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.
Lexi Norton
Moving out at 16 years old has to be one of the toughest challenges I’ve ever faced. Always take the risk. I have learned so much at such a young age. This industry is so tough and facing all the challenges growing up all hit me at once. I have worked full time ever since, while doing school full time as well. It’s definitely been hard to balance work, school, dance, and music all together and I’m still learning, but I wouldn’t take it back for the world. This has made me so happy to find what I love and be able to achieve my dreams as a little kid in a baby’s ballet class. Read more>>
Jillian Navarro
Being an artist inherently means you’re taking risks. However, that doesn’t mean it’s any less terrifying when you take one. After graduating from film school during the pandemic, I was lost and struggled to get into a routine or a place where I felt like myself. I bounced between a few virtual jobs, all that I loved and taught me many things, but nothing felt right. I wasn’t making time for my art or myself. I was not only in a depression, I was in a creative block. I finally found myself working multiple part-time jobs – a vocal teacher at a music school, an engagement coordinator for an up-and-coming international virtual music program, and from time to time volunteering at a climate organization. Read more>>
Julie Lee
I’ve been a risk taker all my life. I’ve always taken the initiative to chase opportunities, dreams, etc in all areas of my life and have never been a “sit on the sidelines” kind of person. If I know I want something, I will make daily decisions that will be get me closer to that thing. Read more>>
Ana Escalante
“Our doubts are traitors, and make us lose the good we oft might win, by fearing to attempt.” — W. Shakespeare.
For years, doubt kept me stuck. It convinced me that the safest path was the right one, that pursuing acting—the thing I had loved since childhood—was impractical, unrealistic, maybe even irresponsible. So I did what I thought I was supposed to do: I focused on my business degree, built an impressive résumé, and secured a job at a prestigious multinational company. I had stability, recognition, and a promising future. But I knew that wasn’t ‘it’ for me. Read more>>
Cynthia Harrell
The Seagroves Pottery Festival is the biggest in the state of North Carolina, and I was asked to participate after only one year behind the pottery wheel. I would be showing my “new on the pottery scene” pots alongside some of the biggest names in North Carolina pottery! I was excited, to be asked but felt,” This could go very well or be an awfully disappointing experience. Should I decline the invite or go for it? I decided to accept. I even donated a large platter for the Annual Seagroves Pottery Charity Auction! Read more>>
Edsha L Jones
One of the biggest risks I’ve taken was stepping into an industry that was completely outside my comfort zone and going all in on mentorship. I reached a point where I knew that what I was doing—while successful—wasn’t going to lead me to the ultimate freedom or life I envisioned. I was tired of trying to figure it all out on my own, and I knew if I wanted different, I had to move differently. Read more>>
Hayley Rawnsley
The biggest risk I’ve taken was embracing my creative identity. I always knew I was creative, but struggled to call myself an artist—even though deep down that’s who I wanted to be. I chose to study graphic design in college because it combined creativity with business. When I graduated during the pandemic, my carefully curated plans fell apart. Everything I thought was certain was now up in the air. I felt like my world became a wilderness overnight. Read more>>
Carissa Levin-epstein
The biggest risk I have ever taken was starting over. In 2019 I moved across the country and away from everyone and everything I have ever known. I was 26 years old and I still had no direction in my life. I had my first job in a spa at 19 in 2012. I worked there as a front desk, to key holder, then eventually assistant manger. I knew that the med spa industry was where I belonged, I just did not know exactly how. I watched as all of my friends went to college, graduated college, and began their careers. Back in 2013, 2014, and so on, nobody was on social media talking about injectables or the industry in general. I felt like my only growth was working the front desk, even though the spa I worked at won “Best Day Spa” in Central Florida multiple years in a row. Read more>>
Tionna Marsh
In March 2023, I made the decision to walk away from my job after having my last child. I had been in the education field for almost 10 years, and as much as I loved it, I knew I didn’t want to go back after maternity leave. After having my first child, I realized that teaching wasn’t bringing me the joy it once did. It felt like I was constantly being forced to choose between my career and my family—and I didn’t want to keep feeling that way. Read more>>
Nakita Robinson, Lmft
One of the biggest risks I’ve taken in my career was building Therapists Coworking by Epistamai. It wasn’t just a financial risk—it was a leap into uncharted territory.
