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.

Jennifer Dawn

In 2017, my life, my path, and my direction completely changed. A serious head injury which resulted in a skull fracture, and a brain bleed – changed everything in an instant. Suddenly, the things I had always taken for granted—my focus, my energy, and my daily rhythm—were replaced by migraines and a heavy fog of cognitive fatigue. Read More>>

Enrique Mendoza

The biggest risk I have taken was deciding to dedicate my life to electroacoustic music. What makes that risk unusual is that I did not discover this field at the beginning of my career. I was already 33 years old and studying in Amsterdam when I encountered electroacoustic music through my mentor, Jos Zwaanenburg. Read More>>

Stephanie Agudelo

One of the biggest risks I’ve ever taken was choosing to pursue a career in the arts. Like many artists, I grew up creating, but there comes a point where you have to decide whether art will remain a passion or become something you truly pursue. I chose the second path, even though it came with uncertainty. Read More>>

Valentina Mejia

Taking risks when creating a business like KEEN FLY has been both exciting and challenging. My husband and I started the company with a vision and a lot of determination, but there were no guarantees of success. Every major decision involved risk,, from investing our savings and purchasing aircraft time to building a brand in a highly competitive market. Read More>> 

Antonio Duran

I am a firm believer that risk is directly correlated to the reward that comes after. High risk does in fact equal high reward. Read More>>

Stephanie Disse

I started Mountaingirl on a whim during one of my trips to Montana about three years ago. Leaving the mountains always made me feel a bit sad, and that’s when inspiration struck. Read More>>

Brittney Adderley

One of the biggest risks I’ve ever taken was becoming a full-time content creator. My name is Brittney Christine and growing up, I always felt pulled toward creativity. I was never the type of student who excelled academically, but I thrived when it came to the arts. Read More>>

Raina Ball

One of the scariest risks I ever took was deciding to pursue doing hair full-time. In the beginning, I played it safe by working a regular job while building my clientele on the side. I spent long days balancing both, trying to provide for my family while chasing a dream that wasn’t guaranteed to work out. Read More>>

Mynesha Hagen

Taking a risk, is one of my favorite things to do because who going to stop you from being great but you ….take the risk, you can get the out come you always wanted. Read More>>

Cadenza The Group

When Cadenza was born in Venezuela in 2013, we had something most artists dream of: a loyal audience, a familiar market, and a stage that felt like home. We were a contemporary string quartet blending classical instruments with pop, rock, and electronic music, and people loved it. Venezuela knew us. We knew Venezuela. Read More>>

Matthew Koman

In 2019, I was living what many coaches would consider the dream. I had the privilege of working alongside some of the biggest names in sports performance. I was helping build The Togethership, a holistic athletic academy for middle school students that I co-founded with people I deeply respected. The momentum was real. The vision was taking shape. Read More>>

Isabel Roloff

I am actually in the middle of taking a risk right now. My dream is to make music, and I have been playing it safe my whole life and haven’t done it yet. Truthfully because it scares me. Even with this dream in the back of my mind, telling me to go for it, I haven’t taken the leap. Read More>>

Erica Rowan

10 years. I had been working at the same company for 10 years, and they treated my time like it was theirs. I hadn’t had a day off, hadn’t had a holiday off in 10. Years. But I knew the job, i loved my coworkers. I knew this pain. Read More>>

Felicity Bienemy

My entire brand has been about intentional risk taking. I am a veteran, I served 7 years. I knew I wanted to be in the beauty industry, but I was active duty. Due to that passion for beauty firing inside me, I took action. Within that action I risked sleep, I attended night classes for 6 months to become a certified esthetician. Read More>>

Rahnda Myers

One of the biggest risks I ever took was opening our first Sola location in 2016. At the time, I was a stay at home mom raising three beautiful children, but “stay at home” doesn’t really describe my life. I was also heavily involved in our family owned convenience store business, working long hours while juggling everything that came with raising active kids. Read More>>

Emily Bond

The biggest risk I’ve taken with building my team was to break away from what was known and simple. I was part of a larger team in a male dominated sport and the women who did join could get lost in the shuffle. I guess it started with just running a weekly practice for fun and to build a community between us. Read More>>

William Hall

This past winter, Abby and Chase called me the day before their Boston wedding to tell me the venue had cancelled. The Boston Public Library had pulled out 24 hours before the ceremony because a major nor’easter was about to hit the city. Their guests had already arrived. The plan was already in motion. Read More>>

