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.

Dominick Martinez

I have taken many risks in my lifetime, the first time I took a big risk was in the name of passion for my art. I was just 18 years of age when I drove to a city two hours away from where I was based at (Tucson, AZ (my home town)), with no drivers license. Read more>>

Cheyanna Swisher

Photography has always been an enjoying hobby and release for me, but I never thought of taking it more seriously until I met the love of my life and he encouraged me to do more. Read more>>

Fernando de la Espriella

The biggest risk I think I have taken was kind of forced on me. I worked in public service for most of my adult life. First in EMS and later as a law enforcement officer. Read more>>

Sabrina Fedel

Putting words to paper, and then showing those words to other people, is inherently risky. Most people think that professional writers lay our words on the page and those words become immovable, the way decorative tiles are set into adhesive and grouted. Read more>>

Ron MacLean

Early in my short-story writing career, a story of mine won a big prize and was published in a glossy national magazine to much acclaim. Read more>>

Kennedy Williams

As summer began to turn into fall last year, I knew I wasn’t happy with my life. I had to make a change. I had been living in Atlanta for about a year at the time. Read more>>

Elijah Eugenio

The pandemic was a confusing time for most people, and my story was no exception. Freshly graduated from high school and entering adulthood through college for a nursing degree, I was anxious about life and unhappy with the uncertainty the future held. Read more>>

Erica Nunez

Taking a risk is comparable to jumping through fire—it’s essential for growth, building resilience, and deepening self-trust. This is something I wish I could tell my 23-year-old self who after college, moved to Atlanta with a negative balance in my bank account. Read more>>

Linsay Alcindor

One of the biggest risks I’ve taken was starting my entrepreneurial journey while healing from depression and anxiety. It has been an extremely challenging path, but I am glad I went through these trials and tribulations. Read more>>

Kelly Kumler

Before starting my business in brand and website design, I was an elementary school teacher of 7 years. I loved teaching and working with the kids, but always felt this tug to do something else. Read more>>

Olivia Dawson

Risk. Choosing a life in the arts is a risk.  It can be challenging, at times difficult and fraught with anxiety.  I have walked away from being an actor many, many times but always there was a sign from the universe that would say, “No, this is your path. Get back on it and don’t give up”. Read more>>

Skylar Lin

Taking risks has been a significant aspect of my personal and professional journey, and one of the biggest leaps I took was deciding to uproot and move to Los Angeles. Read more>>

Meladee Carter

Leaving my home in Barbados to attend the illustrious Oakwood University in Huntsville, AL in 2021, was quite possibly one of the biggest risks I have undertaken. Read more>>

Jim R. Moore

When I walk out the front door of my house every day I am taking a risk! Why shouldn’t we take risk in our art? WE SHOULD otherwise nothing will change in your life. Read more>>

Kylen Tennies

We have been best friends since we were babies and have wanted to start a business since at least middle school. We are both artists, creatives in our own way, and honestly life just looked so different than we expected almost ten years after college. Read more>>

Renee Brown

I did all the things I was told to—got a college degree and started working. There’s really nothing wrong with all of this. I worked in advertising and public relations. I met tons of cool and interesting people and learned many important skills. Read more>>

Olivia Tang

The biggest risk I’ve taken in my life so far was leaving my career in fashion to become a full-time stay-at-home mom. Back in 2017, I had just graduated from college and was offered a job as an Assistant Designer for a big fashion company in San Francisco. Read more>>

Brittany Williams Leverett

I’ve always been a busybody. I knew that I always wanted to be a business owner but had no idea how I was going to do it. In 2017 my Aunt Claudia started working in NC at her new quick service restaurant in the Concord Regional Airport. Read more>>

Morgan McEwen

A significant risk I’ve taken in my career was the decision to relocate MorDance from New York City to Yonkers after ten successful years in Manhattan. Read more>>

Tiffany Tanasse

Opening a storefront at 57 years old felt like taking a huge risk. This isn’t my first career, or my first business, and I’m beyond midlife in age. Read more>>

Abigail Melton

I would have never described myself as a person who took risks, at least not ones where I wasn’t fairly certain of the outcome which, ironically, makes it not very risky. Read more>>

