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.

Samuel Tolbert

This year marks six years since I left my job, and if I can be honest, that decision was one of the toughest I’ve ever made. I didn’t fully grasp the consequences before making the leap to shift gears. Read more>>

Jody Sperling

I left my W-2 in 2021 to go full-time with my podcast and my writing. Over the previous 5 years, I’d had good fortune and a well-paying job, so leaving employment, I had savings to live on for about three years. Read more>>

Miles Doleac

I read a quote from Mike Nichols (director of THE GRADUATE) once where he said “the only safe thing is to take a chance. Play it safe and you’re dead.” Read more>>

Ivy Tsai

In 2022, I embarked on my freelance journey and simultaneously resigned from my full-time position as an illustrator. I took this risk because I believe I can reach a broader spectrum of clients across various industries and countries. Read more>>

Chawin Piriyagagul

Normally, I would rather play it safe when it comes to any decisions in my life. But when it comes to what I love, I would rather jump out of my comfort zone and strive for my dreams. Read more>>

Tony Carpenter

A risk I took was investing money into radio promotion it was a risk because I honestly could not afford it at the time and I had no idea how I would make the money money back that I had spent before my rent was due but I leaned on faith and God and I had a sold out show and made the money back and then some.. Read more>>

Chasely Matmanivong

I am a huge risk taker. Someone who acts and asks questions later, especially as a creative. Coming from a religious background, going to college at a private college, and constantly being told no I can’t create art how I want to create art; Read more>>

Aesha Tahir

Starting my own business has been the biggest risk I’ve taken in my life so far. I never thought I’d be an entrepreneur. But as fate would have it after working eight years as a software programmer in corporate, I decided to pursue my real passion of health promotion and exercise physiology. Read more>>

Phivi Spyridonos

I am originally from Cyprus, a Greek island in the Mediterranean Sea. In my homeland, the typical path for students diverges from the realm of Arts and Design, it is all about science, math, finance and law. Read more>>

Adrian Elmore jr

Risk we take them every day. We take them when we leave the house. We take them when we drive away. We take the everyday life operational risk every day you are alive. Read more>>

Shannon Merciel

I would say my career choice in itself is rather risky. I’m one of those people that really put all my eggs in one basket. Music performance is my first and only choice for a career. Read more>>

Christine Mighion

Over the course of 4 years I took my dream of building a thriving business as a jewelry artist from ground zero to being published in numerous fashion and lifestyle magazines all over the world and seeing my work in multiple jewelry boutiques. Read more>>

Eloïse Descleves

Life in France was comfortable. I had a secure job as a producer’s assistant, a great group of friends, and a comfortable routine. But the dream of creating impactful content for a global audience gnawed at me. Read more>>

Alma Telibecirevic

I see myself as someone who has always embraced risk. Art has been something that defined me since elementary school, especially growing up in Sarajevo during the war, where art became an even stronger medium for expression. Read more>>

Racquel Frisella

In 2021, after 13 years in the aesthetic industry, I launched my own practice Racquel Aesthetics in Chesterfield as well as hand selected and hired 16 of the most amazing women to build the practice with. Read more>>

John Kim

I was a Managing Director of a national law firm in Australia – I had excellent job security, status, prestige, money. I was 33 years old when I decided I would leave it all behind. Read more>>

Kari Ellis

I made a pivotal choice: to step away from corporate America and embark on a fresh path by establishing a Recruiting company in Fresno, CA named WayPoint Consulting Partners. Read more>>

Uncle Spaceman

As creators, as artists we take countless risks. We bet on ourselves when it feels like there’s no one in our corner, no cheerleaders dance for us, spelling our names out in songs driven by the perfectly timed kick drum while the esteemed conductor wands our victory song. Read more>>

Mia Tennell

In November 2022, I was just getting back on my feet financially after moving from Maryland to Portsmouth, VA. In this process of moving, I lost about 90% of my things (clothes, furniture, etc.). Read more>>

Dr. Courtney Harris

The biggest leap of faith and risk I’ve ever taken was leaving my full time job and turning my then side hustle into a full time job. Not only did I jump head first into being an entrepreneur, but I moved and opened my physical therapy practice in my home state. Read more>>

John Dale

The biggest and most recent risk I have taken is stepping out of the corporate world of architectural practice that has shaped my life for 25 + years and joining a small design-oriented firm where I need to be completely hands-on. Read more>>

