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.

John March | Producer, Musician, Filmmaker, Sound designer &Mixer

I have two perspectives on risk. Risk can have a lot of different connotations because many people are risk-aversive. Our world is challenging. Risk is seen as a potentially negative component because it asks that we explore and investigate the unknown, but I believe that calculated risk, and having an emotional and intuitive connection to outcome, can mitigate a lot of aspects of risk aversion. As a person who has spent his life pursuing creativity and craftsmanship, risk is an inherent component with regards to what I do because risk allows for magic and the unexpected moment to arise. Risk is a critical aspect of what I do and a large part of how I have lived my life, as a musician, a filmmaker, a parent, a husband and as an activist. My heroes have always been a combination of powerful and inspirational musicians who have high level skills as improvisors, and social and environmental activists who devote their lives to substantive change in the world. Improvisational musicians spend their lives devoted to exploring the moment. Read more>>

Jess Tiergyn | Counselor, Coach and Adventurer

“There is freedom waiting for you, on the breezes of the sky, and you ask ‘What if I fall?’ Oh but my darling, what if you fly?” — Erin Hanson I was taught by life and leaders throughout my experience on this planet to avoid risk and then I would be safe. I was told, just play it safe and you won’t have to be afraid. As a queer teen escaping an abusive home I wanted to be safe, I wanted the world to not hurt anymore. But if we stop for a moment we know that it is not true- we know that being alive on this spinning sphere of dirt contains intrinsic risks. The first time I threatened for being queer/non-binary- I knew risk was inevitable. The first time I notified a family that their teen had died in a car crash and held them as they sobbed- I knew risk was inevitable. The first time I lost a patient after working excellent CPR for an hour- I knew risk was inevitable. The first time I sat with a 4.0 student after they were sexually assaulted- I knew risk was inevitable. Read more>>

Witt Rabon | COO of Dro

Everything in life is a risk. You can risk your employment with someone else or you can risk bringing your dreams to reality. Read more>>

Skip Stone | STASHLOGIX – Founder

My life is a juxtaposition of risks versus predictability. My parents are every conservative, my dad’s an engineer that truly knows it all, and my mom is a farmer’s daughter. We mostly grew up in semi-rural Wisconsin, but at the age of 14 I moved to Madrid, Spain with my parents and my two younger sisters for my dad’s 2 year stint managing General Electric’s biomedical plant there. Spain rocked our world, but in a good way. We were transported from a rural hobby farm with horses, goats, chickens, cats and dogs to the cosmopolitan metropolis of Madrid that spoke a different language. Although there were many culture shocks, the biggest was the lifestyle and attitudes of the Spaniards. Their motto is “work to live, don’t live to work”, which is diametrically opposed to the American Way. Spain has a very social life. They stay up late, sleep-in late, and take mid-day siestas. They don’t have as many “things” as Americans but they’re life is very rich. They prioritize dinner with family and friends, which often includes singing and dancing. Read more>>

Amii Harmon | Innkeeper and Dreamer

Without dreams, leaps of faith, and courage we would tread the same path daily. Dream big. Then dream bigger. Now bigger still. Implementing this will bring you passion and purpose. Begin somewhere. One measured, faithful, full of fear step at a time. Move forward. Take risks. Don’t be foolish—or when failing consider yourself a fool. Learn as you go. Adjust. Revise. Continue. Steadfast toward your dream. We wrote our dream life/home/business on a grocery list notepad in 1985. We never forgot about it per se but carried on growing our life knowing more clearly our objectives and what would make us happiest. Then in 2012 we nearly dropped everything to purchase our dream property only to lose out to another buyer. Devastating. Suddenly in 2013 our dream property, one more amazing than we ever thought we could get, nearly fell in our laps. Better timing. Better long term. Much much work and great and risk. And it became ours. Check it out at where we’ve been steadily, happily growing out business and life since. Read more>>

Katharine Moustakes | CEO, Fitness & Nutrition Coach

Risks are what drive us. We’re always weighing the risk to reward ratios. I grew up in an environment that encouraged low risk, high reward. Although that may work for many, I eventually found that I was living out someone else’s dreams and goals, not my own. I took the leap and started my business 4 years ago because I saw an opportunity. I had know idea where it would take me, but if I wouldn’t have started then, I would be much further behind now. As I’ve grown, the way I look at it is that taking the high risk route can give you one of two outcomes: high reward or a big lesson. Since starting my business, I moved to a bigger city (Denver, originally from Omaha, NE), expanded my side gig to a full-time business, began new and adventurous hobbies, and implemented a work-life balance that I never thought was possible. Read more>>

