Tony Robbins says the #1 human need is certainty, but do you know what the second need is? It’s uncertainty. This tug of war between the competing needs of safety and risk are at the heart of so many dilemmas we face in life and for most folks the goal isn’t to eliminate risk – rather it’s to understand this core human need. In our view, the best way to understand or learn is through stories and so we’ve asked some very talented entrepreneurs and creatives to tell us the stories behind some of the risks they’ve taken.

Jesamyn Angelica

My life took a monumental turn when I decided that it was time to begin Sisterhood of the Moon, a Goddess community focused on connection, empowerment, and authenticity. This decision wasn’t made on a whim or based in a desire for power; it was a calling that I had been hearing for a long time, arising from deep within my soul. I knew, though, that following that calling meant taking a monumental risk, leaving behind the security and comfort of my established life and heading out into the wild unknown. Before making this tremendous shift, I was leading a life that, from a distance, probably looked quite stable and rather “normal” by Northern California standards: I had a career in the New York publishing industry, a vibrant social group, and a ritual circle I served weekly. My priestess work was primarily “under the radar” during this time, and I often took comfort in the mostly hidden nature of my spiritual path. Read more>>

Amelia Bartlett

At the beginning of 2024, I left the investment business I’d co-founded to pursue filmmaking full-time. I’d worked the last half a year doing production on the side, seeing opportunities if I’d only had more time. My vision was to create a media production company that, rather than focusing on producing commercials for companies, would produce films, television, and documentaries that elevated regional stories and voices. I assembled a team of co-producers, including Stephanie Hong and Kate Szekely, and we began to form a network — crucial to media production — from which we could hire crew members and cast for projects. As with any business, this was a huge bet, not just on creative capacity but whether or not what we imagined would find a place in the market. Read more>>

Nancy Evans Doede

I would never have become a professional modern dancer, or choreographer, or Artistic Director of my own modern dance company if I hadn’t taken a risk. To begin with, I always loved dance. As a child, I was enrolled in ballet classes because I needed to correct foot issues. I fell in love with ballet, and wanted to “be” a ballerina when I grew up. Problematically, for me, I did grow up, and up, and up. When I was in high school I was 5’8″ tall, and at that time in the ballet world, had no hope of being that ballerina, at least, not professionally. I changed my direction, and studied theatre. In college I reacquainted myself with modern dance while pursuing an acting/directing degree, and fell back in love with dance – this time, modern dance. Read more>>

Suanna Lynn

When I decided to move to Nashville from Chicago, I knew it was going to be a big risk. I was leaving a huge group of friends and really encouraging community, my family was just a state over, and I had a secure job in public relations and marketing and I was thriving. But something was missing. I didn’t have my people as it related to writing music. I of course had other musician friends, but the passion I had for writing my own music started to take over everything I thought about and I knew I needed an entire community of people who were as obsessed with original music as I was. I was writing alone in my apartment in Chicago and I was a good writer. But I knew I’d never be a great writer unless I challenged myself and made music with people who were much better than me. Read more>>

Devin Baggett

A major risk in my life was leaving behind a stable career at Apple to pursue my passion for music full-time. I had been working for Apple as a software developer while producing music on the side, but as my skills and connections grew, I felt a stronger pull toward dedicating myself to music. It wasn’t an easy decision—there’s a lot of security in tech, and I had bills to pay—but I knew that if I didn’t take the leap, I’d always wonder “what if.” The turning point came after I released a few tracks that started gaining traction, including my collaboration with Daniel Pinho on the track “Athon,” which was featured on Armin van Buuren’s A State of Trance. The positive feedback led to more collaboration requests, and I quickly realized that balancing a 9-to-5 with music wasn’t sustainable for the growth I wanted. So, after being laid off from Apple for the second time, I turned down another job offer with a new team at the company and decided to fully commit to my music career. Read more>>

Blake Laitner

Sometimes in life, we have a choice to make: keep heading down the same road or take a chance and head down the beaten path. My chosen path is film. I decided to attend a film vocational school called Film Connections when I found out that it wasn’t a requirement to make a film in film school! I just needed to write a script and come to LA to pitch to a producer. I had to take a risk and take matters into my own hands because I couldn’t go to film school and not make a film. So, I produced my first short film called “The American Dream,” which was selected by a few film festivals. The standout film festival for me was the American Chinese Film Festival, but I thought only got accepted to use my film as propaganda. My biggest fan of my work, my dad Morton Laitner, wrote a book called “A Hebraic Obsession” and wanted a short film to market his book. Read more>>

Keith Barbour

The risk I took that changed my life: As a D1 athlete, I spent years training, competing, and pushing myself to the limit, but when graduation rolled around, I faced a hard truth—I didn’t believe I had what it took to go pro. Lack of self-belief clouded my vision of continuing down the path I had known for so long. With no clear future in sports, I did what many do—I settled  into a 9-5 job as a security analyst. It wasn’t the dream, but it was safe. Stability was something I could count on, but deep down, I knew I wanted more. There was this creative side of me that longed to come alive, and I felt the urge to express my thoughts in ways I had never explored before. That’s when I decided to take a risk—one that seemed completely out of my realm as a former athlete. I decided to write a book. Read more>>

Thomas Fowler

The pandemic really turned my regular job situation upside down. My bosses tried everything they could to keep me on but so much advertising shut down. As a result, I was laid off in 2020. I found a couple other ad agency jobs but wasn’t overly happy. History repeated itself and I lost another job in 2023. Two jobs were lost in less than 3 years. The second time around, I knew I couldn’t keep going as things were. I decided to take a risk. That was when I decided to make my own short film. I had the feature script written but knew from festival networking shorts were the best way to get a feature film greenlit. Read more>>

Josefina Jimenez

May 3rd 2019, a day that changed my life forever! I was 37 weeks pregnant with my 2nd child Bruno, when unexpectedly in the span of 8 hours(while I was sleeping) the worst thing imagineable occurred. The next day I show up to the hospital as I had no fetal movement for hours and was given the gut wrenching life altering news that my son was dead. A shock like no other, a pain that will never subside, you only learn to live with the pain and accept the grief of what your life “would’ve been”. This left me with an emptiness inside that felt like I was dying slowly every single moment of my life, to be honest I would have preferred to than to experience that type of pain. Read more>>

Alison Hild

Prior to becoming a Clinical Psychotherapist, I worked in the music industry for nearly a decade. My career in music began at an independent record label in the Hudson Valley (New York State). While there, I had the opportunity to wear many different hats but primarily worked in promoting our artists for radio play. When I moved out to Los Angeles in 2014, I was hired by a major TV studio where I had the opportunity to music supervise and clear music for use in our projects. I loved my time working in music and in the entertainment industry. I found the relational aspects of working with others to be particularly fulfilling, especially developing friendships with creative professionals and helping musicians navigate their careers. Read more>>

Dr. Dequies Lanier

Taking a risk for some comes naturally, those kinds of people are wired for change, innovation, excitement, and the thrill of experiencing constant adventure. I’d say that I like variety in my work life. In my personal life, I love a good bit of adventure and surprises too. However, professionally I am more conscientious and methodical. I like plans, I like strategizing for quite a while. Information makes me feel safe and secure. If someone is trying to convince me to do something I need time to do my research and understand the process. I need time to feel my way through what feels authentic for me. That said, risk-taking is required when you start a business. If you aren’t willing to take risks, you aren’t willing to be a business owner. Read more>>