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.
Amy Pickering
Betting on myself was a risk taken!
When starting a new travel business,
your first concern is how to get clients. Read More>>
Jennifer Campbell
My first daughter was born in 1992. Due to being born with a lung disease, I was told she wouldn’t live through her first 3 days, and I would hold her for the first time after she had died. She’s 33 now, so things worked out; however, through a very traumatic yet positive situation, I learned that things could have gone better in my situation if I had had support. Read More>>
Joy Rhine
At the beginning of this year, I quit my job at an agency, flew solo to Africa to summit Kilimanjaro with a bunch of strangers from around the world that I had never met, and returned to start my own freelance business where I now work on contract basis with clients. I think a lot of us sit back and think to ourselves, “man I wish I could do that” but the reality is, you probably can, its just a matter of how badly you want it. If there is anyone to take a risk on, it might as well be yourself. Read More>>
Dr. Geoff Dold, DPT
Deciding to work for myself and open my own business was the biggest risk I’ve ever taken. It all started right before I got married. My wife and I were living in San Diego, but we decided to move back home to the Bay Area after the wedding to be closer to family. Read More>>
Nicholas Bailey
My biggest risk is taking my side hustle and entering it into an actual LLC. I went from making 3k a year doing my little hobby to triple the numbers so far in the past year. It’s a lot to returning customers and a bigger network. Read More>>
Kirk Anderson
I was a drummer since age 13. In 2015 I suffered a right arm paralysis and underwent emergency neck surgery where they fused 4 collapsed cervicale vertebra. It left me with a dead nerve in my right are, effectively ending my drumming career. Music is a big part of who I am, so I had a choice to make. Give it up or reinvent myself. so i took the risk and ventured into singing… It has been the most fun I have ever had! Read More>>
AIDEE MEZA
A huge and life-changing risk I took was leaving my previous field: Esthetics.
I had invested thousands of dollars into school, courses, and obtaining my esthetician license. I had a clear plan and vision for my career. Read More>>
Stephanie Garbaczewski
When Steph and Erica decided to launch NIKS Medical Spa, it was more than just starting another business — it was a leap of faith into a highly competitive and evolving aesthetic market. Both of them had solid careers as dermatology-trained physician assistants and previously emergency department medical provider, with years of experience and steady jobs. Read More>>
MaryBeth Timothy
I think being a professional artist is all about taking risks. There is no “regular” paycheck to fall back on for one thing. I took a major risk in 2018 when I quit my “9-5” job and became a full-time artist. That same year, my husband was laid off, and we made the scary decision to just go all in with our art business! It has been quite a journey, but I wouldn’t have it any other way. Read More>>
Pamela Merritt
The biggest risk I have taken was when I made the decision to walk away from my guaranteed and successful position in the Fortune 500 Corporation I was working for and start a new career from scratch. I went from working in a traditional corporate America marketing department to flying solo as a freelance designer. It took a few years to finally hone my career into upscale Interior Designer and Artist Read More>>
James Jones IV
One of the biggest risks I’ve ever taken was at the age of 19. I made the decision to walk away from college football and leave my home in Mississippi to move across the country to California. It was during the height of the COVID-19 pandemic, I had no job lined up, and just $3,500 to my name — but I had a dream and a deep belief in my purpose. Read More>>
Sarah Marshank
I didn’t set out to disappear. I just needed a break.
