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.
Adita Yrizarry-Lang
The pandemic brought about an array of challenges for most people, but for me it was the beginning of the best part of my career. Although I toyed with the virtual space, I was now forced to make it work. During 2022, I was coaching clients, teaching classes, and working as a health coach for Cigna. I needed the security of a job, since I was a single mother newly divorced. The pandemic shut down my division with Cigna, as well as many of my other teaching opportunities, and I was left jobless overnight. Read more>>
Daisha
Today I have chosen to take a risk, I want to share photos and the intimate healing journey that is the story of my body. My journey with body positivity and empowering all individuals to own their perfect existence that was crafted so meticulously and beautifully expressed in the concept of what we perceive as the human mind & body. Read more>>
Tyler Townes
Being an entrepreneur is a tough task which involves several risks. Taking a risk was never something that was foreign to me, but always gave me an uneasy feeling no matter how many times I did it. When starting Trained 2 The T, I knew that it was possible and I knew that I was capable of doing so. I knew that working a corporate job all my life was not what I wanted to do so what better time to start my business than the present? Read more>>
Lindsey Soza
I’m not much of a risk taker. I hate not knowing the outcome and if it will be good or bad. However, the best risk I’ve taken is becoming a business owner of two businesses. My first business Jaasi K Jewelry was a huge risk and investment for me. I wanted to do this because I had just had my son and i wanted to pursue financial freedom. I wanted another source of income coming in. Putting myself out there and not knowing if people would support or even like the jewelry was terrifying. Read more>>
Rachel Bowman
It was June 2020, the peak of the pandemic, when I decided to take my business & go completely solo. I wasn’t even technically working due to my job being “non-essential”, yet I still decided to take the risk & step out on my own. I had spent the previous 4 years working in hair salons, renting a room, & relying on the salons to help build my business up. So when deciding to go completely solo with no help from anyone it was scary. Read more>>
Daniel Gould
When i dropped everything and moved to LA to pursue music. I had been making music and booking show for a few years in my hometown of Dallas Tx and while i learned so much and accomplished some really cool things like Preforming Emo Nite, Booking music festivals, etc. I still knew there was more work to be done. I had to take a risk and go to LA where the opportunities would be multiplied, even though i love my hometown. Read more>>
Jim Ristuccia
Getting out of the Navy and then jumping into 100% commission sales as a head hunter is one of the biggest risks that I’ve taken. In the Navy I was really comfortable. I had a lot of fun for a while–almost a decade–but then I got into a job that wasn’t so much fun, really hard work and very little appreciation. I looked at the future if I stayed in and decided I wanted to be doing something more positive. So I decided to get out, except I didn’t have a plan for the next step. Read more>>
Kwasi Ransom
Taking my art seriously, and doing it as a professional has been my risk. Last year (2022) in April I started making music for TV film. I joined an online course my friend Josh Williams, a production music composer in Kansas City, put on and I would do weekly meetups where I would share music and cues I made for production use (TV, film, video games, etc.) with a group of passionate students. Read more>>
Tiffany & Whitney Bishop & Coble
A risk we have has been valuing our worth and taking the initiative to step out on our own. We specialize in black women’s mental health, and often we have to give a disclaimer of why we hold space for black women and couples. A constant struggle is proving why black women deserve priority in their mental wellness. Our practice addresses challenges and provides a safe place for black individuals who are not often held with open ears. Read more>>
zerina hutchinson
I was an art major in college and always thought I’d be in some sort of industry that I could be creative. Once I had my first kiddo I decided to open a home bakery and create custom cakes. I did this for close to six years because I had the opportunity to stay home with my kids while doing something I was good at. I got burnt out and decided to close down and stop taking orders. What was once a passion turned into such a chore and I stopped loving being creative with baking. Read more>>
Tatiana Chamorro
Most of the decisions my husband and I have made as business owners, professionals, or even humans, are risky. In 2014 after w sold our car, our only possession at the time, we decided to use the money and move to Texas from Nicaragua, for 1 year, to pursue his M.B.A. Talk about risk. Back then we had a 2-year-old boy, and we had never experienced living on our own as new parents. We had no idea what we were doing, but the one thing with risk is you have to take on EVERY opportunity along the way. Read more>>
Christenelle Diroc
Back at 14 Years Old With My 4x tee, I Was Watching Smack DVD So Much I Had became a Student To The Hip-Hop Game. At this Time I Was Going to a School Called Syracuse Academy Of Science And D- Block Was One of My Favorite Groups ( The Lox ). I Was truly excited When I Heard Styles P was coming to Syracuse, I Was going nuts. So Me and My Family Friends were in a Mall called Carousel Mall, Which Now is called Destiny USA. Read more>>
Aldi Essandjo
Stepping into everything I am operating in now was the biggest risk. Everything you carry within you will require tremendous faith and trust in God, for you to walk into. But the keyword is to “walk.” As long as you’re willing to do the walking, no matter what you cannot see, everything you know is in you will be fully brought to life. So, walk! Read more>>
Brendan Jeannetti
In March 2020, I got let go from my job as an on-air radio talent in a phone call that lasted approximately 53 seconds. I wasn’t all that upset to be honest. I felt confined to that role because it was a great opportunity and I was young, however, I now had the freedom to pursue other endeavors for the first time in years. Unfortunately, the world was shut down due to COVID-19, but still, I had this overwhelming sensation of freedom that I needed to act on. Read more>>
D’Andra Drewitt
Becoming a full-time business owner begins with you jumping head first and not looking back. I quit my job at the news station in 2017; it was the best day of my life at that time. That was a risk I was willing to take. However, the backstory to that day really stems from what I had been building since 2013. When I started my photography company in undergrad I knew that one day I would be operating SayDrewitt|Media day-to-day. Read more>>
