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.
Peter G
Risk taking doesn’t feel as bad when you truly believe in what you’re doing. I think that everybody has the thought of wanting to be a rock star or famous in some form or fashion, however for the many it just remains a thought because if it were easy everybody would be doing it. Many start, but few finish. It is a very tough road and very risky. You have to be good with yourself when the world is quick to judge you and most the time never really gives you the chance. Now more than ever almost anybody can make a video or go live on any given platform and some are organically decent right out of the gate, but how long can they go for before running out of gas is the question? Do you have it in you to go the distance no matter what? That’s where the risk comes in. To give up what most won’t in order to be what most aren’t. I have always since childhood been entertainment minded, mostly musical. Read more>>
Tobias Fike
I think most of life is a risk. When you can’t know the future, every decision could be looked at as a risk. We can access the risk factor most times and steer clear of things that seem too risky, but it is part of our daily lives. It is hard to say how often I take risks and to what degree they are but I do push myself to take them. As an artist who works within various disciplines, I am interested in different ways of making so I like to challenge myself to learn new skills, or see certain ideas through. Sometimes this is putting myself out there in uncomfortable ways. Part of my art practice includes performance, and as someone who was extremely shy as a child, every live performance I do feels scary. Read more>>
Arlenne Escamilla Teran
My name is Arlenne, I’m an immigrant originally from Mexico, I was born in Oaxaca and the moved to the US with my family at the age of 10 years old, the move was rather more difficult than I thought, I had to learn a new language and adapt to a new lifestyle, my family did not come from money, both of my parents always struggled, I see that now, something I did not notice was I was younger but they both worked hard most times two jobs at a time to make ends meet yet they did they best they could to provide for my brother and me. When I got older this is something it was embedded in my mind, you have to work hard to succeed, and while I was not able to attend to a four year college, i could never afford it, I did work and saved every penny I had and went community college and graduated as certified dental assistant, and worked as pediatric dental assistant for 8 years before my big opportunity came by then I was happily married to my partner and father of my daughter Tony. Read more>>
Tyler Moake
In 2021, amidst the hustle and bustle of life, I discovered a newfound passion: digital marketing, specifically, running Facebook ads. Every evening, after juggling two part-time jobs and attending full-time college classes, I’d dive deep into learning the intricacies of digital advertising. It was far from easy, and often overwhelming, but there was a thrill in seeing those digital campaigns bear fruit. Months rolled by, and the strain of juggling all these responsibilities began to wear on me. It felt like I was at a crossroads; I could see the potential of my self-taught skills but was constantly weighed down by time constraints. The decision wasn’t easy. There was comfort in the predictability of my part-time jobs, yet an undeniable allure in the world of digital marketing. Read more>>
Mary Battaglia
Hypnosis had called me when I sold natural sleep products like hypnosis recordings for my online business. I even found the school I wanted to go to but it was not the right time. The online business was not doing well so I went back to a corporate job. I was not happy in the corporate job, but stayed there because of financial reasons and benefits. I felt stuck. At the end of that 4th year my sister passed from breast cancer and at the same time my marriage failed and I became divorced. I realized my life was not working for me and I was the one that had to change and create something better but did not know how. I decided to go to the hypnosis school I found 4 years before that. I took vacation for 2 weeks to start the first module. Hypnosis felt so right but I was in the midst of buying my house and needed the job a little longer to get the mortgage. Read more>>
Nicholas Hyche
Prior to starting Der Wurst Hot Dogs, I was an Executive Chef for a major hotel brand for 7 years, overseeing multiple food and beverage outlets. Prior to that I worked my way up from cook to Chef through restaurants, hotels, and resorts around the area. With the hotel and resort world, there’s stability and structure in employment and benefits. Health insurance, 401k, PTO and biweekly paychecks. There is NONE of that in the self employed entrepreneur world, at least in the beginning. I risked that safety net, to leave and create my own business, jumping into the unknown. And I do not regret it one bit. Read more>>
Shaquan Coburn
