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.

Gillian Crossland

Taking over Pitch-a-Friend in it self was a HUGE risk, but I made it even riskier when I changed the way the events were run, shaped, and how they looked almost fully after a year of being established in Denver. Read More>>

Ali Duffy

When starting my photography business, I was at a crossroads of figuring out what path I was going down in my career life. I have a bachelors of science in biology and I thought I’d be pursuing healthcare. After being wait listed for PA school, I worked in biological sciences for a few months on contract. Read More>>

Heather Nelson

One of the biggest risks I’ve taken didn’t happen all at once — it unfolded over time, and in many ways, it required trusting something I couldn’t fully see yet. For more than two decades, I built my career in hospitality, events, and business development. I understood operations, relationships, and how to make things run smoothly behind the scenes. Read More>>

Tanesha Cameron-Cole

I never considered myself a risk taker. I am generally cautious and optimistically calculated, but there have been a few monumental moments where I took a big risk. Read More>>

Brittany ( Britt) Crawford

Taking a risk used to mean jumping without a net. Now it means standing up at all. I was newly diagnosed with epilepsy while working full time — a job in education, a field that already asks for everything you have and then checks your pockets for more. I didn’t know how much I had left. Read More>>

Ariel Smith

The biggest risk that I have taken as a creative is showing up authentically. As a creative, you want your work to be perceived well. Instead of focusing on what I believe my audience would like to see, I started focusing on ideas that brought me joy. I have been creating content for years, but during this last year I have grown tremendously. Read More>>

Latoya Marsh

One of the biggest risks I’ve taken was choosing to stop playing it safe and fully lean back into my creativity, even when it meant stepping away from what looked good on paper. Creativity has always been a part of who I am. Growing up, I was constantly making things. Read More>>

Alyson Pratkelis

The risk didn’t start with a business plan. It started in a car at midnight, driving home from the Denver Eras Tour, iced coffee cups in the console, glitter still clinging to our clothes, and friendship bracelets stacked halfway up our arms. The night felt bigger than a concert. Read More>>

Jalen Ray

One of the biggest risk I’ve ever taken is moving to Atlanta. If it weren’t for me moving, I don’t believe I would’ve gained the courage to follow my dreams. I’m from a small town and my confidence was not where it is now. Read More>>

Alonso Navarro

I believe one of the biggest risk I have taken , was moving to the United states when I finished college in 2015. I was born and raised in Lima, and I went to college and study Hospitality management back in Peru. Even thought I love my country , I did not felt I was going to be given a lot of opportunities. Read More>>

Maria Giesbrecht

Two years ago, I quit my corporate accounting job. I decided to try poetic entrepreneurship full time (is that a thing?). It was a huge jump. Financially, yes. But mentally even more so. I had spent years doing work that looked stable from the outside and felt quietly wrong on the inside. Read More>>

Ken Collis

The Leap of Faith: Betting on Myself The biggest risk I ever took wasn’t a calculated investment or a corporate merger, it was the moment I decided to walk away from the security of a W2 paycheck. The Backstory: A Defiant Departure Fresh out of Cal State Northridge with my business degree, I was working a steady job. Read More>>

Alex Lilly

When I was 19, I made the hard choice to drop out of college after losing the passion that had originally led me to study Equine Science and Management. I didn’t know what I wanted to do next, only that staying in school wasn’t going to help me figure it out. Read More>>

Lydia Larson

When the pandemic hit in 2020, I felt an unexplainable urgency that ran deep inside my bones. It felt almost spiritual in nature and I knew I had to make a change in my life. I left my full time job and moved away from the busy city where I was living and went on a journey that only I could take. Read More>>

Jimmy Peterson

I’m a 35 year old male multi business owner and by far the biggest risk has been to bet on myself. Some would say that it’s wingsuit BASE jumping or one of the other extreme sports I do. I think as a society people give into social pressure. Read More>>

Tee Abraha

I once took a risk that, at the time, felt reckless—even irresponsible—but it ended up reshaping how I see myself, my career, and what I need to feel alive. At the time, my life looked perfect from the outside. I was living in London, working as a BDR while also managing marketing for a local restaurant near my home. Read More>>

Ayan Abdirizak

One of the biggest risks I’ve ever taken wasn’t financial, it was personal. It was choosing to start over, to rebuild my life, and to believe that I was still capable of achieving something great, even after years of putting everyone else first. Going back to school with my daughter was one of the scariest and most beautiful decisions I’ve ever made. Read More>>

Tim McAuliff, MD

My answer on this one was identical to, ‘Can you share a story from your journey that illustrates your resilience?’ So please use that question and answer (below) in place of this one. Thanks. Read More>>

DeCoide Brewer

One of the greatest risks I’ve taken was choosing the will of God over my own. For a long time, I made decisions based on what I felt was right or what I assumed would work for my life. But everything became clearer the moment I surrendered and chose to do it God’s way—even when I was afraid. Read More>>

