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.
TIMOTHY CONNOLLY
When I moved from Glen Cove NY to Henderson NV in 2018 much of my old life stayed behind. Having been a lead singer and bandleader for an innovative award-winning band in Long Island and New York City was no small thing for me to jettison. We were trailblazers from 2002 til 2015 during a time when no other bands in our scene took the kinds of chances than we did. Bonds that developed among our bandmates became badges-of-honor. I’ll always remember times with them. Self-destructive nightlife stopped being fun though and I had allowed myself to be surrounded by enablers when I knew deep down inside that I deserved much better than that. Read more>>
Georgann Bunny Low
I’ve never been hamstrung by a desire for security. As a result, my life has been a journey toward ever deeper expression of my own truth through art, writing, music and now teaching. I frankly have never cared a lot about money. Oh well, to be utterly truthful i love having money, but have never gone out of my way to get hold of it. I do, however, get out of my own way in order to communicate with people because I love people. Oh ! Not everyone, but I like to give them a smile and a chuckle whenever possible. That’s because I’ve found so much joy in just being alive. Read more>>
Lindsey Johnston
I first started my yoga adventure over a decade ago. I started practicing yoga and knew within six months this is exactly what I needed to do with my life. Yoga had changed the way I showed up as a wife as a mother as a human all around. After I did my teacher training having three kids at home a husband that worked what felt like 1 million hours a week. I did my teacher training in a summer 220 hours. Shortly after I was done with my teacher training, I decided to host yoga classes in my shed at my house! Read more>>
Andrei Tone
One of the biggest risks I ever took was launching Tone Films in Tulsa—a bold leap into the saturated and competitive world of video production. At the time, I had a successful career in corporate consulting and accounting. On paper, it made no sense to walk away from stability and dive into the creative space. But I’ve always believed that the greatest rewards live just beyond the edge of calculated risk. Read more>>
ALONSO GADEA
When we I decided to go sign my own clients it was in the midst of COVID there was people looking for marketing talent digitally i knew it was the moment to strike so I liquidated my life savings to finance getting my first clients and hiring freelancers & not cut corners. Read more>>
Lynn Tran
I started my business during late 2019 and early 2020. If you get it right, yes, during the Covid 19 pandemic. I was a high school senior back then. I was bored with online classes and due to having too much free time, I decided to open an online jewelry business. I started to find sources of jewelry aboard, buy it, and ship it to America. The shipping process back then was long due to the pandemic. It took over months for me to receive my package from China. I used all my birthday and holiday money toward buying jewelry, lots of them, and shipping directly from China for an affordable price. Everyone keeps asking why I decided to take this risk when I don’t even know if anyone even wants to buy my jewelry. Read more>>
Barry Davis Jr
Opening my barbershop during movie was the biggest risk I’ve ever taken. It was a time of uncertainty and of course I had no idea the world was about to shut down and I was already invested. With worry of catching the virus and maintaining my business and home life was definitely difficult but we made it and still standing 5 years later. Read more>>
Hala Elkliai
At the age of 16, I moved from Bergamo, Italy, to the United States in pursuit of a better future. With no clear path ahead, I spent the next few years working various jobs to support myself. By 19, I discovered a passion for the beauty industry—an industry where I could express creativity while making others feel confident and cared for. Read more>>
Yussy McManus
I am a firm believer in risk taking!! Without that mindset, I never would have taken the plunge to start my first business. Though I have always been partial to risk taking, I dove in headfirst to my first major risk in 2015. I decided to quit my great job as Lead Interior Designer at a decorated design firm in Naples, Florida, sell my house, and move to San Antonio, TX to start my very first business. My husband, Travis, and I made the move together, not knowing anyone or much about San Antonio other than I loved the area and had a dream to run my own interior design business and industry experience. We began flipping houses, which brought in many customers in the residential and commercial sectors and lead to many interior design awards for my work. We also opened a construction company to aid with my design firm. Read more>>
