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.

Robert Uncles

One of the biggest risks I’ve ever taken was starting my own company, Weimar Pictures, with my brother Thomas. It was definitely a leap of faith, but it came at a pivotal moment in my life and career. Let me set the stage for you: I’d just wrapped a one-year contract with Netflix’s creative studio, where I got to work on some amazing projects. Before that, I’d spent years freelancing at different agencies and shops across town, soaking up all kinds of experiences and insights. But during my time at Netflix and other places, I started noticing some cracks in the system. Budgets in unscripted TV, for example, were razor-thin, and every dollar had to stretch. Yet, in the broader industry, so much of the money was going to management layers instead of ending up on screen where it could really shine. At the same time, I saw the same handful of artists getting hired over and over again, while a lot of fresh, hungry talent struggled to break through. Read more>>

Madeline Quint

In 2020, I took a risk that would change my life and the life of a dog named Boots. I first saw his picture posted on the animal shelter website—alone and terrified in his kennel. There was something about his eyes that drew me in, and I couldn’t stop thinking about him. Later, an animal control officer shared that Boots had been abandoned in a dangerous neighborhood on the 4th of July, trapped in sharp wires and terrified by the fireworks. The shelter labeled him as “aggressive” and unadoptable, and they were ready to put him down. But I couldn’t accept that. I called the shelter every single day for three weeks, pushing to meet him, despite their warnings. Read more>>

Alberta “abby” Keen

Making the decision to quit my 9-5 to open a brick and mortar with no experience in owning a business. Doing it scared with no regrets! I didn’t want to be in my old age, thinking what could have been if I had just opened a bakery when I was younger. At 55 I felt like baking full time was calling out to me. I thought about it all the time. My husband did not see a bakery in his future but he has been my biggest supporter. My friends and family have all been very encouraging, helpful and supportive. That is what makes this work for me. For a year I have been working at the bakery early in the morning and late at night, with my husband selling it during my 9-5. We recently participated in a cupcake festival and it was a family affair, my kids, parents, sister, cousin and husband all played an important part, with lots of love and technical support from around the country. Read more>>

Drew Lundberg

Prior to starting 12|21, I always wanted to own and operate my own studio. It felt like something that was always out of reach, not attainable, etc. When I started 12|21, I had a steady income, and our second child was just born. It was a very stressful time, but with my wife’s support, I knew it was the right decision to ultimately be happy. I think risk is necessary in life. I think you have to be uncomfortable to be more comfortable with yourself and your goals. I think the correlation between passion and risk-taking can be integrated in a really positive and motivating way. Read more>>

Lee Deas

The pandemic threw everyone for a loop. Businesses were scrambling, and we knew we couldn’t just sit back and wait for the storm to pass. We needed to evolve. That’s when we spotted an opportunity – a chance to shake things up and take a leap of faith. There was this outdoor and active lifestyle company, one we’d always admired, with a strong brand, amazing products, and a ton of untapped potential. So, we took the plunge and acquired them. It was a bold move, but we saw it as a chance to: Branch out: Adding a new sector to our portfolio meant we weren’t putting all our eggs in one basket. Read more>>

Brigid Turner

I took a risk in 2020 (during the height of thevpandemic) to produce, direct, and star in my first feature film. “I made a movie during the pandemic, not about the pandemic “. I took a chance on myself and everyone who came onboard to help make this film took a chance on me too. I taught my friends and running peers how to be crew. 80% of the actors were first timers working with a handful of professional working actors. Our film is currently on Amazon Prime. I am proud of the film we made with the little bit of resources. Read more>>

Stephen Ray Thomas

The truth is, I’ve always been a risk taker. It’s just who I am. I’ve always found myself happiest when I’m creating, even if it means struggling along the way. I’ve never worked a regular job, and I’ve never followed the typical path. Instead, I’ve always leaned into the unknown, trusting that if I keep doing the work, the rest will follow. One of the biggest risks I took was deciding to go all-in on my acting career when there wasn’t a clear path ahead. I didn’t have a big network, and success wasn’t guaranteed, but I knew this was the path I had to follow. There were times when I didn’t know if it would pay off, but I stayed focused. It wasn’t about giving up something safe—it was about betting on myself, trusting that the effort I put in would eventually lead somewhere. Read more>>

