Taking Risk is essential, but how much, when and why? Taking risks effectively is as much of an art as it is a science and we’ve asked some of the brightest folks in the community to tell us about how they think about risk taking.

eli james | Drummer turned Celebrity Fashion Designer

Risk taking is a must if you want to grow.. and it’s funny because the most rewarding risks all seem to have happened by “accident”. Meaning I was never “looking” for the opportunity, per say, it just came to me as I was doing my own thing. I have a random idea “I want to make my own clothes” + a very fun and strong feeling to just move forward with this crazy idea.. these crazy ideas that definitely do NOT have a guarantee for any success and with a twist of close friends and family maybe doubting it.. But then.. BAM, the opportunity rises and the risk taking begins! then I move forward and BAM another opportunity and BAM another.. with ALL these opportunities having very scary growing pains and sometimes very little reward.. but we just keep on going. One foot in front of the other. This is where our slogan “Just Be – The Rest Will Follow” really came from. I am an artist, a drummer, a (now) celebrity fashion designer.. I mean who would have thought?! So with that said, YES! Risk taking is a must. Read more>>

America DeLoach | Food Entrepreneur

I like taking risks, and quite frankly, I don’t often have time to think about the consequences. It gives me a thrill to take risks and anticipate how it will unfold. That feeling is much better than wondering what if. I let my intuition take over, and so far I’ve been more lucky than sorry. Obviously, as we grow, I have started to give more consideration to risk analysis when I make decisions for the company. Read more>>

Germôna Sharp | Vocalist|Actress|Writer

The way I think about risks is, I don’t. I at the very least try not to think about it at all. Once I make the decision to do something that is out of my comfort zone, I weigh the possible outcomes. Usually it is necessary that I do what i initially want or need to do and I just go for it. I have gotten many acting roles and opportunities because I put fear to the side and took the risk. Read more>>

MAXI Nickou | Musician & Artist

Taking risks is a huge part of being a musician. You have to learn how to let go of financial stability. Going from a sales job with weekly paychecks to gigging full time, was definitely a difficult transition. However, with great risk comes great reward. If you want to chase a big dream you have to be comfortable with taking big risks. Read more>>

Michelle Chisolm | Founder of Twice As Good Consulting, Creative Consultant and Brand Storyteller

I think of risk-taking as a necessary means in reaching the other side of the unknown. If you always knew the exact outcome of a choice, life would have zero surprises for you and everyday is Groundhog’s Day. However, I am a huge fan of calculated risks. (Some may call it overthinking but I’m a Taurus and the the math will always have to math to an extent.) Taking risks has always meant that I’m an active participant in building my life. In both my life and career, risk -taking has only brought me the necessary courage, the respect and support from those around me that believe in my journey. Risk-taking is the pursuit of happiness. The pursuit of success. The pursuit of freedom. Read more>>

Crystal E. Green | Writer | Director | Producer

I don’t believe that there is an alternative to taking risks. Every time that I make any decision about my life or career, big or small, I’ve taken a risk. A risk which sacrifices comfort or convenience. A risk that may or may not have been accurately calculated. A risk to abandon predictability for dreams. But life continues to show me that even if I don’t willingly choose which risks to take, doing absolutely nothing is a risk all in itself because I’ll forever wonder what may or may not have been as I uncomfortably settle into the risk that resulted from not choosing. Read more>>

Sepideh Hakimzadeh | Mother, Psychotherapist, Visionary

When I think about risk I don’t think about it in the conventional way. For me risk taking is defined by following my intuition and not what is expected of me or what something is supposed to look like. I allow myself to feel into what is guiding me — my guides, ancestors, and intuition. This has meant that things have felt harder and success as we define it within Western culture has come later in life. Marriage, children, a successful career. But it also means I feel confident in my choices and life path because I have chosen to take a path that is not as direct and obvious which has allowed me to do deep healing and trauma work and connect me to my spiritual path. I think it’s an act of revolution to allow your spirituality (not as defined by organized religion) but nature based and ancestral based spirituality to guide you. Read more>>

Lauren Zavala | Designer and Artist at Zavala Bespoke

Risk has always been a tricky thing for me. In my personal life, I would say I am pretty risk averse. I’m careful and really put a lot of thought into everything I do prior to doing it. In my career and with my art, I have had to unlearn a lot of that. I’ve spent a lot of time learning to be up for anything- even if it scares me. I try to be “game” for whatever comes my way. In my experience, it’s best to expect the unexpected. I know how cliché that sounds, but it’s the best piece of advice and the hardest thing I’ve had to adapt to. Art in and of itself is a risk. Read more>>

