Fatima Ezzahra Mahdar
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.
Alyssa Irons
After I had my son, I knew I never wanted to go back to the world of education. I knew I could not give my son 100% of myself if I were still teaching a classroom full of children every day. Being a stay-at-home mom is such a blessing, but I started to lose sight of who I was and felt trapped in Groundhog Day. I knew I had to change something and that something was pursuing my passion for photography. I’ve had a camera in my hand for as long as I can remember, but I was too afraid to listen to my peers in the past when they told me to take photography seriously. The thought of becoming a professional photographer felt out of reach and terrifying, even though the longing to become one was in the back of my mind constantly throughout the years. Read more>>
Lisa Lamothe
While living in NYC, when I was done attending Lee Strasberg, I started auditioning. In NYC, EVERYONE is an actor!!!
So, unless you had a resume the length of a football field, nobody would take you serious and give you a chance. Read more>>
Emilia “emma Lee M.c.” Ottoo
(Not recommended by any means but) I risked a majority of my savings and homelessness for the vision of a project which had been in a planning and execution stage for several years. I was creating what would become my debut music album while simultaneously ending a long-term relationship and planning to move back to my home city, also to start a new paying job in tech after years of unpaid gigs which I was really excited about. This music project however meant a lot to me as an artist and regarding my purpose in life, one of those things that calls to your spirit constantly and keeps you enthused to be alive. Like the saying, “pain will push you, but a vision will pull you.” Leading up, I’d been in several musical groups which steered my attention away from exploring solo projects, was planning albums since I was a young teen, endured several resource, budget and stability challenges, all the while my social content and live performances were making me a highly anticipated artist in the independent underground. If and when I ever *did* get it together to step up professionally and come out with a official project, all signs pointed to a great step forward. So, with the eagerness to get the plane out of the gate and the car onto the highway, this album seemed like “the one…finally…this is it!” Read more>>
Zoe Alliaume
Right after graduating High School (I was only seventeen then) I decided to move to the United States to study acting. It was a huge leap, especially with Covid still going on. Everything felt so new and overwhelming: starting University, dealing with a different culture and currency (seriously, 12$ for a coffee??), figuring out the NYC subway… I was adjusting to another world. Read more>>
Tamra Cosby
In April 2024, I received an email from the Public Housing Community Fund for an Artist-in Residence Open Call. I was intrigued by the programs name, From Roots to Arts, and its purpose to highlight culture and heritage of residents in public housing at one community center in each of the five boroughs. I became excited when I saw that the residency location for Queens was where I live. Confusion filled my mind because I didn’t understand how I received this email. I didn’t recall ever signing up to be on an emailing list or having any communication with the Public Housing Community Fund. However, receiving the email wasn’t a coincidence to me. The year prior I felt a desire to serve my community with the gift of poetry that God blessed me with. One afternoon on my way to work as a Direct Support Provider, I spoke to the Assistant Director of the community center at the time, about wanting to facilitate free poetry workshops. A year later the Open Call felt aligned and I believed this is what I’m supposed to do. Read more>>
Ellie Gall
When I was 20, I packed my bags and moved from Australia to the US, away from my family and friends with no job lined up. I was thrown right into a stereotypical actress in LA life; multiple auditions a week all over town that you would get the night before and have to memorise. I joined the most outlandish classes I could find, from movement to voice, suddenly my Thursday mornings were spent dancing around a room on Melrose Avenue in an attempt to “take up space” in a movement class. I had thrown myself into one of the most competitive industry towns in the world and I was flailing about trying to make my break. And then 6 months in, I got a self tape for the prequel for a beloved sci-fi franchise called “Stargate”, where I got the chance to audition for the lead role. Two days later, I had booked that role and within a week we were on set filming. This role has been a huge jumping off point for my career in the US and legitimised my potential as an artist in Los Angeles. Read more>>
Jeff & Rocky Rolfzen
