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.

Sam Pagan

The biggest risk I’ve taken in my career was declining a job offer to start my own business. After finishing my contract at Nickelodeon Animation Studios in 2022, I had a job offer from an animation studio in Vancouver. But I had to leave Los Angeles behind, and that’s when I stopped to think. I questioned the direction my life was taking. Did I want to keep moving from one city to another? Why couldn’t I control where I lived? A few hours later, I called and canceled my job offer. Read more>>

Sharon Mayo

I blew up my life and started over at 42. In 2017, I was an overachieving people pleaser who didn’t know when to stop. I was running the Media Management department at HBO and to save costs (and to help the company), I would continue to work at home until midnight, go to bed, wake up at 6am and start getting ready for work. Then I would get to work, work until 6pm or 7pm, get home, then do more work again until midnight. Read more>>

Joenal Peterson

I started the brand as the result of my big time move from California to the East Coast! The scarce nature and grasses here in the east coast cities inspired this entire idea! I knew I would be nature- deprived moving here but I knew that if I wanted my career to blossom to its new stages, I would need to do something I had never done before. I would need to push my own limitations, self doubt and procrastination beyond its threshold to challenge myself to authentically become who I am supposed to be! I had dropped out of fashion school 6 years prior to my move, so there was always that looming voice saying , “you aren’t qualified” influencing what we call, imposter syndrome. Read more>>

Ashley Gonzales

The biggest risk I have ever taken was making the decision to start my own business. I have worked in the medical field for over a decade, with experience in many different specialties. I have loved each position I held. I learned, I grew, and I used my experience to do more. I always knew I wanted to have my own business, for sure it was always to take care of others in some way. When I started Bodycure, I was working with an amazing clinic, great co-workers and I loved my patients. But still I felt like I was capable of doing more. I start Bodycure in 2022, doing mobile house visits for post op care a couple times a week. I’d work my clinical position, then in the evening I’d go see clients at their house. I used all my time outside of work to market, visit clientele and really poured into getting my services known. About a year in, I took the biggest risk of my life. I left the comfort and security of the clinic where I loved to work, to take on Bodycure full time. This risk wouldn’t have been an option without the support of my family, friends and colleagues. Thankfully with word-of-mouth recommendations and referrals my schedule began to fill. Read more>>

§in

I appreciate the opportunity to interview with y’all. I go by §in, or SSIN. I don’t care which way you spell it. I’ve been doing music professionally for 13 years. I figured out real quick that being a musician, from my perspective, is, at its core, nothing more than a series of taking risks. Outside of writing music, I’m putting a good amount of energy into planning ways to bring live music to DIY places that corporations can’t control. In early 2020 (amazing timing) I started the band I’m singing in now. I feel like the story of our first show is a perfect example of the risks I had to take to make part of my vision a reality. Read more>>

Jaqueline Sanchez

If my younger self were to ask if I’m where I thought I’d be as an adult, I think id be shocked. I envisioned a career in the entertainment industry, managing large productions for famous artists. However, a severe car accident changed everything, leaving me unable to walk for a time. When I was ready to return to work, I couldn’t go back to my previous routine, so I took a leap of faith into a completely unfamiliar field. This unexpected shift turned out to be a blessing in disguise, allowing me to grow and positively impact many lives along the way. Being in the dental field has been my biggest challenge Read more>>

Cassandra Kouremenos

I believe that at the foundation of every creative act is an artist taking a risk. I used to think that taking a risk was an isolated event that would come about at the precipice of a bigger life decision. I realize now that risk-taking is part of the creative lifestyle. In my experience, risk-taking happens multiple times a day: every time I choose an alternate way home, or every time I experiment with a new sound or writing style in the studio, or every time I improvise with recipes for dinner. Every time anyone dares to entertain a possibility outside of what they can predict with certainty is an opportunity to experience the gifts that come with that risk. Read more>>

Día Vail

At 19, I made the bold decision to move to New York and pursue my dreams of a music career, completely bypassing the traditional college route. It was a risk, but I knew deep down that this path was meant for me. The journey has been anything but easy—filled with both exhilarating highs and challenging lows. There were moments of doubt, times when I questioned whether I’d made the right decision, but my passion for music kept pushing me forward. Read more>>

Madison Flintz

Quitting a full-time steady job to chase my dreams and step out on my own was a scary risk to take. I knew I wanted more. I wanted more than a job in one location with no real opportunity to grow. I wanted to do more than work in a retail store that only skimmed the surface of what I wanted to do. I wanted more than the corporate life with the ladder that seemed to lead to yes, a steady income, but a life that didn’t produce my dreams becoming a reality. I wanted more flexibility and the opportunity to connect with my creative side. I wanted to help people more. To help those who didn’t feel comfortable in their own homes and sought out someone to help them create that comfort and peace. I prayed about it, sought out support and confirmation from those who love me and want me to succeed, and made the leap. I quit my job with one potential client and a whole lot of prayer. Read more>>

