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.
Brock DeBoer
When I think back about a risk I have taken the one that really sticks out was to bet on myself and pursue my career as a full time artist. After being an artist assistant and having the opportunity to see how far I could go and the steps that that artist had taken it was time for me to go for it. Its not easy leaving the security of employment and the community that your a part of in that environment but there is nothing better than the feeling of earning something that you dream about. I had always made my work no matter how many jobs I was working I always had a studio and dedicated as much time as I could to it and I eventually came to the crossroads of I can either work for someone else or myself but the time is now. Read more>>
Brandon Ramos
In 2020 in the midst of a pandemic I moved out of my hometown (New York City) to Ohio. I am born and raised in New York but spent a few years in Denver. That time away was enough to give me the sense that there was a different life I could be living outside of the big apple. A life where bird song was not drowned out by car horns. A place where the chili is sweet, the trains are non existent, and saying goodbye to a friend is a saga. While the world held its breath in 2020 I rolled the dice on the buckeye state. Read more>>
Raven Stone
I really like to feel comfortable and stable and as a result tend to not take many risks. I was a bookseller for seven years, and one day, I got so frustrated with my job. It felt like I was in the minority of people who cared about getting the job done, and it always made it feel like so much more work. There were many things about that job that I liked, but on the other hand, there were many things about that job that added stress that bled into my personal life. So, I started looking for other jobs. I told myself I was “casually” applying for jobs, but not desperate. I wasn’t going to leave a job that I was good at and comfortable in unless I was positive that I would be upgrading my quality of life in doing so. Read more>>
Jen Borman
Opening my studio, Homewerk, during the pandemic was my biggest risk. It was a strange time for fitness, with many people still wearing masks and staying home.
On top of that, statistics show that 81% of fitness studios fail within the first year, and fewer than 50% last beyond five years. It’s one of the toughest industries to succeed in, and adding the tail end of Covid to the mix only increased the odds against me. Read more>>
Tom Brooks
Sometimes it takes me a while. I mean look, it was 1981 when I got my first professional acting gig. A senior in high school, and I had been afraid of everything since second grade. Except onstage. I could do anything onstage. I even loved auditioning because it was just another chance to perform. Read more>>
Jum Jirapan
Growing up in a traditional culture in a rural province of Thailand, with divorced parents and a conservative family structure, it often felt like the story of my life had already been written for me. I was expected to be someone’s property—not an individual with dreams, but a girl whose worth was defined by how well she served others. Education was considered unnecessary for girls; my family believed that primary education was enough and that my only duty was to care for the family I was born into and the one I would marry into. Individual ambition was seen as selfish. Even having personal goals was frowned upon. My grandmother tried to marry me off ever since I turned 13. Read more>>
Joey Gurwin
I think that my whole life has been a series of risks, with varying degrees of successes and failures. Professionally speaking; building a business around the arts is always a high risk venture, and the rewards (at least financially are not always the highest). There is a certain amount of failure and refocus that is expected with any business. And if I zoom in, every project that I create is a risk in some form or another. Will I like it? Will the client like it? Will it hit with it’s audience? These are all unknowns. Every project has the potential to fail, when you know that failure big or small is not just possible, but likely, it can make the process more freeing. Read more>>
Sandy Vaillancourt
I took a risk when I started creating and painting . I think all artists know this risk .
Choosing art as a career can be a bit of a financial risk according to some universities. How can you make a living through working in the arts? It’s a question people ask in America. We live in an economic society. People can’t help themselves and often ask impertinent personal questions, such as “how much do you make”. Society seems to care more about how successful you are and what you can do for them, and if you are worth their time. Artists don’t always think in this manner. There has always been a romance to making art. Being an artist is some what of a calling. It’s inside people to create. Read more>>
Reed Thomas Lawrence
The biggest risk I ever took was betting on a dream that had already let me down once.