Moremi Okoroh

When I hear people discuss the topic of taking a risk it always feels a bit cliche. Isn’t life innately risky? You see I’m the the type of person who loves the thrill of new experiences. Read more>>

Stacy Armand Patterson

Taking a risk into entrepreneurship. The decision to venture into entrepreneurship was not without its trepidations—stepping away from the security of a stable job in social work, facing the unknown with each passing day. Read more>>

Natasha Weems

Throughout my journey in the healthcare sector, especially as an African American woman in nursing, I’ve faced several challenges that tested my resilience and determination. Read more>>

Daniella Melillo

Moving away from my hometown was a major life change that evoked many emotions. I grew up in a small, rural town in Harnett County where I formed my greatest memories and closest bonds. Also, saddest memories there. Read more>>

Debbie Bean

After nearly a decade of carving out my niche in the global art scene, building relationships with over 200 stockists and thriving online, I felt the urge for a creative reboot last year. Read more>>

Jamie Platt

When I went started art school, I declared an illustration major. I always loved children’s books and I thought it would be a great way to make a living doing something I love. Read more>>

Christine Mandese

I began my career at Quinnipiac University, where I earned the first of ultimately three master’s degrees in Education. Subsequently, I dedicated twenty years to elementary education, serving as a teacher, reading specialist, and principal. Read more>>

Adam Corneal

I took a risk coming to Boston one time. I didn’t have places to stay for more than two weeks and I needed to stay for 2 months. I knew that I needed to come to Boston in order to set up my life after the pandemic and after being sick in bed for a couple of years. Read more>>

Emily Deadman

I have been an artist my whole life, but it wasn’t until I started doing nails in the summer of 2023 that I felt the agency to use that word to describe myself. Read more>>

Ember Berg

Starting my business was definitely a risk, but it was also something that wasn’t really an option for me. I’m the kind of person that can’t go back on my internal compass. Once I know I need to do something, I do it – I’ll get sick if I don’t – and so I’ve learned to trust the process of realizing a vision once you set your mind to it.  Read more>>

Ashlee DiSalvo

In 2022 I left a decades long teaching career to focus 100% of my time and efforts on my business The Clear Estate and healing the world one person at a time. Read more>>

Jacqueline Martinez

Making the decision to publish was a major risk, since I am a person who does not like to take chances with my finances, and paying for an editorial team was a large outlay of cash. Read more>>

Heather Friedman

Something had to change. My primary care practice was not sustaining itself– my net pay was far from enought for the year after all the overhead of business costs. Read more>>

Anita Nowak

My husband and I decided to work as digital nomads with our newborn (!) and spent 4 years on the road, living in DR, Thailand, Morocco, and Georgia. Read more>>

Pennylyn Woosley

I took a huge leap of faith when I was 27 and decided to pursue my passion as a floral designer. I opened my first brick and mortar florist with little money but a whole lot of hope!! Read more>>

Elissa Anderson

Many of us are familiar with the expression “No risk, no reward.” We often get stuck in our comfort zones and don’t make the changes required for us to have the growth and opportunities we desire. Read more>>

Stephanie Belsher

With a lifelong dedication to children and youth, including a lengthy stint in Japan, I returned to Early Childhood Education in Canada, only to find myself stifled financially, time-wise, and in terms of curriculum control. Read more>>

Jamie Peer

Making the decision to switch careers at the peak of my current career, as I was on the brink of promotion to Lieutenant Colonel in the US Army, was undoubtedly a risky move. Read more>>

Peewee Dread

Taking risks can be daunting as an owner, and it may cause many to resist starting in the first place. It didn’t stop me, but it did make me wonder. Read more>>

Stacy Crawford

In the last few years, I have taken quite a few risks. For one, I recently moved my Mom, who has dementia, from Florida to Minnesota. Read more>>

Kalenga Augustine Mulenga

It was a Sunday in October. That’s all that I can remember. I can’t remember the specific date, just that it was a Sunday in October 2020. Read more>>

Chelsea Portis

The biggest risk I took so far in my life was trying to juggle becoming a nurse and running a business at the same time. Ive always wanted to be a nurse my whole life. Read more>>

Nicole Fournié

Listen to one’s self along the way, as I explored more and sought more clarity about my career path, continues to be the biggest and proudest risk that I take… often. Read more>>