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.

Shanta Miller White

Life often presents us with unexpected challenges that demand difficult decisions. For me, that moment came after a horrific attack on my child by her bully. As a dedicated salon owner, my career was more than just a job—it reflected my hard work, creativity, and passion. Yet, when faced with the aftermath of my child’s trauma, I knew my role as a mother had to come first. Read more>>

Summer Collins

I was nearing the end of my second internship in the Marine Sciences field, with about three weeks left before leaving the Keys. I was about to say goodbye to this coral restoration internship experience and venture into the uncertain job market. This was right after the peak of COVID-19, and uncertainty still loomed over everything, especially for a 20-year-old. Read more>>

Dennis Sanders

I take risks by putting myself out there. Sharing my words and life experiences by writing what I know. My vulnerability. My compositions. Music etc Read more>>

Lyonne

I was a successful business owner. I have been my own boss since the age of 21, I loved every moment of my work; it was my passion. However, I was having this question arise: Is this really it? Societal conditioning would seem very satisfying after my achievements in a thriving business, a home, and a life enriched by travel, many friends, and much fun. Read more>>

K Hall

I was influenced by my environment not yet a product of it. After a lack luster attempt at college I found myself by in that same environment. I join the Army and enlisted as infantry. I was in 3 fire fights and IED explosion that hit the truck i was driving. My plan was to pass away and leave my mother 400,000 dollars. As I type this now it’s clear that didn’t happened. That risk I took for my mother was actually for me to get my life together. Read more>>

Jason Pitts

This new film, The Forest Through The Trees, was a huge personal risk. The value of my home more than doubled, and I saw the equity in the house. I took a 2nd mortgage to pay for the film. It was a calculated risk, because I believed in myself and my team. Read more>>

Car Gonzalez

Back in 2021, we founded PlebLab with a simple but ambitious mission—supporting great builders in the Bitcoin space and helping them succeed. We quickly found our rhythm, attracting talented developers, founders and fostering a strong community. By 2022, we had successfully raised a small pre-seed round of $290K. I remember thinking at the time that it wasn’t a huge amount of money, but it was meaningful—especially because it was a syndicate raise. That meant multiple investors had put their trust in us, and I felt a deep responsibility to take it seriously and ensure they saw a return. Read more>>

Robin Strayhorn

Some years back I was working as a substitute teacher by day and creating art as much as I could in my spare time. I soon started exhibiting my artwork in various exhibits and eventually landed my first public art commission. Not long afterward, I felt the necessity to obtain a larger space in which to explore the various mediums I enjoyed working with (i.e., ceramics, print-making, painting, sewing, collage and more). I also felt a strong urge to put teaching on hold so that I could make art my focal point and allow it to be my sole source of income. When I decided to move to a large loft in downtown LA in early 2000, it was a big leap of faith because my rent would turn out to be almost double what I was previously paying. Read more>>

Alexa Adamson

Like all good businesses, Alley Cat Ceramics was born in a time of uncertainty. It was March 2020. I had just quit my job as a server and was planning to start at a new restaurant after a week long trip to Philadelphia. My former college professor had started a production pottery studio and had invited me out to see how it operated and if anything could influence my small scale studio practice. At the time, I had two wheels in a 100 square ft, old contractors office turned artist co-op. I made things when I could and occasionally taught classes to friends and family. Read more>>

Alden Hozouri

I began my journey in this industry after pivoting away from a decade-long career in research and medicine. I threw myself head first into whatever I could find, learning the nuances of each step from barista to manager, roaster to green buyer, while launching and piloting my business in parallel at the same time. Read more>>

Blurbird

For me, taking a risk isn’t just about making big, life-changing decisions. It’s about stepping into uncertainty with an open mind and finding opportunities for growth. Moving to the U.S. from Korea after building a solid career was one of the biggest risks I’ve taken. Adjusting to a different culture, a new creative environment, and finding my place in the industry here wasn’t easy. But rather than seeing these challenges as setbacks, I viewed them as chances to push myself further. I didn’t know exactly how things would unfold, but the sense of possibility was exciting. Over time, my network expanded, bringing new opportunities with it. Read more>>

