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.
Trisha Gianesin
I’ve always embraced the idea that the possibility of hearing “no” can lead to many more “yeses.” This mindset guided me when I decided to take a significant risk by reaching out to cinematographer Brady Bassette—someone whose work has profoundly inspired me, to see if he would consider coming on as the Cinematographer for an upcoming project, The Travelers Team. Initially, self-doubt held me back. I feared that my inexperience would lead him to dismiss my email. For days, I wrestled with this mental tug-of-war, One part of me insisting that sending it was a foolish notion, while the other part whispered, “But what if it’s not?” Finally, after days of hesitation, I made the decision to hit send. Read more>>
Connie Stowers
Three years ago, I made the decision to detonate a bomb. The target? My entire life. I had carefully constructed a life based on the blueprint that society laid out for me. You know the one: go to school, get a degree, land a job, find a partner, buy a home, have a baby, and ride off into the sunset. But no one tells you what happens after the glass slipper fits, do they? Turns out, you can lose yourself pretty quickly when none of the dreams you’re living are actually your own. Back in 2009, I walked across that graduation stage, proudly clutching my $160K Communications degree, blissfully unaware that it was about as useful as a decorative paperweight. The harsh reality hit when I found myself jobless for months, eventually landing a gig as a Sales Supervisor at a jewelry store, earning a whopping $12 an hour—after commuting two hours each way. Read more>>
Sarah Hunter
In 2021 I took a risk and invested in a pottery wheel. I’d been discouraged from doing so from some individuals as I am considered a “painter” not a “potter”. However, I could not shake the feeling that this was a journey I needed to embark on. This remains today one of the best risks I’ve ever taken. How it started…In January of that year some things were starting to reopen post COVID and I signed up for my first official pottery class. Within the first couple of lessons, I learned that I needed to stay loyal to my left-handed self and throw lefty. After that realization the struggle lessened and I fell in love with the practice. Read more>>
Amber Underwood
I remember it like it was yesterday. Becoming a traveling NICU nurse was my dream. I wanted to save the lives of babies like the nurses that saved my life when I was 3 weeks old. In my limited thinking then, I thought the only way to help save lives was by becoming a nurse. I was wrong. I was a junior in college when I was rejected from nursing school for the 3rd time. I spent that Summer sad and hopeless, trying to make sense of my life and what was next. I had no idea what I was going to do. I’d watch my classmates prepare for their senior year of college, while I was anxious, trying to figure out if I was even going to graduate from college. It was a scary time and it made me question my self-worth. My parents didn’t have the money to send me to school in the first place, and student loan programs and Pell grants were running out. Every day the sun rose I became more anxious. So I did what I only knew to do – I prayed. Read more>>
Elo Copeland
The biggest risk I’ve taken to date is pursuing Stand-Up Comedy! I will say the risk was worth the taking lol. Not only did I have to overcome the fear of public speaking but also making people laugh outside of my family and friends. I’m very proud of myself because it’s been 2 years and I’m still here, sharing stages with great comedians before me and here now. It’s amazing how life brings you to a path you had no idea taking. Read more>>
Jawon Chisholm
I quit driving trucks, with no plan. Just a purpose. I knew my life wasn’t where I wanted it. So I started my buisness with just two clients and over this past two years since quitting I’ve now trained well over 250 people and teams as well. Read more>>
Belinda Picaso
This Business has been a huge risk. I’ve never finished or stuck to something work/career wise, so to me starting my own business was like “WHAT ARE YOU DOING BELINDA?!” I knew that if I started it and went full blown into it I could not back out, I could but starting this was supposed to be something for myself and my family as well. I already am not working and when people hear stay at home mom sometimes its looked at as just being at home all day hanging out so to start this business it was a risk because I am still a stay at home mom, I am having to find balance in doing this business and still being mom at the same time, no taught me anything about this or walked me through any of it so trusting that its going to work and fall into place has been such a challenge but I’d say its all been worth all of it! Read more>>
Ashka Din