As a licensed Marriage and Family Therapist, I understood firsthand the struggle of finding private, professional, and affordable office space. Many therapists, especially those in private practice, face an all-or-nothing dilemma: commit to an expensive lease for space they may not use full-time or settle for makeshift solutions that don’t offer the privacy and professionalism their clients deserve. I knew there had to be a better way, but when I looked around, I didn’t see anyone addressing the issue in a way that truly worked for therapists. So, I decided to build it myself. Read more>>
Estelle Ramisha
I grew up learning that education is important. My dad always said it’s important to have some kind of diploma so I always have something to fall back on when necessary. It just means more security. My mom’s a singer too and because of her I don’t know any different then to sing. When I was 7 years old, I started writing my first stories and songs. I started singing at school as well. Read more>>
Kaleigh Ceci
We have this one little life, and for most of the time we can feel like we’re just blowing in the wind, stuck in a pattern and imagining what your life is going to look like if you continue down the same path. I was always so shy and afraid to put myself out there. I’m an only child, so it was mainly me and the movies. I knew that’s where I wanted to be. In the movies…literally in the movies as in transport me to that world. When I learned what acting was, I realized it’s the closest thing to magic that there is. You can go to any world that you choose, and become a character within that world. In order odo that, I had to build up my resume, and I knew I needed some training and guidance, but I knew that training wasn’t going to be provided in Ohio. Read more>>
Ricky Davis
Our first big shift and leap of faith took place when I was completing my master’s degree. During that time, I heard the Lord tell me to “start the production company”. I knew exactly what He meant; start the “video production company” but it didn’t make sense because I was a recording artist and never wanted to be behind the camera. Nevertheless, I bought a camera and began an intense regimen to learn all things video production. We began to grow rapidly in skill and local recognition. We produced many projects providing full video production service including catered crafts services, branding content and music videos. Ultimately, in 2020, we filmed our first feature film, “Heart of the Streets”. Then abruptly our lives took another huge shift and life altering call. God spoke again and called us to move to “North Carolina, Charlotte”. Read more>>
Meleena Murray
As a life coach and cosmetologist, I’ve always believed that taking risks is essential for growth and success. Going into these fields required me to push beyond my comfort zone, challenging myself to explore new methods and approaches to better serve my clients. Whether it’s offering innovative coaching strategies or embracing the latest beauty techniques, I’ve learned that calculated risks allow me to evolve both professionally and personally. Each leap forward, whether big or small, opens doors to new opportunities, helping me create a more impactful business and making a positive difference in the lives of those I work with. Read more>>
Channing Monae
So I was currently in Atlanta, just opened my own salon suite and just quit my 9-5 job (picked it up during covid). Things were moving very slow, but I knew it would take time to build back up again due to COVID. I remember a young lady coming to me to get a Microlink service and told me she flew in from Phoenix, Arizona. I was so amazed because wow you flew all the way to Atlanta to get your hair done, and then by me.! She proceeded to tell me where she was there weren’t many hairstylists that was educated enough to do her hair and I should consider going to a state where it was high demand but low in the beauty department. At the time I took it as a mental note and continued to work out of my salon. Read more>>
Brandon Decremer
I had a life of instability, riddled with mental health mismanagement and anxiety. Do too brain damage, occurring while I was an athlete. I never believed in myself, that I could have true transformation or change, in My life. I was at rock bottom and decided enough was enough. I started to make real tangible changes in my life. I found a program led by the mindset mentor podcaster, rob dial. I took a huge risk and invested. From there my life started to grow daily. I learned to become a coach and more about my mindset and how it affects those around me.I never looked back and my life went in a completely different direction. I was always afraid to take major risks, until I did. Read more>>
Melissa Wald
Taking a leap of faith in my retail management career was one of the boldest decisions I’ve made. After years of gaining valuable experience and trying to climb the corporate ladder, I felt a deep pull to follow my passion for beauty and spiritual healing. I knew that stepping away from the security of a steady job meant venturing into the unknown, but the desire to create something of my own—where I could truly make an impact on people’s lives—was stronger than any fear. Starting my own business was both thrilling and daunting, but it has been an empowering journey of growth, self-discovery, and purpose, where every challenge has taught me more about resilience, innovation, and the power of trusting my intuition. Read more>>
Sj Janosky
For starters, great interview topics and questions! I’d say for the topic I chose (Taking a risk), I’ve been taking them most of my life. Taking risks is what fuels me, keeps things interesting, and keeps me on my toes. Especially as an artist. I am originally adopted from Guatemala, but raised in Pittsburgh, PA. It’s a small city, has a small town feel about her. If you haven’t been yet, come for a weekend visit. You won’t regret it. Check out the Cultural District while you’re there. I loved growing up in the Burgh, and was in a dance studio by the age of four. Even then I was always pushing to try for the more advanced dance classes; being put with the older girls to perform along side them for our annual recitals. So much fun. Read more>>
