Taking Risk is essential, but how much, when and why? Taking risks effectively is as much of an art as it is a science and we’ve asked some of the brightest folks in the community to tell us about how they think about risk taking.

Reven Marie Swanson | Sculptor

Taking risks is part of any artistic career, both in the studio and in the marketplace. There is no one formula to succeed as a full-time artist. I often remind myself of a book I read as a kid, “The Little Engine that Could”. Try something to see if it works. If it does or doesn’t, try again. Building a career is a lifetime event. Allow time and experience to move towards your goals. If you’re genuine and believe what you are doing is your best creative act, taking risks become less frightening. Read more>>

David Cudd | Owner of Venture: A Service of David Cudd Photography

A good amount of people who live and work in Summit County, CO have more than one job to be able to afford to live in this beautiful mountain town. At one point, I was working 3 jobs/gigs, including a photography job, so that my family could afford rent, food, and to pay other bills. I felt stuck, exhausted and overwhelmed. I was worried that if I quit one of my jobs we would go hungry or not be able to pay rent. I had this deep desire to start doing something I wanted to do – to start my own photography business, but I had no time or energy to work on anything toward that goal. Read more>>

Cheryl Derricotte | Artist & CEO

When I think about risk-taking as an artist, it is a balance between making work with strong, often political, content and the volume of work. My primary mediums are glass and paper. Fortunately, sculptural glass art is ruled by the creation of individual artworks. When making work-on-paper, I have chosen to go with smaller editions, 5 – 35 tops. These are my strategies to solve the problem of too much material/supply outlay upfront and too much inventory in the studio. Read more>>

Chris Carmichael | Founder and Head Coach of CTS, Olympian, US Olympic Committee Coach of the Year

Early in my career I didn’t perceive things like moving to Belgium with $300 in my pocket to race my bike for two years as risky. I was all in and had nothing to lose, so it was hard but not risky. Risk comes when you have something to lose. Before I started CTS, I had a successful career as an athlete and coach at the highest level of sport. Walking away from that to start a business was a risk. What I’ve found over the 22 years CTS has been in business is that risk pushes you into overdrive, which can be helpful for an entrepreneur. Risk forces you to take action, and because some of those actions will lead to failures, risk also teaches resilience. Read more>>

Cindy Frigard | Designer with a CPG Side Hustle

I have never been afraid to make a change when I thought it would better my life. Some people might think of the choices I’ve made as risky, but they’ve always led to something better. For example, my husband and I quit our highly paid corporate jobs and sold our house in California so we could take a year off to travel when we were in our mid-30’s. When we got back, we took corporate jobs in Michigan and ended up quitting those four years later to move to Colorado to start our own company with one non-paying client. Read more>>

Antonio Barajas | Business Owner

The way I think about risks is if you don’t take any throughout your life or in your career, you will be stuck in one place or position wondering what would have happened if you didn’t take and approach different opportunities out of your comfort zone. I took the risk of leaving my hourly pay job without knowing if my business was going to be successful. Read more>>

TJ Fink | Tech Journalist & Molecular Mixologist

The most fulfilling parts of my career have always involved some form of calculated risk that pushes me outside my comfort zone/s. As a full-time freelancer for everything I do, my life is a constant cycle of mini-experiments that force me to utilize my favorite skill sets in new ways, and without any risk, there can be no reward. Read more>>

Ben King | Cheese Technician & Business Owner

Every decision we make includes a consideration of risk and reward. Sounds simple enough but it can get complicated fast when we start taking all factors into account (both known and unknown). At a certain point too, there has to be a leap of faith because you will never know the outcome unless you try it. When we were first starting there was a small amount of risk to setting up the business, to buying all of our equipment, to getting all of our legal permits in order. Money needed to be laid out for us to even test our idea. Read more>>

Christina Gressianu | Photographer & Entrepreneur

We’re always taking risks. Just being alive, there are risks all around. We’re just more aware and present to some of them than others. Driving is a risk, walking down the street is a risk — a tree branch could fall on my head or I might be enticed by a bakery. When I first started working for myself in 2008, I asked my older brother if it was a crazy. Should I just go get a job. His answer changed my life. He said “It’s a just a matter of how much risk you’re comfortable with.” Amazing that it wasn’t a matter of being smart or talented! Just a matter of risk tolerance. I was so energized by that idea, that I dove in. Read more>>

Cailey McDermott | Magazine Owner/Publisher & Photographer

In my life and career I’ve done a lot of jumping first, looking later. I moved from Vermont to Colorado, sight-unseen. I knew one person in my new town. After 3 years, I quit my job at the local newspaper to pursue my photography business. (My very new photography business.) I had no business plan, not much money saved. I just jumped. … and then I got a job waiting tables for a few years until my photography business could stand on its own. I enjoy risk-taking. It makes me feel electric. I recently took another major risk. Read more>>