One of the biggest risks I’ve taken in my life was leaving my 9-5 job at one of Houston’s most prestigious maternal fetal medicine clinics to become a stay-at-home mom. I had been a sonographer for over 10 years, specializing in high-risk pregnancies, and I loved my work. It was secure, fulfilling, and I had built a strong reputation in my field. But after having my two children, I realized I wanted to be more present in their lives. The pull to be at home with them full-time was strong, but leaving behind a stable career I had spent years building was incredibly daunting. Read more>>
Mireille Nashimoto
There are a few moments of taking risks into the unknown in my life that when I look back, were some of the best decisions I have made. The one I want to highlight is the decision to make the move from the San Francisco Bay Area (where I grew up) to Tucson, AZ 15 years ago. I had just had my 4th baby and she was 3 months old. My partner and I are both from the Bay Area so although we had many family and friends nearby, we had a calling to the desert. We had made several trips to Arizona over the years, exploring different parts of the state. We always loved it, the weather, the beauty of the rawness of the earth, the plants and animals, and pace of life. We always wanted to have the opportunity to find some land where we could experiment with sustainable building and living practices and the reality of trying to do it in the Bay seemed too challenging. So, after baby number 4 was born, I remember feeling this very strong pull to find where we needed to be as a family so that I could establish roots and raise my children. Read more>>
Hillary Van Scoy
I moved to NYC from the UK in March of 2019 without knowing a single person here. I wanted to further my learning and pursuit of sound engineering, and I knew I’d have a far larger set of opportunities if I came to New York. It’s the centre of everything. I had a small amount of money saved up from working cleaning jobs back in Glasgow, a suitcase with a duvet and some clothes in it, and not much else. I had just started working as an engineer’s assistant sporadically the prior year in Glasgow, Scotland after recording on my own for years in a super stripped-back home setup. Read more>>
Ricky Fernandez
I believe deciding in Physical Therapy school that you don’t want to be a full-time physical therapist is always a risk. When I started graduate school, my dream was to work as a physical therapist with high-level athletes or those suffering from chronic low back pain. As a former athlete and physical therapy research enthusiast, I felt called to serve those populations. However, during one of my clinical rotations—which are essentially internships—I quickly realized that full-time physical therapy didn’t align with my expectations. The long hours, lengthy commutes, high patient volumes, and somewhat repetitive nature of the job led to my first experience with burnout. I pulled back from my self-care routines, stopped investing in my professional growth, and started to view patients as numbers rather than people. This was not how I had envisioned my career. Read more>>
Linda Mann
Risk taking for me, is all about exploring the curiosities outside of my comfort zone, with the intent to fill the chapters of my life with possibilities for growth. Some of those curiosities, through many decades, have been about asking myself, “what makes me feel alive”? My answer included skydiving, white water rafting, barrel racing lessons with my horse, ballroom dance lessons, rollerskaking, homeownership & decorating, a career in nursing, teaching health education, being an esthetician & business owner, furniture artist, soap maker, and canvas artist. As common as these endeavors may be, all involved risk taking, My drive to “mush it all in” comes from the realization, at the age of 15, that no day is promised. Backstory on that life lesson was the tragic loss of my dad & sister in a motor vehicle crash. So we can turn tragedy into motivation. Read more>>
Steve Alpert
I am a lifelong painter, beginning when I was 19. I made my living as an independent TV producer/Director for 35 years, all the while I painted on the side. But, when I turned 49 I realized I need to do something different. I had no idea what. “Why don’t you go for the painting,” my wife suggested. I had no idea what she meant, “I mean make paintings and sell them.” That had never occurred to me and I did not know a single artist nor anything about the selling of paintings. Men, if you don’t have a wife who challenges you then you are truly missing out. Read more>>
Natalia Salivia
One of the biggest risks I’ve taken was choosing to step away from competing in track and field during college. Track was a major part of my life from junior high through high school, and my dream was always to run at the collegiate level. I competed in the 400m, hurdles, and relays, and while I loved the sport, I constantly battled anxiety and physical injuries. My knee pain was severe, and I had foot surgery during my sophomore year. But the mental strain was just as tough—daily panic attacks and the pressure to perform made each race more challenging. Read more>>
Liz Oliver