Katie Statema
I started photography as a hobby, and after my son was born and wanting a more flexible work schedule, I decided to take photography more seriously and see where it could take me. I spent countless hours teaching myself everything I could learn and shooting as much as I could. Deciding to take my business on full time is the biggest risk I’ve ever taken. The first few months were challenging, the uncertainties of entrepreneurship were definitely at the forefront of my mind, but gradually, the decision proved to be the right one. Within the first few months of me starting to take on sessions the number of clients and support I was receiving was overwhelming. Read more>>
Sham Moussaoui
On November 10 of 2021, I decided that I was going to make the transition to becoming a vagabond which is the term used to describe a homeless traveler although more specifically I’m a hobo because I incorporate the work aspect into it by doing temp jobs, such as warehousing, to continue funding this journey. I’d gone on a few extended roadtrips where I lived out of my car, referred to as rubbertramping, which took me across the country five times during the earlier part of that year. At the time, I was sharing an apartment with a friend in Jacksonville, Florida where I’d moved to from Oregon after enduring three surgeries, one shoulder and two on the same elbow, in the span of seven months. Read more>>
Stephen Weinstock
After many years as a theater and dance composer, I had an idea for a novel. A novel where in each chapter there was a deja vu, accruing to a past life narrative. Rather than do what a budding novelist ‘should’ do, and research what genre I wanted to write and all there is to know about it, I took the (unwitting) risk of diving deep into my idea. It expanded into a Scheherazade-inspired structure, where in each chapter a main character would recount a past life story they recalled. The concept expanded further into a fantasy series where 1001 past life tales are recalled, now accruing to a vast karmic history of a group of souls, a qaraq. The series became The Reincarnation Chronicles. Read more>>
Long Truong
Throughout my high school and early college years, I’ve always had the ideology that computer science was the only subject I was going to pursue. Growing up in an Asian household with high expectations, I was constantly pressured to think that if I studied anything other than computer science, I would be looked down upon and compared to other successful students. I proceeded to major in computer science at CSUSM only to fail 3 out of 5 semesters and nearly repeat every computer science required course. This placed a huge toll on my academic achievement and mental health. Faced with my most significant challenge, I was uncertain if my heart lied in computer science. Read more>>
Bridget Worstell
This time last year, I was a server & supervisor of a restaurant, and today I can proudly say that I am a business owner of a successful UGC and digital marketing service. If that isn’t a risk IDK what is.. lmao. I told myself the second I made a penny more than my serving job i’d quit and dive head first into UGC to see where it could take me. Now in just over a year, I’ve gone from discovering UGC on Instagram to working with brands like McDonalds, RYZE, Monopoly GO!, First Response and 90+ more incredible brands! Read more>>
John Torrence
I landed an event job at a media company however I didn’t have enough to move into an apartment immediately so I slept on a friends couch for an entire month before I could find an apartment. The first apartment I moved into I had two other roommates however, I was ok with that because I really wanted to experience the New York City life which is taking the subway to work, plan events for a media company, and play basketball in the New York Pride Basketball League. Read more>>
Sebastien Foucan
One of the biggest risks i took is to move from France to UK with my family not knowing what the future hold for me.
I knew in France my perspective were limited and i was dying artistcally. So i took a leap of faith to move. Both my wife and i didn’t have jobs. I thought it will take me a year or two to sorted things out. it took me 10 years. Read more>>
Olivia Martin
2024 was a thrilling year of strategic risks. It was a time to buckle-up, step on the gas, and enjoy the ride. At the age of 23, I bought my first house, solo-raised the first year of my puppy, and launched a travel, fitness, wellness blog called gainsandglow.com. Did I tackle a lot? Sure did, but ‘grit and grace’ were my motto and I ran with it. Read more>>
Erin Stevens
I take a lot of pride in my work as an OB/Gyn physician. Reproductive healthcare is complex, and it is a privilege to care for people throughout joyful, emotional, difficult, and life-changing circumstances. Throughout the course of providing care, however, I began to notice some of the areas where my medical specialty was falling short. One of these was in preparing people for the time *after* pregnancy. We do an excellent job optimizing health during pregnancy, but after birth, the general attitude seems to be, “Okay, that’s over now. Good luck. See ya!” People generally do not have realistic expectations for postpartum recovery or an understanding of what is and is not normal during that time. Read more>>
Spaceship
There’s a risk I took that I will always remember because of how it changed everything for me. It is a risk intertwined with love, art, and a complete departure from someone I never truly aspired to be.
