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.

Monte Reyment

One of the biggest risks I’ve ever taken was starting Take Action Realty Group just 1.5 years ago. I wasn’t interested in doing real estate the traditional way—I wanted to break the mold and create a company built entirely around relationships, gratitude, and community. I knew the industry could feel transactional at times, and I wanted to prove that leading with purpose and putting people first could still be a winning formula. Read more>>

Kevin Liao

I’ve pursued various aspirations throughout my life, from excelling as a clarinetist in middle school to dreaming of becoming a polyglot. Each ambition taught me the value of diligence and discipline. However, my most transformative journey began when I decided to study computer science in college and later took the leap to build my professional brand. Read more>>

Deborah Fryer

Tell us the story of a risk you’ve taken – it could be a big, life changing risk or a small risk. Either way, paint the picture for us, tell us the backstory and all the relevant details so we can fully understand the context and circumstances around when and why you took the risk and tell us how it turned out. Read more>>

Kaylee Kim

In a way, choosing to pursue art was one of the biggest risks I’ve taken. Medicine and business runs in my family and, for a while, I tried convincing myself STEM was right for me. I grew up in predominately Asian and suburban cities where it was easy to blend in and I ignored my hobbies and interests that came from alternative or “nerdy” scenes. I joined a technology based track in high school as well as the robotic’s team (where, granted, I worked on publicity rather than engineering). At some point in high school, I was drawing while waiting for classes to start and, as cliche as it sounds, I had an epiphany where I realized I could do this for the rest of my life. Read more>>

Ashley Fortune

The journey to Letter your Life Designs began around June of 2013 (after being gifted a crafting machine December of 2012). I can remember sitting in the room that held my six foot table, washer and dryer while I came up with a name. I have always been one who enjoyed creating and more importantly gifting home made crafts to loved ones. This all began after having many friends suggest I begin created and selling my creations. My number one seller at the time was an 11×14 floating frame created with vinyl and all of a baby’s stats (weddings were close behind) but my oh my how it has transformed over the years. But back to the name as I want to share how I got here. Read more>>

Courtney Eidson

The biggest risk I have taken was opening Trailhead Community Farm School, a nonprofit therapeutic academic day program. As I am not a teacher or school administrator, the prospect of building an educational program was daunting. However, my background as a clinical social worker, with experience in various settings from residential placements to private practice, made me aware of the significant need for a therapeutic academic day program for neurodiverse students, particularly middle and high school students with Autism and/or ADHD, as well as the lack of support for their families. Read more>>

Charles Perlie

So the back story of Dj Chuck and how it started I always been cooking my whole life and still do it now from today but I always listened to music and love the different genres since I was a kid so as I got older I felt like I wanted to take interest of making my own music but not only that wanted to do what djs did to amuse and wow the crowd because it was the transitions they would do so as I got to practice it I seen I could do what other djs do and still learning my craft and getting better so this how my story of Dj Chuck started. Read more>>

Amanda Howell

The biggest risk I have ever taken is opening the Amanda Howell Agency. I separated from my previous company on February 19, 2024 and had this idea for many years to go into business for myself using my personality, ability to build strong connections, love of networking and community to build a business. I joked for years, if I could open a company of my own, become self employed, attend networking events – connect others and serve non profits for a living, I would do it. Here I am 10 years later from that thought, running my own company that does just that. I started this with an idea, after a devastating job loss and did it all with very little money, no income to fall on, a hope, a dream, lots of faith and prayer. Read more>>

Marz (mariano) Garcia Jr.

Moving to NYC is definitely on my list of big risks I’ve taken so far in my life. I moved to NYC for my first Art Director job in advertising. The uncertainty of moving to an expensive city filled with talented people made me question my abilities. I kept thinking about what could go wrong, like whether I would run out of money, and at the same time, asking if I was talented. But I overcame these doubts by focusing on what could go right and reminding myself of my talents. Shifting to a positive mindset helped me take the leap. Read more>>

If I look back at my life now I can tell that taking risks was one of the most rewarding things I could do on the path of searching and uncovering my true self. In a way I view and sense my life in cycles some old cycles were gracefully and organically transformed into new ones but some turned into comfort zones and stagnations and needed to be broken in order to grow and expand and that’s exactly when taking risks was necessary. The risk of leaving my hometown into unknown to follow the dream of becoming a dancer was one of the first serious risks I took. I come from a very small town on the far east of Russia where Siberian forest meets Pacific Ocean and Asia. Read more>>

