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.

Lindsay Droter | Artist & Small Business Owner

I’ve been told many times that I’m a risk-taker. But I’ve never seen myself as one. Risk means exposing yourself to danger or harm. And I love safety. Masks? Yes please. Seat belts? Definitely. Packing enough water for a hike? Arguably, too much. But when it comes to my life and career, I have a different take. My husband (then boyfriend) and I moved to Colorado in 2015 with one car, no house, no jobs, and barely any money just because we wanted to be close to the mountains. Read more>>

Will Fenwick | Photographer, Videographer, Adventurer

Risk is the ultimate gamble of destiny and happiness, a necessary gamble to discovering our purpose in life. I personally see risk from the adrenaline junkie’s perspective because the only real risk is death, and not exactly in its most literal form. Sometimes we need to face death in a metaphorical sense to step away from our pride or ego and find out who we really are and what we really want. At the end of the day if our liveliness isn’t part of the equation then we have every reason to jump. Losing is always a possibility but even our losses carry lessons that will prepare us. Read more>>

Eva Nicolait | Painter

Like other activities where skill must be transformed into intuition, painting reflects our embedded reactions to success, failure, frustration, and ease. Evolving with painting has required that I lose my inhibitions about mistakes and failure. When I come to an impasse, I’ve had to learn that I’m simply stuck for awhile and either walk away for a bit, do something else so ideas are allowed to filter through unbidden, or just wade in and mess around with it and deal with what happens. The wonderful thing about painting is the process of getting there, the discoveries that result from problem-solving with a mixture of expertise and abandon. Read more>>

Shawn Wall | Executive Director & Philanthropist

Being from Colorado, I took advantage of an exhilarating sport called rock climbing while growing up, which inherently has a lot of risks due to the nature of the sport. Risks are something that you learn to assess, accept and progress with. You will not become a better climber unless you’re willing to accept and take risks. I feel the same applies in most areas of life. I would not be where I am now in life, both personally and professionally, if I hadn’t taken some significant risks. Read more>>

Juliet Root | Transformation Coaching & Co-Founder of My Richual

Someone asked me recently “Do you initiate leaving a relationship or situation first or do you wait for the other person or situation to end it?” My answer is that I have always been the one to initiate walking away from something, even when it is the hardest thing I have had to do. There’s a huge risk in leaving something to start a new. It feels scary and uncertain when you move away from the familiar and walk towards the unknown. But in my experience the only way I have achieved exponential growth and success is through this process. Read more>>

Jenna Frederick | Content Creator

Putting yourself and your work out there for the world to see can be truly terrifying. However, it’s a risk that everyone working in creative industry is forced to take every single day. In my personal life, especially when I was younger, I was never a big risk taker. I would always be the kind of person to choose the safer option, primarily due to fear of the repercussions. By the time I began working in the creative field, this low risk mind set quickly became a hindrance. I was afraid to put my work out there for people because I was terrified what they might think or say. After so long of holding myself back, Read more>>

Mercedes Peña | Basket & Berries Luxury Picnic Co.

Taking risks is absolutely necessary to grow! You have to take risks and learn from the experience in order to progress. For us, moving to Colorado was a risk as we did not know anyone and were not familiar with the area. If we would have never made the leap, we would not have started our amazing business and helped so many people make incredible memories. Read more>>

Kimberly Gibson | Principal Designer, Interior Design by Kimberly, LLC

Growing up, I was always a bit risk adverse and found comfort in taking the safe route, following the rules, and basing decisions on what I knew to be true. However, it was also always my ultimate goal to work for myself and own my own interior design firm. While the steps to get there weren’t always clear while I was in college, it still remained the overall goal to achieve. After design school, I was lucky enough to hone the skills I had learned in school and put them into use while overseeing visual operations at Anthropologie for nearly a decade, and later at Crate & Barrel for about three years. Read more>>

Kayla Fassio | Holistic Health & Mindset Coach

I love risks! I think they are essentially for not only growing your business, but as a person. The risks I’ve taken have only furthered my career even if it didn’t look like it at the time. I moved to Los Angeles from Oklahoma City to pursue my fitness career and had amazing opportunities. I’ve put myself out there and have been vulnerable with personal traumas in hopes to be an inspiration to others, which is risky and scary. And now, from that, I’ve been able to shift my brand in a much larger capacity. Risk is everything and it vitally important to grow as a brand. Read more>>

