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.

Sade’ the Writer

I am a native New Yorker, born and bred. Escaped for 4 years to Virginia for college, but ended up right back in my comfort zone of Long Island. The biggest risk I’ve taken recently is moving to Florida. I knew about 4 people here prior to moving and had only visited Tampa once before–but it was extremely brief. The urge for this risk came about during quarantine. The time alone in my own thoughts, I was forced to really sit with myself and analyze my purpose in life. Read more>>

Jamison Fox

As a creative, or in my case a songwriter/artist/manager, you take a risk every day. Whether it’s sharing a new song, releasing a new song, working with a new artist/writer/producer, posting to social media, giving industry advice/guidance — it’s all a risk in one way or another. You risk vulnerability, being misinterpreted, your mental health, your relationships, your time, investing your hard-earned money; I could go on and on. I know this isn’t a specific risk, but it’s my truth and hopefully others inside and outside of the industry feel less alone reading this. Read more>>

Jess Malli Mercier

I was sitting at my kitchen counter at a bar stool working on my outdated laptop, that, honestly, may as well should have been held together by duct tape. I had just taken a huge plunge. I got a Silhouette. One of those fancy vinyl and paper cutting machines that were all the rage, I had been dying to get one. They were a somewhat large investment, but my husband made it work that year for Christmas. Read more>>

Bereshith Adams

“The harder the struggle, the greater the triumph,” was a quote I got out of a fortune cookie while eating lunch at the South Dining Hall at UCONN. It came at the right time because I was struggling financially and I could not afford to be there. Prior to starting the fall semester, some of my friends thought I should either drop out of college or go to college back home in New Jersey. Quitting was never an option because I felt that if I did leave, I would never finish. I told my mother that I was never dropping out of school and that I am not coming back home until I get my degree. Read more>>

Allen C. Gardner

I’ve taken a lot of “risks” throughout my life, and maybe the biggest of which was moving to Los Angeles when I was 18. I remember a lot of people telling me that making that move was risky. All I knew was that I simply HAD to do it. Whether or not something seems risky doesn’t ultimately factor into my choices. After all, the outcome of any situation is never guaranteed, no matter how much of a “surefire bet” it is. I don’t do things because people might perceive them to be risky or because they don’t think they’re risky. Read more>>

Jordan Lewis

Currently doing this interview from a coffee shop in the Upper East side of Manhattan. I moved from Houston to NYC yesterday— a move that made me miss the deadline for this interview nearly twice. Only two weeks ago, I decided to leave my beloved Houston and blindly follow my fashion dreams in the city I fell in love with when I was 13 years old, but was always too scared to live in. Read more>>

Giavanna Maddalone

A risk that I took recently was going all in on my real estate career. My first course of action after graduating High School was to get licensed. But I took a detour and started working on a finance degree. I did this because I wanted to have a “Fall Back” plan and I thought it would pair well with my real estate career. But then I realized that I was hurting my career more by not going all in. In my lectures I would be researching properties and stepping out of class to take phone calls on deals I was closing, Read more>>

Josiah Holwick

“Life shrinks and expands on the proportion of your willingness to take risks and try new things.” – Gary Vaynerchuk Creative endeavors are by their nature are uncertain. Starting a freelance business carries substantial risk; however, embracing the inherent stress of fluctuating income pays dividends. Read more>>

Renee Villanueva

When I started going to community college, I didn’t think I was smart enough to make it into a University. I was studious and made good grades but I thought a University was out of my reach. I talked about a University being my next stop after community college but I didn’t actually believe I would get in. I too scared to take the SAT’s in high school, when I started ACC I started in remedial math, I took my first online class and failed and I had to pay some of my tuition out of pocket which meant I couldn’t be in school full time so I could work full time to pay bills and tuition. Read more>>

Nadia Ghahkenshah

It is the summer of 2018 and I have a very important decision to make. Do I stay in my hospital laboratory job – the “responsible” job that pays well and fits into the “ideal” career path for someone coming from the Middle East? Or do I take the risk and turn my filmmaking hobby into a career and take the videographer job – the creative job that is definitely more intimidating and could possibly ruin my passion for filmmaking? Read more>>

