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.

Tony Shi

I would say the biggest risk I ever took was quitting my stable job and pursuing my passion for filmmaking. I had studied architecture in my undergraduate program. I would say I was quite good at it, but something was missing. In 2017 I was working full time at an architecture firm in San Francisco. I was making good money, and I was living quite comfortably. But something still felt missing. I had secretly (without telling my employers) applied for film school twice. And twice I failed. So in the summer of 2017 I quit my job, went into a semi-monastic solitude at my parents home for 4 months, and devoted that time to seriously considering my application. I knew it was going to be my last try. Read more>>

Greg Berman

I’ve come to realize that life, like gambling, is all about which risks you do or don’t take. It’s not about whether to take risks or not, it’s which ones you can bet on. To live a risk-free life is to live a life not lived. What else are you doing? If everything is a sure thing, then nothing gets to unfold, and I live for that moment. I think that’s what got me into stand up comedy. It’s such a risk. I was a magician before that, even bigger risk. You could do 30 minutes of BRILLIANT magic, and mess up 1 time and that’s the only thing the audience will remember. It’s unforgiving. So is stand up, and that’s why the stakes are so high, and that’s why I love it. Read More>>

Paola Diaz

In a world where stability often reigns supreme, my path to success took an unexpected turn. This is my story, a tale of resilience and determination, where I transformed a layoff from a top Fortune 500 company into the catalyst for my entrepreneurial journey with my swimwear brand, Aqua Intima (“intimates for the water”) . I can still remember the day vividly. The sun was shining, but my world seemed to darken as I received the news of my layoff from a prestigious Fortune 500 company. Although I was a top performer, the whole department was being shut down so it was out of my control. The initial shock and uncertainty were overwhelming, but I chose to see a silver lining in the situation. Read more>>

Sarah English

When I first moved to L.A from Chicago back in 2015, I worked at a commission based salon that was an extremely, toxic environment. It was so bad, that I quit without having another job lined up. After leaving, I hopped around & struggled for a couple more months until I got an offer from an acquaintance to open a salon suite together. Without any hesitation, I said Yes & we started planning our opening. I barely had any clients, I could count them on one hand. But I wanted so bad to be back in a stable work environment, so I took a huge risk, & busted hard to make it all happen to succeed. All I needed to do was pay my weekly rent. Profiting would come later. Read more>>

Tonita B

The biggest risk I ever took was leaving my six figure career after getting released from Federal Prison and starting my own business. Everyone said I should have held on to my job as it was a blessing for a “Felon” to be in such a high position working for a Government HMO. I considered all those opinions but I knew what was IN me was greater than what the world saw. I knew that I was not purposed to make others wealthy, but build wealth for myself. Betting on me and taking a risk by doing what was in my heart to do has paid off greatly for me. I am a serial entrepreneur with successful businesses. Do I miss my regular income, hell yes, but I would not do it any other way. No regrets. Read more>>

Shayna Rattler

I am in the faith based space but I know main stream America needs the principles I teach. I speak and write quite a bit and most of the time the organizations I speak and write for want me to “universalize” my message or make it about purpose instead of the destiny God has ordained for each of us. I was given the opportunity to submit an article for a well-known publication and per usual their request was for me to remove any trace of God from the article. I told my point of contact her request was in complete contradiction to the assignment on my life and I asked her to submit my article to the editor in my original words. Read more>>

Keder LeBeau

Since a very young age I drew comics and I could never get it out of my head. However, since then I had to start pursuing the degree I studied in design, moving away from my original goal and although I continued feeding my social networks with illustrations, I still remained very far from the original goal. A few years later I received my first proposal to draw a comic. Without giving it a second thought, I accepted it, the problem was that I still kept my job as a designer and I couldn’t dedicate the time it deserves. A month later I had to make the important decision to abandon my job as a designer and dedicate myself 100% to my initial goal: Drawing comics. Read more>>

