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.

Heather Berthelette

Some might say it’s a risk being an artist. But I’ve come to the conclusion that it’s an even bigger risk not being one. A few years ago, right before the start of the pandemic, I was a regularly employed office manager at a mental health office. Read more>>

Kim Plasencia

I was working full time for another small business owner driving back and forth from Fort Worth to Dallas everyday constantly feeling like I could be doing more with my time, effort, everything. Read more>>

Ariel Hosanny

I was born and raised in Toronto, and I have watched it become fast-paced and very business oriented. I had a very active and outdoorsy childhood and enjoyed art in school. Read more>>

Aneisha Brackens

A big risk I’ve taken was moving from Foley, AL to Los Angeles, CA one year post college. I think in our 20’s it’s such a challenging time trying to figure out who we are, what we want, how to get what we want, and just the little knacks in life. Read more>>

Donta Daniels

This past year has been a huge risk for me. July of 2023 I left my retail job to pursue my passion of wanting to own a clothing line. I had experience with getting some T-shirts printed from my local T-shirt printing place but I had no idea what it took to build a business from the ground up. Read more>>

Nelli Garibyan

My background is sales and marketing. I graduated with a degrees from Boise State University in marketing and my first job out of college was advertising sales. This position taught me a great deal about business. Read more>>

Bridger Swinimer

during the pandemic in 2020 at the age of 22 I quit my job as a carpet cleaner, packed a bag and moved into a van. I traveled the country leaving everyone and everything behind. Read more>>

Moni Light

The risk of following my dreams. My Junior year of University, I started singing in a band – the Kat Hall Band. It all began about 6 years ago when we discovered our voices meshed well when we sang spontaneously in California at a bonfire, while we both just happened to be visiting the area. Read more>>

J.G. MacLeod

As an author, I made the decision to take a risk with each project to force myself out of my comfort zone and develop new skills with my craft. My first book, Abalone, was semi-autobiographical. Read more>>

Elyse Meyers

Risk by definition means “to take a chance on”. I think most of of us were risk takers as children… you know, before logic and executive function fully kicked in. Read more>>

Hadassah Treu

Risk-taking is important and life-giving. I’ve always thought of myself as someone who is too cautious and avoids risks. In my teenage and youth years, Read more>>

Tanja Diamond

If you dream of being your boss and carving your path, you better be ready for some serious risks. I’ve been chasing visions and entrepreneurial dreams since I was sixteen.  Read more>>

Jill Jaracz

I love podcasts, and I also love the Olympics—so much so that I wanted to listen to a podcast about them year-round. Unfortunately for me, that product didn’t exist. Read more>>

Lauren Manicke

Does agreeing to this interview count? Of course, I’m 90% joking, but there’s still 5% fear and 5% disbelief that I am able to publicly share my experiences. Read more>>

Beth Hansen

My Studio moved from inside Doctor Who’s Tardis to a Victorian house in a small town. No, I was never one of the Doctor’s companions, it wasn’t that easy, although it did involve a good deal of travel. Read more>>

Sofia Masson

Moving to a new city fresh out of college with my life packed up in a truck and a dream in my heart, I had no idea what I was getting myself into. Read more>>

Kate Dunn-Flynn

My career path has been nothing short of vibrant! From teaching assistant and professor to special events coordinator, research interviewer and document controller at two large Canadian EPCM companies, my journey could be described as a giant kaleidoscope of diverse experiences, opportunities, and plenty of risks. Read more>>

Sherron Mosley

Around the age of 35 I was in trying to figure out what direction I wanted to go in career wise. I loved the job I had but I realized that I had reached my peak at my current position. Read more>>

Grit

Opening up a new business always involves some degree of risk. For a group of five 20-something artists, many of whom were enormously daunted by the world of number crunching and taxes, the decision to open up a teaching studio was especially intimidating. Read more>>

Bodhi Calagna

I had spent many years in the coaching and hypnotherapy field, achieving significant success with clients. Despite this, some individuals still struggled to make breakthroughs. Read more>>

Timothia Reid

My business partner and friend, Luberta Lytle, and I took a big risk last year when we started her television show. Neither knew what we were doing, and we were scared to death that it would fail. Read more>>

Alexzandra ‘Ally’ Strickland

Life is the sum of our decisions. Each equation will look and feel different. We have the choice of what equation we will work and work again. Read more>>

Ruth Nemzoff

My professional life has been a story of risks and taking advantage of any job or opportunity which came my way. By the time I was 65, I had taken plenty of risks, I found a job while pregnant at a time when it was socially unacceptable for a woman, let alone a pregnant woman, to hold many jobs. Read more>>

Samantha Paige Rosen

I’ve taken a lot of risks in my professional life—auditioning to be the lead singer of a wedding band when I was 15 (didn’t get it—no driver’s license); Read more>>

Angelina Duplisea

It’s kind of cliche but my entire career is a risk. Typically, people my age(51) and size (26/28)aren’t pulled for many projects, let alone the high profile ones that I’ve been blessed to work on. Read more>>

DyAnn Houston

I have always been an entrepreneur at heart. I became a licensed Realtor in 2001 and was full-time for six years until the housing market crisis in 2007 at which time I sought out temporary employment to keep my head afloat while riding out the housing crisis. Read more>>

Jacqueline Novy

In the spring of 2019 I decided to take a risk and submit myself for a musical theatre workshop at Stella Adler in New York City. At the time I was still a student at Berklee College of Music and while I was doing shows through their theater classes, Read more>>

Christopher Mancini

I had been making custom furniture and restoring vintage trailers for a few years with my brother-in-law Quinten, which we started after Covid hit, both of us leaving behind the service industry. Read more>>

Julie Hardy

Owning a business was never part of the plan. My background is in healthcare finance, and while it was stable, I was craving a balance between what I’m good at and what I’m passionate about. Read more>>

Maria Bata

Leaving everything behind on a journey to an unfamiliar place was daunting, but the pull of a dream was stronger than the comfort of the known. Read more>>

Kelly Henderson

Its February 2020, and we were informed immediately to shut down and walk off our tv production studio lot. We’d been paying attention to the covid outbreak whispers and tellings, and then in an instant it was serious enough for the show “not too go on.” Read more>>

Nancy Rivera Gomez

There have been many risks that I have taken in my life, but the most memorable one that changed my dance career was in 2021 when I was still waiting to hear if my visa would be approved or not. Read more>>

DeAndre Smith

The biggest risk I took in my career was literally just “Starting.” I had no clue on how to start my business, all I knew was that I wanted to become a private chef. Read more>>

Zack Flavin

So when we last spoke I believe I was just working on breaking my way into the industry, animation to be specific. At the time I had starry eyes at all the possibilities my career could bring me to. Read more>>

Colette Cosentino

On taking a risk: It is a risk in itself to throw oneself into the art of making art, and expecting to make a living from the craft. However, to be truly fulfilled, happy, and energized, a person MUST do what they were created for. Read more>>