Tony Robbins says the #1 human need is certainty, but do you know what the second need is? It’s uncertainty. This tug of war between the competing needs of safety and risk are at the heart of so many dilemmas we face in life and for most folks the goal isn’t to eliminate risk – rather it’s to understand this core human need. In our view, the best way to understand or learn is through stories and so we’ve asked some very talented entrepreneurs and creatives to tell us the stories behind some of the risks they’ve taken.
Alyssa Mancini
We all get stuck in jobs we don’t love and spend time complaining about it. I was bartending for years and so unhappy in the life I was living. During covid I decided to take the leap and explore where my photography business can go. Anyone in the restaurant industry can attest to how difficult it is to leave that fast money life. It hurt at first but having more availability for photo opportunities made me more ‘bookable’ and therefore made my photo business flourish. Taking the leap is definitely a risk but you just have to trust the process. Read more>>
Shelby Green
When I look back on my journey, I realize I moved to New York and started my own dance company all within a couple months. At the time, all of this doesn’t seem like one big decision- just a ton of tiny little decisions compiling. The decision I made a decade ago to be a pursue dance; the decision I made years ago to be a choreographer; the decision I made months ago to move to New York; the decision I made weeks ago to open its own Instagram page; the decision I made 30 seconds ago to look into LLC status for companies. None of these things quite so grand or daring in the moment. I remember each one of these commitments I made along the way and how huge and scary each of them felt. But I think it’s all of these small decisions that turn into big ones and make it feel less like a big risk. Read more>>
Lindsay Jensen-Evans
I’ve always been someone on the fringe… curious about what’s emerging culturally, globally, and spiritually before it becomes mainstream. After 11 years in a career I once loved, leading experiential marketing strategy for a beloved yoga brand across North America—I began to feel deeply disillusioned. I had learned so much about leadership, communication, and personal growth, but eventually found myself burned out, disconnected, and questioning everything. I was a new mom at the time, juggling cross-country travel, performance pressure, and the weight of a culture that equates worth with output. Read more>>
SAYDA DESROSES
The risk I took was taking time off from work to heal trauma from Sexual assault and sexual abuse. Fashion and luxury can be very demanding and difficult, especially as a leader with a large team. I was having panic and anxiety attacks that led me to get professional help. When faced with the reality of being an SA victim in my childhood and teens, it was even more difficult to remain in a chaotic environment. I quit without having another position and focused on my healing. It was even harder than expected to deal with PTSD from the horrible experiences I had hidden in dark corners of my mind. With psychological help and family support, I have come out of that trauma after almost two years. Read more>>
Jay Thomas, Ed.D.
I spent thirty years in education, the last twenty of which were as a professor of education at Aurora University outside of Chicago. My areas of research and teaching were in learning theory, motivation, and research methods. I had published several textbooks, many book chapters, and numerous articles related to my teaching and research, but toward the end of my career, I decided to begin writing about things that interested me outside the classroom, in particular the ways in which learning and teaching and motivation in the development of athletes and artists. Read more>>
Janine O’Brien
So, I grew up in a world that didn’t leave much room for risk. The path was laid out clearly and early (through explicit and implicit messages): go to school, get good grades, go to college, get a stable 9-to-5, get married, have kids. For many people, that’s a fulfilling and beautiful life. But even as a kid, I had a quiet sense that it might not be mine. Read more>>
Kennedeigh Smith
Having gone to Grand Prairie Fine Arts Academy, my path was always clearly paved for the visual arts. I was painting, drawing, and sculpting daily, constantly developing my skills as an artist. Throughout high school, I was building connections and expanding my reach within the local art world. Although I didn’t have a clear direction beyond high school, I knew I wanted to achieve something significant that went beyond painting. Read more>>
Carmin Issa
I never imagined becoming an entrepreneur—until the world shifted in 2020. At the height of the pandemic, I found out I was pregnant. Shortly after, I was diagnosed with an incompetent cervix and placed on modified bed rest. Suddenly, everything slowed down. Luckily, the world had slowed down too. Remote work, once a dream, became my new reality. Read more>>
Nick Ricca
The biggest risk I’ve taken was leaving a full time job and going all in on creative endeavors at the end of 2022. I have been a creative my whole life. From an early age, I wanted to shape my life around the arts. Growing up on Maui, I was in the ocean all the time. Surfing, swimming, paddling. Romping around in the shore break shooting pictures of waves and my friends on waterproof point and shoots. I discovered a love for capturing the moments around me, the things that I loved to do everyday. I pursued a career as a surf photographer/videographer throughout high school and beyond. Read more>>
Dean Love
As a filmmaker, my whole career has been about taking risks. I’ve traveled through war zones, and dangerous places like landmine territories, scuba diving on wrecks and crawling into unexplored caves. I was shot at twice in Honduras and I fought off a Komodo Dragon with a big stick in Komodo, Indonesia. But, one of my first big risks came early on in my career. Read more>>
Wendy Paquette
One of the most defining risks I’ve ever taken wasn’t about money, location, or relationship; it was about truth. The truth of who I really am and what I came here to do.
