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.
Ricardo Jiménez
August 1st, 2022, I found myself sitting at gate B23 realizing the full extent of what I was about to embark upon; A year of solo travel around the world. To provide some context, a year before that, in 2021, during the last first semester of my senior year of undergrad, I was nominated by two of my professors to apply for the Thomas J. Watson Fellowship. The Fellowship is one that allows recently graduated college undergraduates to travel around the world for one year, on the condition they cannot return to the U.S. until the year is up, on a purposeful pursuit and exploration of a personal project that they design. After much encouragement from my mother and help from the Dean of the Conservatory, sent in my application, having only decided to complete it the day before it was due. Read more>>
Sanvernetas Thomas
In 2016, I was working on the Production Control team at a Toyota plant in Mississippi. While studying Business & Marketing Management in college, I worked the night shift, all while pursuing my creative dreams of becoming a creative director, wardrobe stylist, and model. My sister, Porsha, proposed an opportunity that changed everything: to move with her to Philadelphia and pursue my fashion ambitions on the East Coast. Leaving my job security, family, and close friends behind was daunting, but the words of my late mother grounded me. She always told me, “Please get out of Mississippi and make something of yourself. I may not be here to see that day, but I need you to take heed”. Her guidance was the push I needed. Read more>>
L8 Nite
I don’t want to be cliche because many people have reached success after being homeless. I’m successful but still have a ways to go. I was building naval ships as an electrician making a lot of money in my younger 20s. I would use the money to support other artists from my home town but getting burned sometimes by industry posers. I loved music and artists more than my current trade at that time. So, I left the opportunity of joining the apprenticeship as a designer and moved to Muscle Shoals to go back to school to learn the business and art of music. While in school, I became a Record Promoter. I assisted in promoting Jason Derulo’s first hit record, along with other artists. I ended up doing my internship in the city of NY. I networked like crazy also visiting some of the Program Directors who I corresponded with during my RP stint. I went back to Muscle Shoals working as a booking agent and engineer intern in the country music industry. Read more>>
Jasen Edwards
I love this question because it feels like I’ve been attracted to risk my entire life. I was told that dropping out of college after two semesters to get my real estate license at the age of 18 was risky, but to me it was exciting. After a couple brutal years, I found a mentor who taught me how to sell and I turned things around. I went on to be a consistent top producer in a cutthroat industry, while most of my competitors children were still trying to figure out what to do with their lives. Then, after 13 years as an agent, people told me it would be risky to walk away and start a new career as speaker and trainer for salespeople. But again, it didn’t feel like risk to me. Read more>>
Aditri Bhattacharjee
One of the most daring decisions of my life was moving alone to a new country and starting a fresh chapter right after the turbulent Covid period. That time was transformative for me; while it introduced many hurdles, it also unveiled unexpected opportunities that reshaped my path. Leaving Kolkata, India, and flying across the world to Baltimore felt monumental, especially as I was doing it alone. No familiar faces were there to make the transition easier, but I knew I was headed toward a place where my dreams and ambitions could finally take flight. Read more>>
Kristen Barrett
I’m not going to lie. Bringing up this part of my past is painful. If you would have asked me 10 years ago where I see myself I never would have seen this coming. I would have said, happily married to a great man raising two beautiful girls together. Coming out to myself was the easiest thing I ever did. Coming out to my husband, the hardest. When I was in my early 30’s I fell for an amazingly brilliant and kind man and we got married shortly after. For many years I was happily married. I was a stay at home mom to two healthy beautiful fun loving girls. I had hobbies and friends and while at times it was lonely in that overwhelmed-stay-at-home-mom sort of way, I had a good life. Like all good suburban moms, I meal planned and sang my babies to sleep. Read more>>
Jenny Lee Maas
To be an artist and business owner taking risks is required again and again. I would say the decision to follow my own path was and still is the greatest risk. I have had many other jobs and in all of them I felt a lack of fulfillment for various reasons; everything from low wadges, mistreatment, not being considered as an equal creative to my coworkers and simply just that it wasn’t a place for me to push myself creatively. Read more>>
Melesha Oglen
Taking the big risk to write, produce and direct my very first Indie film is truly a risk I never ever seen myself taking. I always knew that producing a Stage Play based off my books, was a lifelong dream, but film is a whole new ball game. I decided that what is life if you are not willing to take risk? So that you never live a life of wondering what could have been. My talent and imagination could not only entertain, but truly bring the visions I have to life. This life has handed me a lot of disappointments, so taking the risk and facing my fears would be well worth it. I embrace the good and the bad. Read more>>