Jeff Saint Dic
Since childhood, I’ve been captivated by movies—especially action, adventure, drama, sci-fi, suspense, and sports films. Acting felt like a distant dream. I didn’t attend acting school, and my family struggled financially, so moving to Los Angeles seemed out of reach. Read more>>
Maral Porretta
For over 15 years, I was deep in the world of fashion retail — the fast-paced, high-energy, goal-driven kind. I worked my way up at Aritzia, eventually becoming a business manager. It was the kind of job that, on paper, looked like success: the title, the salary, the respect. I’d “made it.” But the truth? I was drained. Read more>>
Alicia Permenter
For over 13 years, I built a meaningful career in education. I earned my Master’s degree, completed my administrator certification, and poured my heart into shaping learning experiences that mattered. I was proud of the work. It served its purpose. It made an impact. Read more>>
David Wilson
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I was born and raised in Westfield, New Jersey, where I lived, attended school, and was a Boy Scout until I turned 18 and entered the United States Air Force in 1987 as a Computer Programmer. Read more>>
Julio Rodriguez
To be honest, betting on myself is the biggest risk I’ve ever taken—especially in an industry as uncertain as the one I’m trying to break into. I didn’t come from a privileged background, and choosing to pursue a career in a field where success isn’t guaranteed is both risky and, at times, terrifying. Read more>>
Ashley Stevens
For the last 15 years, I’ve been in the beauty industry—starting in North Carolina, working as a licensed cosmetologist. I spent over a decade at one of the most successful high-end salons in the area. I had built a great reputation, a loyal clientele, and what many would consider a dream job. But deep down, I knew I wanted something more—something of my own. Read more>>
Cherlyn Reeves
I started working for a mowing company right out of college where I brought my degree in Landscape Architecture to the company to offer outdoor living services to their current list of mow clients. We grew the company so much that it became very popular to the point that everyone was wanting our services in the Tulsa Metro area. Read more>>
Alyssa Bryan
Before I start with the risks, I must provide background.
The risks and endeavors I’ve chosen are supported by overcoming, resilience, and persistency… the need for those actions in this life, as we all know to succeed, thrive, and/or survive.
I enjoy the Reba quote, “I must have had my mamma’s will and God’s amazing grace!” Read more>>
LABONEE MOHANTA
One of the biggest and most life-changing risks I have taken was leaving my financially secure and hard-earned career as an actuary to pursue being a full-time Kathak artist. For years, I tried to do both. I was working full-time in a corporate actuarial job while simultaneously dancing full-time in every other available hour — rehearsing and performing in my Guru’s dance company, teaching at his institution, managing one of its largest centers, and building my solo career. It was fulfilling but exhausting, and each year the pull toward devoting myself entirely to dance grew stronger. Read more>>
Moises
One of the biggest risks I took was deciding to tell the stories of underground musicians, on my own terms, with my own gear, and with no budget. After a few months the pandemic hit, I saw some of the most talented musicians I knew struggling, not just financially, but emotionally and artistically. Gigs disappeared, and with them, visibility. That’s when I decided to start 4Beat Media. I took my camera, my passion for music, and began producing mini-documentaries, live sessions, and interviews. It started with friends, but the mission grew bigger: to highlight artists who were being overlooked by mainstream media. Read more>>
Hannah Helton
Starting Aire – A Blowdry Bar was a bold leap of faith in a city already filled with hair salons. Quitting the stability of a 9-to-5 job to pursue entrepreneurship meant betting on a vision that stood out—offering a specialized, blowout-focused experience that Hattiesburg hadn’t seen before. It was a risk stepping into a saturated market, but one driven by a passion for beauty, a belief in quality service, and the desire to fill a gap in the local industry. This journey has been about trusting instincts, embracing uncertainty, and committing fully to building something unique from the ground up. Read more>>
Tallie Medel
