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.

Kevin Anderson | Designer Craftsman

I’ve always tried to frame risk as something to be acknowledged but not dwelled upon. When I was younger, I was super into skateboarding and mountain biking. One day I brought my mom out to these big jumps my friends and I had built and she told me “Be careful!” My response was, “Don’t say that to me! If I think about crashing I will! ” This has become a philosophy of how I live my life. You need to acknowledge risk, but if you overthink risk it can become paralyzing, and will end in failure. This is especially true as a craftsperson or artist trying to start a successful business. On paper, it will always be a huge risk to start a business rather than keep a “normal” job and work part time on your craft. But if you don’t take that risk you will never find out your full potential. Even once you take the risk of pursuing your craft full time it’s easy to get pigeon holed into making projects that just pay the bills, but don’t satisfy you creatively. Risk is an essential part of pursuing your goals and passion, and I try to use it as a propellor to keep me moving forward on my journey rather than an anchor holding me back. Read more>>

Annette Coleman | Public Art Installation & Engagement

As an artist you take a risk everyday in your art practice. A blank canvas a sculptural idea that has no form–all you do is a risk. Hanging an art exhibit of your work and waiting for the public to show up. Hopeful that you will make enough in sales to cover and exceed your expenses. I’ve taken risks everyday and that’s what fuels the successes that I’ve had. Read more>>

Jessica Tepas | Entrepreneur, Executive, & Writer

I tend to be a bit of a risk taker in many ways. From a very young age, I was taught to push the envelope, try new things, go new places, but always to be kind. Heck, my mom even took me sky diving for my first time on my high school graduation day! If you’re going to start a new business, you cannot be afraid. You need to be willing to adapt, willing to push through fear, and willing to recognize where you’re wrong and stand strong when you know you’re right. It can be very difficult to look fear in the face and say that you’re going to try anyways, but there’s no telling what beauty can be on the other side if you’re not willing to step forward towards change and take that risk. Read more>>

Steve Chapman | Historian, Tour Guide, Writer, Podcaster

Life is nothing but risks–it’s your comfort with this fact that impacts decisions. Crossing the street has risk, driving a car has risk, walking on ice…you get the picture. Some people are risk-averse. Some people are risk junkies. I fall into the category of risk comfortable. I’m not reckless or careless, meaning I won’t take a chance just for the sake of it. But my tolerance for failure or damage or embarrassment is greater than most people I know. Starting each of my businesses, for instance. I heard laughter many times on each new adventure, there were many who wondered if I’d lost my brain and some predicted financial ruin. In my opinion, making peace with the reality that everything in life involves a degree of risk, then carefully thinking through the absolute worse thing that can happen (I get humiliated or humbled or I end up losing a lot of money) can help tame the uncertainty and doubt often associated with risk. For me, this helps propel me forward, making risk an ally not something to be feared. I wouldn’t have achieved anything in life without making risk my friend, and I’d certainly not have been successful in all of my new ventures these last three years. Read more>>

ThatKidCourageous | Beatmaker/Producer/Hip Hop Enthusiast

I know its cliche, but I truly believe that nothing great is accomplished without taking some risks. For myself personally, this year I left my job in the Cannabis industry when the pandemic hit, and then decided to fully commit myself to my music full time. The most difficult part has been facing doubt and resistance every single day, especially with all of the turmoil, uncertainty, and stress that we have all been put through this past year. I feel insanely grateful and lucky to have a strong support team that has helped me to grow and push forward through the struggles. It’s definitely not easy to create the life you’ve always imagined, but I know that it can be done. Read more>>

Maria Navaratne | Arts Educator and Administrator

I think taking risks is so embedded in my whole being that I don’t ever consciously choose the easiest path in my life and career. Moving to the USA from the UK in 2002 was a very briefly calculated risk! I was in my thirties, living in London with my husband and young daughter, with a stressful career managing the Special Needs Provision in a very challenging Elementary School. I needed a reset and I knew I wanted to have another child away from the stresses of London life. We moved to California, staying with family and at every turn, over 18 years, we have always chosen the hardest route, and taken the greatest risk in order to fulfill our dream of making a life in the US. Read more>>

Ross Bernards | Photographer

I used to think I was quite risk-averse. Even when I first quit my job and started pursuing photography full-time I didn’t think I was a risk-taker. Now that I’ve been out on my own for a couple of years I’ve begun to realize that making that jump was a huge risk. I didn’t have any business contacts, I didn’t have a huge portfolio and definitely didn’t have a diverse portfolio. I started looking at some of the other activities I pursue like backpacking, packrafting, and especially canyoneering and realized I am a bit of a risk-taker. I guess for the longest time I didn’t think any of these activities were risky and didn’t think that leaving my full-time job with benefits was a risk because to me anything worth doing isn’t risky at all. The only risk to me is not going for it. Not doing things that make you feel more alive. Not going for your dreams and doing everything you can to build the reality you want for yourself. Everything we do in life has a risk with it, in the next 1000 miles you have a .026% chance of getting in an accident, does that mean you’re not going to drive to the store? What I’ve learned is that when you take that risk, when you take that leap, you realize you can do a lot more than you thought you could. The best way to really unlock your true potential is to take that jump and believe in yourself. Read more>>

