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.

Dora Tramel

For years I have wanted to quit my job and pursue being a full-time entrepreneur but I was reluctant because I did not want to struggle financially. You know when God puts something in your heart and mind, your soul yearns for it. I was very overworked and needed a sabbatical from work. Read more>>

Emily Phelps

I was a stay at home mom for years. I’ll always say and stand by that being a mom is the greatest job in the whole world, but I feel like I was so put into the mental box of “if I’m a mom (and at that time a wife) that’s all I can be”. Read more>>

John Courage

Decades ago I knew that any conventional career path wasn’t going to satisfy deeper yearning and curiosity I had. I decided about ten years ago to get serious in diversifying my skill set so that I could get more work in the music industry, and spent the years since 2018 as a freelance session musician, performing artist and session musician. Read more>>

Noah Kocher

Taking a risk in my work has always suited me, it explores the unknown which is where I believe magic can happen. This can be applied to any artist, whenever you try something different, you will find yourself in a place you’ve never been before, which will lead to experimentation. Read more>>

Zak Lee Guarnaccia

What others call failure, I learned and call the increasing of opportunities. From a young age, I was and still am an unstoppable entrepreneurial and physical risk taker, following my passion to achieve my dreams. Im a stuntman and actor, sometimes called stunt-actor, or action-actor, through my life journey to pursue my dreams Read more>>

Kayla Rodriguez

The biggest risk I’ve taken in life was Moving to NYC from Detroit. Growing up in Michigan had its ups and downs and I found myself always in the center of trouble. I joined the arts with a friend so they wouldn’t feel alone and ended up falling in love with acting. I originally moved to NYC wanting to be an actor. Read more>>

Lisa & Scott Cylinder

We began our creative venture together as collaborators making a wholesale line of jewelry. As it grew and became successful, we found that the grind of orders and repetitive work was wearing us down both mentally and physically. And while it provided our family with means, it was not fulfilling our creative needs. Ten years into our business, we decided to take a risk. Read more>>

Prue Jeffries

Sometimes just living each day as your authentic self comes with risk and takes courage. Although I was a Professional Surfer – risk, taking is not something I am inclined towards. I am not driven by adrenaline seeking. I am a creative, open and curious person who likes to have the freedom to explore life. Read more>>

Christiaan Tahyar

So, back in 2019, I decided to take a pretty big risk by starting my own business, Moose Mob Media, with a good friend of mine. Before that, I had mainly worked as a camera operator in the media industry, and while it was cool, I felt like I didn’t have enough control over my life and the kind of creative projects I could work on. Read more>>

Nicole Haring

Life is all about the unknown, as the only thing we really do know is the present moment and that moment is just a blip of time along the broad spectrum we call the timeline of human life. If we only know now, shouldn’t we all be taking risks, well aren’t we all taking risks? Read more>>

Ginger Snaps

Choosing to pursue a career in the arts in America is a risk in and of it’s self, full stop, but doing so as a plus size performer certainly makes it more so! Read more>>

Phoebe Cornog

Everything about my career has been a risk. It was “risky” to go to art school and pursue a career in the arts. Everyone always questioned how I would be able to make money. Then it was risky when I moved to California after college. I had never been to California before but I had a dream of living here and working in the action sports industry. Read more>>

Nichole Sellden

Starting Post Meridiem was one of the biggest risk I’ve taken. It was early 2020 when I decided to leave my current in-house marketing job to pursue the world of entrepreneurship. I wasn’t sure I was ready to take the leap to start my own business, but was passionate about the startup space and wanted to pivot my career in that direction. Read more>>

Yun Yao

As an artist, I’ve learned that taking risks is an important part of the creative process. At one point in my career, I found myself at a crossroads, questioning whether I should be Read more>>

Nicole Denes

One of the most helpful things I’ve learned throughout my years as a mental health therapist, pitching instructor, performance coach, former athlete, and former young girl, current woman is this: Read more>>

Jon Steenbergen

I had barely 6 months left in the Army, I was driving 2 hours in traffic each morning and 2 hours home every day, things were getting stressful to say the least. I remember sitting in traffic looking around me at everyone else in their car and wondering if I was going to live like this when I got out of the Army and for the rest of my life like everyone else. Read more>>

Amanda Moser

One of the biggest risks I’ve ever taken in life was deciding to pursue my dreams. To create a career focusing on cannabis is sex is ultimately choosing a career that some consider controversial and taboo. How cannabis influences one’s sex is not widely studied and I am one of the only researchers who have dedicated their career to the intersection of cannabis science and human sexuality. Read more>>

Sarah Lightman

I’ve taken a lot of risks in my life. I decided to pursue the career I wanted, and then changed careers twice to return to my true love of music. When I graduated college I blindly moved to Los Angeles to find myself, my people, my career, and make decisions that I wasn’t prepared to make. Read more>>

Rhiannon Stark

Throughout life, we as humans are faced with countless decisions every day that we make without realizing it. Looking back at my life from where I am now, I can see very clear moments that changed everything but could have been so easily missed if I hadn’t been willing to take a risk. Read more>>

Rian Finnegan

For us, countless business decisions could be considered “taking a risk” – and we wouldn’t be surprised to hear a similar sentiment from other business owners or entrepreneurs as well. Read more>>

Savannah Williams

Heyyyy thanks for having me back! Well a risk ive taken and i wish i didnt, was leaving everything behind to go film a show that didnt recieve the recognition it or i shouldve gotten. I left my job i had a great job working from home but shouldve known not to do that. Read more>>

Don Dobson

It’s 2013 and I’m working as a security guard back home in Sacramento. The job was cool and all but it wasn’t enough and I felt my life was at a crossroads. I needed to figure out what I wanted in life. One thing I knew for sure was I wanted to move out of Sacramento and move to San Diego. Read more>>

May Lobo

Throughout my life I have taken different risks in life that have made me be who I am today. But regardless of that, a little over a year ago I made the decision to move to the United States. I was born and raised in Spain, Europe, and I was living a life that I couldn’t complain about. But I always wanted more and I wanted to move all around the world. The thing is that I met in my hometown who today is my husband (he is dual citizen, Spanish and US citizen). Read more>>

Vyolet Blyck

My first really big risk was launching my own business in my late 20’s. I decided I wanted to travel the world and make over $20k a month and so I did. I had never worked for myself but working for other people left me feeling horrified. I was laid off from a job in Brooklyn and my entire identity was predicated on that job and that persona. Read more>>

Sandra Henry

One of the biggest risks that I have taken was quitting my job to pursue my passion in doing hair. I didn’t know where it would take me but i knew i didn’t want to work for anyone ever again. It was more like a leap of faith honestly, I had a plan and I was not letting nobody distract me. It’s all working out thanks to God I never went back! Read more>>

Kerry Gates

I think of myself as an accidental curator. I purchased Fogue Studios in July of 2020. Perhaps the riskiest thing I have ever done. The pandemic was in full swing, I had a full-time career in tech and I had no idea how to run an art gallery. But I love art. Read more>>

Enesha Duncan

The biggest risk I’m taking is the path I am on now. After the injury I’ve gotten at my previous job in 2022 everything has completely changed for me. Aside from the fact I had a broken bone in my foot, I’ve come to the realization that I wanted to be my own boss, I wanted to do and have something I can be really proud of. Read more>>

Watson Mere

In September 2018, after receiving my Master of Business Administration from Florida A&M University in 2015 and working in corporate America in Philadelphia, PA for three and a half years, I left everything I knew and built in Philadelphia and moved to New York City with only two months of capital in my bank account to survive and no concrete plan. Read more>>