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.

Dana Hayes

The biggest risk I’ve ever taken in my life was the risk I took when I got sober. I didn’t know what the consequences would be. Would my friends still want to hang out with me? Would my husband be embarrassed of me? Would I be able to walk with my head held high in the leadership role I’d assumed for myself as an online coach, mentor and business owner? Would colleagues and clients take me seriously? The unknowns were limitless, but so were the possibilities… At the time I was a marketing coach. Read more>>

Velvet Star Chong

I can vividly remember the day when I peaked in my patient’s room on the oncology floor at Holy Cross Hospital. The look of peace and serenity that filled her face was so comforting. The pain medications and other treatments being offered did not give those results. She had no idea what the nun did with her hands but she felt so much better. The nun explained to me that she was doing a complementary therapy called Healing Touch. She offered me a scholarship but with being a very scientific minded new nurse, I declined. Read more>>

Ashleigh Montford

Being born, taking my first breath as a melanin infused human in America in 1993, walking outside in 2022, daring to educate myself through higher education and pursuing social justice and equity as a changemaker – all risks. It may seem as though success happens over night, and truth be told – I am still trying to make it. However, one of the biggest risks I have taken professionally, would be deciding to have a business, having two businesses. Read more>>

Michelle Sanchez

Becoming a business owner is the biggest risk I’ve ever taken! One thing about me is I can be a little bit of a control freak, especially since I handle the finances in our house so I know what we need to support our family. I’ve always worked since I’ve hraduated high school as a W-2 employee and would do hair and makeup here and there but nothing crazy. Until 2020 hit and because of all these canceled weddings, my makeup business started to take off. Read more>>

Jonathan Cyphers

In October 2021, I moved from New Hampshire to Nashville, TN, to pursue music full time. I had taken a few trips over the summer to write songs and network, but this was a pretty big deal for me. I was moving away from family, friends, community, everything I had known and was comfortable with to pursue something that had no guarantees. I only had a few friends in Nashville, had never lived outside of the Northeast, and didn’t even have a place to stay lined up when I packed my car and started the drive down. Read more>>

Krissy Graban

” If you got a chance, take it, take it while you got a chance If you got a dream, chase it, ’cause a dream won’t chase you back If you’re gonna love somebody, hold ’em as long and as strong and as close as you can Till you can’t” ‘Till You Can’t’ by Cody Johnson This song and these words summarize pretty perfectly my path to owning a barre studio. 2021, a rollercoaster of a year for many; I was no exception. It was the year my son was born and the year I lost my mom. One night, I was up late on the couch working; Read more>>

Kamyra Cheatham

Anytime you put yourself in a position to do anything outside of what is considered the “norm” you put yourself under a lens, and you don’t know just how people are going to perceive you once they’ve realized you are doing something “different”. This was me, 6 years ago doing something “different”. When I went vegan I had so much success with my lifestyle, from almost completely getting rid of my anxiety, to losing weight and being an all around happier person. I was so happy with myself and this new way of cooking I learned that I decided I wanted to help people, so I did. Read more>>

Kevin Smith

In 2016, I left the events industry to take a job in a new and unfamiliar field. I didn’t leave the industry because I lost passion; my decision was simply about personal and professional development. OK, I won’t bullshit you, it was about money. I gave my new career choice a couple of years, but ultimately I was unfulfilled. Read more>>

Therapii

I’ll never forget this. I was in high school at the time. I was a junior and the clock was ticking for me. “What to do after high school? …choose a college from my electives? Pursue something else?” The walls were closing in. More than half my family were pushing college or a trade. Something safe. I had other plans though. I’d always felt that there was more to life and that we weren’t here just to live a mundane abc life. At least that’s how I saw things. So I said to myself, what do ‘I’ want? Where can ‘I’ find fulfillment? Read more>>

Sharon Grenier

Coffee Connections started as a catering company with a mobile coffee cart in 2014. We opened our first brick and mortar shop in the heart of downtown Old Hilliard on September 10, 2016. Sometimes our passions can turn into our career. That is exactly the case for Coffee Connections. We had a strong passion for coffee and for people, and combining the two was the obvious next step. Read more>>

