Risk is the most common topic that comes up in our conversations with entrepreneurs and so each week we ask entrepreneurs to talk to us on the record about how they think about risk.

Melissa Parsons | Certified Life Coach & Pediatrician

When I was younger, I took a relatively risk-free path of becoming a pediatrician. This path took hard work, determination, discipline, and patience, but there was not much risk involved. It was a huge risk to make the jump from being a pediatrician, working as a partner in private practice for 22 years, to becoming an entrepreneur, working only for myself. I saw a recent video on tiktok by @rogerskaer and it really resonated with me… the more you are willing to f*ck around, the more you will find out. At this stage in the game, I have the luxury of being able to f*ck around, fail, and find out until I consistently f*ck around, succeed, and find out! The more risk, the more reward! Read more>>

Lu Paul | Illustrator, muralist & designer

I’ve always been a big fan of risk-taking. I find it fun. The adrenalin of getting out of my comfort zone, not knowing exactly what is going to happen, and taking control of my own life. At first, of course, one is nervous… but the key is: whatever happens you know you tried. You won’t ever live thinking about “what if”. And that simply brings me peace, knowing I did everything I could in life. If I hadn’t taken risks and worked hard, I wouldn’t be where I am today. Read more>>

Hyunjin Lee | Filmmaker

I was the person who always tried to avoid the risk. I studied business so it was natural for me to analyze the potential risk and minimize it whenever I made a decision. Every path I chose had more chances to succeed, or I had a safety net in case it doesn’t work. However, one day, I realize that the ‘safe choices’ I’ve made so far were always my second favorite ones. I was too afraid to take the risk to go for what I truly wanted, so I compromised it. Especially in my career, I wanted to be a creator, but never fully devoted myself to becoming one, and took a job in a similar business. Read more>>

Schreen Gomez | Entrepreneur & Business Development Consultant

I learned about risks early on. When I think about the role it plays I often find that it’s not just about finances, there are other opportunity costs involved when you make the commitment to doing something that is opposite of everything you learn as a kid. Everyone tells you to make calculated risks, and or be “risk averse” but the literal concept of risk, is a risk lol. What I understand now as an adult after having been put in environments that drive two narratives around risk; is that : 1. You have to be fearless in your approach to becoming who you’re meant to be, You have to jump every time on the first thought no matter how stupid it looks to everyone else, or you risk the opportunity of getting closer to the vision you see for yourself. Read more>>

Raoul Bubber | Multidisciplinary Animator & Illustrator

Risk is something that most people fear in life, including my own. The idea of having to make a potentially rash decision in a split moment is a very jarring one. However, if it involves something that may make one’s career, it’s a risk that one would probably regret not having made for the rest of their lives. In my case, soon after graduating from the School of Visual Arts in New York, I was suddenly presented with the opportunity to Co-Direct the Official Visualizer for late rapper Juice WRLD’s ‘Already Dead’; a posthumous release of one of his songs. Read more>>

Julia Granacki | Health Coach

I’m a 46 year old women with a cushy corporate job that has a 401k and complete financial security, but I’m miserable. I call this predicament the “golden handcuffs” problem –where you feel like you have to choose financial security over a career that you love. It took me a very long time to reject that statement, but here I am, embarking on a brand new career as a health coach, working for myself, and not knowing what the future will bring. I’m both excited and terrified but nothing ever comes of playing it safe. Risk is defined differently by each individual. In my case, I’m blowing up my entire life to see what is on the other side, but I think it will be worth it! Read more>>

Giuseppe Calvinisti | Artist (Actor, Photographer, Painter, Human Extraordinaire)

Well, Risk has been and will always be a part of every person in their life. I see it as a normal process of existing. I’ll try to explain. Risk is an elemental part of growing and that risk achieves, (sometimes uncomfortable) goals. So, early man, risk their lives by hunting, I risk talking to this girl even though she might turn me down, I risk stepping into the karaoke platform at the local karaoke bar, I risk failing in that exam when I preferred having fun the whole semester, I risk not being happy if I do not pursue what makes me truly tick. So, after all my life being in the corporate world and having suppressed my love of expression in the arts, I risked it all by quitting and jumping into the world that I believe I was meant to live in. Read more>>

