The chapters in our stories are often marked by wins and losses. Getting a new job, getting fired. Getting a life-threatening medical diagnosis, beating it and getting a clean bill of health. Too often, due to a societal expectation of modesty and humility we are discouraged from talking about the risks we’ve taken that led to those ups and downs – because often those risks draw attention to how we are responsible for the outcomes – positive or negative. But those risks matter. Those stories matter. We asked some brilliant entrepreneurs, artists, creatives, and leaders to tell us those stories – the stories of the risks they’ve taken, and we’ve shared them with you below.
Sarah Keck|
In typical millennial fashion, I have had lots of “careers.” Everything from working for a catering business, to retail, to working for a denim company; it has been a real mixed bag. It wasn’t until I started a small Disney-inspired business with my friend Jordan that the creative juices really started flowing. We loved getting to create enamel pins and accessories with a magical flare. But it wasn’t enough for both of us full-time; so I took a job in a doctors office and slowly the small business took a back seat. Then the pandemic hit. Of course, it was hard on everyone but I found myself so tapped out creatively that I decided to download the Procreate app and start some Skillshare classes to improve my drawing. Read more>>
Alexandria White
In 2020, I was furloughed from my job and my income was uncertain. As a single mother, I was scared, defeated and anxious. How was I going to take care of my. household? The uncertainty, the fear, and the constant news updates about COVID-19 painted a picture of an unpredictable future. For me, the stakes were even higher. I was a single mother, solely responsible for my child’s well-being. Read more>>
Chad Dickens
The biggest and most important risk I’ve taken was wanting to put all my time and efforts into the entertainment industry. I was asked did I want to partner up and start our own internet radio station. I immediately said yes despite all the ear chatter of “Who is gonna listen to radio on the internet?” and etc. So less fast forward 20 years later and everything is basically done by the internet lol. Taking this risk opened so many doors for me as the years progressed, from hosting shows not just in the DMV but all over the country. I became a DJ myself and ended up starting my own station called Ryze Radio that was my pride and joy. Read more>>
Grace Bishara
One of the biggest risks I’ve ever taken was leaving my amazing, stable job at United Food Bank to start Becoming Grace Foundation. It wasn’t just about leaving a career I loved—it was about stepping into uncertainty, faith, and a calling that had been pulling at my heart for years.
For a long time, I had built a career in nonprofit fundraising and development, helping to fight food insecurity and support vulnerable communities. It became more of my identity. I had a great team, a steady income, and a role where I was making an impact. But at the same time, I was carrying a deeper calling—one that stemmed from my own lived experience. Switching from starting from scratch was becoming a nobody again. Rebuilding a different type of trust not only with the community but with myself and God. Read more>>
Jessica Heimsoth
I’ve taken big risks (like starting a business or committing to homeschooling my children), but I think some of the hardest risks to take are the very small ones. The risks that require me to give up “good-enough” or “comfortable” for something that MIGHT improve my life…..but might end up being MOSTLY a waste of time and energy. Pursuing adult friendships, getting up earlier in the morning to pray or work out, quitting alcohol, choosing to think kind thoughts about my husband, spending time regulating my own emotions so I could better help my children. These might not even SEEM like risks, but to me, and to people like me, the lack of intensity involved means these small risks require more of my energy, and are therefore harder to FULLY commit to. Read more>>
Manon Rinsma
In 2015, I took what felt like the biggest risk of my life—I left everything behind to travel the world with no set plan, just the certainty that I had to go. Everything in my life was ending. I was at a crossroads—anything was possible. I had no strings, no home, nowhere I truly belonged. Grief and anger still clung to me, heavy and unresolved. I knew that if I stayed, I would suffocate under the weight of it all. Read more>>
Tai Emery
I took the risk of leaving my 10-year trade as a qualified electrical fitter mechanic (Electrician). After becoming a licensed Electrical Contractor, I applied this knowledge as a thermographer. I was a blue-collar worker and one of the few women leading the way in the electrical and thermography field. Read more>>
Fataday Korngor
I think music is inherently filled with taking risks. By putting yourself out there and writing about personal experiences, you are creating the risk that some people won’t like the work you made. However, you have to let go of that fear in order to create something that’s 1000% you. Read more>>
Paola Pietri
At 41, I took my first yoga class, never imagining that a simple practice would ignite a transformation that would change my life forever. By 44, I had become a certified yoga teacher. But stepping onto this path was not easy—it required faith, resilience, and a willingness to take risks. Read more>>
Maiah Hollander
