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.

Irene Woo

This summer, I left my stable, six-figure software engineering job to pursue stand-up comedy full-time. If you had told younger me what I was about to do, I would have given myself a heart attack. Growing up, I thought my super power was being good at math. Both of my parents went to engineering school, so that felt like the natural path. Read more>>

Sarah Hope

One of the biggest risks I’ve ever taken was starting my private counselling practice. People often assume the risk was financial or logistical but the truth is, the real risk was internal. I was terrified of failing. Terrified that people wouldn’t take me seriously. Terrified that my lived experience, intuition, and insight wouldn’t matter as much as formal credentials. Read more>>

Hamid Ahmadi

In January of 2024, I was let go from my job out of nowhere. I still remember that day. My phone lit up nonstop. Nearly the whole office reached out asking what happened, if I was okay, trying to make sense of it with me. My favorite message came from my former Marketing Director. Read more>>

Miriam Rieck

In my early twenties, I decided I wanted an experience-driven life. I didn’t know then that I was a polymath(someone built for many creative lanes) or that my 3/5 Projector design and Gallup strengths were already shaping the way I moved through the world: curious, strategic, intuitive and unwilling to settle for a life that didn’t feel half-lived. Read more>>

Jacqueline Lara

As an entrepreneur and creative through and through, taking calculated risks is part of my DNA. When you operate this way for years, it’s easy to forget that not everyone moves through the world with the same instinct to leap, build, and iterate. Read more>>

Tiffany Nelson

When I was about 19 years old, I was working as an assistant for a director at a non-profit in New York City, and it was a miserable experience. My director was very difficult, and everyone knew it. One morning, I was suddenly let go—fired, as I saw it. It was devastating; I closed my office door and cried. Read more>>

Rachel Kalb

Stepping away from the corporate world wasn’t just a career shift for me — it was a soul-level initiation. I spent years in the tech and AI startup space, working my way into a secure executive role as Head of Operations. I had the salary, the benefits, the structure, the safety. Read more>>

Ruth Maldonado

I think the biggest risk that I’ve taken so far is starting my business! I didn’t know how it would pan out but I knew that I wanted to try to see if it would work out. Thankfully, my business has flourished and my private practice is thriving. Read more>>

Zi Zhuo

One of the most defining risks I’ve taken in my life came at a crossroads right after completing my undergraduate studies in architecture at Chongqing University. In China, it is common—and often encouraged—to choose stability: either pursue guaranteed graduate study at the same university or accept a secure position in a state-owned enterprise. I had both of those options in front of me. Read more>>

Amanda Akers

I quit my job. After being in a position that made me very unhappy for a year, I was sitting at dinner with a friend, something I didn’t often have the time to do, and I got pinged on our messaging app for something related to an upcoming event. I didn’t respond. Five minutes later, I get a text message, I didn’t respond. Read more>>

Clinton Gorham

I started designing way back in 2007, shortly after serving in the United States Marine Corps. I figured I’d do what everyone said was the “right” next step; go to college, get a good job, stay on a stable path. I picked up a part-time position at The School of Protocol, and that’s where I really started sharpening my creative skills. Read more>>

Ron Podmore

I was a young man attending college and soon to be graduating with my first degree; an Associate of Arts with a direct link to a regional university. Today, we might call that two-year degree a ‘Direct Transfer Agreement’ that allows students to transfer to a larger university as a third year/junior with declared major. Read more>>

Shane Meyer

I’ve been a tattoo artist for over 20 years. When my wife first got cancer, she had so many doctors appointments she couldn’t work anymore. Long story short, I opened my own shop so she could have something to be a part of to give her some self worth back. Read more>>

Peter Lee

Our Story Right before the pandemic began, my wife and I finally signed a lease for a restaurant. We had spent years looking for the perfect space, and when we found it, we both knew it was the one. We quit our chef jobs and were just about to meet with a contractor to begin the build-out. Then COVID hit. Read more>>

