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.

Darnell Brown

Back in ‘04, I landed my first job as a graphic designer at a promo products firm at age 19 – four months after graduating from college with an Associate Degree in graphic design. Four years later, I’d outgrown my role and couldn’t ascend any further at that company, so I tried to get work elsewhere.  Read more>>

Lakshmi Nymisha Gummadi

After completing my undergraduate degree in Architecture and gaining industry experience, I took a bold step. I relocated to the USA to pursue a career in Production Design at the prestigious American Film Institute. Read more>>

Alex Lunstra

In Oct 2023, I accepted my first gig as a “Paint & Sip” instructor. Having never taught a class before, I felt unqualified. However, a friend & old classmate had mentioned me in a comment – their friend owned a bar & wanted to host an event… but they needed an artist. Read more>>

Deniz Sehovic

Starting my own business in my late 20s was one of the biggest risks I’ve ever taken. As a Bosnian immigrant refugee, there aren’t a lot of ‘back up’ or ‘safety nets’ for us – which can be limiting & intimidating. Working in corporate had the appeal of safety/stability – but no matter what industry or role I was in – even the good ones – it never felt like a perfect fit. Read more>>

Audrey Ra

I started by small business with watercolor in 2017. I had been painting for a year and began posting on Instagram regularly. After a few months of posting, I would receive comments about how I painted this flower or what supplies I’m using. I was happy to share, answer comments, and wrote regular blog posts on my website. Read more>>

Summer Matthews

The biggest risk I ever took was finally choosing myself. After spending most of my teen and adult life chasing success, productivity and thinness, I have chosen to take another path and recover from my eating disorder. Read more>>

Amy Berry

One of the most defining moments of my life was when I lost my mother, who was not only my best friend but also my anchor. Her passing plunged me into a very dark place where I started drinking heavily and neglecting my responsibilities as a wife, mother, and friend. Read more>>

Dr. Shawn Fuqua

Betting on yourself is always a risk. What if you “mess up” or “get it wrong”. Failure is such a hard thing to accept and when you have been divorced twice, you cannot help but to see yourself and ask, “Where did I go wrong?”. The first relationship was not a healthy relationship, so initially I did not see myself as doing anything wrong. Read more>>

Kristi Snyder

Starting my coaching business was definitely a risk I took on myself. I started my career in veterinary medicine in 2008. Within a couple years into practice, it became clear that I was heading towards burnout. While I loved aspects of my job as a veterinarian, I did not love the 50+ hour work week and lack of work / life balance. Read more>>

Christy StCyr-Allen

I thought I would always be a corporate babe, who would move up the corporate ladder or start my own real estate firm. I did everything the way “they” said we should do it. I went got the good grades, graduated with honors, got a scholarship, business degree, corporate job, real estate license… Read more>>

Ramsey Thoms

I believe this is the most important question in an Artists path, especially for me. I grew up an athlete and my whole life was centered around basketball I never once thought of being an artist. Now when I look back on my choices and my life, when I was younger every time I would go see a film I was in this big hurry to come home and I would lock my door and be as quite as possible and I would reenact everything I could remember, especially if it was an action film. Read more>>

Robert Schermeister

“Feel the fear and do it anyway”. That’s the motto we live by because we’ve been taking risks – separately before we met and now together as a small business couple – since our early twenties. Back then, in 2001, we were fresh out of college and flung into the world to go and find success. Read more>>

Ruby Felix

Prior to entering the culinary world, I was in school to become a nurse. Unexpectedly and slowly I became interested in cooking (and dining out frequently). I would come home and recreate dishes from where I had recently dined. I was pretty good at it and my passion for food grew. Read more>>

Megumi Reagan

Ouf. Okay, as much as I’d like to consider myself risk-averse at this stage of life, it might be because I packed in a lot of risk over the past decade. One thing you should know about me: I’m terrified of complacency. I strive to always be learning and growing. Read more>>

