You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken.

Claudia McConnell

I started my social media platform 4 years ago. As a farm wife, girl mom and affordable fashion finder. I have always enjoyed sharing pictures on socials. I thought why not. Since then it’s become so much more. After developing breast cancer at age 37 and going through that process I’ve found such a great community of supportive instagram friends. It’s given me an outlet for my own growth and well being. When I wasn’t able to work for a year due to surgeries and health, it gave me something to focus on. I’m still growing, learning everyday. Sometimes I feel like I’m not good enough, or young enough to compete with other creators but everyone has their own niche and there is plenty of space. Read more>>

Kevin Le

The biggest risk I’ve ever taken was moving away from my hometown and my family to Los Angeles to pursue a career in acting, stunts, and directing. It was a leap into the unknown—leaving behind the comfort of familiarity for the uncertainty of an industry where success is never guaranteed. I had no safety net, no guarantees, and no clear roadmap, just a passion for storytelling and the willingness to work relentlessly to make it happen. Read more>>

Kaylyn Lovin

When I was 15 I began my career as a runway model, spending years in a career that was fast-paced and demanding in its own way. The transition from modeling to joining the military wasn’t easy, I had to push myself in ways I never had before. Learning how to respond quickly, stay calm under pressure, and help people in real time gave me a sense of purpose that I hadn’t realized I was looking for. It was a big shift, but one that made sense for me. Read more>>

McKenna Kreiling

One of the biggest risks I’ve taken was leaving the familiar comfort of Illinois to pursue my graduate studies in Savannah at SCAD. It wasn’t just a change of scenery—it was a leap into the unknown, with all the uncertainties that come with starting over in a new city and climate. Living with arthritis, I knew the humid environment in Savannah could be unpredictable for my condition, and I was stepping away from a well-established support network. This decision forced me to confront both physical and emotional challenges head-on, but it was also a pivotal moment that underscored my commitment to growth and self-discovery. Read more>>

Scott Schweiger

My fourth studio album ‘Time WIll Tell’ was the first project that I put significant marketing and promotion energy and money into. For the recording of the album, I blocked out time at an amazing recording studio in Seattle, WA called Hall of Justice, owned by Chris Walla of Death Cab for Cutie. I hired incredible studio musicians and engineers to record the album with me. I also hired an amazing videography team based out of Bellingham, WA to record a music video for the title track ‘Time Will Tell’. After nearly 2 years of effort and expense I was ready to release the album. I worked with a band manager to plan a West Coast tour surrounding the album release, and I organized an album release party, and music video watch party at a very nice venue in downtown Seattle. Read more>>

Barbara Feller

Making any sort of significant change, especially a career move, is never easy, however sometimes, taking a risk leads to the most rewarding outcomes. After years of working as a CPA and financial analyst, I decided to step outside my comfort zone and pursue my passion for real estate. It was a leap of faith, leaving behind the familiarity of numbers and spreadsheets to embrace the dynamic world of helping people find their dream homes or embark on the journey of selling their home. While the transition was challenging, the rewards have been immeasurable – building relationships, guiding clients through life-changing decisions, and finding fulfillment in a career that truly inspires me. Read more>>

James Echols

One of the biggest risks when starting my own business was how and when to quit my 9-5 so Tnprintworks will have 100% of my time and energy. After working nearly 12 years in large scale apparel decoration, I started a screenprinting business in 2020 (during Covid), which led to shortages in supplies, delays in shipments and not much demand for our services. I went full-time in 2023, after working and trying my best to juggle both a full work schedule and deadlines for my own customers jobs, it felt like it was time. I automated my systems in 2024 and it took the business one step closer to taking on larger customers and to be able to deliver quality goods in a timely manner. Read more>>

Jason McQuain

The biggest risk I’ve ever taken was moving to New York.

I spent 12 years in D.C. before that, and Florida is where I was raised, but New York? New York was always the city that signified you’d made it. The place where dreams either thrive or die trying. And I was determined to make mine thrive. Read more>>

Rebecca Weinstein Reiki Master Practitioner

There was a moment in my life when I stood at the edge of the unknown, staring into a future that felt both terrifying and exhilarating. I had built a successful career, one that by all external measures seemed fulfilling. But deep inside, I felt an undeniable restlessness. It was as if a quiet voice had been whispering to me for years, nudging me toward something greater, something more aligned with my true purpose. The only problem? I had no idea what that was. Read more>>

Mallory Ennis

Twelve years ago, I found myself at a crossroads—one that would define the trajectory of my entire career. I had just been laid off from an agency, and suddenly, I had two choices: play it safe and take another agency job (one that required a brutal 45-minute commute) or bet on myself and dive headfirst into freelancing. Read more>>

Chelsea Stewart

The biggest risk I have ever taken? Easy answer. Opening a Hot Pilates studio. When I had the idea to open my own space, I didn’t want to tell anyone, I didn’t want to admit that I had this dream, because there was a part of me that didn’t believe I could do it. And then in a moment of delusion, I signed a lease and dove headfirst into the ocean. Read more>>