Valerie Aiello

Twenty years ago I decided that, if I had to have a job, then I wanted to move to Los Angeles, roller skate around and design album covers like the guy in Xanadu. Once I had a Bachelor’s degree in my hand, I loaded up a small trailer full of stuff to make the move from Austin to LA. With $200 bucks saved in my pocket, a pipe dream, and one month’s rent paid in advance for a room in a house with roommates I found online, I started my job hunt. Read more>>

Samuel Sirmons

The risk of not chasing your purpose, your passion, your dream is too large to ignore. I couldn’t, even when I wanted to. I knew that radio was what I wanted to do with my life during my time at Ball State. I couldn’t find a station to land at in the Indianapolis area. Thankfully, I had extended family offer me the connection to intern for a station in Atlanta for the summer. Once I got that opportunity, I wasn’t going to miss the chance to make it in the biggest urban market in the country. Read more>>

Jeannette Roberes

Entrepreneurship is for risk takers! Risk-taking enables and encourages innovation. Successful risks provide opportunities and failed risks shape future business strategies. After founding Bearly Articulating in 2015, I decided that risk would be my companion as I work tirelessly to create resources for underrepresented populations. I’ve been told no more times than I remember and yes equally as many. I began my company as a tutoring service, and later an educational consultancy. Each phase represented challenges and each time I pivoted to serve a greater good. Read more>>

Leslie Jordan Garcia

Like so many, the recent and on-going pandemic presented me with an opportunity to keep my reliable leadership position that could provide a steady check with little to no advancement and decreasing fulfillment or to shift my side hustle into my full time business. This was not a choice that I could financially afford to make lightly or alone. I talked to my husband. He was super-supportive but really no help. LOL. But he did say something that I mulled over. Read more>>

Kael Jackson

On September 1st of this year a week after turning 25 I packed my belongs and moved to Nashville, Tennessee to further my career in music. This has by far been the biggest risk I have taken in my life thus far and it has been both thrilling and terrifying. I had been planning a move to a larger city with a more active music scene for years but could never narrow down where I wanted to land or the funds to make such a move. Read more>>

Anastessia Bettas

I went through a phase in my life where I had the opportunity to make a life changing risk and leave the dot com world and pursue a lifelong ambition of becoming a professional artist. I always imagined I would be an artist. I was the kid at school with the “best artist” label. I won the visual art award upon graduation from high school but embarked on a corporate career path after graduating from McGill University and the University of Toronto. I worked in the marketing and dotcom industry and needed to regain a creative outlet outside of work so I started taking art courses to build a portfolio and then applied to art school which I then attended part-time. It took me about seven years to complete a three year Fine Arts diploma. Read more>>

MyBrothaVan

Taking a risk; a leap of faith, is what it all comes down to in the end. You can have the money, the knowlege, the connections, but at the end of the day we all must take big risks at some point to earn big rewards. I took a big risk moving to Austin last December. I had only one person I knew living here and didn’t have much money as I was purchasing a house as well. Read more>>

Renee Steward

About 6 years ago, I was working a corporate job managing retail stores for a big company. It was fun! I got to talk to people every day. I was learning so much all the time. My path forward in life was laid out for me. While their were a few directions I could take, the corporate structure is pretty straight forward and you always know that there’s another step you can take. Read more>>

Jonnika Parker

Running a business is taking a risk. You take a risk to be your brand, the face, the professionalism, and marketer. There are many more hats I could speak but that’s just to name a few. In the performing arts industry we take huge risk because our companies fluctuate by season, modernism, costs, popularity, etc. I love what I do and I have taken risk since April 2016, just jumping completely out there and going for it. Read more>>

Chris Cherrie

In May of 2021, I quit my day job to pursue photography and videography full-time, at least until I got another full-time job. I originally started the job in 2019 as an office administrator. As my employer learned of my other skills including graphic design, video editing, and photography, they began to expand my role. In 2020, the pandemic began, pushing all of the organization’s activities online, which gave me significantly more work and pressure. Read more>>

