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.

Frankie Ellie Sklar

I believe in taking risks, even when they scare me—and they almost always do. My life has been shaped by bold leaps into the unknown, starting nearly 15 years ago when I left law school despite having no clear plan ahead. Instead, I followed a faint hit of intuition, what I call a ‘glimmer’—toward a life that felt more aligned. Read More>>

Toni Cacioppo

Risk-taking is essential for growth—both personally and professionally. If you never take a chance, you’ll never know what could have been. Staying in your comfort zone may feel safe, but it often leads to stagnation. Change and discomfort are where real learning happens. Read More>>

 Candi Hegenbart

Taking risks in life and career, especially as a “tax hustler” (someone grinding hard in the tax industry, whether through tax preparation, consulting, or building a firm), is all about calculated moves. In this field, risks can mean expanding your client base, offering new financial services, or stepping into entrepreneurial ventures like starting your own tax business. Read More>>

Michael Waldron

No one that has ever been successful has become successful by being comfortable in where they are at. I have taken a ton of risks throughout my 25 year career. Some of the risks I have been forced into by changes or directions I was going, but all of the risks have turned out for the better. I look at risks & changes as a chance to reinvent myself & it gives me so much drive to be successful in that venture. Read More>>

Neena Vigil

Risk taking is absolutely necessary.. I cannot emphasize this enough. You NEED risk to strengthen your intuition, know how limitless you are, push your bounds & to grow past fears you may have unconsciously. Anything feels like a risk when you’re in your comfort zone. TAKE MORE RISKS. Read More>>

Abigail Aunspaw

I wish I would have known going into it all that failure and risk taking is actually a major and huge part of your overall success and continued learning process needed to run a successful business over a long period of time. Most businesses fail within a few years. Its takes alot of confidence and risk to keep the marketing techniques going and being able to pivot at any and everything that is thrown your way, good or bad, at any time. Read More>>

Lily Grace Nolan

Risk is Its Own Reward
Whether it’s a win or a flop, I believe in taking the leap. Risk, at its core, is growth—every bold move I’ve made has shaped my career, expanded my creativity, and deepened my resilience. Read More>>

Zack Kopp

I grew up wanting to be a writer or a rockstar and expecting it to work somehow. It wasn’t realistic but I’m glad I took that risk. I ghost wrote a few books for Jim Morrison’s brother-in-law after writing an article about Jim possibly faking his death. Paul Krassner and Dan Fante became my pen pals after I wrote to them, may God rest them both. It all started when I co-edited a zine in college and grad school and decided to reach out to people and start interviewing them instead of being too shy or thinking about the likelihood of response to my emails. Read More>>

Joe Bissonnette

I’ve always been attracted to danger. I love trad climbing, mountain biking, solo international travel, and exposed scrambles. When I’m living dangerously, I’m keenly aware that my days are numbered and there’s something magical about embracing that. It makes you live to the fullest. This hunger for danger has also really impacted my career and opened up a lot of doors. I’ve worked around live nuclear reactors; I’ve spent years working in Antarctica, I’ve worked on cell towers, and I’ve worked in a wood pellet plant that was highly combustible.  Read More>>

Felipe Proaño

The mountaineering and climbing lifestyle have taught me some powerful tenets. I understand risk is a part of life and of nature, and I feel privileged to have acquired these skills to analyze risk, embrace it and move forward. These tenets are to be resilient, to have an indefatigable spirit, to be tenacious and above all it has taught me to be compassionate. Read More>>

Leslie Heins And Lisa Cook

As two seasoned event planners for close to 40 years, (before there was even a category of event planning), we found ourselves cleaning forks at 2 AM after a hugely successful wedding. I turned to my partner Lisa and said, “I’m getting too old for this and she agreed, but at the time, we didn’t act on it. After a very successful year, we decided to reward ourselves with a week’s vacation at Canyon Ranch. While walking through a labyrinth maze, we stumbled upon a rock inscribed with the words “It’s never too late.” It peaked our interest so, we decided to attend a class with the same theme. I noticed Lisa’s wheels were turning. Read More>>

Steven Darnielle

Someone once told me that “life is like a game of chess” and every move we make in life must be carefully calculated. In life, we have to constantly think 3,4,5,6,7 moves ahead. Sometimes when we make these moves, they have immediate impact or long lasting consequences. However, as long as we refuse to quit and not go into “checkmate”, we will eventually get to our desired destination. If we think about it, we take risks all the time without even realizing it. Just to make it to work everyday, we get behind the wheel of a car knowing that the risk of getting into an accident exists.  Read More>>

Kimberly Abbs

Taking risks, especially when it’s tied to something you’re passionate about, requires a lot of courage. It’s so easy to get caught up in fear of judgment or failure, but without taking that leap, you’ll always wonder what could have been.

It took me a long time to find the courage to step forward as an artist and creator. I had to focus deeply on my mindset and truly believe in myself — that there’s a place for me in the market and I have something unique to offer. Read More>>

Steven Sikhampheng

Risk was one of the main factors that built my career. Risking dropping out of college to become a chef to risking packing whatever I can pack in my car and moved to Colorado. Taking a risk can also equal growth. There were a few times in my career that I felt stagnant and felt I had more to explore. As the culinary industry grew in innovation, I felt like I was being left behind. I would say it was due to me being comfortable with the work I was doing and the money I was making. Opportunity came knocking at the door to see if moving to Denver was the way for my career. Took the risk to drive from Tampa to Denver and it was worth it. Read More>>

Noah Crowley

Looking at risk, I’ve always had a naturally high tolerance for it. My approach isn’t reckless though – it’s calculated. I think about risk as an essential component of growth, and I’ve developed a quick information processing ability that helps me recognize patterns others might miss.

Risk has been central to my journey. At 18, I chose backpacking through Europe over college. That was probably the happiest time of my life and taught me to be comfortable with uncertainty. I literally talked my way out of being held at gunpoint during those travels – talk about a crash course in high-pressure situations! Read More>>