Adaria Crutcher

My whole life I was always told that as a young, Black girl mental health was not real: nobody goes through mental health problems. When I started high school, I started to see how bad people’s mental health could get. I saw students lose parts of themselves throughout high school. They lost their smiles, their joy, their motivation to continue. My school is known for being one of the best in our city; it is known for creating bright students. However, behind the A’s and perfect ACT scores lie students with declining mental health. After my junior year started, I realized that something needed to be done. In a school where most put aside their mental health in order to boost their class rank, mental health is seen as the forbidden fruit: nobody will talk about it. In February 2024, I and two other individuals -Aisha Ceesay and Satvika Kodali- took a risk and made an Instagram account tailored to mental health. We interviewed over 80 students, showing our school’s population how bad the great majority of their mental health was. We took a risk by mentioning how there were many suicidal students at our school, yet our risk allowed students to finally feel seen. For the first time, students at our school had a safe place where they could learn about mental health. For the first time, students at our school saw that they were not the only ones struggling to wake up and push through life. Read more>>

Denise Huynh

In 2010, amidst the challenges of an economic downturn, I took a significant leap of faith by accepting my aunt’s offer to run a restaurant. Leaving my stable corporate job felt risky, but the opportunity to create a space serving authentic Vietnamese cuisine—dishes I cherished from my childhood—was irresistible. I made the best decision I ever made with my mother, placing her as the head chef, ensuring our menu reflected the flavors and traditions that were hard to find elsewhere. Together, we crafted a mom-and-daughter venture, blending our passion for food with the warmth of family, all while navigating the uncertainties of the market. This bold decision not only fulfilled a personal dream but also allowed us to share the rich culinary heritage that shaped my upbringing. Read more>>

Mary Nguyen

It all began in 2022 when I was working as a social media intern for Eclipse Group, a Dallas-based entertainment company, when I noticed a lack of events catering to the K-pop community in the area. Due to the genre’s relative unfamiliarity and its status as an emerging demographic, most venues and clubs were hesitant to take the risk. Encouraged by my mentor, Peter Bui, I organized my first K-pop event in less than 24 hours—from planning to promotion. This event became an after-party for the Enhypen: Manifesto Tour at Ampersand in Fort Worth, marking my first significant risk. Determined to bridge the gap between nightlife and K-pop, the event gained significant traction, drawing over 120 attendees within a very short promotional period. However, despite the positive turnout, the venue and company incurred a financial loss. While most would avoid discussing the downsides of their ventures, I believe this risk was pivotal in shaping the person I am today. With encouragement from my mentors and positive feedback from the community, I became even more determined to create better experiences for K-pop fans. This experience marked a turning point in my journey, transitioning from being an intern to gaining valuable insight into the backend of the business and what it takes to create successful events. Read more>>

Jaime Coffino

My academic and professional journey has been shaped by a series of pivotal risks that brought me to where I am today. One of the most defining moments came when I graduated with my PhD in clinical psychology during the height of the COVID-19 pandemic. At the time, I was working under the supervision of a highly respected OCD and anxiety specialist in New York City. Her group practice was thriving, and she was able to offer me stellar supervision and a steady stream of patients. It was a comfortable and secure role and many people in my life were encouraging me to stay in this role. Read more>>

Vanessa Gelacio

I went to this Audition in Santa Monica for a Project that required the Principal actors to completely shave their head, very rarely I get auditions that are very close to where I live so I thought, piece of cake! I’ll just go right after work. As soon as I get there, all I see is teenage girls! around 13 and 16 years old, I thought to myself, what am I doing here!? theres no chance I’ll ever get this, they must have made a mistake calling me in for an in person audition… I went to the restroom and I was seriously contemplating just leaving, but then I convinced myself to stay and just go in the room, take the opportunity I have to act and Just start building a relationship with the Casting director and Director… (A lot of things happened but…) Fast forward to I ended up booking the job! and I was just in shock.. I was also going through a period in my life of a lot of Shadow work and self deconstruction so I was facing a lot of pain, and knowing I had to shave my head, my therapist warned me I might go through a period of grief because hair for women is such a big piece of Identity; but I did it! I took the risk… Fast forward to: I don’t know if you believe in the butterfly effect but, having shaved my head was one of the biggest risks and also most freeing feelings in my life!… When My hair started growing back, It looked so unique that it led me to book other bigger projects! like this new horror movie acting Opposite to Danny Trejo Read more>>

