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.

Matthew Wassong

When I think about risk, I think about the fall of 2020—a time when everything we knew about the world seemed to be unraveling. We had just graduated from Chapman University’s film school, jobless, isolated, and unsure of what the future held. But instead of sitting in that uncertainty, we made a decision that, in retrospect, was both completely reckless and incredibly rewarding: we decided to make a movie. Read more>>

Alanna Beebe

I cannot remember a time in my adult life when I wasn’t taking a risk, both big and small. When I graduated college I moved to Peru only knowing one person but ready for any adventure that came my way. That led me to move to the United Kingdom where I worked as a nanny. Then, I took a volunteer job that paid a very small stipend back in the United States. It was risky because I had to figure out how to live on $800 a month, yet work in a big city. This risk launched my career. I was offered a job at the local public health department and immediately found my passion in equity and social justice. Fast forward to almost 10 years ago, when I decided to risk it all again but starting my own company. Read more>> 

Dr. Felice Chan

 

From as young as six years old, I knew I wanted to be a doctor. Growing up in Hong Kong, I was immersed in a world where Western medicine was the norm. The closest clinic to my home was a Western one, and whenever I had the flu, I would visit and leave with a prescription for pharmaceuticals. It felt natural to follow this path. I pursued neuroscience and pre-med in college, dedicated two years post-graduation to conducting clinical research in the allergy and immunology department of a hospital, and prepared myself for medical school—I even took the MCAT. Everything was lined up perfectly for a traditional career in Western medicine. Read more>> 

Valichii

Three years ago, I made the decision to change the course of my life and my career by moving all the way to Los Angeles, California. Born and raised in Lima, Peru, the idea of moving away from home to pursue music felt like a distant, somewhat unattainable, dream; I always knew music and singing was going to end up being a part of my life, I just refused for so long to see how it was meant to be my path, out of fear of pursuing what seemed to be an impossible daydream. Read more>> 

Jessica Moss

Throughout a career rooted in community-centered artistic practice, one persistent caution has remained clear: trust no one. “Don’t invest here,” critics have said, “you won’t see a return.” This skepticism reached its peak with The Garfield PGH Project—a long-term solution to the short-term housing needs of Black visiting artists in Pittsburgh’s Hill District. Questions arose about the decision to beautify a space in a community already suffering from disinvestment and displacement. Read more>>

Erodney Davis

In 2007, I made a bold decision to quit my fast-track career in fashion advertising to pursue entrepreneurship. This was long before it became trendy, and most people thought I was crazy to leave a comfortable corporate job. I had meticulously saved a year’s worth of living expenses and planned to open a men’s lifestyle store in Brooklyn. However, as I delved into the realities of the market – the looming recession, the rise of e-commerce, and the impending housing market crash – I realized the risks were too high. Read more>>

Troy-jeffrey Allen

I’ve hit a point in my creative trek where I really appreciate the delusion that comes with choosing to be a maker of things. That delusion allows you to not think about the risk or potential embarrassment that can come from it. I dream up stuff for a living and convince others — co-creators or the audience — to take the ride with me. From the outside looking in, that is either risky or a disorder. But it’s that level of willingness to “show your ass” that separates creative people from everyone else. We’re all engineered socially not to be exposed in public, so inviting strangers into your head- whether it’s your painting, novel, film, or whatever- is bold! And it starts when you decide that you have something worth sharing. Read more>>

Erika Dely

When I started my business I walked away from the career path I had planned for. Photography gave me more flexibility to have a bit more freedom and I had a partner to fall back on if it failed. I was engaged to be married and the trajectory of my life was to get married and to have kids. Having a photography business could be flexible while raising them, it was the perfect plan. I could take weddings and jobs more during some seasons and then less during others based on what my family needed. The business was doing well and it seemed as if everything was coming together to work out just so. Read more>> 

Leah Musacchio

Seven years ago, it was a night like any other—except for me, it wasn’t. That night, I hit “submit” on my application to start my master’s program. So many possibilities swirled around in my head: Would I get accepted? My undergraduate grades weren’t the best, so who knew if I even stood a chance? School had always been a challenge for me. Was this even feasible? Read more>> 

