Shoot your shot? Take a chance? Society bombards us with messages, phrases, examples and stories of how taking risk is the key to success, but is anything ever that simple? We asked some of the brightest folks we know to tell us about how they think about risk. We’ve shared their responses below.

Katie Gibbons | Actor, writer, producer, &… shellfish farmer

Oh boy… I sure have taken a lot of risks… and more often than not, fallen flat on my face along the way. I believe that no matter what happens… if I keep doing my best with the tools I have there will be a pay-off, even if it isn’t right away. I think about it like Newton’s third law: to every action there is always an equal (and sometimes opposite) reaction. Now, sometimes this reaction is negative (not the outcome you’d hoped for) and in order to be willing to take big risks with potentially major gains and/or catastrophic losses, a person has to have resiliency. I think to really commit to a risk-taking mentality a person must have tremendous self-confidence in their own resiliency. Read more>>

Jameson Burt | Singer-songwriter

As an artist if risk isn’t the starting point of every move I make, then I’m doing something wrong. Risk is the foundation of anything good that can happen in creating something. When you’re starting a new piece of music or a new page of words, there’s always a temptation or an impulse to go back to what you know, what’s worked before, or to imitate something you like. Read more>>

Kaella Madix | Event Designer, Fitness Instructor & Model

Many years ago my therapist gave me the mantra “feel the fear and do it anyway.” At the time, my insecurities and anxiety held me back from a lot of things both personally and professionally. Those words stuck with me. I started my event company based on that principle. I became a core40 instructor based on that principle. I started a fitness bootcamp and hosted a fitness challenge during the first year of the pandemic based on that mantra. You can say it’s become a life motto. I live by it. It was’t easy at first. The changed happened gradually, but the more I practiced pushing past my fear, the more natural it became to take risks. Those who know me say I’m fearless, but that’s not entirely true. I just don’t let fear stop me. Read more>>

Elisa Johns | Artist

Recently I’ve been taking risks in what I’m choosing to paint. I typically spend my summers sketching, photographing, and planning new series of work. This summer my daughter wanted to be involved in the process. During Covid she’s spent a lot more time at my studio and more time creating things. She really liked the idea that my newest works be a fantastical story. She wanted unicorns and butterflies and mountain lions. I decided to take a risk and play around with these themes in my work. I’m using iridescent paints and everything feels a bit sparkly and freer. I was definitely feeling a bit nervous about the unicorns but I’m actually really loving how they’ve turned out. It’s been a really incredible to make work with my daughter because she doesn’t censor herself. Taking risks is a really freeing and refreshing experience. Read more>>

Yatziri & Simon Lopez | Small Business Owners

In our opinion, risks are a must. Growing up I remember my mom saying “Si no arriesgas, no ganas” which translates to, if you don’t take risks, you won’t win. Some risks hold a higher value than others whether it is monetary, emotional, physical, or time. In our business, we have experienced all four, but we have tried to make the best out of it. The most common one is costs and where should we reinvest, how much, and how. Our constant question is “Can we recover our initial cost if this idea does not work out?” We are constantly looking at our cost and benefit of new projects and activities. Read more>>

Chris Zinkel | Risk/Reward

I view risk as an essential part of life – both personally and professionally. But risk takes many shapes and forms throughout the process as some can replace the word risk with others such as luck, chance, and/or opportunity. Some of the risks taken seemed trivial at the time but when you sit back and reflect, shows as intrical parts to our ‘us-ness’. Below are a few examples of risks and opportunities and how they intertwine. Read more>>

Chantal Winston | Founder of BLKessence

Risk-taking is something that has been significantly present throughout my journey with BLKessence. A few months before launching my business in October 2020, I decided to quit my teaching assistant job to go back to school full-time in pursuit of my bachelor’s degree, which was a huge risk taking moment in itself. After months of candlemaking, testing, and brand planning, I vividly remember the moment I annoucned the launch of BLKessence on my personal Instagram page. Read more>>

Cody Durden | Serial Entrepreneur & Creative Director

“There’s no reward in life without risk” this is one of the quotes I live by. All the people that is considered successful, somehow took a risk in their life. I have taken risks so far that has been favorable for me and my business. At the end of 2019 I started Street Politicians. We were a small team just doing community work before our apparel launched. Beginning of March, I was furloughed from my job. After a couple of weeks I created a plan to take this free time that I now have to focus on Street Politicians LLC. Read more>>