Kyla Williamson

In 2014 I was at one of the lowest points in my life. We were losing our home in foreclosure we were drowning in debt. We could not even see a way out of our situation. But we had faith and we knew that God had a plan for us and we knew we needed to change something. I had a very successful business being a hairstylist and my husband worked at FedEx as a driver. We had great jobs, but we felt like there was so much more that we were supposed to be doing. We were broke and spinning our wheels and going deeper in debt. I was involved in direct sales on top of my salon business. But I felt this urge that God had something more for me. Read more>>

Naseim Jabr

Securing our first office space was a monumental risk for Project Marque. At the time, we were progressing, but I needed to determine if it was the right kind of growth to build a great company. Were the clients we were working with daily the ones who could elevate Project Marque to the next level? Initially, we had to accept clients that weren’t the perfect fit due to our need for cash flow and capital growth. It was a difficult time emotionally and a significant financial risk, especially having to personally guarantee the lease as a relatively unestablished company, which added considerable pressure. Read more>>

Elizabeth “dr. Liz” Glover

I’ve never been afraid to take risks. As a child, many tried convincing me that was a problem; that my difference was rooted in directionless defiance. It is but by my own tenacity that I toughed through the critics that tried silencing my roar. I was made to be fierce, to lead, and to create impactful change. The more seasoned I got over the years, the more I learned to use the gift I was given–the gift mistaken for a curse. You see, I’ve always been of the belief that you’re either a part of the problem or a part of the solution–there’s no marinating medium. So, I chose to create solutions. Fueled and driven by the social adversities I both witnessed and experienced, especially in schools across America, I decided to serve sociological solutions. The risk: agitating a system submerged in the cycles of racism, sexism, and ableism–especially amongst those unwilling to admit this truth. As a former K-12 educator, this meant going against the grain of what was popular to instead do what I knew was within my power and my position. Read more>>

Kim Carey

I spent 25 years as a proffessional singer and then became a preschool teacher for 16 years. During the last several years of my teaching career I had a growing interest in spirituality. I had many spiritual experiences involving my intuition and grew very curious. I began a very dedicated practice of mediatiion and prayer. In 2016 after a long back and forth in my mind I ended my preschool teaching career and decided to dedicate myself fully to my spiritual practices. i began by getting certified as a mediataition and mindfulness teacher. After a breakthrough experience at a silent retreat I began to get the message from those I would call Spirit Guides to start a YouTube channel to ease people’s fears about the political changes that were happening in the country. It was a huge risk. Not only would it be putting myself “out there” like never before to be ridiculed or rejected but I might also disappoint myself in my own spiritual connection. Read more>>

Ana Hess

Taking a risk to launch Awakening Truth was the best decision I have ever made. Having your own smoke shop can be a transformative and rewarding experience, both personally and professionally. While risks always come with uncertainties, the potential rewards for those who take calculated steps are immense. Here’s why it’s important to embrace that risk, and why being grateful for it can amplify success: 1. Innovation and Uniqueness in a Growing Market- Breaking into a Niche Market: The cannabis and smoking accessory industry is growing rapidly, but it’s also competitive. A mobile smoke shop offers a unique solution for customers who may not have easy access to a traditional brick-and-mortar store. By taking the risk, you’re not only introducing a fresh idea but also positioning yourself as an innovator in the market. Read more>>

Keni Thomas

My name is Keni Thomas (Thomcat23) and I’m always overly cautious. This fear of failure alway kept the creative success I wanted just out of reach. Hard situations and circumstance changed that. With a career in the design industry I found myself often taken advantage of, then I was blessed with being fired. Yes, blessed. The skill set that I’d built over years in the industry was finally going to be tested as. the decision was made to make my own studio. I wasn’t going to plug myself back into that Matrix. At first the sheer dread and uncertainty paralyzed me, until I realized all the connections and good will I’d built over the years. My freelance list became a client list and the personal art gave me a product to sell. Aslo, securing licensing deals gave me the slight foundation to build on. I can’t say that working for myself is perfect, but it’s mine. My ideas, my concepts, my mistakes, my faults and I’m proud to own them all. I encourage ALL artist to create and sell their work, work independent of a client and use every bit of voice you have. Be bold, overly cautious kept me aggravated and unfulfilled. Read more>>