Amy Cheryl

I became involved in fitness when I was 15 years old in the 1980’s after losing over 80 pounds and developed a deep passion for wanting to help others fastback their progress and not go through the hardships I did to achieve my goal. I always had a core soul desire in the helping others come home to their joy and empowerment. Fast forward decades and in 2008., when the recession hit, my fitness career took a huge nosedive. I had serval high profile clients as I was living in LA (after moving there from New York to “pursue the dream”) at the time and many of them cut corners where they could. I was at a crossroads as I was feeling my body getting tired and my passion from fitness was weaning, plus I took a huge hit where overnight I couldn’t pay my rent. It was a scary time. Read more>> 

Miguel Portugal

To me, the word “risk” often carries a negative connotation because it’s associated with the possibility of failure or bad outcomes. And while that’s true in a literal sense, I believe risks come in levels, and we don’t always recognize the ones we take every day. Every breath, every decision, every moment involves some level of risk. So, what holds people back from taking bigger risks? Fear. Read more>>

Subduer Dre

At a point in a time in my life I had to create a different way to provide for my family and I. It was take the risk or brake the promises I already made. I got tired of the feeling of braking people hearts that loved me the most so I bet on myself and took the risk and my old self went ghost. Becoming an agent of change along with finding my purpose in life was the greatest risk I ever took. Read more>>

Glenn Williams

When I think of taking a risk I can’t help but think of getting into Professional Wrestling. First of let’s start with the biggest glaring hurdle I am now 36. When I started training I was 33. See most people who peruse wrestling are fresh out of highschool or in their early 20s. Now let’s add in the fact that I was also 270lbs and incredibly out of shape. Read more>>

Adelaide Graye

One of the biggest risks I’ve ever taken was trusting a complete stranger during one of the darkest times in my life. I was battling severe depression, compounded by long COVID symptoms and the physical and emotional turmoil of a challenging menopause. I felt like I was dying—or perhaps more accurately, I wanted to die. My depression was deemed “untreatable,” and no one seemed to have answers for my long COVID symptoms. Read more>>

Louise Harris

The first big leap I took was in my twenties when I had the chance to transfer from my PR agency’s London office to their Singapore branch. It felt like diving into the unknown—moving to a new country without knowing a soul, not having a clue what to expect, and with zero guarantees. It was scary! But instead of letting fear paralyze me, I just went for it. I told myself, “What’s the worst that could happen? If it doesn’t work out, I can always go home.” And with that, I got on the plane for a 12-hour journey that changed my life. Read more>>

Sarah Grace

Like many of us 2019 found me living life as usual. Enter 2020. The year I like to call “Perfect vision”. Things simultaneously went out of focus and seemingly chaotic, but brought into focus what was real. Life long friendships changed in seconds. Families torn apart. Churches closed. Business closed. Faces mandated to be covered. Freedoms halted. Fear everywhere you looked. We each were reduced to who we really were. Shrink back and comply, or stand. Read more>>

Lex Thecreator

Hi, my name is Lexthecreator! I’m a 24-year-old mompreneur on the climb to creating generational wealth through digital products and online businesses, all from the comfort of my home. I started my skincare business in 2021, taking multiple risks because I wanted more out of life than just the American Dream. Read more>>

Farzad Akbarpour

The biggest risk I’ve ever taken was purchasing my current business. It was located in a spot that seemed completely obsolete at the time—surrounded by people, a strong community, and thousands of cars passing by every day. What I initially thought would be a quick flip and an easy way up quickly turned into a risky investment. When I first saw the location, I thought it was a golden opportunity. But, boy, was I wrong. Life hit me like a freight train, and nine months later, here we are—thriving. Read more>>