Carrie Freitas

Starting my own PR consulting business in my mid-twenties seemed crazy to a lot of people. It seemed like the natural choice for me, though, even though I’d only been at big agencies for four years after college. I knew that staying at an agency wouldn’t satisfy me — I couldn’t get the personal and professional growth and evolution I wanted in that environment and I had no time for the politics. I was looking for creative freedom and the ability to be in alignment with my values of authenticity and transparency. I also wanted to cultivate deeper, more collaborative relationships with clients. Even though I knew it was the right move for me, I was nervous as working from home wasn’t really a “thing” yet – this was the mid 1990s – and I didn’t have a specific business plan. Read more>>

Gwendolyn Osborne

Taking the risk of leaving one career for another later in life. I left Price is Right with no guarantees. Just my intuition, grit and gratitude! I’m so glad I did! Read more>>

Grace Lim

According to my mom, she claims that I spent a lot of time tinkering on the piano, trying to copy something I just heard. Maybe I was naturally inclined to music, or maybe I felt pressured to continue playing; maybe a combination of both. My parents enrolled me in piano lessons at the age of six, and before I knew it, I was already in college pursuing a double major in piano performance and music theory. Read more>>

Salonica Hunter

Moving to Los Angeles for an unpaid internship was the biggest risk I’ve taken in my life so far. In December of 2019, I received the call that I’d been accepted into the MACRO Spring Internship class. Two weeks later, I packed all of my belongings and moved from Gainesville, Florida to Inglewood, California where I’d rent a room from a friend of a friend I’d met the summer prior. I had no idea that two months after arriving in Los Angeles, the world would completely shut down. Read more>>

Don Cody

I think I take a risk on myself for every project I put out with my name on it. Once it’s out there, it’s out there forever. It could be good or it can be bad, and the internet is very unforgiving. That’s why it is extremely important to me to improve each and every project. So sure, maybe my music didn’t sound too hot a couple of years ago, but it doesn’t even make it into the same conversations to what I’m putting out now. I just want that to always be a recycle and repeat method moving forward. Read more>>

Jim Struve

Most of my adult life has been devoted to working for social justice issues. I grew up in a rural farm community in northern Wisconsin and was somewhat sheltered from social justice issues; therefore I was naive and somewhat conservative when I left that community to attend the University of Wisconsin-Madison in 1967. Early in my first college semester of, I was inadvertently embroiled in the midst of a campus anti-war demonstration that erupted into police aggression, tear gas, and much chaos. I was immediately politicized. This launched me on to the path of learning about social justice issues and prioritizing my time and energy to work for social change. Read more>>

Dan Denton

I recently left the best job I ever had, as a union autoworker, where I served as an elected chief union steward. When the company offered a small buy out package as an early retirement, I thought “no way,” it’s not enough money to give up this job and the benefits. I’m in my early 40’s. I”m too young. But the more I thought about it, the more I remembered that when I was 7 years old I didn’t dream of growing up to be a labor leader, or an autoworker. I dreamt of being a writer. I’d already been widely published, including a novel and a novella, and I’d started to earn a little money as an artist the last few years,, but less than 10% of what I made as an autoworker, I decided to buy and remodel a 20 year old travel trailer to live in, and travel, and live a less expensive lifestyle, and I created a Patreon account that I’m still not good at using, but I’m up to 17 subscribers and nearly half a month’s worth of groceries coming in from supporters, just in my first couple of months. Read more>>

Cazarán

For me, the biggest risk I take every day is to have chosen to make a living from art, totally distancing myself from the idea of a monotonous and traditional life, as well as believing in myself, no matter what happens against all odds. Read more>>

Noah Kwon

I am currently embarking on the launch of a brand named NOAH, a health and wellness-focused tea brand set to debut in just a few months. This endeavor is not just a business but a personal journey rooted in a deep-seated passion for holistic well-being. Read more>>