This is actually a blog post I have written that I think covers this topic well! The link for it is here: https://www.doucoaching.com/how-dou-do/the-big-decision
My decision to finally move abroad was born from a panic attack in a parking garage. But let’s back up a bit. This story is a bit longer than that and needs a little context. Read more>>
Camille Klein
I have taken many risks in my life, but one of the biggest ones is still ongoing. Choosing to become a photographer has been a significant risk for me. Let me provide some backstory. I grew up in a small farming community in North Dakota, with a population of less than 3,000 people, and the closest “city” was an hour away. Read more>>
Farin Nikdel
I was born and raised on the West Coast, where the comfort of home transitioned into the comfort of attending college in a nearby city, which then turned into the comfort of living there for nearly ten years. I had an amazing community of friends, my family was close by, and life felt predictable. But over time, that comfort began to feel stifling. There was a sign I passed every morning on my way to work that read, “comfort is a slow death.” I felt it. Read more>>
Jackie Audette
For as long as I can remember, I’ve had experiences that some might call unusual, or even paranormal. I could often see and hear things that other people couldn’t. This wasn’t limited to people either. From a young age, I had a strong connection with animals. I could sense their emotions, pick up on their energy, and even “hear” them in a way that felt as natural as having a conversation. I never understood why other people couldn’t hear the animals speaking to them or feel their energy as easily as I could. To me, it was just how the world worked. But as I got older, I realized that not everyone shared this ability. By the time I was in my 20’s I understood that what I had was a unique gift. And yet, I kept it to myself, afraid of being seen as odd or different. Read more>>
Chad Deberry
Being a poker player I dealt with risk every day, but I think one of the bigger risks was leaving my poker career to start Grit Group, a real estate investment fund, with a good friend of mine from poker. We had very little experience investing, and zero experience running a business. We discovered there might be an opportunity investing in mobile home communities. In 2017 we left poker, formed Grit Group, and went All-In. This was completely alien to me. Coming from a background of poker that was a single player game, financially stable, with total freedom to work on my own time whenever I want – to running a fund with shareholders, no salary, and working normal business hours was quite a leap from a lifestyle standpoint. Read more>>
Douglas Busch
We had started ecoTECH design studio to bring important sustainable and healthy building techniques as well as organic growing systems www.thefarminabox.com for growing your own food, www.pHLiving.us which was to help the MCS (multiple chemical sensitivity). Our goal and mission was to bring the public ways to improve their and their families lives. We brought in. intern architectural and engineering students from UCLA and USC to work on emergency housing and work on the information sheets for the public. We worked with Menlo Labs (organic food production), Nissan electric vehicle, Rocketdyne on wind turbines, LED manufactures, and on and on. It was a touch road but very rewarding to help people and hopefully help the planet. Read more>>
Diane Davis
TAKE THE LEAP OF FAITH! How will you ever know if you can fly if your focus is on falling? Change your mind, you change your life! CHANGE YOUR MIND YOU CHANGE YOUR LIFE! When you focus on the problem you focus on the lowest possible outcome for YOU! Most people are afraid of failing and or falling so they are not willing to take the risk, To take the risk is to step on faith! Believing is seeing BELIEVING IS SEEING! Personally, I have upheld my name The Motivation Queen by taking the risk! A challenge is only a perspective! The many risks I have taken I like to call them HAVING FAITH and BELIEVING! I took the leap of faith when I started my Entrepreneur journey and at first I was attached to my corporate job and I did have those doubts. What if? I used to be at work creating my log for Stay Motivated with the intention of creating a positive mindset space for individuals to discuss challenges encountered in life with a positive mindset. Read more>>
Deborah Moore
When I first got into real estate I was doing it part time then eventually stopped doing it. It wasn’t until 3 year ago I had some life changes and I decided to take a leap of faith and pursue it full time!! It’s definitely a challenging career but I have a passion for helping people and teaching them about the importance of ownership so I continue to keep at it. Read more>>
Yuki Khona
You know that moment when you realize you just can’t keep doing the same thing forever? That was me, sitting in traffic for the millionth time, commuting three hours a day to a job I was good at but didn’t love. I’d spent my whole career in corporate America, analyzing data, playing it safe, doing what I was supposed to do. And then one day, it hit me—this isn’t it. This isn’t enough. Read more>>
Karisa Lomax
One of the biggest risks I’ve ever taken in my life was actually deciding to pursue photography as a full-time career. I used to be a registered nurse before taking on this new path, so it was quite scary to go from a secure job that I spent years in school for to taking the leap and teaching myself photography.