Jessica Williams

Sometimes I think of myself as an “accidental entrepreneur.” I started my third business in 2017 (after two previous business failures, leading to many years in Corporate America). After getting laid off from my job in tech consulting, I didn’t have much luck finding a “regular job,” so I started looking at contract work. Read more>> 

Melissa Lombardo

Taking the risk of speaking out about difficult topics has supported my continued healing and thriving post trauma. I was sexually assaulted as a college student at the age of 21. After months of silence, I decided to tell a trusted friend who helped me find the supports I needed to begin my healing process. Read more>>

Brizzy Rose and Emma

One of the biggest risks we’ve ever taken was committing to Wedding Photography full time during a global pandemic. We had the tools and resources as creative people but we knew nothing about owning and operating a business. Read more>>

Michelle Von Ruden

I was unhappy with the job I was at. My boss was a Level 1 leader, meaning a leader by title only, yet they were at the top of the organization. For someone like me, who studied and practiced good leadership, this was difficult for me to say the least. Read more>>

Porsché Mysticque Steele

My life began just 5 years ago when I took the biggest risk of my life. I moved to Nigeria from California to see a man I’d never met in person. Read more>>

Joel Stevenson

I have been working as a sculptor for around 15 years. For about the last ten years I would occasionally sit down with a set of oil pastels and play. About a year ago I began in earnest to develop my 2D skills using the oil pastels to explore abstract art and allowing colors and ideas to flow. Read more>>

Melissa Zarb-Cousin

There are moments in your life that feel like a genuine crossroads. You know in your heart that a decision must be made that will affect the trajectory of your entire life. Read more>>

Carol Ann Kennedy

FIGHT FOR WHAT YOU LOVE My mother often said that I was the cause of the majority of grey hairs on her head. I believe this to be true. Growing up as the youngest of four sisters, I learned early on that life is meant to be lived boldly. Read more>>

Jerry Fabyanic

Writing books was never a life goal. It came about after I processed my way through one of my life’s greatest challenges. To come to terms with that experience, I began journaling. Read more>>

Alexandra Robinson

I started my bakery business almost nine years ago out of my home, in a 200-square-foot basement kitchen my dad and husband built. I grew my business there while having two of my three children. Read more>>

Linda Terrelonge

My entire life, I always wanted to be a communicator and create beautiful as well as meaningful things for people. When I was a child I was in dance and theatre. I also grew up watching the news with my grandparents so I was always imitating the reporters. Read more>> 

Garrett Brill

“There’s more to life than this,” a message whispered to me from within as I sat behind my desk in my enclosed glass office. I was sitting in the office of the healthcare company I had helped build from scratch over the previous four years. Read more>>

Alicia Sims

Risk is defined by Webster as the action of exposing someone or something valued to danger, harm or loss. It’s funny because after I shifted my primary financial stability platform to full time artistry, I realized I was actually taking more of a “risk” before the transition. Read more>>

Shamni Dougall

A little over a year ago, I hit a wall in my previous 9-5. There didn’t seem to be any growth opportunities, and I was no longer being challenged. The Organization’s structure seemed to be falling apart and the mission no longer seemed to be at the forefront of anyone’s decision-making. Read more>>

Brianne DiDino

For the last 21 years, I had myself convinced that I was destined to be a Medical Laboratory Scientist. It all made sense. As a young, observant and detail-oriented child, I always possessed a curiosity of why and how things worked. I have been a natural troubleshooter throughout life. Read more>>

Isaiah Volk

Recently, I have embarked on a journey I have always wanted to be a part of. For as long as I can remember, I have always wanted to be in a professional touring band. Read more>>

Aimee Alfaro

Starting up business is a big risk to take! Doesn’t matter what you do, just know there is no one like YOU doing it. That’s the difference and the reason I did took the risk. Read more>>

Barbara Gomes Serafino

I took the LSAT entrance exam on a whim and on the encouragement of a woman friend back in 1979. I had no mentor or idea even what law school was all about. Read more>>

Most Kudos

We’ve always put a lot of work into our compositions and recordings, and in an ever-changing world of fast pace social media we chose to remain resilient and patient with our craft. Read more>>

Bessie Besana

By degree, I am a Civil Engineer and that is a profession that I practiced for eight years in a professional setting before shifting to fashion. Read more>>

Nick Gaga

Ever since moving to NYC and to US – everything has been a risk: starting a new show, meeting a new friend, even trying to get into a serious relationship. Read more>>