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.
Hayley Roussel
I learned what I do through a mix of instinct, persistence, and a deep-rooted need to create. Art has always pulled me in but choosing it as a career wasn’t exactly met with open arms. Even the people closest to me—people I love—worried it wasn’t realistic. They wanted stability for me, something more traditional, something they could understand. However, I chose art anyway. I think the biggest “risk” I took overall was changing my major “one more time”….*GASP* to studio art; I surrounded myself with color and concept, like-minded people, and I kept painting even when the path ahead wasn’t clear. Read more>>
Bethany Mardian
This year I took the risk to compete in the Miss America Opportunity. This pageant system has been a house-hold name for over a century however, many do not know the dedication and meaning behind it all. Last year at the Miss Virginia competition, I was asked to help as a dresser backstage, through my job as a formal wear stylist. This one experience led me to fall in love with the sisterhood, competition, poise, and spirit behind the name of Miss Virginia and Miss America. In February, I competed for a local title and won Miss Southside Virginia, which qualifies me to compete for the job of Miss Virginia. Throughout the Miss America Organization, each delegate (local, state, and national levels) compete and prepare for private interviews with on stage portions including fitness presentations, evening gown, talent, and on stage conversation. Read more>>
Jack Polefko
In 2020, I was working a job filming lectures for doctors at a university. The pandemic had just hit, and everything had frozen, so it gave me a good amount of time to reflect on where my life was heading. I would look around my office (which was in the basement of the College of Medicine) and I would see skulls and other on the nose symbols reminding me that I could easily get work this job until I’m old and then die if I wasn’t careful. I was very existential in those days, constantly philosophizing about what it meant to go on and do something great. The cadavers in the rooms next to me was a nice way of telling me that it doesn’t matter what I do, just that I do something before my my body was next on the table to be observed. Read more>>
Madison McCain
Whenever the time came when I knew that I needed to take the leap of faith to go full time into photography it was so scary & nerve wracking but whenever the doors starting to open up for me I knew that everything would fall right into place for me. The scariest part was trusting the process of not knowing what it would look like but what was even scarier for me was staying complacent & not taking the risk. Read more>>
Amanda Lindsey
Taking a risk in my career as a magician came when I decided to audition for Penn & Teller: Fool Us. The idea of being on TV didn’t fill me with doubt — I’ve always had confidence in my magic and my ability to perform. What I wasn’t sure about, though, was whether I wanted to put myself out there for millions of people to see on YouTube. Read more>>
Grace Hollowell
My business partner Mia and I met at our last job and became fast friends. At the time we were hired, it was just a small (but growing) fashion startup, specializing in one-of-a-kind bohemian clothing, made in India. I was doing shipping, model photography, and customer service. Mia was taking product photos and helping manage social media. Over just 5 years, we helped grow this business from Etsy shop to multimillion dollar business. I eventually became COO and Mia became CBO. We were highly respected and entrusted to manage teams underneath us. This was truly our dream job for many years! Read more>>
Amin Bradley
When I first became a doula, I took the risk of leaving corporate America to pursue more meaningful work as a doula. It was challenging and rewarding in a lot of ways. I had to rely more fully on my “why” and trust that I would be connected with the families and opportunities that need me the most. Read more>>
Lucia O’Cleary
My story is one of reclaiming and celebrating identity, a fusion of pixels and spirit, a balance between the server room and the canvas. It’s a risk woven with the threads of my Chicana heritage, a defiant bloom in the concrete of a 9-to-5 world. Read more>>
Haylee Titterington
To tell you about the risk I have to share a little back story of how my business got started. I’ve always been photography obsessed and in 2015 I got my first “big girl” camera – a canon rebel. I never thought I would start a business, but I immediately was asked to take photos for people. In 2017 my roommate had approximately zero dollars for her wedding photographer budget, so she asked if I could just “take a few photos during the day”. I took this as a challenge and wanted to give her the best experience and photos possible. I YouTubed and googled everything I could about wedding photography and even though I was completely inexperienced, for what I had, I feel I did a good job. I actually had a ton of fun and loved the experience. Read more>>
Megan Brown
Music itself is not a risk because it’s pure. Deciding to create, perform and share your music is always a deeply personal risk as well as a financial risk, no matter how seasoned you may be. I’ll elaborate on both of those risk types.
I’ve been on stage since I was a small child so creative arts performance has always been a normal life for me. I started acting in stage plays and radio theater plays. I progressed to musicals and then eventually realized in my teens that singing was my true passion and what really made me feel good. I took that realization seriously and I dove in head first. Read more>>
Beauxx
For me, the risk wasn’t just about stepping into music—it was about stepping away from everything people thought I was supposed to be.
