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.

Paige Thom

There are two pivotal risks that truly define my journey in business. The first was born out of 2020. Like so many, I found myself suddenly laid off from my corporate event planning role, staring at a blank slate in the middle of a global shutdown. With no prior wedding experience (and every logical reason not to) I decided to launch a wedding planning business. Read more>>

Shawn Marshall

Not all of the risks I’ve taken have had positive outcomes, but some of the biggest have led to the life-changing events of my life. After earning both a bachelor’s and master’s degree in architecture and working in the field for nearly 20 years, I made the bold decision to leave architecture altogether and return to school once more, this time to become a teacher. Read more>>

Amanda Habrowski

Honestly? The biggest risk I ever took was packing up my life and moving across the country alone, betting it all on a career I’d been grinding at for 20 years. No backup plan, no support system, just me, my experience, and a whole lot of guts. Read more>>

Ladi (aka Bay or BowlBay) Oyewo

The biggest risk I’ve taken in my career was walking away from a secure and well paying job as a Mechanical Engineer to pursue music full time. On paper I had everything people told me I was supposed to want, but something felt incomplete. Growing up I was always that kid making beats on the cafeteria table. Read more>>

Chiara Padejka

My debut independent feature length film Rope Tied has no doubt been the greatest risk of my career so far. Making movies is a privilege, but in the midst of it, every decision, whether creative, technical, or financial, feels like life or death. There is no retaking the test. Read more>>

Jeremy Taubman

Since beginning my recovery from addiction on January 29, 2003, I have proudly and openly shared my story with anyone who wanted to know the real me—baggage and all. With the publication of my book, Remix Recovery: Leading a Brave Space, I took that openness to another level, essentially announcing to the world that I have a history of addiction. Read more>>

Maurene Schuler

A few years ago, I took one of the biggest risks of my life: I co-founded Central Coast Justice, a female-led legal support business serving San Luis Obispo County. At the time, I had very little experience in the legal support industry. I convinced my dear friend who had tons of experience to be my partner and teach me what she knows. Read more>>

Tanner MARKER

Risk’ The biggest risk for me is the same as many small business owners, walking away from stability in a career, in this case from oil field to all in on coffee. Read more>>

TRISTAN RAY

The biggest risk I’ve taken was walking away from stability to chase a dream I buried nearly two decades ago. After high school I left music behind and built a career in Hollywood, working at Sony Pictures and later at Entertainment 360 where I supported artists like Julianne Moore, Daniel Kaluuya, and Salma Hayek Pinault. On paper, it looked like I had it all. Read more>>

Max Gleason

Since May of 2020 I have had my painting studio in one half of a converted hay barn on a rural vineyard property. The other half of the building has had various uses and tenants during that time. Then in 2024 the other side of my studio building became available, the previous tenant having vacated. Read more>>

Kristen Suraci

When I decided to turn Saucy Suraci from just a passion project into a formal business, I knew it meant taking on real risk. For years, Saucy Suraci had been my creative outlet—a place to share food, coffee, and small business spotlights in a fun, authentic way. But as the page grew, I started to see the potential to build it into something bigger. Read more>>

Karmen Paley

In June of this year, I was on a working vacation in Florida. As I sat in the backyard of my friend’s house, which is essentially an exotic plant sanctuary, time slowed down. All of a sudden, I had a moment to do nothing. At the time, I was working for one of the largest matchmaking companies in America. Read more>>

Christina Rondeau

A Risk I Took One of the biggest risks I’ve taken in my life wasn’t inside the ring—it was outside of it. When I was just 20 years old, I opened my own martial arts and fitness business. Read more>>

Karsten Bie Jensen

More than 17 years ago my wife and I got an opportunity to invest in a guesthouse in the Maldives. I had previously been on a business trip to the Maldives due to my background as a high end chef, product developer and consultant. A Danish company asked me to join them. Checking the local reef fish was one of our targets. Read more>>

Chris Gladin

I worked as a Nurse Manager during COVID. I had a successful career, but I was really unhappy with my job. Typical corporate downfall feeling unappreciated, overworked, lack of work life balance, and I felt trapped. During that time I day dreamed about what it would be like to run my own business. Read more>>

Markus Martinez

I saw this phrase somewhere: “If you want the life that no one has, you have to do things no one wants to do.” That often means taking risks that people around you might think of but never act on. I’ve always been passionate about music. I started DJing at 16, but I never took it to the next level. Read more>>

Dr. Wendolyn Robinson

At a certain point in most careers, one reaches a milestone that requires action. Not merely whether to accept a promotion but, whether to move completely and support a new phase in life. I took such a risk when I walked away from a position as a subprime contractor. Read more>>

Sophia Whiteman

Before 2025, I was running my bookkeeping business on the side while also working a job with steady pay. The industry I was in was new to Oklahoma and constantly changing- rules and regulations seemed to shift every few months. The work had its benefits, but I knew I was meant for something bigger. Read more>>

