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.

Kim Kiel

Business owners take risks almost daily. We take risks showing up on social media or speaking on stages. We take risks signing big projects or clients. Read more>>

Bella Moore

The biggest risk i’ve ever taken was when I dropped everything to move to Los Angeles to pursue my dreams. I grew up in a small town, and was comfortable with living there, but i’ve never been the kind of person to stay in my comfort zone. Read more>>

EliAna Klemm

Taking a risk on anything in life is by far one of the hardest choices someone can make. In 2019 I wanted more for my children, a better life and more opportunities for them to grow and prosper. Read more>>

Alice Gebhart

I was a public school art teacher for many years, and although I enjoyed my work, I was not truly fulfilled. As an educator, I found little time to create my own work. Read more>>

Kassie Kennaugh

The most significant leap I’ve ever made was acquiring the agency I presently own. Growing up in the Midwest, we were an average family, living from paycheck to paycheck. Read more>>

Derrick Hamm

Risk is an inherent part of art and creativity. The best results I’ve personally gotten was leaving the familiar and taking a chance. Granted, the risks I take are never blind. Read more>>

Fred Carriedo

In a way, I feel like my entire life has been a series of big risks. Immigrating to the United States from Mexico as a child was a huge leap for my family. Read more>>

Cortni Agnew

Taking risks has always been integral to my journey. Ten years ago, my husband and I defied the odds by marrying after two decades of friendship, a decision that laid the foundation for our family. Read more>>

Melissa Avitia

The biggest risk I have taken through my journey as a photographer is quitting my full-time job that I had from 2015 – 2023. I was frozen by fear and anxious to leave the comfortable spot I had worked so hard for within the company. Read more>>

Ruchi Sanjay Hendre

Coming to the US in 2019, with no idea about the computer graphics and animation industries was I think the biggest risk that I took, I decided to follow my passion. Read more>>

Yazmin Raymond

I think that any business owner, but I can only speak on creatives, has to eventually jump out of the safety net of what they “should” be doing with their life and go all in on what they want in life. Read more>>

Laura Cassidy

The biggest risk I’ve ever taken in my career was walking away from a successful, 15-year career in a well-known cosmetics company to return to a full-time focus on building a career as an indie film producer. Read more>>

Bryce Owens

One of the biggest risk I have taken is becoming a music artist. Starting out, I did not have a lot of support and people did not see my vision. Read more>>

Diana Belle

In the beginning of 2016 I found out I was pregnant and took a risk to leave my stable job in aerospace to become a stay at home mom. Read more>> 

Amberly Kelley-Dotson

Like many other folks, the year 2020 changed everything for me. Just before the pandemic really hit and shut everything down, I had been informed that the program I was employed through had lost its funding from the state, and if I were to stay employed with the same company, I would be looking at a dramatic pay cut. Read more>>

Anetah Spencer

I took a really big risk starting my business because I decided a conventional job was not working for me and every day I would clock in and hate what I was doing and just wanna leave. Read more>>

Anne Herrera

I consider myself to be a “late bloomer” in life. When I was a child, I was afraid of many things, and when I entered adolescence, my fears got sprinkled with a little anger, drugs, and alcohol, transforming me into the life of the party and further stunting any personal growth I might have otherwise experienced. Read more>>

Alex Barnett

My whole life has been music since I was an early teen, but when the music industry fell silent in 2020, it signified more than just the end of gigs and performances—it marked a profound shift in my professional trajectory. Read more>>

Darshana Patel

I was standing in the ICU and it all looked too familiar. It may have even been the exact one I was in when I saw my mom dying over 20 years ago. Read more>>

Karen Balumbu-Bennett

One risk that I’ve taken recently, is allowing myself to be more vulnerable by openly sharing more about some of my difficult experiences. Read more>>

Anthony Lachus

In order to create one must take risks. To make something that was not there is a risk. Allowing others to look at or listen to what was made is to allow them to judge it, which is taking a risk. Read more>>

Xavier Lamberth

My whole art journey started with a instagram story. I never thought of being an artist, I truly drew for fun but that one instagram story showed me that maybe this is the space I belong in. Read more>>

Kori Price

I’ve always been proud of my ability to be a high-functioning plate spinner, able to keep my full-time product management job, art, photography side hustle, leader of an art collective, and more balanced and moving forward. Read more>>

Amy Grimes

Many years ago, I was in the car with my family when I said, “Someday I’m going to write and illustrate a children’s book.” My oldest daughter, who was about 12 at the time, piped up from the backseat and said, “You always say that, Mom.” Read more>>

Julia Silva

A risk I took during my entrepreneurial journey was when I messaged a chef on Instagram asking if he had any work opportunities for me. Read more>>

Amanda Pasciolla

I have always wanted to start a business. Since early college, I have been collecting notebooks of ideas. Call it a side hustle, a business, or a passion project, I thought about it frequently. Read more>>

Ashley Olmstead

Prior to my “Quail Store” life, I had a comfortable, successful career as a Corporate Retail Merchandiser that took 23 years to build. Read more>>

Tara Masimer

Taking risks- Showing up every day is taking risk. Being an artist is taking risk. I do not have the ideal dancer body type. I am not sure what that means these days. Read more>>

David Shaft

A risk I took recently is going to the American Beauty Show in Chicago as press. I went in order to meet more business owners and learn about a industry I was unfamiliar with so that I could share that information with my podcast listeners. Read more>>

Melissa Yi

I wanted to write since I was six years old. But my parents wanted me to play it safe. I could become an engineer like my dad. A doctor was okay too. Read more>>

Stan Kurth

For a number of years, I struggled with style. Some of my paintings were good, but the body of work I created was not unified. Read more>>

Ken Neiheisel

I think of many risks I have taken as it relates to my artwork. Starting with making a decision to leave a full time career as a owner of a strategic design agency and pursuing a dream to spend my creative energy as a fine art painter. Read more>>

Daniel Toney-Leclair

As an artist I have learned you have to be fearless. I used to rely on my intelligence, on what was known. Over the years I have realized that some of my best work has come from me taking risk and following my intuition. Read more>>

Martin Encinas

The biggest risk I’ve taken was undoubtedly opening my own gym and fitness facility. It’s been a journey filled with challenges, setbacks, and moments of doubt. Read more>>

Dianne Smith

When thinking about making work or a project, I figure out what I want to say and then find the best medium to say it in. Similarly, when putting up a site-specific installation, I am still determining what it will be once it’s done. Read more>>

Jenny Dicola

I have recently wrote this for a blog post but haven’t published it yet so I wanted to share this. Finding the sweet spot in your business One of my favorite places to eat is Five Guys. Read more>>

Carly Hughes

Back in 2023, I was working full-time as a marketing manager for a women’s e-commerce clothing brand. I really liked my team and what the brand stood for, but the job was unreasonably demanding, the pay wasn’t great, and there wasn’t much room for me to grow since it was a small company. Read more>>

Jess Olson

Taking risks is an integral part of owning a business and being an artist. When I was first starting out as a 20- something fresh out of college, I remember my Dad saying to me, “Now is your time to try things, to make mistakes, to figure it out. Take some risks.” Read more>>

Gabriela Gonzalez Dellosso

As an artist one of the things I am always faced with as I progressin my artistic journey is evolving and always growing. Taking the familiar and safe road is always inviting. Read more>>

Courtney Shihabuddin

Choosing to publicly share my journey with breast cancer was one of the most daunting decisions I’ve ever faced. I was diagnosed in February 2020 with stage 1b invasive lobular carcinoma, Read more>>