In 2023 we sailed our sailboat up to the San Juan Islands on the Washington coast. We had no plans but came with an open heart and found we enjoyed it and decided to stay. We left everything behind that we had in Tacoma which we retrieved later but still arrived and lived at anchor for months before finally settling down and honing in on Lopez Island. Due to our independence on the sailboat people noticed us roasting coffee on board and after we got more established in the community the opportunity to take over the brand of Lopez Island Coffee Roasters came to fruition. Read more>>
Gwenevere Persaud
Starting my nonprofit, & our podcast, were two massive risks that I took. When I first started my nonprofit I was very young, however I was determined to make an impact. In June of 2022, I started a newsletter about marine biology which I called thepersaudcatalog.org. I wrote tirelessly, & worked on articles every day. I rarely took days off, & I’m quite happy that I didn’t. I continued until December of 2022, when I decided that I wanted to scale up my impact, & officially registered it as a nonprofit organization. I got the letter of determination from the IRS 5 days before my birthday while I was in a foreign country, & I still remember the feeling of happiness, & hopefulness for what was to come. Read more>>
Andrea Zoppo
The big risk I took was believing in myself. Through the juggling of part-time jobs, college, and the various co-housing situations many of us endure to afford to live, it seemed to me and my peers that careers were like ghostly leprechauns, pale, lean, and elusive. You could call this time my 20s or awkwardly a Chumbawumba era. You know the song…“ I get knocked out…” It was 2008 and when it came to applying for jobs I was stuck between overqualified and underqualified. With a college degree, 2 years of running programs for nonprofits through AmeriCorps, a myriad of work and volunteer experiences, and over 60 applications, the best I could do was 3 part-time jobs, and hope that one may reveal itself as the elusive leprechaun. Along with the 3 jobs, I also was doing a side hustle hosting birthday parties and teaching the wonders of art, gardening, and nature as a whimsical character named Miss Ladybug, but I did not take it seriously. Slowly one of those jobs, a program manager at a nonprofit, got bigger and bigger until I was at the 35/hr mark after 5 years. With a hopeful heart open for that pot of gold of being a full-time employee with benefits, that Chumbawumba song kept playing… Read more>>
Kendall Blasingame
My biggest risk I would say is diving head first into content creation, and the influencer scene, at such a young age with absolutely no experience or guidance. I started my social media journey at sixteen, but didn’t start taking it seriously until I was eighteen. Read more>>
A’jay Love
I always knew that God had a calling for my life. When I started on my social media journey, I had already faced many personal trials and tribulations while coming into my truth. I understood it would not be easy; nevertheless, I was determined to make a difference with my story, one that would inspire and spark change. Read more>>
Joe Cooley
For as long as I can remember, I’ve loved nature. The serenity, the unpredictability, and the raw beauty of the outdoors have always drawn me in. But as much as I admired it, there was a part of me that hesitated to dive into wildlife photography. The cost of entry, especially for the equipment I’d need, felt like a mountain too high to climb. A good telephoto lens—something essential for wildlife photography—was a significant financial leap for what I thought might just be a hobby. Read more>>
Timmy D
When I first started songwriting, I was still young in high school. I moved on to college not knowing what I wanted to major in, and I felt I had two choices. One choice was being happy and going to school for music and moving to Nashville. The other choice was to transfer to another college to major in History to become a social studies teacher and that is what I decided to do since it was financially stable. I took the risk to earn money to be able to fund my music dreams. Fast forward to today, I am now a career Firefighter/EMT after teaching social studies for three years still funding and pursing my music dream at the same time. I would say my biggest risk was staying on Long Island where I currently live after having multiple opportunities to move to Nashville, I just felt like the times were not right. Read more>>
Divya Negi
I’m taking a big leap right now. As a self-taught designer, I’ve always been fascinated by the idea of art school. So last year, I decided to go all in—I applied for an education loan, used my savings, got into art school, and moved to the US for better education, creative opportunities, and a fresh start. Whether this risk pays off or not will depend on finding a job this year, but I’m determined to make it count. It does feel life-changing. Read more>>
