Tony Robbins says the #1 human need is certainty, but do you know what the second need is? It’s uncertainty. This tug of war between the competing needs of safety and risk are at the heart of so many dilemmas we face in life and for most folks the goal isn’t to eliminate risk – rather it’s to understand this core human need. In our view, the best way to understand or learn is through stories and so we’ve asked some very talented entrepreneurs and creatives to tell us the stories behind some of the risks they’ve taken.

Jorge V. Gonzalez

The biggest risk I’ve ever taken wasn’t something I planned—it was something life forced me into. For over 20 years, my identity was tied to my work. I knew who I was, what I did, and where I was going. Then, in an instant, everything changed. I became disabled and could no longer do the career I had spent decades building. Read More>>

Kiki Alvarado

One of the biggest risks I’ve ever taken was stepping away from a 22-plus-year career during the uncertainty of the COVID-19 pandemic to become a full-time entrepreneur. At the time, my husband and I were operating our distribution company, and like many businesses, we were navigating the chaos and instability caused by widespread shutdowns. Read More>>

Teresa Sawatsky

As a young woman, I had many dreams and goals I was chasing, then motherhood shifted my gears to raise these cuties the best way I could! Watching our children grow and chase their own dreams is so inspiring that it brought back to life some of my own dreams that had been laid aside. Read More>>

Rob Malloy

After serving in the United States Air Force and spending over 15 years in corporate America, I reached a point where success no longer felt like fulfillment. On paper, I had done what many would consider enough—I served my country, built a career, and checked the boxes. Read More>>

Rachel DesRochers

I remember so clearly when someone came up to me after I gave a talk and told me they couldn’t believe how risky I was. And I think it was the first time I ever thought of me and my work or me being an entrepreneur as risky because I felt so slow and low and practical. Read More>>

Alice Yang

It won’t surprise anyone to hear that doing art full time is not the stable choice. But I think what gets lost in that framing is that the risk isn’t just practical — it reshapes how you see the world. To give some context: I started my professional life squarely in the corporate track. Read More>>

Joe Brandmeier

Ok, here’s the thing about “risk”. I’ve never really liked that word. It feels like everything’s a risk in some way or another. I like the words – chance, or possibility or exposure! These feel more alive, more exciting – more positive facing! I took a chance when I spent several days in the Alaskan wilderness photographing grizzly bears. Read More>>

Izabela Bos

One of the most meaningful risks I’ve taken was stepping into entrepreneurship and launching my brand, ThatDigitalBelle. At the time, I was already deeply involved in strategy, content, and organizational initiatives. On paper, it didn’t necessarily make sense to take on more. Read More>>

Kodazia Wilson

One of the biggest risks I’ve taken was stepping away from driving semi trucks to start my own cleaning business. Trucking was steady, and I knew what to expect every day. I was used to long hours, being on the road, and just handling my responsibilities. It wasn’t easy, but it was predictable and it paid the bills. Read More>>

Robyn M Mussler

When COVID hit, everything around us came to a halt. Schools shut down, events were canceled, and programs everywhere pressed pause, many indefinitely. At that moment, I was faced with a decision: do we shut down alongside everyone else, or do I find a way forward in the face of uncertainty? It would have been easy to cancel, it would have been expected. Read More>>

Kayla Fearing

Leaving Traditional Healthcare- To Advocate for Plant Medicine: How Healing Fear Consulting, came from Cannabis. I grew up as a little girl wanting to be a doctor.” By middle school, in 2004, I was considering being an addiction specialist, and then in high school, I wanted to be a Pulmonologist. Read More>>

Alyssa Walke

Six years ago, I took the biggest risk of my life—I opened my own beauty studio. It happened in what I can only describe as the perfect storm. In the middle of the pandemic, I had just been laid off. Businesses everywhere were shutting their doors, and I kept thinking… who is going to hire an esthetician when the world is in quarantine? Read More>>

Chaise Cortes De Vargas

I took a risk that most people probably would’ve waited on—but I didn’t. I created a film called Ordinary Heroes: The Crosses We Bear. It’s about the aftermath of 9/11—the loss, the grief, and what happens to people after the world moves on. At its core, it’s really about broken people who bury wounds so deep they don’t even recognize who they’ve become. Read More>>