Betsy Cole | Abstract Oil Painter

In spite of the difficulties brought on by life’s events, it has been important to move forward to find inner happiness. After my divorce I had an avocation as a decorator but no real career so I had to jump in and create a real business. I was unable to go to school due to repercussions from an accident so I hired a designer to teach me what I needed to know. I also hung around job sites pestering the tradesmen who were happy to share their information. This process of learning certainly wasn’t the norm but it was amazing and it worked. Although my business grew I needed to face the inner demons that had led to difficulties in my life and my divorce. This was all very demanding, tough and time consuming work but needed to happen in order to find happiness. Years after my business was in full swing, I was travelling in the US for work but had an itch to travel abroad. Heading to the desired destinations brought up feelings of fear and being anxious about all that could go wrong along the way. Read more>>

Maria Valentina Sheets | Glass painter and Art Conservator

In many ways, “risk” is the spice of life. Not enough and life has no flavor. Too much and you end up spiraling out of control. I spent a chunk of my early career trying to find that balance. As a young craftsman, I worked for other companies in my field of conservation/glass arts, surrounded by artists as we learned from each other. It was critical to have learned the basics but there were managers there writing their own “Manifesto’s” of operation. Everywhere you go, even among groups of artists, there will be people mandating operations, not open to changes. Having inspiration and mentorship is important to an artist but finding you are a a cog in a wheel can be toxic as well. In my time there, I felt I was either bending painfully to fit or involved in self destructive behaviors to protest. On a trip to New York to deliver a job, I read Agnes Martin’s biography, and learned that even hard working female minimalists like Agnes Martin did not always fit into the boys club in New York. Read more>>

Jenny Germano | Founder/CEO ICS Consulting: A Cannabis Consulting Business

Without risks I would not be where I am today. It has played a major role in my life and career. As I have matured and moved from being an entry level employee to a business owner, one of the most important pieces I have learned along the way is, life begins outside my comfort zone. This concept has been my rock in everything I do in my personal and professional life. When I started my business in 2015, I had gained a lot of experience working in a new industry as an employee but I had zero experience in owning or running a business. The biggest risk I took was leaving a steady paycheck and jumping off the cliff into the unknown – aka starting a new business – a completely new arena for me. I fell down a lot, made mistakes, I struggled, I experienced challenges and doubted myself all the time. I found my way to believing in myself through self commitment and resilience. Getting back on the horse again over and over really helped me build the muscle to face the challenges and it fostered the drive to keep pushing myself, even in the face of failing. Read more>>

Brenna Payne | Life Coach For Moms

I was a member of the U.S. National Luge Team for 15 years, I’ll tell you I am not a stranger to risk. However, when I became a mom I definitely settled down and had to think long and hard about the kinds of things I took on; it wasn’t just me this would have an effect on anymore. My family is always at the top of my mind now, but because of that, I know I need to model for my children what hard work and perseverance looks like. Risk taking is an integral part of reaching goals. When they see their mother set a difficult/risky goal, and then work day-in-and-day-out to achieve it, they learn to do the same. As a life coach for moms, I teach my clients how important goal setting and modeling is as well. I hope to lend a hand to the next generation to show that setting risky goals and doing the daily work toward the goals, is a healthy and what it takes to reach success. Read more>>

Todd Simmons | Wolverine Farm Founder & Director

When faced with critical career choices over the last twenty years, I’ve tended to place more value on the choices that would prompt movement in some way, whether geographcial, intellectual, or in developing a specialized skill set. The risk of this approach is often a sort clear-cutting of some stable foundation. I’ve been okay with that because the trade-off is the ability to honor and feed my own curiosity. Read more>>

Stephen Roach | Creative Director & Author

I believe more in what I have to give than in what I have to lose. Playing it safe never helps anyone. It may keep me from feeling uncomfortable but it won’t create positive change. Read more>>

