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.
Fredo Rodriguez
A risk I token was this right here this brand
N building it up to what it is..
Everyday day by day brick by brick..
I call it a risk bc I’m doing all this work and I’m knowing one day it’s all gonna pay off all them late nights n grinding for this. Read More>>
Judy James
You know, I spent almost my entire life hiding from who I really was.
And I didn’t even realize that’s what I was doing at the time.
I hid through people-pleasing… through denial… by trying to be the “good girl.” I wanted to be perfect, to be liked, to get it all right. I thought if I could just do all the right things, I’d be okay. Read More>>
Mike Moloney
1992, we had just opened out doors.. and were building a business focusing on booking and producing talent for the cruise , casino, and night club industry. An old friend had accepted a position with a Native American tribe, who were opening a casino.. The industry was so new, but it was ripe with opportunity, however to work in the jurisdiction, Read More>>
Natasha Innis
Her love for tattooing began early, but like many young creatives, the road to her dream was anything but straight. Becoming a young single parent meant putting her ambitions on pause while she navigated the challenges of motherhood and self-reinvention. It wasn’t until she discovered the Arizona Tattoo Academy that she was able to lay the groundwork for a new beginning. Read More>>
Adrian Ervin
Adrian Ervin Sr.: Coast-to-Coast Risk Leads to Purpose-Driven Reinvention in Florida
Florida, 2025 — Starting over isn’t easy, but for Adrian Ervin Sr., it was necessary. With no clear plan and no connections waiting, Adrian made the bold decision to relocate to Florida—alone and determined to build something from the ground up. Read More>>
Ryan Leahy
A couple years ago, I took one of the biggest professional risks of my life: I ventured off from the well-worn path of traditional lending to build something that didn’t yet exist — a safer, more structured way to help buyers and sellers transact through seller financing. That became MORE Seller Financing. Read More>>
Courtlyn Jones
One of the biggest risks I’ve taken was deciding to pivot from the creative industry into the fitness and wellness space—and choosing to take my healing into my own hands.
It might not sound like a traditional business risk, but it changed everything: my health, my identity, my leadership, and ultimately the trajectory of my work. Read More>>
Brent Slone
For over two decades, I built a career in the geospatial industry. I worked with some of the biggest names in agriculture and environmental science, Bayer, Syngenta, and BASF, developing cutting-edge solutions using AI, drones, and satellite imagery. I co-authored patents, ran global initiatives, and led multimillion-dollar programs. It was the kind of career you don’t just walk away from. Read More>>
Liva R.J.
I have been taking bold risks in the past, around two major themes: redefining my career a couple of times and moving countries with two suitcases on a hunch, for a total of 13 countries. What can I say, I am an insatiably curious soul. But the biggest risk I ever took is the one that led me to where I am today, both literally and figuratively. Six years ago, I made an offer on a 16th century farmhouse in France’s Loire Valley. Read More>>
Marc Woods
I entered the lane of youth work on a risk. Majority of jobs I’ve had throughout my life have been offered by people feeling I’d be good at certain positions. This left me on several occasions not knowing what I’m doing or even comprehending my target goals. I just show up and learn as I go. The pros of this are that everything I’ve done has come organically. Read More>>
Tanya Cole-Lesnick
Trading My License for Creative Freedom
For three decades, I held the title Licensed Clinical Social Worker. It was more than a credential—it was an identity, a source of pride, and a trusted doorway into meaningful work with countless clients. But when my renewal came due in the spring of 2024, I paused. And in that pause, I felt something shift. Read More>>
Sophia Castuera
The first year I moved to the city, I was lucky enough to know a small handful of folks already. I collaborated with people from college and high school on my first short film, and they brought in folks from their networks to build out the full team. But I was always excited about the idea of meeting new people with whom I could collaborate artistically. Read More>>
Crystal Notez
One day a friend of mine suggested I try out for a part in a children’s play. I agreed to do it because it involved me signing new songs to children and I’m a big kid who loves being silly. When I arrived to the audition I was asked to sing and read the script. I totally forgot that the play would require me to act. I never acted before with a script!! Read More>>
