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.

Sam Frontera | Actor & Podcast Host

Taking risks is a big part of being a creative person. Unfortunately, I was not born with a fully-formed risk gene which means it takes a lot for me to jump all-in on a project. I’ve found that my gut is pretty good at telling me which risks to take by making me OBSESSED with an idea. If I am lukewarm about a topic or potential project I tend to hold off but if I can’t get the concept out of my head that is the only sign I need to take the plunge head-first. This is true for professional decisions, like starting my podcast in 2019, and personal decisions like moving to LA without a real backup plan. I’ve learned to trust my gut explicitly and haven’t regretted a single choice so far. Read more>>

Kim Genevieve | Award Winning Photographer

For me, taking risks means following that gut feeling that lives within. It’s the reason I’m here today and why I continue to move forward towards a vision that only I can see for myself. I’ve always been quite curious to see what I’m truly capable of doing with this one life. Risks are simply a part of that curiosity. It was a risk when I left my job and hometown in Canada to search for something new and different in Los Angeles. It was a risk 8 years ago when I charged all my camera equipment to my credit card when I was just getting started with photography, and it was a risk last summer when I decided to launch my online gallery & store. Everything feels like a risk at first when you’re trying to move from where you’re standing right now to where you want to be tomorrow. Taking a risk is betting on yourself, and maybe that’s what I’ve been doing all along because the truth is, who else is going to believe you if you don’t at first believe in yourself. Read more>>

DeAnna Elise | Actor, Model, Dancer & Singer

When it comes to risk taking, growing up in the south sometimes it feels like a very hard task to take risks. Growing up in Georgia as and African American woman, a lot of times taking risks and doing thing out of the ordinary was not approved by the community and it was almost as if the people around me were afraid of me taking the risks I took for multiple reasons. The biggest risk I have taken so far is deciding for the rest of my life I want to entertain people, and that I would be moving from Georgia to Los Angeles to go to school and pursue the performing arts. I got so many questions about why I want to perform, if I really think I have what it takes to be an entertainer, do I think I can make a career out of this, and the craziest comment I believe I got was the, ” its a one in a million chance you’ll make it in the industry, and I don’t know if you’re that one.” Hearing things like that over and over again really did put a damper in my confidence and really made me question if this was the right thing for me to do. Read more>>

Emilynn Rose | Photographer & Entrepreneur

Life will scare you but when you choose to overcome it, you realize it was never that hard. If I had never taken the risk of becoming a photographer, I would always be left wondering, “What if I did?” I started my journey with not having anything. I packed up my stuff in my almost-broken-down car, had $2000 to my name, and started my new life in Los Angeles. There was a time where I had no direction; no one in my life was pursuing the same career so I had to figure it all out on my own. This was the choice I had to make, and I’m so glad that I did. Now, years later, I’m living my best life, financially secure, and able to share it with my family and those around me. Read more>>

Richard Harris | Songwriter, Producer and Mentor

My parents were both risk takers in very different ways. My father took chances in music which paid off for him at various points in his life. He was never afraid to learn and jump in at several different junctures of his life. My mother just did everything her way. Wore the loudest clothes, was the brightest star in any room and moved houses a bunch of times always searching for that right space. She never showed fear just the desire and hoped it would work out. That set the tone for me I suppose and despite some moments of trepidation I have found that my greatest risks taken have led me to the greatest rewards. When I was in my twenties I was in a full time job. A good one. Making good money but I wasn’t happy. Music was my passion and the need to give it the time and effort was running out. Not because of my age but because the trappings of a successful career was getting too hard to let go of. So I jumped ship not knowing how things would turn out, armed with the only plan of my gut feeling that this was the right and only move. I downsized a lot! There were moments of sheer terror and frankly financial hardships. Read more>>