“Taking risks” is just part of life to get you where you need to go. I learn that in life / and a creative. Every risks isn’t going to be successful and that is okay, as long as you took that step. You learn in every risk you take , and without them you would not be where you are! Read more>>
Beth Buelow
I’ve come to realize that, at least for myself, being a creative person means agreeing to live with a high risk tolerance. This isn’t just about taking a risk to earn a living from my creative pursuits and callings; the greater risk is of vulnerability, ego, and identity. If I’m not willing to risk those things, then I’ll not make much headway as a creator, let alone as a *professional* creator. But if I’m willing to open myself up and let go of attachment to how others perceive, understand, and accept me, then I stand a greater chance of making my creativity my livelihood. When I think of “livelihood,” it’s not just about money, although that’s an element of it. It’s about spending my time and energy doing and being what makes me feel most alive. Read more>>
Shannon Ashe
Starting The Everywhere Project together with my best friend has definitely been the biggest risk and adventure of my life. In December of 2020, the United States was experiencing the highest rates of fatal overdose ever. I had lost my brother in law just a few months before and felt like there had to be something I could do to try and prevent more lives from being lost. This led to me wandering the subway tunnels of Center City Philadelphia armed with narcan and peanut butter and jelly sandwiches. I ran into someone doing the same thing, she had blonde hair and was taller than me but around my age and also by herself. Read more>>
Justin Kramm
In 2002, I was at a crossroads because I knew that I wanted to become an advertising copywriter but I was hesitant to take the next step: advertising portfolio school. Funny enough, in my freshman year of college six years earlier at the University of Florida my first Advertising teacher told me that if I wanted to be a copywriter I should drop out and go to a 2-year portfolio school like Miami Ad School. Instead, I waited four years, double majored in Business, minored in Latin American studies, and then went to grad school for International Business. None of this got me closer to a job as a copywriter. After graduating with my Master’s degree, I took a job working in customer service for an Italian motorscooter company. Read more>>
Lorne Behrman
When I was 38 years old, I was laid off from what seems to be my last office day job. At the time, my daughter was 4, I was about to endure a divorce, and I was a guitarist in a punk rock band with a few record label offers. I was really overwhelmed, and scared–I felt like I had one foot in my childhood dreams and another foot in the reality and responsibilities of being a father and an adult. I collected unemployment for a few weeks while I tried to find a job, but a lot of the jobs I was applying for were going to younger people without kids. It was a challenging time. Read more>>
Jonathan Koe
Saying ‘yes’ to my creative self is, in itself, the mother of all risks. To me, being a creative is about saying yes to the moment-by-moment intelligence that runs through me. It’s about letting my internal river of creative force take me wherever it wants to. Being a creative isn’t confined to doing conventionally ‘artistic’ things like music, visual art, performance art, or film. There’s a way to do conventionally artistic things that can still evade the truth of being an artist at your core. Read more>>
Brandon Widener
Here are 2 drone stories. I have maybe 1000 of these so hit me on social media for more drone drama. Drones were sort of this new thing in 2012 and I dove straight in. I kind of got obsessed with them (like all things camera related) but holy hell I could fly it and nothing else mattered. I just got hired to film this running of the bulls documentary and I wanted it to be the best thing Ive ever done. Sooooooo I bought a DJI S800 EVO, the zenmuse gimbal, and a panasonic GH4 (I believe) with every single last cent I had in savings. Read more>>
Christina Neptune
I don’t like to refer to it as the craziest risk, It’s what I like to call a leap of faith. During the moment that I started culinary school. I had recently seen one of my children go through a terrible situation, so I was unsure of the strategy or what I would do. At that point, I had to decide whether to dive headfirst into something I had been avoiding for so long. My beauty business would be significantly impacted by this choice. My firstborn, my beauty business, was the one that allowed me to grow in my faith. Putting this company on the back burner would have a negative financial impact on me. This risk allowed me to discover a deep-down affection for something I had never known existed. Read more>>
Gabriela Bernal
