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.

Kenneth Steadman | ISSA Master Trainer/NCSA TSAC-F

I’m a risk taker. I am willing to put all my eggs in one basket and believe in myself. I find that people create a plan B as an easy way out because they are uncertain. After 21 years in the military, this is what it boils down to. Read more>>

Emily Roan | Visual Artist

The saying, “Everything you want is on the other side of fear” is a true north star for me. The gold mine my 20’s have taught me is that self-confidence and self-actualization are direct reflections of what is present in my life. I have discovered that an immediate correlation happens between success and risk taking. In the moment, a risk may present itself as a limiting belief you move through, an investment in a venture that is illogical to others but a rush of resonance for you, or even an impulsive but necessary decision. Ultimately, it’s personal. Risk taking taught me that my intuition and desire are always holding hands. In my opinion, risk taking is a component of greatness; it will always show you where your roots are expanding. Read more>>

Jenny Roentz | Owner of BeLocal Parker

Ready Set Go! My daughter had signed us up for a 1/2 marathon in Denver. I have ran a few 1/2 marathons and relays so I knew what I was signing up for. I was working at a Real Estate office at the time and my hours were roughly 8am – 6pm. I made excuses to not train before work and I was burnt after my 45 minute commute home. Needless to say, my daughter was training hard and counting down the days to race day. I ran a bit on the weekends and told myself I could do it. I had done a few right? Well race day came and my daughter had to back out because her knee had strained and filled up with fluid. Read more>>

Jen Seregos | Founder & Digital Marketing Specialist

What many people would consider a risk has been par for the course for me in my life. I’ve had an entrepreneurial spirit from a young kid and started my first business in college. I think many people consider entrepreneurship as risky, but I think it’s the most secure way to build a career. Think about it – If you have a job in corporate or wherever, you’re relying on ONE source of income. If you grow your own business, you’ll likely have many clients. If you lose one client, it’s not the end of the world and you’ve created processes and structures to get more. If you have one employer, and you lose your job, that’s a really big deal. In fact, it can be devastating. So taking “risks” has been my greatest source of success. I now have a process and strategy in place in my business to not only replace lost business but to scale and grow. I wouldn’t trade that for any “secure” job in an office. Read more>>

Pipin’ Hot | Musical Artist

As musicians, risk is part of our everyday life. Art is very personal, and as such, sharing it with others bears an inherent risk. When we perform live, we are presenting a piece of ourselves for the world to see; we are vulnerable. We pour our hearts and souls into our music and there is always the chance that it will not be well-received. Building improvisational sections into our performance comes with an even higher risk – the music could turn anywhere at any moment, and we have to make the split-second decision to turn with it or hold fast. We like to think of these as “high risk, high reward” situations. There is nothing more gratifying than to play a piece of original music, improvise into a totally new section, and land somewhere else entirely together. This musical conversation allows us to connect with each other and our audience in a deeper, more meaningful way than words ever could. Read more>>

Delfina Darquier | Real Estate Advisor

I think about risk as something that needs to happen at many points in your life. Some risks are bigger than others but they all count! I think the biggest risk I took was to move to the US from my home country, Argentina. That was a big life change. Culturally it was a big adjustment and sometimes it still is. Another big risk was changing from a completelly different industry to Residential Real Estate. I like to take what I call “educated risks”, where you make the leap into something new, but you still have pretty good idea as to where and how you will land. All of the risks have always paid off and it is important to learn to move out of your comfort zone. Read more>>

Sydney Holliday | Interior Stylist & Entrepreneur

After graduating college, the freedom to decide what to do with my life felt paralyzing to me, and stopped me from taking action in my career path and personal growth. As someone who has struggled with severe anxiety; risk, uncertainty, and ‘putting myself out there’ were terrifying to me. I was so afraid of all the unknowns in my life. I felt extremely stuck in my comfort zone; living back in my hometown, serving and bartending to pay my bills, feeling debilitating anxiety about what my next steps should be. Yet, all of the best things in my life have happened as a result of embracing uncertainty, taking action despite feeling afraid, and stepping outside of my comfort zone. Read more>>

Daniela Wolfe | Content Creator and CEO of Barred Rock Social

All the best things that have ever happened to me, came from taking huge risks. Leaving behind a life, career and moving to a city where I didn’t know anyone–that was a huge risk. Taking on the responsibilities of starting a new business from scratch–another big one. In both cases what motivated me was the conviction that there was something better for me out there. I knew that if I wanted to achieve real progress in my life, I couldn’t simply stay where I was: if I continued repeating the same routines that were making me so unhappy in the first place, I would just stay unhappy. Read more>>

Cie Hoover | Artist / Musician

Risk…The proverbial “leap of faith” that has, and will most likely continue to shape my art and music. Was there risk involved when I chose to forgo the family business in Virginia and go to college for music business in Nashville instead?…absolutely. Was there risk involved when my wife and I quit our fulfilling full-time jobs in Nashville to hit the road for a year to tour with our music?…definitely. Was there even more risk when we decided to continue life on the road and tour nonstop for a total of six and half years?…yep. And, was there risk involved when I started putting myself out there in the visual art world?…totally. Read more>>

Wayne Gassmann | Video Production Company

Life is about high risk and high reward. Being a freelancer is a huge risk that work might not be there, but you do it and never throw all your eggs in one basket. The rewards are immense. It was a risk leaving my News/corporate life, but it would have been a bigger risk for my mental sanity if I stayed. Read more>>

Kyle Moon | Singer/Songwriter for Kyle Moon & the Misled

If you don’t take risk you never know what you are capable up. When I was 26 my wife (then girlfriend) asked me what I regret in life. I told her that I lived with a band for two years in college and never learned how to play an instrument when it was always around me. She bought me a guitar for more 27th birthday and couldn’t put it down. I was not very good and probably only knew three chords when I decided to play open mics and put myself out their. Looking back it is embarrassing to listen to but I loved the feeling and the outlet it gave me. Read more>>

Beverly Belury | International Pet Sitter

Here’s the truth: You don’t know until you go. That was the risk we took when the possibility of travel by pet sitting was an option for us. We asked a ton of questions, research the bejeezus out of it, asked friends and family and actual pet sitters what they thought. It just came down to the fact: You can’t really know what it might be like unless you are on the field giving it a try. So off we went. Deciding to mitigate some of the risk by: going local, taking on a few very short pet sits, having the assignments within driving distance, limiting the number of pets. From there we used a concept we used in our own business: Create and then adjust til it feels and performs they way we want it to. Read more>>

Dizzy Grant Diamandis | Entertainer, performer, advocate

Taking a risk to start something new or unique has always been and will continue to be hard. Most people or hardly anyone will believe in your vision. If you have enough knowledge or at least a starting point of how you get there you should be fine. In my case I struggled a bit to get support from nonprofit organizations to create an event that helped the community on HIV AWARENESS. After the success of my first event that I hosted they believed it me more enough to have a second event. If I hadn’t taken the risk in reaching out and executing my vision my projects would of never had happen. Read more>>

Hailey Brontide | Entrepreneur

Risk-taking is an essential part of everyday life, both from an evolutionary and self-development standpoint. I may be so bold to say, risk-taking is one of the most significant determining factors in someone’s success and overall growth. The reason being, evolutionary as people, our survival is based on taking measured risks. This measured risk has allowed us to evolve and grow and continues to push us to make decisions to either stay comfortable or improve. Read more>>