There came a moment in my life, a deeply visceral, raw, and unshakably clear moment, when I experienced what many would call an “awakening.” It wasn’t pretty or polished. It wasn’t something you could package with a certificate or frame on a wall. It was an undeniable inner knowing that I had access to something far beyond traditional logic, something that could recode human potential at the root level. Read more>>
Emily Brown
One of the biggest risks I ever took was walking away from the life I thought I was supposed to want. I was a CEO’s wife, a stay-at-home mom, and from the outside, everything looked shiny and picture-perfect. But on the inside, I felt like I was disappearing. I had spent so many years meeting the expectations of others, trying to be what a “good woman” is supposed to be—supportive, selfless, agreeable. I was afraid to want more. Read more>>
Ryan Ryskamp
My wife and I have always been more comfortable with risk than our family or friends. When we started our first business, Social Supply, we quit our jobs. Living of credit cards that also paid for materials and tools seemed more stressful for the people that cared about us than it really ever phased her and I. We did this with a son, moved 5 different times, 3 of those times back in with family to save money. And when credit cards ran out, we would have our parents add us as a card holder which would widen our credit to debt ratio opening up our options again to apply for a new card. Eventually we paid everything off, started to see cash in the bank account, and it wasn’t so risky anymore. Read more>>
Edwin Salgado
A significant risk that changed the trajectory of my life came after high school when deciding what school to attend. As an aspiring, young artist I wanted to immediately go to an Art school in order to develop my passion and enter a career surrounded by likeminded creatives. I took a chance of applying to The School of Art Institute of Chicago, which I, to my surprise, was accepted to attend. My excitement was through the roof. Mi mama came with me for orientation. Read more>>
Jean-Pierre Verdijo
Choosing to make art your profession is perhaps the most rewarding and risky decision a person can make.
To me it feels essential to live true to my deepest desire. To model that to my children and community.
All choices in life come with sacrifice, there can be an illusion that if we choose something close to our heart that can be avoided. Read more>>
Monica Gagne
As a kid I used to hide in my closet and cry. Deep down, I carried this quiet, powerful knowing that one day I would figure out how to heal myself, and then it would be my mission to help others heal too. But as I grew older, I got swept up in the way society conditions women to be “good girls” – to please others at our own expense, to be realistic, to set our dreams aside and follow the path that looks safe on the outside. I tried to go along with it. I got the 9-5, I played the part, but inside, I was crumbling and barely holding it together. I reached a point in my twenties where I didn’t want to be on this earth anymore, and I knew something seriously had to change. So I took the biggest risk of my life: I quit my job and threw myself fully into my healing journey. I had no clear roadmap, no guarantee it would work, and no one really understood what I was doing. But I knew I couldn’t keep living a life that wasn’t mine. Read more>>
Paola Ramos
One of the biggest risks I’ve ever taken was leaving my old job to start my own business. I was only 23 at the time, still trying to figure out who I was, navigating personal challenges, and stepping into a season of self-discovery. What made it even scarier was that the salon I left wasn’t just a job, it was where I had planted my roots. Read More>>
Johanna Hartley
Honestly, one of the biggest risks I’ve ever taken wasn’t about money or moving or starting a business — it was deciding to share something deeply personal: my son’s medical journey.