Remi Shimazu | Online Business Owner & Content Creator

I think about risk differently after 2020. 2020 was a stark reminder of how fragile and unpredictable life can be. It gave me the wake-up call (and time) I needed to figure out what I wanted to do with my life. It gave me the understanding that we need to be as intentional as possible with our time and enjoy every day of our lives. 2020 allowed me the opportunity to re-evaluate my priorities. I created a list of non-negotiables for the life I wanted to live post-COVID. And then actively started looking for ways to achieve that life – that’s when I stumbled upon the world of blogging and content creation. Read more>>

JohnBorn | Renaissance man

Taking the risk was the determining factor in any success I’ve accumulated. I left my hometown with nothing but a backpack and enough money for one meal. I had to sleep in unthinkable places & starve for days at a time, although without that leap of faith you would not know who JohnBorn is. I’m am the definition of a risk taker, Read more>>

Joan Goodspeed | Host of BreaknRemake | Educator

I’m getting more comfortable with risk. Is it because I’m getting older and I have a better baseline knowledge? Or is it because I’ve learned no one knows what they are doing? There is comfort in both of these, but I think it’s only part of the puzzle. There is no handbook for creative work, we are all doing our best-guess path. I am the person that will see to my success, writing my own guidebook. That can feel isolating, but exhilarating as well. By surrounding myself with supportive people and asking for help – yikes! – I’m able to get pushed or comforted when each is needed. Frequently at the same time. And I’m trying to change my perspective on the dropped out stomach rollercoaster feeling from terrifying to wow isn’t this exciting. Ultimately I know my purpose is to help and inspire people. So it comes down to this – to reach people and help them I need to keep creating. Read more>>

Spencer Williams | Photographer and Political Strategist

Risk is inherently a frightening topic at first glance. No one likes losing something important to them, and the thought that the loss could come as a direct result of a choice they make, especially when the option of not making a choice at all is on the table makes the initial risk itself even more difficult to navigate. For me, my idea of taking on risks has evolved from one that I feared into something that over time I have grown to understand will never leave. You cannot defeat risks by not taking one, nor by taking them and seeing them pay off. Risk is part of the game. Read more>>

Gary Kohn | CEO/Co-founder of Luxury Travel Hackers

I don’t ever remember a time in my life when I didn’t make risky decisions. I think for the majority they haven’t paid off but if I really think about the amount I’ve learned both through success and failure has been intense to say the least. I do thin k the thing that comes with age though if you are a risky person is the thought process around calculated risk. Before I started Luxury Travel Hackers officially I was making a huge career change…at 49 years old! Read more>>

Darlene Bryant | Educator

Risk is necessary in order to challenge your mindset and to keep yourself from living with regret. You can recover if you take a risk and it doesn’t go as planned. It’s hard to recover from regret. Risk taking has helped me build the confidence I needed to be successful in my career. Read more>>

Dean Banowetz | Celebrity and Show Hair Stylist

How do you think about risk what rule has taking risks played in your life and career? Whenever I think about a risk I always think to myself a risk is an opportunity to elevate myself to the next level. In order to elevate and prepare for that risk all you need to do is research and prepare and believe in yourself.
“My mother always told me if it was easy everyone would do it so take the chance/risk and make it happen.” Read more>>

Nicole elizabeth | Int. Published hairstylist and men’s grooming specialist

Risk taking has definitely been a huge factor into becoming who I am today. Growing up in San Diego California and moving to Los Angeles doesn’t seem like a big step, because it’s less then 200 miles away, but what people fail to understand is that when you get here the progressiveness of Los Angeles as a barber / hairstylist is a bit more intimidating then you might have imagined and because of that alone a bigger city means more people , more people equal more jobs , more jobs creates more money and when theres more money there is a higher turn around! I had to really learn how to take risks to get the place I am today because i realized that if I don’t i will be replaced by someone who wants it more and or I will stay stationary. I think everyone needs to takes risks sometimes in order to get to the next level especially in their career out grow your growth ! Read more>>

