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.

Ariel

This is a personal story, but it resonated for me about how I take risks in general, and how I learned to take more. A few years ago I was at a beach with my family at the tip of the west coast of North America. It was a very nice resort. We were in a condo that was at the top of the building. I went back to the room to change clothing. I went out on the porch while my family was down playing at the pool, very far away. The condo had it built for security so that the doors locked if you go out on the portch, even that high up. I was locked out. It was a hot day and I didn’t have my phone, it was inside. I tried calling down for someone to hear me, but no one could. I thought about what to do. Read more>>

Lauren Maxwell

The risk? Starting The Suite Studio before I was “ready.”

I launched my custom wedding stationery business while working a full-time job in environmental consulting, with a newborn baby, in the middle of building a house. No investors. No safety net. No perfectly curated brand strategy. Just a gut feeling that if I didn’t do this now, I’d regret it. I’m also a very impulsive person, so, why not! Read more>>

Axel Reinemer

One of my biggest risks was leaving my full time job as an electrician and going full time as a musician. It’s not just a job but it’s walking away from stability and taking a chance on something uncertain. It’s also sacrificing weekends and time with friends, family and all the people that mean the most to you. There were moments of doubt and fear, but deep down, I knew music was what I was meant to do. Read more>>

Isaiah Gilchrist
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Before I became a tattoo artist, I was 20 years old working at a deli cutting meat and making sandwiches just to make ends meet. I was living with a few roommates when I found out I was probably going to be fired. That moment forced me to make a choice: wait it out or take a risk. I chose the risk. Read more>>

Eddie Palmer II

In 2013 I packed up my car with a few trash bags full of clothes and 2,000$ to my name drove to LA from Charlotte NC. I had no job, no place to stay just a dream I was determined to carry out. Upon arriving to Los Angeles, I lived in my car for 8 months. I had a client who was selected for sports Illustrated Swim Suit and another client who was a aspiring model started being booked for commercials seemly every other week things took off. I started working with pro athletes, business owners, along with music legends. Read more>>

Tammy Kushnir

Taking risks is part of life’s adventures. The time finally came to take my biggest risk in life when I decided to quit my full time job and create art full time. It was absolutely terrifying and exciting at the same time. When that feeling hit, I knew I had to do it. I had created art and worked with galleries and licensing agencies before but never as a full time commitment. Read more>>

Wendy Valentine

The biggest risk I ever took was finally deciding to stop living a life that wasn’t true to me.

At the age of 45, I found myself at one of the lowest points in my life. I was going through a divorce. I was unemployed, deep in debt, battling chronic illness, depression, and grieving the sudden loss of my brother. Everything felt like it was falling apart—and honestly, it was. On the outside, I kept up appearances. But on the inside, I was lost, overwhelmed, and uncertain of how to move forward. Read more>>

Harold Frazee

I’ve been a musician all my life. I can’t really remember a time when I wasn’t playing an instrument. The quick story is..after high school I went off to Berklee College of Music and while there was playing in several different local bands when I took the first of many big risks. Left Boston, sent my equipment and belongings across the country, dropped everything and joined a 13 pc traveling show band. After a while of touring it was time for another… quit that band and created an original rock band looking for the deal and yes..traveling. Read more>>

Jaclyn Roberts

The Risk of Beginning Again—Twice I took a huge risk when I left Durango. During my years there, I lost my mother, went through a heartbreaking divorce, and watched the wellness studio I built—Habit—close during the COVID shutdown. It felt like everything I’d worked for, everything I loved, was slipping through my fingers all at once. Read more>>

Victoria Cisneros

Prior to starting Savage Mana, I was working full time as the Quality Assurance Supervisor of the Customer Service department at a large online coffee manufacturer/distributor. As I started taking my craft more seriously, and attending more local pop up events and shows, I realized that opening a metaphysical store would not only serve my family but also my community. I took a risk and quit my 40+ hr per week job and jumped feet first into working for myself in a brick and mortar location. Read more>>

Emma Farris

I attended the nation’s #4 film school without a lick of filmmaking experience. Growing up in Fresno, California I was surrounded by farm land, construction sites, and big fancy offices. My entire family was involved in either agriculture investing or residential construction, neither of which ever felt like the place for me. I was an avid reader and writer my entire life, but also busied myself with student government, journalism, and sports- I desperately needed multiple outlets that were more creative than plugging numbers into a spreadsheet and printing blueprints. I also attended a private, Catholic college-prep high school where some of the teachers remembered having my grandfather in class- and the culture there was to go to university, come back, take over the family business, and send your own kids to the same schools. Read more>>

Karina

The risk that began my soul-aligned business, The Divine Transcendence, was traveling to Orange County, CA, to become Reiki certified. It was the first time in my adult life that I followed my intuition without knowing what would come next. There was no plan, no business model — just a deep inner knowing that I had to say yes. Read more>>

Stephen Candelmo

After nearly three decades as a corporate attorney, I thought I had seen it all. I’d helped countless startups navigate everything from their first incorporation to major acquisitions, working at both big firms and boutique practices. The work was rewarding, the pay was good, and I had a clear path forward. Read more>>

Veronica Clanton Higgins

Opening the Compton Wellness Center was one of the biggest risks I’ve ever taken financially, emotionally, and professionally. After years of doing mental health equity advocacy and healing work in the community through pop-ups, events, and collaborations, I knew our people needed a permanent space, a sanctuary that felt like us in every way. A space rooted in cultural identity, radical healing, and accessible wellness. But the path to opening those doors was filled with uncertainty and sacrifice. Read more>>