Wyatt Gassiot

As any agent who has entered the industry and attempted to find success can tell you, working towards a consistent flow of clients or even your first client can and does feel impossible at times. For a solid year I felt like I was absolutely spinning my wheels and making ZERO progress other than burning myself out as month after month passed of trying and trying only to be met with what felt like failure. However, one day I decided to switch things up and alter my approach to building my business and creating relationships with prospective clients and the impact was immediate and mind blowing! Read more>>

Stacy Horn

Becoming a business owner was never really on my bucket list. I may be a big dreamer at times. Sure, I’m inspired by people who chase their passions and build a successful life around such pursuits. And yes, I’m in awe of the entrepreneurial stories of risk-takers and adventurers. Those are all great tales to read over a cup of coffee in a cozy armchair or to mull over on a hike in the mountains. But living in Colorado in 2014, I was entirely content to live out my creative soul as a wedding planner for someone else’s company. She was savvy. She gave me opportunity to work in over forty different venues with lovely adventurous couples. I was bringing people’s wedding dreams to life in a range of mountain towns and urban venues around the state. I skied a bit, hiked a bit, loved the vendors I worked with, made it back to Michigan to visit family once or twice a year. Read more>>

Emma Jo Wassink

One of the biggest risks I’ve ever taken was leaving my corporate job to start my own business. It wasn’t just about switching careers—it was about betting on myself, my vision, and the life I wanted to create.

At the time, I had a stable job, but deep down, I knew I wanted more flexibility, creativity, and ownership over my work. When I became pregnant with my first child, that desire became even clearer. I wanted to build something of my own that allowed me to be both an entrepreneur and a present mom. Read more>>

Emelia O’Toole

I scratched my plans to apply for a PhD program to become a full-time fragrance influencer instead.

When I was 10 years old, I decided my life’s plan was to become an English professor and a writer. I knew writing wouldn’t likely pay the bills, so I assumed I would follow in my mother’s footsteps and become a college professor as well. Teaching is an incredible career, I would have summers off to write and to travel, and I would get to live my years out by talking about my favorite writers. For the most part, this life plan stayed on track: I loved all my English classes throughout my school years, went on to study English in college, and even moved overseas to pursue a Master’s in Irish Literature. Read more>>

SHAIRA FRIAS

The biggest risk I’ve taken was stepping up to become the CEO of my company, LUNA MAGIC in order to guide it into a positive direction. In 2023, after years of trying to find a solution, my family and business colleagues saw the writing on the wall and told me that I needed to take charge immediately in order to reset the culture, and to create an environment where the company—and the people within it—could thrive. Read more>>

Scott Woods

My biggest personal and professional risk was building a cultural arts center from scratch.

It started as a lark. In February of 2016 I was giving a speech at a high school in my hometown, Columbus, Ohio, for Black History Month. I had been asked to speak on the history of Black art in Columbus. I took a slightly different route, and treated the occasion as a state of the union address, describing what life was like at that moment in the city for Black artists. Things were rough. While I knew and worked along many artists in various disciplines, you didn’t see us in most of the places where art was happening. We weren’t getting lots of gigs or exhibits, we weren’t getting grants or residencies, none of that. It was as if we didn’t exist. Read more>>

Brianna Ward

The boldest leap I ever took was walking away from my 15-year career to fully embrace the roles of a stay-at-home mom and entrepreneur. It wasn’t a decision I made lightly—leaving behind the stability of a steady paycheck, the familiarity of my routine, and the identity I had built over the years was terrifying. Read more>>

Marissa Boucher

It’s with so much gratitude that I share this – our boudoir & women’s portrait studio, The Boudoir Divas, has been in business for 20 years. We’ve served over 4000 spectacular clients! Many of them have traveled to our studio and even flown with us on our international destination photo shoot adventures. A division we named, Adventuress. Read more>>

