The chapters in our stories are often marked by wins and losses. Getting a new job, getting fired. Getting a life-threatening medical diagnosis, beating it and getting a clean bill of health. Too often, due to a societal expectation of modesty and humility we are discouraged from talking about the risks we’ve taken that led to those ups and downs – because often those risks draw attention to how we are responsible for the outcomes – positive or negative. But those risks matter. Those stories matter. We asked some brilliant entrepreneurs, artists, creatives, and leaders to tell us those stories – the stories of the risks they’ve taken, and we’ve shared them with you below.

Marla Tseng

In my last few years in the corporate world, I lived a double life. In my public life, I was a lawyer with a well-paying job who advised my clients on complex trade regulations. But, in my private life, I was a practicing astrologer! Read more>>

Darius Johnson

My life is nothing short of risks at every turn, but it’s never once felt daunting because I have alway believed in my choices. I moved to Washington DC with my partner after we finished grad school. Read more>>

Brandy Johnson

After 10 years in a career that no longer fulfilled me I decided to take my BIG JUMP in 2017. This was a decision I went back and forth in my head about for the last 5 years. Read more>>

Liz Zuluaga

Starting a new venture is always scary and involves some risk and most likely some money so deciding to go for it is a big deal! For years we both yearned to start a podcast, but it was never the “right time” for so many reasons. Read more>>

Dani Kannapell

The most exciting and rewarding risk of my life was starting the nonprofit Impact100 Louisville at the age of 78. I heard about the organization in Florida six years ago and wanted to know more about it. Read more>>

Mary Holmstrom

Before starting my Life Course Correction’s Coaching Practice, I was a 20+ year veteran as a corporate nine-to-fiver and professional SAG/AFTRA actor. Read more>>

Cynthia Pace

I’ve always had this passion to create. Whether that was in crafts or in graphic design class in college, or even in my personal life. Read more>>

Kiki Matoba

Following our intuition usually entails taking risks. Intuition is a feeling and inner knowing that leads us towards unfamiliar territory but is ultimately for our highest good. Read more>>

Fabrizio Sclocco

My name is Fabrizio Sclocco and I am a contemporary figurative artist and set designer based in Toronto. I was born in Pescara, Abruzzo in 1989. Read more>>

Marley Washington

The biggest risk I’ve taken is merely just betting on myself. Being a freshmen in college & wanting to start my own business I knew i had to execute something I’ve never done before. Read more>>

Jen Clayton

A Journey of Self-Discovery: From Nurse Practitioner to Aesthetic Entrepreneur As I stand amidst the serene ambiance of my clinic, surrounded by the gentle hum of medical equipment and the subtle scent of essential oils, I can’t help but reflect on the journey that brought me here. Read more>>

Siriji Lamenzo

I began my Personal Training career in 2009 and right away I had imaginations of having my own space and my own business. I’ve never been good at working for others, so Personal Training suited me great. Read more>>

Kiara Ruth

I took a leap of faith last year and made the bold decision to leave my office job in pursuit of my personal and writing aspirations. While my job was fine, I realized it no longer aligned with my desires. Read more>>

Melanie Emlyn

Since birth, our parents strive to keep us safe, constantly cautioning us with phrases like “don’t do that,” “that’s dangerous, stop,” and “you can’t.” Read more>>

Ai Toyoshima

I believe an attitude of willing to take a risk is very important as an artist/creative because without doing it, you will go nowhere. The result of it might not be something you expected, but there is always something valuable left. Read more>>

Gica Pucca

Once the COVID-19 pandemic subsided, I made the bold decision to catch the first plane to Los Angeles to pursue another education in Performing Arts. Read more>>

Richard Rodriguez

I was living my life where everything was the same, everything was safe, everything was easy and most importantly I wasn’t failing. I was working as an Architect for multi-million dollar custom homes. Read more>>

Jessica Bergin

My undergraduate degree is in Athletic Training. With AT being a bachelor’s degree at the time, and collegiate and professional athletics requiring a masters degree to work, it was common practice to get a job right out of school as an intern or graduate assistant while pursuing your second degree. Read more>>

Princess Walker

For much of my life, I wandered, searching for belonging in places and faces that never quite felt like home. Lost in a maze of uncertainty, I chased shadows and echoes, always moving but never truly finding my way. Read more>>

Jessica Werner

In late 2016, my husband passed away suddenly leaving me and my three-year-old daughter. I knew immediately that I had to leave my home state of Missouri. Our goal was to move to Oregon after honeymooning here in 2012. Read more>>

Zion Jones

Prior to my first vending event, I was extremely nervous. I didn’t think I would make a lot of money and furthermore, I didn’t think anyone would care about my art. Read more>>

Mariah Pinckney

I was given the advice that you can’t run from your purpose. Either you face it and figure out how it fits into your life, or it will haunt you. Read more>>

Julia Van Valkenburg

Getting into real estate and the path that lead me here has been a series of risk taking. Some “leaps of faith” were softened by a safety net or my supportive husband, but many times it felt like there was no railing to prop me up if I fell. Read more>>

Alyson Haines

Quitting my corporate job without having another corporate job lined up is probably one of the bigger risks I’ve taken but also one of the most aligned risks and necessary risks. To put this into context, let’s go back to 2020. Read more>>

Gregg DaCosta

I would say my whole career is taking a risk. When it comes to the film industry you’re always taking a gamble because you don’t know whether you created a hit or you missed. Read more>>

Danyell Johnson

I was fresh off a plane from Atlanta Ga to Los Angeles California after abandonment by my new born child’s biological father. I had no money, no job, and no car. Read more>>

Clemesha Pruitt

Taking a risk is something that heightens your anxiety due to the unexpected. I recently took a risk just a few short months ago and quit my government job. Read more>>

Emily Otto

I took a big risk when I finally quit my 15 year corporate career in human resources and recruiting and started my own business. I wasn’t sure it would work, if I could do it, if people would be interested or even in WHAT I was going to do for my business! Read more>>

Chenwei Xu

Risk-taking is an essential part of personal growth. One of the biggest risks I’ve undertaken was relocating from my home country shortly after college to pursue graduate school and career opportunities in the States as an international student. Read more>>

Gary A Wales

In 2022, while in Canada, I sought help from Now Hair Time in Istanbul, Turkey, as I was unhappy with my receding hairline. Wanting to boost my confidence and improve my image, I took the chance and underwent surgery with them in 2023. Read more>>

Allison McFarlane

Leaving my stable career in commercial banking after 15 years was daunting, especially as a single mother supporting my daughter, Samirah. Read more>>

Tanner Bosma

In 2021 I had just completed my first year of teaching, and I was coaching diving at my alma mater high school. Things were great and comfortable! Why would I want to change that? Read more>>