flaw in certain instances but for the most part you either learn to sink or swim. Read more>>

Kari Caden | Entreprenuer – Belly Bandit & Proof

Well we all know the old adage “no risk, no reward”. My sisters and I have always believed that in order to create our vision there would always be a pretty big risk. I think there’s something so innately scary about risk taking, it keeps you up at night, it makes your heart pound faster, it pushes your limits on creativity and i think all entrepreneurs have that need to feel that excitement. We have lived off of one quote since we started in 2008, it’s on our matching paperweights in the office, it reads: “What would you do if you knew you could not fail”. That, in a nutshell is the only north star you should follow because it takes away a little bit of fear when you think in positive certainties. Read more>>

Jeremy Benbow | Assessing Risk

I feel that choosing to work as a black filmmaker depicting black life is risky in and of itself. I’m not convinced the general public is accustomed to watching black faces on screen on a consistent basis for an extended period of time. Failing to acknowledge this likely affects the opportunities given to up and coming black filmmakers feels counterproductive to me. Times have changed, but reminding myself of this keeps me grounded in the responsibility I see for myself as a storyteller. It all depends on my heart of hearts desire for the work and the long term goal. If said decision, project or job is meant to fulfill and get me closer to the stories I’m driven to tell on a grander scale, then I’ll take that risk. Read more>>

Andrew Perez | Actor, Playwright, and Screenwriter

I’ve come to think of the ability to take risks as one of the most determining factors in whether or not what I’m doing has vitality or not. It’s a lesson that keeps changing and re-presenting itself, reminding me that there *should* always be a challenge and something at stake in the work I do as an actor – and writer, as well… I feel like I’ve just again woken up to the necessity of risk – I think it’s so easy to sleepwalk and do what’s comfortable, but I find that doors open when I play a little more with life and do a Frivolity just for funsies, or take a brave step toward what is vulnerable. Read more>>

Geri Courtney-Austein | Actor, Director, Podcast Host and Voiceover Artist

Truthfully, I’ve come to loathe and love risk! It’s the foundation of every decision I’ve ever made. Embarking on a career in the arts inherently comes with risks, “I don’t knows” and lots and lots of faith. BUT I’ve found that everything wonderful in my life came with extraordinary risks. Deciding almost 9 years ago to move to LA with nothing more than a naïve love of all things film, comedy and storytelling, risking my heart and leaping into love with my current partner, creating my own comedy series and sketch show, pivoting to a raw, vulnerable and boundary pushing podcast. Oh my, the list goes on and on. So many failures, so many successes, so many bruises (literally and figuratively)! As I get older, I realize the greatest reward really does come from the greatest risk and I am incredibly grateful for every moment of this wild ride we call life. Read more>>

Blaine Burgos | Visual Development Artist

I encourage taking educated risks and getting out of your comfort zone when it comes to advancing one’s career. Throughout my journey, I have always saved, studied, and prepared before making an informed decision on the risk I want to pursue so it’s not entirely making blind decisions that lead nowhere. For example, I have turned down a few art director jobs that pay well and would give me a comfortable full-time opportunity but I knew these positions would not make me happy and would deter me away from what I want to achieve. Instead, I took various contract jobs that although were riskier, were the kind of work I knew would get me closer to a career in the entertainment industry. Moving from NY to CA to be a part of this industry was also a risk but I was confident in my skills and was prepared to take on new challenges to be in a field I loved. Read more>>

Ava Cardoso-Smith | Musician/ Artist

Risk has had a huge impact on my music career. When quarantine began, like all of us – I was left alone with my thoughts. I had finished my first year of music school at NYU Clive Davis Institute and still hadn’t put out any music. Even though I was completely terrified to do so, I risked it all and finally put my first single out. Even though I was so nervous as to what people would think about it, I was so happy with the outcome. It really is true about high risk high reward. We have one life to live (unless you believe in reincarnation) and so I think taking risks is extremely important. Read more>>

