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.

Ashley Bozek

I can’t remember a time when being in front of people, or an audience, wasn’t something I was chasing or dreaming of! From a very young age I would set my basement up like a stage and put on performances for anyone who would watch. Or use old cardboard boxes to carve out a TV and broadcast my next show…What was the dream? To some day be a Disney performer/princess. Read more>>

Rosie Anderson

Growing up we did not have a lot of money, in fact, we struggled. New shoes happened at the beginning of the year, and we wore them until there were holes in the bottom of them. That was the sign that we got new shoes! When I was about 8 years old, I told my Mom that I really wanted to go to Disneyland and she said that we don’t have any money for that. I told her to write a check like she does at the grocery store. Her comment was, “you better marry someone rich”. It was at that moment that I knew I would do it myself. I was not going to marry anyone to take care of me. Read more>>

Jordan Cigelske

Taking the leap into running my own business was, without a doubt, one of the most daunting and exhilarating risks I’ve ever taken. There’s something about the idea of stepping out on your own, away from the comfort and security of a regular paycheck, that just eats at you. It’s that constant voice in your head asking, What if I fail? What if it’s all for nothing? Read more>>

Johnny Rodriguez

One of the best risks I have ever taken is getting up on stage to do stand-up comedy. It is kind of like how people are afraid to go skydiving but after they do it, they are so happy they did it because it was the experience of a lifetime. For me, the skydiving was going up on stage to do stand-up comedy for the first time ever. I had been wanting to do it for many years and I didn’t have the balls to do it because I was prescribed a drug called Adderall, which actually shrinks your nut sack when you take it, but then when I got off of it, my Nutsack blossom into a beautiful normal sized nut sack! And then I got up on stage and I ate shit, but I didn’t care because all that mattered was that I got up on stage and took the risk. And here I am almost a year later still doing stand-up comedy every week as much as I can. It is my passion there is nothing in the world better than laughing and making other people laugh as well.. Read more>>

David Craig Ellis

Pretty much everything I do involves tremendous risk and in the long run, I wind up losing. But unless it’s dangerous and risky, I’m usually not interested. Three years ago I took on opening a Gallery in Williamsburg, Brooklyn. Knowing it was a gamble, I gave it a good shot. It’s been much more difficult than I had anticipated and has basically destroyed my life at this point. Friends and family members have pitched in to help and my alarm goes off at 5 am to get in there and dig. I haven’t slept properly in years, but I love it, it’s what I love to do. Read more>>

Pam Rivers

I come from a bold, creative, off the beaten path Mother. She was an OG feminist who busted through the glass ceiling in the pharmaceutical industry in the late 70’s. A badass woman in a mans world. She took my sister and me to protests. We listened to Helen Reddy’s “I Am Woman Hear Me Roar.” I was steeped in powerful creative woman energy. So doing things differently, putting yourself out there, and going against the grain was always an option. Read more>>

Travis J. Opgenorth

At one point in my career, I had a literary manager interested in working with me. It was the first time I ever had a manager interested in me, and he was a big name at a big management company, so this was a big deal. This was a person who could set the trajectory of my career. He liked a script I wrote and wanted to know what I was going to write next, so I had been pitching him ideas for a screenplay, and I landed on this story that was set in Africa. I pitched the idea to the manager, but it wasn’t something he felt he could sell, so he told me to move on, but I couldn’t. I saw the story in my mind so vividly and clearly that I had to write it. Read more>>

Katie Cook

In April 2020 I decided to leave a national sales position with an incredible company for a much harder job with terrible pay and long hours. I know its sounds crazy. The world was in chaos, I had 3 small children at home, a husband working as a nurse on the covid wing of his hospital and the world was on fire (or at least out of toilet paper). The company I had worked for was incredibly understanding, but with no end of the lockdown in sight and without being able to have a spouse step in as he was doing the impossible at the hospital for long hours, I couldn’t balance being a full-time solo parent and manage my portfolio. That is when I decided to jump ship and focus on managing my household full-time. It was the best thing I have ever done and the greatest accompliment I have been a part of. Read more>>

