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.

Nasimeh B.e.

I’ve taken so many risks in my life. When I was 23, I went on a cross-country road trip with two friends, to work on farms, with no plan afterwards. At 26, I moved across the country to one of the cities I got to know on that trip. At 30, I moved to LA to be an actor. And at 34, I moved to New York, where I now live. I’ve always felt drawn by the light in my gut. There’s a golden light in there – something that pulls me, even when I can’t see the logic to the decision or know what it will mean. Still, I feel drawn to the places, people, and locations that call to me. So far, every risk has turned out amazingly. The road trip led me to important life connections and lessons. The first city gave me my community and sense of purpose. Los Angeles granted me exploration of an important facet of my life. And New York – New York! – has given me an almost endless amount. Read more>>

Tay Cromwell

The most remarkable risk I’ve taken was moving from my hometown to NYC. I’m Brazilian, born and raised in Belem, a city in the Amazon portion of Brazil. Needless to say, Belém and New York couldn’t be more different if they tried. Not only due to cultural shock but leaving home was hard because I was away from everything I knew and loved. My favorite food, my favorite people, my favorite places, I was going to have to rediscover everything. And for a 17-year-old, that’s really hard. I came to New York to go to college for acting, and being in a new place you know nothing about is hard, but being there to pursue an artistic career seems twice as hard. It might get to a point where it feels more like everyone around you is competition, and you have to be the best, and you can’t fail because people around you already think you’re not going to make it. After all, we all hear stories about someone who wants to be an artist and has to quit because of a lack of money or stability, so it becomes your job to prove people wrong. Read more>>

Anne Donnell

Coming out as a psychic medium was like stepping out of my own skin, exposing a deeply personal truth that felt both powerful and vulnerable. Embracing my new abilities meant accepting an identity that challenged many societal norms, and sharing this with the world required immense courage and trust in myself. It involves risking misunderstandings, skepticism, and even judgment, yet there was an inner calling too strong to ignore. This journey has been about honoring a profound connection to spirit and serving a higher purpose, even when it means revealing a side of myself that has long been kept hidden. Because one of the greatest risks I took, was stepping into my truth, who I am today, and accepting my psychic abilities and connection to the non-physical world through Mediumship. Read more>>

Casandra Atangana

I am a mover from France and ever since I learned that I was American (born) my whole life was dedicated to move to the US for dance. I had an entire book dedicated about finding jobs in the states especially LA, finding which area to live depending of the crime rate needless to say I was BINGING all youtube videos. One day after school ended I took the leap to buy a ticket to go to the states, my mom had my whole childhood to prepare for the moment and she helped me purchase my flight. Funny enough I ended up in NYC…a state I knew nothing about and had to move here in 2 months so imagine spending YEARS into looking on how to live in LA to end up in the city that you know nothing about and have now to find all the information. Read more>>

Kathryn Rivard Elizabeth Conarroe

Like many of you out there, we took a leap of faith and quit our jobs with a steady income and benefits to open our own business. When you start a business, you need to be slightly delusional and set aside the rational portion of your brain. Every day presents new challenges and you wear many hats, but when you learn something new, or overcome a new hurdle, nothing is more gratifying. Did we know we could build a website? Hell no! Did we think we had accounting abilities? Absolutely not! Math is not our strong suit. But we work together, we scream, and we figure things out eventually. Read more>>

Dallas Sbar

Taking a risk in life is always a big step for many people, for me personally it was becoming a model. Coming from a world where fixing cars older than I am and slinging wine glasses to other connoisseurs, makes modeling seems far out of reach. One night at my wine bar I was scouted by the great people at Page Parks. I was given an opportunity to go to their offices on my next day off just to check and see what it was about. I decided I had some extra time so I showed up. A quick meeting with a career advisor, gave me the opportunity to learn how to model, become educated in the walks, the styling, and in the industry. I was able to walk at agent review for Page Parkes in front of about 100 different agents. I had so many callbacks, it took a little bit to decide what to do and how to do it. Read more>>