Lena Franklin

The most transformational risk I’ve taken what it comes to my life’s work was to create a healing organization that had never been created before. After working with thousands of clients and students over the course my career thus far, I saw firsthand (and within my own journey of liberation) that merging psychedelic plant medicine work, psychology and modern neuroscience was a complete game changer in healing (and, many times, even completely curing) mental health imbalances. And after those imbalances were healed, I began to witness the essence of my clients’ power emerge to the forefront. Overtime, a very specific multi-disciplinary methodology came together, and it was time to share it with the world. Here’s the origin moment….one night, my husband and I were sitting on the back porch of our home, listening to the wind rustling through the bamboo, after facilitating a ceremony, and we turned to each other with a spark in our eyes ~ “should we do this?” ~ was the telepathic question we were asking one another. We both had received this strong message to create an organization that utilizes plant medicine and other modalities to create healing and transformation in the world. It was a resonant YES….we’re doing this! Read more>>

Alvin Lin

One of the most significant risks I’ve taken was deciding to pursue a career in graphic design. Growing up, I always had a passion for art and storytelling, but the idea of pursuing a creative field felt uncertain and unconventional, especially coming from a family that valued stability and practicality. Choosing to study design at ArtCenter College of Design was a leap into the unknown—I was committing to a field that required not only artistic talent but also resilience, problem-solving, and a deep understanding of human connection. The backstory is rooted in my childhood. I always found joy in creating things—whether it was drawing, experimenting with photography, or making collages—but I wasn’t sure how to channel that into a career. When I discovered graphic design, I realized it was the perfect bridge between creativity and functionality, allowing me to solve real-world problems while telling compelling stories. Read more>>

Jaris Tucker

Podcast Guest Introduction Summary I’m excited to share my journey from a production supervisor to a business owner, and now to a speaker and thought leader. My story begins in the workforce, where every job I held was temp-to-hire. Despite starting at the bottom, I consistently rose to leadership roles, eventually becoming the head supervisor of a plant. Along the way, I learned invaluable lessons about leadership, spirituality, wearing many hats, and treating people with respect. However, my success wasn’t always celebrated. I was treated poorly for outperforming others, which ultimately led me to quit and take a leap of faith into entrepreneurship. Starting my own company was far from easy—I spent an entire year before earning a dime. I am the founder of Real One On One Consulting LLC, a business/management, consulting company and the founder of the #ThinkersAtWork.  Read more>>

Carrin Fernandes

I have been a licensed massage therapist over 24 years. I have had my private practice since 2009 located in Westfield, New Jersey. I built my practice all on word of mouth. I never advertised. My average client has been seeing me for 13 years. My practice was sold and steady. In 2021, my father passed away. I was at a crossroads in my life personally and professionally. I was struggling personally with this huge loss. I dove deeper into my own healing journey and became a certified life, health & bereavement coach. I decided to move across the country back to Colorado, my favorite state. That’s where I attended massage school. I left a thriving business in New Jersey to start completely over in a new area, where I knew no one and had no clients, Read more>>

Fatimah Hanif

I left what I thought would be my career at the time in the food industry as a Chef & Dietary Manager, which was extremely stressful, no matter how much I thought I loved my career. My body didn’t like the stress. I gained so much weight which caused high blood pressure & myself being pre-diabetic. So I knew I had to make a life changing decision. I quit my job & became a Vibrational Wellness Specialist, helping myself & others, from all ages to find their peace and happiness while calming their nervous system. Read more>>

Timothy Hill

When I reflect on the risks I’ve taken, one defining moment stands out: the day I packed my life into suitcases and moved across the country from Fort Lauderdale, Florida, to Los Angeles. Leaving behind the familiarity of my government career, my community, and the comfort of a predictable life was not a decision I made lightly. But deep down, I knew there was more to my story. I yearned to experience life beyond the borders of my home state and pursue my long-held dreams in entertainment, storytelling, and creativity. Read more>>