Craig Necker

In 2009 my then wife abandoned myself and our 1 year old daughter. I was a telecommunications engineer managing projects for Verizon in the state of Delaware. We were by ourselves so I decided to move back home to Nebraska so that family could help with my daughter Raylyn. I accepted an engineering position for a firm in Omaha. They offered me a local position but wanted to use me first to get a project running in Nevada. I let my daughter go to her birthmothers while I worked in Nevada (it was only supposed to be 1 month) After 3 months I spoke to the owner and he informed me that they hired someone else for the local position back in Nebraska. I wasn’t about to lose custody of my daughter so I put in my notice, and drove back home and got my daughter back. Read more>>

Lucy Manalo

Life has a way of pushing us in directions we never expected. For me, that moment came when I found myself in a hospital bed, facing a serious illness that forced me to slow down and reevaluate everything. It was a wake-up call—a reminder that life is fragile, that time is precious, and that faith and family are what truly matter.

During that time, my husband shared his dream of opening a superfood shop—a place where we could serve fresh, nourishing food to the community while creating something of our own. At first, I wasn’t sure if it was the right move. With so much already on my plate as a mother, teacher, and artist, adding a business to the mix seemed overwhelming. Read more>>

Ephemeral Collective

Early summer 2024, we—the founders of the Ephemeral collective—were sitting outside of Más cafe in Moab, Utah, dreaming. We had the inklings of an idea: what if we publish a magazine full of stories and art? What if it’s rooted in this place that we love? What if there’s a theme to it, a spark? What if we need workshops around it, provided creative space? We sipped our drinks and riled each other up; dreaming, dreaming, dreaming. We could start small in getting the word out, by taping posters around town and tabling at a local market. We looked at the market schedule: there was a market in a week and a half, but then the markets took a break for two months to avoid the blistering summer heat. Read more>>

Camille Rodden

Throughout my early adult years, I’ve had countless business ideas ranging from being a photographer to opening a boutique to crafting homemade soaps to designing stickers. The thought of pursuing any of them was overwhelming. I knew I would have so much to learn and so little to invest in startup costs. I had always had an interest in photography but did not consider myself tech savvy and the moment I messaged a photographer asking for advice I panicked as I read “you should start with doing some research on DSLR and Mirrorless cameras”. I left it at that and moved on to the next idea. I was horribly indecisive, constantly coming up with new business names, heavily researching my ideas, and then scrapping it all entirely only a few weeks into each business plan. Read more>>

Ashley Bates

Growing up, I was taught the traditional path: go to school, graduate high school, get a degree, find a career, and work until retirement. Entrepreneurship was never something I considered—I was comfortable in my hometown. But then COVID happened. Being home with my children gave me time to reflect, and I realized there had to be more to life than the city I grew up in. Read more>>

Elena Guzman

What’s the worst that can happen? Not making a sale? Taking risks on yourself can be daunting. I told myself many times, “You love baking, why not do it?” I came up with so many excuses not to start: being a new mom, just starting a new job, the timing not being right, not having the money, and fearing failure. Read more>>

Kristin Chase

I come from a dynasty of band teachers. My parents were both band teachers, although my mom switched to a different area of teaching when I was in elementary school. My brother is also a band teacher. My dad went to the University of Minnesota, I went to the University of Minnesota, and, you guessed it, my brother went to the University of Minnesota. I have been a middle school band teacher for 17 years. Band is safe for me. I know what I’m doing, and I’m good at it. Teaching is safe for me. I grew up in a house that had three different spring breaks and summers off all together. Teaching makes sense to me. Read more>>

Cary Williams

Taking risks is a huge part of being an entrepreneur.
Being a serial entrepreneur, I have taken many risks and feel like it is in my nature to be a risk taker.
I am sure you have read before, “No risk, no reward”. This is absolutely true in life.
My first business was a boxing & fitness gym and I opened it well before the words boxing and fitness went together! It was a huge risk to open a gym that offered something that no one was offering anywhere.
But, it was something I could see a need for. The demand was there but I had to look deeper to see it. Read more>>

Megan Jenks

When my business partner and I started our business, we knew it was a risk. My partner had actually started on her own with original designs turned into stickers and we decided to scale it up on a larger scale. Neither of us had business owner experience so we were and are learning as we went. The risk was whether or not our business would succeed. Not because of our lack of experience but because what if people didn’t resonate with our products? What if our designs weren’t as good as we thought? We researched other companies similar to us and saw how they did their layouts, how they marketed their products, and what their products looked like overall. After combing through these pages and researching the other factors, we decided that no matter what came our way, we were willing to make it happen. Read more>>