Darin Klein | Curator and independent publisher

I don’t look at risk in the traditional sense of the word – risk implies that there is the potential for failure. Of course when I look back at my life and career I can see that I have taken a lot of wild chances, made things up as I went along, and generally followed my own instincts rather than going down beaten paths. Have I succeeded in all of my efforts? I think I have – event if the end result wasn’t exactly how I envisioned, at least I tried, and then I had that experience and knowledge to guide me in my next projects. Read more>>

Jesus JFLOW” Flores and Angel “SGN” Romero NA | Educators & Writers”

SGN: I am currently an educator based in the San Fernando Valley. I serve as the English Language Development (ELD) coordinator at my school. What sets me apart from others is that English is my second language. I am an English Language Learner who became English proficient in the 7th grade and now supports students with improving their English proficiency. It’s quite fascinating and emotional to think about how things came full circle for me. At one point, I was the kid in ELD (English Language Development) classes, and now I’m the teacher supporting kids in ELD classes. Getting to this point in my career was not easy but I had a ton of help along the way. Read more>>

Vanessa Machin | Public Artist, Designer and Communications Specialist

In many ways the achievements I feel proudest of have felt like massive risks at the beginning. When I started college as a first generation American I felt lost and overwhelmed. When I put together my first art show, the process of gathering artworks, securing the venue, marketing, etc. felt insurmountable. Even learning to ride a bike is scary until you figure out how to pedal. Read more>>

Mona Martinez | Hair stylist and visual Arti

I’ve always been a risk taker. I moved to NYC with 600 dollars and I survived, found a job and a place to live. I have always been fearless and experimental in my life. I like to change it up. As an artist I get bored once I master something so I find new things to learn. I also left my fancy job to go teach English in Spain. I needed a change of scenery and something new. I love languages and people and culture so that was a great experience. I never let money stop me from doing something. I always find a way to get by with all my skills.  Read more>>

Sabrina Bezaire | Restaurant Owner & Manager

“Risk can bring the biggest reward” was a quote from my college professor in my first business management class. That always stuck with me. I come from a family of entrepreneurs and although I saw my family struggle at times, having the freedom to make their own creative choices was ultimately rewarding even if the financial benefit wasn’t always there. Read more>>

Todd Pivetti | Not Your Daddy’s Realtor

I feel like so many people are naturally risk averse. Even the thrill seeker type- they know about consequence and risk. Myself? Well I was always the designated driver, the one making sure everything was safe, and the one who didn’t want to jump off the high dive. I naturally stayed away from risky things. It wasn’t until I moved away from home to the big scary city of San Francisco, (not that scary actually), when I started to realize that risk was necessary. I had dreamed of creating an interesting/successful life but never had the emotional wherewithal to make a jump. Read more>>

Chloëdees | DJ, Radio Host and Music Entrepreneur

Every time I step behind a set of decks ready to DJ to a room full of unknown people it can be one of the most risky things and it’s one I love doing. The challenge presented alone; a venue I could have played 20+ times can feel different once you step inside the room, the energy of the people and my own mood are all factors as to what and how I play on that night. The spontaneity of how my set is gonna go, which track to play next, what genre direction I might take it… You really never know and it’s that exact uncertainty I love! Read more>>

Sofie Rimler | Actor & Comedian

Everything in life that’s worth it is usually hard work. That’s why risk taking is so scary yet so powerful – and ultimately so rewarding. Read more>>

Rianjali Bhowmick | Singer-Songwriter & Composer

Taking risks has been one of the biggest things to change the entire course of my career. I used to be so afraid of showing up because I was afraid of failing. But that was precisely the reason that I wasn’t getting opportunities – I didn’t even open myself up to the option of what I could do if I tried to take risks. Read more>>