The biggest risk I’ve taken so far has absolutely been my business, but as the saying goes, with big risk comes great reward. My business just hit a year of being open this August, while it’s still small and growing I’m beyond proud of the success I’ve been able to build thus far. I remember it like it was yesterday, I had just graduated college and well, I was dirt broke. Maybe $800 to my name, ha. If that, honestly. Thankfully, the only thing I had going for me at this point was the semi-decent job I landed a few weeks prior to graduating. After a quick one or two paychecks I realized that with my current job pay I wouldn’t be able to pay my student loans any time soon and probably work a few years before the thought of buying a house or traveling began to even slightly be part of any conversation. Read more>>
Trinetta Powell
In 2020 I worked as a counselor at a local community college. I loved my job. It was an answer to my prayers to a history of working in environments that were not pleasant or compensated well. At the college, my colleagues were great, the salary and benefits were what I needed, and I had autonomy about how I worked with my clients. However, at home life was hard. My oldest son was diagnosis with a liver disease that had him in and out of the hospital and gave him a life expectancy of 9 years at the age of 19 years old. My husband and I were faced with thoughts of how to care for him, and the financial cost that would be needed to cover medical expenses. So, even though I loved my job, I knew I needed more income. Read more>>
Dequontis Saul
For starters, I stopped the 9-5 work life to pursue my dreams of entrepreneurship. It never felt like a 9-5 was serving me in any way. I even felt like it actually diminished my talents. Since a kid, I’ve always been a natural leader, a people’s person, & always had a strong outgoing personality. The monotonous nature of a 9-5 job made me feel closed in & eventually depressed so I stopped pursuing it altogether to bet on myself and took the risk in March of 2019. Read more>>
Jennifer Honeycutt
Covid turned everyone’s life upside down – I am one of the fortunate people that was able to use the pandemic as a catalyst for a starting point of change for my future. I had built a name for myself in San Diego, CA operating as a high-level executive. 24 hours in a day were not enough to complete everything I wanted to accomplish. My mental and physical health were on the backburner indefinitely, my family and friends were distant acquaintances and those nearest and dearest to me were my work associates. I knew something wasn’t right and working but I didn’t have the time to even sit down to take a second to think about it, also- I got addicted to the buzz of grinding and being a “boss lady.” Read more>>
Nikki Turner
It felt like such an immense risk the day I decided to put down the deposit on my rental space. The “what if’s” certainly made themselves heard. “What if you do it wrong?” “What if your clients don’t follow you?” “What if you can’t make it and have to close?” “What if your neighbors don’t like you?” Seriously-it got nuts. However; when I reflected on the purpose of making this decision I felt resolve. I knew that I wanted it bad enough-and I was going to make it happen. Read more>>
Niki Levengood
Being an entrepreneur in itself is a huge risk… I have found though, that with huge risk comes huge reward. one huge risk I embarked on was two years ago… I have a salon in Ohio in which I had about 13 team members at the time. One of my team members at the time named “Shyanne” was moving to Colorado. Shyanne had worked for men company for about three years at the time. She came to me and said she was moving, we were all upset because we really enjoyed working together. She said to me ” I don’t want to get a new job” and without hesitation or completely thinking it through I replied saying ” well thats ok you don’t have to I will open one there and you can run it” Shyanne shortly after moved to Colorado, I followed along a couple months after and we spend our first double loft space. Read more>>
Audra Russell
In January 2020, I found myself standing at the edge of uncertainty, contemplating a daring leap into the realm of podcasting. I was driven by a burning desire to amplify the voices of Black Indie authors, and I embarked on a journey that promised both fulfillment and trepidation. With no prior experience in podcasting, doubts clouded my vision—would these talented authors even consider stepping onto my untested platform? And beyond that, would anyone truly tune in to hear their stories? With a heart fueled by passion and a belief in the power of representation, I took that risk, carving out a space where these remarkable voices could flourish. Little did I know that my plunge into the unknown would happen right before a worldwide pandemic. It was such a unique moment in time. Read more>>
Chase Chandler
Venturing into the realm of music took a bold turn as I embraced my first cruise contracts. The decision to step away from my cherished private music studio wasn’t easy, driven by both my dedication to my students and the novelty of not teaching. Embarking on a performance contract with Atlas Ocean Voyages marked my initiation into a lifestyle centered solely on performing. Admittedly, after 12 years of private teaching, the allure of guiding others soon beckoned, leading me to offer impromptu lessons to fellow crew members. Read more>>
