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.

Kate Clements

Although there are many risks I could recount, the decision in 2020 to quit my stable job, sell my car, get rid of housing, and move to Nicaragua in the beginning of the pandemic to start a business and buy a hotel probably takes the cake ;) Read more>>

Vanessa Plazola

When I first decided I wanted to switch careers from auditing to massage therapy, I instantly knew that it was my calling. I always wanted to be in a profession where I could help people, however I somehow found myself in a job full of numbers and reports. Although i was grateful to have this opportunity, it was unfulfilling. Read more>>

April Carroll

I have taken a risk on myself. My entire life I have always put other people feelings before mine, why you might ask I couldn’t tell, however I do know that it has something to do with trauma that has happened in my lifetime. Over the years I never understood how and why I reacted the way I do to situations that has absolutely nothing to do with me, but somehow I become the person in the middle. I’m almost like a black sheep. I’m the person that the family brings there troubles and issues and I’m supposed to fix it. Read more>>

Mike Gerbrandt

Understandably, so many people are risk averse. But I’ve always loved risk because I believe it reveals more about ourselves and the world we live in. We all function somewhere on a spectrum between complete order and complete chaos and I like to lean over to the latter. This plays into our games designs and while our players may experience some confusion and bewilderment and certain points in the game, the gratification is that much sweeter when something is solved or utilized. It’s so fun to watch. While it’s not unequivocally true, I really enjoy a one definition I once heard…”chaos is order, yet undeciphered.” Read more>>

Brooke McPheeters

We were born to take risks. But that is not what society wants us to believe. We are here on this planet to remember what we are, how we are and what we can do to make this world a better place. In order to do that, we have to step out of our comfort zone and “be.” Read more>>

Chelsea Drummonds

I highly encourage any and everyone to take a risk. Big or small, a risk can change your life. Being a mother of two and working three jobs I found myself stretched thin. Unable to focus and execute my real passion for fitness. In 2020 I took the risk that changed my world for the best! I threw myself into my business fully and quit my 9-5 job of 10years. I kept a “side hustle” to cover the cost of my business expenses. Read more>>

Patricia Polgar

A couple months before the pandemic hit, I signed and paid for all the documents I needed to start my semester in the Las Vegas studying music business and tech. I was waiting for my Visa interview appointment when the whole world shut down. After almost a year of uncertainty, the embassy opened back up in my home country, and I got my student Visa. I had 7 days to pack everything and move away to start a new life. It was a huge risk to me, nobody knew what the future might bring. Read more>>

Christian de la Torre

“Christian, it’s time to settle down and start building your career. You know people here, you are established, connected, and comfortable.” This is what some of my friends and colleagues said when I quit my job in Colorado, left a great little house, and many of the friends I made in the military. My friends had settled down or were settling into “9-5” job routines, getting married,and having children. Read more>>

Bobby Mertz

I think the biggest risk I ever took was, like many, packing up everything I owned and moving to Nashville to pursue music. Nobody has any guarantees here… One day you’re sitting on top of the world, and the next, you’ve reached your lowest low… It is such a roller coaster, but more so an amazing experience that often goes unexplained…It’s like something everyone chasing the dream here understands, Read more>>

Christina Guzmán

I’m certainly not a stranger to taking risks in life or in business. In fact, many of the risks I’ve taken over the years have changed the trajectory of my life in ways I could have never imagined. The first significant risk I took within the creative space took place over 5 years ago when I was living in California. At the time, I had been doing freelance work as a Photographer and Designer, but after a challenging experience at a brand photoshoot, Read more>>

Mike Karan

My whole life I think I’ve always taken the riskiest route(s). I think that all sprouted from playing sports. I was always taught to just leave it all on the field no matter what the out come, go big or go home. Take the risk no matter what. So I did just that. I loved playing football and honestly if I could today would do I’d do it in a heart beat. I tried my hand in being a professional giving my younger years away to it. Read more>>

