In our experience, most folks, including ourselves don’t have enough of an understanding of risk and the role it plays in our lives and careers and so we have made a concerted effort as a team to have conversations about risk with our interviewees. We’ve shared some highlights below.

Maria Yuan | Founding Executive Director, IssueVoter

I have asked myself, “If I don’t do this, would I regret it?” And if the answer is “yes”, then I do it! I’ve made several big decisions that way, including launching IssueVoter. Read more>>

Sydney Ilg-Malone | Marketing Director at 11th Avenue Hostel

I am a big believer in following peace. Anything worth having, professionally or personally, involves risk. Nothing given, nothing gained. To achieve growth, to reach our professional goals, and to shape our businesses with the times takes challenge and great risk. For me, I always think about risk in theoretical and monetary terms. For example, we undertook a major renovation this year, and our first question was: “how will this impact our guests” and our second was, “how will this impact the bottom line?” We had to understand the great financial and experiential risk and reward before approaching the practical application. But we followed the peace: the numbers added up, the gut feelings added up, so we went for it. I think that applies to all areas of life. Read more>>

Miss Rae | Artist, Model, Comedian & Writer

When it comes to risk taking, I think people immediately correlate risk with reward as a reflex that stems from a collective societal standard. While I find value in this old adage, the risks I have endured are much more complex than a simple juxtaposition such as this. In my experience, risks have been quite costly even when they are simultaneously accompanied with rewards. For example, I have found that even my failures have perpetuated catalysts that inevitably stemmed into my success. Not many people know this about me but failure is something I’m very familiar with. I am technically a high school dropout, as well as a college dropout. However, neither of these (societal) ‘failures’ have hindered my ability to be successful as a business woman. Read more>>

Everett Jesse | Founder – Fossil Outdoor Inc.

My entire career had been taking big risks and failing. Failing in business has taught me that hitting rock bottom is never as bad as you believe it will be as long as you persevere and continue on. I have ridden the downward escalator of failing start-ups 4 times, it has resulted in incredible amounts of loss, bankruptcy, pain, and embarrassment. Four times I have had to build myself back up from zero. In the spring of 2019, I assessed the risk of bringing a product to market which solved a pain-point but is extremely niche. Having been through those failures I decided to risk my savings and my ego on a 5th start-up. The past failures have acted as tuition though, and it is because of them I am successful so far in this business. I am grateful for my failure because they have made me who I am today. Read more>>

Allison Jemeson | Floral Artist & Owner

Normally, I am a fairly risk-averse person. But I will take risks when I have the opportunity to plan them out… so I guess I take calculated risks, if they make sense to me. If you’d have told me five years ago that I would start my own business in the middle of a global pandemic, I would have laughed in your face though. I still can’t believe I did that. Leaving a successful nursing career and starting an unpredictable solo venture has really been the most significant risk I’ve ever taken… but I’m learning that the bigger the risk, the greater the reward. So cliché, right? Read more>>

Thomas Hernandez | Entrepreneur, Community Developer & Non-Profit Founder

I’ve live my life with the capacity take risks at all cost in which has got my lived experience to my upbringing very challenging to the fact I almost lost it many times over. Yet still today after making a complete 180 degree change for the better that same no fear value I’ve lived all my life has helped me overcome life’s challenges and my success today in business. Read more>>

Miles Moran | Co-Founder

Life is always risky, how do we know? Because no one gets out alive! That is a simple but powerful statement when you unpack it. I personally have found, if you never jump you will never know if you can fly. But the more jumps you take, the flight becomes more steady, less scary, and you can navigate that risk factor with the confidence knowing that you have been there before. Sometimes you have to take two steps or even five steps backwards to go forwards in the pursuit of what you want in life. I have left jobs without having anything lined up because the fear of feeling stuck outweighed the risk of the ever popular “what if” scenarios that get played out in our minds. Read more>>

Carlos Michael Finn | Artist

For me risks… are powered by faith & intuition. With the two an artist then carves his/her own path. And a new journey begins by being bold and taking a chance! Nothing ventured nothing gained. Sometimes a little risk can lead to great love or success! Read more>>

Diana Ralston | Executive Director

I believe taking risks, at least calculated risks, not only help stretch you beyond your comfort zone, they have the power to propel you to the next level. I have found this to be just as true with personal relationships and inner growth, as it has been with my professional trajectory. There is something invigorating and exciting about taking the leap and not knowing if you’ll land on solid ground. From starting a restaurant with zero experience, to moving away from the safety and security of my home of 20 years, to getting divorced and starting Can’d Aid, none would have been possible if I hadn’t been willing to take a risk. The confidence that comes from successful risk-taking fuels my drive and determination. Conversely, failed risks provide valuable lessons, not the least of which is humility. Read more>>