ANMOL SINGH

The most significant risk I’ve taken was relocating twice across continents—first from India to London for university, and then making the even bolder move to America with essentially nothing but determination and a business plan.
After completing my studies in London, I felt strongly that America was where I needed to be to achieve my long-term goals. However, the path wasn’t straightforward. Without established connections, existing business operations, or substantial savings beyond what I’d earned through trading and investing, I faced a daunting challenge. To enter the country legally through an investment visa, I invested my entire life savings—over $1 million—to start a business in an industry completely foreign to me. Read more>>

Johnna Devereaux

I had built a thriving business in the financial industry—one that filled my bank account but drained my energy. Success, by all conventional measures, was mine. But something was missing. That realization hit home when I rescued Diego, a shelter puppy who quickly became my world. Read more>>

Dr. Maxine Owusu

As a full-time Emergency Medicine physician and mother, launching STEM Kiddos—an educational brand promoting diversity in STEM—was one of the biggest risks I’ve taken. Amidst an already demanding schedule, I felt a deep urgency to address the lack of representation in both children’s educational content and STEM-related toys, especially for Black and Brown children like my own. The idea was inspired by my kids’ curiosity about my work and their desire to see themselves reflected in the world of medicine. Read more>>

Clayton Ballard

The first big risk was jumping on a Chicago train and landing in Los Angeles. I was miles from home, alone and scared. My spaceship crashed on an alien planet and the aliens looked mean. But soon, new friendships formed, doors opened and opportunities presented themselves. The experience taught me to take chances and the rest will usually work itself out. Read more>>

Mike Jacobs

Risk is a necessary obstacle when it comes to both the creation of art and realizing the person you want to be in life. Our band On The Cinder came together in my senior year of college. I had already been accepted to the Masters program of Education at the University at Buffalo, I wanted to be a social studies teacher. I felt being in the realm of history was a great way for me to understand our country and to recognize what has influenced our society to develop as it has, while also delving into politics that my punk rock heart has always kept a keen interest in. Read more>>

Jordan Knox

Life is full of crossroads, and at every turn, we face a choice—play it safe or take a risk. My journey has been defined by calculated risks, each one shaping my path toward purpose and impact.

It all started with a devastating injury. As a baseball player at the University of Arkansas at Pine Bluff, my dream was to play Division 1 baseball. That dream was nearly shattered when I suffered a season-ending shoulder injury, one that could have ended my career entirely. Rehab was slow, progress was minimal, and doubt crept in. I made my first major risk—I fired my physical therapist and took my recovery into my own hands. It was a bold move, but by the grace of God, my relentless determination paid off. I returned to the field 2.5 months ahead of schedule, proving to myself that calculated risks, backed by faith and hard work, yield extraordinary results. Read more>>

Mason Belcher

Stop me if you’ve heard this one before – I was working in a pastry kitchen that specialized in bulk orders, performing the tasks of 3 people, and still excelling in my role. My former boss was abusive to his staff, cut corners everywhere, and routinely jeopardized the production pipeline of his own company to get what he wanted. I had been working at his company for 4 years by the time I quit, and should have done so sooner, if it were not for his disbelief in my success in what I do now. He tried to guilt trip my two weeks notice into a 3 month notice. Then, 3 days later, I quit on the spot when he insulted my now fiance. Read more>>

Yahli Ambus

I was born and raised in Israel, a small country that makes a lot of noise and has a very small music industry. When I was 18, right after finishing high school, I joined the military band (as an Israeli citizen, you have to join the army at 18 for 2-3 years). The military band was known for having the best young musicians who would go on to become the leading artists in the industry, making it a highly competitive environment. So, right after I finished my service, I took my first risk and decided to fully commit to making a living from music. At first, I still worked as a waitress, but after 8 months, I quit and put all my effort into finding gigs, projects, and sessions. It was hard—I had to play some pretty bad gigs for very little money and carry my drum set to way too many places. Read more>>