Shannon Paige Kenney | Yoga Instructor and Teacher Trainer

When thinking about risk, this question and small business success or failure, I used to be nearly paralyzed. I opened a small yoga studio and store, Om Time, in 2003. I was driven to be a success and worked hard. Sometimes though, hard work cannot surmount the circumstances. After navigating growth and expansion, we were met with the last financial crash, a disaster of an overly expensive build out in a new development that wasn’t at all what was expected, a massive partnership division, a 1000 year flood and a divorce. I met the word ‘failure’ on every front of my life. The circumstances did not just tank the company, it tanked me and my sense of self. I lost all glimmers of self-confidence and I would listen to the voices of criticism (many in my own head), take them in, internalize them and let the blame game make me smaller and smaller until I almost disappeared. Om Time shuttered. I blamed myself and wore the stain of failure as shame in my heart, in my mind and on my sleeve. I nearly left the teaching world of yoga all together and was simply completing existing contracts, before I planned to hide from the world in a blanket fort or cubicle. Read more>>

Courtney Jay Higgins | Writer & Founder of Coincide Yoga & Lifestyle platform

At the beginning of 2020, I wrote out my “risk story” with the help of my life coach. The goal was to look at the times in my life that I took a risk and in return gained a reward. It was amazing to see that throughout my life the times I’ve taken a risk were the most impactful and brought me to amazing people and opportunities. I highly recommend this exercise for anyone feeling the fear of taking a risk or experiencing a lot of change in life. My theory now is that without risk we are not taking the leap into growth. When we take a risk we are telling the universe “I’m ready to grow and I trust that everything will fall into place just the way it is meant to.” Read more>>

Sarah Shuel | Owner, Sonder Music Management

Risk taking plays a huge role in my career and life recently. When I was younger, I definitely tended to avoid risk at all costs, but as I’ve grown as an individual and as a business person, calculated risk taking has become a much larger part of the overall picture. I’m not talking about taking safety risks or risks that could devastate me in any way – but risks that have the possibility of making a big difference in my life and the lives of others. The biggest risk I have taken was in August of 2019, when I decided to leave my full-time corporate job to put all of my energy and time into my own business – Sonder Music Management. It was a huge leap, leaving behind steady income and benefits to pursue my passion. Many people don’t chase their dreams because it’s just too darn scary, but in my heart of hearts, I knew I had to try. That same day, someone close to me told me “You’ll either sink or swim, and it’ll be ok either way.” This is what I have come to live by – as I swim. Even if this risk hadn’t paid off, I have an incredible support system around me that won’t let anything terrible happen if I should sink. Read more>>

Elias Armao | Graphic Designer/Illustrator

I believe that risk taking is central to any success. When you take a risk you have to believe that you can pull it off. That mentality, the “I can do this I can make this work” mentality is pivotal to building your career. As a art college dropout I took a risk when I left school, I took a risk when I decided to quit the coffee shop I was managing and do design full time. Taking risks and living with the fallout, good or bad, has helped me to realize that whatever the situation I can react and adapt and to be honest taking risks is just more fun. You end up in situations you didn’t expect and that keeps life interesting. Read more>>

Kristi Haner & Alex Tiberio | Silversmiths

Gothic Mountain Jewelers would not exist if we hadn’t taken risks! We quit our 9-5 jobs and accepted a flexible paying job in a remote backcountry location. This caretaking job gave us lots of free time to explore hobbies and things that make us happy. Through this exploration came our business. We took another big risk 3 years ago when we purchased land to build our future home and jewelry studio. We began construction this past summer. Taking risks is important, we enjoying challenging ourselves and pushing ourselves to see what we can accomplish and create. Read more>>

Courtney Samuel | Life Changer

I loved working out and saw a lot of people do their own thing and said to myself why not me So I went for it. Read more>>

Cara Nelson | Co-Founder

Risk has been an essential player in our lives both personally and in business. It’s what drives us to be better people and better business owners. It takes grit to take your first big risk, but when you come out on the other side you feel stronger, smarter, more empowered and hungry for more. And that’s what being human is all about. My (Cara) first taste of risk was at twenty, when I went after an internship at a major news network in Washington D.C. I had to go after it and secure it on my own, then figure out how I was going to make it happen. Where would I live? How would I make money? I had never done anything close to that. Being in college, I was fortunate enough to be under the secure wings of my parents who, up until that point, drove most of the roads I took. I got the internship, lived with family near D.C. and found a job to make money. It was a wonderful learning experience and I saw the reward that taking risks gave me. I was hooked. Read more>>