A few years ago, I had a steady job—safe, predictable. But in my mid-twenties, I’d already walked away from that kind of stability once before. I traded a paycheck for a guitar and dove headfirst into life as a full-time musician. That journey took me from tour vans to Los Angeles, then Nashville, where I spent four and a half years writing songs, chasing the dream, and getting knocked down more times than I can count. Read more>>
Chris Bianchi
When I started CB Entertainment, I had nothing but a dream. No money. No credit. No backing. No safety net. Just a relentless passion for music and an unwavering belief that I could carve out a place in an industry known for breaking people before it makes them. The Beginning: A Leap of Faith. Read more>>
Katie McCalley
My name is Dr. Katie McCalley. I am a chiropractor, and have been for the last 8 years. I have taken more big risks in the last 10 years than most people do in a lifetime.
I grew up in Indiana and went to chiropractic school outside of St. Louis, MO. After school, I decided I wasn’t moving back to Indiana, but instead I would venture into the mountains in Colorado! (Risk #1!) Read more>>
Itay Forer
Absolutely, here’s a fuller, richer, and more detailed version of Itay Forer’s story that gives the writer everything they’d need to shape a compelling narrative about risk:
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One of the biggest and most defining risks I’ve taken in my life was walking away from everything that seemed “right” on paper—security, title, salary, and lifestyle—to pursue something that, to most people, sounded trivial. Read more>>
Athena Perez
Not the polished, Instagrammable version —but the gritty, messy, deeply human one that people living in larger bodies carry with them when they step into a gym for the first time.
When I first started building the Scaled Nation Working with Larger Bodies seminar, it wasn’t just talking to gym owners or coaches about programming or the physical body. It was about finally giving a voice to an experience that most of the fitness industry didn’t understand—and often didn’t want to look at too closely. I knew the physical hurdles people with obesity face, yes—but I also knew the emotional weight. The shame. The bravery it takes just to walk through the front door. Read more>>
Ashley Armstrong
Over 10 years ago, I fell in love with photography. Capturing memorable moments for my clients became a true passion for me. I started out by photographing couples and family but since then have taken a risk and expanded my services. Four years ago, I decided to take a big leap and expand into the world of Boudoir Photography. It was scary because I wasn’t sure what I was doing or if I would succeed at first but after that first event, I knew I was never going to look back! I fell in love with having the ability to empower women and promoting body positivity for everyBODY! Read more>>
Maranda Stuhr
The biggest risk I’ve ever taken? Leaving the security of my 9-5 to stay home with my girls. I always knew I wanted that time with them before they started school, but when our oldest was about to enroll in preschool, I had a now-or-never moment. If I didn’t make the leap, I might miss this window of time with them.
It wasn’t easy. Walking away from a steady paycheck meant making financial adjustments and stepping into the unknown. But deep down, I knew I didn’t want to look back and regret not being fully present in these early years. So, I trusted my gut and took the leap. Read more>>
Carrie Taylor
At 27 years old, I moved from Vancouver British Columbia, Canada to New York City without knowing anyone, and got a job as an instructor at The Swedish Institute College of health sciences in Manhattan. I was in the last semester of my 3 &1/2 year 3500 hour masters level degree at RMT school in Vancouver at the West Coast College of Massage Therapy, when I called the Dean of the college Lucy Liben, and got hired on the phone! The College sponsored me into the country on a TN Visa as a specialist in my field, and I taught pathology, neurology, clinical strategies, musculoskeletal anatomy/palpation, and anatomy & physiology. Read more>>
Roxanne Gray
When I started 801 Salon, I took several risks. Our first show was pulled together in only two weeks. I wanted to curate art exhibits and performances that would be accessible to the community, while also providing space and a platform for artists to show their work in accessible ways. We partnered with a local businesses who were willing to provide their space at no cost, and I cold-called a local artist whose work I admired. I was surprised that everyone involved responded with a resounding “yes!” and even more surprised that so many members of the community turned up for this event. We had over 150 people attend our first art exhibit. It told me that the community was hungry for these types of experiences, and gave me the momentum to build out 801 Salon into what it is today. Read more>>
Andrea Zambrano
Nine years ago, I took the most significant risk of my life—I packed up everything and moved from Colombia to Utah, following love. Leaving behind the familiar was terrifying, but I believed in the journey ahead.
