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.

Charlie Kim

As musicians and actors, we are trained to take risks in performance. This is where true art lies– reacting to each other in real time in front of an audience where stakes are high. Read more>>

Andy Araya

Stepping out of high school and going into college was something I wasn’t expecting to do to pursue any career of my choice. I always associated career moves to higher levels of education in which I decided to enter college with a shroud over my head that would cloud my path. Read more>>

Paige Davis

As a young and newly licensed esthetician I decided to take a leap of faith and pursue my dreams of starting a new business venture. Read more>>

Tyler Williams

Taking a risk with investing in my career my whole life by myself has led to many rewards that I wouldnt have gotten if i was afraid to lose money and mess up my credit. It took time and being broke for years but now all that is paying off. Read more>>

Annelle Johnson Elder

I took a chance and a risk for a better life. I left Albany, NY, and headed to the south with hopes for a more positive life with two small children: Read more>>

Britney Slater

After graduating from Central Michigan University with my Bachelors in Elementary Education I was beyond excited to begin my journey as a teacher. Read more>>

Pamela Clemens

As a child, risks were not something I liked to take. I was very breakable with casts, splints, slings and crutches being a much to common addition to my attire. Read more>>

Beth Carr

I never wanted to step back into visibility. After my hard slog in NYC as a working NYC actor, telling stories of humanity from the stage and screen, I retired. Read more>>

ORICHA PLAVSIC

Taking risks is something we’re way too familiar with. Starting Wisdom and deciding to open a brick & mortar was a big risk we decided to take, a huge one at that. Read more>>

Ellen Matis

In 2022, we made a major shift in business to focus our efforts entirely on social media marketing for tourism-centric businesses and organizations. Read more>>

James Thurman

In May 2020, as the COVID pandemic was sweeping the USA, I was diagnosed with Mantle Cell Lymphoma. After intensive chemotherapy and gene therapy over a span of 17 months, I have been cancer-free for nearly two years. Read more>>

Vedant Kothari

I wouldn’t say that I am a serial entrepreneur but I will say that I have started a few companies throughout the past few years, mainly focusing on the creative aspect of things.. Read more>>

Raquel McCorvey

Pastor Keion Henderson once spoke in his sermon, “How to Heal,” about how you could be stuck at a job and how God will remove the job from you so you could be the entrepeneur Read more>>

Abby Garner

In 2015, I was offered a role at Apple which would relocate my family to California from Wisconsin. My husband David and I were both born and raised in Wisconsin, including our parents, and their parents. Read more>>

Andrea Holt-Roysdon

The two biggest risks I’ve ever taken both include relocating. First, I relocated back home to Okinawa, Japan from Arizona upon graduating college without a job or any idea what was going to happen. Read more>>

Kevin Arrow

In 2022 I developed a new method of working that produced immediate results and seemingly infinite possibilities. Using colored paper, scissors and white glue I began folding, cutting and gluing paper during every available opportunity. Read more>>

Emily Cox

The classical singing world is NOT for the faint of heart. From the outside, it looks like a calm and very docile art form. Read more>>

Jocelynn Jasper

I’ve always worked in sales. I’ve always done well. I think back to how much time and energy I’ve invested into multiple jobs and how I’ve helped companies build wealth. Read more>>

Andrei Kogolenok

When I was 15 I dreamed that one day I would move to Hollywood to become an actor. I made it my goal to get better at English and started taking acting classes. Read more>>

Samantha Shepherd

One of the biggest risks I’ve taken in my career was leaving corporate to start my own content creation agency, The Social Shepherd. Read more>>

Gabrielle Pippenger

At the ripe age of 23, I decided to leave my job as a Marketing Manager for an agency and jump into the world of entrepreneurism. Read more>>

David Michael Slonim

Painting is not about communicating a pre-conceived idea; it’s a process of discovery. Discovery requires experimentation. Experimentation requires real risk. Read more>>

Summer Taylor

As an entrepreneur for almost twenty years, my entire career has been built on taking risks. From quitting my stable corporate job to start my own freelance business, to expanding my business offerings through partnerships – each step was a risk, but they all led me to where I am today, and I wouldn’t change a thing. Read more>>

Tyrica Nicole Young

After the unexpected loss of my aunt, Tonya S. Williams, I found myself grappling with grief and a profound sense of introspections. Read more>>

Karen Calastri

I started painting as a curiosity. I had never gone to art school, and frankly, did not know how to draw. I had discovered pottery and especially enjoyed hand- building vases, platters, bowls, etc. Read more>>

Kirstin Leigh

Risks…according to others, my life is full of them. I moved from a tiny town in Kentucky to New York City when I was barely 18. Read more>>

Chelsey Peters

Isn’t it terrifying to step out into a new world? That’s how I felting August 2014 while having a discussion with my cousin over lunch about the idea of becoming a cosmetologist. Read more>>

Raissa Oliveira Da Silva

It’s interesting, when life shows you in the many ways that it does; that you are meant for something. How many times will it take for you to take that leap? Read more>>

Masayoshi Haynie

They say there’s no reward without risk, and for me, I couldn’t agree more. My risk I took starts with me betting on myself, by pursuing my degree in law. Read more>> 

Katherine Moskal

Hey there, I’m Katherine Moskal, the driving force behind Katherine Moskal Health Plans. Today, my world as a health insurance specialist feels incredibly distant from where I stood during the early days of the COVID-19 pandemic. Read more>>

Paula Anderson

In 2014, I decided to return to school because I was seeking a change. I enrolled at the University of Memphis to pursue a second bachelor’s degree. Read more>>

Maximus Perez

The fear of risk. The hardest part about accomplishing your dreams is the first step. The first step is a big risk that’s filled with uncertainty and fear. Read more>>

Andrew Pollack

I’ve been a professional working artist for over 25 years. As a kid I had jobs in restaurants and the like, but never felt it as a career. Read more>>

Erkin Sağsen

I was living in Ankara when we first started our most successful band. I was studying law back then. Even though i really wanted to make a career in music since i was a little boy, my future was uncertain. Read more>>

Iliana Sanchez

I was about 25 when I was working a 9-5 for a large financial corporation as a banker. I began to dread the next day knowing it would be exactly like my last. Read more>>