How do you think about risk? What role has taking risks played in your life/career? Check out responses from hidden gems from our community below.

Louise Canton | Portrait Photographer

I’ve had a ‘home is where you hang your hat’ mindset for a while now and have adapted quickly to where I live which has brought a lot to my photography. Read more>>

Douglas Smith | Adventurer & Entrepreneur

Risk is a necessity of life. I view risk as a trade off and has a ratio, the more risk the more reward, low risk, small reward. So if you take bigger risks, you’re going to end up with a bigger reward than most would obtain, the key to it is finding that proper balance of that ratio. I’ve learned over the last 20-25 years that proper planning, research and calculated judgement, mitigates a good portion of a high risk scenario, which in turn leads to higher rewards. Doing your homework in life before just jumping in, gives you a better chance of success and not failure. I like to climb mountains and there’s a fair amount of risk in the process of doing so, but I’ll always do my homework before a large climb with previous trip reports, keeping in the best physical shape as possible and planning/executing the climb in the best light. The reward in the end is the same if you just wing-it or actually systematically plan out for success. The same holds true in anything we do in life. Read more>>

Duke Dufresne | Business Owner & Entrepreneur

I believe that risk-taking is part of life and business, but that doesn’t imply that reckless risk-taking is acceptable. I always consider the upside and downside of any risk that I take, always ensuring that the downside (worst case) is acceptable to me. If I can’t like with the worst case, then I either find a way to mitigate it, or I don’t proceed. Read more>>

John Bertino | Entrepreneur & Marketer

When it comes to entrepreneurship, a tolerance for risk and the ability to take measured risk is critical. It’s obvious, even cliche to say that risk must be calculated. But it’s the degree to which we commit to making good calculations that literally predicts our chances of success. The more complex a decision, the more we must be committed to diligence. And the more diligence you must do, the more it pays to be committed to continuous learning. Ironically, whereas half of us are perhaps prone to risk taking without proper diligence, the other half finds itself on the side of overthinking and regularly grappling paralysis by analysis. At some point, entrepreneurs need to be willing to take leaps of faith without knowing for sure that your risks will pay off. This is where it becomes advantageous to develop a tolerance for failure. Read more>>

Melissa Grove | Founder & President

I often say “I am not a risk taker” yet reflecting on my career I believe I have taken risks comfortably and with extensive research. I would say in the nonprofit world there is a balance of both. When you create projects to support the community it’s mandatory to evaluate risks but at the same time you are aware your mission is to fill an urgent hole that is needed in the community. As a leader of leaders who choose to empower through music education, you are taking risks and asking people to be vulnerable, trust and learn otherwise the music may not feel authentic. It’s a beautiful process yet requires risk taking. I often ask myself three things when I start any project: 1) Is it safe? 2) Does it empower youth? 3) How much is it going to cost? After I have answered those questions I coordinate and collaborate with teams that are comfortable with risk taking and inspire impact. Read more>>

Ashlee Hayden | Maternity, Newborn and Child Photographer

How do I think about risk? Well, risk is in every endeavor and career decision. It is always on my mind. When I began my career, I was a single mother of 2 working as a waitress and going to school full time. There was a lot of risk personally, professionally, and financially that I had to think about. At times, it could feel overwhelming, but I had to turn that uncertainty and fear into motivation and determination. Even more recently, I decided to open my first commercial studio space in the spring of 2019. I had been working out of an extra room in my house for a few years and was starting to outgrow it. I had to make that decision to leave the comfort of my home, and move to a new space that added so much more uncertainty. But my determination refuses to let me fail, so my trust in myself outweighs the risk. Read more>>

Jeremy LaBahn | Business Owner

I think there is some level of risk in most of our day to day decisions, but we don’t really stop to think about it. There is risk in getting in your car and driving somewhere, being a large public place, picking up food from a street vendor etc. All of these scenarios welcome some level of risk into our lives. When we think of starting a business, to most people that is the ultimate risk. When I’m evaluating the potential for risk in my life, whether it’s in regard to starting a new venture or getting on an airplane, I always think “What is the absolute worst thing that can happen?” If I can find peace with that outcome, then I will take the risk. Read more>>

John DeBello | Filmmaker

Every business enterprise begins with an element of risk. With rare exceptions, success actually increases risk. My first business began in college with unlimited optimism and severely limited capital. The venture was successful, but required constant pivoting as the market quite naturally shifted. It’s often said that failure is the best teacher. Personally, I believe that experience (of all kinds) is the best arbiter of risk. The other key factor is personality. Some people jump out of airplanes, others are afraid to fly. Not being a huge fan of Glorious Failure, I take the leap with a safety chute. When I was 24, I directed and co-produced a ‘risky’ independent movie called Attack of the Killer Tomatoes. It was purposefully designed to zig where other films zagged, to cut through the clutter. Read more>>