I teach clown. (a level of theater! be not afraid) I’m still getting used to telling people what I do, even though I Love My Job. We’re all the fool, inextricable from our existence, and the admittance sets everybody free. There’s beautiful philosophy around it all (“The clown is a poet who is also an orangutan.” -Steven J. Linsner), yet in practice it’s profoundly stupid. You get to see the best of people. Read more>>
Heather Hopper
Back in 2009, I was teaching third grade at Lakehill Preparatory School in East Dallas. At that time, I was honored to be awarded the East Dallas Teacher of the Year award for Elementary School. During the awards luncheon, two ladies spoke about teaching adaptive yoga through a program called Yoga for the Special Child. My dad and I looked at each other and he spoke aloud what I was thinking… that god was speaking to me about what I needed to do to be of service to our community. Read more>>
Josh Holland
I’m quitting my dayjob to do music full time..I have worked at a factory for nearly twenty years. I have been performing 2/3 times a week locally at bars/venues for the last 12 years..just recently I have had viral videos on Tik Tok and IG and they have opened up more booking opportunities. I have been traveling and making more money..it’s a scary to lose that security and health insurance but the factory is an unhealthy environment, and a soul draining job that pays little to nothing compared to what I make playing covers in bars. I am starting make a little money off streaming also. My goal is to take this extra time and hammer down on content for my original music and also spend more time with my family.i want to focus on writing more also. Read more>>
Alisha Childress
Being me is my risk story. In a world and community of business and competitors, it’ is natural for people to do anything to get to the top, to close a deal, or to win. Business can be transactional and often lacking sincerity, authenticity, and humanity. Over the years as I’ve grown and become more confident and secure in who I am and in my purpose, I have leaned into who I am – a gem, rough around the edges, embodying energy, and a healer in my community. Read more>>
Kyle Visin
When my business partners (Kyle Visin & Emily Foley) and I (Addison Clarke) decided to take a leap and open our own group fitness studio, we never imagined that we’d be taking a second leap almost 7 years down the line and franchising that business to provide the opportunity for other entrepreneurs to create their dream job using our model. Read more>>
Nedric Armstrong
Coming out of college with a degree in music business, I had what a lot of people might call a “perfect start.” I’d worked my way into some solid internships, networked like crazy, and survived my fair share of unpaid gigs just to get my foot in the door. Eventually, that work paid off—I landed interviews, then offers, from two well-known record labels in L.A. On paper, it was everything I thought I wanted: the chance to be behind the scenes of big-name tours, album launches, branding campaigns. The kind of stuff I used to dream about. Read more>>
Rhonda Krick
One of the biggest risks I’ve ever taken was walking away from a secure, 20-year career at a hospital to pursue a long-held dream: running my own private practice. I started my career as a registered dietitian 25 years ago. My first job was at a long-term care facility in New York, but soon after, I moved to Los Angeles and landed a position at Cedars-Sinai Medical Center. I ended up staying there for two decades. From the beginning, I had a vision of one day opening my own practice. My dad owned his own accounting business, so I grew up watching the entrepreneurial mindset in action—and I always felt that same drive within me. But I also knew I needed more experience, more confidence, and a deeper understanding of the field before taking that leap. Read more>>
Kelsey Pearman
as a biologist to picking a master’s program halfway across the country, to changing careers. They just made sense and there were clear rewards associated with each: new field experiences with new species, an MS in Biological Sciences with a fantastic advisor, and a career that’s more conducive to our family’s schedule. Read more>>
Scott Currie
Moving to San Miguel de Allende, Mexico was one of the biggest risks I’ve ever taken. I was following my girlfriend at the time (we are married now) to move to a new country I didn’t really know. I left behind my family, friends, and a sense of security, to step into the unknown. I had just finished graduate school and didn’t have a clear path after graduating. Moving to a new county definite had many moments of doubt, fear, and discomfort. Read more>>
Michaela McKenzie
I thank you all so much for reaching out to me for an interview. I am very blessed once again for this opportunity.
