By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Brian Murphy | Food Truck Owner / Entrepreneur

“Don’t Hide Your Money Under the Mattress” From a very young age, I’ve always been told to make cautious decisions and to follow the norm. As I graduated college and entered the workforce, my uncle pulled me aside and we had one conversation that ultimately changed the direction of my future. He told me that I should do the opposite of what I have learned all along. He told me to invest like the wealthy and to take chances. “High risk, high reward” was his exact words, and I loved every bit of our conversation! Working my way up the corporate ladder in the restaurant industry, Read more>>

Austin Nicklas | Cinematographer

There are many different types of risks a person can take in their life. I believe as long as the risk is fueled by passion you should take it. Looking back at college me, I took a risk to uproot my life by dropping everything and moving from Colorado to follow a dream I was passionate about. Now with risk, there does come failure, but it’s how you manage that failure that ultimately helps you learn and grow. Read more>>

Taylor Dinh | Photographer & Editor

Risk is a huge thing to think about as a photographer. At the end of the day, there are over 100 photographers in Denver so the risk of the industry ends up being the same question for all; why would someone choose me? Taking risks in my personal life and career has ended up showing my tenacity and courage to keep pursuing the best for my small business. Risks eventually have a downside but the mountain of ups is way greater than the downs. Read more>>

Anna Khandrueva | Psychotherapist

Risk requires us to be vulnerable, which is uncomfortable for many. In order to risk something, you have to be prepared to lose it. It may seem easier to stay in the status quo, suspended in never knowing of what could have been. But where’s the fun in that? I believe that taking risks is necessary for growth and thriving. The first big risk I took was moving to the United States from Russia at the age of 18. I went from the huge bustling city of Moscow to the small and picturesque Fredericksburg, VA to attend college. I left my life and family behind in the hope of finding personal fulfillment – or so I thought. Read more>>

Deirdre Butler | Owner of Big Round World

The perception of risk is a personal notion, each of us having differing tolerance levels. Your concept of risk might be my opportunity, and vice versa. I’m a Brit by birth and spent my childhood living on the edge of Dartmoor National Park in southwest England. The farm next door had horses, and I learned to ride on Blossom, the cart horse. I remember the day she cantered for me – she knew I’d mastered the ability to hang on. From the age of 8, Blossom and I would disappear alone for all-day rides up on the moor. Many years later, I heard that adults in our village would shake their heads at my antics. They perhaps saw my actions as risky, while I knew that Blossom would keep me safe and if I became disoriented, she knew her way home. Read more>>

Heather Alexandar | Yoga Teacher, Astrologer, & Cosmic Wellness Luminary

Taking risks can be extremely daunting and even frightening, but also quite rewarding. Starting my business in itself was a risk. However, it was a ledge that I am grateful I jumped off. When I first started my business, I started out as a private yoga teacher in Denver, a city with a plethora of yoga teachers, I knew that I had to find my niche quickly. I’ve always loved astrology, and in my studies of astrology and yoga, I found that each zodiac sign relates to a certain part of the body and can affect how we move. So I began teaching classes for each New Moon and Full Moon every month. Read more>>

Gene Hayworth | Proprietor of Inkberry Books; Publisher and Chief Editor, Owl Canyon Press

For me, risk is essential. Without trying new things we cannot move forward. Everyday we are faced with new decisions, and it is easy to sit back and let life happen–but that is not a life worth living. Read more>>

Gary Sheer | Photographer

When it comes to photography, I love taking risks. Of course I am not talking about life threatening risks such as a the very popular yet idiotic train track shoots you see on social media. I am talking about challenges that force me to rethink how I use my tools. As an event photographer I am constantly relying on myself to innovate solutions to developing obstacles. A great deal of the time I am traveling to an unfamiliar environment and there is only so much planning and research that can be done prior to arriving at the space. Read more>>

Macy Jo Kooima | Bespoke Residential Interior Designer

I believe “risk taking” is this special gift that is there for each and everyone one of us. Unfortunately, only some acknowledge it, lean into, and got for it. It means you are willing to go off the beaten path and listen to your soul’s calling. That itch, that dream that won’t stop calling you. Are you gonna pick up that phone and answer or are you going to letting it keep ringing and regret years down the road you never did? I think there are different levels of taking risks…. sometimes more calculated risks and sometimes it’s putting all your chips on the table, knowing damn well you could lose it all in a second. For me, I am the second version. Read more>>

Diana Rene | Home Management Coach

I think risk is inevitable as an entrepreneur. You aren’t guaranteed anything and have to set aside a steady paycheck in hopes that you will make it happen on your own. Read more>>

Susannah Dowell | Photo Documentary Photographer

Risk taking has been monumental for me. An incredibly impactful therapist I had in my young years put it to me like this: life is a giant set of monkey bars. Grab whatever comes next. It will appear as soon as you need it – just keep moving forward. The risks I’ve taken have led me down a truly rewarding career path. At the advice of this therapist, I took a hiatus from my awful, boring desk job working for the department of defense at 26 years old to go west to Wyoming and work as a cook for an elk hunting outfitter and get some awesome new imagery of the wild west. Read more>>

Timothy Morrissey | Founder and Owner

Life is a risk. The thought of leading a life unfulfilled because I didn’t take a chance or a risk, is that a life really worth living? I have always wanted to succeed and live life on my own terms and that involves taking risks. When I moved to China to start my business, I did it with $700 in my pocket and a few connections that I had managed to make which mostly meant I had a place to crash when I first arrived. Needless to say some 15 years later, the risk was worth it. I cannot imagine my life had I not taken that risk. I guess, to a degree, I have not really viewed failing as an option. Read more>>