Paul Wright | Fitness Coach and Personality

I think it’s essential we try to do things in life that make us a little nervous or uneasy. Do things that scare us and that bring the feeling of adversity front and center. All this must be done socially, physically, mentally, emotionally, spiritually, and psychologically. I’ve always maintained this mindset as a professional because I know theres the next, best version of myself on the other side of any risk that I may take because theres always a lesson to be learned when attacking your fears. Read more>>

Deanne Moore | Mortgage Loan Advisor

My lineage is that of risk-takers. My ancestors did what they said could not be done. It’s in my genes and has led me on quite the life journey. When I was a teacher, I left the security of teaching – and a steady paycheck – and purchased a franchise. Most recently, I left education (again) and decided to pursue my passions in real estate finance. As a parent, it is super important to me to lead by example. It is always my goal to show my daughter that it is completely possible to do what you love and earn a decent living. Read more>>

Sam Sherwood | Vocalist and Songwriter for Dawn Fades

My whole young life I played the drums. I knew a little piano but never picked up a guitar or tried to write a song. In my early 30s I had some health issues that made playing the drums extremely uncomfortable. Around the same time I found myself increasingly dissatisfied with playing other people’s music. After a messy band break-up I picked up a guitar and started teaching myself to play. It was slow going but eventually a got a few songs together and demoed (badly). I vividly remember pushing “post” on craigslist with my first ad looking for members for Dawn Fades. Read more>>

Natan Pena | Photographer

Risk is essential in life, chasing your dreams and building a business. I have always looked at risk as a catapult for growth in any area of your life. Risk teaches you many things but mainly that, to grow you need to be uncomfortable and face the unseen. When you comfortable you don’t have the will or strength to move forward or take that step that can launch you forward. For me one of the biggest risks I have taken was opening up my business about a year ago, it was uncertain how my business would do, or if I’d be able to survive financially going completely freelance. But taking that risk has allowed me to see how important time and money are and just the idea that you can grow so much by making that one decision. Read more>>

B Line Dot | Artists & Creative

I think as I’ve grown up risk has become more of a factor. Early one I took more risks because I was really trying to figure out what worked. Even though not everything was hugely successful it taught me that taking those risks was worth it. I rarely have to spend any energy on what if. Now that we have more of a formula and we’ve carved out a path we still take risks but they are a bit more calculated. Read more>>

Bruna Portugal | Actress | Comedian

It’s a MUST! You won’t get nothing in life if you don’t take risks! 2 years ago I left my entire life and family in Brazil to take the risk of moving to LA and invest in my career. Read more>>

Andrew & Jackie | Design/Builders & Professors of Architecture

If the risk serves the purposes of fulfilling your goals and beliefs of your company, then it may be a good reason to do it even if the odds are against you. For us a decision for the company was to purchase a building/space to grow with a true maker mentality. We stumbled upon a saw-tooth truss warehouse that had been neglected for two decades and in need of a deep renovation. We had envisioned turning this warehouse into a space for design-build offices for builders, makers, and artists yet an overall gamble. Read more>>

Phaedra Achor | Founder/Owner/Maker at FloraLuna Apothecary

When I think of risk I immediately think of reward, personal and professional. But it has taken me a couple of decades to get to that point. Risk taking is part of entrepreneurship and I knew that if I wanted to be an entrepreneur I was going to have to take risks to bring my ideas to fruition and develop businesses. I have learned to surrender to the uncertainty and discomfort that comes with taking risks. I have learned to not be fearful of the fear that comes with taking risks, not let it inhibit me from moving forward. But also, I have taken small steps in my years of self-taught entrepreneurship. With every step and every evolution of business I have forced myself into new realms. Read more>> 

