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.

Terry Tyler

Something no one tells you is that you have to fund yourself when you’re starting out.
I had to sell my car in the university to be able to afford to travel overseas for the first time to kickstart my modelling career.

Yeah,
I think it’s worth it to take a risk. The whole time I left home and my family behind to figure out a career I knew nothing about and I had to carve a path for myself, In the beginning, you know it’s kind of scary, but at the end of the day, all we have is hope and we are just hoping that it works out one day because you hear a about lot of people who started and didn’t really end too well. Read more>>

JT Goethe

There are many risked I’ve taken in my life, but there’s really only one that completely changed my life. I had a very different life prior to me becoming a Deadpool cosplayer and finally finding work I can be happy doing with Habitat for Humanity. I had numerous jobs in many different fields, from the handbag and jewelry section at Macy’s to oilfield work in North Dakota, I dipped my toes in everything I could. Through those years, especially the oil years, I began drinking more and more, to the point I became dependent on it. I kept losing jobs because I couldn’t function without it. I got myself in trouble and hit rock bottom. Read more>>

Joe Buckley

I suppose I was too young and dumb at the time to care, but heading down to Nashville after college without a job, any connections, and nothing but lyrics in my pocket and a guitar on my back was nothing short of reckless. But sometimes I think the reckless and restless fling ourselves into the chaos of irresponsibility not for the sake of absurdity, but for the sake of challenging ourselves to navigate seemingly impossible odds. It’s knowing that you’ll likely fail, but also knowing that for some – your idols, your heroes – the risk paid off to the tune of a lifetime of adoration and financial success. But they, like any artist, simply started by taking a risk against incalculable and improbable odds. Read more>>

Jaye Skye

The ultimate risk that I have taken was moving to California. I moved here back in July 2019 without even visiting the state. I’ve always had dreams of being an entertainer and actor. What better place to be than LA?

Moving from a small town in North Carolina to a big ocean like LA was a true risk. Not knowing anyone, besides my 2 friends who I movedd here with. I have always been a care taker and made sure that my family and friends were taken care of. But neglecting my desires and needs wasn’t fair to myself. Read more>>

Jean Brannon

I was only eleven when my cautious and careful mother died, leaving my loving dad to step up in ways he never dreamed in order to raise two daughters on his own. My mom always made running a household while doing banking and bookkeeping for my dad’s small business seem effortless, but none of us were prepared to do any of it. Fortunately, my dad’s humor got us through all the burned meals and bleached laundry failures and big, heavy sadness. I learned from him that being willing to try new things – and being willing to laugh if it all went sideways – was a lot more fun than my mom’s way of moving safely toward death. Read more>>

Oluwaseyi Tomori

In 2019, at 25 years old, I decided to leave my hometown area of NYC and take the biggest risk of my life — stepping into the unknown to find my direction. I moved to Kansas City to stay with a close friend, recenter, and rebuild after feeling stuck financially, emotionally, and professionally. A year later, after my car was repossessed at the start of the pandemic, I was at a crossroads: return to NYC or keep pushing into new territory. Read more>>

Allison Termine

I seem to continue to take a risk daily. For me being an artist has no certainty, period and paradoxically very risky. Most likely as a pre-teen I knew I wasn’t like most people around me. Definitely trying to “fit in” took years of my life, some unsurmountable efforts, several slack jaw moments, more than I can count moments that helped shape who I’m today. I felt more comfort in atmospheres that claimed it’s own space, the kind that were, are multi-sensory. Even though I was often on the outer rim-a bit of a shadow lurker (due to low self esteem) I took those risks, and steered into the ripples those risks created for me. Read more>>

Lori Riviere

Starting The Riviere Agency was the biggest risk I’ve ever taken, but also the most rewarding. At the time, I was living between Miami and NYC, working full-time as a litigation attorney. From the outside, it looked like I had it all together, but I felt creatively stifled and out of place in a male-dominated field where I didn’t feel seen. Read more>>

