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.

Eric Schmidt

I went to a performing arts high school in Florida and did some TV/Film coursework in college but never thought anything like that was a realistic career choice, but then I moved to New York and just a few months in, while on the job search, my Mom called and told me that my cousin’s friend had worked at the Late Show with David Letterman in the page program and asked if I might be interested in doing that. At the same time, I was offered an office job that paid more, but would have been WAY less rewarding. I made a list of pros and cons and the office job totally won, but I was like “eh, I’m gonna do the Letterman thing anyway.” Read more>>

Linda Sudowski

Starting a business is always risk no matter what. And man have I taken some risks! In 2015 I left my career as a social worker to open My Make Studio. We had a small space with about 20 seats for people to come in and decorate cupcakes and cakes. I had no idea what I was doing but day by day I found my stride and grew my vision. We hosted parties, classes, summer camps and cupcake battles. In 2019 my lease was up and I took a huge risk by moving My Make Studio into a larger space with foot traffic. Read more>>

Reis Paluso

Let’s face it. We all like to be comfortable. Our lives are designed to be so. We have food when we need it, transportation to take us wherever we need to go, a house over our head with temperature-controlled rooms, entertainment galore, and so much more. Now more than any time in the history of humanity do we have a cush life. But what does all that comfort mean? We get complacent. We expect things to happen for us. We don’t push ourselves. We don’t listen to our gut for what we actually need, especially when it comes to being happy with our work life. It is easy to just show up, do your thing, and get a paycheck. But that leaves many of us feeling empty, worthless, and disconnected from purpose. Read more>>

Matthew Baker

I moved from San Diego to San Jose to assist with improving operations for a large hotel and conference center. I worked my way up the ladder to executive sous chef. At the time, I realized being deaf would hinder me from being promoted more. Working in a busy kitchen my communications was limited without an interpreter. After being passed up for many opportunities, I moved back to San Diego. Feast on This became a goal of mine. I love food, catering, events and wanted to create opportunities for others who felt like the “underdog”. Read more>>

Kelsey Rene

It seems like my entire life, and each accomplishment, is doused with risk. Growing up, it went without saying: just about everything I envisioned demanded that I live and become dauntless. I *wanted to perform on stage. I *wanted to be a great dancer and actor. I *wanted to be seen. I *wanted for girls that looked like *me to be considered marketable, considered a worthy talent with potential. In high school, none of these wants were a reality yet, but I lived (even as a teenager) as if my time could come at any moment. I tried everything. Read more>>

Hunter Jones

I can’t emphasize enough on how important taking risks are. Taking a risk could severely change your life for the better. Through my high school years of life I became really depressed because I hated living in Conroe, Texas. As a creative, I felt like Conroe wouldn’t be able to provide me the necessary opportunities I needed to move forward in photography or anything creative for that matter. Thankfully because of Robb Klassen who was a photographer for The Hundreds at the time, was able to land me an internship for The Hundreds in Los Angeles, California. Read more>>

Micah Robbins

In 2020 in the middle of the pandemic, I was deeply unhappy in my corporate job. I wasn’t being creatively challenged or using my degree in writing in any meaningful ways. I knew I was capable of more, but no matter how much I asked, I wasn’t given the opportunities to use those talents. So I started freelance writing on the side. Slowly, I build momentum and started earning decent money from it each month. Read more>>

Shelby Stratton

In November of 2021 has been the biggest risk I decided to jump full into my personal business and step away from teaching at any studio or for anyone else, in 2017 I stepped away from the Corporate world and started my own business, but always worked as a contractor for studios and business, while running my business . With the past 2 years and the climate of the fitness industry and taking so many different pivots over the past 2 years from teaching many classes in person a week before pandemic to closing down and being out of a studio for months, to learning how to record and teach online classes, I decided it was time to step out on my own. Read more>>

D’Erika Gaines

Business is all about taking risk, as well as entrepreneurship. I didn’t know exactly what I was getting myself into prior to starting my business. However, I did know that I no longer wanted to work a 9 to 5. Long story short, I was tired of my current job I had working as a receptionist at a medical clinic. I’ve never had a job that paid me a decent amount of money. I’ve always knew I had many talents, the hustler and drive to get what I want by any means. At this time, I was dealing with so much in my personal life and decided I was going to quit my day job and start making wigs and selling them. Read more>>

April Day

Going back to school at 36 years old felt like one of the biggest risks I have taken thus far. After working in various jobs that felt unfulfilling, I decided it was time for a change. I saw a Naturopathic doctor to address my severe adult acne, chronic hives, and digestive issues after seeing several other practitioners who informed me there was nothing that could be done for my conditions. I tried all the available prescription medications which only helped temporarily. I never considered being a doctor but my experience with a Naturopathic doctor felt unlike any other interaction in a medical setting. She had compassion, she listened, and she took the time to investigate why I had these symptoms. Most importantly, she gave me hope that my body could heal. Read more>>

