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.

K’nek

Everything that I am now as an artist started from taking the biggest risk of my life back in 2017. I was stuck at a dead-end job that I hated. Six years prior, I was a part of an up-and-coming Christian Hip-Hop group that disbanded abruptly due to personal reasons. Read more>>

Karina Pita

Risk is nothing more than a possibility; a possibility that something might go wrong, but also the possibility that something might go right. It is an integral part of life and one that is inevitable for growth. These past two years have been a learning experience for me – change, loss, realization; these are some of the lessons brought to the surface but more importantly: RISK. Read more>>

Sharon Terry

My children were diagnosed with a rare genetic condition in 1994. Everywhere I looked for any answers about what this would mean for them was baron. There were no answers. I was a stay at home mom, with no medical training or experience. Read more>>

Keyonna Trammell – Persaud

I giggled a bit at this topic in all honesty. The reason being is that the entire foundation of my business is built off a risk and faith. Prior to it’s creation I worked a job that was slowly but surely killing me. I loved what I did in a sense, because it was very rewarding in the fact I was able to help others potentially create a better life for themselves.. Read more>>

Evan Acklin

I have come to fully experience the quote: “Life is all about taking risks.”, as of late. Sometimes, the life we truly desire is on the other side of fear and comfort. In the midst of 2022, my faith has been tested in more ways than one, however, I believe the opportunities and challenges that I endured were specifically tailored to provide me with the characteristics needed for my journey. Thus, my risk was revealed in 2022; this story began in 2020. Read more>>

Tayler Moore

One of the biggest risks I took was quitting my 9-5 job. It was definitely a premature decision to make. I thought I had everything figured out to work full time as a makeup artist and esthetician, but I had one small problem: no clients LOL. Read more>>

Adriana Vazquez

I recently took the risk of leaving my job to pursue my business full time. As a single mom it wasn’t just a difficult decision, it was definitely a scary one. I got tired of working a job that only sees me as an employee and nothing more. My whole life I’ve known I’m meant for greater things and I honestly regret not taking that risk sooner! Read more>>

Elbi Elm

I decided to take the leap of faith and launch my business in 2018 after witnessing a group of women raise over $300K+through crowdfunding to start a co-working space. I thought if they can do it, so can I.  Read more>>

Raine Valentine

My whole life is about taking risks. When I met my partner in 2011 he brought to my attention how important it was to push ourselves beyond our perceived limits. G.T.E. is what we called it… going to the edge. Ever since then I have been open to the blessings that risk taking has to offer. Read more>>

I’lasha James

One risk I’ve taken was trying to obtain my college degree and complete a certification in one year while working in the hospital during the pandemic. Working in the hospital was a burden alone. Read more>>

Josh Gilpin

The biggest risk I have ever taken was returning to college in my 30s to study guitar. I had previously graduated from UT-Austin with a Mechanical Engineering degree, and was already working in the oil industry in Sugar Land, TX around 2007. Read more>>

Jacqueline DelBrocco

Taking risks is a huge part of being an artist. There’s a famous quote – The more you’re willing to try something that might not work, the more you’re thinking like an artist. I can’t remember who said it but whoever it was, they were dead on. Read more>>

Courtney Quinlan

I came up with a plan to start my Matchmaking business in 2008, right before the recession of 2009. This was a huge risk, and many people close to me told me I should just get a safe job with guaranteed stability. Read more>>

Allie Arcos

I’ve always loved art; painting and drawing have always been a relaxing hobby for me, and during the pandemic, I had a lot of free time to do it. I then ran across different people turning their favorite hobby into something they can share with the world. I got the crazy idea that I could do it too. Read more>>

Jennifer Lee

In early 2022 I decided to jump into my business full time. I was tired of waiting for the right moment. When the company that I was working for as a marking coordinator (a career I relocated for) was bought out from another one of our bigger franchises, I decided that I could stay on with this venture and see how it goes, or jump into my business full time. Read more>>

Kimberly Wyms

In December 2019 I was preparing to graduate from esthetics school. I was so excited that the Monday-Friday, 8:15-3:45pm schedule was finally over. I could spend more time with my daughter, have a social life, and finally live out my dreams. The only problem is, I did not have a job. Read more>> 

Ramencoke

Your involvement in the creation of music is always viewed as risky. Every choice you make, including who you collaborate with, where you release your beats, and how your image is presented, contributes to the risk factor. Producers take risks literally in order to enter the music business. Read more>>

Sarah Elizabeth Quigg

After graduating Nova Southeastern University with all Honors, and being qualified to sit for board exams, I was crushed when I had missed the mark by 1 point. This was one of the first times I didn’t succeed in this field, so I had thought. This had brought me pain and despair which filled me with doubt and confusion. Not knowing what to do I began to write. Read more>>

Ronda Wright

I started my travel business in late 2019. None of us knew what was just a few months ahead of us with COVID-19. When the pandemic started in the Spring of 2020 and all travel suddenly halted, I quickly had to figure out how I could continue giving my brand new business visibility even though people weren’t traveling. Read more>>

David Page

Isn’t life taking a risk? You take a risk each time you walk out your front door. Plus, it’s only a risk if you fear the uncertainty and only focus on the negative possibilities. I am only 52 and last year I left a career of twenty two years because it was diametrically opposed to my spiritual being. Read more>>