Quinton White

When I started college, I had no clear direction. I was there simply because it was what I had been told to do, and I figured, ‘Everyone does it, so I might as well, too.’ After a short-lived college football stint, I realized I needed to take my health seriously. During my first few years of undergrad, I lost around 60 pounds and felt better than ever. My roommates started coming to me for fitness advice, and that’s when it clicked—I changed my major and decided to pursue a career in fitness. That decision was the first major risk that set me on this journey. Read more>>

Chris Andreucci

I was born & raised in Ayr, Scotland until I was 19 years old but have lived in Nashville, TN for just over 3 years now. After finishing business school at university, I knew I wanted to make the move to do music full time. It was my passion and my dream to do this. As I started looking at getting visa’s etc to move over to the U.S, COVID-19 hit. It was a scary time, I was unemployed and living back home with my parents. It definitely made me wonder if I had made the right decision to choose the creative space over the corporate world. As COVID eased up a little I managed to find a way into the U.S and I made the daunting move to Nashville, TN. Growing up in Scotland, this was a whole new world. Read more>>

Bryan Reeves

The best things in my life have come to me because I made the unconventional choice, took the path less traveled: my career as a professional relationship coach, the perfect tribe of friends i could have dreamed up for myself, my wife. It all began when, at 26, I was a Captain in the world’s most powerful military, the US Air Force, yet I was miserable. I was dead inside. I could not really laugh. I surely could not cry. I could not feel my life. In late winter 2001, just 9 months before 9/11, I left the Air Force. Read more>>

Eva Leersnyder

After visiting Hawaii in 2022, I decided to move there for a year to experience something new. In May of 2023, my boyfriend, two dogs, and I flew over.

It was a lot of preparation, but we had fun doing it and trusted the process. The move itself was definitely a big risk, and also continuing my dog training in a whole new city from scratch was daunting. Read more>>

Zena O’Connor

I established 2120 Music in 2011, providing management support for Australian country rock artist Lucie Tiger and hosting band shows (Indigo Kicks) and songwriter showcase events in Sydney Australia. Over the last ten years, what started as an artist promotions and management business on a small scale in Australia, has culminated into taking the huge step of moving operations from Australia to the United States and working on a much larger scale. Read more>>

Erica Battle

The biggest risk I’ve ever taken was starting my own business without really knowing what it meant to be a business owner.
I had years of experience working with teachers and school leaders, and I felt confident in that part. But stepping out on my own, building something from the ground up, that was unfamiliar territory. I didn’t have a roadmap, just a strong sense of purpose and the belief that I could figure it out as I went. Read more>>

Miguel Villagra

“Leaving the certainty of medicine to start Adoctorsjourney was the biggest risk I’ve ever taken.”

For most of my life, the path was clear: study hard, get into medical school, complete training, and practice medicine. And I did just that. I spent over a decade becoming a physician, investing years, emotions, and energy into building a clinical career. But somewhere along the way—amid long shifts, endless EMR clicks, and seeing brilliant colleagues burn out—I realized something was missing. We were trained to heal, yet the system often left little room for the physician’s own growth or creativity. I started asking: What if doctors could chart their own paths beyond the traditional system? Read more>>

Kelly Aul

Not all authors are able to share their journey of the entire process between writing chapter one and holding their published book in their hands. The journey is just as important as the end result, if not more so. I want to let you in on some of the behind the scenes in hopes of inspiring any aspiring authors reading this to show just how possible it is for your dreams to become a published reality! Read more>>

Ashley Chin Rigaud

Taking a risk is how I grew my business within the fashion industry. I was young when I reached out to a fellow stylist, he was styling celebrities and I emailed him to see if he needed an intern.

About two weeks later he responded to me and I went to work on my first project for him. It was such a scary moment because I had never formally met him. I just knew of his work and the colleague of his that I would be assisting. Needless to say, this was my big break and opened the floodgates to me styling Claudia Jordan, Teairra Mari, Marisol from Real housewives of Miami, Miami Dolphins former cheerleaders, and so many more. Read more>>

Jamais Seward

Starting my brand, MixingWithMay was a huge leap for me. I’ve always been someone who’s a bit reserved, and the idea of putting myself out there, on a platform where people could hear my voice and see my personality, felt like an out-of-body experience. But I had a vision, and I was the only person who can execute it. Read more>>

Michael Thompson

I think an artist’s path should be littered with the corpses of our failures. Taking a chance can be embarrassing but it’s where the excitement is and the spot where you learn the most. People are afraid of looking stupid but I’m not. I think that anyone who does not embrace their foolishness relinquishes a portion of their power. If you aren’t open to the failure, how will you know the path to move forward? Read more>>

Lovecolor

Ryan: There’s the old adage, “nothing ventured, nothing gained.”  For most of my life, I’ve really taken that to heart.  I’ve taken pretty big risks throughout my life.  From my small, rural farm town, I applied to a prestigious university, as my Hail Mary plan to attend my absolute dream school, and… I got in.  Coming from where I grew up, that definitely felt like a massive risk.  It was very uncharted territory, and it was an entirely different world than that to which I was accustomed.  It opened a new universe to me.  Read more>>