Chelsea Thomas | Practice Manager & Patient Care Coordinator

I have always been an opportunity taker, or what others may call a risk taker. By paying attention to the things you are naturally drawn to and having the courage to follow them, you are naturally a risk taker. Taking risks have been vital to my life and career. Right out of college at 22 years old I took a risk moving out of state for an internship. When it didn’t pan out like I thought it would I used it as an opportunity to take another risk. I thought about how I always wanted to live in California and there were probably more opportunities there anyway. I used my current situation as motivation and a few months later I was on my way to move across the country to Los Angeles. Fast forward to 2018 and I had been working as a successful Event Production Manager in Los Angeles for several years now for a few different luxury event companies and venues. I had just started with a new company when it hits me. I am not happy. Like, not happy at all. I used to love the excitement of my job, what happened? The odd and excessive hours, the missing every holiday with my friends and family, the constant high stress environment. Read more>>

Samantha & Amy Bloom & Russell | Business Owners, Artists & Sewists

Because we were practically strangers when we decided to start StitchSpace LA, risk has been a part of our business since day one. Samantha realized that she and Amy were two sides of the same coin. All she knew about Amy was that she was a great teacher and all Amy knew about Samantha was that she was a go-getter. Being a former small business owner, for Amy it wasn’t about the risk of starting another new business, it was about whether she really wanted to take on that amount of responsibility again. Samantha’s personality is to self reflect and then eagerly get moving to make things happen. Besides moving to Los Angeles, opening StitchSpace was really the first big risk Samantha ever had to take. So when Amy said, “Well it either works or it doesn’t” that’s the first time the fear of risk really sunk in. However, you either do something or you don’t and we are definitely doers. So after a lot of planning, we made the calculated risk to create the place we wanted to work at. More than anything our studio is about inspiring creativity through making. We can’t help but become invested in our students’ success. Read more>>

A’magine | Sexual Empowerment Educator & Author

I have always been a risk-taker, it’s in my DNA. That has made COVID challenging as I see the difference in risk-taking and assessment patterns among my friends! As an entrepreneur, risk-taking is part of the deal. Things change on a day-to-day basis. One day this trend works, the next week, it’s something new. There is a constant learning curve to everything we do. I have to be able to roll with that, and also decide what bold moves I will make in service of my vision and the mission of my business. If I were more conservative around risk-taking, I never would have published my first book before I turned 30, seen it be a best-seller, gotten myself on a TEDx stage, or put everything I had on the line in service of what I am here to do. Risk-taking has served me well overall, and at times, it’s exhausting. Self-care goes along with it! I have learned to manage my energy on multiple levels and have a brighter eye for the burnout that can hide under the adrenaline rush. Read more>>

Tammy D’Onofrio | CEO/Founder FitChick Lifestyle Brands

I used to be a very harsh critic of myself. It’s a daily practice to not fall into the rabbit hole of feeling like an imposter. Taking risks is the single most impactful thing I have done to raise my self confidence, parent my children and run a successful business. Society is driven to put people in boxes. It makes others feel safe to have you figured out. There are about 100 reasons why I shouldn’t be successful. Starting a business with no money as a single mother, a small town girl from Indiana. Who am I to think I could find success in Los Angeles? Well in my experience, taking risks, makes you feel more invincible. Doing something that scares you makes you courageous. So I created an amazing product. Taking something that has been bastardized by the processed food industry and making it healthy. Then I threw out the traditional – to market – strategy and created my own distribution channel. Did a lot of people tell me no? Hell yes! Did a lot of people tell me it can’t be done? You bet! But, I’m free of societal constraints! I believe I can be successful on my own terms. Read more>>

Alex Casillas | Artist & Photographer

Over time I’ve learned that comfort leads to complacency. Once I settle a little too much into a certain style or idea, my work becomes bland and I lose inspiration. Risk is such an essential part of the creative process because it’s what pushes you to explore the unknown territory where those next-level ideas are hiding. There’s an infinite amount of new works and ideas that exist purely in hypothetical form, just waiting to be created, and risk allows us to tap into them. In my own career, stepping outside of what I’m comfortable with has been the key to any amount of success I’ve seen. Whether that’s reaching out and pitching to specific clients I want to work with, trying out brand new ideas in the middle of a shoot, or stepping into new mediums all-together, the uncertainty that comes with risk taking is what keeps me going. It doesn’t always work, but that’s the best part. Read more>>