Melinda Johnson
Experiencing divorce was the most challenging life lesson I encountered as a young adult. No one enters marriage with the expectation of divorce. Confronted with this harsh reality, and while living away from family and friends, I turned to the Lord for guidance. Read More>>
Sam Cvetkovski
The day after returning home from a 40+ hour, 82-mile self-supported mountain race, I was emotionally and physically wrecked. Something felt off. That evening over sushi, I turned to my husband and said, “I think I’m getting laid off tomorrow.” I was right. What followed wasn’t just a job loss, but the catalyst for a life-changing decision: to stop chasing stability and finally bet on a passion I’d long buried, coaching. Read More>>
Brian Pickerel
One of the biggest risks I’ve taken was stepping away from full-time pastoral ministry after 18 years. That role had been a huge part of my identity. I loved the people, the rhythm, the sense of calling. But over time, I began to sense God shifting my direction & inviting me to trust Him in a new season where purpose wasn’t defined by a title, but by obedience. Read More>>
Jon Edmondo
Although we think taking risks is far and few between, we actually take small risks every day! Most are non-eventful, but every once in a while, we take a risk that changes our lives. Read More>>
Daniel Kehde
As a playwright/librettist I always take risks. Nothing bores me more than seeing a “brand new innovative production” that’s nothing more than a hodgepodge of stolen ideas and a rehashing of the basic boy meets girl scripts. I suppose one of theriskiest shows I wrote and produced with the late composer Mark Scarpelli was a contemporary opera based on the Dachau War Tribunals. Read More>>
Terrence Smith
In every circle I have been in, I’ve always been the strong one.
The steady presence. The responsible son. The leader. The one people leaned on—at church, at work, at home and in the community. I knew how to hold things down. What I didn’t know was how to fall apart. Read More>>
Danielle Kidd-Shack
Launching Retreat Aroma was one of the biggest risks I’ve taken. I had spent over 20 years working in retail, so while I didn’t come from a traditional business background, I understood the power of product, customer experience, and storytelling. During a difficult period managing my health, candle-making became a personal ritual and eventually, the spark behind Retreat Aroma. Read More>>
Carrie Story
When I look back at the biggest risk I’ve taken in my business, it was launching Project X—our revolutionary line of metal clay products manufactured right here in the United States. Read More>>
Mary Ostrowski
Not too long ago, I realized that risk-taking is a theme that runs through my life. I even have a name for the big ones: my “Sure. Why not?” moments. These are the decisions that didn’t always make logical sense, but something intuitively called me. Answering the call required doing some homework on the opportunity, developing an entrance (and exit) plan, and most importantly – trusting myself. Here are a few notable examples. Read More>>
Damien Burge
I left the with a one-way ticket and very limited Mandarin, lived inside the Shaolin Temple’s foreign-trainee center, and spent every day absorbing centuries-old combat philosophy straight from the source. The gamble was equal parts physical (six hours of daily practice), financial (no guaranteed income), and cultural (total immersion). Read More>>
Heather Martin
I had worked in the events and wedding industry for almost a decade when I decided to venture into a new industry. It was 2021 and still “covid times” and the event world was still trying to get back up and moving. I wanted something with normal hours and less stress. I landed a great senior healthcare sales job and spent time with two different companies over the next 2.5 years. I learned a lot and really threw myself into a whole new industry and network of people. Read More>>
Donna Almendrala
When I was in undergrad, I studied chemistry and took all the pre-med requisites in order to apply to medical school and become a doctor. My school was notoriously competitive in the pre-med field, and I was one of thousands following this path, with nothing really that made me stand out above the rest. It was tough to feel like you were really doing your best, but it’s just not good enough Read More>>
Miguel Cardoso Farano
Miguel Cardof – Taking the Risk to Start Over
Some people chase their dreams. Others survive first – and only then dare to dream.
