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.

Emi

I started my journey as a baker/cake decorator by making cakes for friends, coworkers and family. Eventually word of mouth spread and I was starting to get cake/cupcake orders from local friends of friends and friends of family etc. Then covid happened and my regular day job working in health care was becoming harder and harder to get to. With 2 kids at home aged 1 and 3 at the time, finding consistent, reliable and affordable childcare was becoming impossible. I decided to take a huge risk and leave management level day job to pursue baking full time. I had no idea if it would work or if I could make it last but I felt like it was worth a shot. To my surprise and excitement, my baking side hustle turned into a full time gig. Read more>>

Renata Diniz

A few years ago, I took the biggest risk of my life: I left behind a stable career, my home, my language, and everything familiar to follow my dream to pursue acting in Los Angeles. I was living in Brazil, working in a different field, and although things looked “secure” on the outside, I felt deeply unfulfilled. Acting had always been my passion, but for a long time, I didn’t believe it was possible for someone like me to actually pursue it especially on an international level. Read more>>

Vanessa Betance

We take risks all the time – no matter who you are or where you’re from. Personally, I’ve taken tons of risks, starting from giving my entire family, boss, friends, school -my entire world a 2 week notice that I’m leaving my home in Chicago to chase a dream by moving to Miami – with no job, just a place to crash temporarily, a dream and an incredible amount of Belief in myself- all at the age of 22. If I never took that risk fir major risk of my life – I would have never would have unlocked my passion for creative marketing and traveling the world to lead all I do with empathy – the way I do now. My main focus of this conversation is to emphasize the importance of believing in yourself in order to take risks that will lead you to places and people that are more and beyond and greater than you can ever have imagined. Read more>>

Kate Ship

For as long as I can remember, I’ve felt a deep pull to visit Scotland. When I was in college at ASU, I applied to study abroad in Edinburgh. I wasn’t chosen for the program, and the alternative option was more expensive than completing my entire degree—so I said no. That decision lingered in my heart for years as a quiet regret. Read more>>

Atom DeMarco

The past few years have been hard for me. Not just in a creative sense, personally as well. Between family issues & a pretty intense health scare last summer, I felt lower than ever before. This lead to a complete halt on putting myself out there as a creative. I dissociated from friends, family, even myself. I’m extremely grateful for my girlfriend being the one who kept me going during this time. Recently, I received an opportunity. One where I felt it could be my way back into the game, so to speak. The circumstances put a lot of weight on the situation. It was my goal to be the “perfect” version of myself by then. Read more>>

Bil Brown

At the end of 2024, I released a long time client and business partner because the situation was becoming less than acceptable. There was no real hard feelings about it but it was time to go. The industry was changing rapidly and the client, always demanding, was making demands that didn’t make sense. I could have stayed on and made significantly less money than I had with them, but still made something, but I decided to release them completely while I could make something. Read more>>

Adina Marguerite Pease

I’ve spent ten years working on trying to make a career out of my creative work; original watercolor illustrations, a line of handmade accessories featuring my own textile designs, and block prints both on paper and apparel. I had one year, 2021, where my income finally hit five figures and I thought; ‘this is it – I CAN do this!’ Read more>>

Hillary And Will Presott

Moving from Boise to San Francisco wasn’t just a change of scenery—it was a leap. We had built a steady wedding photography business in Idaho, with loyal clients and predictable seasons. But we craved more. More creative freedom, more artistic collaboration, more room to evolve. So, we took the risk: we packed up, left behind our comfort zone, and dove into one of the most competitive and saturated markets in the country. Read more>>

Taylor Montgomery

Recently in June of 2024 I took the plunge to move across the country from St, Louis, Missouri to Los Angeles, CA. I had been visiting more than a few times throughout 2023 and 2024. Seeing how much the arts were expressed and appreciated I knew this was the place for me, . Read more>>

Lindsey Bruckbauer

The riskiest decision I ever made wasn’t joining the Army at 19… or moving across the world to South Korea for my first duty station… or walking away from the security blanket the military provides to pursue a “normal” civilian life… or even relocating across the country in the middle of a pandemic for a job. Read more>>