I began my nursing career just before COVID-19 took over the world in March of 2020. I worked throughout the pandemic and even took on travel nursing assignments to see more of our country while helping others–plus, I couldn’t complain about the great money. Read more>>
Tracy Bowers
In 2014, I started my organizing company, Organize Simply, in California, occasionally taking on projects in Utah. I lived most of life in California and we raised our 5 children there. In 2018, I organized for an Instagram influencer in Utah. After she posted about me, my services gained popularity, leading to more clients there. I found myself going back and forth between California and Utah. The jobs in Utah were larger, with bigger families and storage spaces, requiring a bigger team. Around that time, my husband had an opportunity to take early retirement. We decided to take a risk: he would help with the business, and we’d move our lives to Utah to focus on organizing there. It was a big leap into the unknown, but it turned out to be a wonderful decision. Read more>>
Elena Miglino-sabean
Taking the risk from a steady paycheck to freelance life is a big one. I grew up in the household where both my parents worked. Sometimes they had two jobs each, and I learned from a very young age that if there is something that you want, you have to work hard to get it. I had many jobs that led me to where I am today. I think when I took the leap in my early 20s I kind of saw the world of rose colored glasses and I feel like that help helped me in a sense. Not knowing where your next paycheck is going to come from when you live on your own and trying to survive, work +play balance etc. is a terrifying thought to me now especially as a mom. During that time, I didn’t see it like that. I saw this as my independence and the ticket to everything I wanted. Read more>>
Shemica Watkins-johnson
Taking a risk in dance or anything you love means putting your passion on display for the world to see, knowing that not everyone will value it the way you do. The challenge isn’t just in the movement itself but in the vulnerability it requires. You’re exposing a part of yourself, your culture, your emotions, and your story, hoping that others will understand and respect it. Read more>>
Kaia Josephine
As a creative individual, you take risks everyday. You create art with others that sparks controversy, or you choose to personally take on a role that feels far-fetched. However, the biggest and most rewarding risk I ever took was probably moving to New York City and deliberately pursue a career in acting. I was living in Oslo, Norway at the time (the place I grew up) working in the film industry as much as I possibly could. I was young, and I didn’t know anyone around me that had moved countries to establish careers, let alone do something like acting. My family are all within the fields of teaching, medicine and business. So to choose art as a lifestyle, wasn´t quite the logical step for a prosperous future. Read more>>
Patrick Burke
I used to work for a small, volunteer based haunted attraction and I decided to take the risk and drive 2 hours West to work for Fright Fest. I left the comfort of the attraction I had worked at for 6 years to potentially not get hired at Fright Fest. 6 years later, I’m on my 4th year of being in charge of the team that decorates for Fright Fest. Read more>>
Jill Moysiuk
Five days before I was expecting to return to work following maternity leave, I lost my job.
And, you know what, it was one of the best things that ever happened to me. I think.
While I was initially pissed and heartbroken, I eventually decided (read: I needed something else to do besides cry) to look at my circumstances as an opportunity to journey down a new path and tell the corporate grind to suck it forever. Read more>>
Alma Kamal, Hamda Al Naimi
Hamda: Risk has been a constant in my life, not always bold or dramatic, but the kind that quietly changes everything. I struggled in school, especially with math, later realizing I had an undiagnosed learning disability. While numbers confused me, visuals made sense. Doodling helped me understand the world, and eventually, I found my place in graphic design. Read more>>
Amanda Held
In 2013, I experienced what felt like the ultimate loss—my father and business partner passed away unexpectedly from a heart attack. It was devastating on every level. My home, my farm, my business, and even my beloved horses were all gone. The dream life I had built seemed to vanish overnight. I left behind the life I loved and went to work in corporate America, thinking that chapter of my life was over. I had no intention of ever restarting my business. Read more>>
Angelo Giovanni Nardomarino
Annabelle Hedges
One risk that I would say was almost life-changing was doing my first-ever solo. I was about 11 or 12 when I started working on it for the competition season. I can just remember how nervous I was to mess up my first-ever solo, but I had a crowd of people cheering for me and supporting me, with my mom in the front row, of course. I can just remember the minutes leading up to walking onto that stage for the first time, my trio partners both by my side backstage. I ran my solo in my head, what seemed like, 50 times. I think my biggest fear was going out there and forgetting, or even worse, disappointing all my friends and family. When it was time to go on, I turned to Layla and Reese, my trio partners, and, I can remember the words to this day, they said, “You’ve got this.” Read more>>