Christine Brown | Virtual Assistant & Coach

Without risk, I wouldn’t have a successful Virtual Assistant business. If you had told me five years ago that I would be an entrepreneur with my own business, I absolutely would have laughed at you. I figured I would spend years in the classroom, maybe even stay home with our children while they were young, but never thought of myself as a business owner. In the months after our youngest child was born, I was looking for a part time job opportunity, but nothing I came across or tried was quite the right fit. A friend of mine recommended that I explore VA work. I knew it would be risky. I knew there was a chance it wouldn’t work out for us. So, I decided that if I made the leap, I would have to stand firm with my decision. Read more>>

Jessa Trefethen | Hair Stylist & Salon Owner

Taking risks is a huge part of any successful career. While some may be calculated risks, I believe that stepping into the unknown can bring more rewards. Joining the beauty industry was a risk. I had never considered myself very artistic or creative and I was nervous that I wouldn’t “fit in”. Starting my career in a brand new salon without a clientele I would consider a huge risk. The first couple of years of business are the most intense. The fear of wondering if the salon would be sustainable, what my future looked like within this building, and if I had made the right choice. Now as a co-owner of this salon, I can absolutely confirm it was the right choice! Becoming a traveling stylist was a dream that became a risk as well. I have had the honor of working backstage at NYFW and DFW while also shooting editorial work with the Beauty Underground in Denver as well as Madrid. Read more>>

Raine Roberts | Filmmaker, Photographer & Editor

To me, taking risks are necessary for forward movement. If you don’t take the risk you become stagnant. Though, I’m not a huge fan of impulsive risk taking, that to me has never turned out well. There’s a threshold for me to allow for a “risky maneuver”, but I have to be–in a sense–prepared. Prepared not in the conventional sense of the word, where one does everything possible to predict outcomes and prep for those hypothetical consequences, it’s more of a preparedness of change–something you may not even realize you’re ready for, but you are. For me, I know when I’m feeling stuck or stagnant, when my routine becomes too comfortable. I never want to be too comfortable, that indicates to me that I have completed a certain amount of growth and have adapted to a certain environment, I need a shake up. Read more>>

Abigail Kreuser | Gallery Owner & Curator

I think starting your own business is a risk and each step to growing your business is another risk. However, if you are following your dream, than those risks are worth taking. To be able to wake up each morning and be excited to be doing what you’re doing makes it all worth it. Read more>>

Murphy Weibel | Wedding and Lifestyle Photographer

Before going full time with photography, I worked for a few food companies doing their marketing and community outreach. Even though I liked a few of those jobs, I hated the 9-5 structure. Being stuck in the same cubicle doing the same thing every day was a little maddening to think about for the next, however many years. When I graduated college, I thought that was it, that is what everyone did and you just suffer through for the rest of your life. As a Christian, I truly believed there was more of a calling for me and my life to not be passionate about my life or job. At the time, I had just gotten married, started a new job, and we had a sizable amount of student loan debt hanging over us. The idea of me quitting my secure job to pursue my dream was a colossal jump, the biggest I’ve ever made by far. Read more>>

Sydney Golden | Entrepreneur, Event Marketer & Fitness Fanatic

Taking risks are the only way to grow in life. If you aren’t willing to take any risks, then you aren’t willing to grow and you are guaranteed to stay exactly where you are in life. What you need to know and truly believe, is there’s no such thing as failure. When you are willing to take a risk you are telling the universe you are ready to grow, whatever the outcome is, it’s pushing you towards the next level. Even if you deem the outcome as a failure, it’s not, it’s a lesson. The only requirement is that you learn from every type of experience and that’s what propels you forward. The only failure is not trying at all. The bigger the risk, the bigger the reward no matter what the outcome is. Read more>>

Jonathan McAfee | Expressive Figurative Painter

In order to grow as an artist I believe that it’s important to take risks regularly. That doesn’t mean that I am always making high-risk decisions, but I do feel that exploring areas outside of one’s comfort zone is important. With our rapidly growing social media landscape, being an artist today feels more like a popularity contest than anything else. I am not as interested in being the most popular as much as I am striving to be the best that I can be. And in order to improve I explore new avenues with my paintings and subject matter. Read more>>

Glenn Sawyer | Music Producer/Owner of The Spot Studios

Risk has played a large role in my life and career. I think growth requires taking risks but I’m a big advocate of knowing what you’re getting into and making sure that the risks you take are calculated ones. When I started The Spot Studios I had never managed a business and it was a serious leap of faith on my part. I had to find financing to get the business off the ground, and if I had failed I would have been in a financial hole for the foreseeable future. At the time this was a fairly terrifying idea but I knew that what I ultimately wanted lay on the other side of that risk. I believed in what I was doing though and when I found myself stressed about making everything work I would use that as motivation to work harder. As the years have passed risk has remained a constant but my ability to recognize it and prepare for it has improved. This year has been a great example of this. Read more>>