As an artist, in order to grow and to evolve, one must take risks. The biggest risk I have taken would have been when I decided to move to LA from North Carolina. I grew up in Charlotte, and have very fond memories of home. I have loving family, and many lifelong friendships. I was never the one in my circle that people would have imagined leaving for a large, sprawling city across the country. What I did, and what I still do to this day, is follow my curiosity and my intuition. I always knew that I wanted to be an artist. I graduated from Appalachian State with a degree in Art. After I graduated, I worked as a waitress, as I continued to take textile related classes at institutions, such as Penland School of Crafts. I then signed up for a weaving concentration with Amy Putansu at Penland for two months. It was there that I realized I was intrigued by Costume Design. Once I left, I signed up for Post Bachelorette classes at the local university in Charlotte, UNCC, to see if this was a career I wanted to pursue. Read more>>
Kevin Wade
The biggest risk I’ve taken has been moving halfway across the country to peruse my masters in illustration. I graduated with a degree in graphic design back in 2020. I was lucky enough that an internship turned into a job during COVID. As pandemic waned and business picked up I found myself not fully satisfied with doing work for other people and I wanted to learn the skills to bring the stories I want to tell to life. So I applied to grad schools and eventually got into an illustration program in upstate New York. It was quite the shake up from my small hometown in southern Indiana. Read more>>
Christina Moat
My story begins after a divorce. After 7 years as a stay at home parent with some freelance work as a copywriter, I reset the clock on my life and career back to nearly where I started as a young adult. Any one who has experienced divorce, especially with children involved can relate to how life changing that situation is but to also include re-entering the corporate landscape with such a huge gap on your resume certainly adds to an even bigger hurdle to overcome. It took me a few months but I landed an amazing job at Yamaha Financial Services. Sure, it was at a lower level than where I had last left corporate America but to know that I was wanted and valued as a employee again gave me a renewed sense of empowerment I never had before. As the story goes with most corporate entities, nothing good seems to last forever. Major changes had occurred at the top which trickled down and altered the course of the entire company morale. One by one, the best were leaving and I found myself looking to do the same. Read more>>
Kristyn Granahan
I recently saw a post by a woman sharing how she got on a relationship-matching website in her 40s, bought a farmhouse in her early 50s, quit her career in her late 50s, and started an online hustle in her 60s. She called it her four midlife reinvention leaps. When Lyme disease robbed me of my 20s, I felt like I lost so much of my prime. Those should have been the years for fun, exploration, and self-discovery. Instead, I spent half of that time sick in bed, accumulating over $100k in medical bills, while the other half was spent searching for a maintenance level that would allow me to engage with life consistently. I’m grateful for how far I’ve come in my health, and posts like this remind me that many prime years are still ahead. After all, prime is a mindset, not just a number. Read more>>
Jaymi Jai
I found myself at the edge of helplessness. It was an abyss of darkness promising to swallow me whole, and I had two choices – die or die. I could stay at the edge where certainty was promised in the illusion of security. The mask of my false self clutched desperately in my hands to shield me from the pain I was too afraid to own while my soul screamed silently from the cage I held it in. Or, I could jump into the dark unknown and allow the journey of discovery to liberate my heart’s devotion to the wonder of authentic aliveness. Read more>>
Ben Feldman
One of the biggest risks I’ve taken in my career was producing The Flash: Test Run, a fan film based on a character I’ve loved for as long as I can remember. The Flash has always fascinated me—not just for his speed, but for the heart and humanity behind the larger-than-life superhero. I wanted to bring my own version of the character to life, one that felt real and grounded. But as anyone in the industry knows, fan films are tricky, especially when you’re starting out without a big following or resources. Read more>>
Mike James
I am a risk taker that is for sure. My ambition is what got me here 3,000 miles away from where i was born and raised. My biggest risk was coming to Los Angeles to pursue my dream in music and entertainment. I started off as just another kid who loved to make music and write songs about my experiences in life. While all my friends where going off to college and starting families i always wanted more then just that simple basic dream. My first time moving to Los Angeles was in 2011 i was only 21 at the time driving a cross the country with my friends. I call it my trail run because i only lasted a year before i got homesick and lost my vision of why i came there in the first place. Read more>>
Jodie Brown
