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.

Michelle De la cruz

The biggest risk I’ve taken was quitting my job at Chick Fil A to become a full time artist. I wanted to pursue tattooing and my artistic hobbies full time. Read more>>

Lia Braswell

There was a time early in my career as a drummer when I was playing for a band that seemed to have what I had always dreamed of wanting to be a part of. Read more>>

Amanda Tallman

I remember falling to my knees as I received the news that my team leader from my deployment to Afghanistan, had died by suicide. Read more>>

Elle Fultz

Taking risks are a part of life. I feel I have taken many risks in my life but the biggest is continuing to believe in myself, pursue my goals and building the life I desire. Read more>>

Ogechi Harry

March 2020, as cities (including Chicago) slipped into ‘lockdown mode’ and the world started to realize that we were potentially in the midst of one of the deadliest plagues of our lifetime, I decided to leave my big law firm job. Read more>>

TaRese Blair

As a single parent of four children, leaving a constant paycheck from my corporate job to focus on building my business was a big risk. I provide luxury services, so maintaining clients can be difficult. Read more>>

Dave Wagner

Prior to starting my own business and artist portfolio, I graduated with a bachelor’s degree in computer information systems. While this was a very meaningful accomplishment for me, I later realized in my life that I had become creatively frustrated. Read more>>

Tiffany Lee Brown

It’s all risk: your work, your art, your life. The fact that you got out of bed this morning, if you were fortunate enough to do that. When you give birth to or help raise a child. Deciding to do something you love. Read more>>

Lia Dunlap

## The Hero’s Journey: A Leap of Faith Growing up in a large lower-middle-class family, I was told that success meant getting a degree, a good job, getting married, having kids, and waiting until retirement to pursue happiness. Read more>>

Jessica Greene

I have always wanted to be in the birth world. When I was younger I considered becoming a midwife. Over time life happened, I got married, had kids, and as with most families found myself feeling kind of stuck in the grind. Read more>>

Jeff Cason

I saw Fantasmic! at Disneyland when I was 8 years old, and in that moment, I knew I wanted to create nighttime spectaculars when I grew up. The only problem was, I had no idea how to follow that path. Read more>>

Emma Riley

At the age of 23, I made a bold decision to venture into the world of freelance digital marketing, stepping away from the security of full-time roles to pursue my entrepreneurial dreams. Read more>>

John Murry

The entire story of BiscuitTinRPG is one of risk. I never started out thinking i would make anything of real value, I was just creating things that made me smile and hoping it helped other people smile too. Read more>>

Cameron Warren

I’ve learned that sometimes you have to take a leap of faith to follow your passion. Read more>>

Karyna Perahudava

One of the biggest risks I’ve taken in my life was moving to the US. I had to drop everything in my country (Belarus) where I lived for 17 years and right after my high school graduation hop on a flight to a completely new life for me. Read more>>

Michelle power

Making the decision to transition from my private psychotherapy practice to founding Pawsitively 4 Pink was both challenging and transformative. Read more>>

Jessica Friednash

In life you are given 2 options. You can either take the risk or lose the chance. You can either conquer your dreams or regret not trying. Numerous times in my life I let other people dictate my success and value.  Read more>>

Dr. Vanessa G. Hall

Risks are the calculated chances we take in life that either advance our attempts or quickly teach us valuable lessons that may temporarily set us back but can also be a vessel to prepare us for our NEXT! Read more>>

Channy Cardenas

If you have followed my music career closely most know the reason I started to release music. The passing of my mother and realizing life is taken in the blink of an eye. Read more>>

Monique Haddad

Transitioning from completing my five years at Cal State University Northridge to embarking on a career as a certified personal trainer felt like a significant risk at the time. Read more>>

Chrys Phillips

One heat wave summer evening in Australia, I couldn’t sleep as the a/c was broken and I started to dream of a place I’d rather be, and that was a coastal town with cool sea breezes and the hidden secret that magic actually existed. Read more>>

Eddie Wiedmann

On June 1st, 2019 I resigned from being a Police Officer in Central Falls, Rhode Island. Up to that point I was a 24 year old kid living on his own with a bright future and the ability to retire at the age of 47 with a healthy pension. Read more>>

David Badal

I’ve always said every aspect of life has risk; every decision has different outcomes. But in both my personal life and career, I’ve never regretted any decision I’ve made. Regret is for those who fear failure more than they crave success. Read more>>

Alyssa Chavez

The biggest risk I took with my brand was my first fashion show. A handful of fashion show directors were contacting me asking if I wanted to be a designer for their events. Read more>>

Renay bossy Graham

The biggest risk that I’ve ever taken as a cosmetologist or as a business owner was definitely working with the national Cancer society/Texas oncology Bedford. Read more>>

Amber Bell

The risk I took starting my business was investing my last $200 to register my business. I never looked back I just leveled up. I prayed on it first then I was like you know what? I can’t lose the next week I doubled up. Read more>>

Michael Brovac

I’ve taken many risks in my life but the biggest risk I’ve ever taken was to commit to health and listen to my mentor the first time I met him 2018. Read more>>

Darrell Somers

In my life I have taken many risks, some I am amazed that I am still alive after taking them. I think the two risk that I am happy that I took was showing my art at several different venues. Read more>>

Ricky Bartlett

As a disabled (double-leg amputee) actor and radio host, taking risks has become a source of comfort. I lost my left-leg in 2014, due to Necrotizing Fasciitis, or commonly called ‘flesh-eating disease’ I obtained from a hiking trip to Wyoming/South Dakota. Read more>>

Krista Durant

One of the most significant risks I’ve taken in my life is tied to my 12-year journey with Crohn’s Disease. For over a decade, I found myself in and out of doctors’ offices and consulting with GI specialists, relying heavily on medications to manage the symptoms. Read more>>

Serena Strelow

Life is full of twists & turns; but God has always had me in the palm of his hand. When I started my small photography business a few years ago (August 2020), I didn’t know what would lie ahead of me. Read more>>

Eddie “Leo” Marshall iii

Taking a Risk started for me when I left my HomeTown Anchorage, Alaska; to pursue a career in the entertainment industry. This pursuit led me into many places geographically as well as, not your best of situations. Read more>>

Richard Cohen

My dream was to work for a top investment bank. I recognized that I couldn’t attain that type of position without an advanced degree, but my grades weren’t strong enough for me to be accepted into a top MBA program, which is the usual prerequisite for joining one of these firms. Read more>>

Linda Kaye-Moses

There are many tales of risks I’ve taken in my life as a studio jeweler, not the least of which was, when, as a single parent, I was invited by a friend, a goldsmith, to take a class with her, learning to make jewelry. Read more>>

Ericia Smith

On October 25th, 2023, I lost my full-time job. I was devastated, but in that moment, I realized that I didn’t want to work for another employer again. Read more>>