Judy Reesha | Owner

I don’t consider myself to be a risk-taker, but I do think I’m brave. I’m willing to put myself out there and can see failure as just a part of growth. It makes risk-taking easier when you know you’ll bounce right back! The trajectory of my life and career didn’t involve a lot of recklessness or risk-taking. I’m not a rule-breaker, didn’t have a rebellious phase and sort of fantasized about what that could mean for me later in life. I guess when the opportunity presented itself to buy a business – I knew it was risky – but most of my risk-assessment came from the impulsive, instinctual side; I relied a little on others to assess whether it made intellectual and financial sense. Read more>>

Jaron Crawford | Actor, Musician

Risks are the foundation of my artistic pursuits. With each step of a creative process I encounter a point in which I have a choice; mind or gut? My mind is like an overbearing mother that calculates the possibilities and outcomes of my future, while my gut is like a mysterious stranger that shows up at my door… asking for shelter. If you know me, you know I’m letting them in 95% of the time… unless they’re foaming at the mouth, ya know? But even then, I might regret leaving them out there to die so… I gotta trust my gut! It helps me live without regrets. I think a daily risk is trusting my gut, even in situations when my mind says otherwise. Read more>>

Louis Quantrille | Fashion Stylist

I think that taking risks has a pretty big role in my styling. I don’t ever want to play it safe or stick to what I’m comfortable with. I am always trying to push the envelope and do something different. As much as I love trends I try to steer away from them and draw inspiration from past eras and my Seattle grunge roots (this is how I believe I take risks). Read more>>

Amber Payan-Inclán | Insurance Agency Owner

I think of risk as a necessity. A non-negotiable in my life. Sometimes the idea of risk is uncomfortable and scary, but the idea of staying stagnant, not growing, being the same person in the same place year after year is much scarier to me. I realized a long time ago that there will always be fear, but I refuse to let it control me. Taking calculated risks has played a big role in my life and business. It has pushed me and challenged me to evolve into the person and leader I was meant to be. I still have a long way to go, but looking back it amazes me how far I’ve come. Read more>>

Jessica Brown | Hair Stylist & Makeup Artist

I can honestly say I enjoy taking risks within my career and my life. I don’t think I’ve always been this way, but I’ve enjoyed the journey.. It’s not always easy but I find it to be very worth it. I recently moved to Texas from California with no clientele and barely knowing anyone. Moving was a huge deal for me as I was leaving a whole life and clientele behind. Read more>>

Omar Juarez | Filmmaker

I think life is all about risks, the moment that first fish waddled out of the ocean and became the earliest pioneer to pave the way for us all; gave us feet to move and evolve. Stepping out of your comfort zone and taking risks is scary, but the scariest risk I think is doing nothing at all, because then you risking everything. All the possibilities that could have happened, all the victories and failures that taught me what it meant to succeed. None of that would have been possible if I never took a risk and believed in my dreams. Read more>>

Cole Cavallin | Writer, Painter, photographer, journalist

Risk Taking was an extremely important part of my artistic career and growth as a person. Jumping off the edge and having complete faith in an idea takes discipline. I still Remind myself constantly of why I made the decision to take a risk, the stakes are high, strengthen your imagination and remember the circumstances that got you to a breaking point from your old life. Read more>>

Michael Basic | DJ, Magician, Capoeirista

I think risk is extremely important, but I also think its viewed incorrectly by society. To me, failure is the only way to really learn. If you always take the easy path, and never have much risk of failure, you don’t learn much. This is dangerous because the difference between someone who has a passable skillset and someone at the top of their field is, in large part, how they deal with adversity. The best show of a person’s skillset is how they perform when things go wrong. Failure doesn’t seem to fit into today’s social media driven world of only showing your perfect self to the public, so lots of people avoid anything difficult at all costs and suffer for it. Read more>>

Max Marshak | Wine Maker and Father

The great moments of personal growth in my life have all been influenced by risk. In fact I would say that risk was the catalyst for movement and good change. I grew up on a small island off the northwest coast of Washington State. This was a very rural, small town world. Despite this, I was influenced by many worldly and open minded mentors and teachers in that place. These positive influences however could only go so far. So when I decided to move to New York City to pursue a romance with a girl I had only just met, I was way out of my safe zone. I packed a suitcase and just went for it. Read more>>

trout baseline | Singer-Songwriter, Producer, & Multi-instrumentalist

I think risk taking is extremely important. However, I also think you need to choose your risks wisely. Pursuing a creative/artistic career is in and of itself a huge risk. This career path lacks the security that other paths promise. However, the payoff can be worth it a million times over. I think I am a little risk adverse by default. Knowing your default level of comfort with risk is paramount. If you know you’re a little risk adverse by nature, like me, you have to constantly challenge yourself and ask yourself if you’re playing it too safe. Read more>>