Marcie Youtz

One of the biggest—and scariest—risks I ever took was retiring early from the Ventura Unified School District at just 49 years old. For twenty years, driving a school bus provided me with stability, routine, and a steady paycheck. It was safe. Predictable. Secure. Read more>>

Mikayla Edgeworth Moody

As I reflect on my life, I realize that risk and I are good friends. I’ve always been someone who isn’t afraid to step out of my comfort zone. I embrace adventure, curiosity, and new experiences. One memorable moment that significantly shaped my journey was when I decided to move to Houston, Texas. Let me set the scene for you. Read more>>

Sheri Phillips

A big risk I took was when I was 36 and my husband and I decided to move our family — our three kids included — to Hanoi, Vietnam. I had just started building my network as a stylist, so the timing felt terrible. Read more>>

Meg Potter

In 2019, I had just moved to El Paso with my then-boyfriend (now husband) after he was stationed at Fort Bliss. I had a degree in communications and advertising, but like many twenty-somethings, I was still figuring out exactly where I wanted to fit in. I knew I wanted to work in marketing, so I started applying for social media management jobs. Read more>>

Carlotta Jay

Honoring my intuition regardless of what was presenting in the outer world has always led me to the edges of what is possible, or even probable, This is the risk I innately maintained throughout my life, beginning at the early age of 9 when I walked away from my family circumstances (a highly toxic and chaotic environment) that ultimately landed my only sibling into the mental health circuitry for the following 40 years, to never settling for less than what felt aligned and coherent throughout the gauntlet of life choices one must navigate..  Read more>>

Katrina Chavez

There was a moment a couple years ago where I realized I had reached a ceiling in my career. I was working in aesthetics, educating, training, leading, and on paper it looked great. But something in me kept whispering that I was meant to create something larger. A space where people could truly be developed, not just taught. Read more>>

Lindsay Fabes

Choosing between my marriage and my career was the biggest risk I ever took. During the pandemic, I, like so many artists, found myself unable to perform and had to take on work not in my chosen field. I was feeling a bit lost. I had felt like my career was on an upwards trajectory before 2020, and then everything shut down. Read more>>

Mahesh Sriram

“Taking a risk isn’t about being fearless — it’s about believing in something before the world sees it. My story began when I decided to step out of comfort zones — as an actor, a model, and later as an entrepreneur.” Read more>>

Jake Shannon

In October 2021, I wrote a $25,000 check I technically had no business writing.

At the time, I wasn’t broke, but I wasn’t sitting on a lazy pile of liquidity either. Lockdowns had decimated my main two businesses and source of income. I was married, three kids, multiple ventures, and like every entrepreneur who actually swings the bat, I had capital in motion. I’d already been through cancer as a kid, so I’m not impressed by fear — but I am very aware of risk. And this decision was pure risk: no guarantee of ROI, no safety net, no “we’ll see how it goes.” It was either going to accelerate everything or expose everything. Read more>>

Sunny Moza

Let’s set the context: Risk isn’t just losing everything—it’s the necessary surrender before transformation. A caterpillar doesn’t risk becoming a butterfly; it must dissolve to fly. Read more>>

Marilyn Lowey

After many years working as a theatrical Lighting Designer for International high profile projects, the entertainment business started to change due to budgetary restrictions. In most usual situations a lighting Designer was hired for a project and along with me came a programmer, and if budget permitted an assistant. Now, budgets were getting sliced and programmers and show electricians were getting hired to design lighting. Read more>>

Camille Wright

People always say “you should never quit a job without another lined up” and “it’s just work, just clock in and clock out.” But what about when your work environment turns toxic? What about when you wake up every day dreading work so bad that it physically makes you ill? What about when your work makes clear stances that fundamentally go against your values? It’s no longer “just a job.” It’s 40+ hours of our week, time we will, quite literally, NEVER get back. And I’m expected to just sit there and take it because “well just be grateful you have a job anyways.” Read more>>