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.

Shery Zimmermann

I’d love to talk about my first time selling products in person for Crickside Yarbs, but first I need to set the stage. It was 2022, and I had studied herbs and home remedies for over a decade as a hobby and to support my family and friends. Read more>>

Cheri Shandra

At the center of life is the option of risk-taking, something I value these days but avoided for many years because the comfort of what I knew had a far greater impact on my decision-making than the fear of the unknown. Read more>>

Gisela Cantres-Toro

When I was a junior in high school I already had an idea that I wanted to pursue a career in the film industry. Coming from a military family that wasn’t sitting well with my mother. Read more>>

Mary Dibble

Making the decision to become an entrepreneur while working a full time job from home while having 2 toddlers at home and a teenager in school was quite the risky move. Read more>>

Brandy Walker

I have a high risk tolerance, and so I have taken some risks that have panned out well and some that I cringe to think about in hindsight. Read more>>

Martha Terris

I am Chair of a Urology Department in Augusta Georgia. Urology is a field that has historically attracted few women and people of color. Read more>>

Sara Leggett

Hiking over 50 miles in three days taught me that I can do more than I think I can. Even when times get tough. Not only do I hike and run my own photography business, I am a director of special education and a doctoral student. Read more>>

Charisse Harris

I will always remember back when I decided to be an artist as an undergrad. Most people were nervous, worried, and flat out advised against it. Read more>>

Kimberly A Cook

I have never identified myself as a risk-taker. Frankly, based on my fear of heights, scary movies, and self-identifying as “type A,” I am most comfortable knowing “what comes next” or, at least, having a good handle on the anticipated outcome. Read more>>

Tiffany Lai

Growing up I was the quiet art kid that kept her head down and got my work done. I was terrified of life itself and something as simple as raising my hand in class or checking out at the store by myself felt like a huge risk. Read more>>

Tiffany Conway

The greatest risk I ever took was committing to a career as an artist. I made a plan to save up before leaping., but in 2020, God made the leap for me with the pandemic. Read more>>

Evan Ringuette

I always enjoyed making erotic artwork but I would keep it separate from my other work. I guess the reason I did this is so I wouldn’t offend anyone. Read more>>

Sara Rogers

Taking risks is often the spark that ignites our greatest adventures. For me, that leap of faith came when I made the bold decision to move to South Florida, alone, just two days before my 25th birthday. Read more>>

Michelle / Gabriel Moseley / Frady

I, Michelle, am a true introvert and thrive on time alone. Choosing to share the mission of SimplyNCgoods – to support NC-based small businesses and bring some of the best of North Carolina made products directly to folks’ door via quarterly subscription boxes – always feels like a risk to this introverted soul of mine. Read more>>

F. Scott Hess

I grew up in a small town in Wisconsin. Nearing the end of high school, I was advised by counselors, teachers, and even my parents, not to go into art but to choose something I could make a living at. Do art as a hobby, they said. Read more>>

QueenAfi Gasto

In 2008, I willingly assumed a substantial risk by intentionally adding domestic violence and mental health to critically important dinner table conversations. Read more>>

Lendryx Barnes

Joining the military nearly 12 years ago allowed me to leave my low class home in Alabama. Outside of the obvious risks of putting your life on the life for your country, I also ran the risk of my career dreams of being an artist being delayed. Read more>>

Connor O’Brien

The biggest risk I ever took was for myself and my dreams. I am from a small town in Indiana and grew up knowing everyone in town. Read more>>

Dee Von Kauffmann

Moving to America I’m 35, single, living in Sydney Australia it’s 2021 It’s covid and Australia’s lock downs were very strict. Couldn’t leave 5km from my house. Read more>>

Adnan Nasser

I decided to return to Lebanon for work purposes. It was a risk, but a calculated one for sure. My intention was to come back and practice journalism with the expectation I would find likeminded people with the same goals. Read more>>

Patrick Furlow

One of the biggest risks I’ve ever taken is putting all our eggs in one basket…quitting my corporate job and joining my wife Anne Furlow in her home staging business, Step by Stage Interiors. Read more>>

Daniel Walters

Pivoting from human to veterinary healthcare was a big risk- Would I be accepted in the veterinary world? Could I land a full-time job? Would my clinical skills be enough to be successful? Read more>>

Kimberly Johnson

In 2020, I decided that the career path I had been taking for 4 year prior was not making me happy. I would wake up in the morning, dreading to go to the office. Read more>>

Morgan Hunter

I bet on myself and my team – with the mindset “If I never quit, I can’t fail.” After just a few years in business, with most of them spent during the waves of the pandemic, we leased 2 buildings for our bakery to grow into. Read more>>

Sergio Ortiz

The music industry is probably one of the most difficult fields to be in. After retiring from the U.S. Navy, I knew I didn’t want to go back to working for anyone ever again. Read more>>

Cheval Drake-Oladoyin

Once lost in the fog of postpartum depression, unsure of where life was headed, I decided to take a leap of faith. With a glimmer of hope and trust in God’s plan, I ventured into the unknown and started my own med spa. Read more>>

Kalyn The Miller

Milling flour was never on my [extensive] list of goals or skills that I sought to learn. I was a feral lady, living off grid in the woods and on farms for 15 years of my life. Read more>>

Karen Leming

As a young woman, I started a career in Emergency Services because I wanted to help people in an exciting badass-job. I loved driving the big trucks, swinging the “irons,” and blasting down fires with the hose. Read more>>

Désirée Worrall-Bélanger

Taking a risk is the best thing I’ve ever done. I’d always wanted to start my own business, but I knew there were so many risks that came with it, so I pushed it off year after year. Read more>>

Nickey Boyd

Starting my culinary journey at 30 was a huge risk for me. Before attending culinary school I struggled with what I wanted to do as a career. Read more>>

Andrea Doyley

Hey everyone, so before I’ve started taking my talents seriously I was in college majoring in medical assistant and starting a job in my career path, taking a class at the job to become a CNA and a GNA. Read more>>

Meghann Birks

As a neurodivergent woman with ADHD, I’ve always been more comfortable with risk than most, with varied results. My impulsivity means that I’ve travelled a lot, owned several businesses, had some really wild adventures and trusted my gut when I met my now partner, agreeing to move to Australia after knowing him for only a few days. Read more>>

Brianna Neal

After graduating college in 2017 from the Fashion Program at The Illinois Institute of Art – Chicago, I created my brand B.LaShae Designs. Read more>>

Marielena Martinez

Well my entire process into this business has been a risk. I always had an idea and followed with my gut . I like to say that this industry found me I didn’t find it. Read more>>