For three decades, I had grown up within a fringe Christian sect. It’s gone by many names – Church of God Bible Study Center, BSCI, Inc., as well as the front group 24K Gold Music Shows, of which I was a member for over a decade, working as a touring musician week after week, year after year, for free – and their need to stay off the map probably tells you all you need to know. Read more>>
Erin Collins Kimball
Back in 2012 I was let go from my corporate job. At the time I had been teaching cardio classes for fun and extra income. I had just started discovering yoga a few years prior due to various minor injuries that slowed me down. When I left the corporate world I knew it was for the best, but my confidence took a hit. I definitely shed some tears in yoga during savasana, but I also felt the practice was helping me release and heal. I decided to be done with the corporate world and take a local 200 hour yoga teacher training. This was a huge risk leaving guaranteed income to then spend money on a yoga training and not be certain if I would secure work afterwards. Read more>>
Becca Bray
My success story is not unlike any from another business or person. There wasn’t some pivotal moment, no cosmic shift, no big epiphany that led to this chapter of my life. Regardless, I feels unique to me and is a tremendous story of tenacity, independence, determination, and my own sheer stubbornness.
I suppose many businesses had to make it or break it during the COVID-19 pandemic. Though, of no one person’s fault, it created a crucial moment of time where every decision an entrepreneur made was going to either lead to their ultimate success or their succumbing to the weight of the world around them. Somehow, every decision I made led to where I am now in spite of the fact I had zero clear direction or plan. Read more>>
Saphyre Skye Velasco
Honestly, The biggest risk I’ve taken was the decision to leave everything behind. My father, an immigrant, was my biggest supporter in my choice. Wanting not only the best in life, but to discover beyond what he was capable of. In pursuit of my dreams, he helped me attend higher education. As the first to leave home and graduate, I’ve felt this intense pressure to succeed not only for myself, but for my family. It was easy to give up during those times of stress, but knowing how proud my family is in how far I’ve gotten pushes me to keep going every single day. Read more>>
Sasha Nicole
Modeling was never part of the plan—at least, not one I thought was realistic. But in the back of my mind, it was always there. I was always the girl who dressed her best, no matter the occasion. I treasured each little detail—the way an outfit could transform a mood, the way confidence came alive through personal style. I wanted to live in that feeling every single day. Read more>>
Katerina Gerlach
When I first graduated from film school, I had an assistant job at a film company lined up – it paid well, had decent benefits, and was something stable in my career field right off the bat. However, my real passion in filmmaking has never been the desk work, especially in an assistant position – it has always been being on set, working with people, and leading the crew as a 1st AD (assistant director). A couple weeks before I graduated, a director whom I had worked with on a feature film previously reached out to me and said that some producers she knew were looking for an AD for their next feature and that she wanted to recommend me if I was available. In that moment, I realized that taking this assistant position would mean saying no to these opportunities, to the thing that I really had the passion for, for the next two years (the length of the commitment the company had asked for). Read more>>
Kaylee White
As I grew up, taking risks meant so many different things. All of them were right…in the moment.
I’m 24 years old (25 in May) and I can tell you what “risks”means for me now. Being big. I remember being a little girl being so afraid to speak. Afraid to disagree, to be difficult. Life has a way of challenging your beliefs because after a lot of living and learning, I began to understand truly what risks meant. Taking risks doesn’t have to mean jumping out of an airplane, it means speaking up in the moment your feel something. It means not shoving things in the back of your throat to simmer and dwell. You see something, you say something. When I reflect on who I admire, who I trust, I think of people who aren’t afraid to speak their mind. Taking risks means having integrity, being brave. Read more>>
Patty Ripley
My growth as an artist began in my late forties when I finally chose to focus on creativity fully. Life had been busy with raising two children, many dogs and managing a home while my husband travelled extensively for work. If you’d asked me in my early twenties if I’d be living such a traditional lifestyle, I would’ve laughed. No way! Stay at home Mom? What?! Read more>>
Zachery Williams
All throughout college I was under the impression that in order to make a living in life, I needed to choose a “recession proof” job. Your nurses, police officers, and teachers of the world… I never really felt like following a “dream” was truly an ideal move when it came to college degrees. I’m an only child so I had no older siblings to base other experiences off of. My mother never went to college and my father has a degree in pastoral ministries…soooo yea. Not a lot to go off of. Read more>>
Rebecca Henning
After working for 15 years in a resort spa doing both services for clients and a management roll, I took a 2 year hiatus from spa life. I was working in an oncology clinic as a patient service rep. I missed doing what I loved in esthetics and the opportunity came to rent a space and start my own business in Elkhart Lake, Wisconsin. I worked my regular 40 hour a week job at the oncology clinic and then took clients in the evenings and weekends. After 6 months of this grueling schedule and missing my family, I decided to quit my job and focus strictly on building my business. Read more>>