Raheem Amir | Chef/Entrepreneur

Whenever I think about risk I often try to weigh the pros and cons, the outcome of going thru with as well as the outcome of not doing it at all. I feel like being a chef/entrepreneur is taking a risk within itself because your betting on yourself and taking the ultimate sacrifice. Throughout my entrepreneurial journey I’ve taken so many risk the most important one I believe is choosing not to work for someone else and deciding to work for myself. Even though my risk are often planned out as much as possible, taking the risk of not having stability under someone else’s dream was the greasiest choice I’ve made. Read more>>

$weetz | singer/songwriter

Risk taking is something that is very hard to do sometimes. I’d say that taking a risk for pursuing what I love was very hard but I knew that at some point if you don’t risk it then you can’t play the game. Music has always been something that I held close to my heart ever since I was little. Growing up I didn’t have anyone to let me know that making music was something that was possible as a career. I grew up and realized that it was possible. You start from nothing but you can turn that nothing into something.I took the risk of pursuing what I really love for the sake of myself and now I am continuing to build up my career which makes me happy! I would love for people to continue to take risk! Read more>>

Francesca Nobili | Art Director & Stop Motion Artist

12 years ago I became a freelancer to be able to work the way I wanted, and 6 years ago I moved to LA all by myself to be able to live the life I wanted. I am all about taking risks (worthy and well planned) in order to avoid only one risk – the risk to stop loving what I do and who I am. Read more>>

Shai Mackk | Curve Model

With any career changing decisions, there is always an element of risk involved. I decided to quit my job June 2021 after just being promoted and doing really well at the company. It was a great place to work and I had amazing coworkers but I knew I’d get stuck there and forever question “what if?” if I stayed there. There were so many opportunities I was missing because I was working a full time job that wasn’t super schedule flexible. I started having this magnetic pull to take that jump after having this super dope experience on a boat, unexpectedly. Read more>>

Jermaine Alexander | Actor/Director

I have an interesting relationship with RISK. When I first made the decision to pursue acting as a career RISK felt like I was fearful of judgement and of losing something. Knowing people wouldn’t understand how to get a career in entertainment . I didn’t know hot to get a career in entertainment. Like others, becoming a doctor, attorney or business person seemed more attainable. So, I felt I was risking failure, respect from people and embarrassment amongst other things. As time went on and experienced many ups and downs timing became factor. Gods timing. RISK became my friend. Read more>>

Ankita Panda | Animator, Designer, Entrepreneur

As a designer, animator, and recently an entrepreneur, innovation has been an integral part of my academic and professional career – and the best way to create and execute innovative ideas is to take risks. I believe design and business go hand in hand and I have always thought of starting a business to be a creative problem-solving process where the most contemporary solutions and opportunities can be found only through taking risks and trying something new. Read more>>

Maddie Rakosky | Fashion Designer and Business Owner

Starting This Is My Housedress was the biggest professional risk I’ve ever taken. What for years felt so unattainable and scary came together in a few short months after I just decided to go for it. Someone told me the simplest thing, to not think, just do, and everything will have to come together. That bit of advice has led me into entrepreneurship with a gentler idea of risk taking. It’s allowed me to prove to myself that I know more than I think I do, to trust my instinct and work ethic more, and to learn about things in fashion and my own business that I never expected. Playing it safe is certainly comfortable, but taking these risks to watch your business grow is so exciting. Read more>>

Symoné Gates | Founder, Wellness Connoisseur & Military Expat Living in Harlem

If I didn’t take risks, I wouldn’t be in New York, let alone have a company. I was once told that moving to a new city without a job lined up was risky, but at the time no one was considering applicants if they weren’t already in the city. Eventually, I said screw it and moved to NYC with two suitcases, no job and nowhere to live on New Year’s Eve 2015. This motivated me to always follow the path I was most scared of. Since I’m the most over-thinking, micromanager you’ll ever meet, it’s quite a paradox that when faced with a decision, I force myself to always take the riskier path. It’s a mindset that’s always paid off. Read more>>