James Ketchum
Taking on ownership of the CrossFit affiliate felt like a huge risk in some ways, and an absolute slam dunk in other ways. I had been an athlete in the gym for 7 years and a coach for 3, and out of need, I was the one most often scrubbing toilets and taking out the trash and cleaning floors, because I cared about the place and wanted it to shine. When it was announced to the existing member base that I was taking over as full owner, 100% of the members stayed, which made the risk all worth it. The gym was financially healthy before I took it on, and even with the debt load I’ve taken on to purchase the affiliate, the gym still has a profit margin. Read more>>
J. Dabney
The biggest risk I’ve taken would have to be truly believing that the difference I make in this world matters. “We live in a world full of distractions, we’re all awkwardly moving just to get reactions. …So the biggest risk would be leaning into my passions….” (Me) I lean on my family, friends, colleagues for direction. However, first & foremost, I stay patient and wait for my higher to give me direction. Read more>>
Marcus Goins
Taking a risk helped me so much more than waiting on anything to come to me. i was only doing photography in 2018 and everyone wanted me to do videos but I never was interested. One day I met a guy in Texas when I was on a trip with my friends and we became really good friends and he was teaching me the ropes of learning video every time we visited. So one day I was at home with like 300 dollars in my account and he hit me up asking if I wanted to come out there and work with him and I took the Risk so my video career started in Texas. Read more>>
Maria Stallone-Soto
I was living in a constant state of juggling—balancing a demanding corporate job, raising three kids under three, and running a signage business that had unexpectedly taken off after one of my videos went viral. I was stretched thin, exhausted, and, if I’m being honest, completely miserable. The stability of my 9-to-5 job was a safety net, but it was also a cage. I knew something had to give, but the thought of walking away from financial security terrified me. Read more>>
Nikki Scandalous
Some people need hard facts and numbers before making a decision. I’ve learned that sometimes, the most powerful guidance comes from something deeper—something unseen but undeniably felt. When I opened my salon, I wasn’t just following a business plan. I was following a feeling. Read more>>
Pamela Suvanna
The biggest risk I ever took was giving up my stable job for a day in the life of a model. After I returned home from IMTA in Los Angeles and got signed to my agency the Covid—19 Pandemic hit our country and it felt like my modeling career couldn’t begin yet because the entire country was shutting down. I was working as a medical assistant in Women’s Health living what most would call a “normal life”. It was a stable job and an honorable one. Working in medicine is rewarding because I get to heal others and spread my love to those who need it. However, it was not my truest passion. Read more>>
Randall Fleming
As a zine publisher who by accident crawled into the mainstream publishing world, I got a bit too big for my britches after I — also by accident — cut my teeth as a tabloid newspaperman in NYC. Because I felt I could do most anything in the milieu of publishing, I jumped into the deep end of journalism by starting up my own newspaper a decade later. I had no concept of risk, and while that derring do served me well in the punk rock world of zine publishing, it was not appreciated in the larger world of politics. Read more>>
Ryan George
Starting the overstock store was one of the biggest risks I had ever taken before, I was only able to start off with the bare minimum of inventory and financial investment, but was able to quickly grow from day one. I was able to bring in newer products often and then open the second store that’s all gaming and collectibles. I grew quickly from day one and continue to grow everyday! Read more>>
Tania Nawazkhan
One of the biggest risks I’ve ever taken was starting Titan Shape with no prior business experience or background. I didn’t have a blueprint, a business degree, or years of entrepreneurial knowledge to lean on—just a deep belief in the power of movement as a part of my purpose of God will over my life. Read more>>
Tyler Folds
At the end of 2023 we decided that we were going to open a second location. We had just bought out our other two business partners. Our inventory was starting to take a hit due to the expense and we were in the middle of hiring for the first time ever as a business. We had decided that the only way to make a second location work would be to have the first location fully staffed and focus on the new store almost solely. Finically we were already not doing so hot because of the buyouts and now we decided to take on way more payroll than what we could afford. Fast forward eight month to August, my business partner Joe and I open up Cold Shoulder Kicks Fort Lauderdale. Read more>>
Valeria Talavera
At 18, I had a choice: take the safe route or take a leap of faith. My family, especially my father, wanted me to stay in my hometown for college. It was affordable, familiar, and, most importantly, secure. But I had a different vision for my future. I wanted to study film at the best college in Puerto Rico, even if it meant moving away, facing financial struggles, and figuring things out on my own. So, I took the risk. Read more>>