Molly Kyle

The biggest (and the best) risk I have ever taken was to have the faith to always follow my heart in my career path. It’s called a calling for a reason- your life purpose will keep calling to you, even if you try to shrink from being seen. I tried to keep myself in a seemingly safe box in order to avoid failure or being misunderstood, but when the pandemic hit, I realized that this was not serving me or anyone else. The most authentic way for me to serve my community is to unapologetically live the roles of both creator and healer, and really, those two roles are one and the same. Going on my own unique path and combining bodywork, the esoteric, and Jungian coaching into a business while also keeping my creative spark alive as an actress is not always easy. It was not created from five year plans or spreadsheets. It is a non-negotiable way of life, an extension on my life’s passion, and a risk well worth taking. Read more>>

Kelsea Frobes

Before becoming a student at the University of Nevada, Reno, I had hoped to get involved with our student-run newspaper “The Nevada Sagebrush,” but wasn’t exactly sure how to do so. My freshman year of college, I became busy with other jobs, school, and extracurriculars. Working for the Sagebrush was always in the back of my mind, but I never knew when my time to join would be. As my senior year crept closer, I slowly began to think that I had missed the opportunity to pursue this dream. Read more>>

Kornelia Kruczek

Taking risks is often romanticized in the world of entrepreneurship. But sometimes, risk isn’t just a leap—it’s a series of quiet, persistent steps into the unknown. For me, that moment came after three years of building a recognizable photography brand in Poland. I was beginning to receive truly fulfilling offers. Yet, I decided to relocate my family and business to Mallorca—a stunning place, but a surprisingly closed market, especially when it comes to building relationships. Read more>>

Amy Miranda

Risk taking isn’t something I’d have always said I enjoyed, but over time it’s shown to bring the highest rewards both in life and in business. As an executive producer part of my job is to manage risk. Being an executive producer is like being a general contractor. You need to be as sure of the people you’re investing in as the people who are investing in you. Determining who, how and when is all part of the requirement of doing that work. I won a lot of awards globally for being able to do it so well, for so long. Read more>>

Madelynn Mackey

I would say a risk I took was in December 2023 when I decided to dedicate myself to photography.

I had just moved from Oklahoma to Portland in early 2023. I had spent the majority of the year attempting to adjust to the city, not knowing exactly how to do so with a remote job. It was a year filled with lots of personal challenges, change, and accidentally going the wrong direction on a one way street. Read more>>

Marina Klimann

While I was studying in Madrid, where my family is from, I was pursuing a double major in Business Administration and International Relations. Even then, I had always been passionate about film and storytelling. As I progressed in my professional journey, I began to realize that simply being an avid consumer of movies and television was no longer enough for me. I wanted to be a part of the industry, to help bring stories to life. Read more>>

Justin Moore

I was working a corporate job behind a desk making decent money and comfortable . When all of a sudden something came over me as I looked in the mirror in the break room and I knew this was not where God wanted me in life. So the risk was giving it all up and starting to get back into basketball through giving. Read more>>

Dominic Kawaja

Taking a leap of faith, I left behind the comfort and predictability of editorial photography to build CURB360 from the ground up. It was a major risk-shifting industries, starting with no clients, and investing everything into a vision I believed in. But I saw an opportunity to raise the bar in real estate media, and I committed fully. That risk became the foundation for a company that’s now thriving and expanding nationally. Read more>>

Teko Lewis

Before I ever picked up a camera, I was a general manager at a fast-food restaurant. I was around 22 when I got an opportunity to model for a magazine shoot on one of my off days. Excited, I told the other manager what I would be doing, and then he changed the schedule the day before for me to work. It was the night shift, I was angry, I knew I would be tired, but I went for it, came to work that night, wasn’t even late, but shortly after, I was fired. Read more>>

Erin Michele Soto

Taking a risk on myself meant believing in me and having a dream in my darkest hours, using it as a guiding light. The spark inside me fired up.

After a concussion (the kind that really makes you rethink everything), I had to face the terrifying idea that the thing I loved most — acting — might be off the table. It asks for your whole self: focus, timing, presence, emotion. And for a while, I wasn’t sure if I’d be ready to come back online to the world. Read more>>

Juan C.

To me, risk doesn’t always look like a giant leap. Sometimes it looks like choosing to live a life that actually feels true to who you are. It means turning down the noise, making space to hear your own voice, and deciding to move in a direction that stays connected to your soul. That’s the kind of risk I continue to take every day. Read more>>

Rob Mendenhall

Originally my business partner and I were renting space from his uncle and it only cost us $900 a month. After covid his uncle was wanting his space back so we had to look for a new space. We found a larger space and in a great location but the cost was much higher. My partner decided he wanted to focus on the other businesses that he started and wanted out of this business. I was going to move into a new space that was going to cost over $3000 a month just for rent, with no partner, after covid when so many businesses failed, especially things like gyms. Read more>>

Briana

The first risk I took was going the unconventional route of getting my esthetic license. Taking a leap of faith & showing up every day even when It was hard and when I was going through a tough time in my personal life. The second risk I took was becoming a solo esthetician and working for myself. Trusting in myself & taking that Jump. It’s scary to take that risk, wondering if you’re going to fail or not be good enough, but once you do, there’s nothing left to do but keep going and pushing yourself. Read more>>

Cassidy Maestas

The biggest risk I have taken since becoming an industry professional was starting my own business. 10 years ago I started cosmetology school not sure what I was doing, except I knew I wanted to to have a positive impact on my community. After walking down a few avenues in the industry I ended up working at SportClips and found my absolute passion. Barbering. 5 years latter I was ready to open my own business in order to provide the greatest experience to my clients and build a business that the city could promote and support. Growing up on the Eastside of the track I never thought I would be able to become a dual licensed business owner. Read more>>