Peyton Glynn | Music Artist

Taking risks have always played a huge role in getting me to where I’m at today especially as a music artist. Looking back and realizing how different my life would be now if I never took a leap of faith is crazy to think about. I never would have imagined 10 years ago that I would travel and live in 6 different states in a span of 6 years , crafting and seasoning my musical abilities and ultimately end up in Denver. I never had much opportunity where I lived and I realized if I never took a chance on becoming the person I wanted to be then I would’ve always wondered the outcome. I didn’t want to end up in the “trap” of being a hometown hero. Safe to say If you don’t take risks , what’s the point of living Read more>>

Alexis Saghie | Entrepreneur

If you know me, you might know I am fearlessly spontaneous and often act in accordance with my desire to challenge myself and to take the risk…to see what could come of “it.” I’m a firm believer that a way to finding purpose comes through opportunities we encounter that enable us to take risks that push us and challenge us outside of our comfort. Especially after COVID-19 and being bottled up, I challenge myself to say “yes” to opportunities that involve risk. I think there is something beautiful in that: to willingly be able to take a risk with the purpose of knowing something greater is in store. Read more>>

Molly Adkins | Sound Healer, Yoga Instructor, Empowerment Coach

I took a huge risk in my career recently. I had been teaching high school in Indiana for the past 19 years, and in Japan for 11 years before that. Last summer I had the rug pulled out from underneath my secure job. I had receive a year leave from teaching to be able to manage my sister’s wellness business in Indianapolis while she was gone for a year. As it turned out, she did not take her year off, which left me without a job and income for the year. Read more>>

Kat Knott | Co-founder, Snowmobiler, Rooster

As a snowmobile club, most of us are inherent risk-takers. Red Cliff Roosters was borne of our passion for snowmobiling. The risks involved in the sport compared to the rewards in our lives; are worth it. For us— there’s just nothing like seeing the joy of someone new to the sport smiling from ear to ear, having the time of their life, falling in love with snowmobiling. Read more>>

Rob Lujan | Photographer

“With great risk comes great reward.” Thomas Jefferson once famously stated. Four years ago I was stuck in a dead end retail job unhappy and very stagnant. With company restructure I came to fork in my road, I was faced with having to make a choice in my life that could change my future. With financial responsibility weighing heavy on my decision the job security seemed to make the most sense. At a time when employment was limited I would have to rely on income from small photo gigs until I was able to secure employment. Read more>>

Dr. Ginger Wolfe DC, DABCI | Functional Medicine Practitioner

When it comes to owning your own business, risk taking is just part of the equation. It’s jumping off the cliff for your passion. You just have to commit, buckle up and make it happen! I’ve started four practices in my 21 years of practice and they have all been successful. Sometimes that means mentally thinking of where you are going, not where you are at. Initially, some weeks are good and some weeks are bad but consistency always pays off. For me, it’s offering consistent quality care and a consistent experience as a patient. And above all, I believe in what I do. Read more>>

Christopher Henry Young | Broadway Actor & Arts Educator/Performance Coach

Overall, taking risks has gotten a bad rep as a result of how often we hear about the negative impacts of risks taking. I’ve found a more productive way to view risk-taking. Part one has been getting to understand me professionally. Figuring out what I need to make the moves I’d like to make in my career. Part two has been creating a structure for coping with whatever the outcomes of my risk-taking may be. It becomes less frightening to take risks when I know I have a way to cope with whatever the outcomes are. Read more>>

Sabrina Stiles | artist

You won’t get anywhere if you don’t take risks as an artist. Personally I stopped listening to the advise of others when it comes to painting quite some time ago. I’ve learned that if the work pleases me it will probably please others. As a painter the possibilities are endless and well, that suits me. I love to play and experiment. That’s not to say I don’t adhere to tried and true principles of my craft but once those have been dealt with it’s time to push the envelope. With so many brilliant artists out there, it’s important to find your own voice if you want to get any sort of recognition. Of course I’d continue to follow this path whether I got any recognition or not. Read more>>

