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.

Jennifer Mahnke

(The answer to this question one flows nicely out of the second question where I introduce myself) As I consider my life and what I do, many little risks jump out at me that I think are really all connected. Read more>>

Jay Bales

I was born and raised in a small town in Indiana. Where dreams were frowned upon. It was a “waste of time” pipeline dream people said. Read more>>

Adam Lawrence

When I was freshly out of high-school, I procured a job working for my father at an Advertising Agency. I was an entry Production Artist. Read more>>

Keith Rivers

Most recently, my biggest risk was in 2018, leaving Seattle, where I grew up for 30 years, moving my wife and two girls, selling a production company, selling a house, and saying goodbye to a thriving community. Read more>>

Sandra Mayoral

Taking the risk of becoming a Real State Investor and a Business Owner is one of the the best decisions I have ever made in my Life. Read more>>

Gina Pamplona

My drive and determination to form a career doing ONLY what I love has been a long, windy road that I am still driving on. Read more>>

Abdul-Amir Williams

In life I feel as if there are many risks you have to take in order to reach different levels. My journey into photography is no different. Read more>>

Ben Szemerenyi

My entire life has been based around taking risks, ever since the very beginning. When I was seven years old, I moved from London to New York, a moment that set the foundation for the risks I’d take later in life. Read more>>

Imran Ahmed

Taking a leap into English rock music in Pakistan was undoubtedly a risky move, one that many would have deemed unconventional or even impractical. Read more>>

Katie Kramer

Taking risks can seriously affect the trajectory of your life, it’s exciting and scary all at the same time. In my experience, the biggest risks I have taken in my life, have positively affected it. Read more>>

Robert Hensley

For over twenty-five years, closer to thirty, I have worked in the entertainment industry. I’ve been a costume designer, a writer, a filmmaker, but my bread and butter was makeup. Read more>>

David Falter

My early career was rooted in multimedia digital design, specialising in aspects such as motion graphics, web development, 3D designs, and branding. Read more>>

Kevondra Harris

The journey from poverty to prosperity began with a single leap of faith. I’ve been working ever since I was sixteen years old. It’s a pretty funny story actually. Read more>>

Joey DiTullio

When I was 14, I stopped going to public schooling to focus on music full time as my life path. I knew from very early on that no matter where I was or what t I was doing, music and sound were going to be an integral part of it. Read more>>

Hugh Williams

I’ve had a few risk-taking moments during my career. All of these risk-taking decisions were from the gut and confident with no concerns about the outcome. And all outcomes had no negative consequences. Read more>>

Steph Hauser

In January 2019, I gave birth to our third son Zev at just 23 weeks gestation, just over halfway through pregnancy, under viability. Read more>>

Julian Frampton

Pursuing music full time is no easy task. It’s all or nothing and the reward is never promised. When the pandemic hit, I had spent the previous 5 years as a touring musician and was left contemplating where I was in life and what I really wanted to do next. Read more>>

Angelique Johnson

In this season of entrepreneurship, I host community spaces that support hundreds of people with healing and transformation, I create works of art that people are proud to display in their homes, and I have a profound spiritual practice that gives me a powerful foundation of clarity. Read more>>

Legend Franklin

When I was coming out of high school, I had plans to go to college. Initially it was for basketball, but I ended up getting a band scholarship on my instrument at Alabama A&M university. Read more>>

Amanda Gavarny

In October 2022, I came to another crossroads in my life. I left the relationship I was in, and my children and I moved across the country for a new adventure/experience. Read more>>

Kate Heartsong

Taking a Risk by Kate Heartsong I was working as a degreed accountant for 25 years, and at first enjoyed this work.  In the last 5 years of this career, there was an unsettled feeling inside me that I prefer to serve people directly, instead of the computer work and crunching numbers my work required. Read more>>

Jennifer Vollmann

When I was 22 and just out of college, I packed up and moved to Nairobi, Kenya. I had no job, no idea of what to do, and I knew just one amazing woman. Read more>>

Jimica Sayles

Taking risk always produce rewards! This is what I would tell anyone thinking about taking a risk great or small. I learned this very early in life and I’ve taken many risk some were great and some were not so much but I learned from them all. Read more>>

Abbey Moore

I feel as a business owner you take risks everyday. Some small, some big! But the biggest risk I took is what got me to where I’m at now! Read more>>

Luke McKinney

A risk you’re willing to take is an opportunity. I’ve been both privileged enough to receive opportunity and risky enough to take them. Read more>>

Peyton Womock

I’ve uncovered what I believe to be the key to thriving in the music industry! If you have ever watched Into the Spider-Verse then you might have heard this quote before. “It’s a leap of faith. Read more>>

Marina Valente

Absolutely, taking risks is an integral part of growth, not just in art but in life. However, my approach has always been to first grasp the broader picture — a sort of 15,000-foot view, if you will, before leaping into uncharted territories. Read more>>

Jessica Gee

Taking risks is something our family knows very well. Our journey began with wanting to do “a little bit of travel”, which ultimately led to selling our home and belongings, and embarking on our own personal ‘bucket list’ adventure. Read more>>

Astro

About a year ago I took a really big risk and decided to withdraw from college. College was something I always saw in my future and never imagined myself not completing. Read more>>

Tamara Fyke

I started a non-profit organization called Love In A Big World in 1996. Years later I took the intellectual property I created under that entity and repurposed it for a for-profit company. Read more>>

Chelsea Witt

As a young kid I dreamed of being a surgeon. My grandma called me Dr. Witt from the time I was 10 years old. I started shadowing surgeons who would let a kid come in, joined a magnet program in high school for future health professionals, and earned an EMT certificate before graduating high school. Read more>>

Simon Mansa

Taking risks has really been the catalyst for the most significant shifts in my life that I’ve experienced. There have been numerous times that I’ve had to pivot and rebuild from the ground up. Read more>>

Molly Harmon

Naturopathic Doctors are often referred to as the “unicorns” within the field of medicine. There are only 7 Naturopathic Medical Schools in North America making us a rare breed of doctor to begin with. Read more>>

Victoria Elder

Hi there! My name is Victoria Elder, and I’m from Orange County, CA. I discovered my love for film when I was a kid. I used to dress up and perform for my grandma when she was sick with leukemia. Read more>>

Nadine Johnson

My expertise as a PCH owner continued to develop over the years. My experiences in the field and conversations with families and prospective residents and other medical professionals opened my eyes to the fact that there was an increased need for personal care homes for our geriatric community. Read more>>

Samantha Tansey

Taking risk in life to pursue our passions or even to fail and realize what we do and do not want are definitely important. Without an element of risk in life we may leave this planet with regret. Read more>>

Sarah Leader

One of the most monumental risks I have taken is deciding to switch career paths from being a special education teacher to a real estate agent/house flipper! Read more>>

Xanthia Lace McCaul

In 2021, after spending a few years working with my family in my hometown of Potosi, Missouri, I felt the need for a creative outlet. Read more>>

Kat Donachie

When I left my hometown to come to New York City, I was a young dancer with aspirations of dancing in some of the best concert companies in the country. Read more>>

Jill Foote-Hutton

It feels as though we are in the age of spectrums, maybe the age of “iconic” spectrums. I only mean that we might be collectively over hearing these words, but risk-taking is only measured within the context of any given culture, right? Read more>>