Amy Freeze

After winning my way into the big leagues of competitive cooking, I was still no more than a home cook with some good ideas and a passion for feeding people. I’m not classically trained. I didn’t go to culinary school. My training has been completely hands on. Read More>>

Isiah Haji

I think this journey of mine as a whole has been the biggest risk I have taken since leaving home. Especially the decision to start from scratch. I gave my all to my music as an artist until the very end. Learning so much about the process and industry through my own experiences and learning from other’s. Read More>>

Kareece St George

Taking is risk is something we should all do as you only live once. Taking a risk is using money received to achieve a dream. I have always wanted to start a business as I love meeting people and assisting them any way I can. Read More>>

Kasey Acuff

Taking the risk for me meant choosing myself, even when it felt uncomfortable and uncertain. I didn’t step into my work because everything was perfectly aligned or guaranteed. I did it while balancing motherhood, family responsibilities, and a lot of internal doubt about whether I was “ready” or “enough.” There was a moment where I realized staying where I was felt riskier than trying. Read More>>

Heather Anderson

The biggest risk I ever took was rebuilding my entire life, including the business I had built over 15 years. A few years back, I was the woman who could hold everything: a 20-year marriage, motherhood, a fast-growing photography business, and the endless to-do list. From the outside, it looked successful. Read More>>

Jaxon Dobbins

One of the biggest risks I’ve taken was staying in fashion photography despite the uncertainty, long enough for it to turn into a real career. Fashion is an industry that quietly tests how much instability you’re willing to tolerate. Early on, I was assisting, testing, shooting unpaid work, and investing in personal projects with no promise of return. Read More>>

Anna Major

One of the biggest and rewarding risks I took was in 2015 – my first solo trip to India. Since I was a kid, I have been fascinated with traveling and that interest led me to study history, geography and social studies through my childhood, college years and beyond. Read More>>

Sameeha & Poorna Preethika

As co-founders of Ekayka, an occasion and resort wear label based in India, the biggest risk we’ve ever taken is starting our fashion label right out of university. Read More>>

Hailey Shevitz

In 2022, I moved to California. I had a stable 9–5 job, was in a stable relationship, and had built what looked like a very content life. The only problem was a constant voice in my head telling me this wasn’t it for me. Read More>>

Jessica Suda

For eight years I worked as a probation officer, a career I went to school for and truly loved for a long time. After a few years my husband and I moved about an hour away to be closer to his job, but I kept making the commute because I was committed to my job and the path I was on. Read More>>

John DeMena

Honestly, I think the biggest risk I ever took was moving to the USA alone to pursue a music career. I had no family, contacts, or job when I landed here. Also, building everything from scratch and writing, producing, and recording my debut album ‘Dreams and Lies’ completely independently. Going all in ended up being everything. Read More>>

Ebony Jae

Two years ago, I took a risk that felt reckless and terrifying: I decided to transform my small private therapy practice into a full-fledged nonprofit mental health agency. There was no guaranteed funding, little support, and no roadmap—just my conviction that this work mattered. I had a blueprint, but almost no one had ever done it this way, and there was no example to follow. Read More>>

Zaniyah Jean

I took a risk the moment I came back to music without trying to explain where I’d been. Stepping away was easy. Staying gone would’ve been safer. Time passes quietly when you let it. People forget. Algorithms move on. There’s a strange comfort in being unperceived. Read More>>

Lauren Phelps

After I graduated from college, my first job was at the Department of Labor in the Unemployment Office. Needless to say, this was not my dream job. I stayed there a few years and quickly moved up, getting promoted two times and feeling like the longer I stayed, the more I was stuck. During the covid pandemic, my love for cooking became apparent to me. Read More>>

J0SHH

The biggest risk I’ve ever taken, which really started my Artist career was driving to LA off of two bounced checks. I had just dropped out of college and started working for this shady contractor. Over the previous months, I had been going back and forth I had been going back and forth with myself about going to Los Angeles with the homies… Read More>>

Ayanna Elston

Risks usually involve fear. There was a big part of me that was afraid to continue doing the same thing as everyone else as opposed to betting on myself and starting my own business. Read More>>

Christine Stilley

If you’d told me 7 years ago that I’d walk away from a comfortable job with benefits, a matching 401(k), and predictable paychecks to sell houses for a living, I would’ve laughed and asked if you’d lost your mind. Read More>>

Tarea Smith-Lewis

One of the most meaningful risks I’ve taken wasn’t loud or dramatic — it was internal, intentional, and deeply personal. For much of my leadership journey, I had a habit of announcing what was next before it fully unfolded. That visibility helped build trust and momentum early on, but over time I realized it was also placing pressure on ideas and decisions that needed space to mature. Read More>>