I’ve spent years building a successful chiropractic practice, and that’s always felt like “safe ground” for me. I know how to show up in that space. I know how to lead. But when my son was born with a rare birth defect, everything shifted. Suddenly I was the one sitting across from the doctor, overwhelmed and scared, trying to make impossible decisions. Read more>>
Cam Beemer
When i graduated in 2016 i took the music route not knowing which way life would take me. I decided not to attend college and bet on myself throughout the years. I started making beats building myself each year to get where i was. In 2022 i quit my job and became a full time musician to engineer and produce music. The journey had ups and downs with plenty obstacles but i stuck to it. Read more>>
Blake Ellis
One of the biggest risks I’ve taken in my career was starting a professional Shakespeare company in my hometown. I remember when the pandemic had upended all our lives, and my wife and I found ourselves in Fresno, CA, wondering what to do next. There was a brief, but very serious consideration that perhaps it was time to find a normal job. But my wife, ever the optimist, encouraged me to keep my chin up and press onward. “Something will turn around. We don’t see it yet, but it’s coming.” Read more>>
Peter West
As with any small business, growing pains involve taking risks! When I hired my second round of employees to keep up with a influx of new work, I wasn’t sure if I could keep enough work in front of them but I knew if we always did our best our customers would tell their friends and the jobs would keep coming. Sometimes purchasing equipment and hiring more employees forces you to think outside the box and solve the problem in front of you. It has kept me from being comfortable and stagnant in your business. Read more>>
Heather Ruth
In December 2021, our son Rowan was born. He was everything we ever dreamed he’d be and more. We were quickly and utterly obsessed with his every little detail. All we wanted to do was be with him. Soak in his tiny features. Learn his cues. Stare at his sweetness. Even sleep deprived, we were the happiest we’d ever been as a family of three. Read more>>
Zarina Moreno
I decided to take a risk to quit my full time job without a backup plan at the beginning of this year.
I had left my previous job for this new one because it had seemed like such a good opportunity at the moment: a better pay, close to home, and it aligned with my professional goals. I didn’t go looking for this opportunity either, it was offered to me, so I thought the Universe was speaking and saying, “hey! I’ve got bigger plans for you!”. So I went with it. It represented what so many of us, especially first-generation Latinx individuals, had consistently fought for. A chance at a better life with more stability and professional success. A chance to do and be more. So I never saw coming what happened next. Read more>>
Rachael O’Brien
When I took my first yoga class in 2011, I immediately knew I wanted to be an instructor and studio owner—this felt like my calling. While all my friends went off to college, I took a different path. I dropped out, enrolled in a 200-hour yoga teacher training the next year, and began teaching at just 19 years old. Read more>>
Priscilla Lima Ledesma
The biggest risk I’ve ever taken was leaving my secure 9-to-5 job to pursue what some might have called “fun hobbies.” On the surface, it seemed reckless. I was walking away from a stable paycheck, health benefits, and a predictable life. For years, I had built a solid career, but I knew in my gut that I was meant to do more than just sit at a desk. My real passion lay in photography, music, and education, and I felt this burning need to turn them into my life’s work. Read more>>
Azariah Reese
In Summer of 2025, I received a gift that would be the biggest source of stress and originator of luck in my life. This gift happened to be a violin, larger than the average, with a creme Brule color palette with light brown worn finger board, an ivory tailpiece and light brown wood on the body of the instrument. Read more>>
Maggie Andreis
After completing my graduate studies at The Ohio State University in 2022 and wrapping up my college soccer career, I was ready for a change—a new city, a new job, a new way of life. Most of my family and friends were still in Ohio or Michigan, and though my husband was with me in Ohio, he wasn’t in a position to relocate yet. But after six years in the same place, I was itching to go. Ohio State had been a great environment for college and grad school, but it had also been a place of personal struggle. I was ready to spread my wings and figure out who I was outside of soccer, school, and the stress that came with it. Read more>>
Dawn Cook Ronningen
After my first book was published I decided I wanted the independence to self publish.