I grew up with a basketball in my hands. That was my identity. That was the dream. Everybody saw me as the hooper. Overseas ball, professional lanes… that was supposed to be the path. But life hit me different. Doors started closing. Real life started knocking—family going through things, bills stacking up, and the pressure to figure it all out hit heavy. Read more>>
Stela Sallaku
At 23, I took a bold leap and started my own company with no financial backing, in a country where women in business were still considered a taboo. It was a risk rooted in conviction—I faced cultural barriers, skepticism, and countless obstacles, but I chose to bet on myself. That decision became the foundation for everything I’ve built since. Read more>>
Sara Triplett
At 35 years old, I found myself unhappy with and unfulfilled by my career as a public-school educator. The decision to resign didn’t come overnight but as a result of years spent trying to reignite the spark and failing. Being married with two kids, carrying the family insurance, and making most of our income, this was not a decision that was made easily. I will never forget what my husband said right before I enrolled in beauty school, a place young Sara would have never even thought about. He said, “Look, we’re going to be stressed either way. Either we’re stressed because you’re unhappy or we’re stressed because we start back over financially. With the second one, I trust in the light at the end of the tunnel.” I am so thankful for him and his support. I learned so much in school – not only about esthetics as a craft, but as an industry. Read more>>
Clarke Holmes
It was 2012, and I was still a relatively new physician in Nashville. I was a physician of 15 years, but in terms of being a blue blood from Nashville with tons of connections, that wasn’t my story. As a sports medicine and orthopedic physician, I had been an employee at another orthopedic practice, when my boss, a physician just 10 years my senior, drops the news that he is retiring. So, I look in the mirror, discuss the options with my loved ones, said lots of prayers and said, “If I’m every going to be my own boss and open my own medical practice, then it’s now or never.” That was 2012, and this June, Impact Sports Medicine and Orthopedics will celebrate its 13th birthday. Read more>>
Helen Henderson
It was Los Angeles 2005. The big recession was looming. The disastrous Fannie May mortgage crisis was in full swing. Independent contractors, holistic healers, musicians, artists, writers, most self employed people, were rapidly losing income. Corporations were letting go of independent contractors and hiring their own workers, with part time hours and no benefits. I was performing at night with my own rock band, we were pretty good. I fronted the band and sang my own original material. We had just returned from Austria where I opened for Rod Stewart. Read more>>
Martha Argyriou
When I was 16, I left Greece and moved to California. That alone felt like a huge leap — new country, new culture, new language. I was just a teenager, but even then, there was a voice in me pushing for more. I didn’t know exactly what “more” meant at the time, but I knew I had to find out. Eventually, I moved to London to study psychology. I loved the city instantly. I spent five years there — studying, working as a mental health supporter, and building a life that, in many ways, made sense. But there was always something else tugging at me. Read more>>
Clement Maxime
The biggest risk I’ve taken would probably be my decision to move to New York City and study Musical Theatre. I always knew deep down that I wanted to be an actor and that a traditional desk job wouldn’t make me happy. I’ve tried throughout my teenage years to find non-artistic jobs to have a more steady and “normal” life but embraced my true vocation in my final year of high school and decided to apply to musical theatre programs in the USA and the UK. After a hectic final high school year cumulating my French high school diploma, and online American high school diploma and college applications and auditions, I got accepted in multiple schools and chose to commit to the American Musical and Dramatic Academy in the heart of the musical theatre, New York. I moved there in 2022, a few days after turning eighteen and without knowing anyone. Read more>>
Marissa Lamar
In 2024 I had spent most of the year vacillating between continuing to pursue my artistic endeavors or to just give up, give in, throw in the towel. The last few years had brought many changes to my life and I just couldn’t manage to keep up with anything. I had also fallen into a trap of just never feeling like I was enough. I got too wrapped into numbers and metrics, and forgot what it meant to just create for the sake of creating. Read more>>
Fatemeh Alhadjaboodi
Organizing my workplace was definitely the biggest risk I have taken. The summer of 2023 me and a couple of my coworkers agreed that enough was enough. We were sick of the horrible working conditions and the double standard on standards in our workplace. We got together over late night conversations and created our organizing team, once we talked to every coworker and they all felt the same way we contacted our union and placed our intent to organize. Even though joining a union is a fully federally protected activity, our company has unlawfully fired people for organizing, so proudly wearing our union button on our apron was essentially baring it all. Read more>>
Jon Worthy
About 3 years ago, I became a full time musician. I took the leap after working a corporate job for 8 years while simultaneously pursuing my music career. I come from a family where it’s normal to have a well paying job with benefits and know where your source of income is coming from. Money has always been extremely important to my family and particular me, so it was scary to take the leap and not know when and where my income would come from. I had the foresight to save a lot of money from working a corporate job so I knew I would be ok for a while, but to truly be in a spot where no one will pay you money unless you get asked to do a gig or production for someone is pretty scary. Read more>>
Brian Jeanpierre Jr.
