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.

Monica Johnson

Sometimes the best risk in life is the one you take with a leap of faith not knowing where you’re going to land but trusting that the outcome is far greater than not taking that risk at all. The risk that I took several years ago was the momentum I needed to get to where I am today. Read more>>

Patricia Rae

What does it mean to take a creative risk? Everything. I have always been a creative person, whether I was painting, acting, or dancing in my living-room. It brings me joy. I feel empty when I am not making art, in some form or another. But, I truly believe, that we are all creative beings at our core. We were born to create! Name a profession, that does not benefit from your creative thought process. Read more>>

David Wilkinson

18 years ago, I left a stable job with my wife and 3 young children to move to Nashville to pursue being a videographer/storyteller. To get my foot in the door, I took an unpaid internship for a film company that offered the occasional $100 payday for any given shoot. My first shoot was as a production assistant for a country music video, in a warehouse, next to the stadium where the Titans play. Read more>>

Chanell Sinkfield

After many years in a corporate setting, I just became so sick and so tired of constantly being away from my family and the lack of time I left in the day to spend with them. I literally dreamed of a day where I could own my own business, and built an incredible empire based on my dedication and my commitment to succeed. I dreamt of all this, PLUS I held tight to my core desire to truly serve and build connections with people. Read more>>

Marc Kray & John Metcalf N/A

In 2020, we took a huge risk. At that time, we were both self employed but looking for other job possibilities. We had been friends since 2012 and had formed a band together that lasted 6 years. We both had previous experience with woodworking and were building some projects on our own. Our idea began as a whim but after a few ‘business’ meetings over coffees and beers, it blossomed into a full-fledged effort to fill Marc’s existing workshop with tools. Read more>>

Shawnick Rodriguez

Some times in life it is important to take risk. Especially, in your gift or as I like to call it, the calling in of your life.. As for me, taking a risk means betting on myself. Trying something that has never been done in my life knowing the possibility of failing or succeeding but if there is anything I learned from taking a risk, its so worth every single tear I shed. Read more>>

Melisa Mitchell

My entire business has been a series of risks–a succession of moments where I thought about what I want and bet on myself instead of what seemed to make sense. Despite being a full-time high school teacher (a job that is often a 7-day-a-week job), I began to build my practice and client base. Despite being busy and working 7 days a week, I added an additional day of availability to see clients. Read more>>

Ursula Duffy

Prior to 2017, my life path was what one could consider “traditional”. I went to college, earned a bachelor’s degree and worked in professional/corporate jobs for over 15 years. I worked as a certified professional Geospatial Scientist mapping for local and federal government. I was a team leader in every position specializing in organizing, teaching, training and managing projects. Read more>>

Cg Prince

Coming from a rough neighborhood managed to risk it all by choosing my own path and I end up doing a bid that cost me a quarter of my life. Read more>>

Nika Leverett

I took a pretty big risk following this dream of being a full time artist. While pursuing this, I was working as an instructor with United Health Group for about 6 years. I was creating my art any chance I got. lol. As a facilitator, there were times when my trainees would self study, during those times, I would be painting. Needless to say, I was phasing out to be a full time artist but we become so dependent on a paycheck that stepping out can seem so scary or so far away. Read more>>

Angela Thompson

In 2015 I was exhausted from being overworked and underpaid. I was tired!!! I said to myself there have to be more social work opportunities available with better pay and less stress. I searched the internet diligently until I came across Travel Social Work. I was so intrigued by the idea of travel social work because I always wanted to travel but did not think social work would afford me such an opportunity. Read more>>

Demione Louis

One of life’s most challenging obstacles can be the end of a meaningful relationship. Particularly, separation or divorce raises a person’s chance for unpleasant psychological symptoms. I lost my wife, my career, my children, and my way of life. This gap compelled me to seek God’s presence, who led me to my music. Since music was the one thing I could control at the time, I risked everything for it. Read more>>

Kim Meagher

I had worked in corporate since I was 19 years old. During my time at Intel Corporation, I found out about the plight of American horses being sent to slaughter. At that time, roughly 100,000 horses every year were sent to slaughterhouses to supply the demand for horse meat in other countries. I had just purchased a small ranch in the heart of Gilbert, Arizona. I looked the old barn, counted the stalls and said, “I can help 11.” I created Wildhorse Ranch Rescue. That was in 1995, 28 years ago and over 1000 rescued animals ago. Read more>>