Maria Cid
It’s March 2020, and I’m about to graduate from the BFA in Acting program in Mexico City. We just started rehearsals for our graduation play when… yes, the pandemic hit. We went home with innocent smiles, joking about how our “one-week vacation” suited us perfectly. But that week became a month, then two months, and so on. With little to nothing happening in the acting and modeling scene, I decided to visit some family in Atlanta and help them with their kids while things “went back to normal.” (Spoiler alert: nothing went back to normal.) Read more>>
Latoya Taylor
I left the salon chair after 13 years this year in June. Going into the clothing industry and my artistry. Is something alive always loved. It’s a risk because I saw my clientele plummet. People just can’t afford certain services any longer due to the changes in their families and or careers so I had to make a change for mine. I stopped pretending like it was working when indeed a transition needed to be made because I was l getting bored. It had to make sense. Clothing makes sense because you cannot go through life unclothed. Going into full entrepreneurial mode with your family takes work but team work. Everyone has to be on board. Now I can, not only fully express my true self and true artistic identity but now I do not have to depend on others to clothe my family. It’s fun and inspiring. Read more>>
Chelsea Williams
In 2020, I started my own catering business called “Let’s Roll”. This consisted of variations of different flavors of egg rolls. It was so successful that I dropped to part-time hours at my full-time job and put it all on the line. However, with success and taking risks also come with disappointments, lessons you will learn, and opinions on running your business. Ultimately, I took the risk because I’ve always had a passion for cooking. It’s one of my love languages and its honestly a stress reliever. When I started this business, I didn’t have the right people around me and lacked confidence, which caused me to close my business at the end of 2021. Read more>>
Carole Smith
The biggest risk I’ve taken in my life wasn’t necessarily the moment I picked up a pencil—it was the moment I chose to truly share my art with the world on my terms. Like many artists, I started out by imitating others. For a long time, I was figuring out who I was as a creator, mimicking the styles I admired to learn and understand the craft. Through this phase, I stumbled upon photography—particularly action, nature, and portraiture. These subjects began to speak to me, especially in relation to myself and the hip-hop community I was so deeply involved with. As I grew, my style evolved too. Read more>>
Julia Scott Papiernik
You know what they say, “big risk, big gain.” That never felt more real, until now. In January 2022, fig™ Buffalo was formed. At the time, I did not realize the gravity of the risk or the massive undertaking we were about to embark on for this platform. The fig™ Buffalo platform is composed of four risk takers, Julia Scott Papiernik, Newell Nussbaumer, Sarah Bohn, and Jim Kupczyk. We pioneered the uncharted waters of the fashion realm in Buffalo, NY. We decided early on to go big or go home. Our production was going to be top notch, sponsors high level, and showcase exclusively cut and sew designers from Buffalo and/or producing in Buffalo. Our platform tapped into the zeitgeist of Buffalo fashion designers. At fig™, we are dedicated to empowering and celebrating local cut & sew designers and creators in Buffalo’s burgeoning fashion industry. Through our platform, we provide a space for the community to engage, connect, and celebrate self-expression. The fig™ Buffalo platform is not just a fashion show; it is an all-encompassing experience that fosters creativity, inclusivity, and the vibrant spirit of our local fashion community. Read more>>
Christi Slaven
I took the huge risk of believing in myself and starting my own business. There is so much self esteem and self worth wrapped up in taking the leap from a regular paying job to the world of small business start up. Even though my husband, friends, other family members, and even clients were constantly telling me I need to make that change I doubted myself for years. I didn’t think I was good enough, Let’s back up to the beginning. I was suffering from sciatica so badly that I truly believe the pain would’ve killed an elephant! On top of that I had a locked up ankle, a bum knee, a frozen shoulder, and a trigger thumb all on my left side. I tried the traditional path of modern medicine, but their answers were shots, drugs, or surgery. None of the doctors I went to would believe that these issues were connected to each other. These professionals all had their specialty and they never took a look at the whole body as a unit. Unfortunately, this is the norm in the medical world. Read more>>
Stacey Hammond
I started my creative journey over 30 years ago in an uncreative way. I was teaching 2nd grade in public school. I wove art into everything I taught, even math. I loved it, I was happy teaching there and making my art on the side. I was 26 when the county went bankrupt, and they began massive teacher layoffs. I had always wanted to start an art program and this hiccup was the perfect opportunity. The teacher who taught 2nd grade across the hall had an Ed master’s in computer science and we decided to leave and start an art and computer school. We researched the left/right brain learning experience, got a loan, leased 6 Macs, bought a kiln, and built an amazing creative space called FYI-For Your Imagination. Read more>>
Nicoya Mothershed