Dr. Wang Newton | Drag King Extraordinaire & Breathwork Facilitator

I must confess… I mostly grew up in small towns across America and considered myself a low key quiet type.  So how did I end up running around the world dressed in a bright red suit + drawn on mustache + pompadour, and ahem… *dildo* under tight pants?  As it turns out, I must have grown a pair of invisible balls to go with the look!  Being a drag king for the past 16 years has been one big risk (at a time when social media didn’t exist and drag queens were not even popularized by television). The moment I took drag off the safe space of queer stages and out onto international streets, ‘Dr. Wang’ essentially became improv performance art — anything goes, baby! If I followed the dots however, big risks have provided big returns for me: to fight bullying and prejudice, during high school I asked my BIPOC college friends to help me teach multicultural awareness to elementary kids; I moved to NYC right after college without money nor connections; to heal anxiety from witnessing 9/11, I refused to take prescription drugs and stayed in Berlin for a spell. Read more>>

Stephanie Diani | Celebrity, Portrait and Editorial Photographer

I had the advantage of being raised by two fiscally conservative and dedicated parents. I say advantage because they ensured that my brother and I had food, clothing and education, and I remain incredibly grateful for those gifts. We had to work for what we wanted, but my folks did what they had to to provide for us. They were both children of the Great Depression. One goes to school. One gets a job. One stays at that job until retirement. So my decision to forgo grad school to become a self-taught photographer was met with some … dismay. I think that was the first time in my adult life that I felt I stood at the edge of the risk cliff. That’s how I think of it, when I make decisions that fly in the face of my upbringing. I’m standing on the edge of a cliff and preparing to throw myself off. Take the first step and a bridge will appear — did someone say that? I also think of Harrison Ford in the Last Crusade stepping out onto the rock bridge, you know, in that scene towards the end. Yes, I’m Harrison Ford in this scenario. First risk: decide to become a photographer. Read more>>

Dr. Amanda Cohen | Doctor of Chinese Medicine, Functional Medicine and Sacred Medicine

I love, love, love what I do and what I have created. It’s taken me many years to arrive at a place where I can finally exhale and enjoy all that I’ve created in becoming a doctor, building a wellness center and health clinic of my dreams, and birthing a new modality where I can provide healing to anyone in the world. I am a Doctor of Chinese medicine and practice functional medicine. In my medical practice, I interweave science and magic by combining eastern, western and sacred medicine, getting to the root of health imbalances and providing lasting results to those I serve. HOW BEING THE FOOL HAS BEEN THE SMARTEST MOVE I COULD MAKE Though I’m deeply rooted in science and research, I love magic and all things mystical. The past 2 years, I’ve been learning the Tarot from my dear friend Madame Pamita and her book Madame Pamita’s Magical Tarot. I’ve learned to embrace even the “scary” cards (you know…like “Death,” “the Tower” and “the Devil”) by seeing that all of the darkness is just there to be acknowledged and released before the dawning of a new beginning emerges. Read more>>

Camille Corbett | TV Writer & Actress

I haven’t taken a lot of risks in my career. Most of the moves that I have made have been very tactical. I feel like you sort of have to be very strategic to approach any lofty goal. But I will say sometimes I push my limits. Like I’ve been known to email a Kickstarter or a link to a new project I’ve been working on to every person in the industry that I know. But I feel like sometimes that boldness is needed to get anywhere and show the right people that you are building towards your career as an artist. Honestly, it’s a great way to be pleasantly surprised at how many people believe in you. Most of the Kickstarter donations for my Crystal & Chelsea pilot came from people that I emailed personally. Read more>>