Tara Durnbaugh

One of the biggest risks i’ve taken is starting my business. The idea was planted as a small seed in my head while in beauty school, as some of my classmates were already business owners + had experience in the business world. One woman in particular i’ll never forget, her name we will call S. Read more>>

Dr. Alex Osorio

My official opening day was also the first day of the mandatory lockdown in Miami. I had all these plans to open my doors and build a business from scratch and we were forced to close just like other businesses because of the pandemic. It was an uncertain time since nobody wanted to leave their homes. There was a lot of confusion with local officials as to what could remain open and how to safely do so. Read more>>

Edie Sohigian

After my multiple sclerosis (MS) diagnosis in 2015, I was definitely in denial. I had gone numb all over my body along with some other symptoms. Following treatment, the symptoms subsided and I put MS in the back of my mind. I didn’t want to face it. Read more>>

Matthew J. Sánchez

A major risk we took at Matteo Parfums was to debut our first product, Celadawn, during the pandemic in Fall 2020. Considering we are a fine fragrance house, launching products at this time was almost insane because perfumes and colognes are desired small luxuries that people like to smell in person. And as we all remember, no one was leaving their homes at this time; there were virtually no events, remote work was the new norm, and retail shopping took a major hit as online shopping took over. Read more>>

Jennifer Ogden

After I graduated from Penn State, I worked for a chemical company in Philadelphia. At the age of 23, the company offered me a promotion to manage clients in the western US, western Canada, and Mexico, and it required me to move to California. I was fortunate to have the support of a great manager and employer, but I had to decide to move by myself to the west coast. Looking back on it now, Read more>>

Jason Dennen

I took up skydiving as a way to challenge myself and as a way to relieve stress from a corporate job where I was working 60-70 hours a week for years at a time with very few breaks or vacation time. On my 327th jump I was coming in for a landing and a huge wind gust hit me from behind and picked me up in my harness and slammed me violently forward through a cattle fence and into the side of an airplane hangar going 30 mph. Read more>>

Rhonda Eldridge

We began in 2017 as a program of a local rescue. After 1 year, the rescue decided we had grown to big for them to support us. In May of 2018 the volunteers incorporated on our own. Over the years we have created many programs. *We created a free Food Pantry so we could deliver food and supplies. Read more>>

Samantha Dorisca

This is a timely question. Over the years, I have taken quite a few risks that have paid off. In college, I switched career paths. My original goal was to be a lawyer, but I pivoted my focus to be a writer and pursue photography. In recent years, I have scaled my passion for photography into an expanded business while maintaining my position as a journalist. Read more>>

Lisa Morton

As a woman writer who has been selling for over thirty years (mainly in the horror genre), I am frequently asked what one piece of advice I would give to newer women writers, and my answer is this: BE BOLD. As women, we are often reluctant to step forward, to submit our work, to ask editors to read us, or to include anything potentially controversial in our work. Some of my best sales have come because I took the initiative: Read more>>

Kevin Mellon

I was living in Kansas City, MO. in 2011, working on comic books for Image Comics and various other indie companies, also watching a lot of TV while I worked. One of my favorite shows as a cartoon on FX named “Archer.” I was a fan of Floyd County (nee 70/30 Productions) and their previous show “Frisky Dingo”, so I was all aboard the Archer train before it even aired. Read more>>

Brandy/Crystal Johnson?Pettitt

Opening The Rabbit Hole was a huge risk for us both. When we had the idea to open a store it was about keeping access to dance supplies due to the closure of a 35-year-old dance academy. With it went the only dance supply for close to 100 miles. With five kids between us in dance we knew we were going to be facing challenges getting the things we needed for our kids’ Read more>>

Babette de Jongh

Maybe it’s my anxiety talking, but everything I do feels risky. Living in a constant state of low-level freak-out is strangely liberating. When making an innocuous reply to a random comment on Facebook feels like standing on the edge of a cliff, writing and publishing a book doesn’t feel so overwhelming. Read more>>

Quynh Le

Pursuing music professionally is the riskiest thing anyone can do, but add a new business on top of that, it’s almost career suicide. If I hadn’t taken those risks in my life, I would not be where I am today, a music educator, business owner, and pianist. Read more>>

Angela K. Durden

Divorcing my husband after 32 years of marriage and stepping out on my own was a huge risk. But having had time to think about how I would do that, good planning took some of the fear out. I chose to divorce because his negativity (among other things you can probably guess at) was never going to change. My creativity had to be hidden from him. I tell people, “I cheated on my husband…with Creativity.” I look at pictures of myself from that time and can see the smile pasted on under eyes that clearly showed stress. Read more>>