Tara Dente

I moved from Asbury Park, New Jersey to Nashville, Tennessee in October of 2021. I had grown up in Jersey, with a 2-year adventure in southern Vermont from 2015-2017. I had gone through all the “normal” channels of childhood and young adulthood in education, ultimately earning a bachelors degree in psychology and a minor in women’s studies in 2011. I worked in the mental health field for about a decade on and off in many different positions, with my favorite population being adolescents. Read more>>

Stacey Sprenz

I would definitely say taking the risk to jump from education into a photography business was life changing. Nine years ago I was embarking on a second career as a special education teacher. My husband had retired from the military and it was finally time for me to have a “real” career. Read more>>

Anna Astwood

I was a victim of sexual assault at age 12 and a victim of teen dating violence during high school. I spent most of my 20s and 30s as a high school counselor. I began to notice my students involved in abusive relationships and there really wasn’t much education or awareness of teen dating violence. Up until this point, I had never disclosed my sexual assault with anyone and only a few people knew about my experience with dating violence as a teen. I felt compelled, pulled even, to do something to help bring awareness to teen dating violence. Read more>>

Rachel Ward

The biggest risk I ever took was during the summer of 2020 – a pandemic had taken over the world and everyone was staying indoors, working from home, and minimizing any physical contact with friends and family. It was a weird and a new time for everyone – and we were all adjusting to what was our “new normal”. Everyone had their own way of coping with not being able to physically be around one another, whether that be baking, having zoom happy hours, or playing board games. I chose a different path – by applying to be on reality TV. I didn’t think much of it when I saw the ad on Twitter, but figured it would be a fun way to fill my time. Read more>>

Josh Stokes

I have taken the risk of following my dream! Since a child I’ve been blessed with the gift of music and creativity. I know my purpose in life is to inspire through music, and art. With so many amazing, talented artists there are around the world, so many people work hard for the opportunity to perform on the highest level. So this lane is always flooded, and unfortunately this business has become a pay then play situation which can become discouraging to an Artist. Read more>>

Tywana Royal

Any entrepreneur has to be willing to” Take a Risk”. you don’t know the outcome of the situation, so there for you take a chance to see if your idea works or if will it fail. Investing your own money and time is also taking a RISK. How hard are you willing to go after your dreams? Me starting my business was a RISK, I did not know the outcome of starting a business. But I took the Risk. Read more>>

Lauren Umstattd

Establishing my own solo, cosmetic surgical practice is risky. In the financial sense that is. It’s extremely rare for a surgeon to go out on their own and build a private surgery center. Why? Because the world of healthcare is extremely complex and costly. From construction to engineering to supplies to state licensing to staff, every piece of the puzzle has to setup just perfectly to ensure the environment is one in which patients and the surgeon succeed. Read more>>

Lauren B Martin

As a creative ,we take risks all the time right , what we do is risky.However creating a project and getting it made ,brings on a whole other level of risk taking. I have written and produced and starred in two of my own projects .Convincing talented people to trust me ,jump in the creative waters with me, and trust the process. Not for the faint of heart .Everything is on the line .”You are not special ” and “Reality sets in’ were loaded with life lessons . Read more>>

Sallie Holder

The biggest risk I’ve taken is ditching my legal and COO level career in pursuit of what truly set my heart on fire. To paint the picture I had just received a Young Professional of the Year award and was dubbed one of the “Best and Brightest 35 and Under” by the Chamber of Commerce. I had felt like everything had culminated to this moment and I could say I was officially successful. Fast forward to that night and I couldn’t stop the tears as I realized that this wasn’t what I wanted to do with my life at all. Read more>>

Chancie Neal

When I was 13, I walked on to Luke Bryan’s bus and told him that I wanted to be an artist. He told me to get his guitar to play for him, so I did. Being a kid, I didn’t even think to be nervous. I just played. He took a risk on me by asking me to tour with him for seven years. I moved to Nashville during that time and wasn’t sure what to expect. My career continues to go into different directions, but most recently, I became a Mom on the 4th of July. Read more>>