Dani Rhoades + Whitney Eves | Perinatal Nutritionists

Risk taking is the only way Happy Healthy Littles exists! Dani had been working in a pediatric office as the in house nutritionist for 5 years (while running her own nutrition consulting practice on the side) before realizing that the ‘need’ for her care was more than she was able to give. She took the crazy step of buying a condo to have a home office for the first time to work out of and leaving her stable job for the totally unknown. She had no idea what the next steps were – she just knew there were women all over the country that were pulling for her attention and her time working locally had to end in order to meet the larger scale needs of women + their babies. She had only just begun talking about a potential partnership with her longtime friend Whitney Eves, who then was just graduating from nutrition school – a risk she took altogether going back to school in her 30’s while pregnant with her first knowing she was also only just starting to grow her family. Dani is so thankful that she did because their partnership produced the most beautiful blend of Dani’s professional expertise + Whitney’s personal experience. Read more>>

Shaelin Jornigan | Painter

Painting at all is to risk failure, and I am not particularly comfortable with failing. I am equally uncomfortable making a painting I already know how to make. So that leaves me in a miserable bind any time I enter the studio. Still, the successful moments in my paintings are usually a result of some unexpected impulse, accident, or precarious decision that had the potential to ruin the painting, but didn’t. This is the uncomfortable reality of risk-taking – there is no reward without the possibility of pain. The first time I came face to face with this concept was during an exhibition in 2016 when my largest painting was swept off of the back of a friend’s truck by a gust of wind during transport. We watched in shock and horror as my precious canvas flew into the intersection and was run over by a massive box truck. Something clicked inside me – the fear of ruining my painting was making me stagnate. It was a good painting, but the tire mark on the back became the most interesting thing about it. After that, the idea of scribbling on, covering up, or cutting into a painting has become a necessary risk in my practice, despite the perfectionist fear that grips me in the process. Read more>>

Tania Bunic | Blogger, Fashion Designer, Entrepreneur

Risk pretty much summed up my 2020. Firstly at the beginning of 2020 before the outbreak I have decided to travel to Bali and stay a few months in order to research and develop a sustainable resort wear brand. So when the outbreak hit and my flights back home got cancelled I decided to take the risk and stay on the island fully embracing the unknown. I threw myself into the brand development process which was a big risk in itself as no one could’ve predicted that the whole world would be so affected by the outbreak. Especially me as my brand is resort wear and someone told me that this is number 2 on the list of least useful things of 2020. But I didn’t allow this to stir me away from my goals and I trusted that what I’m creating will make women feel good so once 2020 is over everything will be better. So I worked away and created 4 collections, built a beautiful concept based on female empowerment and slow fashion, worked with inspiring women that posed and represented my brand as models and I had faith this mess will be over soon. Even though my revenue has been massively impacted by the outbreak and my decision to self-fund and launch this project in the mids of the outbreak, I firmly believe that the risk I took paid off. Read more>>

Dom Lay | Artist and Writer

I believe that risk taking is a necessary part in reaching or achieving our goals. Often times we like to live in comfort and avoid pushing our boundaries that could possibly lead to something greater in our lives. We tend to sit around and keep thinking to ourselves, what if, or no, I can’t do that, or what will people think of me? It is this innate fear that will not allow us to discover our full potential in what we do and create. There were many risks I had to take when starting my career especially. Years ago I always had anxieties in my head that people would judge what I would do. I began the journey of becoming a concept artist to work in the entertainment industry. But as I was studying over the years, I felt that my art wasn’t going anywhere. I was stagnating as an artist and I grew frustrated. I was merely copying what my peers were creating and what types of subject matter people in the industry were doing because I thought it would ultimately land me a job. Soon enough I was burnt out of art, and lost my passion to create for quite awhile. Read more>>

Elizabeth Russo | Songwriter

Risk taking to me is everything. When I moved from the Bay Area to Los Angeles to pursue acting, that was a risk. When I left a steady acting and modeling career to become a full-time songwriter, that was a risk. If it’s something that makes you happy and you can’t imagine not doing it, then to me, there is no risk. I’ve always made it work. A quote I live by “Security is mostly a superstition. Life is either a daring adventure or nothing.” — Helen Keller. Read more>>

