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.

Abby LaFountain

In high school, I was a top-performing student, multiple extracurricular activities, and a strong work ethic. However, despite my outward success, I felt like an outcast and struggled deeply with depression. To cope, I turned to motivational speakers like Les Brown and Eric Thomas, which eventually led me to other influential figures like Tony Robbins, Grant Cardone, and Robert Kiyosaki. Read more>>

Carly Eads

I would say going into owning a photography business right out of high school was one of my biggest risk I’ve ever taken. At that time, I really didn’t have a huge clientele built up yet. I was doing good, but I for sure didn’t have a solid income. It was definitely scary thinking that if this plan of opening up a photography studio in Kokomo failed, I didn’t really have a backup plan. It taught me patience, hard work, and that if you don’t try it out you’ll never really know! Read more>>

Stephanie Benedetto

I was married to a man I loved, and we owned a business, home and house full of animals together. Five years ago, I made a choice to leave it all behind. It was a difficult decision, and one I took my time making to be ensure that I was leaving from a place of clarity and peace, rather than an escape. I’d always lived in New York and had spent most of life living in the town where I was born. I didn’t want to stay there simply because that was where I’d always been, so I left with two suitcases and began life as a digital nomad traveling and pet sitting. Read more>>

Quineitra Shelby

My life has always been about risk taking. I moved to Houston on my own when I was 18-19 and I didn’t know anyone there, had no family, but I had a dream. Houston for me was the pre test for everything God is preparing me for now. The move to Houston changed my life so much because I learned how to trust God & figure it out in any circumstance because my parents weren’t 10 minutes away anymore. Read more>>

Octavia Jones

I had been working at my job in the health field going on 5 years, while also serving part time in the military. There had came a time shortly after my military contract had ended, where I had a “what’s next?” “This can’t be all there is to life” moment. I decided to take a lash course, which in turn landed me in school for Esthetics. This literally was a split decision almost overnight. No real thought behind it. Read more>>

Jeremy Kellem

Taking a risk is more about a mentality than it is an action. Many risks that I have taken in my early adulthood had to deal with my professional football career and the creation of my business. As I exited college I began looking at my options to play pro football. My agent at the time told me about a workout for a Professional league that he set up for me. Read more>>

COURT DANYELLE

The biggest risk I have taken is fully having faith in my God- given gifts. The year is 2014 and I am working full time and going to school full time. I was pursuing an idea to become an Anesthesiologist. Thoughout my life I thought I wanted to work in medicine to be able to pour into people in their time of need. I then experienced my own medical emergency in June where my appendix burst and I had no idea. Read more>>

Vicky Collins

I grew up in Hawaii. In paradise. The biggest risk I took was leaving my family and friends behind and moving to the mainland which opened the door to so many things. I remember when I was growing up in Honolulu I met people who had never left the island. That was not for me. When I was about 16 I got restless and bored and could not wait to broaden my horizons. Read more>>

Rechelle Conde-Nau

It had been a difficult year. Our youngest was in the throes of teenage rebellion times twelve and we felt like our heads were barely above water. We wondered how we could possibly come out the other end intact. This seeped into other areas of my life and I found my usual joy for life hard to muster. Separately, there were a series of events that were wrongly interpreted by someone I had thought of as a friend and we had a falling out. I managed to survive by advocating for myself and by taking the high road. Read more>>

MEME

In my life everything I’ve accomplished has been built from the momentum of the risks I’ve taken. Graffiti is illegal and you can only make a name for yourself by consistently breaking the law over a long period of time. I had been painting like this since 1999 and for the love of it. Read more>>

SaraBella Abdulkader

As a young Black girl growing up in Brooklyn, NY. I had plenty of big dreams. Dreams of being a household name. Visions of inspiring black girls to follow their Dreams. I decided to follow my faith. The biggest risk I took was moving cross country from New York to Los Angeles. I was only in my 20s. It was a life-changing risk. All I had was my faith. I knew I had to trust in God. Read more>>

TeeCee Cribb

Taking a risk. Deciding to step out on faith and walk in my calling. A urge was rising in me to create a women’s empowerment event. But, not just the typical conference. Something, that would encourage women to come together, create a spiritual community, develop a relationship with God, understand it’s okay to be transparent and authentic, creating connections and networks. Fear took a seat and just rested on my chest and mind. Read more>>