Sól. | Alternative R&B Singer/ Songwriter

I believe risk-taking is at the foundation of my work. Without risk, there can be no great art. My most recent EP “Moonshots” is centered around the idea that risk-taking is necessary in order to push oneself and one’s work. To me, a moonshot is a project or idea that pushes you to new heights, and to achieve that one must not only let go of fear but also be incredibly willing to fail. This body of work is all about taking the plunge and trusting that in the process you are building something greater. Through the arc of my EP “Moonshots”, I hope to give listeners a glimpse of how I’ve grown into self-confidence through my experiences described in these four songs. I aim to inspire bold, ever-changing, trust in oneself and one’s ideas. Read more>>

Sofia Rusick | Musicians and Artist

Taking risk used to be a no brained for me. I move all the way from Switzerland to came to the US to pursue a care in Music. After attending Berklee College of Music I moved to LA without knowing anyone just because my gut instinct told me that I need to be there. I’n those years I worked for an incredible management company, MDDN, sung as the front woman in my previous band, Seven Day Sleep and organize monthly networking/concert called The Pregame. I always took the risk and never evaluated how it could go wrong because I had a vision. Read more>>

Billye Sands | Newscast Director/Music Producer/Composer

From my experience – and reading about other people who have had successful careers – it’s absolutely imperative to take risks! If you don’t, you just don’t grow! I also believe in taking calculating risks. Please please PLEASE do your research before you just jump into anything. There are a plethora of resources out there that we didn’t have before, plus we’re more connected than ever before. YouTube, audiobooks, online encyclopedias, Reddit and other blogging sites, professors, community leaders, etc. If you’re willing to put the effort in to achieve your dream, there are plenty of people out there willing to help you out! Once you have done all that, there’s just one thing left to do – JUMP and go for it! Read more>>

Emily Ma | Psychotherapist & Mental Health Advocate

Taking risks and putting yourself out there can be really scary! Taking a risk requires vulnerability and humility. Throughout my life, I would not describe myself as a “risk-taker,” in fact I would describe myself as quite the opposite! Years ago, I went to horror nights with a group of friends. I didn’t open my eyes or step into a single maze. I left the park immediately without telling anyone and caught a ride home while everyone else made their way into The Walking Dead maze. I chose my undergraduate major based on what my parents wanted and what I saw classmates from college do. Read more>>

Kelly Tap | CEO of Tap Into Real Estate Inc, Realtor, Investor & Coach

Everyone has varying degrees of risk tolerance. Some of the emotions attached to risk can stem from the way you were raised, a bad business deal, business savvy family members or etc.… However, the more risks you take, the more you’ll be able to understand your tolerance level. Can you endure a big loss or can you stay level headed after a big win? I have taken many risks in my career. For me, following my gut and never settling for less has always propelled me in the right direction. When I transitioned from a full time job with 401K benefits, my gut told me I wasn’t meant to work for someone else and I definitely didn’t need anyone’s permission to go on vacation. Read more>>

Anna Goryacheva | Pianist, Educator, Founder of the Elite Piano Institute

I remember myself living in a small town in Russia, and dreaming about living by the ocean. Sunny California has been always in my mind, even though it was difficult to even imagine where California is located geographically, somwhere at the opposite end of the globe. Being a teenager, I loved watching American TV shows and my heart was stopping and squishing every time the new episode went live. Beautiful life, beautiful people, the ocean, freedom – all of that seemed so exciting, attractive, and absolutely unrealistic. Read more>>

Harvey Seasalt | Artist, Animator, Rapper

Risk taking is a huge part of life in general and especially in the creative pursuit. As an artist, everything feels like a risk. There’s the big Capital R Risk of failing at your dreams when you decide to dedicate your time to making your art instead of following the well-trodden path of a normal career. But there’s also the countless smaller risks that come with being vulnerable, speaking your mind, and opening yourself up to criticism and perhaps ridicule when sharing your art with the public. Read more>>