Hannah Bowles
Opening my salon was the biggest risk I have ever taken. I no longer had the option to fail, it was either go out on a limb and take a chance on my craft or stay stagnant where I was. Being the person I am, I wasn’t going to stay stagnant. So opening my own salon it was. Read more>>
Zach Jasperson
I was a police officer for about 10 years and spent a majority of that time working weekend nights around the busiest nightclubs in the country while also being on my departments SWAT team, so risk is something I became inherently use to. In December of 2023, I made the decision to leave the police department. This was a choice that came with it’s own risks because I would no longer be a government employee with stable pay and benefits. About a year later, after some persuasion and motivation from one of my old teammates, I decided to purchase a food truck. I spent about 4 months with him repairing it, rebranding it, and making it road worthy. Burgers by Board Bar was born and is on its way back to that same area I worked in as a cop for so many years. Read more>>
Heather Vandermelen Madison Alderink
We are a mother daughter duo who has always loved to find the hidden gems and one of a kind pieces. We love the thrill of the chase and the feeling of finding “the” piece. We have a knack for curating pieces that you can visualize in your home. For years we had been told we should be in business and help others create a beautiful space unique to them. We both have full time jobs, full plates and little time so this seemed like a pipe dream of sorts. A new antique market opened near one of our homes and we were able to secure a space. We had never done anything like this. We had no idea what people would want, how much they would be willing to spend, how much space we could reasonably afford or fill, yet we jumped in feet first. We started with the mind set that we would present our product they way we decorate our own home. Most of the inventory we started with was in fact items pulled from our personal spaces. We love unique pieces blended with some new and heirloom pieces. We brain stormed a name, set some ground rules for stocking our space and opened Babe Cave Vintage. In a saturated market it felt uncertain and scary. We are having so much fun. It has been a joy to spend time together as mother and daughter growing our business and sharing things we love. Read more>>
Christian White
Deciding to go full-time with music production while I’m still in high school has definitely been one of the biggest risks I’ve taken, but it doesn’t feel like one singular moment—it feels more like a series of small decisions, each one pushing me to go harder, no matter the circumstances. I’m passionate about this to the point where sometimes you want to risk it all, even though I’m still in school. There’s no certainty in this—everything is unpredictable—but I’m trusting that if I keep putting in the work, things will fall into place. Read more>>
Nathalie Kalbach
The question of how an artist has taken risks is fascinating, because choosing to be an artist seems inherently like a path of risk-taking. My journey began with an early setback – in school in Germany, after a wonderfully encouraging art teacher left, their replacement watched me attempt my first sketch and declared, ‘Nathalie, you really have no talent for this.’ So I did what seemed logical – I studied law and became a paralegal, finding meaning in pro bono and asylum seeker cases. Read more>>
Terrance “erv” Ervin
In November 2024, I took a major leap by driving from Richmond, Virginia, to San Antonio, Texas, to fully pursue my art career. Since making that bold move, I’ve been featured in a magazine twice, participated in four art shows, and showcased my work at multiple markets across San Antonio, Austin, and Houston. I’m actively expanding my presence in the Texas art scene, having applied to become a featured artist in several Austin galleries while seeking similar opportunities in San Antonio and Houston. I’m also looking to put together my own art show soon this year. So far, this risk has paid off, and I’m excited to keep growing while I’m in Texas before heading back to Virginia. Read more>>
Nicole Marcus
I was a full-time state employee with holidays off, great PTO and sick leave, as well as good health insurance with no premium. I had been there almost 5 years, and I just wanted something different. I had always told myself I didn’t want to work for someone forever. I wanted something of my own. I was talking with one of my friends who stated she was working as a Family Support Specialist Contractor as a side job for extra cash. Me being me, I looked into it. Every job I’ve ever had has always been on the lines of helping people whether it’s in the medical field, counseling, social work, and/or ministering through praise and worship. So, I applied for the same position, interviewed, and got the job. Being a contractor is very different from being a full-time employee. No benefits, no set schedule, no guaranteed steady income. So, I decided to dip my feet in the water and accept cases here and there to see if I’d like it. I partner with the Department of Family and Children’s in Georgia to work on reunification of families. I work on parenting skills, behavioral skills, counsel, and provide supervision during those visits. Once I got my feet wet, I started to consider transitioning completely over to being a contractor. Read more>>