Paige Wanamaker

The biggest risk I’ve taken so far was when I decided to take my side hustle full-time. At the time, I was 1 year post-grad with a Business Marketing degree (shoutout Brock School of Business!) , working full time for a local artist – doing everything and anything business related. Read more>>

Destinee Mackin

Deciding to enter a pageant was the biggest risk I had ever taken. The uncertainty was terrifying: would I win, or would I not place at all? Unfortunately, I didn’t place either time, but the experience was invaluable. I learned so many important lessons and gained a level of confidence I never had before. Read more>>

Katrina Coffelt

Awestruck Family Outfitters began with nothing more than a love of travel and a friendship that, at the time, was still pretty new. Neither of us had formal experience in the travel industry, but we shared a sense that travel could be more than just a getaway—it could shape families, build connections, and leave a mark on hearts for a lifetime. Read more>>

Nikki Napolitano

Honestly, one of the biggest risks I’ve ever taken was leaving a really comfortable, well-paying job as a cocktail waitress on the Las Vegas Strip to start my very first career position as a substance abuse counselor. To put it in perspective—I had just finished my bachelor’s degree, which took me ten years to complete because I wasn’t the traditional student. Read more>>

Shazad Carbaidwala

Everything I have done has been taking a risk from my former professional bodybuilding career to authoring two books to being a FEMA officer, to walking in federal institutions and speaking with people whom have been institutionalized. ‘Be comfortable in being uncomfortable in life’ I have taken on many initiatives to preserve my late dad’s legacy. Read more>>

Ruut DeMeo

Just six months ago, I quit my job to start a nonprofit organization. I didn’t know how it would pan out, only that I had a burning (and big) vision to champion women artists like myself, that just wouldn’t leave me alone. I’d been working in education for some time, teaching in classrooms, writing curriculum, and working in instructional design. Read more>>

Dana Hooper

After being an partner at the biggest law firm in the country, it seemed like a secure no brainer to stay for the long haul. But, after 17 years of private practice, I knew there was something bigger out there for me. Read more>>

Lynette Toma

When I opened my sound healing studio, it wasn’t during a time of certainty or stability—it was during the middle of COVID. The world felt shut down. Businesses were closing their doors, people were isolating, and there was so much fear about what was safe and what wasn’t. Common sense would have said, “Wait. This isn’t the time.” But something inside me said otherwise. Read more>>

Des McAdam

The first risk I took was taking the jump of leaving the world of the music industry and going towards my dream of getting licensed in cosmetology. That was back in 2020, for obvious reasons the world had suddenly stopped, everything I wanted to do seemed to come to a halt but I signed up, and went into it with a positive mind set. Read more>>

Maria Leonard Olsen

At age 50, I got divorced and sober, became and empty nester, and was living alone for the first time in my life. As a gift to myself for my 50th birthday, I tried 50 new things in my 50th year to determine how I wanted to live the next chapter of my life. Read more>>

Kate Mazza

One of life’s most meaningful lessons for me has been that taking a risk always pays off. Whether it be through business success, a project detail coming out even better than imagined, or a hard-earned lesson, I’ve learned that rolling the dice on myself or a cool design idea is worth it. This is why I encourage my clients to be bold in design decisions. Read more>>

James Kelleher

The biggest risk I ever took was stepping out of my therapy office and onto national TV. For 20 years, I was used to private, confidential work with clients. Then suddenly, I was on 90 Day Fiancé with cameras and millions of people watching. It was terrifying. Read more>>

Maria Falbo

A fundamental, maybe the fundamental, ingredient of creativity is risktaking. I’m not talking about doing anything existentially threatening, but to be creative, I advocate becoming comfortable with calculated risk-not only in the creation of your artwork, but in the business of art as well. Read more>>

Katelyn Perry

When I first stepped into real estate in 2022, my life felt like a loop I couldn’t escape. I had just lost my grandmother, whom I’d cared for during her battle with brain cancer, and I was unsure where to turn next. Read more>>

Olivia Jaramillo

As a full time college student and part time employee I find myself not having a lot of free time. I was always under the impression that I needed to get my degree and then immediately have a stable and well paying job after college. Truth is nothing that is posted in the job market ever sparked my interest. Read more>>

Daniel Patton

Worked at Deloitte Digital Studio for 4 years, left in 2018 to move to Argentina and start what is today Rothbright. Deloitte was a fantastic learning environment, but after 4 years, I had to make a decision about whether to build a corporate career or to risk it all and build a company on my terms. Read more>>

Kayla Lamb

When I think about risk, two things come to mind: the moment I decided to start my own business with zero clue how to actually run a business, and the moment I signed papers on the biggest investment of my life — my little Farmette here in Des Moines. For years, I ran The Garden Groomer out of the basement of my 600 sq. ft. Read more>>

Jeremy Gray

One of the biggest risks I’ve taken was buying my late grandfather’s land in Opelika for $13,000 and deciding to turn it into The Curtis House. At the time, I had no blueprint, no major funding, and no guarantee anyone would support the vision. But I saw the potential to create a community hub for youth, seniors, and families. Read more>>