My biggest risk was posting my first Tik Tok video. July 15th, 2024. It was the same day EA Sports College Football 25 released. For so long, I contemplated making gaming content and allowed myself to be scared off by the opinions of others. I vividly remember, telling myself “forget it, just do it what’s the worst that could happen, the video flops?” The last time EA Sports released a college football game I was 13 years old. I’d like to thank my overwhelming excitement for propelling forward to taking the first step to changing my life . 100k followers later…. I’d like to think, it paid off. Read more>>
Beth Amine
My biggest risk and most rewarding adventure has been to devote my life to artistic expression, both mine and to all the others I have included in my business ventures.
I decided early on, in childhood, that I wanted to be an artist. I would draw, mosaic, paint and write as a means to my own internal enjoyment and stability. I could always count on entering that happy place when I was doing something creative and intuitively self-exploring. In the time frame of my adolescence in the 1950’s and I believe this is still mostly the case, thinking of art as a career was a sure path to danger and starvation. So I obediently planned on being a teacher and had a major in English and a minor in Art when I started the University in the mid 1960’s. Read more>>
Lane Williams
Going into 2020, before the Covid pandemic, I did not see myself entering 2021 being a new small business owner. I was very happy at my current salon. The plan was always to eventually open my own business but I had no plan to leave for at least another few years. Once covid hit, EVERYTHING changed. With the uncertainty of the nationwide shutdown, I started wanting more control of my career and how I would evolve in my craft. As an employee, that is difficult to do with being at the leisure of your salon’s owner to progress. I really utilized the shut down to learn about what were the upcoming trends and I made the investment in adding to my skillset. Read more>>
Gregory Westphal
In 2016, after 3 years of starting the journey to be a professional concept artist, a friend of mine messaged me at 3 am PST. He is Polish and the time zone made sense for him to be at work and I was up burning the midnight oil on portfolio work. “Hey Greg, would you mind if I put your name in for a role at our company.” I agreed to apply and took the art test. I had previously lived in Singapore while I was going to school so living international wasn’t out of the questions and my family’s ethnicity is polish so I was excited it would be a natural fit. Read more>>
Amanda Moore
I always had an “office job” and when covid hit it became a “work from home” job. My whole life I have been very creative and enjoyed making things from scratch. On the side I would play around with cake decorating, desserts, flower arrangements, holiday decor, etc. I decided to give the Charcuterie trend a try and I loved it! Being able to make flowers and designs out of meats, cheeses and fruits really caught my eye. I began making charcuterie boards to take to friends and family. With a confidence boost from said family and friends, I decided to start selling them on the side. One thing led to the next and I had the opportunity to open a brick and mortar business. I always wanted to be my own boss and run my own business. But leaving a career with a guaranteed paycheck was terrifying! Read more>>
Carlos Ramos
I’m reminded of the risk I took by pursuing Dateless Possessions in Midland, Texas. I actually moved here for my daughter – she’s the reason I make sacrifices and push myself to be the best version of myself. Being a parent is my top priority, and l’m grateful to be able to provide for her and be there for every milestone. Read more>>
Chintia
One of the biggest risks I’ve taken was stepping away from my career in academia about two and a half years ago to focus fully on my own artistic practice. For over a decade, teaching had been central to my professional and personal identity—I taught Studio Arts (Drawing, Painting, Mixed Media) at Southern Illinois University and Auburn University in Montgomery, AL until 2019. Read more>>
Kenya Zandrowicz
One of the biggest, boldest, and most beautiful risks I’ve ever taken? Creating the Diva Kiddie brand—a universe of colorful, confident kitten characters who are helping little girls believe in themselves one page (and plushie!) at a time.
Diva Kiddie was actually born in 2019 during one of the hardest chapters of my life. At the time, my fiancé (now husband) and I were picking up the pieces after experiencing homelessness. My daughter had just welcomed her third daughter, and in the midst of it all, I felt this deep pull to create something magical—something that my grandgirls would love, hold onto, and grow up with. Read more>>
Monifa Harris
There’s a specific kind of bravery that kicks in when you’ve got nothing to fall back on—just a dream in one hand and $200 in the bank.