Harapan Hope Limansah

I come from a strictly working-class family. My Appalachian mother waited tables with a 9th grade education her entire life and my father, an immigrant from Indonesia, has worked his entire life as a car mechanic. I was the first person in my entire family to attend and finish college. Thankfully, about 75% of my undergraduate education (pre-art therapy track: BA in studio art with a minor in psychology) was funded by various scholarships and I did not have to take out an exorbitant amount of student loans to fund my education. And despite facing several mental health setbacks along the way (including two mental health medical withdrawals from the university), I was able to graduate only a semester late and with high honors. Read more>>

Valeriia Kochnieva

Each training session and the graduation of a new lash extension or lash lift specialist is a huge responsibility and a risk, because I am responsible not only to the model who trusts me enough to come to a practice session with someone holding sharp tweezers and working with glue near their eyes for the first time in their life. I also take on significant risks when training these women. Their future depends on me — on how much they will fall in love with the profession, and how easy the learning process will be for them. It depends on me whether they will continue working in this field or leave the course feeling tired and saying that it’s not for them. Read more>>

Ivanna

One of the biggest risks I’ve taken was moving to Los Angeles from Perth, Western Australia at the beginning of 2022, right after the peak of the pandemic, to pursue my career as a fashion stylist. I had secured my U.S. work visa during Covid, which felt like a win in itself, but the timing was daunting.

The industry was still recovering, the city wasn’t the same LA I had visited pre-Covid, and I knew I’d be starting completely from scratch in a new country with no safety net. Read more>>

Dana Madej

One of the boldest decisions I’ve ever made was stepping into my current role as Shelter Supervisor. I never planned to be the boss, and honestly, I’d already turned down the opportunity a couple times in the past. I have worked in the animal field since I was 17 and while the majority of that time I was in the veterinary industry, my heart was yearning to help in a different way.
I took on a position at the local county animal shelter as a receptionist. At that time, we were located in a decades old building that could only hold a handful of animals and the number of staff and amount of elbow room was just as lacking. I loved that job, and I could feel the impact we were making every day. Unfortunately, Covid hit just a couple months after I started and my finances changed. Read more>>

Momodou Saho

Risk-taking has been a constant in my life. Leaving The Gambia for the UK was my first big leap: new country, new culture, chasing a dream with no guarantees. After a few years, I earned a Degree of Arts in Professional Culinary and landed a position at The Grove Hotel in Watford. However, I chose to return home to open my own business, another gamble that taught me what it means to create something from the ground up. Then I left it all behind again to start over in the United States, rebuilding my career from scratch. Read more>>

Kevin Unger

For me, the biggest risk wasn’t one dramatic leap. It was slowly letting go of a version of my business that looked successful on the surface, but didn’t reflect the kind of experience I wanted to give my couples.

I’d been photographing weddings full time for years. I was busy, bookings were steady, and clients were happy. But over time I started to feel like something was missing. I wanted more space to tune in, to slow down, and to give people something deeper than just beautiful photos. I wanted to create a calm, meaningful experience that helped couples feel safe, seen, and truly present on their wedding day. Read more>>

Aditi Heins

I had been an art director at an in-house creative department for 6 years, while continuously spending hours (on weekends and evenings after coming home) to grow my side hustle. I started my journey into freelance on the side in 2017 by taking on projects from small business owners in Okc – t-shirt designs, beer label designs, logo/branding etc. I even taught lettering workshops all across the state and had the amazing opportunity to teach a group of kids at Cooper Hewitt Design Museum in NYC in the summer of 2018. Read more>>

Erin Orcutt

One of the biggest risks I have ever taken was about a year ago when I left my stable 9-5 job to pursue acting full time.

Some backstory…I have always known I wanted to act. I went to Pace in New York City, earned my BFA in acting for film, TV, voiceover, and commercial, and thought I would dive right in after graduation. But I graduated around the pandemic and was also dealing with some personal and health challenges at the time, so the timing just wasn’t right for me and I set it aside for a while. Read more>>