Rolling the dice: conversations on risk

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.

Veterinary medicine was just starting to be noticed by private equity groups prior to 2019. However, the global pandemic opened the floodgates for corporate interest in our field as they watched countless quarantined families invest heavily in their pets. As a small, local and independent veterinary practice, we’ve had to brace ourselves to scrap with corporate interests who, despite having less to offer our community, come to the fight with far greater resources than could ever be possible for us. Read More>>

Entertainment is a field where risk is simply part of the game. Originally, I began my career as an actor. Everything that we do is based on taking risks. choosing this field is a risk in that there are no guarantees, no hours to clock, no regular paychecks. but you have to commit 100% in order to find out what is possible. Auditioning holds a risk of not being selected, performing on stage holds the risk of judgment, positive or negative, from spectators and reviewers. It’s easy to say that I embrace the risk and uncertainty because I deeply believe in my myself and what I have to offer the world. I consider myself an entrepreneur, my talent is the product, and taking risks is an exciting and necessary part of building confidence and a strong career. Read More>>

How I think about risk?
Risk is part of the journey. Every big step I’ve taken—buying properties, rebuilding after bankruptcy, restoring historic buildings—came with risk. But I’d rather bet on myself and fail than play it safe and wonder “what if.” Risk has shaped everything I’ve built. Read More>>

You can’t be an entrepreneur without being a risk-taker—it’s all one big risk. You risk putting your work out into the world and opening yourself up to critique, sometimes from people who’ve never picked up a camera but feel compelled to tell you how they’d have done it better. You risk your finances when you go all in on making a business work, and you risk time—time that could be spent with your family or doing something more stable. Read More>>

I’ve never considered myself much of a risk taker. For most of my life, I’ve been afraid of the unknown—whether in relationships, education, creative projects, or my career. I often chose the safer path, not because it was what I truly wanted, but because it felt more predictable and comfortable.
But as I’ve gotten older, my perspective on risk has started to shift. I’ve realized that avoiding risk comes with its own cost: missed opportunities, regret, and staying stuck. The fear doesn’t fully go away, but I’ve learned to question it instead of letting it decide for me. Read More>>

Risk is the difference between working for yourself or working for others. We chose to work for ourselves, and it was the biggest risk of our lives. Still is. Read More>>

Your level of success will be determined by one thing… how good you are at decision making.
And there are two things one needs to understand and be fully aware of, if they want to become a good decision maker: Time and Risk.
Both resources are always present. And both are perceived differently by every unique individual. Read More>>

Taking risks comes a bit naturally to me. Once I’ve taken the time to thoroughly think things through and weigh the pros and cons, I usually just go for it. I believe that if you don’t try, you’ll never know and if you do try, you’ll either succeed or learn something valuable. That mindset has shaped both my personal life and my career. Some of the most meaningful opportunities I’ve had came from taking a leap of faith, even when the outcome wasn’t guaranteed. For me, risk isn’t about recklessness, it’s about growth, courage, and trusting yourself to figure it out either way. Read More>>

Being a freelance musician is a career filled with uncertainty. It is quite stressful, has longer hours than most people think, and requires a lot of planning and commitment. Almost everyday, the most prevalent thought in the back of my mind is, “Where is my next gig going to come from, and how can I get another after that?”. I’m sure any other full-time musician will read this and agree. So why do it? Well. I’ve done the 9-5pm office job. I was making good money doing that. I taught a small amount on the side, and gigged on weekends here and there. I was very unhappy though. I couldn’t stand it. Read More>>

If you had asked younger me about risk, I probably would have launched into a list of very specific worst-case scenarios: choking on a sandwich, escalator malfunctions, tragic bus crashes. I was a pretty anxious kid. My brain often confused possibility with probability, and every risk felt like a direct invitation for disaster. That tendency ramped up after a sudden loss in childhood, but thankfully my parents got me into therapy early, where I started learning how to challenge cognitive distortions and do exposure work. Read More>>

We both had stable rewarding Chef positions in Breckenridge but decided we wanted to take a risk at self employment. It was risky but we have no regrets. Work/life balance is important and we now have that, for the most part. No risks; no rewards! Read More>>