Melyssa Allen
It is interesting to write this now, as I’m about to take the leap of faith into full-time entrepreneurship! I originally began my business as a way to do local pop-up fitness events, and since I officially started my business in 2019, I have expanded it to include a virtual fitness studio, group coaching community, and corporate health and wellness programs. After writing my book, Healthy Living Doesn’t Have to SUCK, I felt called to start dreaming bigger and imagining myself speaking on stages worldwide and creating positive lifestyle transformations for individuals, communities, and organizations. It is both terrifying AND exciting as I move into working for myself full-time and building my tiny team to support my big dreams, but I’ve realized that if I want to impact the world the way I desire…then it is time for me to take the risk, let my faith be greater than my fear, and turn my small business owner dreams into my full-time reality! Read more>>
Frida Cossio
In 2021, like many others, I found myself at a crossroads. The pandemic had turned life upside down, leaving me furloughed from my Dallas PR job and craving new opportunities. My position with a Dallas agency had restarted slowly, and I felt the urge to challenge myself. Determined to take a leap, I scoured LinkedIn for freelance opportunities that I could do remotely. That’s when I connected with a communications agency based in Pennsylvania and was hired as a PR Specialist. Read more>>
Mitch Lazorko
Making a career change can always be risky. For most of my life I have had more than one job at a time. I enjoyed the security in having several sources of income. In 2020, I found myself with three different jobs. Yoga instructor. Professional musician. Part time photographer. Over time I found having to juggle the logistics of all three were challenging, and I was really interested in making photography my full time focus. With that came the fear of failure. There is a lot of risk in putting all your time and effort into one business. But I came to a point where if I wanted my photography business to grow, I would have to leave my other pursuits behind and go all in. Being a business owner can be scary. There are so many things that can go wrong, but if you don’t try, you’ll never know. In the years that followed, I had to put in a lot of late night hours. Networking meetups, test shoots, workflow adjustments. Today my wife and I run our business and we are happy and comfortable. We do have to work hard, some days are more challenging than others, but I am so glad I took the risk to try this as a career. Life is too short to put off pursuing your dreams. Read more>>
Will Lindsey
On February 7th, 2019, I took the biggest risk of my life and moved to California to pursue a career in acting. I had lived in Florida my entire life, born in West Palm Beach, moved to Orlando for college then Tampa for College. I had never been that far away from family and now moving to a completely different coast and time zone. This was a step that my wife and I were taking that we were incredibly nervous about, but had faith in our craft and our ability to be adaptable that it would work out. Read more>>
Kiara Hargrove
One risk I have taken was building my own skateboard brand and becoming a professional skateboarder. I have been skateboarding for 14 years, starting at the age of 10 on Thanksgiving Day of 2010. I launched my skateboard brand, 1004 Skateboards, during the pandemic in 2021. I took a risk to start this brand because I was supposed to be picked up by another soon-to-be skateboard brand, but due to financial reasons, this did not happen. I recall doing drawings and mockups of potential graphics for this brand that never came to fruition. After this door closed, I told myself I should start brainstorming brand names. I used that closed door to push myself to great heights. Through extensive research, mock-ups, and drawings, I came up with “1004 Skateboards.” The number 1004 stands for “Angel” in Korean, it is my birthday, October 4th, and I am often referred to as an “Angel” by others for my kindness. Moreover, numerous people noticed my constant usage of the 100 Points emoji on social media. This has turned out to be one of the best decisions I have ever made. The 10 deck samples I purchased sold out in 1 week. I created a team with other skateboarders, and we are scaling our brand here in America and worldwide through eCommerce. Read more>>