I remember working my butt off feeling burnt out and like I was missing out on being able to make moments with my family. Here I was a single mom of 2 at the time, always having to be away from my children in order to provide for them. I was literally working every weekend and would be swamped during the holidays as a stylist at Floyd’s Barbershop. I was desperately thinking that there has to be a better way to make ends meet. But I had not the slightest clue of what that was. Then out of nowhere due to unexpected circumstances, I lost that job. I was freaking out and panicked wondering how was I going to pay my bills. Instead of looking for work something told me to work for myself. Read more>>
Olivia Martin
I’m a big believer in taking risks. Opening a business is a huge leap, but the rewards can be substantial. Taking risks is essential for growth, especially when building a business. The biggest risk I took was leaving the comfortable shop environment I was in. I felt stagnant and knew I wanted to establish my own brand and values. In October 2022, I took the leap and signed a lease for my own suite. After a four-month break, I had to hit the ground running, reaching out to old and new clients to let them know I was back in Lansing and doing nails. My first suite provided invaluable experiences, and when an opportunity came to move into a shared suite, I took it—though it didn’t turn out as expected. It was a reminder that not all risks yield immediate rewards, but every step offers valuable lessons. Afterward, I took on a new suite investing more in monthly expenses, a big financial leap at 19. Thankfully, it paid off, and my business flourished. Read more>>
Phoenix White
One of the most significant risks I took was stepping into the role of a psychedelic therapist and plant medicine facilitator—a journey that felt like a calling from the medicine itself. This adventure began with a bold leap of faith when my family and I listened to the call and made an international move to Mexico. There I found myself engulfed in learning about ancient healing methods and started to train and learn from incredible shamans and medicine women.. It was a transformative experience that opened the door to profound mind blowing expansion so I embraced it. At the time, I was navigating becoming a new mother with a five-month-old baby, as well as brain surgery. I had learned to be cautious about anything that could impact my mental and physical health. The stigma surrounding psychedelics was pervasive, and I was acutely aware of the fears and judgement surrounding them. I don’t advocate for reckless drug use; instead, I see plant medicine as a natural, sacred tool for healing. Read more>>
Andrea Stokes
I started my career in the field of community development working cross-culturally. Through studying and working in Uganda, Sierra Leone, and South Asia, I noticed a pattern: when girls lack education and economic opportunities, it leads to human trafficking. I began to see a huge need for safe and sustainable job creation – a void that can only be filled by profitable, fair businesses. Seeing the enormous need and with a practical, empowering solution seemingly within reach, I could not look away. This was the vision behind Swahlee, the business I started in 2018 to create employment for at-risk young women who face barriers to employment in South Asia. Read more>>
Jxjury
The biggest risk I’ve ever taken in my life? I’m currently living in it as we speak! Growing up in the IE (southern California), there were three things that moved my spirit the most – basketball, music, and fashion. I was an avid sneakerhead, who loved to play basketball all hours of the day, and made my own music. I knew at a young age these were the things I wanted to spend my life’s work in. So I began to carve a path that would allow me to do all 3 of these in the corporate world. I had this crazy idea of working in Nike Basketball at the Nike WHQ in Beaverton, OR. I wanted to inspire the world like those Michael Jordan / Spike Lee commercials we watch growing up – “Mike, it’s gotta be the shoes!” I wanted to make THAT. It was an unheard of dream where I came from, but it was my dream job. Read more>>
Erica Davis
After decades of working in health care, I realized that my climb up the corporate ladder was no longer the path I wanted for myself. As I looked, many of my professional colleagues and mentors didn’t have the life I wanted for myself, or my family. Riddled with stress, often prioritizing their job over their own health and relationships with their family, I knew it was time to step down from that ladder and step into something new. I took a four month sabbatical and found my true calling. My passion project, leading a women’s mountain biking group, and helping women improve their health through mountain biking, was now becoming my true vocation. It was one of the biggest risks I had ever taken, but I knew it was the right path. When I returned to work after my sabbatical, I stepped down from my leadership role, took a part time position in order to maintain my health insurance, and began my journey to becoming a women’s health coach. Read more>>
Itzel Oregon
I was invited to work on sofia coppola movie. I was terrified because i was intimidated by only the idea of working for her on the movie “On The Rocks” for mexico scenes. I thought i wasnt prepared for that amazing oportunity but i decided not to listen to my thoughts and just go for it. At the end everything went amazing. She and the makeup head department were both happy with my work . So, i learned my lesson, just go for it. Trust youself. Read more>>
Karissa Mathis