That was me, the day I packed up my entire life into a very small car in Jacksonville, Florida and drove 1,100 miles to Boston to attend grad school for opera. I had been accepted to the Longy School of Music. I had a scholarship. I had a dorm room waiting. What I didn’t have was a safety net—or any idea how I’d pay for the gas to get there. Read more>>
Rebekah Bean Ripley
I’ve done gymnastics for over 20 years. Five of those years were spent at the division one collegiate level. But most of my years as a college gymnast I spent injured and on the sidelines. It was really difficult physically, mentally, and emotionally. After years of resilience and hard work, I was finally able to make it come back. I performed a viral “Barbie Girl Floor Routine” while wearing a chunky knee brace. That routine ended up inspiring and giving hope to other gymnasts all around the world. Read more>>
Morena Hockley
Life as a creative person can feel very lonely. You wonder if your work will be well received. Will people understand you? Will you make any money with this? Creating is easy when you follow your heart. Opening yourself to the public…especially by selling your work…is riskier. Read more>>
Dre Wien
Starting my business was the ultimate risk. Having never worked in fashion or retail, I had to learn everything on the fly – and quickly! It was only 9 weeks from the time I saw the space to when I opened the doors, which knowing what I know now, is completely crazy. Looking back, it’s wild to think I even had time to get enough vendors on board and get inventory onto the racks. The first time I went to buy in person in New York, I had absolutely no idea what I was doing. It was the epitome of “fake it ’til you make it.” Read more>>
Alessia Di Cecco
In 2013 I made the decision to leave behind my corporate job one that I had spent many years building and was my north star. I realized I could no longer keep up with the pressure of career, motherhood, and caregiving. Battling severe stress and anxiety, I found myself unable to eat even a banana at my desk. That wake-up call led me to redefine success, build a new relationship with self-care, and launch Sweet Tavolo—a small bakery that reminded me of the joy in slowing down and the power of saying “no.” Now, I use my journey to help others do the same. Read more>>
Anna Karpinski
In 2019 I took a huge leap of faith (in myself). I became the president of AIGA St. Louis, and I took on more leadership of St. Louis Design Week, both of which held a great significance not only to me but to the design community of St. Louis at large.
With AIGA being 30 years old, the pressure to keep the organization running to even improve upon it was immense. I had no real knowledge or experience of how to lead a board or how to provide for a community, and was far from an established designer in my own right. Even still, the passion I had for the organization and the support of those around me lead me to take that huge leap of faith — in myself, my leadership skills, and my future. Read more>>
Trish Lanns
Stepping into solo entrepreneurship was a leap of faith. The uncertainty of not knowing how things would unfold or being able to predict my income was uncomfortable, but I learned that growth happens in discomfort. It’s the catalyst that pushes us to evolve and expand. Once I let go of the 9-5, aligned opportunities began to flow effortlessly my way. Read more>>
Danielle Henry
When I graduated with my Master’s in Healthcare Management, I was filled with ambition and excitement for the future. But amidst that excitement, there was something else growing inside me—my desire to be more present with my growing family. At that point, I had one son, and I knew that, eventually, I wanted more kids. But the fast-paced, demanding career I was on would mean spending long hours away from home. The thought of missing out on those precious early years with my kids didn’t sit well with me. Read more>>
Hasaan White
I recently took leave from my job to solely focus on my music. I did this because I want to put every inch of energy into my craft and I’m finally starting to believe I can really make it in this industry. Read more>>
Ebony Goodrich
The biggest risk I’ve ever taken is being my true and authentic self without worrying about the consequences of my existence. Being open about being a mystic and taking pride in my spiritual gifts has brought many people closer while pushing others away. I had to understand that not everyone can see past their learned and preached perspective of mysticism and see the beauty in it. Read more>>
Amber Burnett
Over the years, I took a lot of risks. The kind that in hindsight were quietly preparing me for the biggest one: leaving my job and fully committing to building my business. Why? Because wellness coaching, creating group experiences, and supporting women through connection and healing brought me joy—the kind I didn’t feel anywhere else. But as long as I kept treating it like a side project, it stayed just that… a part-time passion, not my full-time purpose. Read more>>
Robb Teneo
That’s a tough one. Only because of the sheer amount of risks I have taken both in general, and for an insane dedication to art. The risks that I take nowadays, are a lot less reckless and more calculated haha. I’ve taken one-way flights to other countries (multiple times), with just the money in my pocket and a confidence in myself to figure things out. Every risk undoubtedly becomes a rich learning experience, and at various depths of cost. One of the most extreme risks that I took was deciding to move to Shenzhen, China. This is a huge province just North of Hong Kong, on the Chinese side. I rose to the occasion and took it as an opportunity to expand my mental limitations. Read more>>