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.

Libby Schmidtman | Event Host, LibBingo LLC

Risk-taking has had a huge role in my professional life! Ever since getting laid off in 2020, that’s no longer something I fear. Each new job I’ve had since then, I’ve approached with a mentality of “What do I have to lose?” And I’ve found that putting myself out there and taking chances has been endlessly rewarding. I even had another layoff in 2022, that I ended up shrugging off with an appreciation for the new skills learned in that role. Read more>>

Simon Shackleton | Music Producer and Creative Artist

As a music producer, risk is omnipresent in my life (sometimes too much so!). There’s very little financial certainty in releasing art that you believe in into the world, but there is a compelling creative certainty, which is that my work continues to resonate and give meaning to people – and that’s important. Read more>>

Logan Tyler | Founder of Basecamp Ouray Mountain Guides

As Logan Tyler, co-owner and founder of Basecamp Ouray Mountain Guides, I’ve built my life and career on the calculated risks that come with climbing, entrepreneurship, and pushing boundaries. Risk, for me, is an inherent part of growth—whether it’s navigating the exposed terrain of the Gold Mountain Via Ferrata or making bold moves to grow my business in Ouray, Colorado. Read more>>

Hannah Gleditsch | Mother, wife, former police office, small business owner

Before I became the owner of Colorado Coffee Company I spent nearly 8 years working in law enforcement. Through my time as a police officer risk was always in the back of my mind. There are many risking things about the job itself but it was also part of territory and you just knew that going into it. I think things started to shift for me when I had kids and the risk started to feel a little bit heavier. In 2022 I was diagnosed with a non curable disease that ended up forcing me to medically retire from my sworn position with the police department. Going through that process and diagnosis really opened my heart and my eyes to a whole new, very vulnerable, side of life.  Read more>>

James Lane | Podcast, Writer, Musician.

It’s unlikely without risk, whatever we want or desire likely requires a little bit of risk to make happen. Last year, I created a group chat called Club Risk. While it’s partially a space for random life updates and funny memes. The main purpose is for people to share stories of risks they’ve taken. Every time I check in, I feel inspired to pursue my passions and go the extra mile. A quote I heard a few years ago that stuck with me is “I rather regret something I did than didn’t do.”. I try to apply that quote to my life on a fair regular basis and it’s brought me to some incredible places. Imagine for a moment, you have the chance to have an amazing experience of something you know you would enjoy, but the fear creeps in if you should do it because of judgement, failure, or possibly the unknown. Read more>>