I was always interested in nails from the application shape and design I got very influenced to start Nails through TikTok every nail video I came across I watched and never skipped. I figured with my creative skills and liking to draw I could learn and pick up as a new hobby so I took the risk. I went to my local nail supply with a budget to get everything I needed to start. That night I practiced my first set it wasn’t the best set but I was just starting out and all that mattered to me was that we took the first step. Pretty much from there on out I became obsessed with getting better everyday I would lock myself in my room and practice non stop the application was the first step to complete before even thinking about designs. Read more>>
Adetayo Ebo
The Leap That Changed Everything One of the most unforgettable and symbolic risks I’ve ever taken wasn’t a career move or financial gamble—it was a physical leap into a cenote in Mexico. A cenote is a natural sinkhole, formed when limestone collapses to expose the groundwater beneath. To fully understand why this moment was so significant, I need to share the backstory. In early 2022, I had just completed my master’s degree, stepped away from coaching soccer, and landed what seemed like the perfect corporate job at an event marketing agency in New York City. It was a role I thought would be my next big step—exciting, stable, and prestigious. But as the months went on, I found myself feeling unfulfilled. Despite the outward success, I realized my true passion lay elsewhere—not behind a desk, but on the field, working with athletes, and helping others transform their lives. Read more>>
Emily Lopez
I took the risk of being more open about my design style to become a better Art Director overseas and work as a Freelancer. This thought started when I used to work in ad agencies, although I appreciate all the experiences and I’m grateful for them, I began to think that I wanted more. So one day, I decided to be impulsive, so I sold everything and moved to New York. I’ll start my creative way from another angle, the angle that I’ve been imagining for a long time. So I did it, but unfortunately, a few months later, the pandemic arrived. it had a positive side because I could study more and try new opportunities based on the circumstances, so I started to post on Social media very often with every skill I learned until one day, I woke up and a big page of design share one of my projects, so after that great and talented people and opportunities arrived, Read more>>
Beth Buffington
Risk. It’s encountered every day when you’re a creative. Especially if creativity becomes your business. Each time a canvas is turned around for someone to “see”…there’s risk. Each look a creative “gets” brings elation or rejection. Creativity requires creatives to infuse their soul into their work. But, when it is time sell their work—emotions must be removed. “It’s not personal… it’s business.” The 180 degree swing in focus in order to be profitable… is palpable risk. It can feel like bungee jumping… without the bungee. As a creative coach, I teach the importance of creative confidence to build emotional strength and maintain creative fire. Understanding how to embrace the risk of letting the world “see”…and then being able to manage the the high of approval… or the free fall of rejection… is a skill that must be learned and then maintained. Read more>>
Star Spann
When I was 20 years old I thought I had my whole future set for me, yet despite this, I was quite unhappy. I had wanted to be a singer since I was a kid, and ended up in theater as a way to sing on stage. I had dedicated my life to the theater, I took dance, acting, and singing lessons, went back and forth to NYC to auditions, and was preparing to leave for college to get my BFA in Musical Theater. When straight out of high school, I booked a job as an actress in a regional theater in my home state Virginia. I thought this new job would be the first step to my broadway dreams, but it ended up doing just the opposite. I worked at that theater for two years, and in that time I realized I couldn’t do this forever as my lifes work. Read more>>
Cassandra “cassie” Karch
One big risk that I took was publishing a part of my life story, when I wrote my first book Identity Cry-Sis. Being vulnerable and transparent with who I was while growing up, who I am today and who I am becoming. It was a scary thing to tell my story but there are times when you must do things afraid, especially when you are walking in your purpose. When God gave me the assignment to start writing, I didn’t understand it then, but now I see it’s because I help so many people through that gift. One thing I learned is that if you have children, and you plan on publishing a book about yourself, make sure to sit them down and tell them first. They shouldn’t have to read about it along with everyone else. Read more>>
Michele Beardsley
At the age of 48, after working my dream job for someone else for 25 years, I (along with a coworker in the same situation) made the decision to leave that job. I began doing guitar repairs at a prominent Minneapolis shop when I was pretty fresh out of school. I gradually worked my way up to a full-time position gaining lots of valuable experience and clientele. My boss was very patient, generous, and encouraging, kind of like a second father. I absolutely loved working there. This employment bliss continued for about 15 years. Things began to turn sour, due in part to nepotism. My coworkers and I tried many times in many ways to make things work like they always had; meetings with the boss about what could make us feel valued and not taken for granted, ways to improve our outlook and the business itself. These attempts were always met with uninterest and lack of sympathy. I continued on there for the next 10 years as things got worse, frequently angry and unsure of my future. Read more>>