Ja’ness Tate

Taking a risk for me was really choosing myself, even when I wasn’t 100% sure how everything was gonna work out. I recently decided to move into my own place and fully bet on myself as an artist. At the time, I had momentum, I was performing, building my audience, dropping music, but it still didn’t feel “secure” yet. Read More>>

Markus Olind

I graduated college and worked in Corporate Finance for 2 years. I started comedy as a senior in college, but once I started working professionally after graduation, I realized how much I hated corporate finance and how much I’d rather be doing comedy. I spent the next 18 months coming up with a plan to quit my job and go full-time comedy. Read More>>

Anne Gillaspie

When Anne Took a RiskAnne Gillaspie always believed that the deepest fears often reside in silence, echoing through generations. Her journey began as she confronted her own inherited patterns—those silent scripts that dictated her actions, emotions, and relationships. The Turning Point: Speaking Her Truth During a particularly challenging moment, Anne decided to embrace vulnerability. Read More>> 

Jonathan Haywood

Ive always felt that the way would reveal itself. Always. My wife of 17 years doesn’t understand how I can go on a trip or set about to do something without having every detail planned out, because she’s a planner. As I see it, there are a couple problems with planning everything: 1.Read More>>

Aldo Casabona

I used to believe I took no risks at all, but that soon changed when I moved to the US to study acting. The uncertainty of the career plus the short time I had to prove my worth certainly meant I made a huge and risky decision. This year, I moved back to my home country, Chile. ‘Was it all worth it? Read More>>

Michele Wilson

One of the biggest risks I’ve taken didn’t look like a bold leap from the outside. It looked like stepping away from something that was already working… which, in most people’s opinion, is not the move. 😄 At the time, I had built real momentum in the construction industry through Coffee with Contractors®. Read More>>

Vasilios Malkotsis

While growing up in New York, my dream was to be a pro BMX rider. In high school, I used academics as a means of escaping the harsh winters — I did well enough as a student to get accepted to University of California, San Diego for engineering physics. Read More>> 

Philip Cardella

In 2004 I took a big leap and opened my own brick & mortar location in my twenties. ! The ambitions step forward was a 3000 sq. ft. facility, 5 minutes South of Downtown Austin. It was a fun time in life to take a risk and an exciting process. Going all in successfully was the only choice! Read More>>

Nicole Aliseda

I think the biggest risk I’ve taken was coming to Los Angeles and not giving up. I was 18 and had a dream. I came here alone, with no family or friends, so it was definitely a little scary. Read More>>

Kaitlyn Brophy

I started my business completely on a whim! I have enjoyed painting and drawing as a hobby throughout my entire life and have always made handpainted cards for friends and family. Read More>>

Quania Jones

There was a moment in my life where everything felt like it was shifting at once, personally, emotionally, and professionally. On the outside, I had the foundation of something strong, but internally I knew I was being called to evolve into a completely different level of myself. Read More>>

Madelin Santana

There was a season in my life when everything on the outside looked strong… but everything on the inside was quietly breaking. I am someone who paid the price for the insight I will share: I was leading, delivering, showing up for everyone. From the outside, it looked like momentum. Read More>>

Mētztli Wolf

One of the biggest risks I’ve ever taken wasn’t a single leap—it was a series of decisions that asked me to trust myself indefinitely when there was no external proof that anything would work out. I walked away from stability—suburban housing in my home state, six-figure financial security, and any clear, conventional path—to build something that didn’t fully exist yet. Read More>>

Madeleine Doré

I was doing a degree in English Literature at the University of Birmingham in England. I loved writing so much, but I just was not happy in that place. I needed to change something. And truth be told I didn’t think a degree in English Literature was what I was supposed to be doing. I loved acting ever since I was tiny. Read More>>

Vickie Harris

In 2011, I was the co-owner, graphic designer, and office manager of a very busy audio/video duplication company. I was also the mom of 2 human boys as well as 2 furry babies. One of the fur-babies became very ill and passed away. It was unexpected and I wanted to know why. Read More>>