Sarah Miller

When I look back at what has gotten me to where I am today, it is because I have taken multiple risks, always betting on myself. I struggled in college to find my purpose. I was taking classes that I didn’t like because it was what I thought I was supposed to do. But there was one day when I finally realized I was on the wrong path and I needed to come up with a different plan! After one quick Google search my life was changed forever. I had discovered Dance/Movement Therapy and I knew in an instant that was what I was supposed to be when I grew up! Read more>>

Nico Cortes

As someone who deals with mental health issues on a daily and knows how scary it is to try and get out of your head, if I can give anyone out there reading this article any advice… It would be, DO IT. Just do it! If you have been thinking about something, take that leap. Whether that is moving across the country to get away from a crazy ex and starting over or taking the plunge leaving that “secure” job to chase your dreams. Just F-ing do it! We are only getting older and time moves faster than you think and now that I am almost 38, things hit harder. Read more>>

Paige Harrison

One of the biggest risks I have taken is starting BeeMore Aesthetics. It was late 2020, and I was a new mom navigating the post-COVID world. Like so many, I was feeling disconnected and longing for community. I always had, what seemed like, a far-off dream of one day starting a business where I provided cosmetic neurotoxin services. The use of neurotoxin is a big part of my practice, but for therapeutic indications (chronic migraine, etc) instead of cosmetic, and I am very well comfortable with the medication. So many of my friends were receiving cosmetic neurotoxin, and I thought “I should be the one injecting them!” Read more>>

Chef Sunflower

I’ve taken a lot of risk in life, but the biggest one to date is leaving my 9 to 5 behind to try and run my business full time. It’s not easy to walk away from certainty, but if you have dreams you can’t keep sitting on them and pursuing them part-time or you will never fulfill them. You have to get out that comfort zone. It has been very uncomfortable at first, because it if the money is not coming in, how will you pay your bills and survive. Read more>>

Aunia Kahn

Over the last few months, I took a pretty significant risk and chose to be public about my disability as well as own my identity as a disabled entrepreneur. Stepping up and stepping out about this part of my identity was risky. It should not have to be, but the fact is, that it is. There is so much misunderstanding and judgment around people with disabilities, that being transparent about your disabilities can impact you personally as well as your business. Read more>>

Samantha Ayers

It is all too easy for us to get comfortable in what we do. Put the light over there, stand here, look this way, in all the same locations I have shot over and over again. That’s being comfortable. But how do you grow as an artist if you don’t take risk and put yourself in uncomfortable scenarios to grow and better yourself? As a photographer we have to ensure we are continuously inspired. For me, I enjoy capturing families “in the moment”. Read more>>

Cora Bruffy

Life is a learning and growing journey, and I have had many adventures in my life, and I have never been the type of person to be held back by fear or doubt. The biggest risk came when I first ventured into the wonderful world of domesticating animals and finally found my goats, beginning my best-risk adventure of starting Faeryland’s Farm Menagerie and betting on the goats and me. The farm is a small 501C3 nonprofit animal sanctuary in Baxter, Tn where we rescue animals, do animal education, and do animal healing in the form of animal reiki and goat therapy. Read more>>

Ricky Valido

I have taken the risk of becoming a full time touring singer, songwriter, guitarist and performing artist. It has been a gamble but I have put my art and creative endeavors ahead of everything else in my life. It has been rewarding to take this risk and navigate the music industry as an independent and self contained artist. Read more>>

Priscilla Loomis

Summer of 2021, I retired from athletics. After 26 years of being an athlete, I had finally hung up my spikes for good. Earlier that year I took a job at a local radio station; I became the morning show host while training for the Summer Olympics. (Quick backstory, In college, my professor who taught intro to radio told me to skip radio and go right to television, he always believed the world needed to see my personality and not just listen to it.) Read more>>

Tre Bennett

I believe the biggest risk I’ve taken is deciding to become a full time basketball trainer over this past year. The decision to do so wasn’t necessarily the easiest decision but it was a decision I felt that needed to be made in order for me to reach my full potential as an entrepreneur. I took the risk because I wanted to be more available for my clients year round. I knew that being available part time would only stunt the growth of my brand. I felt that it was time to go all in on my business. Read more>>