Kirsten Pursell

I was COVID cleaning in the summer of 2021 when one of my diaries fell out of the cabinet. I must have put it there years prior. It fell open to a page from when I was seventeen. I had blocked the depth of that memory. Next to the diary was a journal of poetry and a poem I had written on the same date as the page my diary fell open to. It was about my first love. I had been encouraged to write my memoir over the years, but I wasn’t sure what that would look like. At that moment, I had the concept: I would take all my diaries, journals, letters, and poetry and tell my story in my own words as I lived it in those moments. I didn’t know if anyone would be interested or care, but I believed there were enough people who would be interested in my coming-of-age story: Being a top athlete; Losing my identity; Contemplating my life’s worth; Falling in love; Making huge life decisions; Wondering about parents and friendships. Read more>>

Cheka Shining

I saw the need and I have gone through so many trials and tribulations that I decided to be a coach, no one’s life is perfect, and we all make mistakes, but we should be loved the right way, and it starts with one self, you gotta look deep inside and know that are worthy to be loved the right way. Read more>>

Chris Rodriguez

The biggest risks I’ve taken in my life revolve around leaving places, roles, and organizations when things are going well. When my wife and I decided to leave Tulsa, Oklahoma, my wife was a nurse, and I was a banker. She had grown up in Oklahoma and wanted a change of scene. She asked me if I wanted to travel the country with her while she did a travel nursing contract. I hated my job and had no prospects for work, but I was ready for change. Read more>>

Scott Manichanh

One of the biggest risk I took was a taking a chance on myself, and investing into my skills and craft taking what little money I had to put back into studio equipment a microphone, head phones, studio speakers, interface and even building a sound proof booth. Every day I would sit in the studio and just dibble and dabble with the equipment to learn the gow and what’s of recording, mixing, mastering and would let local artist record just so I would have material to work with, and after 10 hours at minimum I finally thought my skills were polished enough to charge for my skills, every since then I just kept on developing and made a living off my talent, probably 1 of the best investment I ever made by taking a chance on myself Read more>>

Mayra Reyes

In 2011, I learned about a practice from India called Laughter Yoga and after doing research, I learned that in my area people were not doing this practice. I attempted to connect with the only person that was registered on the main website, and as of now, he hasn’t responded to my messages. Then, I decided to sign up to attend a Certified Laughter Yoga Leader Training in Dallas, Texas. After completing this training, I scheduled my first community session and got about 12 people to participate. People were confused with what I was doing, and I would continually go back to my notes to review what this practice was since I was very new to it. I was told by people very close to me to stop doing this since it was additional duties to my Counselor role. Read more>>

Chef Felipe Cuevas

I believe that one of the biggest mistakes in life is being comfortable with the version of yourself that you are not happy with or knowing that you are capable of greatness and still deciding to settle and not push yourself to take that risk that’s keeping you from becoming great. Read more>>

Darl Schaaff

relocated,purchased a historic building in terrible need of repair in Cleveland’s poorest neighborhood completely renovated the building into a private art museum and full theater ambition to create new art, develop programs not yet happening and transform the neighborhood Read more>>

Robert Lewis

In 2023, the company I worked for reorganized and I had to make a decision to either say with the company or leave. I could stay with a company at a job I loathed, get abused by customers and felt unappreciated at or I could leave and find my fortune elsewhere. It wasn’t a hard decision. It was a scary one, but not a hard one. I’ve always been putting my dreams on hold, either for other people or responsibilities. It was time for me to live my dream and life. It was time I took a risk on myself. Read more>>

Susana Butler

The first time I sang live with a jazz combo, was at a Wednesday night jazz jam at Apres Diem in mid-town Atlanta. I had been meeting up with friends at jams around the city for the better part of a year, just to listen and enjoy the music. As I started making friends in the jazz scene, I found everyone so encouraging and supportive of each other. It seemed that whenever I was introduced to someone, they would ask if I was a musician and I would respond with a “No, I haven’t sung or played an instrument since I was in college” or something to that effect, and then they would tell me that I should give it a try. Read more>>

Rachel Samples

I took a risk leaving a full-time career in advertising to create comedic/sketch videos full-time. You know, just a cute little change from a 9-5, very defined creative director path to a high risk, super unknown path as a content creator. It had always been a passion/hobby of mine over the years – think music videos with friends in high school to making quick TikToks in-between work calls during the pandemic. I love it, but I felt ike the traditional path was what I was “supposed to do.” Videos and “creative time” was just a nice-to-have. It wasn’t until the pandemic and getting some traction on videos that I realized – this could be THE THING. I can try to be consistent and make this THE THING. It started slowly – getting branded opportunities while I was working full-time – and finally it got to what I like to call me “shit or get off the pot moment.” Read more>>

