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.

Inês Merino

The biggest risks you can take in your life and business are the ones where you choose to put yourself first, above anyone (or anything) else. Read more>>

Lauren Engelkemeyer

A few years ago I decided to switch from making a handmade product that was my best-seller, to only offering it as a do it yourself sewing project. Read more>>

Jordan / Chris Bell / Limpert

When it comes to promoting underground electronic events, there is no shortage of risk. In 2002, congress signed The Reducing Americans’ Vulnerability to Ecstasy Act of 2002, commonly known as the RAVE Act. Read more>>

Samuel Kochman

Hollywood is a risky business– pun intended– so starting a production company amidst a great transitional period in our industry may have seemed crazy. Read more>>

Angela Stevens

Change makes most people uncomfortable, but most often I find it hopeful and energizing more so than unsettling. For me, the risk was in NOT changing to a new focus in my next chapter. Read more>>

Julie Cielo

After establishing a healthy private celebrity practice in Neuromuscular Therapy, Intuitive energy work, & Yoga, leading retreats in America, Peru, and Bali, I spoke consecutive years as a guest panelist for hundreds at a Women’s Wellness event. Read more>>

Henry Kemp

I would say the biggest risk I have ever taken was moving to Los Angeles with no family or friends. I had some success back home in Utah with my clothing brand Hippie Culture and I was told it had potential to do better in LA by strangers considering how well known LA is for fashion. Read more>>

Austin & Shilo Kirkpatrick

Does anyone else feel like they made extreme life-changing decisions during COVID lockdown? For us, it was like, “Hey, if it happened during a world shutdown and doesn’t work out, there are far worse things happening, and it won’t be a big deal, right?!” Read more>>

Jesus Chavarria

Where do I even begin? Well, I’m a first generation college graduate and first time performer in my Mexican family. It is important to say that a life as a performer or anything having to do with the arts was never in the cards for me, that is until I decided to take a leap of faith and audition for a performing arts college. Read more>>

Diana Budko

Oh wow, that’s a fascinating topic for me to talk about! Honestly, it feels that I am taking risks more often than not. What makes me think that – a tingling sensation in my hands and feet that I get; Read more>> 

Chelsea Evans

I took the risk 4 years ago when we decided to create opportunity from defeat and dive into retail with next to no knowledge of what we were doing. I had lost my job due to the COVID pandemic, and there was a lot of uncertainty about what to do next. Read more>>

Mary Blank

Ah! Risks. A topic I could discuss for hours. Seven years ago I made one of the hardest, scariest decisions of my life, and that was to leave everything I had ever known. Read more>>

Hunter Wilson

A risk I’ve taken is essentially how I use my time. With YouTube, I’m consistently investing time and money into the channel, mostly in my trucks. Read more>>

Merri Darling

It’s coming to the end of another very long day; I’m at one of my three jobs, and my mind is in a million places at once, when I receive a text message from a friend, asking me to take in a sick kitten that was found in someone’s auto shop. Read more>>

Tim Chenault

There could be many risks you could face when you’re exploring new ideas… it’s just as simple as weighing your pros and cons for every decision you make. Here are some examples: Read more>>

Melissa Locke

A friend of mine owns Le Petit Cirque which is a cirque company that performs all over the world. While my husband and I were attending one of her events at Pageant of the Masters in Laguna, she asked me to model at her next show on their red carpet. Read more>>

Deszerae Martinellé

I am at the point in my life where I’m taking risks and I’m super excited about it! I’m stepping away from being suite based and am focusing on traveling and doing pop ups with my business. Read more>>

Sady Sparks

A few years ago, I decided to take a trip to New Zealand to visit a good friend of mine. I’d never been and didn’t know anything about the laws. Read more>>

Stephanie Gonzalez

The greatest risk I’ve taken in opening this business has been doing so in the midst of significant personal health challenges. Just three months before my lease began, I suffered a heart attack. Read more>>

Brielle Winslow-Majette

As a black masc presenting woman with facial hair, I take a risk Everyday! Who I am goes against all that European and white supremacist societal ideals for women that exist. Read more>>

Laura M. LaVoie

In 2009, my partner and I broke ground on the foundation for a 120-square-foot home in the mountains of Western North Carolina. We had always wanted to build something on our own, but it was never about the house. Read more>>

Brandy Trieu

TeaTown has always been more than just a fleeting idea; it’s been my parents’ lifelong dream, one that I am determined to help them fulfill. Read more>>

Ridhi Bhalla

A risk I took was choosing filmmaking as a professional career and as a degree in undergrad. I wanted to go into journalism and become a travel photographer which I still love dearly but film was never my first choice. Read more>>

Andy Morales

One risk, I took was when I began doing Unraveled Influence, originally in 2020, under the Jam Them Down platform banner, it was turning my podcast into a platform and building a team. Read more>>

Charnell Smith

I have been working since I was sixteen years old. So you can say, it’s all I’ve known. After starting a family, finances become the number one priority…roof, food, clothes. Read more>>

John Schmitz

I took a formal turn in my artistic practice somewhat recently. My studio moved outdoors, as it were, to the intertidal zone near our cabin. This zone—where sea meets land between low and high tide—is a dynamic space of life, death, reproduction, and feeding in negotiation with daily tidal cycles. Read more>>

Ali Parsons

When I graduated college with my BS in Business, I moved to the “big city” for a career opportunity that turned out not to be what I had hoped. Read more>>

