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.

Michaan Cross

All of this is a risk. I have wasted money trying to get help from the wrong people. I have done the research and still missed a step. Its all a risk. Example, when I was in the process of creating my labels. Read more>>

Talina Jenkins

Thank you for allowing me to share my story about taking a risk. The biggest risk I’ve ever taken was on myself by startin Talina yourHost. Read more>>

Kiki YuChin Tseng

The biggest risk I have ever taken was moving to the US all by myself when I was 16 to pursue my dream as a professional dancer. It had been my dream to dance outside of home, see the world and put myself out there. Read more>>

Dr. Amanda Speights

For thirteen years, I had the immense privilege of walking the familiar hallways of east coast public schools. The echoes of children’s laughter and the gentle scent of crayons clung to my clothes like unseen threads. Read more>>

Amber Fant

As a black single mother, navigating the challenging landscape of corporate America fresh out of college while raising my young daughter, Madelyn, struggles sometimes were an everyday experience. Read more>>

William Yeats Ihrig

In my senior year of high school, I decided to move to Florence, Italy to study traditional oil painting at a small art school. I made this choice for a lot of reasons. Read more>>

Connor McGaffey

In 2014 I started a business in Detroit called “Detroit Dart Club” It started off with an idea in my house when I was hosting nerf battles. I thought this could be a good idea. Read more>>

Eboni Huggins

Starting Uncouth was a big risk in itself. I’m a single mother of three Dragons (…or children, whichever you prefer), so deciding to invest my own money into a niche business was something I really had to pine over. Read more>>

Michele Rae

This is the first time I have written about this vulnerable experience. It has strengthened me and touched me deeply. Read on with a tender heart. Read more>>

Roni Kim

Snack Break Studio was created based on the idea that our best work is done together. We were both running our own separate businesses and always dreamed of working together. Read more>>

Nicole Hanson

In 2022, my husband and I decided it was time to take a risk. After years of working within our respective degrees, we decided to take a summer off work and pour into our passions and see if, just possibly, we could turn them into our jobs. Read more>>

Meryl Evans

I’ve been self-employed since 2005. Around 2018, a client had been encouraging me to make videos. While I’m a marketing professional who knows the value of videos, I was realistic. Read more>>

Justin James Farley

When I was in grade school it became very clear to me that a profession in acting was the route I was going to take, regardless of how risky it was . Read more>>

Alexia Dugger-Maye

I feel that if you’re an entrepreneur you immediately know that you will be taking a lot of risks. Or you should know that in order to truly be successful there will be risks taken. Read more>>

MICHELE MITCHELL

R-I-S-K – it’s what my entire sports and professional life has encompassed. My youth was spent in the gymnastics gym and on the diving boards and platforms. Read more>>

Josh Forshey

Leaving my mentor’s shop to start my own was the biggest risk I took. It was calculated though. I spent months asking clients how they found me and once the overwhelming answer was instagram/word of mouth and not the shop I was working at, I knew I could make it on my own. Read more>>

Charlotte Piper

I’m reminded of an Anaïs Nin, “And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.” Read more>>

Crystal Puim

The biggest risk I ever took was to quit all other revenue streams and JUST focus on being self employed. That’s a hard leap to take- especially because if you are like me in nature you grew up being risk adverse and always being “responsible.” Read more>>

Cody Beebe

Early in life, I did everything by the book and as a result, I ended up with a full-ride scholarship to a university, headed down the path to become a civil engineer. It was a safe choice. Read more>>

Justin Chart

Captivating. Intriguing. Evocative. Just a few of the words that describe the experience of listening to Universal Music Group artist Justin Chart. Read more>>

Ruth Kaufman

Despite wanting to be an actor since Kindergarten and a writer before the age of 12, I wasn’t confident enough in my abilities or the chances of financial security to choose them as careers. Read more>>

Jen Graziano

I have a sign in my bedroom that I’ve had for a very long time. It says “leap, and the net will appear”. It reminds me to take chances, take risks, and go after my dreams. As we all know, it’s easier said than done. Read more>>

K.Janea’ Daniel

Leaving a secure, full-time job as a merchant mariner to pursue my passion as a full-time content creator was a defining moment in my life. Read more>>

Harold D Smith Jr

About 15 years ago, I had started on an Ed.D degree in Educational Technology. I took the first class and earned an A but it took a lot of time to complete all the reading, research, and writing. Read more>>

Andrew L. Barker III

The biggest risk I’ve ever taken was betting on myself and my talents and my outer-worldly creativity , learning to hone in on that talent and alchemize it into mastered skills. Read more>>

Benjamin Greene

For years, I planned to be an elementary school teacher. I spent my young years volunteering in classrooms and began college as part of an elementary education certification track. Read more>>

Katisha Shaw

Taking risks has been a defining aspect of my journey, especially as a woman entering the acting profession in my 30s. Read more>>

Kristin Yates Coleman

2 years ago I was an owner of an Ob/Gyn private practice. I had the dream job, 3 young kids, happy marriage and I was silently hoping to get in a car accident every day on my way to work. Read more>>

Stephen Mann

Coming from Savannah Georgia (a place where most people don’t leave) and being an independent artist is a huge battle. Read more>>

Alonda Green

At the tail end of 2020, I decided to pack up my things, leaving behind only what could fit in my car, sent my youngest son off to be with his dad for about a week and drove with my oldest son and our dog, to San Tan Valley, AZ. Read more>>

Julio Silva

Absolutely, I’d be happy to share. One particular risk that stands out in my mind was when I decided to leave the comfort and stability of a corporate design job to pursue freelancing full-time. Read more>>

Hillary Broder

I took a risk when deciding to pursue a career as an art educator. Attending more schooling was never in my long-term plan. I had always known I was going to be an artist and go into the art field for my career, but I did not intend to move towards teaching art. Read more>>

Leyan Senay

Firstly I want to thank you all for sharing the memories of my journey, so happy to be here! 💙 Risk taking and having a courage to leave your ‘safe zone’ is the key of success I think… Read more>>

Paige Berry

Moving to Austin, Texas in 2015 after 25 years in my hometown of Knoxville, TN was perhaps the biggest risk I’ve taken. Read more>>

Kandiee Campbell

I took the risk of having a nationally syndicated radio show called “Awaken Hope” on Brushwood Media Network. I decided to do it even though I had no clue as to how to host a radio show or what I was doing. Read more>>

Robert Szertics

One of the bigger risks I’ve taken is to leave my home country Sweden for the U.S.. I moved to Los Angeles in 2012 to study interior design. After graduating I had a hard time finding a job within my field of work. Read more>>

Miranda Underwood

The biggest risk I have ever taken in my life is betting on myself. Launching Cloud Nine Bartending, LLC wasn’t just about starting a business; Read more>>

Jaimee Makes

After teaching elementary art full time for 6 years, straight out of college, I decided to take the biggest risk yet. Read more>>

Shameca K Brown

The journey began after my third child’s birth, driven by a desire to offer them opportunities I hadn’t known. Read more>>

Alex Picard

All my life, I wanted to be two things. And actor, and a teacher. I loved being creative, but I also loved stability and health insurance… Read more>>