Kristin Printon

After graduating college, I did a solo backpacking trip around Western Europe for 3-months. I had recently gone through a bad breakup, and this was my abbreviated version of Eat, Pray, Love. I wanted to prove to myself how strong and independent I was, so I booked a round-trip flight to and from Ireland, and started planning. My original idea was to live in Ireland for 3-months, but once I realized how close I was to London, and from there, how close I was to mainland Europe, the trip exploded. I ended up visiting 9 countries, and did couch surfing everywhere I went, which meant I stayed with random locals I found via a website. Since most people couldn’t host me for the full 5 days I was usually in a city, I ended up having multiple hosts for each country/city. Having 18 different hosts, not all locals themselves, led to a lot of unique experiences to say the least! Read more>>

Dustin Phillips

I was born and raised in Manila, Philippines. As soon as I graduated high school, I told my Dad, who’s an American citizen, that I want to pursue acting in the US. He was very supportive about my decision and as a graduation gift, he started filing my petition so I can move here. As cliche as this sounds, I have been dreaming of becoming an actor since I was a little kid. The minute I finished watching Jurassic Park for the first time. I actually met Steven Spielberg last year! I was working at Starbucks at the time and he ordered a Chai Latte and I took the opportunity to tell him he’s my hero. I finally arrived in the US in 2015 but I spent some time with family in Sacramento first before I finally took the big risk of moving to Los Angeles in 2018. One of the other risks I took was choosing my dreams over love. I had to break up with my boyfriend at the time because he didn’t want to come with me to LA. Read more>>

Blaise Brooks

My name is Blaise Brooks and since I was four years old, I wanted to be an actress. I performed in every school play, I performed in plays around the city, which is Kansas City, Missouri, and I created my own talent shows in my basement. All I have ever wanted to do was to perform. When I was applying for colleges, I told my family that I wanted to major in Theater Arts, and even though they watched television every day and went to movie theaters, they told me that I had to major in a real major that made money, because being an actor is a dream, and would be too hard to achieve. I went to college and majored in Accounting, but I found my way to the theater department and I was in every play that the University had. Your gift will make a way for you to use it. Read more>>

Julian Brown

Earlier this year, February 2024, I took the risk of working on my plastic into fuel innovation full time. Prior to this point, I have been working on the machine for 3 years out of my own pocket right out of high school. I had several successful viral videos online showcasing the device, but had never been paid for them. I was monetized for the first time in February 2024 on tik tok, and made a viral video which paid me quite well. Up until this point, I was purely making ends meet through a secondary handyman business I started. It was a risk to jump into content creation full time, coming from providing a service, which meant money was guaranteed as long as I worked and provided that service. Read more>>

Heather Browning

Looking back, walking away from my 14-year career in higher education was easily one of the biggest risks I’ve ever taken. It wasn’t just about leaving behind job security, professional recognition, or all the years I’d poured into that path—though those things certainly weighed on me. The real risk was letting go of everything I thought defined me and questioning what “success” truly meant to me. I was stepping into a life that, for the first time, felt fully and authentically mine. But to do that meant stepping into the unknown. For years, I had been building a career I was proud of. I had earned the degrees, published, and spoken at national conferences. I was working with some of the top universities in the country, and by all appearances, I had “made it.” But I started to feel stifled, like a supporting character in my own life instead of the lead. I began to crave a different way of living—a more integrated, balanced life where fulfillment wasn’t limited to weekends or days off. I wanted each day to feel meaningful, not just a matter of “getting through” the week while constantly teetering on the edge of burnout. Read more>>

Felicia Jackson

I made a significant career switch – from a designer and creative director in fashion to a women’s health coach specializing in perimenopause. After 20 years of working in fashion, I knew I wanted to do something different with my life going forward. The question was – what gets me excited? Fashion had always been my passion, but I grew out of the industry as I got older. And I wanted to find a purpose that connected me with other women. Over the years, I had made my own health and wellness a priority and, in turn, had managed to alleviate the perimenopause symptoms that I was suffering from. It always returned to health and wellness when I thought about what excited me. And so, I took a leap and decided to make my lifestyle my new career and become certified as an Integrative Nutritional Health Coach. My goal is to help other women who are struggling with perimenopause symptoms find relief and balance in all areas of their life. I address physical symptoms and the mental/emotional turmoil that often comes along in midlife and can be exacerbated by the fluctuating hormones of perimenopause.  Read more>>