Heather Divoky | Detail-Driven Artist & Designer

Risk permeates many aspects in my life, which I think is why I am so comfortable with it. I see it as a necessity now. As a visual artist, I am placing a risk on myself every time I show a new piece of work (or behind the scenes of work, which sometimes can make me even more vulnerable!). How will the public receive my new piece of art? How will that affect me emotionally? Will someone like it enough to purchase it? These are all very basic risks I take when I open up my creative practice to the world, especially as a small business. Read more>>

Kylie Berger | Hairstylist

I am someone who loves a plan I like to know what I’m doing, when I’m doing it, and what level of risk is involved. That being said, I decided to quit my job of 10 years at a commission hair salon the day we got shut down due to Covid. I was about to have my first baby, I knew I wanted more flexibility with my schedule and I was excited to be my own boss but I was always worried about changing things up and risking the career I’d spent so long building. When I realized we were going to be shut down for weeks, I made the fastest, biggest decision to take what turned out to be two months to start my own business, Hair By Kylie. Read more>>

INTA:LECT | Hip Hop Artist

I think risks are necessary for progression. Playing it safe will keep you in a stagnate place. I prefer to live outside of my own comfort zones. Big risk big reward, right? Honestly, the better answer to that question is how not taking risks has played in my life/career. You miss 100% of the shots you don’t take and for me that is so close to the truth it hurts. From record deals to business deals, the risks I never took affected me the most negatively in life. It wasn’t until I started taking those risks that I began to find success and flourish. Read more>>

Matt Brennan | Small Business Owner, Family Man, Veteran

I think about risk like I think about driving a car… It is necessary to get where you want to go. Everything we do in business, family, fitness and other hobbies, risks must be identified, given a value based on personal beliefs and experiences, then acted upon in accordance with those factors. In my world, family is first (behind my faith, although I fall short) in all I do. If I were to take on a new project, job or business, the risk of doing so is weighed against my household and what direction my wife and I are taking our family of five. Read more>>

Morgan Jones | Artists & Astrologist

Taking risks is probably the thing that has taken me farthest in my life and my career. Results I have gotten from risk taking have surprised me and brought things into my life I only thought I could dream of. I can’t get enough new experiences, meet enough new people, or learn enough new things. I think the most growth can be acquired in uncomfortable positions. When you take a big risk you are opening yourself up to big reward. If things don’t go according to plan you can always pick yourself back up and know that you gave it a shot. Im proud of myself even when I take risks and I fail because I was brave enough to at least try. Read more>>

Travis Hatch | Videographer & Media Production

In March 2020 when the Covid 19 pandemic hit and we were about to go into lock down, I got a call at 8 am Monday morning to tell me that my company had gone bankrupt and my employment (along with everyone else) was terminated effective immediately. I had been working for this company for 3 years, full time employment, full benefits, and that was all gone in an instant. In that moment I had an epiphany as I thought about finding another job. Read more>>

Sheryl Zacharia | Artist working primarily with clay

One could say that trying to make a living as an artist is a risk in and of itself. But I think most artists feel compelled and love to create…it’s not really a choice. I started out as a painting major, but after only 3 semesters, dropped out of college and moved to New York City with $75 and no job or permanent place to live. I realized songwriting, which I had been doing since childhood, and performing was really what I wanted to do. I had all kinds of crazy jobs, mostly working in restaurants to support this endeavor. Read more>>

Casara Andre | Veterinarian & Entrepreneur

My paradigm around risk assessment and management was formed early on in my career through my experience as a military officer. As a veterinarian for the Army Veterinary Corps, I have had unique exposure to exceptional leadership, team, and organizational training that have continued to serve me well throughout the civilian portion of my career. Risk aversion can be as dangerous as inappropriate risk tolerance. Read more>>

Paul Dreyer | CEO of Avid4 Adventure

We live in a world that has become more and more risk adverse. From all directions – media, teachers, parents – we are all bombarded with messages about avoiding risk, keeping ourselves safe. My take on risk? We need to manage risk, but not avoid risk. In fact, I look for opportunities (and try to help others look for opportunities) to lean in to risks – positive risks. Sure, risk avoidance leads to safe spaces, but I believe that safe spaces lead to lack of growth and development. Read more>>

Jessika Sands | Trauma therapist

I think without risk, there would be no forward movement. Everything that is inherently unfamiliar could be considered a risk, which is why choosing my career path and starting my own business has been a risk at every step. It has also been completely worth the lessons learned. Failing is a difficult concept in this culture because it is, as a concept, taught less as a learning experience and more as something you are not supposed to experience because it is labeled negatively. Without failing, we cannot learn and without risk, we cannot move forward in any area of our lives. Read more>>