Meggie ‘fig’ Copeland

When attending Sass N Strut dance classes in 2019, I could’ve never imagined I’d be opening up our very own studio space with creator, Serese Brown, just three years later. Having spent my time working professionally in dance clubs around Austin since 2018, and performing burlesque professionally with Brown Burlesque since 2019, I was looking to deepen my relationship with dance. In 2021 I created my own class and teaching style in a class called Slink & Strength- a two hour weekly deep dive into mobility, strength training, and sensual dance movement. I wanted anyone and everyone to feel comfortable in their body, but not only that, I wanted them to know how strong sexy is— and how accessible that can be! I brought Slink & Strength to Sass N Strut as an instructor that same year. Read more>>

Victoria Kravchenko

I immigrated from Russia with my family when I was 13 years old. My parents brought us (myself and my brother) to the land of opportunities and always wished for better future than what they had back in Russia. I grew up in Brooklyn, NY-got my high school diploma and my undergraduate degree in Psychology and pre-medical program in NY. My parents never babied us too much and the biggest lesson we had to learn in life is how to be independent and adopt to any situation in life. I had to learn how to navigate through high school, undergraduate and graduate school with minimum involvement from my parents. I immigrated from Russia with my family when I was 13 years old. My parents brought us (myself and my brother) to the land of opportunities and always wished for better future than what they had back in Russia. I grew up in Brooklyn, NY-got my high school diploma and my undergraduate degree in Psychology and pre-medical program in NY. My parents never babied us too much and the biggest lesson we had to learn in life is how to be independent and adopt to any situation in life. I had to learn how to navigate through high school, undergraduate and graduate school with minimum involvement from my parents. Read more>>

Pollyanna Blanco

Our comfort zones can get quite cozy. While a part of us dreams of moving forward, another part of us drags its heels. The resistance we can feel to change can be so great that we end up settling for hanging out in our familiar discomfort zone. This push-pull dance was something I contended with when I first had the inkling that there was a book inside of me. Read more>>

Cassandra Vandall

The biggest risk i have ever taken was packing up and moving over 1000 miles away from Ohio, the place i had called home for 20+ years to move down to Texas to start my rescue and save animals as much as i could. I moved down here not knowing anyone at all so it was a huge change going from having friends and family close to just having myself and the animals that came down with me. I flew down to interview at a couple places before i decided on a date to move down and once the job came along i finally made a date to move March 2019. Honestly it has been the biggest struggle but in the end its worth it to me to be able to see the dogs i have saved and found furever homes for and them living there best lives with their families and they may not have gotten this chance had i not taken a huge risk and uprooted my life to move! Read more>>

Rae Cerulean

Honestly, just deciding to be in a creative field felt like a huge risk to me. When I graduated high school I didn’t think it was possible for me to be a full time creative. Music and art were a huge part of my life from a young age but I was discouraged to pursue this professionally. So, I went to college to major in Nutritional Biochemistry with the goal of becoming a doctor and pursuing creativity in my free time. Three years into my degree, I didn’t have time to create or even be in the school orchestra due to my busy class schedule. I was miserable. Read more>>

Madison Crawford

When asked about taking a big risk in my acting career, I immediately think of my decision to move from Boston, MA, to Atlanta, GA. I grew up in New England and had never really left. I absolutely loved it there! Boston has such a special place in my heart, from the tight-knit film community to the amazing indie projects I was part of all helped me grow so much as an actor. It’s where I found my love for acting. But as much as I loved it ( and still do!) I started feeling like something was pulling me out, like it was time for a new opportunity. I knew I needed to step out of my comfort zone and see what else was out there. Read more>>

Alexandra Peek

On an evening in September of 2021, I received my second employment rejection letter for the week. Both jobs were in law firms located in NYC. I had been applying from my home-state in Texas, and I was looking to move to NY. I wanted to be smart about it and go with a security blanket, so I applied to many positions in the field that I knew (law) in hopes of snagging a job before moving out there. However, the fact that I still hadn’t relocated was turning off employers and recruiters. After receiving yet another rejection, I was venting to my cousin about it. As she responded, I took out my phone and looked up flights from El Paso, Texas to NYC. I saw a one way for $179, and before I knew it, I had purchased it. About 2 weeks later, I had stuffed as much as I could into 3 suitcases and a backpack and moved to NYC without a job. About 2 years later I was making a six-figure salary, the most my parents or I have ever made. Read more>>