Sydney Crane

The best risk I have ever taken was quitting my job and investing in myself and my business fully and whole heartedly. It was the best thing I could have ever done. In 2018, I had planned a big trip to visit my hometown in Alaska and decided to really quit my job on that very trip. I’ll never forget being on the plane on the way there. I had a 9 hour flight to think about a lot of things. I had faced a lot of changes in my personal life that month. Read more>>

Kyra Stayton

Taking a risk is a leap of faith on doing something you can’t see or touch and lastly don’t know what will the ending be it’s scary, But for some reason you still do it because you know it will help you grow as a person and applying the lessons to keep going. I took plenty of risk which began Jun 8 2018 going to a college program right after high school . Read more>>

Latonya Brabham

The biggest risk I took was starting my business while working a full-time job. It literally felt like jumping off a diving board in the middle of the ocean. Once I finally decided to showcase my business I had to plan the grand opening of my small business so I started looking for venues to host my first pop-up event. I nearly drove myself crazy trying to find the perfect space when a close friend said “why not use your own backyard it’s big enough and just call it a garden pop-up?” Read more>>

Septimius The Great

Being a music artist, actor and model – was all created by taking risk. Risk meaning I had no knowledge or experience but has a feeling/passion to be a creative. Read more>>

Meg Stolt

My work encompasses getting people to stretch their limits, and stepping out of their comfort zones. Endurance sports is indeed learning to be comfortable with the uncomfortable. In this, I have pretty much been a risk taker throughout my life, from jumping off the railroad bridge in Pennsylvania into the Delaware River, to moving across country not knowing a sole. The most recent risk was the catapult from Cape Cod, Massachusetts to Houston, Texas. It seems. Read more>>

Xhico

Taking risks is so vital for a creative. Really in any field, risk can set you apart from others and help you develop into your unique self. My first risk was being 18 and wanting to leave my rural countryside for the big city and work for Warner Bros. Records as a designer. I had very little support for my dreams from others in my town, but it was a risk I took on myself, and that first risk paid off in dividends. Read more>>

Joan Montreuil

I’ve taken several risks in my life, i guess it’s in my nature to not fear the unseen but to focus on the rewarding outcomes. Perusing the world of filmmaking is a great risk if the goal is to have a stable career. But the point of any art form is to do it because it enriches your soul, not because it is a route to security. Read more>>

Heart Boner

Yes, well it changes quite a bit from working on canvas to skin. You suddenly feel this massive responsability that makes your hands shake when you do your first tattoos. Is one of the obstacles you have to overcome when you start tattooing. I could just draw on paper, why to go through all this trouble right? But the experience of tattooing is really food for my soul. Read more>>

Adriana Banda

It all began when I was given the challenge to do something I had never done, which was balloon styling. I took the challenge and succeeded. I created balloon work that brought nothing but traffic my way of people wanting to have me do balloon work for them. I then thought to myself, was this something I could pursue and quit my part time job? Would this take off the way I want it to? I then decided, yes. Was it risky? Of course. Read more>>

Nicole Pryor Dernersesian

The biggest risk I ever took was starting my business in the first place. I only started it because, as an actor, I was struggling to find television and film representation. So… I started my own talent agency to help move my acting career along by representing myself. And because my friends were having the same challenges, I decided to bring 12 friends along for the ride. It was REALLY scary because I had never worked at a talent agency. Read more>>

Charles Fossett-Lee

My whole life has been about taking risks. When I was 15, my parents moved to the city, and I stayed in Fairfield, which I considered my hometown. It’s where I did a lot growing up and finding my place in the world. It wasn’t that my parent just left me; no, they wanted me to go, but I have always been strong-willed. Also, my Mother raised me to be a very independent person. So if I believed I could do it, I would do it. I started my leap of faith with my risk-taking. Read more>>