Danielle Lescure | Storyteller / Case Study Specialist & Content Creator

I’ve taken really big leaps in life I never thought of them as “risks” per se. And yet, they really were since each of those choices was truly a dive into the deep end of something I had absolutely no experience with, and I had to figure out how to sink or swim, or simply get out of the water altogether if it wasn’t for me. I prefer the term another woman coined when I told her about some of the all or nothing moves I’ve made in life. She called it “radical action,” and that, for me, is what risk is. Radical action is a mix of wanting to see what other adventures life has to offer and wanting to find out what else you’re capable of. I take radical action when I know I’ve reached the end of one road and need to begin on another. I take radical action when I realize something needs to be done, and I’m passionate enough about it to jump in and do the work. And I take radical action when I can tell I’m stuck and holding myself back. Read more>>

Lia Battaglia | Vegan/GF Home Baker

I have always been timid and taking risks has always been a challenge. However, as I got older, I became more ambitious. I’m grateful for this because it has allowed me to grow as a person. Risks are a necessary part of life; without them, we would probably live a mundane life. If you have a goal, you must take that first step-take the risk! It may be challenging, you may be frightened, or you may not succeed the first time; and that is ok. I dreaded failure and often doubted my own potential. It’s something I still struggle with at times. Even though I’m not as talented compared to other bakers, I constantly remind myself why I started and how far I’ve come since then. Baking brings me joy, and I want to share that passion with others. Read more>>

Mike & Anne Howard | Travel Authors, Photographers & Influencers @HoneyTrek

We had a dream to take a honeymoon around the world. With a new marriage to celebrate and youth/health on our side it seemed like the perfect time to dive into our bucket list. The only problem was, we’d have to quit good jobs, rent-out a our home, sell most of our stuff, leave our family and friends, and book a one-way ticket into the unknown. As dreamy as this honeymoon sounded and as convinced as I was that it was great idea, pulling the plug on a perfectly good and stable life was terrifying and to many people, foolish. When in doubt (or mini panic attack) there is a quote by Randi Komisar that comforted us and still rings true: “And then there is the most dangerous risk of all — the risk of spending your life not doing what you want on the bet you can buy yourself the freedom to do it later.” Staying home and waiting until we were 65 years old AND assuming we’d have our health, finances, and life in order to have take on these adventures seemed was a far greater risk and not having these life-changing experiences and not immersing ourselves in hundreds of other cultures would have robbed us of our greatest education. If you want something in your life, don’t let fear or pettiness talk you out of it. Read more>>

Puppett | Filmmaker & Actor

My casting choices and the stories I want to tell are often considered risky, particularly because I want to put underrepresented people on screen. Early on, when I was developing my short film Wedlocked, I knew the easier way to get funding and interest in the festival world would be to tell a story about gay men. Or if I went with women, to show feminine lesbians, because that’s what Hollywood does. But I wanted to show more sides of our community. It felt important to me to take this risk: showing soft femme, masculine-of-center, butch, androgynous, trans, gay, lesbian, bisexual, queer – we’re a rainbow and I wanted to showcase our diversity. I had to trust that people would want to see themselves and their friends on screen, and not just the same types of representation we’ve been getting for years. I continue to make “risky” choices when casting my projects. I often think outside the box and cast trans people to play roles that may or may not be specifically transgender. Casting trans actors in roles that don’t specify a trans identity was totally unheard of when I started doing it, but now it’s starting to happen more. Read more>>