Brooke Mcpoyle
Almost one year ago, I took one of the biggest risks of my career: transforming how I shared my knowledge by creating a lecture called “The Brain and Breath Connection.” The lecture stemmed from a discovery that reversed challenges in my own body, my family’s, and my clients’. It revealed how our breath, fascia, and brainwaves are interconnected, enabling us to regulate and regenerate health through natural rhythms. Read more>>
Jade Brito
One of the most pivotal risks I’ve taken was leaving the comfort of a corporate career to start my own agency, connect<>culture, in August 2024. I had spent over a decade in brand marketing, holding senior leadership roles at brands like about-face beauty by Halsey and Makeup by Mario. These roles allowed me to refine my expertise and build a network, but deep down, I felt a pull to create something more personal—something that would redefine how brands connect with contemporary culture. Read more>>
Ozi Igbokwe
As my snails hibernate, I’m taking my biggest risk yet. I’ve assembled a dream team to pitch a nature-inspired public art concept, featuring the musical talents of Salif Bamakora and Dianna Lopez – the playlist to my meditation practice – and the visionary Raphael Treza. To be an artist is to have the audacity to claim one’s true calling. Wish me luck! Read more>>
Kimia Shakerpoor
The biggest risk I ever took, was deciding to become a chiropractor.
At UC Davis, I was dead set on the route to medical school. I held a board position in our on campus pre-medical association, I had taken my entrance exam, the MCAT, and was one click away from sending off my application. Read more>>
Rachel Nicol
It was the winter/spring semester of my freshman year at a small university in Northern California in 2022 when I started to come to terms with the fact that I had no idea where I was headed with my life. I’d graduated highschool the year before in the wilderness of British Columbia, where my family now lives, and I headed off to take a popular course at a university my parents had approved for me (fun fact: now I’m a non-practicing licensed lifestyle coach). After the fall semester and that course were over, I decided to return to the school to take general education credits in the beginning of 2022. Seeing everyone around me pursuing their various degrees of education, nursing, or biology, I quickly became discouraged and at a loss for what to do. So I took a gap year after the close of the winter/spring semester and went home to BC to figure out what my next steps were. Read more>>
Melissa Crook
In July 2021 I founded the original portion of The Embracing Layers Network, called The F.E.E.L Podcast (FindingEmpowermentEmbracinglayers). At age 51 I have had a series of experiences that I was learning from, and I knew I wasn’t the only women going through this. I wanted to create a safe space to have conversations about what gets in the way and empowers us to prioritize our wellness and all parts of our health as women. I also wanted younger generations to have a guiding framework to follow so that they could avoid the pitfalls and mistakes so many women in my generation have run into on our journey. Read more>>
Eric See
In March of 2020, like most small businesses in New York City, I was forced to layoff my staff and close the doors to my fledgling cafe and bakery, The Awkward Scone, that had just opened nine months prior. I immediately turned it into a hub as part of a larger network of relief kitchens being used to distribute meals and grocery kits to families and individuals in marginalized communities throughout NYC, Queens and Brooklyn, before being able to open up a few days a week to offer 3rd-party delivery and pick-up orders from a limited menu run by myself and an ex-business partner as an ailing attempt to keep the business alive. Read more>>
Alicia Navarrette
Being an independent creative studio owner is a huge risk in and of itself. The market is over saturated and now inundated with generative content. When I started my studio I was mid-career and midway through grad school studying design. My previous experience had been in marketing and arts non-profit research and development. The degree program I chose was half MBA and half MFA with a heavy dose of systems thinking and design facilitation. Read more>>
Andrey Vlasov
I can’t say that I have taken risks many times in my life; however, there have been pivotal moments where taking those risks proved essential, especially in my journey as a photographer and author that required me to step out of my comfort zone. Let me tell you about one of them. In the very beginning of my travel experiences, I was convinced by a friend to go on a trip abroad just a couple of months after returning from my very first international journey. Before that, I held the stereotype that, like some other people I knew, I should only travel once or twice a year. Read more>>
