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.
Bayberry Shah
Harris Tweed Journey
While traveling in Scotland, I fell in love with the landscapes, people and Harris Tweed, which I already knew from my grandmother’s generation. She gave me her Harris Tweed suit and I still wear the jacket. Such a beautiful, durable fabric and the exact opposite of fast fashion. Read More>>
Crystal Moreland
I grew up in a very small town in the heart of the Midwest where everyone knows your name (and your business). It’s a place where majority of people think the same and conform to “traditional” standards and ideas of living, and those that thrive are the ones that never stray outside the lines.Read More>>
Catalina Prado
The biggest risk I’ve ever taken? Leaving everything I knew behind.
A few years ago, I packed my entire life into two suitcases and moved from Chile to the United States — accompanied by my partner, Carlos Iturrieta — along with my voice, my experience, and a dream I refused to let go of. Read More>>
Joshua Diolosa
My whole life has been a risk. When I was a teenager I found out that during my mom’s pregnancy with me she was told she should have an abortion. That stuck with me. I always figured if God wants me here it must be for something worth being alive for. That way of thinking began my life-long pursuit of the extraordinary. My goal is to be as unsafe as possible, because I don’t believe our purpose is to be safe and comfortable. Safe and comfortable is for the average. Read More>>
Amanda Hill
From the age of four I knew I had a gift for styling hair. I could not keep my hands out of it. Babysitters, family members, barbies, friends, any head of hair I could get my hands on.
Every part of becoming a stylist was captivating to me but my favorite part was watching how hairstylist made people feel. As a young child, I loved observing while my mother got her hair done. Read More>>
Javier Cabrero
Risks aren’t always about money. Sometimes, the biggest leap is about trust. I have found that trusting yourself to take the plunge and trusting someone else to jump with you is a type of risk like no other. For me, risk has shown up as a series of moments where I had to trust own instincts even where there was not a clear path of how to do something or even work with someone. Read More>>
Johann Heemurz
One of the biggest, life-changing risks I ever took was leaving everything behind family, stability, and a sense of safety to chase a vision only I could see. I was kicked out of my parents’ home and found myself homeless in the heart of Manhattan. No backup plan. No safety net. Just faith, paint, and raw determination. Read More>>
Jan Taylor
Being in your own business is always a risk. Leaving a secure job to follow your crazy dream is a risk, but so worthwhile. When you take that risk, you must be prepared to commit. In my case, I was young and naive and not really thinking about the future or goals, but I followed that dream and it paid off. I think it takes a special person to quit their job and start their own business. The risk is scary, but if you commit it can become an amazing life. Read More>>
Shannon Tipton
Before opening my metaphysical shop, I owned and operated a counseling practice, working closely with individuals facing mental health challenges and substance use disorders. Over time, I found myself grappling with the complexities of human behavior and began to question whether I was still making a meaningful impact in the lives of those I served. Read More>>
Meg Landis
One of the biggest risks I’ve ever taken in my life was when my business partner and I opened our studio during peak variant/over crowded hospitals/mandatory masking times during the pandemic in February 2021. We were both feeling very confined and dissatisfied by the limitations at the traditional/corporate salon where we both worked and wanted to further our careers in a way that aligned with our personal values. Read More>>
Dr Jillian Imilkowski
One of the biggest risks I’ve taken was opening a five-room medical clinic in Chula Vista, CA less than a year after passing my board exams. At the time, I had very little savings, no business background, and moderate clinical experience. Most would have waited, built more capital, gained more experience, but I had a vision and I knew I didn’t want to wait years to bring it to life. Read More>>
Tina Bararian
I moved to New York to study at The Martha Graham School, and I was always a perfectionist, I think that comes with being an Iranian. I always thought I needed to spend my whole life on educating myself and training before I start creating and choreographing. I’ve spent years training and graduating from different dance schools and continuously applying and getting into different programs thinking that no matter how many schools I go to I’d still need more knowledge and training to become a better dance artist. Read More>>