Alejandro Silva

El fitness me cambió la vida, y decidí dedicar mi vida a estudiarlo, aplicarlo y guiar a otras personas en su proceso. Asesorando personas notaba que muchas de ellas se auto saboteaban en sus procesos. Los miedos, creencias e inseguridades les impedían avanzar, o a veces incluso les dañaban. El notar esos patrones me despertó una inquietud “¿qué podía hacer yo para ayudarles en ese aspecto?”. Read more>>

Roussie Jean Honore

On January 17, 2022, I stepped foot in the United States for the first time as an immigrant with only a basic understanding of English. As a mother, I wanted to find a job that wouldn’t take too much of my time because being present for my children was my top priority. Read more>>

Lou Simón

I gave up a thriving legal practice to pursue a creative passion. Growing up, I had always wanted to be a writer, but as I was graduating college, I was hesitant to pursue the life of a creative and all the uncertainties that would bring. Therefore, I decided to go to law school. I convinced myself that I would have a legal career as a way to make a living while I continued to pursue my writing. However, the realities of private practice were even more demanding than I had anticipated. I had my own office, which added additional responsibilities and stress. Therefore, I stopped writing altogether. Read more>>

Andrew Mcfarlane

The biggest risk I took in my career as a music producer came when I decided to fully transition from being primarily a guitarist and bassist into the role of a producer. I had been playing and writing in bands for years, but as soon as I produced and wrote my first project in college, my capstone project, I knew that this was the creative lane in the music industry I wanted to pursue. At the time, it felt like I was leaving behind a world I knew well and diving into a space where I was less experienced and felt pressure from myself to learn the craft fast. Even though I still spend plenty of time as a hired gun as a live guitarist and bassist, this was a big change for me. Read more>>

Elizabeth Mintun

I have always been a very private person who preferred to be quietly doing my own thing. A psychotherapy practice suited me perfectly in this regard, because I could be behind the closed door, offering my expertise to those who chose to come in, and otherwise not have a public face. Read more>>

Andrew Crabtree

The life of a person whole wants to make it in any sort of professional sport must be willing to take risks. My journey so far has been no different. What’s up everyone? I’m Andrew Crabtree, an up-and-coming street trials and mountain bike rider. I have many stories of risks I’ve taken but, one recent one stands out. In filming my most recent riding video, “Drew Crabtree’s DAYDREAM”, in this particular clip I wanted to hit a soccer ball with my bike to block a shot on goal. This required my bike to spin around my forks while I stand on my front tire, known as a footjam tailwhip. By swinging the frame around I would block the ball from going in the goal. Read more>>

Christian Harrison

Coming out of college in 2016, I was the 8th fastest 800m runner in the NCAA. While that was a feat I was proud of, it wasn’t quite fast enough to get offered a contract to run professionally. So I took a job offer that moved me to Boston. While in Boston I did get a contract with the Boston Athletic Association, but it did not come with a salary, only performance bonuses and Adidas apparel. Training on the side while working full-time was difficult, but winter of 2018 it was finally starting to pay off. I had run the 7th fastest time in the U.S. and 18th fastest time in the world (indoors). It was looking like I was going to have a great outdoor season, however I would suffer a season-ending injury just one month later. Read more>>

Paola Marquez-smith

Deciding to leave my home country and pursue music was the biggest risk I’ve ever taken. Back home, I had a comfortable life surrounded by my friends, family, and a familiar environment that meant the world to me. I also had a sense of stability, knowing what to expect each day and feeling secure in my community. However, something inside me yearned for more—a desire to follow my passion for music and see where it could take me. Read more>>

Aida Barroso

The biggest risk I’ve taken in my photography career was deciding to walk away from a secure, traditional job to pursue my passion for storytelling through photography full-time. At the time, I had a stable career, a consistent paycheck, and all the comforts that come with job security. But deep down, I felt unfulfilled and couldn’t shake the feeling that I was meant for something more—something creative and meaningful. Read more>>

Leah Fellers

In my practice, I challenge what women are being told every day about their bodies and how to birth their babies. Is there a giant liability to liberating women to face the fears looming over them by the medical society? Yes, it is an enormous risk, and yet, I do this work by helping women reignite their intuition and return to the wise women within. Read more>>