Fatima Ezzahra Mahdar
The biggest risk I ever took wasn’t about diving into the unknown—though there was plenty of that—but about trusting in something that was not just a career or a dream. Storytelling, especially through animation, is the way I exist. It’s how I express who I am in this world and my ever-evolving journey. One life was never enough for me. I needed to recreate my characters, my worlds, and the ways I exist. And the only way I could do that, the only way that sparked my soul, was through storytelling. Read more>>
Sativa Minerva
I risked the life I knew for the life I desire on multiple occasions. Growing up in a smaller city, I knew I needed to relocate to a large city with bigger opportunities. Music has been my passion for as long as I can remember and when you love something that much you risk it all for it. I left my hometown in pursuit of musical networks and opportunities and made my way to CA. Moving to CA has proven to me the risk was absolutely worth it! Read more>>
Emily Winesberry
I have taken a lot of risks in my life, but I believe the risk of leaving my therapy job in the Bay Area to move from Oakland, Ca. back home to Wichita, Ks. to become a professional artist and private practice mental health therapist was the scariest. I had been working in San Francisco at Conard House, Inc., a community mental health agency providing mental health therapy, case management, money management, and health navigation to our clients. As the years passed, and I made less and less artwork I began to feel a need to create more space and opportunity to work artistically. I found myself wanting to spend more time painting but with the commute into and out of SF for work, and the mental and emotional energy it takes to hold clients full time, I felt that I did not have the reserves to create art. I got the opportunity to move back to Wichita in 2022 and decided to take it. I would be leaving behind a city and region of the world I loved and a job I never dreaded going to in service of my creative spirit. It was a risk to leave my economic stability and begin two new businesses from scratch without solid community and professional support established, but it felt like a risk I needed to take, and I trusted that I would be Ok in the long run. Once I was ready to begin the work of starting my business and working again, I found that I had so much more support that I could have ever imagined. Community and support bloomed around me, and I found what I needed was here and all I had to do was be ready to accept their support and presence. Read more>>
Charlene Holmes
Taking the leap into full-time entrepreneurship was one of the most pivotal risks I’ve ever taken. It wasn’t a decision made overnight but rather the result of years of personal and professional development while balancing a full-time job. I had always been passionate about helping others, and after my bariatric surgery, I felt a deep calling to share my journey and empower others facing similar challenges. However, the idea of leaving the security of my job was daunting. Read more>>
Kyle Jordan May
The biggest risk I’ve ever taken was starting The Kyle Jordan Project while I had a brain tumor. At the time, I didn’t know if I would survive, let alone whether I’d have the strength or time to build something meaningful. It wasn’t just a physical battle—it was mental, emotional, and spiritual. But that diagnosis forced me to reevaluate everything. It hit me that life is short, unpredictable, and far too precious to spend holding back. Read more>>
Gloria Austin
Becoming an entrepreneur was never “the plan”. In 2016 I had Just graduated college with a BS degree in sport management hoping to eventually land an assistant coaching position at a local high school in Tennessee or start a non-profit AAU league. As a former women’s basketball player staying around the game was still in the front of my mind. However I believe God gave me another path. I ended up working the next 5 years as a Sous Chef at Nashville’s Music City Center. I made so many connections with amazing people. Read more>>
Becky Altman
As an executive leadership coach, my mission is to empower leaders to unlock their full potential by deepening awareness, shifting mindsets and behaviors to gain confidence, clarity and the skills necessary to drive themselves, their teams and their organizations forward. Having worked in the nonprofit and corporate space, I have been led by leaders of all types. I experienced leaders who led with ego, credentials and a “know it all” attitude. I also experienced leaders who didn’t quite know what they were doing technically, but were really good people and we all sort of felt bad for them because “they mean well”. Neither inspired me. I didn’t want to be led by fear and intimidation and I didn’t want to be led by someone who couldn’t teach me, guide me, develop me. Read more>>