Jael Fehrenbacher

The biggest and scariest risk I have taken is opening myself up to the world of content creation. For a long time I thought everyone on the internet were attention seekers. While that may be the case with some. I find alot of creators to be vulnerable, bold, brave, non-cookie cutter, and intellectual. When I started creating content I was in a really bad place in my life and depression took up a big part of my life. I didn’t know if I was every going to see the hopeful side of life again. The thing about me is, is that whenever I have been unhappy in life I always covered it up by making other people laugh so they couldn’t see my pain. So I took that idea and put it into my videos. Read more>>

Maribel Diaz

Taking a risk. I have taken many risk in my life to get to where i am today. It started with leaving my job at two bunch palm back in 2021, right before covid hit. i was really close to one of the managers that worked there, where i had told him my business ideas and what my plan was on building a retreat. he would tell me the pros and the cons of it, what to be aware of and so much more. i had mentioned to him i had investors who have jumped on board to help create this dream of mine in opening up a retreat where we focused on a 360 wellness. In Functional performance, health and wellness, where we will create a wellness program during their stay depending on what their goal was. May it be pain management, holistic or maybe on their spiritual journey. Read more>>

Nicole Trickey

I took my first improv class in 2012 at The Upfront Theatre in Bellingham, WA. I had no experience in drama but was called to try something new. My friend Ruth took the class with me. It was a buy one get one free improv special. I still remember the day like it was yesterday. We walked in and were greeted by others in the class. I remember a lovely improv teacher named Oona having the group circle up in chairs seated. We went around one at a time and introduced ourselves. She wanted to know our names, if we had ever taken improv, and are reason for taking the class. My answer was, “My name is Nicole, I have no improv or theater experience, and I’m taking the class to help me pursue stand up comedy.” Read more>>

John Mosley

I grew up in California and that’s where I started my business and built my Popular Nobody Brand. I was doing so many different things from education, working behind the chair, photoshoots and so much more. Over time I started to feel like I couldn’t grow anymore so I decided I was going to take my children and move out of the state and start over……and I did. Made the move to Dallas Texas with a clean start and did everything I was doing in California and more without a cap on my creativity and vision. Read more>>

Lauren Arnke

From the moment I started at the Aveda Institute in 2007, I was inspired by a strong sense of purpose. I love being a part of the service community, and hair has allowed me both structure and a creative outlet while still working closely with people. While I have been in many work environments that had wonderful coworkers, education, and opportunities, somehow, I was always left me wanting to create something more; more community, more education, more personal growth, more grounded and more intentional. Sometimes, that has meant taking a risk and having the courage to move on from a space, not knowing the outcome. The latest risk I took was opening my studio. Read more>>

Nia Birt

I quit my job. I was twenty-five years old and just worked for four years as an 8th grade social studies teacher, and in March of 2023, I decided to quit. I have always been an overachiever and I went to college to teach, I thought teaching was the right career choice for me, but it wasn’t. I made the really hard decision to leave my career and focus on myself. After I left, I took some time off to figure out what to do with my life. I had no idea what would be next. I had created a natural hair content page on Instagram the year prior. It started off as a place for me to post photos of my hair and connect with others such as myself that have gone through a self love journey with their hair. After a few months I gained my first 1000 followers!  Read more>>

Dave Asprey

Taking stupid risks is stupid. Taking calculated risks that are worth it is what makes your life worth living. In my 20s I set out to do every single thing that scared me. Not things that were dangerous, things that were scary. And maybe a little dangerous when it was worth it. One of the risks I took was investing millions of dollars into upgrading my biology. When I was overweight and sick my doctor told me to “just lose weight.” If I had followed his advice to continue exercising 90 minutes per day, 6 times a week and eating a low-calorie diet, I’d probably still be fat and sick today. Instead, I experimented. Some things worked. Others didn’t. But if I hadn’t taken those risks, I would never have discovered the Bulletproof Diet or Bulletproof Coffee, which has helped millions of people lose pounds of fat and inflammation. Read more>>

C.R. Florence

I think that my path toward working in the arts could be considered non-traditional. I don’t have a formal education in the arts, but as long as I can remember my being an artist has been a core part of my identitity. I didn’t have an easy childhood and I come from a low-income family with a single mother. I never viewed a degree in the arts as something that was an option for me, and ultimately I dropped out of school and pursued working full time in a long series of jobs that I never really cared for, and that I could never call a career. In the later half of my twenties I found myself with a family of my own – my partner and I have two children – and working at a full-service gas station in the next town over from where we lived on Cape Cod in Massachusetts. Read more>>

Niki Skistimas

I feel like my whole journey has been one risk after another- starting from the time when I decided to pursue drums. There wasn’t a lot of representation then and it was a struggle to be taken seriously and not get discouraged by the amount of arrogant men that were just trying to get down my pants. I persevered. The next major risk was starting a band with my significant other which is usually a super no no and we both knew it, but did it anyway. It absolutely had some down sides as band members never wanted to be the odd one out and business people thought we were too high risk to take a chance on us. The positives far out weigh the negatives though. Read more>>