Erica Ly

I made the decision to compete in my very first pageant at 18 years old. My decision was definitely a huge risk since had never had an interest in doing a pageant before. In fact I had some pretty negative assumptions going into my first pageant. At this point I was finishing up high school and I was getting ready for the next phase of life. Little did I know, this decision would ultimately shape my life for the foreseeable future. Read more>>

Alex Bertola

I took the risk of making a living from my passion. But it was a necessary risk because I couldn’t see myself thriving in any other field than music. Although I dreamed of dedicating my professional life to it, I initially started my higher education in France at a business school before daring to take a complete 180-degree turn. Embarking on an artistic career involves a significant amount of uncertainty. Talent and hard work are, of course, essential, but luck also plays a role. While it’s possible to create your own opportunities, there’s still a strong element of chance that determines whether it will work out or not. Being in the right place at the right time, meeting the right people, and working on a project that turns into a huge success—these are not things that follow a traditional career plan. Read more>>

Nika Spencer

I had my first child in 2019 and returned to work 4 months after my maternity leave. I returned to the same cubicle in the same position with the same office politics that had been there before I left. I, however, was not the same. My life had a new purpose as a mother, and while I wanted (and needed) to continue working, I wanted to make sure that my professional endeavors were truly fulfilling and worth the time spent away from my daughter. Read more>>

Jacqueline Torto

I have been taking risks for as long as I can remember. My life is a series of risks taken — A plethora of what-if’s — A sea of trials and error, I think you get the picture. I am a risk taker — Of all the risks I have taken in my life, I would love to share the story of how I decided to pursue photography and creative direction in one of the most competitive industry as a self-taught artist. Read more>>

Dominique Chapman

Hi, my name is Dominique, but you can call me Dom. That’s what my friends call me. I’m a San Diego native, born and raised, and like a lot of young people searching for meaning and excitement, I left home for a while. After moving to Oregon for college, I then chased a dream in New York City, diving into the edgy art and dance scene. But, like so many others, COVID-19 changed everything, and I found myself back in San Diego, reflecting on what I truly wanted out of life. Read more>>

Julia Kushner

I had started my career in the arts as soon as I graduated art school, working in various galleries, agencies, and consulting firms. I gained experience in the different art markets such as public art, residential, commercial and hospitality. With each experience, I built new knowledge, skills, and trusted relationships that I knew would benefit me wherever I would go. After a decade of working for different businesses, curating and consulting artwork for collectors, designers, developers, and public spaces all around the world, I was confident enough in myself to begin my own venture and say goodbye to the stable bi-weekly paycheck many creatives would dream of having. I was ready to 100 % invest in myself and all the hard work that I had put in thus far. Read more>>

Jennie Spillane

The biggest risk I ever took was to quit my secure corporate job, sell everything I owned and moved to the most remote chain of islands in the world (Hawaii). I know poor me I moved to paradise, but you’d be surprised at how challenging this move actually was. I was at my former job for 8 years and I loved it, but I reached a ceiling. I grew up in a small town in Colorado, so I was land locked most of my life and I was deathly afraid of the ocean because of my little exposure to it. So, once it was decided that I was no longer growing at my job as a marketing manager of a ski resort in Colorado, I decided to face my biggest fear – the ocean. Read more>>

Max Blakesberg

I’d say the biggest risk I ever took when it comes to my photography career was actually deciding to pursue it as a full-time career, rather than something I just did for fun. As of today (October 2024), I’ve been taking photos for nearly 15 years—over half of my life. Mentally, I think I always knew that photography was my path. Initially, I was worried about losing my creative spark as well as the sense of fulfillment I got every time I picked up my camera. The idea of photography being my means of survival, something tied to paying bills and making ends meet, was daunting. I was terrified that my love for it might wither under the weight of financial pressure, deadlines, and the never-ending hustle to find clients. Read more>>

Nicole Lukas

The Story of Taking the Leap into My Photography Business: For years, I dreamed of creating a photography business that reflected my wild, free-spirited nature and my passion for supporting women on their personal journeys. I wanted to capture goddess photoshoots, holistic business owners, and the soulful moments of retreats and workshops, but that dream felt like a distant “someday.” I knew deep down that I wanted to live in alignment with my values—freedom, connection, healing, and creativity—but there was always fear holding me back. What if it didn’t work? What if I couldn’t make enough money? What if following my heart wasn’t enough? Read more>>