I am Michaela “Mikki” McKenzie—a proud Montgomery, AL native, a multi-hyphenate artist, educator, and a 2024 graduate of Alabama State University, where I had the honor of serving as Miss Theatre and Dance. I am a dance filmmaker, choreographer, and founder of TUTUs and Testimonies and MIKArts Youth Arts Program, both of which reflect my passion for using the arts as a tool to uplift and empower communities—especially Black youth. Read more>>
Marissa Coronel
I had just gotten the keys to my new apartment, which at the time was a blessing based on the current situation of recently going through a rough divorce with a 10 year old and an 8 month old. I had been assisting for my amazing boss/mentor at the time being and I knew I needed more income and more free time, so I can support my kid’s but also be present for them. I had asked him to rent me a chair at his salon so I can have my current client’s take me more serious, since I was just building my clientele! Unfortunately that did not work for me as everyone had already seeing me as an assistant, I believe I was still being treated as one. Read more>>
Meagan Glover
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I wanted to take a moment to personally share the story behind my recent business rebrand.
After receiving a cease and desist from another business regarding the previous name, I was faced with a difficult decision. While I didn’t want to change the name I had built, I knew that spending time and money battling a legal dispute was not the best use of my energy or resources. Read more>>
Fennella Like Whoa
I recently took a leap of faith and moved to Sierra Leone, West Africa, where my roots are. Although it’s often considered one of the world’s poorest countries, it holds deep meaning for me. Over the past few years, I’ve visited frequently and felt a growing desire to contribute in a meaningful, creative way. Even while living in the U.S., my mind was always filled with ideas for how I could make an impact in Sierra Leone. This move is a risk, but I believe Africa is not just the future — Africa is the now. Read more>>
Celeste Brooks
My background is in science and business—I earned my biology degree from UC Berkeley and later completed an MBA at St. Mary’s College in Moraga. I then spent over 25 years in corporate America working in sales, marketing, and business development roles for Fortune 500 companies. My life was very achievement-focused: success, performance, growth—the energy was always go, go, go. And for a long time, that served me well. Read more>>
James Coons
The biggest risk I took would have to be when I left the job I was making 2-3 thousand dollars a week, to become an assistant making $700 a week. I had returned home from performing overseas and knew that I was done performing as I didn’t have the excitement that I once had so I got a job in Beverly Hills at a spa. It wasn’t what I had thought I would be doing, but the money was great, was easy to get off work so was able to still travel and could enjoy life a bit. After being there a bit, I really started missing the entertainment industry, but didn’t really know where I belonged if I wasn’t going to be a performer, so I started looking at other possibilities when I saw an assistant position at Bloc Talent Agency. Read more>>
Amy Letcher
Like so many stories we hear nowadays, this one starts in the pandemic. It was a pretty unremarkable day in a pretty remarkable year, midway through 2020, when a friend reached out needing help.
She had an audition, her character was supposed to be from New Zealand, and she’d never done a Kiwi accent before. Read more>>
Tony Corong
Before Levels Training came to life, the path getting here was anything but easy. Just two years prior, I was knee-deep in applying to PT school; juggling part-time work under Stretch Lab, my own training business that was under a different name, and as a PT aide all while finishing up prerequisite classes. Best believe that this routine was consuming me. Read more>>
Amy & Jesse Quiroz
Taking risk….. This seems to be in any aspect of being a small business owner, right? Like most entrepreneurs/small business owners, there is always that assessment of whether you take the risk. For us, it all started out with my procrastination of what to get my wife for Christmas. I knew that she had a love for crafting, so I quickly jumped on Amazon and bought her a Cricut. She started using it to make what she called unwelcome mats. And to make the templates, she was using the Cricut. This is where our first risk came about. Amy wanted to expand and sell these mats at our local farmers’ market. Amy took the risk and paid for the vendor fee purchased supplies like tents and tables for our booth. Read more>>