Terence Hamers | DJ & Producer (TER3NCE)

I think taking risks are very important in life, but be cautious. I’ve taken the ”risk” to just walk down to people and ask what they think of my music. I’ve taken the ”risk” to go to a management team while I was just at the beginning of my career. Not a lot of people do that and I think in order for any kind of success, you need to take the risk and just go after it. It can be anything, maybe you’re struggling with a project that doesn’t really work out in your eyes, or maybe you haven’t heard just enough feedback for it. Feedback is the key to get something at a perfect level, of course your own personal preference is what’s the most important, but hearing what other people think about your product is really worth a lot. Taking risks have taken my career to another level, by doing that i’m now working with a music label and management team. But you always have to feel your gut, if it doesn’t feel right, then don’t, but if it does, then go for it. Read more>>

Orissa Jenkins | Animation Background Designer

Before I take on a risk, I consider my basic needs first, like shelter and safety. I then consider my time. I try to make decisions that I think will benefit me the most in the long run. When I made the move to Los Angeles a second time around, I had saved for a year’s worth of rent. I felt more confident with my skill and had friends in the animation industry to help guide me. Read more>>

Mikayle Cole | CEO

Taking risk has played a big part in my life. I quit my job working as a paralegal at a law firm and went to do my own thing. My own thing being my own anything, i had no full plan. From there i started my logistics business. I sold my own modded car to buy a truck and trailer. Gas and insurance were through the roof for me but it paid off. You just got to remember the bigger picture and get it done everyday. Life in Atlanta everyday is a risk! Read more>>

Calvin Lai | Fine Art Oil Painter

One of the many tools in my artistic toolbox, is the ability to embrace and, at the same time, temper risk taking. It’s an essential element for making work that is unique and relevant both to one’s self, as well as to the greater art audience. For my own satisfaction, I am always wanting to explore different ways of painting. I have to do this in order to create pieces that are fresh for myself, and for creating unique work amongst the vast amount of art out there. But taking risks can also scatter the artistic vision and confuse a viewer, and without building a cohesive style within a long term art career one’s work becomes weaker. Risk without temperance loses sight of the broader vision. The trick I find is making sure you are very mindful about taking chances. For me, this has opened me up to reaping the benefits of risk taking while building upon a recognizable body of work. Read more>>

Crystal Duran | Business Owner, Entrepreneur, Choreographer and Dancer

My whole career has literally be about risk taking. Opening up a dance studio isn’t as easy as people may think. It takes a lot of courage, confidence, promotion and thinking outside the box. There’s a lot of competition out there, so I have to keep things fresh and exciting. I base a lot of things on faith and I had to have that faith to make this dream of mine come true. I knew I had to take the risk to get my own studio and I’m so glad I did. I think risk is necessary for career growth and potential as an entrepreneur. I took a risk and opened up a second dance studio during the beginning of the end of the pandemic and seeing the fruits of labor has been rewarding. Read more>>

Destiny Burns | Owner/Founder, CLE Urban Winery

I am the Queen of Reinvention… and I think that being able to reinvent yourself and your circumstances as many times as you need to is one of life’s great gifts. It does involve risk taking, however… but the potential rewards are endless. I was born and raised in an inner-ring suburb of Cleveland, Ohio, comprised mainly of working class Eastern European immigrant stock. I was the oldest of 4 kids, my parents struggled to make ends meet, and I carried a heap of family responsibility on my back. I got my first W2 job at 15, and I also babysat like crazy to earn some spending money. The first big risk and reinvention I undertook was to apply to be an AFS foreign exchange student at age 16. I found myself in Italy, which opened my eyes to the wide world and all its possibilities. There was no turning back to a quiet Ohio life after that. Read more>>

Michael Ken Stewart | Photographer & Branded Content Producer

Taking a risk by going out on your own as an artist and freelancer is scary. Creating system in where you can think about how much risk you are willing to take on is important. One thing you can do is create a personal budget to figure out how much money you need to make month to month makes risk less of an abstract idea into a more concrete calculation. How many clients do I have to secure? What rates do I charge? Do I still need a part-time job or full-time job to build out my skills and network while sustaining myself? These are all important questions that you can ask yourself to make the idea of taking a risk a tangible negotiation with yourself. Read more>>