Raquel Cunningham
I have always had a desire to travel. Maybe it started by playing on my GeoSafari game as a little kid, maybe it was looking through all my parents’ art books, or maybe it was innate since I started walking at 7 1/2 months old. For some reason there were places I just had to go. In my mid 20’s I was ready for a life experience. The choices narrowed down to a 3-month long world adventure or move to New York City. My boyfriend at the time (now husband) and I decided to move to New York. Prior to the move, I already had the idea to make fitness programs for people with Tourette Syndrome based on breath work. (That was even part of my personal college admission essay.) I had no idea how I would do it, but that was the idea. When we decided to move, I wanted to have a purpose in going. Read more>>
Melanie Santos
Motherhood has a way of clarifying things, stripping away illusions, and making the truth undeniable. Less than a year after giving birth to my daughter, I stood at a crossroads. On one side was the corporate marketing job I had worked very hard for — the salary, the benefits, the societal approval, and what looked good on paper. On the other was a calling so deep, so undeniable, that ignoring it would have been a betrayal of my soul. The choice wasn’t easy at all. Walking away from security and into something as fluid and unpredictable as entrepreneurial wellness work, especially in a world that doesn’t fully understand or embrace it, felt like stepping off a ledge with no guarantee of a safe landing. But I knew I had to answer the call. Read more>>
Amy L. Miller
Taking risks when it comes to both my career and life trajectory is just…who I am. Being stuck or stagnant is the worst sensation for me, so when I begin to feel this way, I immediately look around for things I can change to get out of that. I’ve left relationships (including a marriage) because they weren’t quite right, left a W-2 job for entrepreneurship, quit before I had a plan, had a baby with someone I barely knew (nine years later, we are still together and the kid is doing great), and gave up a steady therapy practice to do things my own way in coaching….only to pivot and take a job as the interim director of a large humanist congregation for two years and then (now) come back to the coaching practice. Read more>>
Marcy Crouch
Starting The Down There Doc was never a “safe” move—it was a leap, a trust fall into the unknown, and honestly, one of the scariest things I’ve ever done.
For years, I had started and owned thriving in-person practices, I worked for hospitals, I taught, I trained other PT’s. I was hands-on, literally, helping women heal from birth injuries, regain strength, and reclaim their bodies. The work was intimate, personal, and deeply fulfilling. But I kept seeing the same problem over and over again: access. Women were falling through the cracks. Too many were left suffering because they didn’t have the right care, the right guidance, or even the right language to advocate for themselves. And they didn’t even know this type of care existed. Read more>>
Kim M.
When I first started my journey as a content creator, I was working in the mental health field and I was told by my supervisor at the time to make my social media private.
I took the risk of navigating a professional world but also sharing another space in a creative field. I’m happy and thankful I continued to do what I wanted with social media since it’s brought many amazing opportunities for us but also has helped smaller businesses. I’m truly thankful that I didn’t stop doing what I love. Read more>>
Mindy Yang
Innovation, by definition, means venturing into the unknown. When you’re creating something that’s never existed before, there’s no roadmap—just vision, research, and the courage to act. That’s both the thrill and the challenge.
One of the biggest risks I’ve taken was walking away from a stable path to build something entirely new—Perfumarie. The fragrance industry was deeply traditional and gatekept, leaving little room for true experimentation. I saw an opportunity to change that by creating a multi-sensory incubator—an ecosystem where independent creators and emerging brands could conduct market research while, as an agency, we developed products, strategies, and experiences to refine and launch their proof of concept. Read more>>
Lucas Piety
In late 2024, just before two major hurricanes hit the Suncoast of Florida (where I call home), in the midst of an uncertain election cycle, and after 10 years of producing short films and commercial video, I decided to take the leap and create my own video production company. Despite the seemingly ill-timed move, I’ve never been happier. I’ve found that my own creativity has flourished and the ability to dictate the tone, vision and direction of a production has left me feeling excited and energized about getting to do what I love every day. Read more>>
David Ortiz
A low risk life is what most people grow up hoping for. Including myself, we are programmed to settle for comfort. A wise women (my Wife) once told me that the vehicle to a successful endeavor is taking numerous, yet calculated, risks. It was indeed the best advice which changed everything. Read more>>
Kathryn Sheldon
I was full time at a larger network, as I had been for the first 11-12 years of my career. Any example I looked for, of how I wanted my life and career to look like in the future came from freelance people in the visual world (photography and motion). The path to becoming an executive or manager in an office, was not appealing me. I loved being in the field, working with different people and staying connected to the creative aspect of production. It became clear the only way to accomplish that was by taking the jump into the freelance world, and I’ve never looked back. Read more>>