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.

Chelsey Kapuscinski

In June of 2017, I graduated from the Dr. Ida Rolf Institute of Structural Integration in Boulder, CO, and hit the ground running with my private practice in NYC. I was in my mid-20s, and like many New Yorkers of that age, I was counting every dollar that I spent and earned. Unable to afford commercial space, I turned my kitchen into my work studio. Read more>>

Omobola Imoisili

When I started my business, I was selling t-shirts and other merchandise centered around a character from a children’s book I wrote, Feyi Fay. I sold a few products but not a lot. It became apparent that to propel my business to the next level, I needed to make a significant change. Read more>>

Carolina Marrelli

I’ve had 2 big, risky career moves in my adult life. Read more>>

Adrienne Getka

In 2018 decided to take a risk and I changed my life completely. I was stuck in a dead end job of 10 years and an unhealthy marriage of 12 years. My creative goals were in my horizon and I wanted to see what I could accomplish if my dedication to painting was 100%. So I quit my job and ended my marriage to pursue life as a full-time artist. Read more>>

Daisy Cuellar

First and foremost, I would like to express my gratitude for this wonderful opportunity. Being featured in this way signifies that I am on the right path, and I am truly humbled. Thank you so much. Read more>>

Julien Elizabeth

Leaping into self-employment and following my heart with my business was a big risk. Before 2013 I was working in Chicago at an advertising agency. It was fast paced with long hours, and a lot of client work. In the beginning I really loved it — for many of the same reasons I love what I do now. After some time though I started to experience burn out and the work just wasn’t fulfilling. When I started practicing yoga regularly (as a way to manage the stress from my job), I knew pretty quickly it was my next career. Read more>>

Abigail Tuano

6 months ago I took a risk and quit my full time job, pack up my car and move cross country from Miami to LA to pursue photography. It was definitely a hard adjustment to leave everything behind and move forward with my life here in LA. Last year in September I heard God speak to me and told me to move to LA to pursue photography. I thought that I wouldn’t be able to move here because of everything I had at home in Miami but with months of applying and networking I found my place here in LA. Read more>>

Amanda Tutschek

The biggest risk is not taking any risk. The worst thing that can happen is fail. Taking risks, as scary as that may be, is the only reason I am where I am today. I remember when I sold one my first paintings. I was working my arse off waiting tables. Crying most nights. Not knowing what to do with my life, but knowing it sure wasn’t that. Read more>>

Darius Winfield

Risking it all, I left my hometown for Chicago after high school. Two of my close friends had already been accepted to Illinois Institute of Art-Chicago. I had been granted a full scholarship to IUPUI where I planned on studying business; although, I had no genuine enthusiasm for the major. As I readjusted to college life, I made frequent visits to my friends in the City and began to fall in love with the energy of the city. Read more>>

Carly Fraizer

Starting a swimwear boutique has been one of if not the biggest risk I’ve taken. I had my bikini line, Steele Swallow Bikini and always wanted to sell my brand in my own shop, so when the opportunity arose, I took it. I have only had my shop for a short while and am constantly learning and pivoting, but one thing is that I love making and selling my bikinis. You have to believe in what you’re doing to keep going, and most importantly take the risk! Read more>>

Cassandra sue Chavez

Crocheting, I have been doing since I was 10, but it was not until a few years ago that I began to share my craft. It all began when I had crochet myself a pair of sunflower earrings, and although I thought nothing of it, something happened. Folks out in public kept stopping me to ask about my teji-aretes, or crochet earrings, and to be honest, at the time, the mere thought of me sharing my artwork made me extremely nervous. But I kept thinking about it- this idea of sharing my craft. Read more>>

Kit Wolfe

I believe that it is always wise to stay open to making changes, changes that have to occur in order to keep your business thriving, One of these changes, for me, is seeing beyond the current population of patients that I provide my services to. I am forever looking for new things to learn and how my services and skills can reach more people who are able to benefit from these services/skills. Read more>>

Diego Lopez

Let’s take it back to the beginning of 2022, Where I had two choices. I could take my savings and have “fun with it” or use it to invest in myself and those around me. As much as I wanted to buy a brand new car, move In a nicer home and go out every night, I decided to take the long road. What I mean is, I went full fledge into my craft, which turned out to be Ancestral Entertainment. Read more>>

Jennifer Popperl

Last year, I lost my mother, an event that profoundly reshaped my perspective on life. If there’s any silver lining to be found amid such a loss, it’s the powerful desire it ignites within us to live. Read more>>

Matthew McMenamy

In high school, we had to make these “four-year plan”s our freshman year around what we thought we wanted to do post-graduation. I had planned my entire curriculum around me being a professional freelance photographer, because I was super passionate about it at the time and had been taking pictures for years. I wanted to be behind-the-scenes, behind the camera, capturing the beauty, not be apart of it. Read more>>

Jamie Hurt

The biggest risk I’ve ever taken was venturing out on my own to launch Jamie Hurt Copywriting. With several years of experience working as a copywriter for various companies, I had grown accustomed to the security of a steady paycheck, benefits, paid time off—all the perks that come with a traditional job. However, after experiencing three different layoffs, I quickly discovered that job security wasn’t a guarantee—even in large, established companies. Read more>>

Monica Edwards

For the past 9 years or so, I’ve had the great pleasure of living a life as a painter. I’ve never worked so hard, struggled so much, lived so frugally and been so happy. Read more>>