Cybil Lake | Actor, Writer, Filmmaker

Even though risk taking is scary, it’s a great motivator for me. Pushing myself out of my comfort zone is one of my passions. Risk is a form of being super spontaneous — just going for it. For a lot of my life, I had an alcohol and drug problem so that was very risky but in a negative way. Now I like taking other kinds of risks — pushing myself in exercise, or meditating longer than what feels comfortable. I love taking creative risks — writing even when I don’t feel like it, auditioning for something even if I don’t feel completely prepared, pitching a new film project. Read more>>

Karen Delgado | Creator, Freelancer Coach, and Marketing Consultant

I consider myself a huge risk-taker which has both benefited my life and career, and also gave me some scares along the way. One of my biggest risks was taken back in 2016-2017 when I left my traditional home, marriage, and life behind in California to travel the world solo. Since then I’ve used risk-taking, and strategic moves both physical (moving to new cities and countries every year) and career-wise (job-hopping and freelancing) to propel myself forward. Read more>>

Sebastian Twardosz | Creative Engineer

Ever since I was a kid I always tried to map out my life whether it was picking all my college classes when I was still in high school or charting my career before I even graduated college. Because I’ve always known what I want to do. But of course that’s not how life works. I’ve always had a finish line (for which I am still striving). What I want out of life isn’t something you can earn or buy and I certainly couldn’t afford it having grown up in a working class family. It actually has required my taking huge risks ever since leaving my home state of Michigan. Read more>>

Rohini Chandra | Actor, Singer-Songwriter, & Filmmaker

Risks have played a very important role in my career and personal path! Risks, philosophically speaking, are needed in life when darkness and doubt are the most dominant influences as was the case during this pandemic. Every project I have created and every set I have stepped on has been a risk in hindsight. It started from that question, fear, or doubt as an impulse or catalyst. Read more>>

Maridel Papica | Hair and Makeup Artist

I would not be who I am today if I did not take risks in my career. One of the biggest risks I took was when I left my job in the healthcare field. I previously worked at a Retirement Community for 11 years, and I left to pursue my passion in the beauty industry. It’s scary, but I learned that working with anything you are passionate about always involves risks, especially the kind that results in failure and rejection. I took risks by applying to high end salons and never got hired. But this fueled me to start my own business. Read more>>


MAUREEN KEDES | Actor, writer

Instead of sending me off to school with the usual, “Be good. Listen to your teachers,” my devilish and brilliant father, an outlier, a rebel-thinker, a curious, open-hearted creature, commanded, “Give ’em hell, Maureen!” What he meant was: question everything; delve deeply; never settle for mediocrity; and be fearless on your journey to find your passion, purpose, and happiness. Yes, take risks. My dad, Larry, passed last year, and his message is ringing loud.
I look back on my life and remember friends and family telling me how brave my choices have been. But I have just been following my dad’s “Give ’em hell,” directive. Read more>>

Suzanne Torrison | Artist Manager, Emmrose Music

Unlike most entrepreneurs, I am averse to taking big risks. I waited until I was financially set in life before I had the courage to quit my corporate job and start to work in an entirely new industry, that being the music industry.. I’d always known that I didn’t fit in and loathed working a ‘corporate’ job in the fashion industry, but I fully embrace it, let it destroy me, and then had to pick up the pieces in order to learn that it was the wrong path to take. Read more>>

Jessica Cruz | Hair Stylist and Salon Suite Owner

Risk taking is obviously an important part of entrepreneurship and was something I struggled with for a long time. I always wanted to see the next step and have it set up before letting go of the chapter behind me. It wasn’t until I started on my own spiritual journey and learning about the law of attraction, that I learned the importance of faith and trust. If you do the work, the research, and the preparation to the best of your ability and you come to a change that requires risk, it’s best to try to make it a calculated risk, that is important. But sometimes you really do just have to jump! Read more>>

Vonté Malone | Musician / Podcaster

Taking a risk on something can be scary but some times you just have to step out on faith and believe in your self and your decisions with also a little research behind it, you never know what will happen and for me taking risks has been good and bad in my life/career but way more good and at the end of the day life is all about growing and learning and becoming Wise and taking the knowledge you gained from those experiences and apply them to the new chapters in your life. Read more>>