Betsy Byler

One of my great joys in my career has been the opportunity to be a clinical supervisor and the director of an agency. This wasn’t something I ever sent out to do but I ended up in that position out of necessity for the agency. It ended up being one of the most fulfilling things I’ve ever done. Don’t get me wrong I love being a therapist. I love working with my clients and seeing people gain more freedom in their life. Read more>>

Brittney Romero

Deciding to open a business in Southern California and not back home in Northern California is one of the riskiest things I’ve done. Not only did I decide to open a business in a city I’m not from and didn’t have many clients in, but I also moved while we were still in quarantine. There’s still a lot of Los Angeles I haven’t fully experienced yet. Before I moved, I was working for someone and had a thriving clientele. Read more>>

Mary McCurley

Taking the risk was quitting a 9-5 job to become a full time entrepreneur. I wanted to put all of my time and creativity into my business on my own time. I have worked for someone else since i was 15 years old, always feeling stuck at the bottom. I wanted to be my own boss because working so hard for so long for someone else I have earned that right. Read more>>

Angie Krause

After the legalization of marijuana in Colorado in 2012, my clients began asking me about the use of cannabis for their cats and dogs. In Boulder County many households were openly using marijuana for both recreation and to improve their health or relieve pain. As they saw benefit for themselves, they wondered if their feline and canine family members could also benefit. Read more>>

Elana Casey

Taking a risk. I was in middle school. My brothers had both gotten into catholic High School. And, it was my turn to continue the tradition. The all girls catholic high school. I didn’t consider where I might want to go to high school, I just knew that was where I was supposed to go. I remember going through the interview process and the principal telling me that there will be no Prince Charming to save you. I had to be dependent on my self and my merit. I ultimately applied, but didn’t get in. Read more>>

Laren and Aimee Loveless

Aimee: Taking a risk is scary. There’s so many unknowns in leaving the comfort of a steady paycheck. What will others think? Will we be able to pay our bills? What if we regret the decision? What about retirement? All of these questions stirred around in my head for months before leaving my teaching career after 13 years in education. I loved teaching and had a very meaningful job as an ESL teacher. Read more>>

Olivia Talbott

I think the biggest risk I’ve ever taken was the risk I took when I moved to Los Angeles with no job, family, partner, friends, and only $1,800 to live with two strangers. I had known my whole life that it was where I was supposed to be. I had a few different dreams, and one very clear one. All of them seemed to be in Los Angeles. I faced a lot of loss in exchange for my risk. Read more>>

Aaron Loving

A big risk I took when I was younger was dropping out of high school after my mother passed away & pursuing my music career full time. I didn’t have a plan or any idea how to accomplish what I wanted to accomplish. All I knew was I was extremely hungry for success & I was willing to lean/do anything to make sure I see success. Read more>>

SKELA aka Sanguine Skills

Being a creative is an everyday risk, and living off of your creativity is the ultimate risk. Because from now on whatever comes out of your heart will always be open for criticism and celebration. I have been taking risks all my life. I’ve lived in countries, I don’t speak the language, I’ve tried all kinds of jobs, I’ve used machines and tools I never thought I could and I’ve done it all on my own. Proving to myself I don’t need anyone has always been super important to me and that’s why 9 years ago I took the biggest risk I could imagine. Read more>>

Anet Khechoumian

The biggest risk I have taken to date, would have to have been traveling to North Korea ! Every aspect leading up to the trip ( and successfully exiting ) was both exciting and terrifying. I have always found a interest in a country that has been black listed and isolated by so many, and have been curious to witness the people and places that are often portrayed in varying forms of media. the arrival was very exciting and had a sense of privilege attached ( that you are being given permission to enter). Read more>>

Kym Tolson

A few years ago, my boyfriend and I decided to take a leap and become digital nomads. We left behind the traditional lifestyle of owning or renting a permanent home and chose to explore the world by living in Airbnb’s, moving from place to place as we worked remotely. At first, the transition was difficult as we had to adjust to living in new environments and moving to a new home ever couple of weeks. However, we quickly fell in love with the freedom and flexibility that came with being digital nomads. Read more>>

Laura Weiner-Kiser

In a weird way I’m pro risk. I fear looking back on my life and thinking, I wonder if or when or why. It’s lead to some ups and downs but I’d do them all again. However, I got a little spunky when I decided to start my business. Most people think about it for years, have a business plan, etc. Not me! I thought it was a good idea to start my business as the pandemic hit, while I was relocating from Chicago to St. Petersburg, Florida, in school, newly married and had become a vegetarian a month prior. Read more>>