Amy Longmoore

In July of 2020, our 17-year-old daughter, Sierra Longmoore, was involved in a car crash and sustained a severe traumatic brain injury (TBI), multiple skull fractures, collapsed lungs, and a mid-brain stroke. Her family was told she would not live through the night. By the grace of God, she made it through. Read More>>

Sima Haddad

Honestly, the biggest risk I took wasn’t quitting a job or investing a ton of money. It was deciding that what I made was actually worth something. I started Sima’s Baking in 2021. It came from a cake I made for my own 45th birthday. Read More>>

Andrea Brown

I took a life changing risk of moving across three states to attend law school as a single mom to a child with special needs. I have had the dream of becoming an attorney since I could remember…I didn’t do so well in undergrad so I was a little unsure of how it was going to go, if I was even going to get accepted. Read More>>

Gloria Herdt

Not many people know the details of how I went out on medical leave in 2024 and never returned to my high-pressure job as the director of teaching and learning at a real estate education company. A life-altering change that set me on the path of devotion to creativity and expression. Read More>>

Cordell Winter

 

My entire life has been a risk. Read More>>

Kerlin Sabogal

The biggest risk I have ever taken was starting a nonprofit organization with no funding, no staff, no major donors, and no guarantee that it would succeed. The Courage to Bee was born from a desire to help at-risk and underserved students, but at the time, I was a single mother trying to balance work, family, and everyday responsibilities. Starting a nonprofit seemed unrealistic. Read More>>

Jonathan Franklin

The risk I took was making a decision to buy a camera or pay my bills. I chose to buy my camera and the rest was history. Read More>>

Jeremiah Brinkley

The biggest risk I’ve ever taken was leaving the company I had been with for 12 years to start Jeremiah Brinkley Music. To understand why that was such a big step, you have to go back a little. Music has been part of my life for as long as I can remember. Read More>>

Ann Selene

Growing up in the Pacific Northwest, I never thought that I would live anywhere else. That was until 2023, when I packed my bags and moved cross-country to San Antonio, Texas. This was one of the biggest risks I had ever taken: to leave behind everything and everyone I had ever known, to chase my dreams as a writer, as well as for love. Read More>>

Ariana Giovanakis

I’ve been a photographer for 17 years and I started exhibiting my photos simultaneously in my country and in different parts of the world. Two years ago, I felt a calling to explore or add other tools to my work, and I wanted to paint them, which represented a risk for me because it was something I had never done before. Read More>>

Christian D. Nelson

I believe filmmaking as a craft is a gift, and as filmmakers, we have a special opportunity to manifest our dreams, stories, and wildest imaginings into something tangible and perceivable for others to share in. With that opportunity comes many challenges and risks, Undertaking a film, in any form, is a daunting prospect. Read More>>

Jonathan Ochart

Starting a business of my own is the biggest risk I’ve ever taken—and I’d do it again in a heartbeat. Leaving behind the security of a traditional 9-to-5 job to build a marketing and public relations agency of my own changed the course of my life forever.  Read More>>

dina torres

The call came without warning. One day I had a job, benefits, security on a hair salon the next day, nothing. After years of experience in the beauty industry, I thought finding another position would be easy. I had the skills, the track record, the passion. But week after week, the rejections kept coming. No callbacks. No offers. Nothing stable. Read More>>

Liese Chavez

A risk I’ve taken as an artist? The project I’m working on presently may be the biggest risk I’ve taken so far. Read More>>

Nicole Nemiroff

One of the biggest risks I’ve taken was opening my business, Nicole’s Beauty. I’ve always believed that growth comes from taking chances. My mindset has always been, ‘What’s the worst that could happen?’ If something doesn’t work out, you learn from it, adjust, and try again. Read More>>

Elesel Hollow

The biggest risk I’ve taken, is choosing this life of music and entertainment permentaly…. I went from working, bouncing around jobs, getting paid under the table, bussing tables, making sandwiches….to a point where I knew, I felt it in my soul what and who I wanted to be, and to be remembered as. Read More>>

Diontae Burden

One of the biggest risks I ever took was driving across the country alone from my hometown of Baltimore to California in just three days. It was mentally, emotionally, and physically challenging, especially doing it on my own. That journey taught me resilience, independence, and showed me that I was far stronger than I ever imagined. Read More>>