Chang Wan Alex Jin

In 2016, I decided to study abroad in the U.S. while living in Korea, with the dream and plan to stay in New York after graduation and keep my career as an artist. However, moving to a foreign country with no connections was not an easy task, and it was a costly plan. Many international students in the U.S. pay enormous tuition fees but end up returning to their home countries after finishing their studies without being able to settle in the U.S. In order for me to stay in New York after graduation and continue my artistic career, I needed to have my talents as an artist recognized by the world. Establishing myself as an artist and making a living in the U.S. market seemed like a vague and difficult task. However, despite the significant costs, I thought that even if I failed to settle in New York after graduation, I wouldn’t have much to lose. I believed that the experience of studying abroad would make me a better version of myself, and so I made the decision to move to the U.S. in 2017.
Through hard work and dedication to my studies, I was able to develop my own body of work. After graduation, I received a scouting offer from an art studio in New York (Rko Studio) and began working on my art. With the studio’s sponsorship, I gained recognition for my talents as an artist from the immigration office and was granted a stay permit. Now, I am living my dream and continuing my artistic endeavors in New York.
What I’ve realized recently is that life is unpredictable and doesn’t always go as planned. But sometimes, when you dedicate yourself fully to the task at hand and give your best effort, unexpected rewards come your way. Read more>>

Lauren Krailo

My entire life has been about taking risks. I’ve never been one that was able to conform with authority. Growing up in a military home with traditional views, I wanted to be anything but fit into that basket. From an early age, I knew that I wanted to be different. I didn’t want to “traditional”. I wanted to be a risk taker. So naturally, I had to do all the things that would set me apart. Read more>>

Aj (aj The Vj) Johnson

One of my earliest risks involved a huge leap of faith into the unknown with a moment of serendipity that still leaves me feeling thrilled to be VJ to this day. I was invited to do projections at a small micro-Burning Man festival (Deep Playa) in rural upstate New York, I had no idea what I would be projecting on or what the set-up would look like. Read more>>

Laicy Wester

One of the most profound risks I’ve taken was embracing astrology as a tool to explore the realms of sex, intimacy, and human connection in a way that was unapologetically bold and often considered taboo. I decided to launch a podcast called Astromantics, where I dive into intimate, often NSFW, conversations with a wide spectrum of people—LGBTQ+ folks, dominatrixes, s*x workers, and anyone with unique insights into the cosmic dimensions of our desires. Read more>>

Ksenia Khelman

The biggest risk I’ve ever taken was when I fell in love and decided to leave my regular life behind to move to Chile to meet the guy. At the time, I didn’t speak Spanish, and I had no idea how I was going to make a living. All I knew was that my life felt too normal—like it was missing something—and I craved a change. Read more>>

Billy Murray

I have always been a risk taker, and have failed at multiple businesses. Quitting a well-paying, comfortable job to become a professional photographer at 47 years old is insanity. I took a big risk when I spent all my savings on airplane tickets and equipment to prove to myself, my wife, and my son that I could be one of the world’s best portrait photographers. I was determined to succeed. In the last two years, I have created a body of work that speaks for itself. This work has opened incredible opportunities for me, which has brought me closer to achieving my vision. Best risk I have ever taken. Read more>>

Kailah Sullivan

Getting into tattooing is taking a risk in itself. I feel that anyone who decides to take on the journey of becoming a tattoo artist needs to be aware that there is no guarantee that your expectations will be met. Pursuing to learn this craft is serious. Turning tattooing into a career is not the typical societal career journey where you go to school, perhaps college, and then enter into the work field. It also doesn’t come with benefits that a lot of other jobs provide. There are no healthcare or dental care plans, retirement accounts, PTO, etc in this career. You are entirely self sufficient and your success depends completely on you. Myself and thousands of others choose to give up the stability that comes with more traditional jobs in pursuit of our passion for art and the hope to enrich our client’s lives with it. I consider tattooing to be one of the most fulfilling jobs in the world. It’s a privilege to have as a career, but it does require taking risks and making sacrifices to bring into being. That said, it’s been one of the best decisions I’ve ever made.