Bianca Hammonds

In June 2023, I lost my job as a media executive—a role that had defined my career for years. At first, I did what most people would do: I started applying for every job I was qualified for, convinced that my next opportunity was just around the corner. But after hundreds of applications and only three interviews that led nowhere, I had to face a hard truth—I was at a crossroads. Read more>>

Maggie

At the end of November I decided to leave a secure high level management position overseeing 6 restaurant concepts across three locations to launch my own concept full time. I’ve been developing and working on my private chef and catering concepts on the side for several years how and when I could. I felt that I had gotten all I could out of the mainstream industry and that with the level of time and energy I had committed to my role, I would prefer to focus that time and energy on my own concepts finally. So I gave notice and put all my focus into finally launching my concepts full time. The decision came at a time when I didn’t necessarily have all the ducks in a row that I told myself I needed for years to make that leap, but the decision came ultimately from recognizing that there would never be a perfect time and the stars would likely never be aligned the exact way I hoped. Read more>>

Benjamin Ahadzi

Risk is often the price of growth. For me, the biggest risk I ever took was leaving the familiarity of Glasgow, Scotland, to start a video production business in the United States. It was a leap into the unknown—a decision driven by the feeling that I was stagnant, that I needed more out of life. Read more>>

Lauren (& Jason) Murvine

In the fall of 2021 we (my husband Jason and I with the help of our kids) purchased and planted 660 bare roots and launched our peony farm without any real experience growing peonies.

There is a level of risk and worry in doing something for the first time especially in such a large volume. However, after a series of events, it seemed like a logical step. In 2020 Jason and I purchased my families 7 generation farmhouse on 2.5 acres. We often dreamed about what could do with our acreage down the road that would keep the property in agriculture. We had implemented several test projects on our land (pigs, cut flowers, apple trees) in order to to experiment with what we would want to have. Read more>>

Connie Morrill

My story is complex and emotional. I was a professional dancer for over 20 years, retired moved out of state, going trough a divorce, and started a whole new life. I went from dancing and choreographing, teaching musical theatre to young adults to moving to a state where I had to start all over trying to make a living. I was a card dealer for 4 years trying to make some money to pay my way back home. I became involved in a relationship there and moved to another state where I finally had the opportunity to teach dance again and met a wonderful women at a workout class who believed in me and sponsored me for my first fitness license. I moved again to another state where I became very involved in the fitness industry and was blessed to have people believe me and give me a chance. Read more>>

Casey Landerkin

In the summer of 2021 I quit my full-time office job to become a full-time freelance artist and illustrator. I had been working at this company for about four years at the time, and had been one of the only employees to come into the office during the pandemic. Although I was making artwork at a semi-professional level for years along side working non-related art jobs, I yearned to have more time to work on my own projects. Read more>>

Marty O’Neill

When I was around 21 and still living at home with my parents, I started seeing premium phone lines being advertised on tv and newspapers. They were everywhere. It was new and different. This was back in the days before the internet. I decided to look more into it. In the small print below the adverts were the service providers details so I rang them and asked to speak to the boss of the telecom company. It was a guy called Mark. We hit it off very quickly. I told him I had a savings from my part time bar job that I wanted to invest into something and within a few days he had set me up 100 phone lines to run my very own adult sex chat line business. Read more>>

Chukwudi Ome

One of the biggest risks I took was launching IOYWAV during my second year in university with no financial backing or industry connections. I was investing everything I had—time, energy, and money—into building a brand without a guaranteed return. Designing, producing, and marketing collections while still in school was tough, but it taught me how to navigate challenges and trust my creative instincts. Read more>>

Katie + Lauren Hamden

Lauren and I came into this life together, and have shared the same dream for as long as we can remember. Our initial struggle is one that we feel that most people have to face. And that is overcoming the expectations of people around us sometimes. We talk a lot about hometown syndrome, in essence referring to the drawback that people face from being in their hometown, surrounded preconceptions about what is expected from you and your life. So we can safely say that the biggest risk that we took together, Was the decision to choose our dreams, and leave what felt safe without looking back. Read more>>