My focus is antique textiles which is a niche audience so leaving the safety of a publisher also meant 100% of the risk was mine. It was up to me to finance, manage, deliver and promote my next two books. Read more>>
Chrystal Robinson
The biggest risk I have ever taken was to relocate to Cleveland Ohio, for a position as Executive Director of the International Women’s Air & Space Museum after being divorced, I wanted a fresh start. I bought a house, closed my art gallery, and relocated my life to run the museum in late March 2025. Read more>>
Scott Holt
I am usually full of bad ideas but ideas none the less and ideas are fun, right?! Friends and family have been talking me out of my half-cocked schemes all my life. Sometimes when I feel strongly enough about one I go for it anyway. This one was at the beginning of my comedy life (bad idea). I wanted to paddle board across the Hudson River in a business suit during the morning commute. I shoved off down by the ferry station in Morris Canal Park, Jersey City, NJ. I had a briefcase, coffee, and fake papers exactly like the rest of the daily travelers. Everyone in my life was telling me this plan would have me dead or in jail. Except my wife. A bit unusual for her. I found out later she had taken out a term life insurance policy on me, so that’s real love, right?! Read more>>
Coleen Speaks
My whole life is a risk. As a business owner you rely on yourself, your abilities to follow through and get it done. It can be very scary, isolating especially when not just supporting yourself but your family, and your employees. When I initially took the step to move from New Orleans and start my own catering/hospitality business(es), the first risk was the idea and leaving a stable job, then it was where I was going to do it. I ultimately choose Raleigh as it was an emerging market and felt like I could make a bigger impact in that area. Read more>>
JenniLee
You know, my biggest risk was probably deciding to step out from behind the scenes and build my own business. I’d spent over 20 years styling celebrities—Lauryn Hill, Greta Gerwig, Scarlett Johansson—always being the invisible person, making everyone else look amazing. I’m actually quite introverted and got into styling because it was specifically behind the camera. Read more>>
Michele Stokes
For over 20 years, I had built a career in corporate sales within the professional beauty industry. It was safe, stable, and predictable—but I realized that stability was also limiting my ability to truly make an impact.
I took a leap of faith, walking away from the security of a large corporate role to join a startup, Alinea Hair USA, because I believed in its mission to innovate and empower stylists—not just creatively, but financially. It was risky. Startups don’t come with guarantees. But that risk opened doors I never imagined. Read more>>
Karla Putts
Back in 2019, I took one of the biggest leaps of faith in my life. I felt really strongly that God was leading us to leave California, so my husband and I packed up our three dogs and everything we could fit into an RV and headed to Arkansas. It was a huge shift—my whole family stayed behind, and we didn’t really know what we were walking into. Everything felt new and unfamiliar, but somehow, even in the uncertainty, it felt like the right thing to do. Read more>>
Kathy Cruts
A big risk I experienced early on in my business subsequently demanded that I face a challenge I was certain was beyond me. It forced me to confront everything – how I had spent over a decade at a previous job that offered security but not creative freedom, and how past memories were shaping and limiting my belief system now which was keeping me small. Something that seemed so innocent, a great first editorial gig that required me to take a boat across the channel and do a team shoot from boat to island, ended up being the recipe of a perfect storm. Read more>>
Lori Haddox
I first discovered My Gym as a mom to an 18 month old with a lot of energy and a zest for learning new things. A friend actually suggested going to a free trial class and while they didn’t enroll, we loved it and it became our special time together since I worked late most nights. Fast forward to a few years later, the owners were putting together a franchase for My Gym and I wanted to be a part of that. Read more>>
Adrienne Smith