Liz Brunner

I describe myself as an “intelligent risk taker” because I am in my fourth career chapter. Each and every time I left one career chapter for the next new one, take a risk. I started out as a classically-trained singer, sang semi-professionally, toured Europe and was simultaneously teaching high school chorale music. However, after two years of teaching, I believed, instinctively, there was something more I was supposed to do, although I had no clue. So, I took a step back, and worked in retail for a couple of years to give myself some time to figure it out. Read more>>

Sonysha Sangare

The risk that I took is going to New York City for a model gig while being homeless, and it turned out to be great, because almost 2 years later, I am moved into my first brand new two bedroom apartment and is able to continue my journey of a influencer model artist. Read more>>

Meghan Lorine

For years, I suffered in silence through increasingly painful periods. Doctors dismissed my symptoms, telling me it was ‘normal,’ or that it was just ‘part of being a woman.’ But deep down, I knew something was wrong. After countless appointments and even more moments of self-doubt, I decided to take a significant risk for the sake of my health and quality of life: I sought out a specialist who actually listened, one who didn’t brush aside my pain as simply routine. I had my first laparoscopic excision and diagnosis surgery in 2018 to confirm what I had suspected all along—I had endometriosis. Read more>>

Najah Hammond

Taking the risk to believe in myself. No longer going for things approved by my peers or what my surrounding audience suggests but my own. Not being afraid of failing but finding beauty in every moment spent creating the life I have. Living in the present and not stressing over my future made my creative line of work satisfying and fun! Read more>>

Ant Devon

I was working for a company partnered with Wells Fargo back in 2019. The job paid okay, but I wasn’t truly fulfilled. I was wearing a mask to an extent. I couldn’t be my true self. One day at work I heard a voice tell me “quit this job, or remove you myself from it myself”. I ignored it, but I kid you not, a few weeks later I was let go. It made me realize that my purpose was bigger than working a job just to pay bills and survive. I knew that it was a sign to focus on building my social media through making music and creating content. I didn’t think about getting another job. For the next 2 years I practiced my singing every single day for hours, while building my online presence. I was able to eventually consult other artists as well under my own company Keep Pushin’ Entertainment. Read more>>

Hannah Stille

I never saw myself as a risk-taker, but looking back now, I can’t say that anymore. All of my life, I followed the “right” path. I graduated high school, earned my bachelor’s degree, then my master’s, secured what I believed was my dream job, married my high school sweetheart, and started a family. By society’s standards, I had it all. How could I not be happy? I did everything by the book! But behind the scenes, I was far from fulfilled. I dreaded each day, counting down the hours until the weekend. Read more>>

Huimin Hu

Three years ago, as I was preparing to retire from the hospital where I’d worked for 25 years, I began to think about how I wanted to spend my retirement life. Traveling around the world or returning to China to be with my siblings were both appealing options. However, I decided instead to establish the Memphis Chinese Community Center after recognizing the needs of the local Chinese community. While starting the center was challenging, keeping it running proved to be even harder, especially I heard many other Chinese community centers closed after only a few years. One of the biggest challenges was figuring out how to secure sustainable funding. Read more>>

Sean Nolte Jr.

Life is all about decisions, and most times we are unsure about which one to make; being intimidated about the fear of the unknown. It’s often that we are too worried about being wrong or right, even when the path is not clear. One must become comfortable with taking risks! Shortly after college, I made the executive decision to join the United States Navy. At that moment in time, things in my life did not seem so clear. There were a lot of missing variables. I did not own a decent car, did not have much in my savings, barely making ends meat at the part time job I worked, and I was totally unsure of what I wanted to do in life. All I could do is take things one decision at a time, and allow the consequences of each decision to happen. In the terms of Sir Issac Newton (Newton’s Third Law of Physics), “for every action there is an equal and opposite reaction.” Read more>>