Don Miroradoff
My life has been a whirlwind of risks. I was not born with a silver spoon; yet, I had dreams as bright as guiding stars into the unknown and a fierce determination to escape the confines of my past. The first risk that imprinted into my soul was ignited by the flames of the “revolution of dignity” in Ukraine. The Independence Square in Kyiv that once echoed with the laughter of families turned into a battleground, and the world watched in horror as peaceful protestors were met with violence for standing for democratic values. I was amidst those brave souls, risking kidnapping, unlawful arrest, and expulsion from college. Over a hundred civilian lives were sacrificed in the pursuit of justice. Read more>>
Lauren Jonas
I took a risk by co-founding a ballet company in 1993. I was a professional dancer up until then. My co-founder, Ashraf Habibullah, and I had watched a performance at the Lesher Center for the Arts in Walnut Creek and we saw how excited the audience was to have ballet in its home theatre and we thought it would be a perfect venue to house a professional ballet company. There Lesher Center had professional, theater, symphony orchestra and opera but not a ballet company. We slowly took a year to build our brand and we hired dancers in January 1994. Our first performance was March 10, 1994 and we are about to celebrate our 30th season. Read more>>
Brooke Kennedy
I worked in project Management in the Electrical Industry and our largest account was Boeing. I had a good salary, great benefits, weekends and holidays off, only a 40-hr work week and I was finished at 3pm each day. I was good at my job but I wasn’t fulfilled. I had to do some soul searching to figure out what I wanted to do for years to come. I was a server at a high end restaurant through college and enjoyed taking care of guests. I created an experience for them and anticipated their needs. I loved seeing regulars and building relationships. During that time, I also saw an esthetician every 5-weeks for services. I was the inquisitive client always asking questions. I was intrigued by the esthetics industry. Read more>>
Elizabeth Kennedy
In 2017, I wanted to start up a baking side hustle and began taking orders and baking from my home. I never would have dreamed of the possibilities that this side hustle would create. Earlier this year, I was presented the opportunity of opening up a bakery in my hometown. I have always dreamt of opening up a bakery since I was a little girl. When I was presented this opportunity, many emotions came over me such as fear, excitement, and anxiousness. I began to think of the risks that came into play. Where would the money come from? Where do I even start? Will I be successful? As these questions came, I began praying about the idea of taking this big risk. Read more>>
Henry MacEachern
When thinking about a risk I have taken, there is one that comes to mind almost immediately, and it was a life decision. I had just finished my first year at Montana State University, and I was stuck. Although this year was one of the best years of my life, it was one of the most difficult as well. By the end of this year I had skied over 100 days, learned to fly-fish, worked two different jobs, failed some classes, and had no idea what I wanted to do. I thought I was interested in studying film but It didn’t grab my attention in any major way. I was considering dropping out and becoming a ski/fly-fishing guide, but I didn’t feel like that was the best way I can show up in the world and give back. I knew I was meant to contribute in a more meaningful way. Read more>>
Stacy Burk
When my wife and I moved to Sedona to become photographers, it looked impossible because there was so much competition. It was also very hard to make a living because Sedona is mostly a retirement community and there is no industry there. We left everything behind and used all our savings to move. We both worked 3 or 4 jobs for the first 3 years in order to survive. We took on free clients in order to get pictures. But when people seen our work, then our business started growing and people were sharing our work and the spreading the word. Withing a couple of years, we were so busy we were having to turn new clients away because of how many people were seeking our unique take on photography for their elopements, weddings, adventures or portraits. Read more>>
Libby Ballengee
Booking my first concert was a risk. I had no idea what I was doing, how to do it, or what was involved. I just dove head first into booking a national touring act as a birthday gift to my best friend. How cool would it be to have his favorite band play our town and get to hang out with them? Sign me up! I fell in love with live music early in my life. Some of my high school band mates took me with them to see the Grateful Dead after graduation. It was my first concert, and a real baptism by fire. I was fanatic about seeing all the local music I could, which in my city was pretty cool during the early – mid 90’s. Bands like The Breeders, Guided by Voices, and Brainiac were busting out of the Dayton, Ohio local scene, climbing the national charts and inspiring the alternative rock movement at large. It was so cool! Read more>>