Miguel Cardof did both. Read More>>
Jillian LaFrance
I remember the moment I decided I was going to speak up and be vulnerable about my own struggles with mental health. It felt risky. I was putting myself out there in a way I hadn’t done before by letting people see the messy, human side of me that I’d kept hidden for a long time. But I knew I couldn’t stay silent if I wanted things to change. Read More>>
Dawna Daigneault
I returned to school in my thirties to earn my first postgraduate degree in counseling psychology. What took most students three years took me six years because my children were very young and my partner worked odd hours.. I loved learning and enjoyed discovering the world of psychological theory. I realized that many great thinkers had developed models of how things help and hurt us as humans. Read More>>
Sierra Greenlee
One of the biggest risks I’ve taken was deciding to pursue photography seriously after my first trip to Spain. At the time, I had just bought my first DSLR to document the trip, mostly thinking I’d be taking landscape photos. But something shifted when I started photographing my friend Carla. I found so much joy in capturing her in these beautiful surroundings—and more than that, I felt a connection to the moment and to the process itself. Read More>>
Fosca Redolfi Tezzat
My dream was always to be a dancer and move to NYC. And so I did. At 19yo I moved across the world from Venice Italy, all alone tackling the big Apple. Some family/friends from back home thought it would be a “great experience” and told me come back whenever that changes. Read More>>
Amber Uhler
In 2021, I stood at a crossroads—figuratively and quite literally. I was nearly 300 pounds, physically exhausted, emotionally depleted, and silently carrying around the weight of so many dreams I’d never dared to chase. But deep down, buried beneath layers of self-doubt and fear, was one dream that refused to die: I wanted to compete in a beauty pageant. Read More>>
Omarr Dansby Averi Lane
In 2020, in the middle of a global pandemic and with no steady income, my co-founder Averi and I made a bold decision: we launched our own fashion brand, Dapper Designer. We were both still in college—me, a full-time student navigating virtual classes and law school applications, and Averi pursuing her accounting degree. On paper, it wasn’t the “right” time to take a leap into entrepreneurship. Read More>>
Allan Saenz
When I moved from Costa Rica to Los Alamos in 2003 with just $2,000, I never imagined I’d one day run an internet company or own an event center. I started by cleaning bikes and later volunteered at a small internet provider to learn everything I could. That led me to eventually purchase the company—now Los Alamos Network—which delivers high-speed fiber and wireless internet to over 3,000 homes and businesses across the region. Read More>>
Brett Parks
Starting my own practice has been one of the bigger risks I have taken in my life, but as a natural risk-taker I am loving this ride. During my time in dental school in San Francisco I used to surf big waves, and committing to surf big waves has a lot of parallels with taking professional risks. When you catch a big wave there is a moment at the very apex of the wave where your body has to commit to dropping into the trough of a two-story size wall of water. Read More>>
Raphaella Silva
One of the risks I’ve taken as an entrepreneur was combining my many practices. I’ve been a multihyphenate for as long as I can remember, and since there wasn’t a specific term to describe people like me, I was often labeled as scattered for moving from one idea to the next. Read More>>
Jordin De La Rosa
After graduating college as a game design major for narrative design. I decided to pivot my focus into becoming a photographer. I was 3 years into working at my retail job at Nike and I said to myself that I’ll take this time to network and get better with my craft. In 2023, I ended up losing my camera and as everything felt like it was crumbling around me, the people around me insisted in starting a GoFundMe, get a new camera and make 2024 your year. Read More>>
Cathy
After years of putting off my therapy licensure, I finally completed my clinical hours, passed the licensing exam, and instead of stepping into a more traditional next chapter, I gave myself permission take a nonlinear path. I put my belongings in storage, placed my home Pilates and Reiki business on hold, and booked a one-way ticket to Nepal. After a year of sitting with the idea, I decided to travel throughout Asia while gradually building my private therapy practice remotely. Read More>>
Erika DeCarlo
I had the privilege of working under a chief engineer at a highly renowned studio, a rare opportunity I was fortunate to seize. My mentor there was exceptionally fair yet uncompromisingly strict, often reminding me and my colleagues that a line of eager individuals stood ready to take our places. He set clear expectations and held firm without wavering, emphasizing that if we wanted to thrive in that environment, we needed to demonstrate our commitment through hard work and maximum effort. Read More>>