The chapters in our stories are often marked by wins and losses. Getting a new job, getting fired. Getting a life-threatening medical diagnosis, beating it and getting a clean bill of health. Too often, due to a societal expectation of modesty and humility we are discouraged from talking about the risks we’ve taken that led to those ups and downs – because often those risks draw attention to how we are responsible for the outcomes – positive or negative. But those risks matter. Those stories matter. We asked some brilliant entrepreneurs, artists, creatives, and leaders to tell us those stories – the stories of the risks they’ve taken, and we’ve shared them with you below.

Amber Hoover

Throughout my early education and college years, I knew I wanted a secure job with a stable salary and a guaranteed paycheck. I was never attracted to commission-based roles. I wanted certainty in my income and financial future. Read more>>

Brooke Patton

My journey beautifully illustrates the transformative power of embracing risk, especially when it intersects with the deeply personal realm of creativity and artistic expression. Read more>>

Nathalie Guenther

I’ve been in the fitness industry since 2012. I went into that field because I have personally gained a lot from what it had to offer. I always felt my best when I was moving my body and doing fun things like playing sports, racing friends, and climbing over fences just for the heck of it. Read more>>

Rosie Coca

Back in 2020, I purchased an ice cream truck business from someone who was moving out of state. I was a stay at home mom of 2 and had no idea on how to run an ice cream truck business or even drive a big box truck. Read more>>

Peach & Quiet

Shortly after the Covid pandemic hit, we saw a social media post from renowned Nashville recording artist and producer, Steve Dawson, offering his services in a ‘new’ and streamlined approach of ‘remote recording’ of single songs, using his crew of ace studio musicians, who were located in various widely spread out locations, across North America. Read more>>

Sean Dupiano

Senior year second semester. Finishing school with a fully stacked resume due to all the experiences bd worked I’ve put in these past 4-5 years. I had to choose between applying for a full time job or full sending my own business.  Read more>>

Livia Chaves

I’ve always been a very resilient, determined, dedicated person who always finished a task assigned to me – even if at the expense of my own health. Read more>>

Carla Khair

It feels like my life has been a sequence of risk-taking events, and when times are tough, I look back at steps already taken to re-energize myself and keep going. Read more>>

Seamos Impertinentes

When starting this podcast there were many things that worried us. Can we handle this? Will anyone listen to us? What if it results in a failed project? Eventually, there were many things that we couldn’t know until we decided, so we said fuck it, and started the project. Read more>>

Mark Diaz

The Risks for me have come in all sizes related to my art. The first risk i took came at young age when i entered my first Art contest. Looking back it was a big risk but didn’t realize the magnitude of it until i showed up to do it. Read more>>

Tamara Dotson

Let me tell you about when and why I took the risk of being an entrepreneur and working for myself and how it has been the best experience of my life! Read more>>

Sameh Khalatbari

Taking risks has never been my forte, but one particular leap stands out, altering the trajectory of my artistic career. Let me share the story of that pivotal risk. Read more>>

Daniel Madden

In 2020, I reached a pivotal moment in my career as a youth pastor. After nearly a decade in the role, I realized I needed a change. Read more>>

Darina Eid

As a child, the first memory I have of a thought of my own was: “Never stop wanting it, never give up.” This inner voice became my drive and companion, guiding me through the challenges of growing up with dreams of becoming a dancer and actress in a culture where such ambitions were often dismissed. Read more>>

Lauren Casassa

Risk taking is something so essential to being an artist. “Take risks!!” I’ve heard this my entire art career. I believe it to be true, taking risks is valuable in many ways. Read more>>

Bonnie Beauchamp Cooke

With two young children, leaving the corporate world of advertising to pursue a full time career as an artist was one of the most rewarding yet frightening decisions I have ever made. Read more>>

Surabhi Singh

Work. Appreciation. Relevant Opportunity. Gut Instinct. I had it all but it turned out to be a risky combination, atleast for me and I will tell you why. Read more>>

Caden Butera

Like all creative professions, the film industry comes with a near paradoxical conundrum: Make an objectively fair profit on products with a subjective value. In other words, in art there is no clear right/wrong answer. Read more>>

Maria Mor

Recently I was telling some friends that my life has all been about taking risks. I described the image of myself standing at the precipice of a cliff jumping off into the abyss. As I get older I find that the cliffs get higher and the jumps get deeper! Read more>>

Carlos Jimenez

Moving to the US at the age of 16 by myself. Read more>>

Kristine Reiner

Risk taking is something I’ve always done. I grew up in a rural town in South Dakota, during that time I worked several jobs. One of the most formative job experiences I had was working in long term care, a community of residents who transitioned to communal living in their later stages of life. Read more>>

Taron Lexton

Probably the biggest risk of my career was in 2019, filming a total solar eclipse for a feature film. It was kind of insane. It was our first day on the movie, and the rule of thumb is, you always start with something easy on the first day, to let the crew find their feet and get a win under you. Read more>>

Chiany Dri

I’m a natural risk taker. I’ve always been interested in what life looks like outside of the confines of expectation. However, I would say that the biggest and scariest risk I’ve taken is jumping head first into starting a business. Read more>>

Olivia The Creative

I am a born risk-taker. I believe firmly that if you leap, the net will appear; of course if you are doing so responsibly and with good intentions. Read more>>

Amy Mattila

Since 2011 I’ve been working in wellness and health coaching. My career has covered health insurance firms, financial institutions, primary care in clinical settings, worksite and employee wellness, and a digital health start-up. Read more>>

Kayla Mohammadi

I think anyone who goes into the arts is taking a risk. There are easier paths to making money and having a career in the corporate world as one example. Read more>>

Jessica Obando

My journey has been one of transformation and risk-taking, that begins working as a stay-at mom and dance teacher and leading to into a deep dive into psychology. Read more>>

Alexis Martinez

Back in August of 2023 I moved from Arizona to Arkansas with my husband. He is a Chef, Hiphop Writer/performer, and Social Worker. Read more>>

Karina Menali

I picked up a fridge magnet once that had written on it, “Life begins at the end of your comfort zone.” That motto is not for everyone. Read more>>

Drey Skonie

Back in 2007, I auditioned for Making The Band 4. For me, it was a chance to see if I have what it takes to compete in the industry. Read more>>

Gabe Alexander

I took a risk on myself at 28 years old in 2023 when I left my regular job and decided to pursue my entrepreneurial career path full time and become a professional basketball as a way to survive and thrive as a young adult , without the security and assurance of a 40-hour a week income. Read more>>

Joy Perez

I am of Chamorro and Filipino descent, and growing up Pasifika, our culture was deeply influenced by Catholicism. Embracing my authentic self as a queer, polyamorous woman was a significant risk for me. Read more>>

Dave Knox

In 2007, I was debating what I wanted as the next steps in my career. I had been promoted to Brand Manager at Procter & Gamble at the age of 26 with the opportunity to work on the Customer Team for Walmart, our largest retail partner. Read more>>

Nyseim Tucker

The field I’m in is always a risk, combat sports is such a danger, we risk our lives every time we step into the ring. I take this risk because I feel as tho the award in the end is bigger then the fear or the risk I’m taking. Read more>>