Bonnie Houpt | Music Therapist (MT-BC)

When I entered 2020, one of my words for the year was “bold.” I was ready to take on risk unaware of what lied ahead. Risk is innovation. When the pandemic hit, I needed to reduce the very real risk of the safety of my family and clients while taking the business risk of moving completely online until it was safe to return to in-person. This was a huge risk, and not all of my clients were able to come along for the journey. Because of this business risk though, I created several new services throughout last year that I never would have imagined before. I took the risk and started a podcast, learning as I go. I took a risk and started offering virtual resource fairs and bucket drumming groups, not sure if attendance and sign-ups would come. They did come though, and I am grateful for being able to serve families in the safest way I can as we all navigate this difficult season. I learned in 2020 to embrace risk, knowing I can learn from “failures” and that the greatest risk of all may be never trying. Read more>>

Rainbow Milita | Immersive Production & Full Service Entertainment Company

We are no strangers to taking risks as performers, producers, and artists. Performance art is all about leaning into expression, vulnerability, and sometimes even physical feats that defy gravity! The first risk you take is putting yourself out there, and the second is believing that you can make a lifestyle as an alternative as a theater a daily reality! This industry often requires us to blaze our own trail and to make opportunities where there are none. Immersive Circus shows take a great deal of creativity and problem solving, especially in 2020. Last year our industry went completely dark and our team had to find ways to make shows possible while keeping our audiences safe. Read more>>

Jennifer Roubal | Wedding Planner

Taking risks is my motto. Looking back I’ve probably been a risk taker my entire life without even knowing it. I’ve always been a ‘free-spirit’ type of woman. I remember taking risks starting at the age of 23. I followed my dreams and moved to Los Angeles. I was young, driven and willing to take any risk that came my way. I found my passion for Events and developed my career in the six years of living in Los Angeles. I moved to Denver at the age of 29. I took a risk in leaving my job and finding my true career path with Anna Rae Events. I truly believe the risks I’ve taken in life has led me on this wonderful journey and has put me where I’m meant to be today. Read more>>

Ashley Scobey | Owner | Hazel Moon Pottery

My relationship with risk has been such an evolution. Personality-wise, I’m incredibly risk-averse… and yet, the reality of the entrepreneur is that everything you’re dreaming of is on the other side of some pretty hefty risk. My husband and I have been small business owners for the past 12 years, so we’ve taken a lot of risks to start and grow those businesses. Some of the risks have led to huge failures (and all of the learning that comes with that). Other risks have led to beautiful successes and the ability to live the kind of life we really believe in. Read more>>

Judith Briles | The Book Shepherd and Author Advocate

Without taking risks, stagnation occurs. Curiosity is stifled. Growth slows and may reverse. Throughout my years, I’ve taken positions to speak up and out; to engage strategies that went against the grain of acceptable positions in starting my first business, to my publishing as well as speaking on the platform that took me to 50 states and over 20 countries. Read more>>

Rashad Randolph | Creative Director

Taking a risk to achieve a goal requires a lot of courage to face the fear of uncertainty. No matter the outcome, positive or negative, we grow through the process and become more resilient and confident. Read more>>

Melinda Carbajal | Owner Simply Pizza

Just over a year ago in October of 2019 our family took a big jump and became the owners of Simply Pizza Truck. I left a career in community engagement, my husband left his career in water osmosis, my sister cut down her private Dr. practice and her husband began his exit strategy. We had never owned our own business, never ran a kitchen (I mean I managed Wendy’s in college), and never worked a food truck! We are parents of 5 kids each and we wanted our 10 littles to see us work hard and reap big benefits. We wanted to build a empire with our family values. Risk is everything right now. It’s working, despite the hiccups of covid. We could have continued to practice psychology or work for the government and live an average life, but that wasn’t enough. Without risk we would have never made these memories and the family album could have never been so robust. Read more>>

Kelly Fenson-Hood & Kieran Murphy | Red Branch Bakery | Loveland, CO | A Family-Owned, Home- Based Baking Enterprise With a Mission To Deliver Happiness Through Simple, Old-World Baking Techniques

We started our bakery without major funding, which forced us to take very strategic, calculated risks… and so far it’s paid off in spades. A great example was our decision to start the bakery under the Colorado Cottage Foods Act (, rather than opening a retail location. Under Cottage Foods we were able to bake out of our home kitchen and test our business model without making a huge investment. We did it for a year and quickly hit the ceiling to produce enough baked goods to meet the demand for our products. In the beginning of our second year (January 2020), we turned a 700 square-foot building, conveniently located in our backyard, into a large kitchen. We were able to scale up our operation at a minimal cost, while continuing to avoid the financial risk of operating a brick and mortar store. That decision quickly paid off when COVID hit a few months later. We were able to quickly and smoothly pivot our business model from being a “pop-up bakery,” selling baked goods at local breweries (similar to a food-truck), to online ordering with curbside pickup. Read more>>