Full Trip

One of the biggest and most important things to do is believe in yourself especially because sometimes you’re the only person who sees your vision , It can be very risky because which means you’ll have to put up a lot by yourself , that means you’ll have to sacrifice the majority of your time ,energy and own resources until other people start to catch on or start supporting your movement , the music and fashion industry are both easier than ever to get in which also means it’s harder to stand out , Read more>>

April Fitzpatrick

In July 2013, I decided to the leaf of becoming a practicing artist. My grandmother has passed in January of that year, and I was struggling with the lasting impacts of grief. In between jobs, I began to paint to externalize the grief, depression, and anxiety. The question of what did I foresee regarding my life followed me. I phone a friend who encouraged me to watch a documentary called The Secret. This somehow led me to the life of Jean Basquiat and from that moment I wanted to rely on my creative self. Read more>>

Scott Elliott

I graduated as an engineer. A few years in the industry, I came to realize that this was not my passion. The daily responsibilities of being an engineer became a struggle due to lack of passion and desire to improve. The struggle bled into the rest of my life and I saw myself becoming very passive aggressive with family, friends and work relationships and girlfriends. I fought the inner voice to change, because of the investment to graduate with this degree and the fear of disappointing my family. Read more>>

Shay Koloff

The biggest risk I ever took was starting my own business and next to that it was moving to Colorado. I had come from a very traditional family and many of them work regular jobs. When I first became a mom, I tried working many jobs and different schedules but those never really worked out for our busy family. It was in 2019 that I decided to take the first step into owning a business. It was just me and a bag of beads, I had no idea what I was doing nor what I was making. Read more>>

Vicki Oduba

After freelancing for several years in the events planning industry, I decided to take a risk and turn my hobby into a profession. I started by registering my business name and then taking tons of professional classes to gain more knowledge. It didn’t stop there; I invested in my design business by adding unique inventories and started offering virtual courses for beginners. I did this all while building a vegan cosmetics line. As challenging as that was, it was a risk I’m glad I took because it started a beautiful journey. Read more>>

Kermel Yohannes

I’ve taken a lot of big risks to become a full time filmmaker and entrepreneur. I moved from Texas to the East Coast then all the way to the West Coast (and still moving around for sure). I started filmmaking in Dallas, where I grew up, then moved to Boston to attend Emerson College. I studied film production and business extensively. From there, I was able to be a part of our Emerson LA program, where I was able to have an internship at a film production studio while attending classes in Los Angeles. Read more>>

Raditia Lasry

It was November 2003 in China Town NYC at a place called Good World. When my friend started talking with a stranger born in Switzerland, where I am from, we acquainted ourselves. At the end of the night, this stranger and his friend offered us a ride to a subway station nearby. As we got closer to the station, he asked us where we lived. As we shared where we lived, Elmhurst Queens, he decided to drive us out there as he knew how to get there. My friend and I didn’t question it and let us drive close to our home. Read more>>

Kari Reyes

Since the moment we are young, in grad-school, and on our way to leaving high school or college we are told to follow our dreams and to take the risk. We never truly know what that risk is until we are living it and always knew it would be worth any challenges we would face. Since I moved to Texas in 2013 I only knew one thing, and that was what I wanted for my career. This was to be a professional wedding and event planner. I had every person tell me it would never work, I could not do it, and it was a waste of a career. As I knew this truly was not an easy road, I was not going to let bosses, friends, family, or church groups be negative or to tell me otherwise. Read more>>

Alek Smith

This is the story of the biggest risk I’ve taken thus far in life. I moved to dallas at 18 with somewhat of an automotive tech background. I grew up in Connecticut and loved my youth there – it was just time for something new after high school. I was working a roadside assistance job during the day and worked nights at UPS here in dallas for almost 7 years. I was making good money and living a comfortable life. My girlfriend at the time (now fiancé) pointed out that sometimes it seemed i was on autopilot. Read more>>

Nandi Nelson

Back in 2017 I decided to take a risk and leave my full time stable job to pursue my dream of opening a therapy practice. When taking the leap of faith I was very scared but thought the worst thing that could happen is I go back to my full time job. With that being said I took the first step and registered by business with the state. I then started the pre-work of what needed to be completed in order for me to structure my business to gain clients. Read more>>

Suki Eleuterio

When I first started my business six years ago I was so scared to hire a coach. It was such a risk. I kept asking myself, “How can I justify it? There’s not even much money coming in. A few clients here and there. How can I spend that money?” The truth was I was all over the place with my business. I was overwhelmed, overworked, and underpaid. I felt unnoticed, unheard and undesirable. How could I get myself out of this rut? Read more>>