Clare Morin
I took a risk last year, when I took a sabbatical and stepped away from my career for five months. Unlike regular sabbaticals, I didn’t have a job to return to. I was stepping into the unknown. Read More>>
Venus Liles
One of the biggest risks I’ve taken was leaving my comfortable, stable corporate job to pursue full-time entrepreneurship with my law firm, Liles Law. Read More>>
Aigner Cruesoe
I took a risk by starting my catering business. I stepped out on faith. I had no clue how to get clients or if anyone would even hire me. I took the risk, because I have a passion for cooking and that’s what I love to do. I also didn’t want to work for anyone else. Read More>>
Jocelyn Meadows
For years, I lived a life of dual devotion — spending my days teaching fifth graders in a public school classroom and my evenings tending to the wild creatures of western North Carolina. Read More>>
Brandon Hall
The biggest risk I’ve taken was walking away from a steady agency job to start my own design business. After seven years, I found myself feeling stuck—pouring my heart into the work while others took the credit, and the paycheck didn’t match the effort. I believe in paying your dues, but I also believe in knowing your worth. It took courage to leave the familiar behind, but choosing myself was the first step toward building a career with purpose, passion, and pride. Read More>>
Lynnae Thompson
Opening my own aesthetics practice wasn’t just a career change—it was one of the biggest risks I’ve ever taken. I walked away from the security of bedside nursing to build something entirely my own, with no guarantees that it would work. I knew I was stepping into an industry that many people don’t fully understand, and I was doing it in a way that stayed true to my values: integrity, healing, and empowerment over hype. Read More>>
Clemy Clarke
When the world shut down in 2020, most people hit pause. I hit record.
Making a film during a global lockdown felt impossible. Production companies weren’t picking up projects, travel was restricted, and I couldn’t safely leave my home — but I still had a deep desire to create. So I took a chance and started making “Hi How Are You?”, a feature film, entirely from home (now available to rent/purchase on Prime Video US). Read More>>
Karen Widas
I took a risk.
Not the kind you read about in headlines, but the kind that keeps you up at night wondering, What if this doesn’t work?
I had a great career in the utility industry. Sixteen years of stability (mostly – they always seemed to be “restructuring”), smart colleagues, and leadership I respected. I did everything “right”—graduated with an Electrical Engineering degree from Michigan Tech, built a family, and worked hard. Life was steady. Read More>>
Amy Havens
When I moved to Santa Barbara in 2001, I only knew two people — my fiancee and his mother. I wanted to start my own Pilates studio, but I didn’t know anyone in town. “How can I start a studio without knowing anyone? How will I get clients?” Well, I trusted myself. I knew that ‘if you build it, they will come’. So, that’s what I did. Read More>>
Carolina Lopez
I didn’t come from beauty. I came from tech.
I went to school for Chemical and Materials Science Engineering because I was good at it. I liked solving hard problems. I liked being the person people came to when no one else could figure it out. Over 10 years, I built a reputation. I was known. I had career momentum, a stable paycheck, benefits, leadership opportunities.. Everything people associate with “making it.” Read More>>
Joe Gallo
Opening this business was a huge risk, financially and emotionally. It took so much work and money to make this all happen. I am so grateful for all my business partners and staff for helping make this dream a reality Read More>>
Craig Price
In the mid-nineties, I packed up my truck and moved to Texas. I didn’t have a job lined up, and I didn’t know a single person in the city—I just knew I had to get out and start fresh. I was tired of the snow, tired of the cold, and ready for something different. Moving to a big city was a leap, but one I felt I had to take. Read More>>
Angel Yang
I used to have a 9 to 5 job where I worked as a medical animator. I grew up in a culture that valued the mindset of stability and certainty. However, I was extremely unhappy and unfulfilled with that lifestyle. Because I could feel my creative and entrepreneurial side wanting to come out, so I decided to go to graduate school for a different life, one with more creativity. Read More>>