Chetelvia Thompson

Imagine having a dream that you can never stop thinking about and the enemy knew about your dream and put everything on your path to make you give up, but you never gave up. That is a risk that you have taken which end up being so many risks to get you to your desired goal. This year of 2022 my whole life crumbled in front of my face. I honestly thought I had life together. Having my own apartment, car and feeling somewhat stable in my early 20’s. Read more>>

Andi Garbarino

Before my life as a Visual Artist, I worked as the director of an after-school music and arts program in Houston. Texas. I had grown up in a highly creative environment, painting with my grandmother and singing to my grandpa playing guitar. I loved putting on skits with my siblings in the living room after dance lessons, and in high school, theater made my heart sing. With a little bit of life in between, I went on to study music therapy in college and left university with a music degree. Read more>>

Faith Schueler

I think the biggest risk I’ve taken in life is deciding to pursue my music career full time and give it everything I have. When I hear the word risk, I think of the word “faith”. Sometimes you just have to have faith that everything is going to work out the way it should. Writing music and putting it out there for the entire world to hear is pretty scary. But I believe when you have a passion and something you feel that moves you, you should allow it to be shared with the world because you never know how your story or your music could impact someone else. Read more>>

Candy West

One of the biggest risks I’ve taken was the decision to follow God and answer the call as pastor. At the point that I was asked to consider becoming the lead pastor of the church where I am, it took much prayer and consideration. It was partly because I was trying to figure out if it was time to move on to something new. I wasn’t sure about what was next. However, it was God’s plan and design that what was next would usher me into one of the biggest decisions of my life. Read more>>

Caleb Reid

The life changing risk that I took was beginning to believe in myself. Having tunnel vision and remaining persistent played a gigantic role! It was not always like this though. My entire childhood I struggled with socialization and self-esteem. Those 2 things alone caused a deep internal battle furthermore, which made it difficult for me to trust myself and my abilities.When i picked up a film camera this all changed. Read more>>

Katherine McFerren & Christopher Commons

Every video production project is a risk. You can’t control everything on the day of shooting and you can’t always gauge the audience’s reaction to a finished product. We’ve had projects fall through, even after shooting. There’s always a time investment that isn’t guaranteed to bring results. We try to break through stereotypes and norms of specific genres, while still creating something artful and authentic. Read more>>

Lee Lee La Cubana

I have always been known to take a risk or two whether that be in fashion choices or career moves. Growing up in urban New York City, my interest in becoming an artist was widely misunderstood which was understandable based on the “starving artist” narrative fed to us by society. Even after attending Fiorello H. LaGuardia High School for Music & Art and Performing Arts which positions creatives to have higher chances in pursuing creative careers, I enrolled in an Environmental Engineering program when I began my college journey because engineering has a great trajectory for society’s definition of success. Read more>>

Joshua Stout

The biggest professional risk I have ever taken, by far, was quitting my office job when my wife was 6 months pregnant, to pursue art full-time. In August of 2019, I left my job with the Chamber of Commerce in Cincinnati, OH to become a full-time muralist. I had several murals in the bag that I had done on the side, but finally felt like I had enough walls lined up, that I had some runway to give it a go for at least 6 months. Read more>>

Gail Allard

I would imagine that the biggest risk I have taken was to step off the cliff of faith and quit the “regular” job to pursue the life of earning a living as a creative. I was an art kid growing up, my mother was a painter and my father was a musician, and I loved the creative aspect in just about any medium I could get my hands on. After high school, I went to college to study for a Bachelors in Studio Art and made it two years before taking a break. Things got expensive out on my own and I wasn’t paying much attention to the core classes, anyway. Read more>>

Krystal Blase

The biggest risk I took was when I decided to quit my full time job back in 2010 and finally pursue photography as a full time career. I had already worked a few years doing photography part time while working my day job and in turn had built a pretty large portfolio while having clients booking me consistently at this point. I think this is what pushed me to really go forward and pursue the dream I had always wanted as my job and make it my one and only career. Read more>>

Gina Motley

I had been braiding for maybe two years before I took my talent serious. We just brought our home and I finally had a dedicated space to do hair. One of one old coworkers reached to make an appointment for a style I never did. I was super nervous all the way up to the day of the appointment. I braided her into the styled she desired and she loved it! This was a risk I took that scared me terribly however if I never took it I would have no idea of what I can do if I mind to it and never under estimate myself Read more>>