In February of 2020, I was in a tough place mentally even though I had a successful career behind the chair as an independent hairstylist. I was able to attract clients. I was doing well in my business. But behind the scenes, I was going through some really difficult personal challenges. We were dealing with secondary infertility, my husband had been laid off, and despite my business success, we weren’t doing a great job of managing our money at the time. I was struggling mentally and feeling like everything was kindof hopeless. Read more>>
Joe Tye
After graduating from Stanford with an MBA in 1985, rather than getting a job like all my classmates I started a nonprofit organization called STAT – Stop Teenage Addiction to Tobacco. During my second year I’d done an independent study project on ethics (and the lack thereof) in the tobacco industry. I interview senior industry execs, including inviting one to a class at the biz school, and was horrified at the way these white collar drug pushers were deliberately targeting children for a lifetime of addiction. It was a risk because I had a wife and two young children to support, plus school loans to pay off. After about a year I went back to work in hospital administration but continued leading STAT for the next 15 years. Our most significant accomplishments were helping to outlaw cigarette advertising targeting youth, including paid promotion in movies, and making it harder for children to access cigarettes including outlawing cigarette vending machines. The work received a number of mentions in the Pulitzer Prize winning book “Ashes to Ashes” by Richard Kluger. Read more>>
Rayner Gabriel
I’m a performing artist based in South Florida. I graduated from the New World School of the Arts in 2011, earning my B.F.A. in Theatre and Acting. After finishing school, I managed to secure roles and perform on stage. However, the local industry and the limited opportunities weren’t enough to sustain a living. This prompted me to explore alternative income streams that would still utilize my skills. In 2012, I found my way to a Dubbing Studio and became a studio director. In my nine years there, I advanced to department head and also served as the lead artistic director. I made the most of every opportunity to learn from my colleagues. I sought professional development, which allowed me to grow as a voice actor, director, audio engineer, and corporate leader, all while nurturing my passion for acting, voice-over work, and music. Read more>>
Khris Jorden
When I first began getting into music, I worked with an artist named Terry James around 2018/19. He’s still a good friend of mine to this day. I shadowed him on his journey to learn the ins and outs of the music industry. Help make concepts for music videos, album covers, learned how songs were produced and worked on. At some point I wanted to “do music” but never fully understood what it meant. a year later I talked to a few friends and some family and was convinced to at least start with beat making. My brother is a known producer/engineer in Philadelphia and kept encouraging me to just make a beat and post it. Finally after feeling super anxious and doubtful of everything. I created a beats tars account in 2019 and went for it. Of course a lot of my beats in the beginning were pure trash. Read more>>
Anastasia Lee
One of the biggest risks I’ve taken was deciding to stay in the U.S. after my student exchange program ended. I came to the U.S. at 20, with no plans to stay beyond the program, but as war broke out in Ukraine, I found myself at a crossroads. I could return home, where my family was already struggling, or stay in the U.S. and try to build a life here to support them from afar. The decision to stay was terrifying. I didn’t have a safety net, a stable job, or even a full grasp of the language. I worked three jobs, with no days off, just to pay for legal fees and survive in a foreign country. On top of that, I had to navigate the complex immigration system, something I had no experience with, and often felt overwhelmed by. Read more>>
Interstar Salaam
If you do not have the ability to take risks. Never think about going into business. This year has been a major transformational year for me. It’s probably the biggest adjustment I’ve made thus far since being in business. And let me tell you, it hasn’t been an easy ride. Over the years, realizing the importance of knowing when it was time to pivot from one service option to the next was been vital and necessary for the longevity of my business. If I didn’t take certain risk. I knew I would eventually find my business stagnant, stuck, and lost looking for answers and solutions to whats next. You truly have to understand where you no longer fit as your business grows and make the necessary changes. Just know if taking this leap scares, you your on right path and go anyway. Learn as you grow. Be a sponge and let your passion drive you, and your fear fuel you along the way. Read more>>
Dante Puleio