 Dorothy Cross

Working in the dental field for eleven years. I was tired of corporate work. I was trained as dental surgical assistant and traveled all over Dallas to help train new graduates and then they would work for big dental companies. My turning point was in 2021 when my dentist at the time saw me in a different lens and said I needed to find my passion outside of assisting and training. So I took and extra courses to get started with my teeth whitening business and launched it in April 2022. Read more>>

Tess Dodd

When I was a kid, I always swore that I would never work in an office. It just seemed so… mundane. I couldn’t imagine sitting in a little cubicle doing who knows what on a computer all day everyday. What did I want to do? Well, that changed. A lot. I think my first real career goal was to become a veterinarian. That lasted until I found out I’d likely have to put animals to sleep. It’s possible the dream of singer/songwriter came next. I remember writing songs and making up dances with my neighborhood friends and putting on shows at our street’s block parties (are those even a thing anymore?). Read more>>

Lady M

Taking a risk as a female in the entertainment especially being lgbt is something that takes A lot of guts. To be yourself and not care what people think is a big motivation I try put out to the world. I have been professionally involved in the music industry for over a decade and so much has Changed and I have achieved so much by being me and not giving up and being consistent. No matter who called me crazy or who thinks I won’t make it it’s all about believing and staying focused. Take that risk. Read more>>

Rod Macdonald

I’m a graduate of Columbia Law School. By the time I was in my third year I was playing clubs and coffeehouses around New York City, and when I graduated I blew off taking the bar and kept playing music. People say “Oh, it’s good to have something to fall back on.” I though that was wrong and ignored them; I thought, if I am going to succeed at it, I have to dedicate myself to it, not think about “falling back.” A couple years later I met Dave Van Ronk, a legendary folksinger from the 1960s. Dave asked me “Is there something else you could be doing?” I said no. Read more>>

Kalo Sikalumbi

A recent risk I took was traveling to New York to model at NYFW shows. Me and a few friends didn’t know what we were getting into but we made the most out of the situation! I ended up walking for 3 designers at RiseNYFW & 3 designers at Coastal Fashion Week. I’ve been modeling since 2018 & ever since then it was always my dream to travel to New York for fashion week. However, it’s a dream that I’ve constantly been putting off since then & I felt like now, 2023 would be the perfect time for me to go! Read more>>

Akeem Jackson

I never knew what risk was until the age of 18. Risk was presented to me in the form of poverty. Risk clouded my reality. It was risky to continue living. It was risky to walk down a certain street. It was risky taking a regular job. When would I leave the job? Would I be there forever? Maybe life then, was so risky, people didn’t like taking any. “Life is hard enough, as it is”, my mother, would say. Read more>>

River Bonds

When I first began my career in real estate, I had no true direction or understanding of what would be the outcome. The pandemic caused me to be laid off from my corporate job and with so many uncertainties in the world, becoming a full time entrepreneur did not feel like the safest choice. On the other hand, I know that with great risk comes great reward and that was a chance I was willing to take. Read more>>

Leandro Taub

When I was 24 years old, I decided to leave Argentina and search. It was an interesting risk. I gifted most of my belongings, took a flight to Europe, and that journey that started 15 years ago, already took me to live in Germany, France, Slovakia, China, India, Mexico, and the United States. Read more>>

Matt Brown

I dream of becoming a professional podcast host and producer and from there, I want to create a Podcasting/Media Network. I produce and host a podcast called the Productive Conversations Podcast and I want this podcast to lead to my own network. I have always dream of having a career in the media and communications. I originally saw myself as a TV showrunner, I wanted to create TV shows or become a TV executive. However, I have had a hard time finding my footing in starting my career doing that. Read more>>

Christopher Ferguson

When I first decided to take the biggest risk of my life, I understood that many people would hold me accountable for the decisions that I would make for them as a life coach. I knew that I could no longer live like a regular person because the weight of the world was destined to be on my inexperienced shoulder, but I had the determination in my feet to run a good race and it has been a victorious race so far. Read more>>

Alicia Boyd

It was a big, life changing risk to decide to pursue Humble Hearts Catering & Events as a full time profession. I was in a position, in my personal life, where I had just became a cancer survivor. I had a good job and was moving up the career ladder through out my company. But I was still unfilled. Humble Hearts was on the back burner of my mind but I was still longing to be a business owner and I was longing to do it through catering. Read more>>