Brooke Clavesilla | Licensed Clinical Social Worker & Yogini

When I was thinking about letting go of the comfort of a full-time salaried position to pursue opening up my own practice as a licensed psychotherapist, my mentor and long-time friend told me, “Anything worth having usually involves risk.” As soon as she said this, I knew exactly what I had to do. It was time for me to quit my job, which meant giving up my salary and health care benefits during a global pandemic! Living alone with some savings, it was a risky decision to make. I was flooded with so many thoughts about paying my bills, cutting back on my spending, and maintaining the comfortable lifestyle that I had created for myself. Everything was uncertain, and I didn’t know if things would work out. Despite all the questions and worst-case scenario thinking, I trusted my mentor. Read more>>

Anna Calleja | Artist

Within artistic practice, risk and faith are inherit to creative process. The process of making work can be frightening, a leap of faith into the unknown. There are no long-term plans, I don’t know whether my next body of work will be successful or ‘good’ in any sense of the term. Dealing with uncertainty, financially and artistically has been the biggest challenge so far. You have to surrender to the process and have faith that something will happen. Read more>>

Candice Ferguson | Vocal & Live Performance Coach | C.E.O of The Performers Suite

Risks have always played huge part in my life, and I’ve always been a risk taker and one who has stepped out on faith. I feel in order to see the type of success you want to see, and move in the direction of pursuing your dreams, you have to take risks. You can’t sit on the sidelines, and at some point, you have to take the risk and get in the game. When it comes to risks, I think of how I was bold and left a comfortable salaried job working at a Property Management company. I dreaded going to work each day, and it was so hard to get out of bed. Read more>>

Jordan Biagomala | Cinematographer/Director

I take creative risks all the time. I find those are the moments I grow the most as an artist. It’s a cliche, but I enjoy learning the rules so I can break them in creative ways. I also take risks career wise. I’ve attended workshops, joined artist collectives, and passed on “sure thing 9-5s” in order to work towards the creative future I want for myself. Read more>>

Jesus Presinal | Dancer, photographer & creative director

Since I became a freelance artist at the age of 17 that was already taking a risk. I took a leap of faith into the world of dance and honestly i would never take it back, every day had its risks and obstacles but I still managed to figure it out and make the most out of it. Through the Covid 19 pandemic I dove into a whole other field of freelancing because the entertainment industry was down and the leap of faith has me where I am at today. Read more>>

Kristel Brinshot | Artist | Creative Coach

High risk, High reward, no risk no reward is pretty much my mantra although my version of risk might be different from someone else’s. I tend to be a calculated risk taker. If it doesn’t make me pee my pants I’m not thinking big enough, and if it makes me feel like I’m compromising who I am it’s not worth a drop of my energy. Read more>>

Tatyana Henry | Creative

I think that taking risks is essential to living a fruitful life. Without taking risks I believe that people are hindering their own growth and potential success. Taking risks has played a huge role in my life. I have discovered so many different interests and styles that I am into now because I took a risk and stepped outside of my own box. I always tell myself, “you never know what will happen unless you try”. Even then if it is a total fail the first time, you can not immediately cross it off your list because you might get different results when you revisit that specific task. Try everything, even if you are anxious of the outcome. Read more>>

Hannah Beth Richardson | Comedian, Actor, Filmmaker

Risk taking is about intentionally placing yourself outside your comfort zone. Early on, I got comfortable with taking risks. Growing up as a theater kid, I would constantly find small moments of comedic improvisation during a show. When they landed, the payoff was totally worth the scathing community theater director afterwards. Since then, I have been chasing that high, those golden moments you can find only if you’re fully present with the audience. The moments you could never rehearse or relive. They only come by taking a risk. Read more>>

Rūta Kuzmickas | Musician, Artist, Poet

As a classically-trained pianist, the idea and experience of risk-taking is one of the undercurrents of all things I do. Classical performance involves an immense amount of preparation and commitment, so every moment you’re onstage for a competition, recital, audition, etc. you’re either too careful and precious about all the work you’ve put in, or you throw caution to the wind and take the risk of trusting it instead. I find these days risk is in my experimentation with where and how the areas of my artistic life will lead me, whether or not I can be open to the next impulse taking form. Read more>>