Kayla Lawson

The biggest risk I’ve ever taken was stepping into the world of offering psychic readings. At the time, it felt like a leap into the unknown — not because I doubted my abilities, but because I feared how others, especially my family and friends, would perceive me. Read more>>

Shay Walters

My husband and I are both in long-term recovery from drug and alcohol addictions. Once we had overcome our own demons, we were determined to help others. We started working in the addiction treatment field, providing outreach for treatment facilities. It’s a hard job, it’s tiring, it takes a toll on your heart. Read more>>

Valentina Berti

Moving to Los Angeles in 2022 was one of the biggest and most life-changing risks I’ve ever taken. Until then, I had always lived close to Milan, Italy, where I grew up. I had never lived alone in another country, thousands of miles from home. Read more>>

Fredrick Peters

When I finished my PhD in Exercise Physiology, I was sitting on what felt like a mountain of student loan debt. Conventional wisdom said I should play it safe, get a stable job, tighten the belt, and slowly chip away at the loans. But deep down, I knew I wanted to create something of my own. Read more>>

Sharon Krasny

A valuable risk I took was to say no. I said no to someone else’s demands on my time and said yes to taking my writing seriously. As a result, i finished not just one book, but three. In order to get the ending right for the second novel, I took another risk. Read more>>

Lizzy Moffett

Leaving teaching was the biggest risk I’ve ever taken, and honestly, the hardest part wasn’t financial. It was identity. My whole sense of self was wrapped up in being a teacher. I worried people would see me as selfish for stepping away from the classroom, as if serving children was the only way I could make an impact. Read more>>

Sam Widerschein

One of the most rewarding aspects of teaching Tai-Chi/QiGong is getting to experience when a student makes an emotional ‘breakthrough.’ One of the many places that I teach QiGong is at a transitional living substance use program. At this particular time, we had an older patient who was a career Navy veteran. Read more>>

Kierra Bush

At 23, I found out I was pregnant and decided to take the biggest leap of my life. I put everything on hold financially to pursue cosmetology school because I had a dream and a plan — and I was determined to finish, no matter what. Read more>>

Katie Sautter

Life is rarely linear. That motto embodies my story. On paper, I’m Dr. Sautter: I hold a Ph.D. in Material Science and Engineering, focused on quantum and electronic materials. I once had what many would call The Dream Job: a six-figure engineering role with benefits, a 401k, and stability. But inside, I felt restless, confined. Read more>>

Amber Wallace

I’d consider my business, Flamingo House, as one big risk to be honest. Starting this was one of the scariest things I’ve ever done– and I’ve done some wild stuff. Ever since I was in high school I knew I wanted to have a career in a creative field. Something outside of the normal. Read more>>

Denis Gapone

I used to work on big TV production as a videographer and filmed TV shows like Biggest losers, Bachelor, X-factor, etc. It was a dream job to be part of these projects and do what you love but in some time I felt limitation and felling that I’m ready for something more. Read more>>

Emma Johnson

I’ve been a Surgical Technologist for the past 13 years. On a daily, I would spend 10 hours being alongside a physician taking care of patients on the surgical side. In my spare time I’ve always been blessed with the skill to create art through hair. It’s been a passion of mine and it always has brought me joy. Read more>>

Max Smoot

I’m used to taking risks others refuse to take. I think the more money you have the more you’re afraid of taking risks. Like doing whatever you want instead of adhering to a system of economic fear and violence. I have had a hard time with publicity and marketing as a dissident in my very right wing town of Roseburg Oregon. Read more>>

Genesy Ferguson

One of the biggest risks I’ve taken was stepping into real estate full-time when everything around me told me to play it safe. At the time, I had a steady path laid out something that promised stability but not fulfillment. On paper it would have made more sense to cling to security. But I knew if I didn’t bet on myself, I’d regret it. Read more>>

Adellia Metz

The biggest risk I have ever taken was starting my own insurance business. For most of my career, I worked for others and relied on the stability of a guaranteed paycheck. Read more>>

Amy Bonaduce-Gardner

It was a deep dive into the nervous system, fascia, movement, and the kind of biomechanics that makes your nervous system whisper, “Thank you.” But in 2009, the studio needed to change locations due to facility issues, and eventually the brick-and-mortar closed its doors. Read more>>

Susannah Horwitz

That pattern continued. In 11th grade, after having attended a public creative and performing arts school for 6 years, I finally found my voice, taking creative and social risks every day–such as joining competitive choir ensembles, volunteering to audition for solos, and making new friends with students whom I had once considered “too cool” for me. Read more>>

Nakisha Harris

That decision not only allowed me to provide luxury in-salon services, but also positioned me to become a national educator and trainer with Farouk Systems (CHI). In that role, I’ve had the privilege of training and mentoring hundreds of stylists across the country through brands such as JCPenney, Fantastic Sams, and Sally Beauty. Read more>>