Jeffrey Hammond

One of the biggest professional risks I’ve taken was choosing to build my podiatry practice around a direct care model—a decision that goes against the grain in today’s insurance-driven medical world. Read more>>

Jamil Bilal

I always knew I’d walk a creative path professionally — so I knew I couldn’t ignore the pull forever. It all began with a single decision: taking a risk. Back then, I realized I was pressing beyond the usual limits — pushing myself in ways that didn’t quite fit into the traditional mold. I was changing the tune, so to speak, and trying to understand how art and music could make real sense for me. Not just as a hobby, but as a way of life. Read more>>

Victoria Isernia

In 2021, as a young Opera Singer facing contract cancellations during COVID, myself and two other opera singers co-founded what is now Amelia Island Opera. It felt extremely scary at the time as I personally didn’t have any experience in Artistic Administration. However, it felt like the right move for us as we saw we were facing a world of shrinking opportunities for singers during this extremely trying time on the arts. We wanted to create opportunities for singers and musicians. We produced our first concerts in August of 2021 with minimal marketing and few resources. What we found was an incredibly enthusiastic audience who welcomed us with open arms. Read more>>

Katelyn Adducci

One of the biggest leaps I’ve taken was starting my own practice. It was something I thought about for six years but never quite felt ready to do. I kept waiting for clarity or some perfect moment that never came. What finally helped me take the leap were a few deeply supportive people in my life—my therapist friends, my partner, and my dad—all of whom reminded me that I didn’t need to have it all figured out to start. Before launching my practice, I felt stuck—creatively, emotionally, and professionally. I’ve learned that clarity often follows action, not the other way around. I really love the Terence McKenna quote: Read more>>

Amber Choisella

There was a moment, around the end of a long Monday, when I sat in my parked car in silence, staring at my front door. The house I had just bought with my fiancée. It was everything we dreamed of—quiet, charming, and our very own. But as I sat there gripping the steering wheel, I couldn’t bring myself to go inside. Read more>>

Alyssa Poole

Far from family, far from friends. Immediately after getting married, we both packed up and moved to Atlanta GA so that I could dive into the film industry, what I thought at the time, was my calling. With just my husband working, I tried to get on as many sets as possible. After day playing a couple times, I finally landed a position on a Mini-Series that lasted for months, but after that… nothing. I received no work. Then the Writer’s Strike happened, followed by the Actor’s strike. By the time I had realized the film industry was not what I was meant to do, years had passed. I had been working as a waitress for some time, feeling utterly defeated. Did I waste thousands of dollars on a degree I’d never used? Read more>>

Sue Perez

There’s a moment most people never see — the moment you walk away from what’s “working” because it’s no longer aligned. For me, that moment came after two decades behind the scenes in TV and film, working with networks like HBO, NBC, CBS, and other major media outlets. I had built a successful career as an Emmy Award-winning makeup artist, traveling on location throughout the continental U.S. and working in the heart of New York City. I was the one helping others shine for their close-up. And while I was excellent at it, something inside me was whispering: “It’s your turn.” Read more>>

NNylari Iralynn

Back in 2009 I started my company and I named it T&I Accessories, LLC. My company has since evolved from just providing custom jewelry accessories to sew custom garments to now providing education and consulting services to individuals and other businesses. The name of my business has evolved to NNylari Iralynn, LLC. It was challenging at first to make the hard decision to transition my love for the arts into educating and consulting others but I was faced with health challenges back in 2022 that changed my life. I said I could never give up on my dream of making this world a better place one connection at a time so I made the decision to stay in business but alter the way I did my business so that It didn’t harm me physically. Read more>>

Myrta Vida

¡Hola! I absolutely love this question because it brings me back to a pivotal moment in my career that changed everything for me. Read more>>

