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.

Jessica Dawson

My path wasn’t straight from Real Estate studies to Wall Street. It took a detour through the aisles of Home Depot, where, amidst helping customers find the perfect faucet or unclogging a toilet, I learned a different kind of lesson: Read more>>

Celeste Pillows

The biggest risk I have taken was on my dreams. It’s a big price to pay to be your biggest investment. It’s worth it yet it’s tough spiritually because when you move intuitively you have to be more willing to trust whatever knockout comes with it. Read more>>

Micayla Stone

As a child I spent nearly 8 hours every single day training to become a professional ballet dancer. From not ever taking off my costume tutu as a four year old to breaking in my first pair of pointe shoes around the house, I lived and breathed for dancing. Read more>>

Myriam Diomande

When launching Passion Fruit Events, I was working full time at one of the largest consulting firms in the country as a Marketing Manager. It was the opportunity of a lifetime. Read more>>

Celine Moser

When I decided to start my business I had been working as an office manager/secretary for ten years. I held this position for a few companies during that time. Read more>>

Kat Jones

Whew. My journey with risk has been quite interesting. This won’t be your typical story of “taking a chance”. When I was in my early 20’s, risk to me looked like moving half way across the country to chase my dream of becoming a “super successful” professional dancer. Read more>>

Hope Trory

One of the biggest risks I’ve taken in business was starting my own company. During the great recession of 2008-09, I pivoted from architecture into marketing. Read more>>

Jennifer Hsu

I’ve never taken a risk I regretted, but I’ve regretted a lot of risks I’ve never taken. Before an acting career, I was a computer science major in college trying to figure out what I wanted to do for a living. Read more>>

Terrilynn Dubreuil

Who would ever think that a global pandemic would force one into taking a huge risk? Not me! But I am actually thankful in many ways to such a bizarre situation and how it changed my life. Read more>>

Rachel Austin

I have always been a risk taker, sometimes overly optimistic with an “it will all work out” attitude. I’ve lived abroad and traveled off the beaten path in several countries. Read more>>

Mani Saint Victor

You know, back when I was two years and two weeks deep into my psychiatry residency, I found myself at this weird crossroads. Read more>>

Mitchell Ford

For me, the biggest risk I’ve taken was packing up and moving to Fort Worth back in 2021 to pursue my music career. I got the idea late one night in my home at the time in Canyon, TX and started making moves on the plan the following day. Read more>>

Katherin Mendez

Leaving behind my pursuit of a career in psychiatry during my college years to embark on the journey of starting a mental health social club was a pivotal moment for me. Read more>>

Toni Toledo

Risk…sounds like a scary four-letter word (and it can be at times). However, there is one risk that I took a little over 5 years ago that has changed my Life, my career, my relationships and my outlook for the future. Read more>>

Rebecca Corvin

When I first become a mother, I felt as though I was faced with having to choose between myself, my career, my spouse, and my children. Read more>>

Susan Spann

Seventeen years ago, I decided to leave my teaching job to open my own performing arts school for children, and I have never looked back! Read more>>

Jaime Zazzara

In the realm of risk-taking, sometimes it’s the small, seemingly inconsequential decisions that can lead to life-changing opportunities. For me, it all began with a simple message – another whisper from my intuition urging me to reach out to a woman named Carrie Villanueva. Read more>>

Felecity Havens

My life’s philosophy centers on embracing risks and fostering belief in myself and those around me. The most significant risk I’ve undertaken was the day I made the decision to step away from professional basketball and pursue alternative goals and creative ventures. Read more>>

Mary Schnepf

Dance is full of risks, both on and off stage, but I found the challenge of accepting the role as Artistic Director for the Greater Niagara Ballet Company one of the biggest risks I have taken in the span of my career so far. Read more>>

Liana Kangas

Pursuing comics freelance was the biggest hurdle I’ve ever overcome. I was drawing part-time for fun when I was in my previous career, which eventually led to private commissions, graphic design and editorial illustrations. Read more>>

Carlos Rising

In 2020, during the start of the Covid pandemic, my wife and I were working jobs in Seattle WA when both of us were let go by our companies on the exact same day. Read more>>

Makayla Roberson

I started my business in 2020 as a side business. A few months later I was diagnosed with Lupus and Fibromyalgia. I had to put my all into my business and quit my job. Read more>>

Katelynn Johnson

The biggest risk I took, was leaving my full-time job in order to start my cleaning business. I knew I had to leave my full-time job selling cars at a car dealership. Read more>>

Dr. Mikey Ofuani

A story of a risk we have taken is building a family business that better prepares others to minimize the everyday legal risk life brings with the starting of our family business Legally Black Law Firm, know also doing business as Ofuani Legal Group. Read more>>

Flavia Pradolin

I became a volunteer for Safe Haven for Animals ( non killer cat shelter/sanctuary) 9 years ago doing a cleaning shift in the morning. Read more>>

Acacia Bailey

My Very First Live Wedding Painting: It was 2021, Audrey approached me in the busting lobby, she quickly asked “Is there any way you would paint my wedding… live?” Read more>>

Therés Amee

I feel many of my career choices have been underlined with risk. I grew up in a family that was very much wanting me to follow the societal rules of ‘success’. Go to school, get a degree, get a job, work your way up. Read more>>

Precious Asoro

In the bustling city of Lawrenceville Precious Asoro dared to dream big, taking a leap of faith by opening Edged Events, an innovative venue unlike any other. Read more>>

Dr. Adrienne Stein

COVID was an extremely difficult time for most people, and as a practicing naturopath who worked in a brick and mortar clinic full time, seeing patients in person, and recording notes in a written file, lockdown totally wiped out my practice and my income. Read more>>

Kelly Konis

Silverwork Studios, a make your own jewelry studio in San Rafael, California, was co-founded by best friends, Amy Fitzgerald and Kelly Konis, who met on the high school swim team in Amarillo, Texas. Read more>>

Deborah Franklin

One of the biggest risks I took occurred during the pandemic shutdown. During one of my private prayer and meditation times, I felt the familiar nudge to shift from teaching school to counseling. Read more>>

Ricky Borba

I think the biggest risk you’ll ever take as an artist, is on yourself. Americans are taught from a very early age that the safest route to “success” and “freedom” is to play it safe and get the nine to five, two weeks vacation, a spouse, 2.2 kids and a white picket fence. Read more>>