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.

Jannelle Allen | Popcorn business owner

Risk is a necessary part of life and it can’t be avoided. In order to progress and succeed, it is important to embrace risk and use it to your advantage. I have learned that taking risks, both personally and professionally, can sometimes lead to some hard lessons, but I would rather have that experience than to shy away from risk. Read more>>

Amity Krause | Coach | Trainer | Podcast Host

Thinking about risk, for me, has always been about balancing intuition with insight. In the real estate world, and certainly in my transition from retail, to realty, to founding True North Transaction Services, risk-taking has been a central theme. It’s not just about taking risks; it’s about making informed decisions where the potential reward outweighs the potential setbacks. Read more>>

Casey Knox | Entrepreneur & Avid Snowboarder

I consider risk to be more exciting than scary. I think with risk comes new opportunities and forces you not to stay too comfortable. Taking risks in life has helped me to stand out, in-turn, this has helped me succeed in not only my business but on social media as well. Read more>>

Tim Brown | photographer

without risk, there is no reward. As an artist, it is important to challenge yourself by trying new ideas, techniques or even marketing strategies. This is how we learn to grow and evolve our craft. If we don’t take chances, our work will stagnate, as well as our creative minds. Read more>>

Tanner Digby | President Commercial Real Estate Brokerage Firm

Risk can be a scary word for the majority of people, especially for business owners. I was fortunate enough to have been raised in a family of entrepreneurs. As such, I’ve been able to evaluate a risk averse approach and compare it to risk prone approach, from a very young age. Although my position on risk is certainly not perfect, I have come to find that I lean more on the side of the risk prone approach. I think it’s incredibly important to take methodical risks, in order to scale your business to the next level. I carefully use the word methodical, as I also believe that flippantly taking risks can quickly cause a downward spiral. In summary, taking methodical risks, with wise counsel is vital for taking your business to the next level. Read more>>

Will Fowler | Overland Video Creator

Risk is something that plays a big role in traveling the backcountry. In some ways it’s the risk that makes the adventure exciting. But the balance of seeking out remote places, knowing that if something goes really wrong, you could be in trouble, and remembering that we’re doing this for fun, is really important to keep in mind. But if you think about it, there’s risk for not taking action too. There’s a risk that if you stay let complacency take hold of you, life will pass you by and you won’t participate much. So honestly, when we venture out into unknown places in this world, we’re addressing one risk by accepting another. Read more>>

Rian Elizabeth Gufarotti | Ayurvedic Health Counselor, Yoga Teacher, & Retreat Guide

As a massage therapist turned wellness entrepreneur, risk-taking has been integral to my journey. It means having the courage to pursue new opportunities, even when the outcome is uncertain. It’s about embracing challenges, stepping out of comfort zones, and being willing to invest time, energy, and resources into ventures that align with my vision. Risk-taking involves calculated decisions, strategic planning, and sometimes making tough choices, like selling my business during Covid, to pursue a deeper passion. It’s about believing in oneself, being adaptable, and having the resilience to navigate obstacles along the way. Ultimately, risk-taking is about seizing opportunities for growth and fulfillment, even when there’s a chance of failure. It was through selling Natural Therapeutics, a top rated Massage clinic in Colorado Springs, that enabled me to really take risks and trust my self to follow my dreams and keep reaching my goals. Read more>>

Erika DeMaggio | Owner at Soirée Bridal Boutique & Soirée International

I was raised on the idea that you’ll never get something different than everyone else has if you aren’t willing to do something no one else is doing. I apply this to life and business. I will make big, unexpected moves, change my mind when a better option comes up along the path, and take a last second opportunity just to see what happens. I typically take stock of the commonalities of my competitors and firmly decide to abscond. I don’t find much value in announcing your risks. Move quietly, your results will speak for themselves. Add in having a true heart for you clients, and you’ll give them a unique experience that they can’t wait to share with others. Read more>>

Jerry Allison | Artist/Photographer

I think it has always been part of my nature to be a risk-taker. In high school in the South, I had two sets of friends – the super-smart kids who were in the academic clubs, and the juvenile delinquents, who were their own outsider club. The smart kids were intellectually exciting and the hoodlums knew how to party. Fast forward to being a young adult (a) in a collapsing marriage and (b) finding that working as an Architect was not nearly as creative as I had imagined and (c) left me no time to pursue my passion for drawing and painting. When the marriage ended, I got a map of the United States and threw a dart at it. It stuck in New Haven, Connecticut and I thought “That’s a message from the Universe – seek a New Haven” and I did.I knew no one nthere and arrived with no job and very little money. That risk-taking opened up my life and exposed me to the East Coast world of museums, galleries, serious music, film and theater, all the aspects of “high culture” that were (and are) so absent from the South. Without that leap into the unknown, I could never have become the Artist I am. Read more>>

Ramone Sanders | Restorative Practices Facilitator & Training Director

I believe healthy risk-taking for the sake of personal and professional growth is a must. I’ve been fortunate to have mentors and supervisors who believe in experiential growth and the practice of managing up. Throughout my professional non-profit career, I have been encouraged and entrusted by mentors and supervisors to step out of my comfort zone and take calculated risks that have promoted my growth as a leader. Without taking risks, I wouldn’t have taken advantage of the opportunities that have supported my growth within and beyond the workplace. Read more>>

Aria PettyOne | Drag Performer/Producer

Starting your own business is a huge risk just to begin with. It takes a lot of courage to bet on yourself in today’s day and age. For myself when I think of risk I tend to think if this fails will I recover, in a way that makes me feel okay with this failure. Read more>>