Christopher Mccormick

One of the biggest risks I’ve ever taken was moving to LA and it paid off in so many greats ways but it also had its drawbacks. I moved to LA in 2018 with no promise of employment and very little money. I had recently come out, struggling with immense depression and really had no concrete plan as to what I wanted to do. I graduated from Pratt Institute with my Bachelors Degree in Architecture & had been working in the field in NYC for about 5 years. I knew I had dreams to chase but how I was getting there was a huge leap of faith. In 2017, I found solace and comfort in creating again and jumped back into my love for painting and portraiture. It saved my life in so many ways and continues to fuel me. Fast forward back to LA, I landed a job with a boutique architecture firm and started living my dream. One of the biggest risks I’ve ever taken was moving to LA and it paid off in so many greats ways but it also had its drawbacks. I moved to LA in 2018 with no promise of employment and very little money. I had recently come out, struggling with immense depression and really had no concrete plan as to what I wanted to do. I graduated from Pratt Institute with my Bachelors Degree in Architecture & had been working in the field in NYC for about 5 years. I knew I had dreams to chase but how I was getting there was a huge leap of faith. In 2017, I found solace and comfort in creating again and jumped back into my love for painting and portraiture. It saved my life in so many ways and continues to fuel me. Fast forward back to LA, I landed a job with a boutique architecture firm and started living my dream. Read more>>

Anna Ratala

The year was 2019. I’d never had an American dream. As a girl from Finland, I never looked at America as the land of opportunities. Opportunities are everywhere! Besides, I’d built a comfortable life in the heart of Asia, in Singapore, where I was running a big tech startup event. Who needs America anyway? Read more>>

Rebecca Von Boeck

I am right smack in the middle of the biggest risk I’ve ever taken, punctuated with many small risks along the way. I left a job a few years ago, toward the end of the pandemic. It had been an emotionally toxic place to work and I decided that I would be very intentional about what to do next. As I began to search for new employment, I stumbled upon a job at a Functional Medicine office as a health coach. As someone who has spent the last 20 years researching and implementing a healthy lifestyle, this sounded like the perfect job for me, so I applied. The job description didn’t require any particular credentials, but technically I wasn’t qualified. They actually took the time to interview me based on the intro video I sent with my application! They did not hire me, but that’s when I knew what I wanted to do. So I went back to school and got my health coaching certificate, realizing that this is the path that I am called to. During my training, though, being a free spirit, I realized I wanted to try to venture out on my own so I founded DirtMama Wellness Coaching. Read more>>

Fatima Iqbal

One of the biggest risks I’ve ever taken was starting my own medical practice. After years of working in healthcare, I saw firsthand how large practices often left patients feeling like just another number. Many struggled with preventable issues like weight gain, stress-related imbalances, and hormonal health challenges, particularly women navigating menopause, perimenopause, and PCOS. These patients needed more time, attention, and a personalized approach—something traditional models rarely provided. Read more>>

Jeff Legg

Nestled in the mountains of eastern San Diego County, Mt Laguna is the highest point within the county at an elevation of over 6000 ft. With less than 100 full-time residents, the hamlet sits on the Pacific Crest Trail (PCT) and boasts scenic views of the Cleveland National Forest. While very few people live in Mt Laguna, almost 6 million visit annually for various activities throughout the year, enjoying everything from hiking, hunting, biking, and snow play. Read more>>

Jill Carey

I spent 27 years in a previous career path that I never thought I would leave. Then in 2024 I decided to start something. At first I thought if it was going to be a retail store but very quickly, like within days I knew it needed to be a brand. From the first time the idea came into my head for the next few weeks I had a notebook with me at all times; I even slept with it under my pillow. And every idea that popped into my head was written down. Read more>>