Emily Christopher | Musician & Marketing Director

I believe risk is essential to life and following your dreams. We never step out into a dream without having to take some sort of risk. It could be risking time, energy, money, reputation, etc. but there is always something that we are putting on the line. Without taking necessary risks we would never get to the next level. We have to be willing to put something on the line. It’s terrifying. It’s thrilling. It has to be done. Many times throughout my life and career I’ve had to take a risk of some kind. The benefits may not have been immediate, but oh how they were worth it! I can recall having a discussion with my mentor years ago. Read more>>

Brooke Hill | Owner of Brook E Boutique

My initial response to being a Risk Taker would be no, but looking at my life I know I have it in me. I was very much a risk taker when I was in my early 20’s. I wanted to try and experience everything. After having kids at 28 and 30, my risk taking days were over, or so I thought. When I became a mom, my whole world became about taking care of these 2 precious little boys. However sometimes in life, no matter the risk, you know that you are meant to do something. 5 years ago I became a Living Kidney Donor. Read more>>

Coleen Orr | Custom Hat Maker

When I look back… Taking risks has played a big piece in the pie of my life and career. I didn’t analyze decisions to the point of extinction. Instead, I said yes to the things that I was passionate about, and tried my best. I truly believe that when things are meant to be – they will be! When setting out to start my second career, I felt blessed to locate the vintage hat manufacturing equipment on a 2300 mile road trip from Alberta to Corpus Christi, Texas. I had no clue how to use this equipment, but was excited for the opportunity to try. Read more>>

Greg Atkins | Atkins Enterprises Medium Duty Hauling

It is impossible to know the exact outcome of a decision when it comes to risk taking but, it is critical in business for growth and success to take risks. Risky business decisions need to be thoughtful , not reckless . What has worked well for me is a planning rule of thumb that I learned during my career in the Army. I ask myself… what is the goal and is it achievable? Then I consider: -Best case scenario -Worse Case Scenario -Probable case scenario Read more>>

Steven Schultheis | Owner of Steve’s Goods

CBD products are not as risky as they used to be but things can still get sticky. Back in 2017, it was nearly impossible to have a profitable business selling products as both credit card processing and banking were shutting accounts down left, and right. We had to deal with many shutdowns. Moving bank to bank, credit card processor, to credit card processor. It was a nightmare of mass proportion. Scammers leaking in the dark to steal your money. Read more>>

Samuel Austin | Architect and Watercolor Artist

Risk taking is an important part of making progress in my career. I learned at an early age that every action has risk and that the important thing is to know and understand the risk. Calculated risk taking is a natural component of my decision making process. In some ways it seems to be related to what other people consider luck. But it is not really luck. Really it is just a willingness to take risks and understand the potential down side. Read more>>

Lewis Frazier III | Wildlife Photographer and Conservationist

One of the most critical things I learned early in my life was the importance of taking risks. I have heard many people talk about taking risks with the obvious upside being a chance at success. This seems like the main reason for taking risks in life, but for me, it has been the repeated failures that have taken me the farthest. You read that right – failure has shaped my journey – not success. That probably sounds crazy, but allow me to explain. Deciding to take a leap in life means overcoming our fear of failure and going all-in towards the goal. Read more>>

Daniel Okwena | Managing Attorney

Taking risks is oftentimes daunting. But I like to think about risk in the context of conviction and reward. When I’m convinced about a plan of action and it’s potential benefits, I go all in in-spite of the fear of failure. I cannot think of any major achievement in my life and career that didn’t require taking risks. Immigrating from Nigeria to the U.S was probably the biggest risk I have taken. It turned out to be a life altering decision for me. Leaving behind everything I had ever known, family, friends, career, culture, climate, etc., Read more>>

Tyler Holt | Entrepreneur & Personal trainer

I personally don’t believe anything truly great happens that doesn’t involve risk. Taking risks have lead to the best results for me whether that be personal or business. The phrase “Great risk, great reward” stands true. I have always believed that people should do the things that scare them. Those types of things typically involve a good amount of risk. I always view risk as giving me two options. Option 1: I take the risk and I get the reward I wanted. Read more>>