 Andrea Cabrera Jakucs

Recently, I took a leap of faith and hired an associate psychotherapist to join my private practice. This has been a long-time dream of mine, but several challenges held me back—including recovering from the Eaton Fire, adjusting to life as a mother of two young children, and overcoming my fears about whether I could provide enough clients to support another therapist. Read More>>

Deb Goldberg

One of the biggest risks I ever took occurred in 1991 when I was 34 years old. At the time, I was unhappily married, owned a small jewelry store, and was raising two young children. I felt deeply conflicted. I knew I wanted a divorce, but I was terrified of making a decision that might disrupt my family. I carried tremendous guilt and uncertainty, and I spent a great deal of time praying for guidance about what direction my life should take. Read More>>

Skully Brandon

In 2020, I decided to quit my job and try to make a living and career in entertainment. The crazy part is, I already had a good-paying full-time job working at Goodyear Tires. My plan was to save up a year’s worth of rent in my savings account. I backed out of quitting my job multiple times and hesitated for a few months due to the fact that i was making absolutely zero dollars from social media while having over 1.2 million  Read More>>

Deana Ward

Twelve years ago, I lost my job at a startup when the funding fell through. I started going on interviews, and with each one, I felt more discouraged. Not because the opportunities weren’t good, but because the prospect of walking into those offices every day felt like walking into a cage. Something in me just couldn’t do it. Read More>> 

Daisy Campos

In 2020, after the pandemic hit, I decided to go all into investing in my photography. I bought courses and followed through with practice on the back end work as well as hands on with shoots & behind the scenes video showing my work. I ended up getting back to back bookings within a month of putting in the work based on what I learned from the courses I took. That same year, I started taking in shoots out of my garage that we turned into my photography studio. After that opened up & I had practice shooting in it. My clients started coming in! Read More>>

Tierney Shirrell

One of the biggest risks I’ve taken was to shift directions and host a Christian personal development conference. In the beginning of my entrepreneurial journey, I was deeply invested in personal growth masterminds, events, and coaching spaces, but something felt off in my spirit. I couldn’t ignore the growing conviction that so much of the industry was centered on self as the source, leaving God out entirely. What had once felt empowering now felt misaligned. Read More>>

Ben Copperwheat

After 15 years living and working in New York City, I made the bold decision to leave and apply for a professor position in the Fibers department at SCAD in Savannah, Georgia. I knew just one person in Savannah, someone I had attended grad school with in the early 2000s, so it truly was starting over from scratch. It was a significant risk to leave behind the city, my friends, and the professional connections I had spent over a decade building. But seven years later, it stands as one of the best decisions I’ve ever made. Read More>> 

 Dr. Monique Charles

In 2020, as the world locked down and everything fell quiet, I sat with a silence I already knew too well. My PhD, “Hallowed Be Thy Grime”, had done the pioneering work of tracing grime’s sonic theology, its sociological weight, its genealogy as Black British cultural formation. The academy had responded by actively not engaging. Not arguing, not debating. Just silence. The kind of silence that tells you your work does not register as serious in their framework, that your methodology does not fit in their silos. Read More>>

Lulu Agan

For years, I fed people for a living. As a Private Chef, I was really good at it because it was a huge passion. I cooked for families, executives, people who had everything, and I gave them something nourishing at the center of their days. It was respected work that paid really well and allowed me to travel the world. Read More>>

Paola Mounla

For years, I built a successful career in the agency world, working as a Creative Director on high-stakes accounts at multinational agencies. While I found success there—even winning a couple of Cannes Lions—I felt a persistent pull toward a brand and creative vision that was entirely my own. I wanted to create jewelry that wasn’t just an accessory, but a standing sculptural art piece that tells a story even when it’s not being worn. So I launched my jewelry brand just a year ago, Atelier Mythique. Read More>>

Christy Merry

Around 1997, back while I was attending Moody Bible Institute in downtown Chicago, I was hanging out in Wicker Park with my friend Edward (aka Baltazar), and attending my first open mic. He was a visual artist who would sometimes attend these events and play the Native American flute. This had been a last-minute plan change and I didn’t attend with any plans to perform. During this event, the Word Salad Open Mic at the Pontiac Cafe, the host Jim Redd asked me if I was a poet and somehow persuaded me to share one of my poems. Read More>>