Tatiana Easley – Batie

Starting a business is always a leap of faith, but imagine doing so at one of the most uncertain times in recent history. That’s exactly the risk I took when I launched a brand-new business with my son just one month after the world shut down during the pandemic. With no employees but us, I invested every dollar in my bank account, hoping it would be enough to cover our rent. I was nervous and unsure, but the determination to make it work fueled me. Little did I know, this risk would not only pay off but also redefine our lives. Read more>>

Laura Mcgrail

Here’s a revised version of your story with a more polished and engaging tone: The biggest risk I’ve ever taken? Starting this business—no surprise there! Back in 2017, I was traveling full-time, working as an English teacher in Thailand and later as a waitress in Australia. For an entire year, I carried nothing but some clothes, a camera, a drone, and a computer on my back as I explored new places. Along the way, I started creating and sharing short videos from each country I visited. During that year abroad, a few friends reached out and asked if I’d film their weddings. At that point, I’d only ever done one wedding for free and had no real idea what I was doing—but I said yes. After I returned from traveling, I took a leap of faith and filmed those weddings. Read more>>

Ivana Cotto

I’ve taken many risks throughout my life, both curated and non-curated, from experimenting with artistic choices on an artwork, to leaving jobs for creative opportunities. For me, risk-taking is about diving into the unknown and trusting that growth lies on the other side. One defining moment came during my fourth year as an art major in painting with a minor in art education. I was working as a barista and selling my artwork at pop-ups to fund my studies when a friend recommended me for an art teaching position at a school I went to. I was finishing my minor in art education so , I decided to embrace the challenge. Read more>>

Blake Miremont

In 2010, I found myself at a crossroads. I had been living in Long Beach, CA, for eight years. At 25 years old, I was single, renting a beautiful apartment on the beach, building a blossoming career in the financial sector, and pursuing my MBA at Long Beach State. On paper, everything seemed perfect—my life was on an upward trajectory. Yet, I had never been more miserable. Over time, I began to realize I was heading in the wrong direction. As I looked toward the future, I saw myself becoming increasingly unhappy and unfulfilled in my career. But what could I do? The pay was great, I had worked hard to move up quickly in the company, and opportunities to climb the corporate ladder kept presenting themselves. Starting over felt risky and uncertain. What guarantee did I have that my next career wouldn’t leave me feeling the same way? Read more>>

Marise Plummer

Growing up, I have always been more of a risk taker. Whether that be me forcing myself to do skateboard tricks that were way too advanced for my level, me wearing a brightly colored/unique outfit that I know will make me stand out in high school, or me taking on the challenge of sewing my own prom dress a month before prom despite not having any previous sewing experience. I would say that my first big jump that helped land me where I am right now was when I decided to move to Paris, France for fashion design in 2018 right after high school. My first reason was that I didn’t want to go into debt since I couldn’t afford to pay for the fashion design program at Savannah College of Art and Design (SCAD) out of pocket. My second reason was that I wanted to experience another culture and learn French while doing so. Part of me always knew that to really appreciate the beauty and uniqueness of growing up black in Atlanta I needed to leave for a little while. What I never knew was that “little while” would turn in to me still being here 6 years later! Read more>>

 Cat Car

I would say the main risk I have taken in my business is being 100% authentically myself. When I first started out, I tried to be the perfect version of what I thought a photographer should be. Polished, overly professional, and a toned down personality who would photograph anyone that inquired with me. As I gained more clients, I started to realize I wasn’t happy and I wasn’t clicking on a personal level with the people that hired me. I started to phase out family sessions, headshots, and other areas that didn’t stoke my creative fire and instead focus on weddings and couples. As I honed in on my passion, I realized I still wasn’t quite tapping into the ‘dream client’. I wanted people who were like me – maybe a little weird, a little awkward, rough around the edges, who fight for what they believe in. I started writing copy that would actually be something to come out of my own mouth, and editing photos the way I wanted to – not what I thought would get me featured or published. Read more>>