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.

Alexis C Austriaco

A huge risk I have taken is stepping out of my comfort zone and leaving my 9-5 job and going all in for my businesses. The henna business, Love is Mehndi henna design, started off as a hobby in 2007, doing free henna for friends and family members or anyone willing to be my canvas. Read more>>

Ollie Moore

My biggest risk was leaving my 9-5. A lot of times we hear that we should stay , I agree until staying interfered with business. Read more>>

Julia Fehrenbacher

Finally, and right on time, you will remember you were never meant for the beaten path. The above (and below) italicized words are lines from a poem of mine entitled “The Mighty Sage.” Read more>>

Mia Schuster

I think risk is the whole name of the game. When I consider my journey and any of the major moments that stand out, they all demanded risk to be taken. No going over, under, or around it – only through. Read more>> 

 DJ Asthmatc (Kyle Francis Ordona Dacallos)

Becoming a DJ stands as the biggest risk I’ve ever taken, a decision I made at the age of 18. My inspiration sparked from watching the Netflix series “The Get Down.” Read more>>

Nabria Robinson

When I think of the word risk at first I used to be terrified. What if something bad happens? What if things don’t go the way I planned it in my head? Just a lot of thoughts running through my head. Read more>>

Madeline Adams

I’ve been modeling professionally for 6 years and lived in Boston for 5 of those years. Boston became home for me through college (attended Boston College) and most of best friends stayed in Boston after college to start their careers. Read more>>

Debbie Jason

Treating mental health disorders that result from trauma can be messy. After years of training and working across different treatment settings from residential treatment centers to outpatient clinics to acute inpatient wards, I realized the diverse impacts that trauma has on mental health. Read more>>

Lillee Monet

Recently, I received the largest wedding inquiry of my career: a two-day event with over 400 guests, requiring travel and accommodation. Read more>>

Yossi Govrin

“Building a thriving cultural center with no city or state funding”. Through a profound commitment to the freedom of thought and action, I identified a Coultural void within the city.  Read more>>

Sydney Smith

In January of this year, I took the biggest risk of my life. I did a complete 180 with my career, quitting my corporate job as a scientist in pharmaceutical development to pursue my passion and figure out what I truly want to do. Read more>>

Libby Kay

I’ve been writing for over half my life, and I won’t age myself by telling you how long that is! ;) I’ve always wanted to be a novelist; wanted to tell lovely, sweet stories to make people smile. Read more>>

Taryn Ferro

Owning a business is committing to taking risks every day. I’m actually in the middle of a risk taking adventure and right now with my endeavor back into film photography, my OG medium of choice.  Read more>>

Casandra Mandeville

I am a very adventurous person, I’ve been teaching my daughter this as well, since she was born. When people claim something is dangerous, I love to head up and face it and see if it is really dangerous or not. Read more>>

Jason Rosell

One of the biggest risks I have ever taken was starting a wellness company from scratch. I was told but 100’s of people that unless you have a perfect body, are super tall, and amazing looks, that the chances of succeeding in the television/wellness/fitness space would be extremely difficult. Read more>>

Camille Blott

Taking risks is scary, and is something I can definitely admit having an aversion to. But like anything, the more you practice it, the easier it gets. Read more>>

Lisa Harpster

Leaving my teaching job to get Antifragile Brewing & my art business off the ground was one of the most daunting yet exhilarating decisions I’ve ever made. Read more>>

Heather Gibbons

In November 2019, I lost my dad to cancer. We knew he had limited time and moved him in to care for him, but it was still hard. The day after he died, I got biopsy results from a suspicious mammogram that confirmed that I had an early stage breast cancer. Read more>>

Bennie Mitchell

People take risks for all kinds of reasons. Some take financial risks to get rich. Others put their feelings on the line to get to know someone better. Read more>>

Katie Murphy

When I was in my early thirties with three small children at home and an abandoned first career, I found myself hit heavily with the realization that this is my only life to live. Read more>>

Mahna Ghafori

Once upon a time, I was shy and followed all the rules of society’s path. I was trapped in a boxed mindset, and seemed like the last person who would ever ‘break free’ from the conventional matrix. Read more>>

Laura Reeve

I think the one risk that got me to where I am today is my decision to apply for the Design school at NC State halfway through college. I started at NC State University in Environmental Science because I had the grades and the expectation that I would be in STEM. Read more>>

Constance Scharff

One of the most difficult things for a person to do is the work to heal from addiction, trauma, or other mental health issues. It can be absolutely debilitating and truthfully, excruciating to feel the feelings and move them through your body. Read more>>

Jessica Shelley

One of the biggest risks I have taken was deciding to leave the classroom (and the comfort of a teaching contract) to venture out into “Startup Land”. Read more>>

Revi Ferrer

The excitement of life lies in our acceptance that we don’t have all the answers and that growth is achieved by stepping into the unknown. Read more>>

Lor G

My biggest risk that I took it was when I left everything in my home country, Brazil, to come out here to the United States by myself to pursue my dream, which is to make music. Read more>>

Michele Bishop

I have been in the dental field for over 30 years, I started as a dental assistant, fell in love with teeth and the difference dentistry makes in peoples lives and went back to school to be a dentist. Read more>>

Laura Young

I had been a working actor for over a decade and in 2019, I decided to write a one person show about my divorce. It was risky financially. Read more>>

Susan Binkley

I love taking risks. In fact, I once opened a large horse boarding operation when I knew very little about horses, and I opened a bakery when I didn’t know how to bake. Read more>>

Yu Hin Bryan Chan

I fell in love with Musical Theatre when I was an undergraduate at the University of Michigan, but that came with a twist. I’ve always despised the hugely extroverted style of Musical Theatre.  Read more>>

Ghost Beach

Growing up in Idaho Falls, I (Kaleb), decided to move to Boise to move closer to a creative and lively music scene that wasn’t around in my hometown. Read more>>

Rafael Serralheiro

Moving to a new country has been the most significant risk and most rewarding achievement of my life so far. I originally come from Portugal, a warm place in western Europe with great weather and food, Read more>>

David Chrzanowski

I had the opportunity to write and direct a passion project of mine that was some thirty years in the making, a short film called “The Alibi”. Read more>>

Chanel Laurice

In 2020 at the onset of the shut-down due to COVID – I submitted my two week notice at the bank with no job lined up. Searched for my new apartment online. Read more>>