Corrina Espinosa | New Media Artist

I am a risk taker. What a bold statement! When you say it out loud, and own it like that it feels so valiant, brave and confident, while simultaneously sounding a bit reckless, dangerous even. I should clarify— I’m not a dare devil or the gambling type and I don’t risk life, limb nor love. I am not the Evil Knievel of risk in the art world and in the face of uncertainty I take calculated leaps. Risk is uncertainty by definition, you never know what the outcome will be. Often the focus is on the possibility of negative, undesirable consequences. Risk literally means there is a chance that something bad can happen, something dreadful and scary. The cost can be downright terrifying. But the flip side to risk, is reward. The possibility that something good can happen is what makes risk so enticing, invigorating and thrilling despite any adverse prospects. Risk is one of those things in life that can really get your blood pumping, make your palms sweat and your stomach queasy. Read more>>

Tyler Shown | Production Manager & Community Relations Coordinator

Much like skydiving, the greatest moments in life aren’t experienced until outside the plane, on the other side of fear. After college I took a job in Yosemite, where I met lifelong friends and my eventual business partner. I proceeded to solo travel cross country for some months before eventually coming back to Colorado to start a production company, having no real experience in business or being paid to use my camera outside of some band gigs. In March 2020, more than two years into Jolly Mule Productions, my cofounder and best friend left for London, to be quarantined with his now fiancee, whom we met volunteering at an elephant sanctuary in Thailand! Crazy world, I know. They’re set to marry in 2022…lacking inspiration in my day-to-day and flight restrictions across most the globe, I left the self-employed life to join Wake Up Pueblo. A start-up marketing company on the surface, it’s the first full team of creatives I’ve been fully surrounded and consumed by. Six months in and everyday still feels like we’re creating pathways to success for a city so desperately seeking them. Read more>>

Robert Denner | Automotive Technician and Business Owner

I would consider myself a pretty risk adverse person but somehow I seem to constantly be taking risks in my life/career. This is mainly because I have a destination in mind and I have learned it is hard to get there without taking risks. The first risky career decision I made was turning down my mom’s generous offer to pay for college (even med school if I wanted) and instead pursue a tech certification. A few years later, I switched from boat mechanics to auto mechanics which set me back a bit. Five years ago, I moved my family from Pennsylvania and our entire support network to take a job in Boulder where we knew no one. And then most recently, I opened my own shop during a world wide pandemic. I am constantly trying to become a master of my craft. In order to do that, risk seems unavoidable. Read more>>

Jeff Campbell | Playwright, Theater Producer, & Performer.

Being an artist is always about taking risks. Art that plays it safe does not invoke the kind of emotion, or reaction I am after. I want to make things that inspire or agitate people to take the next step, so I want you to get angry, or sad, or anything that makes the audience want to learn more or do more about the subject of the art. That’s risky. I also invest in myself as an artist, and sometimes ventures don’t go the way you want because the execution was off or outside forces beyond your control, so that is extremely risky as well. There is however, a difference between throwing caution to the wind vs calculated risks. If I take a risk, it is measured and I have factored in what is at stake, and what I could possibly lose. I’ve lost money, battles, and I’ve even lost face. I try not to do anything that feels irredeemable, and that I couldn’t bounce back from. Read more>>

Alisa Messeroff | Women’s Empowerment Photographer and Intuitive

The dictionary defines risk as “a situation involving exposure to danger.” I don’t necessarily believe in that definition. I believe a risk is an opportunity that some are just too cautious to take. Society would probably view my life as “risky.” I quit my corporate NYC job in 2011 to travel the world with my husband. I can’t tell you how many people said to me “That is a super risky move.” I was always confused by that response. How could following my dreams be a super risky move? By taking this leap I started finding myself, slowly taking the steps to the woman I am today. I am a confident and succesful entrepreneur. If I had not taken the leap of leaving a stable job to follow my dreams, I can’t imagine where I would be. However, I can say that I know I would not be as happy as I am now. I am very grateful that I can wake up and look forward to each day; I absolutely love what I do. Read more>>

 Meghan Blanton | Wedding, Elopement, and Portrait Photographer

Life is full of risks! But if you want to get anywhere in this world, you have to be willing to put yourself out there, make changes, and try new things. It is hard to grow as a person or as a business without a bit of risk. Sure, you can survive if you change nothing and stay the course. But gosh, what a way to limit your potential. I’ve taken a lot of risks to get where I am. In my photography business, I take a risk every time I invest in educational courses and workshops. Will the money I put into it have a high enough return on investment? I take a risk when I reach out to potential clients. Are they going to say yes or turn me down? I take a risk when I change up my workflows and my marketing strategies. Are these changes going to hurt or help my business? And I’ll admit, not every one of those risks worked out in my favor. I’ve lost money and time on a few of them. But the ones that do work out are so worth it. I’ve grown tremendously and will continue to do so if I’m willing to take leaps of faith. Read more>>