Gabe Shaddow

Let me start by saying this. Life is a risk. Driving on the freeway is a risk. We risk our lives every day without noticing… Why wouldn’t you want to risk a 9-5 to have a dream job that you created? Anything is possible, but people don’t believe that. Once you really dive in and understand that this world was built by people like you and me, it should alter the way you see things. Anywho, it’s much easier said than done. I’m not going to lie, it’s really tough, but I love it. I think, no, yeah, over a 9-5 any day… Read more>>

Jennifer van Heeckeren

Why take a risk? Great question! Honestly, I think that taking risks are where the “good stuff” is. For me, my biggest risks have been two things – living unabashedly as an artist and love. There’s actually something I read recently and I can’t stop thinking about it. “Living less like a noun and more like a verb.” Read more>>

Brooke Hinders

When talking about taking risks in the fitness industry, there are truly so many avenues we could discuss. It can be risky to try lifting a new weight for the first time. It can be risky to push yourself to a new speed on a treadmill. For most though, just walking through the doors of the gym is a risk. Read more>>

Sandy Duarte

Taking a risk I think is the one big steps or key foundations for being an artist, a creative of any form, because of the vulnerability and strength that it requires in sharing ideas that are personal to you. I think that pursuing your own voice in any creative area of life is a risk. You take that risk, that chance that what you believe in and love so much will either be well received or rejected. As a creative, the road is paved with a lot of rejection, and not all rejection is “bad”. It is part of the process of trying to sell an idea and seeing where it lands. Also some rejection for a project actually opens a door for other interest sparked in your work. Read more>>

Janet Weed Beaver Beaver

I’ve always worked in an art related environment. 20 years ago I took the leap and became a full time artist. When I attended art school we didn’t get much career advice. The concentration was on creating and developing works of art. I gradually worked on the business side of promoting sales while still creating my art. It takes time and patience but I am proud of what I have accomplished. Read more>>

Nick Winn

The first big risk I took was dropping out of Art college when I was 21. Cartoon Network contacted me about an internship while I was in my 3rd year and since I was going to school in San Francisco, I knew taking the job meant dropping out and possibly not finishing my degree. I decided to take that risk knowing that schooling is never going to go anywhere, but an opportunity to work at a company you’ve been dreaming about doesn’t come often. Read more>>

Alexis Harris

My biggest risk so far has been deciding to start my own business. I got out of the army during the height of COVID with no idea what I really wanted to do. It was actually my husband that influenced my career path. I’d thought that I had to go straight to work finding a “sensible” job. Read more>>

Jay Pineda

I used to work at a corporate job, but I always knew that I wanted to start my own business. After years of working my side gig on the side, I was still feeling unfulfilled because I knew I had to go into my 9-5. It was a great job but it just wasn’t my purpose. I finally made the decision to quit my job and pursue my side business full-time. That is when Video Cartel grew bigger a lot quicker than I expected. Read more>>

Casey Mensing

As a creative, risk-taking is an essential element. No matter what form your creative act takes, you must push yourself out of your comfort zone to develop and evolve as an artist. Then if you want to pursue a career in a creative field, that’s a massive risk because there is little financial reward and almost no compensation for the majority. In a money-driven society such as the one we live in, that seems like a crazy proposition. So, when someone decides to turn their artistic vocation into a career, you know they’re willing to take a personal risk. Read more>>

Brett Schieber

One risk I took that really made a big impact on my life was when I was offered a job as a music director for a musical theatre show. I was in Atlanta taking classes at the university, but chose to leave to take this job. They paid for me to drive across the country to meet them at Glacier Park in MT. It was an amazing adventure to drive across the country by myself, see such a beautiful place, & be challenged by learning so much music in such a short amount of time. I am lucky that I got that chance of a lifetime and am so glad that I took that job. Read more>>

Nina Boodhansingh

As humans, it’s easy for us to get wrapped up in the hustle and bustle of everyday life. We are absorbed in everything except dedicating time for ourselves. Time for reflection and taking care of our mental health is essential in today’s world. Work the overtime, run the dog to the vet, take the kids to soccer practice, hit the gym, stay at work to perfect a project, scroll through social media until we are numb. Rinse. Repeat. Yes, a lot of these things are our responsibilities and need to be done, but when was the last time we stopped to think about our passions? Read more>>