Lori Grechika

I have been a Real Estate Advisor since 2004 in CT and although I love my career choice because I’m a people person I never quite felt I was working to my full potential while living in CT. I battled a serious alcohol addiction for many years which ultimately affected my career. I attempted other career choices and had some rather large hiccups along the way but managed to keep active with my career and horses. When my, now adult children, Michael & Dakota graduated and began living their own lives I made the decision that I wanted a fresh start in SWFL. We didn’t know anyone in the area, and I had no contacts to give me insight into what living there was like I only knew I needed a fresh start, fresh air, sunshine and warm weather! Read more>>

Sasha Jones

I think the biggest risk i took was– choosing my hard. in regards to being 300lbs and overweight with diabetes. & realizing im jus going to have to invest in my illness or invest in my health & taking that risk of choosing the healthier lifestyle not knowing where to go, what to do or even how to workout and where to start Read more>>

Julie Robinson

Risk is felt individually based on the specific context of each situation. For example, it can seem risky to get out of bed in the morning on some days. It was a risk when I decided to start my first business when I was 31 with a small child, and it was a risk to go back to school in my 40s, which led to the creation of my second business, and it was a risk to stick with the business during the pandemic. All of those risks led to me being where I am now, which is further down the road, and continuing to be creative. Read more>>

Mikki Ulaszewski

Two and a half years ago I picked up my whole life with my family and moved from Rochester, NY, to Seattle, WA to pursue being a full time artist. In December of 2021 I was recovering from an illness in the midst of the COVID-19 Pandemic and working full-time as a graphic designer for a school district. I was so stressed and burnt out that I was having several panic attacks a day. In one swift moment I told my partner we couldn’t resign our lease, we needed to move, I needed to move. I couldn’t spend the rest of my life doing art for others, the same art, the same posters year over year. By that summer we had uprooted our whole life in NY State and were moving to Seattle, WA to start a new life. Read more>>

Luna Nguyen

Growing up as a young adolescent, it often feels like everyone is constantly asking, “What do you want to be when you grow up?” Family members, peers, teachers—everyone seems to expect you to have a clear answer, as if life’s path is supposed to be straightforward. But when you are at that age, everything feels uncertain, and the truth is, there’s no simple answer. You are still figuring out who you are, what you like, and what you want to do with your life. Read more>>

Udayan Joshi

I attended Pitti Uomo, Florence Italy in January of 2024. Got really inspired by the world of fashion and the styles which were on display. I was working on a small collection and got inspired to launch my collection. In the process, quitting my software services job and working full time on the JoCo brand. Read more>>

Joy Morales

My creative journey started about 4 or 5 years ago by taking the huge risk of dropping out of college to pursue a career in tattooing. I was 22, living alone, and craving a different lifestyle than your typical college student. I started a formal tattoo apprenticeship in late 2021, and became fully licensed to tattoo in 2022. I started my own brand/business called InkdCreativeStudio in the summer of 2023, with the goal to change my own artistic paradigm, with the hopes of encouraging self expression and individuality through the medium of tattoos. Read more>>

Kikue Misite

The biggest risk I’ve ever taken was letting go of getting a paycheck. Ever since my first job at 16 years old cashiering at Rubio’s, I cared so much about giving my all in exchange for that beautiful, exhilarating paycheck. I was definitely addicted. Fastforward through years and years of yearning for it every two weeks – from being a cashier, to working a desk job, to being a yoga instructor, to night shift in the hospital as a Registered Nurse. Buying whatever I wanted when it came: vacations, takeout, clothes. It was so stable and consistent. I broke my addiction at 35 years old…that’s a long time to be addicted to something, right? Read more>>

Dawn Pilpel

The biggest risk I’ve ever taken was starting my own business. It was a decision that completely altered the trajectory of my life, and one that I wouldn’t trade for anything. Let me take you back to the beginning so you can understand the why, the how, and the lessons that came from it. Read more>>