You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken.

Cecilia Battaini

I think the biggest risk I took was going full time with my creative business. I had a regular job, but started freelancing in my free time. I already had in mind one day I would left my regular job, also because it really made me unhappy, but everyone was telling me it wasn’t the right thing to do. Read more>>

Karen Parker Moeller

Two Big Risks Two years after COVID destroyed our small graphic design agency, my husband and I pointed our car north and drove to the scenic tourist towns of northern Michigan. Read more>>

Dylan Golshan

Starting my own sports agency straight out of NYU’s sports business program was a bold move, laden with risks. The sports industry is highly competitive, and established agencies have strong networks. Read more>>

Rachelle Carrie

Taking a business risk can be both exciting and intimidating. Whether venturing into a new market, launching a unique product/service, or investing in a risky project requires a leap of faith. Read more>>

Kesha Carmichael

Where do I begin. Has a child I had three dreams of what I wanted to be when I grew up. One was a ballerina the second was a wedding planner the third was I wanted to be a florist, but I didn’t want to make flowers out of flowers. Read more>>

Mark Rose

After owning and managing my prior business, I took up BBQ competition as a new hobby in 2015. Not knowing that I was entering a pro circuit, I was out of sorts, and out of my league (back then). Read more>>

Devari Tolliver

Over a year ago a took a risk on myself with motivation from others and people who enjoyed and believed in the energy I was giving by creating my own cardio dance platform and establishing my business as Devotion to Health and Fitness LLC in 2022. Read more>>

Janene Borandi

Acupuncture is not my first career! I started out in information technology at the National Institutes of Health and after about a year in support of the Office of the Director, I went on to take a federal position with the Social Security administration.  Read more>>

Eugenio Wilman

I was on a normal 9-5 job, working for more than a decade, then a decide to jump on a new path having my own company and offering more services related to what I love to do! Read more>>

Soco Reynoso

I learned from a good high school buddy that the best thing you can do as an entrepreneur is to fail fast. You have to embrace that you have embarked upon a life of risk-taking. Read more>>

Saul Gomez

Stepping out of my comfort zone. I was about 19-20 at the time and was completely clueless of who I was and who I wanted to be. I had to find my passion. Read more>>

Sharon Terry

Because of a number of situations in my life, I have taken quite a few big risks. When I look at most of them, I feel that though they felt significant at the time, they really weren’t among the biggest risks I’ve taken. Read more>>

Allayah Green

Fresh out of college, I was bursting with excitement and a hunger for something more. Armed with a degree and a ton of big dreams, I just knew I wasn’t cut out for the usual office grind. Read more>>

Kim Barry

In my life, with small to big decisions, it’s been listening and following my gut. Decisions are always risky. This statement may sound less than profound than in practice, but I have seen how easily we can be conditioned and rewarded by doing the exact opposite. Read more>>

Jessica Lissette

In 2021, I embarked on a transformative journey that would change the course of my life forever. Feeling the weight of my past struggles and the need delve deep into nature and my Self, I made a bold decision to follow my intuition to leave behind the familiar and venture into the unknown. Read more>>

Emily Falcon

I have always been a very private person. I do not share details about my medical history with most people. After my second open-heart surgery at age 35, I decided it was time to take a risk and share my journey. Read more>>

Kim Beechner

Opening a business is always a risk – it’s something that requires tenacity, hustle & faith in oneself. When I first launched Embark Marketing, I was a senior in undergraduate school on the cusp of graduating. Read more>>

Amanda Doyle

I remember when someone I worked with in education policy left our organization to go out on her own and become a “coach.” I thought to myself, “It must be nice to follow your dream. But I’m going to stay here and do REAL work.” Read more>>

Sherry Cherie” Feng”

As an illustrator, creative, and artist, there is understandable fear knowing that there is a difference and potentially a large gap between things that people like to see, whether online or in-person, in any capacity, and things that people will actually *buy*. Read more>>

Leonardo Sandoval

I moved to NYC with $500 in my pocket saved from busking in Brazil, and having never been to the city. I just knew it was where I had to be to pursue tap dance as a career. Read more>>

Christina Horn

My initial encounters with music immersed me in a predominantly male-dominated world. Beginning in fourth grade, I found myself as the sole girl in the entire brass section. Read more>>

Erin Clancy

I think the biggest risk I’ve ever taken was starting Blue House Curio, my small business. I took this risk because I knew I wanted to create art and share it with the world but I didn’t know how. Read more>>

Samantha Whisnant

m originally from Oklahoma, smack dab in the middle of the US. I graduated from college with a degree in Biochemistry, with a plan to continue my education in a graduate program or medical school. Read more>>

Katie Valentine

When the pandemic hit, I was hit hard. As a DJ, my career of ten years was taken away in the blink of an eye. My self-worth and sense of identity were tethered to my DJ persona. Read more>>

Michelle Holling-Brooks

Probably the biggest risk I took since deciding to start my own business back in 2008, would be in summer of 2019, before the wheels came to a stop with the pandemic, I had been feeling a nudge in my meditations to switch from having my business, Read more>>

Zoee Xiao

Taking A Risk: My Story of Freeing Myself from Golden Handcuffs and Finding My SoulIn the summer of 2018, I got a promotion, to the next level of software engineer. Read more>>

Courtney Brame

The biggest risk I’ve taken was saying yes to an interview by a local magazine publication about my secret project of interviewing people living with herpes about their experiences. Read more>>

Matt Willey

At 46 years-old I reinvented my career by starting The Good of the Hive, a global art project based in my personal commitment to hand-paint 50,000 bees (and other pollinators) in murals and installations around the world. Read more>>

Steven Burkhart

As you can imagine there are many risks in starting a business and even more that you have to take as you progress down the entrepreneur journey. Read more>>

Robyn Schindler

Once upon a time, I , like so many others in my field were busy working and overworking at a Mental health Facility. I loved working in the mental health field but I was becoming disheartened by the amount of “extra work” required at these facilities which took away from my time with clients. Read more>>

Jess Cuffe

One of the biggest risks I’ve taken in my career was one that came from failure, more or less. I’d been given the chance to come and work on freelance character designs at Marvel Animation Studios. Read more>>

Stephanie Newcomb

I was working at the Athletic Club as a trainer and struggled with getting clients and wanted to be my own boss. So I had a vision. Read more>>

Audry LaCrone

In the fiber world, people tend to stay focused on their own business. I wanted a way to connect with other indie-yarn dyers and work on a collaborative project. Read more>>

Nikolai Gionti

I came into college with a plan to graduate with a degree in journalism, cover sports and write or do media, but somewhere around the end of my sophomore year that changed. Read more>>