Emily Young

The photography realm is very saturated. Not to mention the crazy amount of new technology and AI software that makes it seem “easy” to be a professional photographer. I have been in love with the art of photography since I was in middle school. I began to take my hobby more seriously and photograph families and events around 2016 when I received my first professional camera as a gift. Finally, in 2024 I took a risk, not knowing if I would fail or succeed, and started by photography business in July. It was THE BEST decesion that I have ever made. I have learned so much as a business owner and growing photograper in such a short amount of time. There are so many more things to learn and skills to perfect as I continue on this challenging but beautiful journey. Read more>>

Craig Roberts

After 27 years in Law Enforcement, working in Patrol, Bomb Squad, SWAT, undercover, public relations and 14 years flying police helicopters (with three engine failures and several “precautionary landings”), and having served as a US Marine infantryman in Vietnam, and also spending 30 years active and reserve in the military including my 4 years active duty in the Marines Corps and 26 years in the Army National Guard and Army Reserve. I retired in 2006 as a Lt. Colonel. I then began focusing on a career in writing and investigative journalism. Read more>>

Rex Enriquez

My whole life I’ve been told to work harder than everyone else. This mindset that I was taught since being a little mijo (young boy) has only rewarded me more responsibilities and work throughout my life. I felt that there had to be more than working hard but I never saw it around me. I had never seen anyone live and work for their purpose. I knew since I was an adolescent that I loved helping people. It is my purpose and fulfills my heart. Up until just a few years ago I was good with coaching people through their troubles and helping them achieve their success. It seemed that the only person I never really was good at coaching was myself. Read more>>

Alex Cordova

One important aspect that often goes unrecognized is the various types of risks you can take while building your career. You can never predict where these risks will lead you.

I’d like to share my story to illustrate why taking risks is essential and how they shape your character.

This journey began years ago when I decided that electronic dance music (EDM), particularly Techno, would be a significant part of my life. It became a medium through which people know me, how they interact with me, and a way for me to express my true self. Read more>>

Honey B

Becoming a tattoo artist was one of the biggest risks I’ve taken in my life but not taking that opportunity was even bigger in my mind. I’ve always been fascinated by body art from the time I was kid, seeing tattoos on strangers and even my friends parents. My family was very conservative so no one in my family had tattoos and they had very strong feelings about people getting them. Therefore being a tattooer was out of the question so I just continued focusing on art. I took advanced placement art in high school and I ended up getting a scholarship to go to Ringling. I was scared out of my mind because I just knew they had it wrong, like there’s no way out of the hundred of kids that applied they picked me. Read more>>

Kelly Mateo

When my twins graduated high school & left the house, I experienced “empty nesting” & it was very bad. I felt I had no purpose or knew what to do with myself after that. I fell into a dark depression. I went from raising kids & having to be there for their every need to they don’t need me anymore? What am I going to do with myself? My significant other suggested finding a hobby or something that I like to do & I really had to think? What do I like to do? I had spent so much time just focusing on their needs & wants etc that I lost sight of myself. So I started out making candles. Then I started doing a little research into diy & holisitic remedies. Read more>>

Sm6 Band

For us, the biggest risk we’ve ever taken was following our dream to be artists. Each of us plays multiple instruments and at one point we thought “what if we did this together?” – at the time, years ago, it was just something fun to do that we enjoyed but we weren’t thinking about it as a career. Our oldest siblings, George, was going be a firefighter and Isabel, was busy picking out a college to go to. The conventional lifestyle. I can’t recall the exact moment, but at one point our focus shifted… we wanted to make music as a living. Choosing this as our career made us happy and life is short so we thought “shouldn’t we enjoy how we spend our time on this earth?” Read more>>

Malissa Lee

I wish I could say I took a leap into becoming an indie romance author. But it wasn’t a cute little hop over a hurdle. It was more like strolling across what you thought would be a smooth landscape, only to fall down a rabbit hole and realize it’s a lot more tumultuous than you thought. But, I wouldn’t change any of it. Read more>>

Betty Encinales

Moving to different countries for work has been a bold risk—stepping into the unknown without a network to lean on. But my adaptability and curiosity have been my greatest allies, helping me build connections and thrive wherever I land. It’s the price—and the reward—of having a global mindset and a passion for exploring the world!” Read more>>