Kaitlyn Croteau | Model/Dancer/Actress and Former Clinical Social Worker

I’m always anxious to take a leap of faith in my life. I was actually just thinking about this today. I never want to take the steps necessary for growth, because it is unknown and I am often paralyzed by fear. However, I’ve always had this thing within me where whenever a situation no longer serves me my body and mind go into autopilot and take over. I start to move forward whether I like it or not. As a spiritual person I might say that this is my soul or a higher power guiding me. Call it intuition or whatever you want. All I know is whenever I need to take a big risk I just do it, but all the while I’m terrified and feel unprepared and unready or undeserving. There’s a great parable called The Parable of The Trapeze. I just read this to a friend recently because I am currently going through much risk taking and growth and change. I’ve read this passage dozens of times. When I grabbed the book to read it to her I opened to the exact page. The abridged version of the parable is this: Life is a like a trapeze. Here we are swinging along on one bar, and then all of a sudden the next bar presents itself. Read more>>

GoopMassta | Urban Artist

I choose to concentrate on what makes me feel uncomfortable about a situation instead. The feeling of discomfort makes me realize whatever the situation may be, it’s probably something I haven’t considered pursuing yet and because of that is something I should explore. By jumping in or “taking a risk,” I’m 100% of the time gaining knowledge no matter the outcome – succeed or fail – either way I learn something. I believe by putting yourself in uncomfortable situations you grow and gain so much as an artist. You push yourself past these boundaries that you may have unconsciously set for yourself. Every experience can be a positive one as long as you are willing to see that. How are you going to know what you are capable of if you don’t try? I believe taking risks has tremendously enhanced my career, because there is nothing I won’t try at least once. Risk taking has given me the confidence to say yes more than no, open the door instead of close it, and stretch to reach new heights daily. Read more>>

Jonathan Clough | Co-Owner of ChocoLab, LLC

I believe that taking risks is one of the most important aspects in ensuring career success! Some of the biggest successes came from taking risk. I always try to think “outside the box” and do things that maybe are not the normal for my particular industry. I think one of the big mistakes that gets made in business is that people let themselves get confined in boxes because that is what is expected or what has been done before. That eventually leads to stagnation. Do things that break the norm. Yes, you will have failures, but you will learn from those failures and they will lead you to success. Read more>>

Nancy Rumagit | Actor & Writer

One of my teachers told me, “If a part scares you, then you have to do it.” He was talking about acting, but I’ve started to carry that with me in my life as well. Life just becomes a little bit duller without dipping your toes into the unknown, you know? Even just a little bit of it. It’s still hard to do, of course. I constantly find myself in situations where I am just sort of making it up as I go, which isn’t comfortable, but I’ve learned that as uncomfortable as that feeling is, it’s also where I learn the most. It’s a bit weird in that sense. When I’m not really under pressure I find it’s easier to be lazy and unadventurous, which is no fun at all. Read more>>

Isabel Muller | Founder & CEO of Swtch Underwear

I associate risks with “gut feelings” or intuition, which I think have driven most of my life and career decisions. For me, there seems to be a pretty noticeable categorization of making moves: 1) planning things out completely 2) planning things out a little, and 3) just going for it. I typically “do life” between #s 2 and 3. I have found that if I lived by #1, I’d never do anything out of the fear that comes with trying to master the future. I’ve learned to trust my intuition, and as cheesy as it sounds, live life like it may end tomorrow. Read more>>

Patrick Perfetto | Music Producer/ DJ

I believe that risk taking is essential to any growth as a person and in business. Failure is part of the success story that no one likes to talk about. Every successful person has failed multiple times before achieving their goals. there is a back story to each person, and those trial and tribulations make them who they are. Hardships create character, and makes you hungry to achieve top tier results. Risk taking is scary, and most people try to avoid risk in life. It is an essential stepping stone to get out of your comfort zone. A lot of people want to stay in their comfort zone for as long as possible. It’s impossible to avoid if you want to get results. Risk is important for you to become the best version of yourself. I have failed multiple times in my career, from a failed music festival, to getting declined by record labels. Its simply just part of life, and you need to keep pushing harder. Read more>>

Luka Tartaglia | Actor, Writer & Director

If you start from zero but having a vision, risking is the engine to achieve the goal. If you decided to risk it means you love yourself enough . It means you’ve put your will ahead of all your fears, doubts and insecurities. Risk taking is growth, whatever it brings into your life. Positive or negative it’s still experience. I’ve risked everything to follow my vision without any certainties about the future and it has been the best choice of my life. Read more>>