Wynter May

There is a quote by Mark Zuckerberg that says “The biggest risk is not taking any risk.” and I couldn’t agree more with this statement. Taking a risk is always scary, but it’s so necessary! Over the years I have had to take a leap of faith and choose to follow my dreams no matter the cost. I believed in myself and I wouldn’t be who I am or where I am today if I never would’ve risked choosing my dream over my 9-5 or choosing to still go to college even though I was 6 months pregnant. The risk is always worth the reward! Read more>>

James Crutcher

Moving from Idaho to Utah was one of the biggest risks I’ve taken. I practically left my entire life behind just to move out. I used to work at a Mercedes and Porsche dealership as my first job and my second job was a parkour and gymnastics coach in the evening. I enjoyed both jobs I had but one of the other coaches I worked with told me about this place opening up in park city called Woodward and he said he applied for a job there, he then gave me the idea of applying for the job as well. Read more>>

Arielle Richardson

When I decided to have bariatric surgery, it was a big decision, a life changing one! at the age of 32 not only did I have sleep apnea, but I was also diagnosed with type 2 diabetes and high cholesterol. My doctor explained to me that my liver and kidneys were functioning above normal and that was not a good sign. This all came in a flash and led me to a life changing decision which led me to my podcast. Read more>>

Linda Ndlovu

I think for me the risk I took was actually starting to be in front of the camera because I had always wanted to but I was always scared. I honestly did it because I had a lot of support for my friends and I was like “what the heck” let me do it and try it out and if I don’t like it then i can say I tried it at least. I am honestly glad I did it because I have found something that I really enjoy to do now. Read more>>

Gary Fields Jr.

The biggest risk that I have taken so far, was to actually pursue the journey of entrepreneurship. While having a job/career to depend on a steady income, I realized that the only way to guarantee my income was to develop a set of skills that would ensure I would always be able to make a living for myself and my family. I have worked a few jobs in my lifetime, and I have learned that the people who are always guaranteed a reliable income, are the people who create a job or career for themselves. Read more>>

pallavi cherukupally

The first life changing risk that I took was leaving a job with the faith that I would obtain one that I truly wanted. Growing up in an Indian household, it was taught to be safe in decisions and dont leave a job without having another lined up. At the time I had been through all the schooling, then 4 years of residency, and then a hospital job for almost 3 years. It was not what I wanted to be doing for the forseeable future. I took a leap of faith, applied to fellowships in what I truly wanted to do and quit my job with nothing on the horizon. The thought was leap despite the fear. Read more>>

Honey Darvas

At the age of 38 I enrolled at the AVEDA Institute of Atlanta which was the biggest risk I had ever taken in my life. At that time I was teaching at the university level after spending five years earning my Ph.D. in Theatre Scholarship and Directing from Wayne State University. My whole life had been on a trajectory to complete my Ph.D. and teach at the college level. However, after six years, the instructor position that I had occupied and worked so hard for was not going to turn into a tenured position and I was going to be let go. Read more>>

Mateus Mueller

believe that the main risk taken in the whole process of creating the company itself. it was the simple fact of trying something new, of stepping out of their comfort zone to start a new project outside their normal area of ​​activity, but observing the needs of several clients. Read more>>

Alessandra Guth

At the start of this year, I was living in Austin and working a remote 9-5 job in marketing. My life felt still. My brain felt stagnant. I hadn’t written poetry in months, my content was getting promotional–I wasn’t feeling it. I kid you not when I say an Instagram DM changed the trajectory of my year. I was planning to move to LA in June, but anticipated a new marketing gig to pay the bills. Instead, I chased a dream of working in entertainment. Read more>>

James Dalton

Deciding to open the gym in the first place was a tremendous risk. The amount of time, hard work, and sacrifice needed to build a small business from scratch is monumental. It can put a tremendous strain on all other parts of your life. Not to mention the fear and doubt that can paralyze most people and stop them before they ever start. My dad, my brother, and I dealt with this while planning to open JD’s Gym. We wondered: what if we fail? What if we lose a lot of money? What if no one supports us and we deeply regret the entire venture? Read more>>