Josh Trent | CEO, Wellness Force Media & Host of Wellness Force Podcast

I think about risk as a fuel source and stimulus for growth; if I’m not risking something every day then essentially I’m not growing. We’ve all heard the social media meme “on the other side of discomfort is your dreams” and I have to say this plays out to be true quite a bit. When I look at the largest mistakes I ever made in my 20’s it was when I was afraid of risk and I chose the path of perceived “safety” by taking the well beaten path – but let’s be honest, there is no such thing as safety – especially in today’s fast-paced and ever-changing career landscape. I take risks in my career, podcasts, friendships, relationship, and every way that I can because it is how I sharpen my sword of intuition that allows me to actually live a life of freedom, and ultimately to live my life well. Read more>>

Zachary Hollander | Photographer & Videographer

I think risk taking is a hard subject. I think thoughtless risk taking is the quickest way to end up in a bad situation. I believe calculated risk taking is 100% worth it. There are lessons i’ve learned growing up where every time I took a risk thoughtlessly I always ended up injured. If I took 5 minutes or more I came out wiser and more prepared and moor times than not okay. In business I ask advice before I make any major decisions, I like to gauge different perspectives and thoughts and weigh each one up to try and make the most educated decision that I can. Read more>>

Brook Larios | Co-Founder, CEO & Food and Lifestyle Writer

Jumping into public relations from journalism was a mild risk, but the greater was deciding to go all in while still struggling with self-loathing over transitioning to what was commonly referred to as “the dark side”. When I abandoned that silly narrative by embracing my role in helping clients I believe in, I proudly and relentlessly became personally invested in the businesses I served. Each time I shifted into a new career position, I was taking a risk: in one case, the role paid less but would stretch me and grow me further. In another, the position was above my expertise, but I was gritty and successfully grew within it. Wise risk taking is so integral to what we do that we declare it as Hoyle right on our website: we’ve proven that calculated risks reap big rewards for our clients. Many of them expect it. They recognize they’re getting something special, creative, exclusively for them. It lights us all up. Read more>>

James Darby | President & CEO

Risk has always played a factor in my life. When I was `13 years old and my friends decided to surf a spot in Peru called “Villa” I was petrified. The spot had a reputation for being aggressive. I sat at the shore preparing to head out with my friends and decided I wasn’t ready for it, I left and I was called all sorts of things for bailing. At the same time, I was competing in BMX every Saturday. The first jump was so high and long that I would not jump that first jump but will always end 2nd or 3rd place regardless. Years later I classified for the BMX World championship and I have traveled the world surfing. Risk is a combination of experiences that makes us confident enough to jump into the unknown. It’s also exciting and scary at the same time. Sometimes you fail but the end goal is to succeed. I have risked a lot, maybe everything this year 2020, but I am confident I’ll make the jump. Regardless of the billion obstacles, I can see clearly the end result. Read more>>

Laura Wolfe | Realtor

I think about the idea that it’s better to try and learn from your mistakes than wonder what if. Also that failure isn’t to be feared because you either win or learn. You never know it could be great! Read more>>

Jeff Nishinaka | Paper Sculptor Artist

I’ve always believed that taking risks in my life/career is totally necessary and an important part of the journey to becoming a better artist. To begin with choosing to become an artist is a huge risk. There are no guarantees of success not to mention a steady income and a normal life… whatever normal is. But if you don’t take the risk then you’ll never know what could have been. Some of the best things in my life have happened because I took the risk. It’s easy to stay within the limits of your comfort zone, but then you never get the opportunity to experience something new and different and potentially hugely rewarding. Because of my belief in taking risks I’ve been able to travel the world and met some of the most amazing people. My life/career would not be what it is today if not for taking risks every chance I had. Read more>>

Matt Carney | Artist, Non-Profit Executive & Arts Advocate

I’ve never been comfortable being comfortable. Riding the edge of the cusp between comfort and resistance positions you to build resilience and keep the learning process at the forefront of your experience. The experience of COVID19 puts this practice into ‘normal’ operations. Businesses literally cannot do what they have always done. Risk taking now is inspiring innovation in all aspects from planning to implementation. Risk to me is like following spontaneity and serendipitous moments. At times it may be difficult to trust, but awareness of those moment of opportunity lead you to places you couldn’t have imagined. Read more>>