Myriam Glez | Founder of Athletes Soul

For me, risk taking is about seizing opportunities. I never had a set career plan. I didn’t have five and ten years plan or a dream job. In hindsight, I think this was good because it gave me the freedom and open-mind to chose my next move. And it gave me the flexibility to coordinate my career with my husband’s. If you look at my career from the outside, it seems that opportunities would just present themselves to me but there were available because I was available. I wasn’t afraid to leave my job, move to another country and try something new. That allowed me to travel and work in five different countries. And when the move was for my husband ‘s job, I took it as an opportunity to reinvent myself. Read more>>

Chel Strong | Rap Artist and Song Writer

I was born into a family of risk takers. My father, Barrett Strong a legendary grammy winning singer/songwriter did not just get that title by following a blueprint necessarily, but with the assistance of hard work and taking many risks that ultimately turned into rewards. This way of life was definitely bestowed on his family which heavily impacted my way of going about things in pursuing my own career as artist/songwriter. I like to think of risks as possible doors of our destiny. You may open it and worst thing that can happen is you realize your destiny is behind another door, but you never will find it if you don’t open those doors and take those risks. Taking risks have played a major role in my career, I remember I quit my job at the Apple Store to pursue my dreams as a rap artist, and although challenging, it ultimately got me to where I am today. Read more>>

Jeremy Deputat | Photographer + Art Director

Everything you do in life is a risk. I was raised to have no fear (within reason) and take risks, and that has shaped such a big part of me today. I normally don’t take a short term risk, like not looking when I cross the street, that’s a dumb risk, but I feel like longer term risks are necessary to evolve and push forward in life and your career. In my past career, I worked as an art director for 10+ years with a solid job, benefits, etc. When my passion for photography really started to consume my life, I made the decision to quit my day job and pursue a photography career. I didn’t any clients, didn’t have a plan b, didn’t have tons of savings to fall back on, and really didn’t know how I was going to pay my bills. I wasn’t nervous though, because I believed in myself and my creativity, and knew if I worked extra hard and gave it everything I had, things would eventually work out. If I wouldn’t have taken that risk to quit my job and become a photographer and run my own business, I wouldn’t be traveling the world doing what I love and still probably stuck at my desk in that depressing office. Read more>>

Dani Everson | Salon Owner/ Skincare App

have always thought being an entrepreneur was far less risky than living under someone else’s rules and restrictions. When I got pregnant at 17 and had to tell my parents that I didn’t want to attend college, instead I wanted to pursue a career in hairdressing, I was shamed by a family friend that was “risky” and irresponsible to be a young mother and entering a career of instability. I didn’t see it that way. I was so excited to be entering a world of endless possibilities, endless pivotable career choices within the field as well as a chance to be thrilled at what I was doing/creating as opposed to a 9-5 job. My husband and I opened our first salon while 9 months pregnant with our 2nd son. We put 100% of our savings into the salon so that my husband can stay at home with our son and I would be able to work behind the chair. Looking back that could have been risky, but in the moment it felt like the right choice and an easy enough dream to achieve. Read more>>

Owen Scarlett | Dancer, Web Designer & Photographer

In my career, risk taking has forced me to remain present and by doing so I allowed there to be space for new opportunities. I found that by constantly taking steps into the unknown I diminished limitations that might have arrived had I stuck to more linear pathways. Read more>>

Brandon Elliott | Musician, Educator, Consultant

Risk-taking is essential. The problem of risk is that no one wants to be the first to risk failure, and everyone wants to be the first to claim success––but one must be willing to fail to succeed. It is safe to say that very few people enjoy risk. It’s probably also safe to say that most people are risk-averse. But, being risk-averse doesn’t mean you don’t take a risk. The more we normalize risk and realize risk is a daily practice more than some pivotal event, the more we might be willing to take the first step. Think of all the small risks you take every day: driving to work, crossing the street, giving that meeting presentation. These daily practices have inherent risk, and we all live to see the sunrise the next morning. The more we embrace this daily practice of risk, the more capital we build within ourselves to take on more significant risks. Each time you step onto the stage, sing or play a note, or share your art with the world, that is a daring and risk-taking endeavor. Starting an organization or business is also a significant risk; failing is often greater than the odds of succeeding. Read more>>