Savanna Cummings

One of the biggest risks I’ve taken was dropping out of college to pursue my music career full time. Growing up in a musical household, only added fuel to the fire when it came to my dream of being an artist/musician. I’ve always known that this is what I wanted to do with my life and that has never changed. Read more>>

Holly Jones

Listening to my intuition to downsize my 20+ year physical therapy private practice to one day a week, treating patients in my home, and working on my music the rest of the week. Although this occurred in June 2020, I made this decision to close my office practice and begin a home practice prior to Covid. It began with reading a passage in a book that spoke of the necessity of rest. Read more>>

Alexander Johnson

When I first started as a YouTuber, I did a lot of reaction videos. I thought of myself as funny, so it made sense to take other people’s content and make it unique to myself. Reaction videos were also an easy way to generate timely content. However, after a while, I realized that the videos I was putting out weren’t authentic to me. I was doing “try not to laugh” videos, but I didn’t find them funny at all. I knew I had to try something new. Read more>>

Frantinique Finn

I recently planned my own Comedy Showcase this year for Cinco De Mayo! I found the venue, DJ and even designed the flyer. I had to take the risk of the event not doing well but I thank God that it was success fun and a lot of fun! It left me feeling inspired and like I can accomplish anything I put my mind too. Read more>>

Savannah Rose Johnson, BA, CLC, RTT.P

When it comes to risk-taking, it’s less about the risk itself and more about how we move through any fear, doubt, or critique that arises in the process. Anything worth doing often contains some element of risk; any fear or discomfort experienced is actually valuable self-exploration data and information. Fear shows us our perceived limitations. Fear also shows us how important something is to us. It’s okay if we feel fear and it’s normal. Read more>>

Amina Touray

I quit my job and gave up my life in Europe to come to the USA to pursue my dream of working professionally as a photographer and artist. The most significant risk I’ve taken was to move to another country by myself, without knowing anyone or having any associations with it. I had faith I was led by, so I was not necessarily scared. It was always a calling, why it felt so natural when I did it. Read more>>

Alina Avellaneda

As a young, passionate entrepreneur and digital creator, taking risks or starting projects has never been a simple task, but does get easier throughout the years of pushing those boundaries and allowing yourself to grow as a creative. In order to take risks, we must put ourselves through situations that make us feel nervous, Read more>>

Weslee Kate

Risk taking is something that I feel like gets looked at a bit sideways sometimes. In my perspective everything and anything you do in life is inherently risky. It all has consequences; the question is simply which ones are worth over riding fear. From what I have learned fear is your best friend, it is always by your side, Read more>>

Deja Patterson

When I was 21 years old in my senior year of undergraduate studies, I saw a flyer advertising a museum fellowship at The Louis Armstrong House Museum. I was living in Mississippi at the time! Since the search was spread to HBCUs (historically black colleges and universities) I thought I didn’t stand a chance to be chosen for the fellowship. With motivation from my partner at the time, I applied. Read more>>

Jastin Artis

The most recent risk I took was in the summer of 2019 after losing my job that I resigned from and losing my son at 22 weeks – all at the same time. So, it’s March 2019 and I started a new job as a project manager and editor. After doing a great job after six months they wanted me to continue and offered me another six-month contract. I was thrilled and very excited because I’m thinking I’m finally able to continue a contract for the long term. Read more>>

Richard Arguelles

Risks aint nothing new to me and to be honest I wouldn’t even know where to begin on how to “properly take a risk”. Lemme put it like this, from the moment we wake up in the morning to the time we go to bed, we’re constantly faced with day to day choices that could change our lives forever. Some are small risks that we can live with if we mess up, while others are those life changing ones. Read more>>

Emmanuel Simms

In 2021, I was at a significant crossroads in my life. For more than a decade, I was immersed in academia and fraternity life as a member of Phi Beta Sigma, Fraternity Incorporated. and honor society inductee for political science, while also pursuing dual master’s degrees in teaching, and clinical mental health and rehabilitation counseling. Yet, despite these accomplishments, a piece of the puzzle was missing. Read more>>

Marisa Nikole

opportunity that we had to take at the time. He ended up moving to Colorado first, for a few months, to try to find us a house and save for a deposit to move in. I stayed back in California and packed up our entire home and as soon as we could, he came back to California and we both drove out to Colorado together with our two dogs and a huge uhaul with all of our things in it. Read more>>