At the time, I was teaching fifth grade at a private religious school while simultaneously completing my master’s degree in the History and Philosophy of Education. I was deeply committed to my career as an educator, to my students — whom I adored — while feeling increasingly disoriented in my inner life. Read More>>
Patricia Fox
There was a moment—a quiet, holy pause—where I stood at a crossroads with nothing but a whisper from God and a stirring in my soul. That’s how Ja’ja Chews was born. Not out of strategy, not out of certainty, but out of crying out in desperation. Read More>>
Asia Farrd
“From Motown to the Metroplex: The Rise of Juggernaut Ent Media”
Born and raised in Detroit, the cradle of Motown, Me Asia Farrd I grew up with soul music in my blood and a vision in her heart. Watching legends come and go from the city that defined a sound, I dreamed not just of making music—but of owning the label . Read More>>
DJ Cova
Before the world knew me as the founder of Tweak Music Tips, I was just DJ Cova—a kid with a deep love for beats, blends, and turning dancefloors into unforgettable experiences. I lived for the turntables, spending countless hours producing edits and remixing tracks that would light up any party. Read More>>
Stacy Santos
Risk…that thing which we know may not yield any good results but we feel compelled to do that thing anyway! For me, one of the biggest risks I have taken is moving to New York City at the age of 54 to pursue my lifelong dream of dancing! As a single mother of two adult children ages 27 and 30, a nurse of thirty-one years, and a US Army Reserve Nurse Corps Veteran, Read More>>
Soulara Sevier
From as early as I can remember, I’ve been drawn to helping people. Maybe it’s because I’m the third child of six—born into a family dynamic that demanded observation, empathy, and a kind of instinctive leadership. I found myself constantly aware of the needs around me. I noticed how people leaned in when they spoke to me, how they opened up. Even at a young age, complete strangers would share their deepest challenges with me—Read More>>
Jared Lang
Ever since I was a kid, I was obsessed with climbing trees. I had a personal motto even back then: ‘I will always find a way to the top.’ That mindset stuck with me through life. Read More>>
Mia Soto
Let’s kick this off with a fun fact: nearly all of my profound triumphs are simply a result of taking an impulsive risk that I deemed worthy enough. The launch of my writing career? I got brave at the encouragement of my sophomore English teacher (thank you, Mr. Manning), submitted a few pieces to my school literary magazine, and won first place in both prose and poetry (unfortunately, I never got the $100 prize I was promised… bummer). Read More>>
Archie Smith
Betting on myself has probably been one of the toughest and best decisions I could have ever made. I think its human nature to be a bit scared about all of the things that could possibly go wrong when leaving the security of a steady income to pursue the thing you know that you were placed here to do. Those thoughts can be overwhelming at times, but I had to come to a place in my life where my fear of NOT taking the chance due to wondering “what if this doesn’t work”?, was not louder than my faith. Read More>>
Tyler Kreis
Back in 2014, I took what felt like a leap of faith by partnering with my father-in-law to flip our first house. I didn’t know it at the time, but that single decision would set off a chain of events that changed the entire trajectory of my life. I quickly discovered a real passion for real estate. That drive led me to earn my license in 2018, and within a few years, I became one of the top investor acquisition specialists in the Dallas-Fort Worth area. Read More>>
Annette A.
I went on maternity leave and never returned to my 9 to 5. It was no longer meant for me. My whole life had shifted as a new parent and it was time for my work environment to shift too. This pushed me to find alternatives and take social media seriously. Though I had done Brand Ambassador work in past, I never had it in me to leave the security of working a standard full time job. Read More>>
Peniel Cromwell
The biggest risk I am taking is preparing to go to Kenya to teach Freestyle Rap Therapy to people in one of the Refugee camps. The origin to story to this risk is that I’ve been doing Freestyle Rap Therapy in low income neighborhoods as well as the Juvenile Intervention Center, which impacting so many youth has led me to prepare to Journey overseas to do work on an international level. I believe this is part of my calling in playin a role in a greater picture that will set the catalyst for many. Read More>>
Madeline Stump
I grew up in a town just outside of Columbus, Ohio. At the time, it was somewhere between rural and suburban, but growing fast. Very white-picket-fence/white and wealthy type of area. To this day, the town prizes itself as among the greatest areas in Ohio to “raise a family”. Or more accurately a very specific type of family….In this town, I grew up as an extremely closeted transgender girl. I won’t go into every detail of my childhood, except to mention one particularly risky/life-changing moment: the day I came out publicly as transgender. Read More>>
May (Tianyang) Yu
One of the biggest risks I’ve taken was pivoting from a full-time classical performance path to a Music Business master’s program at NYU. On paper, it might not seem like a huge leap, since I’m still in music, but it meant a complete shift of both perspective and my role in the industry. Read More>>