Regan Rosburg | Artist and Professor

I think risk in life is necessary and helps my creativity, but I also take risks in the right places, so to speak. For example, I need stability in order to feel free to be creative, so I make sure that my daily tasks, health, spirituality and finances are in balance. If that is all sorted, then I will feel able to take risks in the studio, in research, and in travel. I used to take risks that put me in a position to be vulnerable or unsteady later. I learned that although the thrill might be great in the moment, it wasn’t worth paying for it with stress or instability…ultimately that is a creativity killer. Taking risks in the studio is necessary, though. I have learned to be comfortable with failure in the studio and have found it to be a great teacher. That comes from taking risks and doing something differently, or abstracting an idea, or even trying something that makes me wonder “is this stupid?” I have found that some of the best things are on the verge of being stupid. Read more>>

Duane Cronin | Asset Manager & Professional Investor & Property Developer

I think of risk all the time. So much so in fact, that I feel I may be an eccentric of sorts on the issue. I view risk as the intersection between outcomes and action. In one hand, you have a set of outcomes and in the other you have the actions taken or not taken that result in these outcomes. I feel the majority of people lack a solid platform for decision making, which invariably causes them to take unnecessary risks or mis-assess great opportunities as risky endeavors. This impedes their ability to get what they want out of life. Do you know anyone with a lucky roulette color or perhaps a lucky side of the coin toss? What sound logic can these biases be based on? Any good decision making process, should include an audit of how we can be sure our assumptions are true or likely to be true. Without this sort of audit, we are literally just taking shots in dark. When making a decision, my goal is to learn as much as possible about a pool of outcomes so I can accurately determine what is likely to occur or how likely it is to occur. Read more>>

Hilarie Grace | Actor & Model

I have always struggled with making “big life decisions”. I was always afraid that a single choice would dictate the rest of my life-both personal and career. I spent quite a bit of time at the beginning of my acting career not making any decisions out of fear that a role would come back to haunt me or I would be blacklisted. However, I had a friend tell me that a risk is simply a calculated decision. The act of not taking a risk is in fact, taking a risk. If I was indecisive, the opportunity would go on to the next person. Taking a risk isn’t as scary if I view it as a move toward my dreams. In the entertainment industry especially, it’s all about taking risks. From auditioning choices, costuming, performance influences, I’m constantly putting myself out there and hoping it impacts someone. The very nature of my industry is a risk that I gladly embrace. It’s my calculated decision. Read more>>

Karla Raines | Strategy Innovator & Abstract Artist

My career is defined by increased tolerance for risk rooted in a greater appreciation for my unique set of talents. As a consultant, I tested my abilities and discovered I could do more than I’d ever envisioned as I stepped out in courage with each new project. When you experience that sort of flow, you find that one success manifests the next, and on you go. Abstract painting propels my professional creativity and risk-taking, as it fuels my soul. Artists look at the world differently, and creativity opens a new portal. Years of painting have taught me to get out of my own way, not to tell myself no, and be open to the power of flow. I wouldn’t have discovered Differentiation Zone® without it. I invested ten thousand hours, so other purpose-driven strategists don’t have to. Read more>>


Daniel Dye | President, Native Rank Inc, /

There is no reason to take risks. If you fear embarrassment, rejection, or failure, remind yourself that the pain of regret is the worst there is. One day you’re going to die, and you won’t be able to do the things you can do today” – Steve Jobs. I always try to fall back on this quote when thinking about taking a RISK. Throughout my life I have found that almost all risks can mitigated by research, experience and sometimes a bit of faith. A favorite book of mine, Overachievement by John Eliot states, “All your eggs should be in one basket, so you’ll be single-minded.” I think this really relates to the fact that we cannot accept from the start we have a limited number of eggs and baskets. As it relates to risk, I always prefer to use these combined approaches, in an any new venture or other such related things. No risk, no reward. A simple analogy I would use is when a friend tells you about a new T.V. Read more>>