Mikael Coleman
Growing up in a Caribbean household the medical field was the only path in life that ever felt realistic to me. There’s obviously stability going into medicine, but there was also this unspoken added pressure as an only child and first-generation American in my family to make my parents sacrifices not go in vain. Read more>>
John Johnson
A huge risk involves a very recent time in my life. To tell the entire story would be too long but some highlights would be that this was the highest paying, most benefits providing, and highest level achieved position that I had ever had out of college. Read more>>
Dani Waldman
In the field that I work in, we talk about taking bold risks like leaving the 9-5 job, speaking out boldly, saying goodbye to a relationship or something that feels striking. It’s like this big statement that has to take place. And the big statements are beautiful but I also want to illuminate on the subtle aspects of life that are still very much in the field of risk taking. Read more>>
Masha Jung
Last couple of years have been very tumultuous on the global scale. The world went from open boarders and globalized economy to full enclosure in 2020 and back to travel with added difficulties of the misplacement and migration trends caused by world conflicts externally and local shifts resulting from the post pandemic circumstances. Read more>>
Maria Muñoz
When I was told about becoming a microblading artist, I was intrigued. I took my savings and invested in microblading training that took place in Jan 2022. I will not get into depth about my personal experience, but I knew there was so much more to learn. Read more>>
Denisse Urbina Ledezma
The biggest risk of all was when I decided to ask my husband to come and join me in my profession. He worked in Demolition all of his life since he was 18, He worked nights so I couldn’t depend on his time, and He had just finished his classes and got his HVAC License a few months ago so he was ready to start with his new career. Read more>>
Meghan Asselta
I believe being a small business owner is a risk in itself! I graduated with my BFA focused in Photography from Pratt Institute in Brooklyn in 2014. After graduating and trying to “hit the ground running” I quickly learned it wasn’t going to be easy. I have had my business for 10 years, and have only just recently been confident enough to have less than 3 jobs. Read more>>
Toni Lorraine Johnson
Like most people, regardless of color, being born into poverty can be a death sentence at birth. I am no different, but I didn’t know I was poor until I got into middle school when my mom would buy my sneakers at the supermarket all the way in the last aisle of the store. I have a picture of me with my volleyball teammates and I’m in shoes because my mom said I went through too many shoes. Read more>>
Tyler Mae
That story is still currently being written. I am always taking a risk , betting on myself every day. It is my personal go to be 1% better than I was yesterday. The beginning of the risk began when I got my first few bookings on a feature film by Steve Carell, hit tv show as an extra. Read more>>
Amber Kerby
I didn’t start out as a rebel. On the contrary, I spent a lifetime fitting in. Don’t get me wrong, I found small outlets for individuality, but nothing that would make me stand out too much. I quietly built a life, an identity, and a business that society found acceptable – admirable even. Read more>>
Angelika Koch
One of the biggest risks I took was to openly talk about my past on my platform. To be vulnerable in front of hundreds of thousands–and sometimes millions– of people made me feel exposed and uncomfortable. I didn’t want people to look at me like I was broken because of my past. I wanted to share my past with people who were going through the same thing, so I could be a beacon of hope for their future. Read more>>
Richie Ray
I’ve been taking risk for as long as I can remember. When i was 18 i packed my stuff and moved all the way from Detroit to California (Bay Area) for 2 1/2 years to chase my creative/entrepreneur endeavors. I had $800 to my name, enrolled in fashion school to study product development to gain the necessary skills to build my fashion brand called, Seuleur. Read more>>
MilesPerHour
Well for one, i think that genuinely believing i can make it in the music industry might make me borderline insane. But I’m okay with that. It’s been a long journey as an independent artist, so far. One of my proudest moments up to this point though has been putting together my own show for artists, including me, to perform in front of a live crowd. Read more>>
Corynne Burrows
Life is all about calculated risks. Read more>>
Zoe Braun
I was never the kid that knew who or what they wanted to be when they grew up. Coming from a small family and raised by a single mother, I worked from a young age: babysitting as a tween, getting my first paycheck at 14 and a half (the legal minimum age for a worker’s permit), and never being unemployed since. Read more>>
Laura Velasco
In summer of 2019 I uprooted my entire life and relocated from Minnesota to Arizona. I was separated from my partner, but I needed to go further. I packed up everything I had (including my dog and cat), and headed to the Southwest. 6 months later I filed for divorce, resulting in me flying solo for the first time in 12 years. It was scary, but it was so liberating. Read more>>
Janelle Doyle
We are a family-owned and operated Kettle Korn Company in Charlotte, North Carolina. My name is Janelle Doyle, a little bit about me I’ve worked in the banking industry for many years after graduating from the University of Pittsburgh. I decided to move to Charlotte, NC from Pittsburgh, PA in 2015 to advance my career in banking. However, to become an entrepreneur was my dream so I figured new city, new life, no better time like the present. Read more>>
Danni B.
After losing my job in Atlanta, I was encouraged by a former friend to leave my parents & the life I knew, to move to Charleston, Ms. and pursue my beauty business. The person that I moved with ended up leaving me stranded in a new city/state all alone, and as upset & scared as I was, I decided to turn that pain into power & progress. I worked my butt off & was able to move from Mississippi to Tennessee within 4 months, and I opened my 1st beauty bar in Charleston, Ms. 3 months later! Read more>>
Suhay gonzalez
I took a risk by investing my own funds to bootstrap my small business. Utilizing my saving to develop, create and launch my brand required dedication, planning and self accountability. As a new brand and experienced Financial Officer, I knew that I had to believe in myself and put my own money to work. Read more>>