Cat Boyko

Honestly? I’ve never been someone who was afraid of risk. Terrified sometimes, yes – but the fear that’s always driven me more is this one: what if I stayed? What if I stayed somewhere I’d outgrown, in a life that no longer fit, just because it was familiar? I’ve switched careers multiple times. Read More>>

Dr. Maggie Hogan

I find the idea of “taking a risk” so fascinating. I often look at much of what we do as humans as “taking a risk”. For many of us, it is a risk to share something vulnerable for the first time in a relationship, to move to a new place, to learn a new skill, or even to walk out our front door. Read More>>

Susan Semmelmann

One of the greatest risks I’ve ever taken didn’t begin as a bold business move, it began quietly, being called in obedience in the middle of a full life. Read More>>

Maricruz Carrillo

I quit my safe 6-figure job to dedicate my entire energy to my unprofitable business. I had been in my product development engineering job for over 2 and half years, making good money, receiving a paycheck every two weeks but SUNMUD started asking for more of my attention. Read More>>

Chef Ashley Dominique

Becoming an entrepreneur is all about taking risks. In January of 2019 I realized that if I quit my job that I would bring in more revenue working for myself than working a part time job and working for myself. Now mind you I’m a single mother with 3 daughters. I just knew it could work long as I didn’t give up! Read More>>

Devon Mabry

One of the biggest risks I’ve taken was leaving everything familiar behind and moving to North Carolina to start over. Before that, my life was surrounded by a lot of negativity violence, legal trouble, toxic relationships, and people I thought I could trust turning on me. I had been in situations that could’ve easily kept me stuck in that cycle. Read More>>

Nadine Maldonado

One of the biggest risks I’ve ever taken was choosing to rebuild my life from the ground up after everything I had worked for fell apart at the same time. A few years ago, I found myself navigating divorce, closing a business I had poured my heart into, and moving back in with my parents with my children. Read More>>

Daisa Smith

As of 7 months ago I left my full time job of 5 years and my relationship to be a travel nurse. As someone who does not do anything without thorough planning and fail safes in place this was a complete shock to anyone who knows me. Read More>>

Madeline Rose

Choosing to leave the safety and security of a job to create my own. For years, I tried to balance having a ‘day job’ and pursuing wedding photography, but I was never able to give it my all.  Read More>>

Amber Vargas

Taking a risk at trying my hand at entrepreneurship hasn’t been an easy feat. From creating an apparel brand that was rooted in Embracing the Fire Inside Every Girl inspired by my daughter, to pivoting the business because I was told by a corporation to close up shop. I didn’t allow them to defeat me. Read More>>

Megan Johnston

I was working in the Orlando Florida area for 8 years. When my daughter was going to start school we decided being closer to the midwest was best option for our family. I left a great business that I had built, and a non profit to move to a non metropolitan area and start an academy at big cedar lodge. Read More>>

Melissa Padilla

I took a significant risk when I decided to leave my life and career in Tijuana, Mexico to pursue a dance program in New York City. At that point, I had built over a decade of professional experience. I had worked with one of the leading dance companies in Mexico, was teaching and choreographing across multiple studios, and co-directing my own projects and community initiatives. Read More>>

Jasmine Mejia

Taking a risk for me looked like stepping into rooms where I didn’t know a single person but still choosing to build something bigger than myself anyway. When I decided to create a community for small business owners, leaders, and creators, I had no guarantees. I didn’t have a built-in network, a huge following, or even certainty that people would show up. Read More>>

JP Gendron

Stepping away from a predictable career path to build my own agency wasn’t a move made for the sake of being edgy, it was a calculated bet based on an assessment of today’s general workplace. There’s a persistent myth that a traditional career or steady job is the safe bet. In reality, that stability for my generation is often a borrowed illusion from the past. Read More>>

Tatianna W

I feel like life itself is always about taking risk. The biggest risk I’ve taken so far was me relocating to Georgia at the age of 18 to start my dream business. Growing up, I always knew I wanted more for myself. Different than what I’ve seen during my early childhood. Black entrepreneurship wasn’t something of the norm back in the 90s – early 2000s. Read More>>