Calonda Henry

“If you push through that feeling of being scared, that feeling of taking risk, really amazing things can happen.” – Marissa Mayer, CEO of Yahoo, Inc. Life in itself is a journey of risks. I often replay the quote “If you play small, you stay small.” in my mind on a daily basis. The decision to become a full-time entrepreneur has most definitely been the biggest risk I’ve taken. From full-time job security to a series of uncertain events. Sounds miraculous right? Not quite. This decision to become a full-time entrepreneur was at the height of a pandemic and amongst the new journey of becoming a first time mother. What a time to be alive! Read more>>

Max Freeman

I was burned out from going to med school and dropped out, For all my life I’ve always played it safe, had a plan, and basically did what was the norm until I stopped and asked “what the f*ck am I doing”. So I dropped out of college, traveled around the east coast on greyhounds and picked up odd jobs, surfing on friends couches, living in sh*tty studios. Read more>>

Stacy Beam

Since I was selling horse portraits as a sixteen-year-old, I have dreamed of owning an art gallery. So last March, when my friend sent a group text saying he’d heard about Richland Fine Art closing shop after twenty years in its Green Hills location between Pottery Barn and Trader Joe’s, I was super excited! Less than a week later, my wife, and two of our best friends were sitting around our kitchen table discussing how this might work. Within a month, contracts are signed, agreements arranged, and we are in full demo mode on a renovation project that is being finished as I write. Read more>>

Grace Parsons

I believe pursuing a career in any entertainment or creative form is deemed “risky”; mostly so from the peanut gallery in a negative light. But to the artist-the entrepreneur…the dreamer- the risk of chasing a possibly unattainable dream is the only fathomable purpose one feels. I felt this exact way when I discovered my passion for music could be turned into a career. It was my freshman year at Purdue University in the first semester; I had yet to declare my major. Read more>>

Jessica Falcone

Starting and creating the business, Jessica Elizabeth Skincare was the biggest risk I’ve ever taken. We were just starting to learn and hear about the Corona Virus in 2020 and I literally had just signed a contract for the next 5 years on a space in downtown Syracuse that would need 100% renovations. The lease was out of budget at the time and the space was in dire repair of updates. During that time, not only was I nervous of what my future held with this new venture, but I was also struggling mentally with an ugly divorce trying to balance everything in my professional life and personal life. Read more>>

Amélie G.

One of the biggest risk I took was to leave my country, drop everything (uni, my band, etc) and move to London after winning a scholarship for a music school. When I decided to do this competition, my drums teacher told me I wasn’t good enough, I didn’t have the level for this school. But I knew I would regret it if I didn’t try so I went for it and against all expectations, received an email : congratulations, you start the school in 3 weeks. Read more>>

Ron Landis

Getting out of your comfort zone can be very rewarding in many ways. When I have an idea I believe in, I tend to dive head-first into unknown territory, damn the consequences. And I’ve done it several times. Risks don’t always play out in the best way but I always gain valuable experiences either way it goes. Read more>>

cadence miller

Going into any creative space can be a risk. You are your own company/manager, or at least in my case as an entertainer. I was a bit of a late bloomer, deciding in high school I wanted to be on stage professionally. I remember my parents saying, “Are you sure? You’re going to be broke your entire life.” To which I said absolutely – as long as I’m performing, I’ll be happy. Sure, this life has its ups and down: little to no job security, moving from state to state for different contracts, and typically no benefits (health, 401k, etc.). I think most people have to choose between work to live or live to work. I feel like I get to do both! Read more>>

Colin Peterson

Taking risk is scary. Uncertainty isn’t comfortable, but sometimes it’s necessary to grow and be successful. For me this major step to starting my own pottery business. I moved to Charleston, SC five years ago. I moved to this town because of a job opportunity that had nothing to do with art. It was an unfulfilling position, but a way for me to make money and afford my new life in the city. Though I was making money, I was making it while doing something that didn’t bring me any fulfillment. I had a need, or maybe innate drive to do something creative. Read more>>