In 2018, I took a leap of faith to change up my life entirely. I had been living in Boston, a legal professional working in higher ed. I wasn’t passionate about what I was doing and was looking for a new career that would enable me to work with people one-on-one and have my own business. I was a little stuck though, and wasn’t sure what that new career would be, so to clear my mind and be open to the possibilities I decided to break out of my life for a bit. I quit my job, put my stuff in storage, and spent 16 mos. having this amazing adventure traveling around Italy and New Zealand. I learned how to be more flexible, more resourceful, and to have trust. Once I returned, I trained for a career in sound healing. Now I’m a sound healing practitioner living in Sante Fe, New Mexico (a place I had never even visited!) and I love what I do! Read more>>
Anna ‘Sunshine’ Manring
Right now, I run Soul Flow Teaches, a wellness brand rooted in embodiment, meditation, and intuitive healing. But starting it was a huge risk. I stepped into this space with nothing but a vision — no investors, no perfect plan, and no guarantee it would work. Read more>>
Damon Sheeley
A few years ago, I made what most people would consider a questionable life choice: leaving a stable, full-time job in my 40s to pursue art full-time.
I had a dependable career in retail logistics and supply chain management, with predictable hours, health insurance, and a 401(k) I probably never contributed enough to. Married, kids, plenty of debt and all the usual life chaos. On the side, I’d been making art for years. Nights once everyone went to bed, lunch breaks, weekends, and whatever scraps of time I could find in between. It started as a passion project I never seriously imagined could become more, until it did. Putting my art into the world for the first time was freeing, and it quietly changed everything. Read more>>
Alexis Rogers
I started my journey in becoming a social worker in 2014 as a freshman at the University of North Carolina at Pembroke while working full time at AT&T. My husband and I are high school sweethearts and at the time we had our very first apartment in which I chose to commute full time to complete my degree in social work. Interesting enough I began my degree as a major in criminal justice with a minor of social work wanting to get into the field of forensic social work or legislative social work positions. Read more>>
Eileen Murphy
I’ve never been one to take big risks. Uncertainty used to feel like something to avoid, not explore.
Then COVID happened.
While others turned to sourdough starters and ukuleles, I coped by doing more work. Work felt safe—predictable, productive, within my control. It distracted me from the news, from the loneliness of virtual everything, from the aching unknowns. Read more>>
Mike and Tiffany Squires
Tiffany and I started Kell Squires Pastures in April 2022, a year after getting married. As first-generation farmers we wanted to be part of the local food economy especially during the pandemic. We began to understand the fragility of the industrial food system and wanted to take more control over our health. After a string of health issues that culminated in surgery we realized an animal-based diet worked best for me, and the most economical way to make that happen would be to raise the animals ourselves. Starting the farm was a risk that has paid off in many ways. Read more>>
Karin Busch
One of the biggest risks I’ve ever taken is the one I’m currently in the middle of: moving from Germany to Los Angeles to rebuild my photography business from the ground up – this time in a completely new country.
My love for California began when I was 17, during a high school exchange year in Napa. A trip to LA back then lit something in me – the sun, the ocean, the creative energy – it just felt like home. Still, I spent years playing it safe. I worked as an event planner and pursued photography on the side until the pandemic hit and I lost my job. That moment gave me the courage to finally go all in. I built a thriving photography business in Germany, capturing weddings and portraits full of emotion and story. Read more>>
Jasmine Nicolét Johnson
For me, entrepreneurship is all about taking risks every single day. It’s choosing to believe in myself, even when the path isn’t clear and the outcome isn’t guaranteed. Every decision I make, whether it’s launching a new product, investing back into my business, or simply showing up consistently is a leap of faith. It’s not always easy, but I’ve learned that growth doesn’t come from playing it safe. It comes from pushing forward, trusting the process, and staying committed to the vision no matter what. Read more>>