Hope Beryl-Green

Starting my anti trafficking ministry, and writing my book To Tell the Truth, about my life story of enduring sex trafficking took a kind of bravery that I didn’t think I had. I had faced rejection all of my life, and to put my story in the hands of people who could possibly reject me and not believe me was beyond daunting. Also, financially it was a burden, because I felt that the Lord wanted me to quit my job and write full time. This was a giant leap of faith for me and my husband. I was able to finish my book in record time! Just in time, for me to go share my story in the Senate, to bring awareness to sex trafficking, and what each and every person can do to combat it in our communities. Read more>>

Kim

Once upon a time, before I was ever a financial advisor, I was a fashion designer. I had a corporate job with all the corporate pay and benefits – and on paper, being a fashion designer honestly sounded pretty great. Read more>>

Stetson Ybarra

One of the most significant risks I’ve ever taken was the decision to quit my job and embark on a five-month journey across the country, with the goal of visiting as many national parks as possible. Life had been moving rapidly, I had recently transitioned from living in Japan to settling in Las Vegas and I found myself questioning the path I had been on for so long. For much of my life, I had chosen the safer route by securing stable jobs, avoiding uncertainty, and simply going with the flow. Read more>>

Devon Ehrhorn

At 18, I took one of the biggest risks of my life and joined the United States Marine Corps. I had no clue where it would take me, but I knew I wanted structure, challenge, and something to sharpen me. It did exactly that. It refined my discipline and gave me a foundation I still carry with me every single day. Read more>>

Denise Howelll

For years I watched the television shows about investing in real estate (flipping). It seemed an easy and glamorous way to supplement my income. My mom, siblings, brother-in-law and I all wanted to invest in real estate. We just needed to find the right home. One that would not be too taxing since we worked, and I lived out of state. Something that would be a great part-time project. Our initial plan called for our mother to provide the capital to fund the purchase, I would fund the repairs, and my sisters and brother-in-law would handle the renovations. Read more>>

Shannon Barnes

Taking a risk is something that is not new to me. I can’t explain why, but even as a young child I understood that taking risks meant growth through facing fears. Typically, the fear of failing or the fear of loss will prevent us from takin a risk. I still hear the old saying, “better the devil you know than the devil you do not” While I understand the meaning under this proverb, my question was always, “Why does it have to be a devil?” Good things do not come from the devil; he has come to steal, kill, and destroy! Taking risks is how we grow and learn. So why would taking a risk, or stepping into an unknown be a negative? Yes, I may fail, and yes I may lose, but I will still learn and grow from the experience. Read more>>

Jade Gonzales

We’ve all heard the term no risk, no reward! But not all risks, promises rewards, sometimes its a loss, its a heartbreak, the outcome or expectation, doesn’t always give back the dream or success we hope for. Because of this, what I found stopped me, and what stops others is FEAR. Read more>>

Rochelle Cornwall

I took two big risks in my professional career. I’m still grateful for both and the opportunities for work/life balance they continue to provide me. I’m not rich, and I do have a lot of taxes to pay, but it’s been so worth taking the leap. Read more>>

Shainae Anthony

The question, ‘Where do you see yourself in five years?’ has always haunted me. I always gave an answer, but honestly I’ve never been certain of what career I wanted. I had a very loose idea of what I wanted to pursue and once I attended university, the uncertainty was even more apparent. I switched my major from Philosophy to Psychology, I switched schools, and by the time I entered my senior year… I was even more confused. Read more>>

Antionette Black

Using my 401K to start Blue Moon Deli has been the biggest risk that I’ve taken. I was able to purchase all of my commercial equipment, food, pay staff, get permits with the money. Once all of the money was all gone, the real show begin. It was a real struggle after 6 months of opening – thank God my husband still worked full-time. We survived and are still going strong. Read more>>

June Bunch

I switch the word “risk” for “adventure” pretty often. Was it risky to move from place to place seeking inspiration?
Perhaps, but when fireflies beckoned in Asheville and whales’ songs echoed in Maui, my heart was on fire.
When I could find a job and a place to live in an environment mysterious to me, I chased my curiosity and wrote postcards home.  Read more>>