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.

Niccole Coleman

When it comes to taking a risk, I’ve taken many in my forty years on this earth. As a midwest girl who was looking for her place in a big city while building her own avenue, I had to get comfortable with different levels of risk. Initially, I took a risk by moving from my home state, Missouri, all the way to Georgia with no job and only a couch to sleep on with my pup, thanks to my amazing cousin. Read more>>

Carol Teitelbaum

I am a person with a very busy life, a full time private practice, Husband, Children, Grandchildren, speaker at conferences. one morning, fifteen years ago I awoke with the message of what I was going to do next in my life. I said to my Higher Power, I don’t have time for that. The message would not go away. It was you are going to help men who have been sexually abused. Read more>>

Sydney Jackson

I think my whole life has centered around taking risks, sometimes without me even realizing it. The most prominent risk for me was my decision to take a gap semester from college last year. My college journey has been all over the place, from changing my major four times, realizing that I was extremely neurodivergent and needed to be medicated, and even being at my lowest point mentally. Like most impressionable kids who don’t know themselves, I went to college because I felt it was my duty. Read more>>

Vickie Chiang

During my upbringing, tattoos were not commonplace in Taiwan and certain Asian countries, so they never caught my attention. It never crossed my mind that tattooing could be a career path for me. In fact, I only became a tattoo artist at the age of 37. Prior to tattooing, I focused on textile patterns and stationery design in the San Francisco Bay Area, which I thoroughly enjoyed due to my passion for decorative arts. Read more>>

Jiovani Cervantes

To tell you the truth, I’ve never really liked the idea of playing it safe in anything when it came to my life. Where would the fun be in that? I always wanted to be the one who pushed boundaries, who thought outside of the box, or took the road less traveled by. Thinking this way as an adolescent had taught me at a young age, that the rewards are greater on the other side of risk, chance, and fear, but you’ve got to be strong enough to see it through. The end result is always the same for me now these days; “all of what I just went through, so damn worth it!”. Read more>>

Emma Ottenhoff

I started my private practice in 2022 after deciding to leave my much loved job in intensive home-based therapy, where I was serving youth and families experiencing a range of high acuity mental health challenges. In home-based work, I was able to see clients in their home, community, and schools. I have a passion for working at the intersections of community and clinical work, and this job was exactly that. I absolutely loved working with my clients and families, however working in the community mental health setting has systemic and structural challenges which led to burnout. Read more>>

Karry Ka Ying Poon

Embarking on the journey to become a tattoo artist was a leap of faith that took me across continents and beyond comfort zones. Leaving my secure job in my hometown Hong Kong, I ventured to the U.S., a place where I knew no one. It was a risk-filled adventure. The decision to swap familiarity for the unknown was daunting, but the desire to pursue my passion for tattooing gave me courage. Read more>>

Carla Tamburro

I took a risk starting my own private art lessons. Before I could take such a risk I had to believe that I had something to offer young people no matter what their ability. I had to believe in myself. I was offering a service and one that is often perceived as being fulfilled in the normal school day. In fact art is an after thought in most school settings and serves as a prep for teachers or entertainment. This is not to say there are not fabulous educators in classroom settings but schedules, resources and logistics sometimes take precedence over good solid educational choices. Read more>>

Kate McGunagle

For most of my life, I have struggled to make my art a priority while also maintaining basic financial security. I simply resigned myself to society’s belief in the “starving artist” — the notion that full-time art-making always comes at a high cost, or is virtually impossible for the average creator. I called myself an “artist with a day job,” yet those freelance gigs and day jobs I held always took the lion’s share of my personal energy, making it difficult to create in my off-hours. Read more>>

Sahil Juneja

The biggest risk I took was to become a filmmaker, it’s a job that requires utmost patience, passion, hard work, presence of mind or any/every skill that any other profession requires. It is a job that takes everything from you, your blood, sweat and the little bit of money that you have. It was the year 2015 when I was in high school and I decided to become a filmmaker. Read more>>

Helen Shephard

I quit my TV hosting job in London to move to LA with no job offer or clue how I was going to make it work. I just knew I had to listen to my gut and take the leap. I had been in a dark place in London, I was partying too much and had no direction. I knew I wanted a more fulfilling and creative life for myself and needed to make a big change. It has not been easy and there have been many trials along the way; Read more>>

Alison Cook-Beatty

My entire life has been a risk. I am a risk taker. I am an artist. Pursuing a career in arts is risky. There’s nothing to fall back on. There’s no financial support. Is it an unknown or significant? But I took the risk. My father told me to do what I love, and I could never go wrong. I felt lucky that my parents supported me and made that choice. But I knew that I needed to support myself and get a job. I took the risk, and I’m glad I did. Every audition was a risk; you have to put yourself on the line, and there’s a lot of rejection. Read more>>