Emily Rose

Ever since I can remember, I have always dreamed about being on stage, singing and playing my guitar. I would prance around my living room with the Karaoke Machine Microphone—singing any chance I could get. I played my first show in pre-school; it was at the public school talent show. I sang Shania Twain’s “Any Man of Mine.” Looking back, I find it funny and crazy that I sang this song as a pre-schooler. I would sing every chance I got—at local talent shows, performing the National Anthem at different events around town, anything like that. After some guitar lessons, my parents decided they wanted to help me get gigs. Read more>>

Iris Ayala

The biggest risk I have ever taken was starting my journey as a content creator. Content creation has been a dream of mine for as long as I can remember. But it was a dream that I put on a shelf for years because someone once told me “who would watch your videos.” Since then I was scared of being perceived and making a fool of myself. So for years I sat on the sidelines watching other people live my dreams. Around 2020 I was lost and trying to find my purpose, and I just felt a pull to start creating content. In 2021 I found the courage and posted my first TikTok. This decision changed the entire trajectory of my life. Read more>>

Harry Guinocor

A pivotal moment that transformed the trajectory of my career was when I chose to step far outside my comfort zone by applying for a challenging leadership position. For the majority of my career, I had been deeply engaged in hands-on work with clients as a Physical Therapist. I thrived in that direct, personal approach to care, so when my supervisor suggested I consider a middle-management role, I was initially hesitant. I found myself at a crossroads, weighing the comfort and fulfillment of continuing as a staff member against the unknown challenges of leadership. Read more>>

Ashley Sweeney

One sunny late afternoon in the innocent 1960s when I was nine, I stepped out on a limb in the deep woods behind our house on rural Long Island on a dare, my toes grabbing the branch and my wild blonde hair trailing behind me. Step by cautious step, I gingerly put one foot in front of the other and used my arms for balance. The freedom! The feeling of lightness! I was in my body and out of my body as I walked between earth and sky, and my heart swelled with the excitement of it. Read more>>

Kelly Jackson

I want to start by saying, I have spent the majority of my life being the most risk-adverse person on the planet. I was the master of playing it safe, often at the expense of experiencing the depth of true happiness. And in 2020, that all changed. As the world was undergoing a massive reset, I was in the midst of my own personal reset. I was fresh off a divorce, feeling incredibly isolated and lost, and made a decision to leave my 15-year Corporate career to start my own coaching business. I was unhappy in Corporate for as long as I can remember, but pursuing something else felt scary and risky. Read more>>

Cestari

For my debut album “In A Moment,” I knew that I wanted to create an experience around the release. I’ve always wanted to figure out ways to make concerts more interactive, and also include more elements outside of the music. When I recorded this album I knew I wanted to start with these “experiences” with this project. This led to me deciding to create music videos for all of the songs on the album, as well as a large concert to feature them simultaneously, almost as if it were a movie viewing. Read more>>

Nicole Lewis

I have been a practicing veterinarian since I graduated in 2013, working in a variety of roles during that time with a goal of working primarily in global wildlife conservation while also incorporating my love of travel with my adventure travel blog into my full time career. In May of 2024, I decided to leave my full time clinical position to pursue my goals. I created my own LLC called WildSide Vet LLC to offer contract work and pursue wildlife conservation research and to focus on growing my blog business and writing books. My first year pursuing this has resulted in less income, as one would expect, but a deep sense of freedom and a strong feeling that this was the right move. I have since signed several work contracts and made connections with several people in the field that are turning into conservation partnerships and my blog has grown significantly. Read more>>

Max Cattana

‘I have no idea what I am doing’. If I hear myself say this, either inside my own head, in conversation with someone or as I pace my bedroom talking to myself…it’s usually a good sign. The larger the gap between where I (the performer) exists and where the work (the play, the script, etc.) lies, the larger the ‘I have no idea what I am doing’ seems to scream inside my head. And that’s where the juice is. That’s the unknown. If the gap is small, and sometimes, when there is no gap. I find I am playing myself, I am playing the ‘known’, there’s no risk and the audience might as well come spend a morning with me while I walk around the streets of Bondi, sip espresso and rub the sleep from my eyes. Read more>>