Kaitlin Reagan | Motivational speaker, TikToker, Young Entrepreneur, Influencer

Risk taking changed my life. Here is an example. When I was in my senior year of high school, I wanted to go to college in New York City for acting. I was currently already attending a high school in Manhattan for acting. However, due to my poor score on the SAT, I got rejected from every single college I ever dreamt of. I was traumatized. I felt like I would never be happy. I watched all my friends get accepted into every single college they ever wanted to go to. I felt so alone, I felt like such a loser. There was ONE college that I did get accepted into though. It was a college that I applied to just to have back up, I did NOT want to go to college in Florida. To be honest, I don’t even know why I applied. The idea of going far away from home freaked me out. I knew no one that lived there, it was so far away from NY, and I didn’t know if I would like it. Read more>>

Candace Dickard | Cake Designer

Risk, the definition of owning a small business. I always ask myself, if I jump off this cliff, is the fall worth the risk? There are so many things in life that we would never experience without risk! So many opportunities come from risk being taken and whether the outcome positive or negative, we have to take them on with full force. My career and business wouldn’t exist without take a small step into risk! Success can ultimately only come from great risk! Read more>>

Asha Bee | Actress | Model | Entrepreneur | Mentor

Being an entrepreneur is all about taking risks and I take them everyday. Whether it’s with a new financial investment, another business endeavor or when I’m on set. In my opinion, it makes life much more exciting and worth living. I’d have to say the riskiest of my adventures usually fall within acting due to the emotional and physical vulnerability I have to subject myself to. There are times where I have to resurface some of the most heartbreaking moments of my life because the scene requires it. Many people don’t realize the strains that come with this line of work. Imagine every day you go to work you have to be someone else mentally, emotionally, physically, spiritually, etc. That’s what working actors do. Whether we’re auditioning, in class or on set. Read more>>

Meagan Friel | CEO & Stylist

That’s the thing about risk, you just do it. For me, there wasn’t much thought process about opening up my own business. In some people’s eyes, that’s not a smart move. I remember sitting in my car crying during my lunch break one day, and that’s when I knew something had to change. My biggest challenge was figuring out, “What am I going to do next with my life?” I had the pleasure of working at a corporate chain as an Elite stylist for almost 6 years. I was hungry for more. I wanted more freedom and I wanted to do something kind of scary to see if I could survive. I chose to open up my business, Wild Heart Salon, because I needed to challenge myself. I needed to push myself to see the other side. Read more>>

Tiana Mile | Psychotherapist & Mindfulness Educator

Taking risks, or engaging with what life presents, has required me to get comfortable with being uncomfortable. Truly listening and acting on what is calling us requires mindfulness, deep courage, and a faith that failure does not really exist. We may be choosing to walk away from what is mainstream, sensible, or comfortable towards what is scary, unknown, and vulnerable. There are big and little risks, but all can be opportunities for deep transformation depending on our mindset. We will need to learn to embrace fear, versus avoiding it, and move towards curiosity, purpose, and truth. By loosening our grip on a certain outcome or what we believe the result says about us, we can learn to see life more as an adventure. There may be pain or suffering along the way. Read more>>

P.J. Parmar | Refugee Doctor

Doing refugee medicine as a private business has brought many risks, including: taxes, financial audits, fluctuating Medicaid reimbursements, changes in numbers of refugees, legal exposures, medical board complaints, neighborhood crime, and police violence. Serving the refugees makes it all worth it. Business would not be productive if we weren’t comfortable with risk. Read more>>

Trice McNeil | Owner

Risk are highly needed mountains. They catapult you into a new perspective of ideas and direction. At first risk seemed terrifying and worthless, because of that main thought process of wondering what your business can and cannot endure. As a business manger and owner, I understand the key point or advantage gained from stepping out of your comfort zone. It has really transformed me into being more open minded and confident in the choices that I make and it has also propelled my business to a greater height. Read more>>

Nate “Nemo” Niemerowicz | Photographer & Creative Director

I love risk. Hell, it’s my favorite board game. In all seriousness though, I think I need risk to fully believe in a decision. It’s got to have a very real positive and negative outcome, a potential consequence, a real cost to its existence. For me, if there isn’t some level of risk, it won’t trigger the best parts of creativity, the process will lack depth. For instance, growing a business during a global pandemic – that’s a risk. That risk created a series of opportunities, and engaged my process as a creative. So as much as it’s about the risk, it’s also about the individual, how they navigate the risks, and pursue outcomes. The same risk looks different for me than it does for someone else. Read more>>