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.

Vanda McCauley

Once, I had a cozy job in the government, with a reliable paycheck. But deep down, I felt a stirring in my soul—a passion for the beauty industry, especially helping people with hair loss. Read more>>

Ra’Nesha Taylor

One of the most significant risks I’ve taken in my life occurred a few years ago during a tumultuous period. I found myself in a job that was draining both my mental and physical health, despite it being initially temporary. Read more>>

Solomon Matthew

Most recently, the biggest risk I have taken was to start an instagram video series. I call it “The Enigma Sessions”. It is simply a weekly performance, whether a cover or an original song that I post. Read more>>

Amy Mahmood

Before taking on the challenge of running a salon, I was a medical student. I found out my fiancé and I were going to have a baby. First pregnancy was very hard on me. My body did not take it well. Read more>>

John Trefry

My journey as a filmmaker has been shaped by 2 massive risks. Growing up in Anchorage, Alaska, I loved movies and dreamed of being part of the magic to actually create them. Read more>>

Jonathan Agustin

I felt that pursuing a career in performing arts would be incredibly risky. Having a Filipino background especially, lots of people growing up persuaded me to go into healthcare for the money and stability. Read more>>

Lauren Hammond

I decided to take a risk in starting my own pet care business in 2022 after experiencing burnout working in veterinary clinics. I have always loved animals and helping people, but the long hours and low pay many technicians experience was starting to affect my health and happiness. Read more>>

Karley Wasaff

More often than not, I lead my life with asking myself what am I scared of, and why. I then act upon that fear, I lean into it and go for it. I strongly believe in re-framing fear as a tool for growth. Read more>>

Candice Hakimfar

I am a mom of three and I was a full-time piano teacher until we purchased our second home. I kept finding off markets and referring my friends to other agents until I remembered that I have my real estate license that I got when I was 21 years old. Read more>>

RJ CHASE

I graduated high school from Lower Manhattan Arts Academy in June of 2017. I hadn’t applied to any colleges and had no plans of doing so. The only money I was making on my own came from playing keyboard & organ in local churches. Read more>>

Myah Daniels

As a creative, I am constantly taking risks. From the macro level of choosing an unstable career, to the micro level of how to say a line in a script. Without risk, there is no reward. Read more>>

Jerry Travis

It was definitely a risk to join High Plains Drifter. At the time I was playing with a band that I had been with for many years. Unfortunately that band and I had a falling out at the time, and right around that time Matt Targos (Sutphin, TF Bundy) got me in contact with Adam, and the rest his history. Read more>>

Jen Murphy

Without risk, there is no reward. I was so scared to take a risk and photograph other indigenous people with the red hand print on their face, raising awareness on this issue. Read more>>

CasinoATX

I took a break from the music / entertainment industry in 2015, after being in the business straight since at least 1997. For years everything I had I poured into music. Read more>>

Taylor Box

My experience of taking a risk begins with a story. About 3 years ago, my father passed away from stage 4, glioblastoma brain cancer. In the process of grieving & coping with his loss, I have spent a lot of time soul-searching. Read more>>

Melissa Hyatt

I was happy as a freelance artist primarily working for a large textile compnay in NYC. After about 5 years with this company one day they just stopped working with me. Read more>>

Christina Marder

One of the biggest risks I took was leaving a corporate job to pursue my career in Esthetics. I had my boss at the time say you want to wash faces all day? Atleast get into Cosmetology! Read more>>

Suchi Gupta

I grew up in a cozy little town at the foothills of the Himalayas in India, commonly called the Manchester of India because of the sheer number of entrepreneurs originating out of that city. Read more>>

Molly Grace

Risk meets reward Is there courage without risk? Many moments as a self-employed photographer have scared me just enough and intrigued me so much that I’m curious and lean on in. Read more>>

Neha Oberoi

Taking a leap of faith away from the corporate world, I ventured into the creative realm of beauty and fashion photography in the heart of New York City. Read more>>

Heather O’Lear

I grew up in a family that prioritized education and knew from a young age my future would include education and a conventional, societally acceptable career. Read more>>

Matthew R. Paden

Transitioning into a freelance visual artist was undoubtedly a bold decision that came with its fair share of risks. In 2017, I formed my brand, Savvy Palette, not only as a means to brand my own art but also to help and guide other artists on their creative journey. Read more>>

Anna-Maria Orlu

The biggest risk I took was betting on myself, I left my family in Dublin, Ireland, finished my master’s degree and moved to Los Angeles to pursue my career in entertainment. Read more>>