Luke Atme

If you divided the world into those who prefer to stay in the confort zone and keep behind the line, and those who stand out and follow their guts, I definitely belong to the last. But unfortunately that does also mean taking risks constantly. As a matter of fact, I decided to take a risk since the early age of 18 when I decided to leave my country and go studying music abroad. I could have pursued an “obvious” career able to give me good earnings straight after graduation, but instead I just wanted to live my life doing what makes me happy and here I am. Still now, I do lot of experiments with my music, I always switch into new genres and discover new way of composing. Creating is my thing, and I do feel afraid of the audience’s reaction when I put out something different, but at least it comes from deep within me and it’s all pure and genuine. Read more>>

Sierra Busch

I’m a nature girl at heart, having grown up in the Appalachian mountains of North Georgia and raised with some of the ceremonies and spirituality of my Native American ancestors. I never wanted to live in the city of Atlanta, much less NYC. But due to career circumstances with my boyfriend at the time, I was suddenly having to decide between leaving the relationship or shoving myself outside of my comfort zone to live in NYC. I was someone who was very dedicated to my goals and didn’t want to just follow a boy somewhere I didn’t want to be, but eventually I was able to rationalize the move because I knew I wanted to work in the art industry and NYC is the center of that world. So I agreed to go for 2 years, thinking I’d gather some relevant experience. I worked at an art gallery for a while, but a dream started to take root. Read more>>

Juneau Janzen

Day after day I would sit at the front desk of my retail job and dream of what life could be like if I wasn’t a college student living in a small town in Washington state. I knew my passion and heart was in creating art through photography, but was unsure how to pursue that in a real way. Everyone I knew went to school with me and was on a similar path as I was- something along the lines of healthcare, business, or science. I had very few friends in the creative industry and the few people I knew of lived a life that seemed like a fairytale. It never seemed attainable. I grew up in a smaller town with no connections to Los Angeles or anyone who could help guide me if I were to change my life path and career. Read more>>

Dennis Upkins

I think anytime a creator seriously pursues their calling, they are taking a bet on themselves which is always a scary risk. But those risks can often pay off. My first professional published piece of fiction, Stranger Than Fiction, actually came as a result of a challenge from author Todd McCaffrey.

Some years back I was at Dragon Con with a buddy who is a huge fan of the Dragonriders of Pern series. I was curious to learn more about the series and I’m always eager to learn about an artist’s creative process. Read more>>

Matt Fox

In 2008, my partner Enrique and I started our business as a side project. We both had other careers, but we were looking for a creative outlet. We decided to launch our own line of ties, bow ties, and pocket squares, selling them online from our Manhattan apartment. The response was incredible, and we quickly gained significant press attention. However, after a couple of years, we found ourselves at a crossroads. Despite our success, we were essentially breaking even and investing a lot of time without any financial reward. We had to decide whether to fully commit or walk away. Read more>>

Rachel Josefina

Being a performing artist we are told, consciously and subconsciously, that there is a right way to be in this career: to be ALL in and put your career before everything else. You have a trip planned? You’ll definitely have to cancel that if an audition comes up. You have your friend’s wedding? Don’t bank on getting to go to that. Nothing is more important than being available to book your next job. Even if it only pays $300 a week. Read more>>

Lea Grace

I’ve always been a “by the book” type of person. Once I was at an age to understand rules and consequences I realized that if I wanted to do things my way, or have the freedom to make a change, I had find out the formula to success and stay on that path. Even if that meant doing the things I have to until I can do the things I want to. So I made sure to stay the course, get great grades, go to a great school, be involved in the community, give back to the community etc. Read more>>

Steven Lush

When I think about risk in my art, it’s not about being bold for the sake of it—it’s about constantly pushing myself to explore new techniques, mediums, and ideas. In my maritime paintings, I take risks through precision, capturing the ever-changing movement of water, the play of light, and the atmosphere of a fleeting moment. It’s a challenge to bring realism to life in a way that feels fresh and immersive. Read more>>