Roberta Cullen

I spent about 18 years teaching acting and movement classes at a local community theatre in Alexandria, VA and at several public schools in their after school programs, as well as teaching drama classes at a small private school just outside of Alexandria. Read more>>

Em Gallagher

It was never my intention to have my own creative business. I graduated with a double major in Fine Art and Design from the University of San Francisco having secured a job as Chief Creative Officer for an app. Read more>>

Erica Nickelson

Starting something new can always be scary and risky. For me, when I decided to go all in on my health and wellness business, I was honestly terrified! I had major imposter syndrome and could list a thousand reasons that could have gone wrong and questioned myself on if I truly was equipped to be successful at it. I’d ask myself, “What if I don’t get any clients? What if I’m not ready? What if I fail?” Read more>>

Dre Thompson

I take ENDLESS risks as an independent artist and event curator honestly. As an artist, every song released, show booked, etc is a risk because 1: most times the amount of money put out to do any of the aforementioned things rarely breaks even and I know I’ve dipped into funds I wasn’t supposed to to take the risk of breaking even at least & 2: there’s always the risk of the crowd you’re releaseing your art to may not like it or understand it so they don’t appreciate it like the artist does. Both these risks I look at as necessary to get to where I want to be creatively. Read more>>

Damion Hype

April 10th of 2019 was my last day in a corporate office, in January of that year I was told, in 60 days they will no longer have a job for me, right after that, Covid happened, in May they stoled and burnt my car. One after another, L’s after L’s. I then decided, for the first time to focus fully on my music and my Jamaican night club.. Read more>>

Izzy Rawshdeh

I graduated college with a degree in radiology. I worked in the field for a while and then went on to work in the pharmaceutical industry. To be honest it was not my cup of tea, i did not enjoy what i was doing. Years later, i was involved in a car accident where i was severely injured and lost one of my finger int he process. Read more>>

Jessica Smith

I began my real estate career in 2019 during my last semester of college, dedicating about a third of my time between learning real estate, being a full-time undergrad, and working in a full-time manager position. Read more>>

Starr Jackson

During the pandemic I was someone who was doing a lot from cooking different meals, working out, and keeping my businesses in the limelight. After i graduated college in 2019 I knew the “real world” things were coming. I would be working full time and wouldn’t have many things to be involved in like I did on campus. Read more>>

Evan Jenkins

My whole life I’ve written songs. I started off singing melodies around the house and once I learned how to play piano a bit, the writing started. As time went on I realized that some of the songs were all over the place in terms of vibe/genera but that I also had a lot of material that was in a separate box. I liked what was in this box, they were all a similar genera and they all came from within and without struggle. Read more>>

Nathan evans

Response: This is a funny topic to me and if you know me or had known me, I am generally against taking risks and prefer to play things safe. I was raised conservatively and to be afraid of risks. However, when I look back at my life, all my “success” comes from the risks I took at the right times. Read more>>

Leonardo Garay

My biggest risk was putting myself first. Have a profession beyond the common (as many think or underestimate the “barbershop“) go against the current, do something out of the ordinary. turn this fantasy that could only be seen through “my phone screen” Read more>>

Sade Wingate

Taking A Risk? I’m A Risk taker …. LOL I’ve learned that about myself within the last past few years I’ve been a business owner. I truly believe in having faith more than taking risk. Faith allows your wings to save you when it begins to feel like your falling . In many ways building a business is one big decision you have to make not only for yourself but your family as well. Read more>>

Peggy Peabody

I started teaching ballet out of the back room of my mother’s nursery school in 1977. I was a senior in high school. From there, I rented several store front / office spaces as our school grew. In 2012, I had a choice to make; either I moved again and rented a larger space, or I took the plunge and purchased a building to be our forever home. Read more>>

Ivette Moulinier

The start of this business was in February 2020, days before the start of the COVID19 Pandemic and the lockdown of economic activity throughout the country.Considering that this business area (jewelry) is not of first necessity as food or medicine, represented a very high risk for the initial implementation phase, where the local had to be prepared, materials purchased, staff hired, and customers attracted. Read more>>

Mike Pimentel

One of the biggest decisions to make when starting a food business is where to base your operations. Ideally it should be in the right location and have the necessary equipment with room to adapt and expand. This past year I risked moving my operations from a shared kitchen to my own kitchen space, and fortunately it’s allowed me more scheduling flexibility and enough room to grow. Read more>>

Harlen Hill

For as long as I can remember, I’ve always been a creative individual from the first time I ever picked up a pencil to draw to now producing, writing, and recording music that has reached 105 countries, 350,000+ streams, and 20,000+ unique listeners (or as I like to say, supporters) in less than one year (late December 2021 to now, September 2022) of distributing my music to major platforms. Read more>>

Jaren Hampton

The biggest risk I took to date, was to begin producing and putting on my own stage plays. Prior to the first one I had written, I had acted in several, but never did my own. I had studied the blueprint laid out by Tyler Perry, and a couple of my peers producing plays locally as well (s/o Sam Houston & Thomas Mac). This led me to believe that I, Read more>>

Jeny Robinson

I’ve always been a creative person. I enjoying trying to new arts and creating things, ranging from knitting, jewelry making, scrapbooking and a brief dabble in woodworking, but baking has always been something I love! Read more>>