Matthew Bagnall | Producer / Recording Artist

I think about risk as something that is tied with a great reward. But to get that reward you have to take that risk. As a kid growing up in small towns across the midwest, the career path of a successful musician was seen to be something very risky and unattainable. I was surrounded by non believers. Thankfully, I was raised by supportive parents that pushed me to always dream big. When it came down to my choice to seriously pursue music as a career for myself, I had to think about what mark I wanted to make in this life. Deep down, I believed I was able to accomplish anything I dreamed of in this life, so pursuing my great passion for writing and performing music was an absolute no brainer to me, despite the risk. Read more>>

Shagun Sharma | Experiential Valedictorian

I take a lot of pride in forging my own path on the road less travelled. This is a game that comes with a lot of pitfalls, a lot of detours, and a lot of uncertainty. Every move I make is a risk. There’s always a chance that a song might not stream very well, or that a music video might not circulate very well on YouTube. There’s always a risk that the money I spend behind a product might not pan out. I might not get the return on my investment. But that’s what comes with the territory. I think taking risks is what defines you as a player in this game. Shouldering great risk and turning it into a grand reality is the mark of a successful artist. Read more>>

Lara Schmoisman | Founder & CEO of The Darl

Taking risks is inevitable and a big part of being an entrepreneur. Sometimes you have most of the facts on hand and can make calculated decisions, sometimes you just have to dive into the pool and hope for the best. Ultimately, in both cases, there’s a little bit of “faking it ‘till you make it”. I know it’s a cliché we’ve heard a thousand times, but hear me out. On numerous occasions, you are going to apply for a job or pitch a client and find yourself in a situation where you might not be exactly sure of how to proceed. That doesn’t mean you have to pass the opportunity, it just means that you have to work harder and learn a few new tricks in order to get the job done. Read more>>

Marc Chitwood Nicholas Stoks | Marc Chitwood | Executive Chef and Owner … Nicholas Stoks | General Manager and Owner

Nicholas: There will be risk involved with any endeavor you take on—and the bigger the goal, the bigger the risk. Obviously, in starting a restaurant, there was a great deal of risk involved, especially considering that, in our case, it was two people who had worked in plenty of restaurants but had never owned one. If you want to grow, then taking risks is a given, but with Marc and I, our work ethics and communication are so well-aligned; he is a business partner you can count on in any situation, which made taking those risks less scary. To me, taking risks, regardless of the outcome, is an opportunity for growth, both personally and professionally. Through the highs and the lows, we have learned so much about ourselves, and about this profession. It was a risk, for sure, but I would do it again in a heartbeat. Read more>>

Francesca Maria | Recording artist, songwriter, performer

I simply wouldn’t have a career without the risks I I have taken in my life. Starting from moving to New York City from a small town in Italy when I was very young to pursue my dreams, then dropping my dance career to focus on my music. Every project I start is a leap of faith. As an artist you don’t know if the project you invested your money, time, body and soul on will be successful but you do it anyways. Listening to your gut feelings despite what labels and stats say is a risk I took many times to serve my integrity as an artist and human being. Even Love is a risk so… can we say that we are really living our lives without taking any risks? Read more>>

Simone Smith | Retail Nursery Owner & Columnist

It’s interesting to think about risk, it definitely signifies taking a chance and doing something that most others wouldn’t. When I first opened my nursery I remember my cousin asking me “So, what’s it like to start your own business?” I answered, “Well, I guess it’s a lot like bungee jumping, screaming as you fall, hoping the rope doesn’t break and that you bounce back up!” No matter how much preparation, it’s exciting, scary and invigorating to take that step. Read more>>

Helena Goto | Workplace Performance Coach and Consultant

Risk to me is opportunity. Taking risks has, without a doubt altered the course of my life. At 20 I was living in New Zealand and randomly won a trip on the radio to Los Angeles. Obviously – having never left NZ, the Kiwi dollar being 36 cents to the American dollar, and knowing no one in America, let alone NY – I decided to go to NYC for two months before I met my boyfriend in LA for my “Hollywood Experience”. When I arrived in New York, I felt at home for the first time in my life. That was a big deal because it made me realize there wasn’t anything wrong with me, I just didn’t fit in in NZ. Read more>>