Jennifer Seidner

Life is too short and you never know when it will change… so why not be the one making the change? I never wanted to move to california, it was actually my mom’s dying wish. We learned, as she was a patient at the Cancer Treatment Center of America in Goodyear, Arizona, that most patients that “graduate” their treatment are able to live in San Diego and take a short and affordable flight over once a month for treatment or checkups. Read more>>

Leah Lopez

In 2007, I took a leap of faith by relocating from my home state of New Mexico to the bustling city of New York in pursuit of my creative passions. Back in Santa Fe, I was beginning to make a name for myself in the art scene. While I had received training in traditional oil painting from established artists, I was largely self-taught. Read more>>

Devin Kowl

One of the biggest risk I have ever taken was moving to LA two week after I turned 18 years old all on my own. I knew I wanted to pursue a career as professional singer/artist. Sow hew I turned 18 my first thought was how d o I get to LA? Read more>>

Nicolette Myrick

Photography, while a costly pursuit, can lead to an even more expensive venture when turning it into a business. My journey began when my husband presented me with my first DSLR camera, allowing me to dip my toes into the world of photography and art creation. Read more>>

Crisha Bowen

Thank you so much for thinking of me for this opportunity. Taking a risk is not making an uninformed decision. Most people are afraid of risk because the approach is literally throwing themselves to the wind and letting the wind determine the direction in which they go. Read more>>

Kelly Brown

Title: Breaking Generational Curses Being the generational curse breaker of my family meant taking the risk of losing everything. I had to let go of old patterns, habits, and cycles of traditionalism that had plagued my family for decades, even centuries. In many Black families, there’s a tendency to sweep things under the rug and close your eyes to the reality of what’s happening. Read more>>

Chace Rains

It’s a pretty current risk, but the largest one of my career with far and away the largest payoff. Two years ago, I signed up with a company called Edgewater Music Group. They contacted me in November of 2021, but admittedly I didn’t take them seriously at first. Read more>>

Xiaoling Li

I took the risk of continue to invest and pursue the career of a tattooer even when covid happened suddenly and basically shut down all tattoo shops and made my future looked very grim. I trusted in myself and took the risk to just hang on and pursue it anyways. Read more>>

Dylan Marks

Establishing my own practice during the COVID pandemic was a large risk that I took. I decided, that the in-network model of health care was falling short for many patients that I was treating and I felt that I could offer an alternate way to approach physical therapy, fitness, and health. Read more>>

Jessica Feldman

I started my career at a local screen printer while finishing college. That job had taught me so much about graphic design, vector art, business, marketing, and so much more, that about 4 years in I wanted to branch out, learn even more about the craft, and find my “forever job”. Read more>>

Bronwyn Ainsley

I am a teacher with over a decade of experience, teaching in both public and private schools. Towards the end of the school year in 2023, I experienced a situation in my classroom that forever change my mindset as a teacher. Read more>>

Tiara Cohen

I have taken many risks in my life. I personally feel that’s what living life is all about. No matter how much you research or ponder, you will never know 100% that risk you are taking is worth unless you take it. One of the biggest risk I have taken was leaving Fayetteville, N.C. in 2018. Read more>>

Christopher Labine Jr

One of the most significant risks in my artistic career was creating “DICKSCOVERIES” during a uniquely challenging time. I was juggling my college degree, working at my father’s restaurant, “Hangar 7” in Lompoc, California, planning a wedding for an astronaut’s son, and assisting part-time at SpaceX during NASA’s first mission preparations amid COVID. Read more>>

Kayra Touré

One of my greatest strengths is my ability to always see the bigger picture. A risk that I embraced was pursuing a career in modeling. Initially, the question was how far I wanted to take it. Modeling captivated me because of my natural ease with posing and being in front of the camera. Read more>>

Wandaline Joassin

Photography was always a cherished hobby of mine, something I held dear to my heart. While I occasionally dipped my toes into turning it into a business, I never took a significant leap due to my fear of failure. This all changed the end of 2023. Read more>>

Kelly Price

After selling the company I owned and operated in the auto industry for almost 30 years, I learned about an innovative and life-changing treatment to help people who suffer from mental health issues like PTSD, anxiety, depression, ADHD, OCD, hypervigilance and even menopause! Read more>>