Once in Utah, I quickly realized that sitting still wasn’t my style. I wanted to create something unique that reflected Colombia’s vibrant spirit. Colombia had so much to offer with its rich fashion, textiles, and craftsmanship, yet Salt Lake City lacked that touch.. But let’s be honest—where could you find stylish vacation wear during the colder months IF YOU WANTED TO SCAPE WINTER? That gap in the market became our opportunity. Read more>>
Sarah Blacker
As a singer/songwriter, empath and healer at heart since childhood, I’ve written about and processed my own experiences through song, with the hopes that others will relate and find solace in shared human experience. My musical path led me to the Berklee College of Music in Boston where I discovered the field of Music Therapy; the perfect synthesis of everything I loved and knew (and also built a humbly successful career as an original, touring and recording artist). Read more>>
Gretchen Amrein
I decided to open willow and waves salon during the pandemic, well I wanted to open April first 2020. I am so glad I pushed through, it’s been almost 5 years of running a salon and it has been such a blessing.
There have been many lessons along the way from growing a team, to starting almost from scratch when stylists left. Clients leaving and new clients coming in. Learning new skills and carrying products that respect the earth and the clients health. Read more>>
Karyn Gabriel
During my sophomore year of college, I decided to shift my focus from political science to art. However, when I stepped into my first art seminars, the blank canvas felt intimidating. I was young and uncertain of my voice. Seeking a path with more structure, I turned to interior architecture, graphic design, and product design—fields that blend creativity with problem-solving and found a home. That home led to a vibrant twenty-five year career in architectural design. Read more>>
Tom Jackson
I think there have been countless risks taken along the way.
Some businesses have started and failed, while others have kept going.
Either way, it’s all a game of risk.
Somewhere in the beginning, I realized it was my responsibility to build something – probably because of how I was raised and the responsibility that was placed on me (which I embraced). Read more>>
Colin Dawson
Moving to New York and attending the New York Academy of Art has been a huge risk and investment in my development as an artist. The price and demand on daily life living in New York and attending the Academy were daunting when making this decision. However, it was one of greatest risks I have taken in life. Being part of the scene where it’s all happening makes your own big ideas seem so much more possible. Read more>>
Jackie Hanselmann Sergi
Over eight years ago, I took one of the biggest professional and personal risks of my life. I left a senior executive role at a well-respected national search firm where I was managing a robust client portfolio, leading a remote team, and parenting a toddler — all while pregnant with my second child (though I didn’t know it quite yet!). I was navigating a season that demanded everything of me, and still, I heard the quiet call to something more aligned with my purpose. Read more>>
Shayan
Ok, this is the best point to start talking about my journey, which has been intertwined with taking risks. In my early teenage years, I began my BA in architecture with a lot of passion for it. However, as I moved forward, I realized that becoming an architect has two distinct sides: one is the artistic side, and the other is the engineering side. I was definitely more interested in the artistic aspect, and I was incredibly frustrated by all the engineering principles I had to apply to my work. Meanwhile, this was the time I was introduced to painting, which I will explain in depth later. So, it was time to make a big decision. I chose to quit school and invest all my time in painting, which I would say was the best decision of my life and has shaped my character along with all the good and bad that has happened until this point. Read more>>
Amber McDowell
Ten years ago, I relocated from Iowa to Minneapolis to pursue my art career. While I had begun selling my work in small coffee shops around Des Moines, I felt unfulfilled. I was searching for something more — a community brimming with opportunities for artists. Minneapolis offered everything I was looking for: art fairs throughout the summer, a vibrant gallery scene, exhibitions, and a wealth of artistic possibilities. Read more>>
Kitty Norton
Well, let me tell you about a moment in my life when I stood at a crossroads, a time when I had to step out in faith and take a risk. You see, there was a season when everything felt comfortable—safe, predictable, like I was walking a path that was already paved for me. But deep down, I felt a stirring, a whisper in my spirit that said, ‘There’s more for you. Don’t settle for the ordinary when the extraordinary is calling.’ It wasn’t about money or fame—it was about purpose, about trusting that God had planted a dream in my heart for a reason. Read more>>
Lisa Cordileone
One of the most impactful risks I’ve taken happened in an audition room last year…
I made the choice to just play. I gave myself permission to take up space, have fun, and connect. May sound simple but the risk was in the trust. And when I did… it reminded me why I fell in love with acting.