Anabelle Lefevre

The biggest risk I’ve ever taken was choosing not to be afraid of change. I’ve always been willing to pivot, to move, to start over. The first time I left my “big girl job,” I was teaching 5th grade. My husband and I relocated to Texas, and I remember how scary that felt. I had so many questions, so many unknowns.  Read More>>

Sway Hunter

One of the biggest risks I ever took? Man… moving to Atlanta. No question. It really started with a conversation between me and my mom. Nothing dramatic, just one of those real moments where we both kinda knew… yeah, it’s time. Time for me to get out the nest and see what I’m really made of. Read More>>

Ed Dixon

Starting a business is always a gamble, but launching a fine art gallery with no formal background in the industry is a specific kind of leap. When I opened the Edward A. Read More>>

Sarah Nidek-Eberle

A lesson I learned in 2025 was to separate work from my personal life. As a Neurospicy, intuitive empath I often see the best in people. Working out of my basement allowed people access to my sacred safe place. Not everyone is deserving of that privilege so I was desperate for a solution. 2025 was a low sales year for most small businesses. Read More>>

Joi Miner

The biggest risk I’ve taken is betting on myself. Being an artist, most of us do it as a part-time thing, never fully diving into it. I always used writing and my words to generate income, but there’s this thing called Imposter Syndrome that kept me at bay. Read More>>

Mika McCalla

When I was 15, I wanted to be a music manager. At the time, I dreamed of a life filled with black leather jackets and staying off-stage. That dream led me to USC—the place where everything changed. I took a risk and bet on myself: to grow, to build, and most importantly, to believe in myself. Read More>>

Carly Curry

Honestly, it was a risk starting my officiating business. I really had no qualifications to be a business owner… or an officiant, but like a lot of stories these days, my best friend asked me to officiate her wedding and I said yes. From there, I thought: Maybe this could be a career path for me. Read More>>

Nicole Utama

Moving halfway across the world is one of the biggest risks I have ever taken. I was born and raised in Indonesia, and I made the decision to move to the United States to pursue my Bachelor’s degree in interior design. Growing up, I had always dreamed of studying abroad. Read More>>

Chelsie Nunn

I held onto a four-wheeler while it spun donuts onto ice. We were all in a line, maybe four or five ATVs, spiraling on the snowiest East Tennessee night in a while. Two folks per four-wheeler in synchronized circles traveled down the icy city street like helicopters against a pavement sky. Read More>>

Leah Weinberg

Oh, that has to be when I closed down my successful New York City wedding planning business to start a new business in a field I swore I would never go back to…law. I started my adult life with a career in law, as a commercial real estate attorney, but the work bored me to tears. Read More>>

Mitchell Schaps

In the winter of 2022, COVID had dragged into its second year, and I had been working remotely that entire time. For the first time in years, my wife and I were living alone—no roommates, no built-in social circle—just the two of us in a new house in Burnsville. Read More>>

Narae Kim

I’ve never been someone who takes risks for the thrill of it. I just fall in love with things deeply, and then I figure out how to build a life around them. And I’ve never lost. Not because everything went perfectly, but because when you’re driven by your passion, every outcome teaches you something, and every chapter helps open the next one. Read More>>

Hortencia (Tenci) Campbell

At the time, I had what most people would call a stable life. I had a solid remote accounting job, predictable income, and I had just had my baby. But every time I pictured going back to work—long hours, repetitive tasks, and constant bureaucracy—I felt it in my body. Read More>> 

Olivia Schmitt

Starting Liv With Light LLC was an opportunity for a fresh wind in sharing love and light through the beauty of this world behind my lens. It was a blessing and dream in the making. God is my main motivation and had been planting seeds all along. Read More>>

Mercedes Nelson

One of the biggest risks I have taken up to this point in my life was deciding to embark on my entrepreneurial journey. It was the last quarter of 2018, and I was burnt out from work while also pursuing my Bachelor’s degree in Business at the time. I was also beginning my self-love journey. Read More>>

Mia Mauri

The biggest risk I have taken was starting my podcast and marketing agency. Which is ironic because that is what this interview is solely about. Read More>>