Crystal Robertson

Life for me has always been about doing new things and learning what works, sometimes the easy way and other times the hard way. Starting a for-profit and non-profit company completely redirected who I am. Read more>>

Brian Vukadinovich

In September 1981 I was falsely arrested and brutalized by police in Valparaiso Indiana in a case of mistaken identity. I was falsely charged when the police realized they had the wrong person and rather than let me go with an apology, they decided to file a false charge against me in order to justify what they did to me. Read more>>

Amaranthia Sepia & Claire Jones

Written by Claire: We took a significant risk to invest in ourselves after our first Art & Mind virtual film event in 2021. I came across a virtual business class over $6,000 and decided this was the moment to break out of stagnation and self-sabotage. Read more>>

Borba D. Wright

One of the biggest lessons I’ve learned recently is to choose curiosity over fear. Growing up, I always leaned towards things that made me feel comfortable and really never experience different things. Read more>>

Tina Green

I took a risk to write the book, “The Life-Changing Power of Self-Love: An Essential Guide.” This was a risk because after living for decades of my adult life with low self-esteem and being married to an addict with chronic depression, I thought, “If I ever figure out how to be happy and fulfilled, I’m going to write a book about it!” Read more>>

Mélissa Vales

As artists, we are expected to share our talents, inner thoughts and imagination in our work, which exposes us to judgment. As we know, criticism has the potential to damage one’s self-confidence. Read more>>

Santos Torres

Prior to the pandemic I was doing A&R for a record label, and during COVID came to the realization that I had to create my own independent outlet to really be able to support and grow with the artists I wanted to help develop. Read more>>

Jess Schwarz

I feel like at this point in my life, I’m a professional risk-taker, which may be the result of my rural-raised, youth-induced desire to constantly be on the move. Read more>>

Steph Krim

I had spent almost a decade building a career in hospitality that peaked with my dream job as Director of Operations for a big brewery but I was unhappy. Read more>>

Paula Krieg

After graduating from the School of Visual Arts in 1980, I stayed in New York City and ended up living in a community of artists in Williamsburg, Brooklyn. Read more>>

Kenny Allen

20 years ago, I was a part of a thriving soul and hip hop music scene rooted on the U street corridor in DC. At that point, I had been making and performing music full time for about 5 years and had toured the world in support of other artists. Read more>>

Thomas Kaufmann

Starting a small business is always a risk. I believe in myself enough to take on this challenge head on and come out on top. I’ve spent too many years on the sidelines having the would of, should of, could of thoughts. Read more>>

Jennifer Gillia Cutshall

Art thrives on the idea of taking risks. The very nature of being an artist or choosing to work within the arts is perceived as a risk (by society). Without risk and bravery there would be no expression. Read more>>

Madeline Curtis Long

Taking the jump into launching Emory James Creative stands out as one of my boldest decisions. Starting a business feels akin to the anticipation of having children or buying a home – there’s never a “perfect” time. Read more>>

Marcia Williams

The risk I took was deciding to leave corporate America as a young single mother to follow my passion in beauty. I was young, yet too old as many thought to leave my corporate job to become a full time hair stylist. Read more>>

Katherine Bissell Córdova

In my late 30s and into my 40s, I had two kids. When my kids were little, I decided to change careers. I had worked for 20+ years in the nonprofit sector in some intense roles-working torture survivors here in Chicago and as a human rights defender in Guatemala. Read more>>

Amanda Scarpaci

When I started my business, I was 20 years old. Still in college, very much trying to find my way. One weekend, I emailed event planners in New Jersey, asking if any of them were taking on any interns. Read more>>

Leslie Jorgensen

Becoming an artist is a risk in itself. It involves putting yourself on display and inviting critique. But it also means taking a leap of faith in finding out who you truly are and what you can do. Read more>>

Todd Hutchins

I previously was employed with ABF Freight and worked long hours. I always had the dream of being self employed. Once I started doing leather work, I really enjoyed it and used to dream what it would be like to quit my job and work for myself making leather products. Read more>>

Stelle Oettler

One risk I’m beyond grateful for taking is when I moved to New York City in June 2021. It felt like a new and unexpected chapter of my life began. Read more>>

Anu Yadav

I think deciding to pursue creativity and art in any form is always a risk, and its about centering your own well-being and mind in a society that constantly tells so many of us we are not enough, that we can’t think, and that we don’t get to honor our inherent creative genius. Read more>>