Matthew Nagy

I feel like I’m always taking a risk with the direction that I take with my music. If you don’t take risks and push boundaries, I feel there isn’t much of a point in making art. I’m definitely not afraid of trying unconventional things when it comes to making music. Read more>>

Carla Williams Johnson

Allow me to take you back to March 2020. Read more>>

Matty Carlock

At 32 years old, I’ve lived many different lives stringed together by risks I’ve taken. Mostly with my back up against the wall. Some unsure, and some extremely confident. One risk I remember specifically is when my band broke up, I could have left it behind and rejoined society and settled down with a career. Read more>>

Ember Henderson

Embracing risks is a valuable endeavor, not only for artists but for everyone seeking personal growth. In 2012, I reached a point where my dissatisfaction with my day job became overwhelming. The thought of adhering to someone else’s schedule and contributing to a company with values and morals that didn’t align with mine made me feel disheartened. Read more>>

Paola I. Neri-Michel

I knew I would have my own law firm at some point. I took a big risk when I decided to make the dream a reality during an uncertain time. I opened my law firm in February 2020, and as we all know, one month later the world shut down due to the global Covid-19 pandemic. Read more>>

Natalie Clark

I always had a passion for music but I didn’t think it could be my life and career. So for years I built up my life in Scotland, going to University and eventually becoming a school teacher. I kept doing music but it was a part-time passion, and after a few years I finally got the courage to quit my job and pursue music full time! Read more>>

Brian Hyman

One of the biggest risks I have taken in my life was getting sober. I was 34 years old, and had no idea what sobriety, recovery, or spirituality looked like. I didn’t know anyone who was sober. I didn’t have much money, I didn’t have health insurance, and I wasn’t sure how to approach the recovery world or how to access any sort of treatment. Read more>>

Rhea the Second

I just recently quit my job to pursue music full-time. I’d been investing so much time and energy into other peoples dreams and businesses that I lacked the time and energy necessary to successfully support my own. The idea of quitting was really scary at first. I was mainly afraid of financial instability. In addition to rent and bills, I was funding my first full project. Read more>>

Sam Frontino

Taking the leap to quit a well-paying job and start my own business, Aerial Pointe Drone, was indeed a significant risk. The decision wasn’t made lightly, it required significant belief in my entrepreneurial abilities. The fact that I was unhappy with my previous job I think shows my determination to pursue my passion and create something meaningful. Read more>>

Makayla Larson

Choosing to want to pursue an entertainment career was a hectic journey. I had absolutely zero support in the beginning and my mind was just full of “what if’s”, “what if I don’t make it”, the embarrassment of pursuing your passion, and just being let down with negative comments from peers is insane. That in itself is taking a risk, you never know how it’ll all play out. Read more>>

Zech Francis

I’ve had the entrepreneurial bug since I was 9 years old. From that young age I’ve been obsessed with branding, design, and creating products that consumers love. I launched my first apparel brand at 12 years old, bought my first screen printing press at 15, and by the time I was 19 I had a clothing brand that was selling in popular retail stores across the country, from Nordstrom, Bloomingdales, Buckle, and many more. Read more>> 

Bri Bolling

In October 2019, my career took an unexpected turn when I was laid off from my position at a marketing firm due to downsizing. This job had been a dream come true for many, as it was a women-owned business renowned for its innovative approach to the career industry. Among its enticing perks were unlimited vacation time and a weekly concierge service, with the added bonus of allowing employees to bring their children to work. Read more>>

Mariana Fernández

I moved to the United States from Venezuela in 2014, having already secured a job as a journalist. Since then, I have taken three risks that changed my life. Within a matter of days, I discovered that everything was a deception, and I was forced to accept a job that paid me only $400 a month. Read more>>

Christoph Jesus

I got started as an artist and performer with little preparation. As soon as I learned a few chords on guitar with a couple of my first original semi complete songs in hand, I immediately submerged myself into the open mic scene performing for hundreds of people a night. I embraced my enthusiasm and excitement for creativity and used it as an ignorant confidence which worked in my favor because I was so blinded by passion I was unafraid to fail. Read more>>

Antonio Valdovinos

2020 gave me the push I needed to take a risk on myself and start this business I had been longing to do. Even as a teenager I knew I didn’t want to work for anyone else, but I had children at a young age and was supporting our family while my partner stayed home with the kids and worked part time. I would mention my idea to people and a lot would laugh, I’d like to say it didn’t hurt or discourage me but I am human. Read more>>

Courtney Lyneé

The only risks I took growing were getting on rollercoasters! I was a dare devil back then. However, after college and having my daughter, that started to shift. The rejections in high school and college were beginning to take a toll. I had a hard time taking a chance on me. That started to unexpectedly shift during one of the worst times in my life: the Pandemic. Read more>>

Stefan Gustafson

Once with my photography, I felt I had reached a flatline. I had felt my work wasn’t evolving nor was I getting recognition. I them decided to completely revamp my studio and reconstruct my portfolio as boldly as I could. The financial investment used to construct the studio was rather large. Read more>>

Laura Luna

I have taken many risks in my adult life. I think when you are first generation, taking risks is a big part of the journey to success. Looking back, I think the greatest risk I took was to move to a different state to pursue a romantic relationship. I was 28 years old and met a person I connected with. He moved to Austin, TX a month after we met. Read more>>