Jhamella Haynes
Today with social media and celebrities having such an impact of everyone it’s easy to be discouraged. Everyone wants to look like him or look like her and it takes a lot of self awareness and self confidence to really get out there in this day and age to model in such large crowds. When you don’t fit the image of what everyone hypes taking the risk and stepping out of your comfort is not the easiest but i promise over time it’ll be a walk in the park. I was terrified to model because one, i was dark skin two, i was a size 0. Not only was i ashamed of being dark skin but i was “skinny”. I took the rest of stepping out and not caring what others had to say and because of modeling i am the most confident version of myself i have ever been. Take the risk because so many more doors will open once you take that first jump. Read more>>
Tony Wayne
Taking a risk……that can be such a nerve wracking experience, especially when the risk is so big. We actually took a huge risk when opening Imperial Tattoo Company. The tattoo studio I was working out decided to just shut down without any warning to the people that worked there. They actually sent people to the shop to tell me as I was in the middle of a tattoo. Trust me when I say that I was just in shock. But whatever….life goes on. You pick up and keep moving. Anyways, I had a lot of clients in that area, so I left my phone number on the front door in case they needed to reach me to see what studio I landed at next. This was before Instagram was some huge thing. Word of mouth was still a big marketing tool. Read more>>
Abi Schlesinger
I decided to start my business, Charcuterie Collective, when I was a junior in high school. I felt a strong pull to take on something that was bigger than me, and work hard it, to see if it had the potential to be able to succeed. So, at 16 years old I decided to start the business. I was instantly blown away by the support and love we received from the community, and that helped give me hope that this could truly work! I am so blessed to be able to look back now, almost three years later, and see how the business has grown and multiplied into something that I never would have imagined that we would be able to accomplish! Read more>>
Bittina & Kevin Sheen
There are so many things that culminated into taking the plunge for both of our businesses and we did it all during the same year, which has been a rollercoaster. In 2022 we started the Poulsbo Film Festival when Kevin left his former employer where he organized a short film festival for 5 years. Kevin worked so hard building the branding and using his prior experience in festivals and Bittina leaned in to her community connections for venues. It was amazing to see the support and excitement for the festival in year one – something we could not have done without the support of the local business community. During 2022 we also got engaged (and moved in together and got married!) in the midst of planning PFF and to top off the year, we purchased Away With Words Bookshop at the very end of December. Read more>>
Missy Bonet
June 2022: The month I will always remember for the rest of my life. My grandmother, my best friend, unexpectedly passed away. My world was shattered and the world kept throwing me thunderstorms at each pass. Despite what my friends, family and the world may say, I walked away from a six-figure client, closed my business and said good-bye to several relationships to focus on my mental health. I took the risk and leap of faith that I would return back on my feet stronger, better and more empowered to be more conscious of the little time we have left. Read more>>
Katherine Sanchez & Chelsea Matteson
We met three years ago at a private practice in the valley after I (Katherine) made the decision to move back to Phoenix from Boston to start a family. After working together for three years, we found ourselves envisioning taking a leap of faith, branching out, and starting our own practice in Scottsdale. To our surprise, we were both pregnant and knew that we were about to embark on two new exciting journeys: Being moms and early career psychologists as we made the bold move to open our own practice while on maternity leave! Resigning from a secure job to chase after our professional dream came with risks, but we were determined to become our own bosses. Read more>>
Joe Kennedy
Taking risks is important and vital to the growth and development in this field. As an entertainer I like to push my limits, and reach that step just beyond comfort where new experiences can be found. Playing with more advanced players, and learning how to interpret the musical language they are sharing is risky. Learning the ropes of this business and the different ways musical entertainment is conducted in different genres of music takes time, and the differences are numerous. Mistakes will be made, failures will happen. How you recover, learn, and grow from those experiences will help shape you as a player. Read more>>