Shyam Thandullu

As a jazz combo comprised of high schoolers, it was definitely a risk to perform in public with my group. After all, we were all teenagers, and jazz isn’t exactly the most popular genre of music. But we had a passion for jazz, and we wanted to share that with others. We spent countless hours honing our skills, perfecting our repertoire, and building a tight-knit bond that only comes from creating music together. Read more>>

Megan Gallagher

I was 35 years old, working in the corporate world of media, doing everything i had set out to do early on in my career of choice. I was making good money, had all the snazzy “Adult” things you get with a corporate career, on paper it all looked great. But, it felt awful. It was a time of massive change in the industry, uncertainty of job security, and I was deep in the middle of anxiety wondering if at the end of the day, I would still have a job. Read more>>

Rhonda Heady

Taking a risk, leaving a well paid pharmaceutical sales job to start my own pharmaceutical company and work for myself. Leaving the guaranteed money, health insurance and everything else to be completely independent of no one other than myself Completely worth it Read more>>

Khalil Perry

Since 2015, I have taken on the risk of investing effort, time, finances and more than you can imagine to build up my media production company in NYC. We specialize in documentaries and promo videos about a variety of entrepreneurs, influencers and community leaders, mostly based in NYC. We have also been able to build up a medium sized following via social media content that provides mini-docs, archival content and history from around NYC’s five boroughs. Read more>>

Tracy Borreson

I’ve heard that people won’t take a risk until it’s more uncomfortable to stay where you are. This is definitely true for me. When I created my business, I thought it would always be something I did on the side. An outlet for my desire to see people grow and succeed. But after I went back to work after having my son – he’s now 5 – work just didn’t feel the same. Which was confusing for me…because when I left, I LOVED my job. But when I went back, all I could think about was how, as a time trade, I would rather spend time with my son than doing my VP, Sales & Marketing job. Read more>>

Celeste gonzalez / Celesthestylist

Life is constantly changing and as a business owner and educator to beauty pros, one of the most common struggles I see is being willing to pivot and take risks for our growth. Growth and taking risks can seem challenging so today wanted to share ways that taking risks can help grow your business and change your life in amazing ways. Read more>>

Kay Lee

I’ve always loved to paint and create artwork on a smaller and personal scale, as in on a canvas. Last year, I was asked to participate in DC Art All Night and to paint a mural live. I was excited about the idea and totally freaked out at the same time. I would be surrounded by the community and standing beside other artists that I considered “top notch muralists”. Read more>>

Jet Hatu

I spent 7 years in the corporate world. During that time was highly successful in building a team and leading the organization to millions of dollars in year over year growth. I loved training my team, I loved the sales process, I loved the business, until I started my own business in 2022 and began finding the freedom to be more creative and on my own time. Read more>>

Scharmaine Lawson

I took a risk on becoming a children’s book author. I desired to see multi-cultural children representation in kid literature that simultaneously introduced them to the amazing world of Nursing. This did not exist. So, I created it. Read more>>

McKenzie Parrott

It’s not much of a story (as its just starting) but leaving my corporate job a few weeks ago to pursue art & Parrott Paints full time has been the biggest risk I’ve taken. As someone who has always held a love for color and creative expression, it was a difficult decision to leave the security of my job. However, I knew I wanted to dedicate myself fully to my passion for art and explore all the possibilities it has to offer. So far the journey has been challenging, but incredibly fulfilling. Read more>>

Diana Caruso

Today I am sharing this article with you, because for some time now I have understood that the best way to live life is to live intentionally. “Risk is a step into the unknown, but also an immersion into a possible unknown success”, Lahcen Haddad. History has taught us that those who dare nothing have nothing. In fact, history unfolds because there are men and women who take risks, try new things, think outside the box, challenge themselves and navigate the unknown. As Helen Keller said, “life is a bold adventure or nothing.” Read more>>