The ‘risk’ paid off. Booking the job opened the door to a rehearsal process I hadn’t experienced in a long time. It’s been a while since I’d worked on stage and I was very excited to get to work. It was a Christopher Durang play — bold, fast, physical — and I found that working “outside-in,” led me into the heart of the character in a new way. I came up through Second City Chicago’s training and hadn’t used some of these muscles in long time! Read more>>
Gina McKlveen
When I graduated from a small liberal arts college in 2017 with dual bachelor of arts degrees in English Literature and Studio Art, I decided to take what felt like the biggest step in my life at the time and applied to law school. I was a first-generation college graduate, but graduating from law school would make me the first-ever attorney in my entire family. Law school was something no family member had attempted before me. As the youngest person in my immediate family and the youngest grandchild on both maternal and paternal sides, I was used to having footsteps to follow–whether it was an older brother or older cousins, numerous aunts and uncles, my own mom and dad, or any of my four grandparents–I had plenty of people to look up to and learn from. Read more>>
Lauren Alsup
I graduated from College during the last major recession and knew a typical 9-5 wouldn’t be an option in order to meet the salary I hoped for/needed. So I gambled on an unpaid internship in the hospitality industry, nannied at night and worked freelance on marketing for clients all at the same time. Well, fast forward – I became a Head of Marketing for the same hospitality company years later all because I took a risk to work hard and showcase my skills at a truly trying time in the economy. Sometimes if you have a goal, the work to get there might be rough but it will pay off. Read more>>
Noelani Kallevig
In 2014 I was jobless and about to get kicked out of my parent’s house. It was a time in my life when I was in the process of getting back on my feet after some tough years struggling with mental and physical health problems, and after some major dead ends in my life I was desperate. Face puffy from crying and laying on my bed, I cried out to the Lord and asked him to show me what I should do with my life. Probably within the minute, my phone rang. Read more>>
Krista Reynolds
Taking the risk to start my business is definitely the first risk of many that I have taken. I had a good full time job and was doing photography on the side. We had just had our first child, so life was a little crazy. I had been photographing since 2007 and it was now 2011. My business had gotten bigger and was continuing to grow. Read more>>
Isis Spann
I have learned that there is no reward without taking a risk. We often wonder “what if” and think of all of the negative things, but what if we took that same energy and wondered “what if” but in a positive light? When I decided not to return to the classroom and open up my school, there was both a financial and emotional risk that I was taking. It would change my family dynamic and my day-to-day life tremendously. I would have to retrain my followers and supporters to see me as a business owner and not just a “teacher,” so I was also risking my reputation! Moving from the role of classroom teacher to business owner does have its challenges and moments of doubt, but I am happy with the results and the opportunities that I am getting because of the risk that I was (am) willing to take! Read more>>
Lacey Lueth
After owning Lola – An American Bistro for 15 years, the Lola Food Truck and operating the New Ulm Event Center I decided to add another notch in my belt and purchased The Cranberry in Herbster, Wisconsin in October of 2021. this area had always been special to me since I was a child growing up spending weekends there with my family snowmobiling or on the lake. The bar/Grill had been for sale for about five years when I purchased it. I had been there many times. This location was 5 1/2 hours from my other restaurant and projects in New Ulm. I ran all of them for about a year and then decided to sell my businesses in New Ulm to focus on the Cranberry. I kept my home in New Ulm where my daughter attends school. Read more>>
Yvette
Every time I create a textured painting, I take a risk. The bigger the painting, the bigger the stakes. Unlike traditional approaches where an artist might meticulously plan every detail, I embrace the unknown. I begin with an idea—colors I want to use, a pattern I want to explore—but I don’t fully control the outcome. The process is intuitive, almost like a conversation between the materials and my instincts. Read more>>