Janay Lewis

A few years after I graduated from cosmetology school, I decided to take a risk and move to Houston,Texas with my son with only five hundred and ninety eight dollars to start my life over. For the first year, I worked as a hairstylist at hair salon called DryBar to learn the skills I needed to become a professional. While working at the salon, I also got a chance to learn how to properly run a business as far as scheduling appointments, keeping up with inventory, etc. Shortly after, I decided to quit my job to take another risk to start my own brand called Gemini Tresses. Read more>>

Trisha Wolf

One of the biggest risks I’ve taken was leaving a full-time steady job as a musician and moving to a new state without a job or much of a plan. I knew the job I was at wasn’t a good fit and couldn’t see continuing with it into the future but I didn’t have a clear vision of what else I wanted to do. Eventually a little idea started developing in my mind for a small business creating music for ballet class, but I didn’t have much confidence in my abilities to see it come to fruition as it was way outside of my comfort zone. Read more>>

Deyari Evergreen

Me choosing a career in the creative world of music and design is without a doubt the biggest risk I have taken in my life . The path I chosen is unorthodox to the norm of going to school , getting a education , & finding a normal occupation but what good what would it be to me not pursue my dreams with gift I have been blessed with. It hasn’t been a easy one nor did I expect it to be , but I know the rewards are going to be worth it whenever the fruits of my labor start to appear . In all honesty looking back on my life I believe this lane in the creative field chose me . Since I can I remember I’ve always been infatuated with art & music , so you can say it was destined to be . Read more>>

Andres Hernandez

Man, taking the risk with music is 100% the biggest gamble. Everything with writing lyrics, recording in the studio with new artist, showing new material to strangers and the biggest one….performing your finish work in front of strangers. I remembered when it came to an opportunity to perform in a showcase contest to compete with other artists, that was one of my most scariest moments in my entire music career. I never performed in front of people before, this was definitely a big fear for me. I didn’t know if the crowd was going to like my music, if they wasn’t going to like how I sounded or worse of all, I feared that I would forget my lyrics on stage. Read more>>

Alan Pugach Barker

I knew from a young age that I could not work for someone else’s vision, it just wasn’t going to be in my story line. From my comic book “APB” which is a nonfiction, to my sweatshirt line, the music production, now footwear, this is all a risk I’m willing to take because it comes with meaning and purpose, what I create isn’t just a creation, there’s importance behind what I create, there’s a reason why I decided to share my story in my comic book, there’s a reason why my sweatshirts have a silhouette of a hooded figure, or that I decided adding the two English quotes on the sleeves, why I used Classical Latin on the nimbus of the hooded figure, why the footwear is inspired by ancient art. My work turned out exactly as I thought it would so far, this is only stage one. Read more>>

Jennifer Kosharek

My life has been full of unexpected twists and turns, risks that I had to take because there was no other choice but to sink or swim and risks I fully jumped into. For example about 12 years ago I was faced with a husband leaving me and our three children. I was a stay at home mom and had not had an official job in 13 years. Instead of taking a normal job… I started a full time art career and opened an art gallery. Not only did I not sink… I thrived swimming in the art pool. The eve-N-odd was a wild success and I thoroughly enjoyed being a full time artist and gallery owner. Read more>>

Patricia Frischer

My parents supported me while I attended undergraduate school. but when I wanted to get a master’s degree, they were not sure if I was wasting my time. They said that if I could get a scholarship, they would continue to help me with rent. That scholarship that I received was the proof that they needed, and I became a star student, graduating with my master’s degree in sculpture from the California College of Arts and Crafts in 1972. I was offered a teaching position straight out of school, but I turned it down to travel to Europe where I had never been. Read more>>

Sonya Jacobs

As a teenager in the 90’s unsure of myself and my future, I took a life changing risk and said “yes” to my nineteen year old high school sweetheart when he asked for my hand in marriage in 1993. We were not sure of who we were, or what we were going to do for careers or who we were going to become as adults. We had no money, no degrees and wide open futures. However, we knew that we loved each other, were better together and wanted to get old together. The risk proved to be challenging as we grew up together and into adulthood. We finished our degrees, served on the mission field, struggled to start a family, Read more>>

Andrew Cooley

One of, if not the biggest, risks I’ve ever taken was going full-time into esports. In 2011, I received my degree in Financial Planning from Texas Tech University. However, in my senior year, I also started my first company, State of Mind Gaming, that was designed to be a professional esports organization – I really wanted it to become known as “Dallas’s” team since I was born and raised here and likely will never leave. Read more>>

Meriah Davis

Placentas are not typically something a lot of people want to chat about. Putting myself out there as a woman who works with other women’s placentas is socially risky, lol. Especially in today’s propaganda-drenched atmosphere of shunning or demonizing those of us who value nature’s medicine, the freedom to choose what we put in our body, and finding alternative solutions to medications. We are often referred to as “quacks” or “crazy hippies” and honestly I sometimes think I would be burned at the stake if that were still a thing. But throughout my life, Read more>>