Crysta Tepa

In order to share about the risk taken I feel like it’s important to give a bit of back story. I grew up in Hawaii as the child of an entrepreneur–my dad did many things as I grew up but for most of my childhood he was a surf board shaper so I watched as he used his creativity to support our family. He was very encouraging of going the non-traditional entrepreneur route & emphasized the time freedom perk of being your own boss. However, when I told him I wanted to be a photographer at 15 he told me, “no you don’t, don’t you want to make money?” luckily for me, the encouragement he had poured into me before that stuck & I thought to myself “just watch, I’m gonna do it.” I left high school at 15 despite having relatively “good grades” Read more>>

Sarah Oriza

In 2005, I founded G.I.R.L.S. Gym, a Mixed Martial Arts school dedicated to women, specializing in Kickboxing and Brazilian Jiu-Jitsu. This initiative was inspired by my passion for martial arts, witnessing fellow female practitioners who loved the training but eventually left, and the profound benefits martial arts had brought to my own life. Read more>>

Olya Blase

My Instagram account and blog is called Hint of Thought. I believe we can elevate everything to the next level if we have even a tiny ‘hint of thought’ behind it.

There is stuff we have to do.
There is stuff we can’t not do.
There is stuff we can’t undo.

Amongst all this is one truth, you have to DO to get anywhere. We tend to spend so much time thinking of how to alleviate risks that it takes us further away from doing. What is risk anyway, but the action before you have all assurances, before your mind has generated a bucket of alternative solutions to “what if” scenarios. Risk is a beautiful thing, risk and perseverance is so much more, it is the essence of living vs. existing. Read more>>

Denise Brook

I lost my job unexpectedly three years ago. Jobs in my field—biotech advertising—were hard to come by (I was a Creative Director), and I was terrified. I was job hunting but getting nowhere.

Around that time, I had been watching Portrait Artist of the Year and remembered how much I loved doing charcoal portraits in college (my degree is in Fine Art). I started mucking around with a grid technique, and it all started coming back to me. From there, I moved on to my next love—acrylic painting—and began with small canvases. Read more>>

Heather Harding

I started my business over two decades ago as a licensed psychotherapist. Throughout the span of my career I worked with many clients of different ages, gender, socioeconomic status, culture struggling with anxiety. Anxiety, it seems, is the most common feeling experienced. It is also the “catch all” for many different feelings. Many clients struggled with anxiety and felt that they didn’t have control over it, over their own lives. Some clients, before coming to me, were in many types of therapies and still having chronic anxiety. Some clients also were prescribed anti-anxiety medications, again still experiencing the anxiety. When anxiety occurs over time, the body stays agitated and functions in a ‘fight or flight’ mode. Read more>>

Joey Taylor

Starting a clean beauty brand business was never on my radar. I loved being a stay at home mom and occasionally working dental hygiene part time. When I found my self barely being able to pay my bills I had to get creative. I started making small batches of natural skincare products. They were simple with nourishing ingredients I trusted. At first I used them as gifts to show my appreciation without spending money I didn’t have. But as I worked late into the night, blending oils and testing formulas, I realized something: my own sensitive Irish, English, Norwegian skin, which had always been sensitive, was finally calming down. Read more>>

Greysa Lemons

Life in itself is a risk. Every step we take carries some level of uncertainty. Each decision we make becomes a part of our story—leading us to where we are now. And that’s where the real challenge lies: THE DECISION.

Endeavor made was created to inspire and equip a generation to pursue their God-given purpose through a lifestyle of grit, offering a wide range of handmade products like crochet beanies, clothing, tote bags, and more. Read more>>

Christine Morrison

Nearing forty, I walked away from my successful career as the Vice President of Marketing at Calvin Klein, Inc overseeing Ready-To-Wear and beauty, including the launch of the brand’s third attempt at a makeup line. Having spent the previous fifteen years in ad agencies, with an emphasis on beauty brands, the role was hard-earned. Read more>>

Mateo Hoyos

I have had the opportunity to work with wonderful people. One stands out to me the most. While I can’t mention by name, this person truly gave me the tools to become a great professional. This person inspired my work by passing along information other great attorneys before them passed on to their professional life. Things like: “words have meanings,” and “what happens next?” left an impression on me that in the transactional legal world truly are most important. The endless reiteration of the work-product taught me how meticulous you should be when drafting, negotiating and handling real world transactions. Read more>>