I came to the field of dance later than most. I was playing catch up from the start and was thankful for any opportunity that came my way. I discovered dance at 19 and moved to another country to study. Since then I went on to become a principal and soloist with one of the world’s most revered modern dance companies. I had a successful and diverse performing career, in concert dance, musical theatre and film. Upon retiring I returned to school for my MFA which led to university teaching and three years later, because of my research, was appointed the Artistic Director of the very company that anchored my performing career. Read more>>
Cristina Nishioka
Starting a bakery in the middle of a pandemic was undoubtedly one of the riskiest decisions I’ve ever made. It was 2021 and while the world seemed to be closing down, I chose to open up, launching Beyond Pastry Studio in downtown. I felt a deep conviction that there was a room for something comforting, something familiar and a space where people could connect over quality baked goods. Not just a bakery, but a place that brought a little joy to the community, especially during such uncertain times. Read more>>
Jhoely Garay
I grew up in a family where music was not considered a “serious” career. Both my parents are accountants, and there are lawyers, doctors, and business people in the family, but no artists. I was very good at school. I won physics awards, math competitions, and literature awards, and my parents expected me to be an engineer or business major. So when the day came to talk to them about my interest in pursuing a music career, they were unhappy with the idea, to say the least. Despite the lack of support and much criticism about my decision, something inside my brain and heart told me I could make things work, and become a professional musician. Read more>>
Daizhon Cox
Growing up on the South Side of Columbus, I was surrounded by stories of struggle and survival. In a community where many believed that success was out of reach, I felt the weight of expectations. People often told me that kids from our neighborhood didn’t make it to prestigious places like Ohio State, let alone into rooms with elected leaders who held the power to change lives. Yet, deep down, I always believed in the possibility of something different, not just for myself but for everyone around me. It was this belief that pushed me to take a risk—one that would redefine my life and those in my community. Read more>>
Crystal Petry
One of the biggest risk I have taken, was quitting my traditional job and betting on myself. I have never worked for myself and I knew that “now” was the time to take the risk. If I was going to take this risk, take this chance then I needed to do it now. I am loving taking this risk. I was scared when I first started my business and years later I am still scared. When you take a risk, I don’t think the fear ever leaves you, but you learn to work in your fear and not let that fear stop you Read more>>
Neha Sikder
I took a major risk when I started Desoire before even beginning high school. At the time, it felt like so much was on the line—my grades, education, and overall well-being. Balancing the workload of school and building a business seemed almost impossible. Fear crept in, making me question whether I could actually manage both. But as I weighed my options, one thought kept coming back to me: “No risk, no story.” Read more>>
Kendra Guthrie
In 2021, I took a life-changing risk by leaving my career in higher education to follow my passion for mindfulness, yoga, and wellbeing full-time. I had been working at the University of Oklahoma in Tulsa for over seven years, balancing roles as a yoga teacher and Scheduling Coordinator. With the pandemic, everything changed and the small spark glowing in my heart to create change in people’s lives lit a bonfire to serve. The more time I spent working with individuals overcoming adversity and trauma—those in recovery programs, justice-involved spaces, and youth in underserved schools- the more I witnessed how trauma-informed yoga and mindfulness had the potential to make a profound impact in our communities. Experiencing how healing these practices could be myself, I knew our collective futures stood a better chance at health and harmony if more people had equitable access to these vital resources. Read more>>
Annaly Cruz
Ever since I was little, I’ve loved cooking and taking part in any artistic activities I could find. But I never thought I’d be able to make a living from it. I ended up doing a Bachelor in Nuclear Chemistry and doing a PhD in Argentina. When my first child, Emma, was born, my perspective changed and my PhD lost importance. Playing with Emma, I discovered my love for bake cakes. I had a solid plan: finish my PhD, start a postdoc, become an investigator, and make enough money for a nice life. Instead, I decided to take pastry classes and leave the university. It was the most terrifying and important risk in my professional life. But I did it! I’m so happy I did. Doing what I love is the best thing I can do. I’m happy, and my creativity helps me to express my feelings. I’m so glad I started my own business! I really hope to become a pastry teacher one day! Read more>>