Michael Pena | Social media influencer & cannabis connoisseur

Honestly Risk taking for me is huge because my whole life has started on risks. I got to where I am now because of risks I had to take Read more>>

CLs | Street artist

Risk has been the spice of life in my life/art career. Being uncomfortable and outside your box is the best way, in my opinion to grow as a person and as an artist. Read more>>

Buford Brown | Digital Creator

High Risk = High Reward. You can not create a big business, become rich or even successful without willing to risk it all. Read more>>

Raquel Ortiz | Cdl truck driver & Artist of all mediums

I think that without risk you go nowhere. Risk helps people get out of their comfort zone to better opportunities. It helped me be where I am at right now. I left many “good jobs” for something better and here I am now working a career I never thought I would and only dreamed of. Read more>>

Krys | Blogger & Publicist, That Chick Krys

I believe in having a growth mentality. Risk taking is a paramount component in growth and being an entrepreneur. When I was 17, I went to audition to become a tribute artist (which I ended up doing globally for 11 years). I only had “fixed mindset” friends at the time, so I didn’t tell anyone I was going to audition in case anyone tried to discourage me. Though I wasn’t the most talented singer or dancer, my dream as a kid was to be a performer, so I rehearsed a lot. The minute I stopped caring what people would think of me, and chose to only surround myself with those with growth mindsets, I grew and attracted opportunities in both life and my career. “No risk, no reward”, as they say. Read more>>

Teressa Gehrke | Founder & CEO of PopCykol

I think about risk in terms of how likely will the outcome of the risk be to my success as a person, company, or level of contentment and joy. I’m not afraid of risk. I’m actually a very thoughtful and logical person. So, I weigh the pros and cons of the risk and the actions I have to take. Read more>>

Victoria Cumberbatch | Community Management Consultant

Risk, is a natural part of the cycle. It’s the more stressful part if you’re Type A, but risk can provide great reward. Throughout high school, I was captain or president of all the clubs and sports. I spoke at graduation and I really felt myself! I finished college in three years to a recession and no one giving a whole crap about some BA degree, especially one in international development. All those internships I was assured would mean something, meant nothing at the end of the day. Read more>>

Alyssa Brewster | Licensed Esthetician & Wax Specialist

Growing up, my Dad alway said, “great risk equals great reward.” That very idea, as well as watching him take leaps of faith without hesitation, created an admiration in me to be like him. I watched my Dad dive head first into any risk he could; all were his greatest successes, even if they failed. When I think about risk, I often find my mind wondering into the “what if’s?” but understanding that the worst thing that can come out of risk is growth is what makes it all worth it to me. Starting a business at 21 years old, without any prior knowledge of the intricacies behind a brand, is quite literally the scariest thing that I have ever done, but easily the best. Read more>>

Jamaica Dolinsky | Acupuncturist and Neuromuscular Massage Therapist

I think risk is a personal assessment. In my opinion, you never know until you try. I had started a private practice in south Florida and why would I not try to create the same in Colorado. Personal connection is key is my profession. Once you find your passion within your field, you should excel. If you can talk about your passion with education to back it, then you can spread your own uniqueness. Risk is rewarded by bravery. Read more>>

Julia McCafferty | CEO & Founder of Level Up Locators (Denver Apartment Locating Service)

Risk is essential. Trusting yourself to take a risk is what’s going to fuel your fire. I believe that you grow the most when you’re outside of your comfort zone and always pushing yourself. You have to be willing to let go idea of being ready and just take the jump. Move somewhere new, meet new people, start a new business, but most of all believe in yourself and whatever you do, do it will all of your heart and never look back. Deciding to take the risk already has you one step closer than anyone else just thinking about it. Read more>>

Katie & Justin Snyder | Coffee Shop Owners

Our entire foundation as a couple has been built on giant leaps of faith. Risk taking is ultimately taking a bet on yourself – as an individual and as a team – knowing that you have the strength in each other to make anything possible. When one starts sinking, the other saves. It’s a collective success. So although many risks have been taken, the blunt force terror of risk feels manageable with trust in one another. Read more>>

Jordan Lucky | Tattoo artist

Risk taking is pretty much my job as a tattoo artist in every way. The reason I have a calling to tattooing my whole life is because no matter what job I always had, good money or not, I was still just getting by but wasn’t happy. I wanted to do something everyday that I actually cared about. I wanted to live my life with some sort of meaning. Nowadays, the risk more involve stepping out of comfort zones, or trying to convince a client of a change in design process for the better, even if it results in changing their original idea. I love to take risks, because even if you fail, you know that you believed in yourself enough to give it your all, and you will try again. Read more>>

Brad Stine | Comedian, actor , free speech advocate

Because of my specific type of comedy, risk has become part and parcel as to how I go about it. I am a unicorn in that my comedy comes from a conservative/Christian POV which is extremely rare in comedy and the arts in general. I am committed to defending free speech and liberty in America which is what comedians traditionally specialized in. Read more>>

Beau Alleman | Entrepreneur

Taking chances and risk has played a huge part of my success with genuinemoneybusiness! From trying to figure out what people really like to supplying every need! You have to do it for the people. My brand had a huge meaning to it that will live on forever! Be who you want to be, be genuine. Without trying new things and taking the risk and failing you will not learn! Read more>>