Ian Roberts

I think taking the decision to work as an artist is a risk. When I was at art college, I remember the guidance counsellor at the college said to me, point blank, “You can’t earn a living as an artist.” The guidance counsellor of the art college. As it happened my father was a painter. A number of his friends were painters and they all earned a living doing it. So I knew it was possible. But you do have to trust that that small voice inside you that is steering you in that direction. Read more>>

Marina Mukandala

The biggest risk that I have taken in my life was opening up my yoga studio, in March of 2012. I had held myself back from doing so for many years, out of fear. What scared me the most was fear of failure. What if I open my doors and no one comes? What if I’m not as good as the competition in the area? What if don’t bring in enough business to cover my overhead expenses? These questions and many more plagued my thoughts. Read more>>

Dr. Jeremy Brook

Reflecting on my journey, the most pivotal risk I took was back in the late 1990s, as a chiropractic student. I realized then that the traditional path in healing didn’t resonate with me. I was driven to create something unique – a healing center that integrated more than just physical adjustments. So, when I graduated from chiropractic school in September 2000, I had a radical vision: to create a unique healing space and system, something humanity had yet to experience. Read more>>

Kim Romain

When I look back over my 20+ year career journey, I’d say I’ve taken a lot of risks. I didn’t necessarily recognize them as risks in the moment, but you can’t go through six major pivots and NOT take a risk. I graduated with my BA in Theatre and Film, sure I was headed to LA to be a director and producer. Read more>>

Dylan Emmet

Some moments, you never forget. I had just found out that I was a father. I had a two year old daughter I never knew about living back in my hometown in Upstate New York. My entire life, I had planned to live in Los Angeles and make my music career happen there. All of a sudden I was hit in the face with reality. I need to leave LA if I want to be a good father. Not only that, but by leaving, I might be sacrificing my lifelong dreams in music that I had worked feverishly for my entire life. Read more>>

Julia Furst Morgado

There have been two pivotal risks in my life that reshaped my trajectory both personally and professionally. The first daring move was leaving behind the familiarity of my home country, Brazil, and embarking on a solitary journey to the United States. As a successful lawyer in Brazil, I decided to challenge myself and venture into uncharted territory by pursuing a business education at Berkeley. Read more>>

Diane Gilman

I always, from the time I was a toddler, was obsessed with fashion and knew I wanted to be a part of it. However, I had no support from my family, they only created obstacles. And I had to make a choice between my family or my career. And I went for my career, in a time when women didn’t do that. I got into the fashion industry by happenstance, by opening a boutique with a friend of mine from UCLA, Rosanna Norton. We sewed all the dresses for the boutique ourselves. And one day we had Cher walk in and buy out the entire store!  Read more>>

Chesney Claire

I took a risk when my mother and I decided to leave our hometown to follow my dream. I was born and raised in southwest Louisiana and I graduated high school in 2019. Following high school, I was awarded with an academic scholarship to LSU…but after all of those years of work in academics, I chose to focus on making myself happy. In the years prior to graduation, (2012-2019 to be exact), my parents divorced and I had mourned the loss of my brother, my grandmother, my biological grandfather, and my mother’s stepfather. Read more>>

Steve Gustus

Life is all about taking risks, if you never take a risk you will never achieve your dreams. I took a risk of leaving a 9 to 5 job to Dj full time. I think that you can’t get anywhere in life without taking risks. If you are not willing to risk the unusual, you have to settle for the ordinary. I am very passionate about Djing. Read more>>

Diana Stelin

Taking risks is far scarier than facing just one challenge. When everything seems to be working, when you’ve invested years in mastering strategies and mechanics, the prospect of scratching it all and venturing into a different industry is daunting. Read more>>

Jan McCarthy

I started making art for the first time and took up it up as a profession around age 55. It’s turned out fantastic. It’s never too late to start something and succeed. Read more>>

Natalie Lee

In 2021 I really wanted to do a styled shoot. I had this amazing idea in my mind but there were so many moving parts. I finally decided to take a leap and call Kayla with Ashton Imagery. We had never met or spoken for that matter, but we hit it off right away! The shoot ended up being a great success and it really made my business explode! Read more>>

Salvatore Sissa

I am originally from Lima, Peru and I left my country at the young age of 18 when Berklee offered me a scholarship to study music in Boston. Music being my passionate and life purpose, I immediately took the opportunity and have been living in the United States since 2020. After finishing my studies in Berklee in August 2023 I started my Optional Practical Training (OPT) which allows me to work in the US for 1 year limited only to my field of studies. Since I studied Music and Audio, those are the only areas in which I can legally work. Read more>>

Sage Hill

A narrative of the risks undertaken at Sage Hill Rentals unfolds from the very core of our business. Embarking on this venture while juggling a full-time role, family responsibilities, marriage, and navigating a fiercely competitive regional market entails a monumental risk. Launching a business. Read more>>

Aquiles Chavez

Moving to California and pursuing what I like to do. (Boxing/ acting) Been here for 2.5 years. Lost around 35k in the crypto market. Lost my savings.
Slept in the floor for 3 month and now we on track. Have build a foundation and we coming hot 2024! Read more>>