Chantal Casutt | Actress & Screenwriter

To me, risk-taking is a fundamental part of both personal and professional growth. Without it we cannot really learn or change. Having said that, I think taking risks is simultaneously one of the scariest as well as one of the most important things to do, regardless of the job or industry. You never know if a risk is going to pay off but having the courage to try is at the core of so many peoples’ success. I wouldn’t be here today if I hadn’t taken some major risks. Growing up I thought I knew what I wanted my life to look like: work in a big corporation, have a high-level, well-paying job, come to work wearing a blazer and sit in a glass office overlooking a big city. And for most of my life, that was what I was striving towards. I moved from Switzerland, where I’m from, to the UK to get a degree in management and marketing. I then went on to move to London where I worked as a marketing intern in a multi-national beauty company for a year. They offered me a full-time job after I completed my studies and so I had everything right there in front of me. Job security and a good salary right out of university in one of the world’s most interesting and diverse cities. Read more>>

Allyshia Gupta | CEO/ Founder of Jewls By Lee

Jim Carrey once gave a speech about risk that has stuck with me since. He began by explaining how many of us will spend our entire lives “imagining ghosts and worrying about the future.” We consume ourselves with the destructive thoughts of all the things that can go wrong but rarely stop to imagine all the things that can go right. Every decision we make in life is either out of love or fear and I, like many, had been governed by fear disguised as practicality. I was working jobs I didn’t like because it felt safe. As I was walking into the office one morning it hit me that I would spend majority of the rest of my working life and career doing something that I dreaded. That same day I gave my two weeks notice and never looked back. I do not claim to know the deep philosophical meaning of life, however, I do understand the sanctity of it. We are given only one life and I believe we have a responsibility to ourselves to enjoy it. In my opinion, life truly begins the moment you are not afraid to fail, to risk, and to dream. Read more>>

Katie Cali | Film Editor

I have set high goals for myself since I was young and because of that I am always pushing myself to do my best and nurture my creativity. When I was a kid, my best friend Laura and I started our own production company in my attic. I would write scripts and she would work on costume and set design for our mini movies. I was obsessed with Lucille Ball, Marilyn Monroe, and the glamour that Hollywood seemed to be – I knew at a young age I would move to LA and work in the industry one way or another. Coming from a small town in Illinois, that all seemed to be just a big dream… but in the back of my mind I could not let it go. When I graduated from college all of my friends were moving to downtown Chicago, but I knew it was time to give Los Angeles a try. I moved to Santa Monica without knowing anyone here into an apartment I furnished with just a bed, a sofa chair, and a tv. Shortly after I met an editor, Grant MacDowell, who gave me a shot at being his assistant. I absorbed and fell in love with commercial editing. I am fortunate to have a career where I collaborate with people with the same passion. Without taking risks you never know how far you can go in building your career. Read more>>

Bless It Clothing | Faith-Based Clothing Line

Life is nothing without pursuing the unknown. The same is true in business and life. Growing up, “risk” was always taught to be a scary word. We were taught that if you do not follow the blueprint of those before you, you are destined to ultimately fail. Stepping out of that restrictive mindset, is what will set you apart in business and life. The unknown is that for a reason because you cannot determine what lies ahead. However, you can eventually know once you take that step. Many people in business and life will talk themselves out of opportunities, based on lack of education, experience, or resources. But the real reason is, fear. Fear of the unknown. Bless It Clothing has taken on every risk and challenge that has come our way. There are things that we do not know about the industry and business in general. We take the time to make mistakes, educate ourselves, and learn along the way. Read more>>