JR Strickland

The interesting thing about taking a risk is that sometimes, it’s a bigger risk in not trying. When I decided to pack everything I own into my SUV and drive across country from Chicago to LA to pursue my dreams of working in the entertainment industry, I was constantly asked was I afraid. Read more>>

Jesze Pillay

Loaded question… taking a risk seems to be my preferred way of life.  No risk, no reward they say, this rings true when I look back a few years ago and how my work life has transformed due to the risks I decided to take along the way.  Read more>>

Halley Sutton

I’ve known I wanted to be a writer almost my whole entire life. But for a lot of my adult life, I wasn’t actively writing. I fell in love with reading books as a kid—my parents had a business that involved lots of traveling, and reading on the road was my favorite way to occupy myself. Read more>>

Erin Hadlow

I would say that personally, I would never consider myself risk averse. Professionally, that is a very different story. There is safety in working for an established organization. Read more>>

Veda Leclerc

One of the biggest risks I’ve taken was deciding to complete my undergraduate degree in just three years while simultaneously dealing with significant health challenges. Read more>>

Aja McClanahan

I think we can all agree that 2020 was the craziest year most of us have seen in a long time. The world as we knew it entered the Twilight Zone, and most of us were just trying to survive and make sense of things. Read more>>

Holly Meyers

Leaps of faith (taking a risk) require not just faith you’ll be ok … They require careful planning, educating yourself on what you want to do and the skills it requires for what it is you are pursuing. Read more>>

Cheryl Patella

This is a story about me taking a huge risk in my life. I left everything I knew to start a whole new life I was not familiar with. I was born and raised in Miami, had a successful business of 40 years, and lived in my more recent home of 14 years that I had remodeled to what I wanted. Read more>>

Lu Patino

Leaving a successful corporate career to follow my true purpose was the most significant risk I’ve ever taken. Despite the financial stability and professional success, I felt unfulfilled and was dealing with health issues and a toxic relationship.  Read more>>

Carolyn Kay

Stepping into writing professionally was a huge thing for me. It wasn’t a financial risk–I still have my government career, but it was an emotional one. Read more>>

Sydney Scott

Growing your own business comes with a lot of risks in itself. However, the most significant for myself so far has been making the leap from “whenever I have time to do it,” to full time and making it my priority. Read more>>

Pilar Ortiz

I have been a Director of People and Culture for more than 10 years, working with luxury hotel brands. I have enjoyed a wonderful career, working in various countries such as Venezuela, Mexico, Costa Rica, and the United States. Read more>>

Dree

Man I gotta say, throwing these listening parties have been the riskiest but most rewarding part of my journey so far. Any of the events could’ve gone left at any moment but luckily I got a great team around me. Read more>>

Lawrence Iriarte

Leaving a stable traditional office job to pursue the arts and invest in myself and my passions. – All my life I’ve loved the art of storytelling and creating in comic books.  Read more>>

Adriana Sabrina Koc Spadaro

In the Summer of 2022, I got the dream job I always wanted. One year later, I quit to pursue a deeper calling. My career in corporate marketing was not shy of meaningful opportunities. Read more>>

Greg Nardi

I began teaching yoga in 1996 at 22 years old. As both a career and a vocation I’ve taken numerous physical and emotional risks in my pursuit of physical, emotional, and spiritual growth including annual trips to India over a decade to pursue deeper learning from masters in the country of yoga’s origins, Read more>>

Lindsay Bowie

In 2017, I deployed to Kuwait for 3 months as a contractor in support of the military. I volunteered for this deployment, having started working on my assigned portfolio only 7 months prior. Read more>>

Amy Crosby

Taking risks has been an integral part of my career, and my story with Profferfish exemplifies this. During a successful career in Silicon Valley, I always felt a tug to give back to my community, but never had the time. Read more>>

Banah Winn

I think every step of the journey has been taking a risk, from putting myself out there, to creating something new and authentic that I haven’t seen anyone else do. Read more>>

Marilyn Hunt

I was living in LA, Redondo Beach a beautiful place I knew so well. I saw the ocean every morning and heard the waves every night but the life I knew was turned upside down. Read more>>

Air Kraehmer

Air Kraehmer is an award-winning author, entrepreneur and philanthropist known for her exceptional creativity and magnetic acumen. With a passion for storytelling and a keen eye for opportunities, Read more>>

Sean Russel Herman

I was working as head narrative for a production company, making great projects with great people, but something was missing. It was always my dream to make films I was proud of, but the more success I found, the more time I spent in the office, on calls.  Read more>>

Sage Gallon

Taking Risks seems like all I’ve done. I did a Painting for a good friend of mine who was pregnant with her second child. That was, as hard as it is to believe, over 23 years ago. Read more>>

Luca Seretti

One of the most significant risks Luca Seretti has taken was his decision to move from Rome, Italy to Los Angeles, USA, to pursue his dream of becoming a cinematographer and later, a luxury clothing brand founder. Read more>>

Shannon Berg

I started this business just a little over a year ago with no clue what I was doing. A wife, mom of 2, and a lot of energy. When I first heard about a hat bar, I was immediately intrigued and started doing my research. Read more>>

Doug Hanson

In 2017, I took a pretty significant risk by leaving my secure full time job performing at Disney World in Florida to pursue my passion for film and television in California. Read more>>

Kathy Croman

I was a stay at home mom for years and when the pandemic hit, I needed an outlet and started jewelry making for fun. I’ve always loved jewelry and jewelry making, but hadn’t done it so long. Read more>>