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.

Jonathan B. Williams

The biggest risk I ever took was betting on myself after losing everything I thought defined me. I began my college journey at Texas State University on a track and field scholarship, driven, confident, and certain that athletics was my purpose. But during my sophomore year, a major pectoral injury changed everything. Read More>>

Matteson Gregory

I was always the shy girl growing up. I never put myself out there or was the first to raise my hand in class. So the fact that I wanted to be a singer seemed impossible. But there I was dreaming of being a singer. Writing songs in my room after school. I knew that once I graduated high school I could start my dream. Read More>>

Casey Langley

I can say the biggest risk I ever took was investing into digital marketing training and courses . Since investing into digital marketing courses all the knowledge I’ve learned inside helped me to start my Ahmad’s Mission Merch clothing brand and my Trace and Cherish your memories Custom coloring pages. Read More>>

Jose Portillo

Making the career shift into full time fitness and wellness was a pretty big step for me. I had worked in luxury fashion retail for the majority of my adult life having worked as a stylist and shopper for Neiman Marcus and Saks 5th Avenue and for so long it had really treated me well and I had found much success and fulfillment there. Read More>>

Malas Sicarias

The biggest risk we’ve taken was betting on Malas Sicarias, not just with our money, but with our time, energy, and hearts. We believed so deeply in the story we wanted to tell, two best friends navigating chaos with loyalty, humor, and heart, that not creating it felt like the bigger risk. So, we went all in. Read More>>

Jazmine Lewis

I learned how much of an impact you have to be in this thing called life and it can be anything as long as you are proud of yourself. For me life is a risk whether you’re graduating from school, starting a job or career, becoming an entrepreneur, healing, etc. Read More>>

Jeanne Scott

I’ve taken many risks. Some life changing, some could have been life ending. My first big risk was to enlist in the US Army. I wanted to get away from my small home town right after highschool and so the military seemed to be the best avenue to do that. And for only 4 years-I was young. Read More>>

Kendra J.

Well, as we all know, it’s 2025. The economy is terrible, the job market isn’t much better, and everywhere you look, people are fear-mongering about holding on to your job. But I actually took the risk of resigning from mine (yes, in this economy) to focus on building my own business ventures. Read More>>

Marcia Reed

I think it’s brave and a risk just to be a creative person! O’keeffe said it best. “To create one’s own world in any of the arts takes courage.” One isn’t always going to find an audience that resonates to your style, personal taste in artwork or the curatorial decisions on what I place in my gallery. Read More>>

Andres Freyre

I had a career as a bookkeeper at an armored truck company. Working at this company was stable but sucked the living soul out of me. It wasn’t great for my art and mental health. Read More>>

Ricky Tran

Starting Ricky’s first brick and mortar was the biggest risk I’ve ever taken. Read More>>

Cecille Wright

Adapting to evolving fashion trends and consumer behavior is an ongoing challenge for any entrepreneur. During the COVID-19 pandemic, my business faced significant uncertainty, much like many others. Recognizing the rapid shift in lifestyle and consumer needs, I knew I had to innovate to stay relevant. Read More>>

Emily Dewberry

When I started The Embody Edit, I thought the boldest part would be taking the leap, leaving behind what felt familiar to build something of my own. But what I’ve learned is that the real risk isn’t in starting something new — it’s in staying with it when it evolves, stretches you, and challenges everything you thought you knew about success. Read More>>

Shanaz Ikonne

The Story of a Risk I Took In 2017, I took my first step toward building something I’d only dreamed about a private practice that would make mental health care more accessible, inclusive, and human. At the time, I had no business blueprint, no mentor, and no roadmap for how to build a company from the ground up. Read More>>

Megan Husbands

Rob and I have entrepreneurial spirits by nature, both having started our own businesses. Read More>>

Matthew Almeria

From the beginning, I was always a dreamer. In my teenage years, I had a lot of dreams and goals that I wanted to fulfil, and in my pursuit of those goals I always had chains that dragged me down. A desire for safety, security, and comfort. Fear of stepping out of this comfort zone and into a world of unknowns and uncertainties. Read More>>

Solodoloroze

Oh man hitting hard right out of the gate..I like that haha. Geez man a big risk that I’ve taken lately is honestly deciding to jump into my first ever rap beef. It was a big decision for me mainly because I’ve never been in a rap beef or rap battle before my opponent has been multiple times. Read More>>

Andrea Mathis

When I first had the idea to start *Beautiful Eats & Things*, I was honestly terrified. I was excited about creating something of my own, but there was a part of me that kept wondering what people would think. Would they take me seriously? Would they laugh at the idea of a dietitian leaving her traditional job to blog about food, body positivity, and self-love? Read More>>

Georgia Nubia

One of the biggest risks I’ve taken was moving back to Charleston, S.C in 2016 to be a poet…. I lived in Charleston once around 2007 and it was definitely a movie… a cheap tubi movie that needed a bigger budget and some better actors. I feel like in every way I could fail, I failed twice or more. Read More>>

Kandie Marie

As an author you never know what readers are going to feel when they’re reading a book. I take my time with creating each story, each book, each character; each character is built them from pure imagination, and I fill each book with love. The longer you stay in the industry, the more you want to grow, and you want to expand your reader base. Read More>>

Riley Zwaig

I took a risk when I decided to leave agency work and invest in my own practice. I left a full case load, consistent income, a supportive team and a sense of safety. Read More>>

Florencia Baez

I was nine years old when my mom took me to the theater for the first time. I still remember sitting in the seat, completely mesmerized. In that moment, I knew I didn’t want to be part of the audience: I wanted to be on stage. There was something in that world that made me feel alive like never before. Read More>>

Jude Lutz

Last year I tried this thing I heard about called “100 rejections.” The idea is to try to collect 100 rejections fast. I loved it because it gamified the process of getting my work out there in a way that was fun. It flipped something for me. Read More>>

Miracle Sims

Thus far in 2025, the biggest risk I’ve taken wasn’t about money or business — it was about standing for truth and love in the face of real opposition. For years, I’ve used my platform, God, Sex, and Love, to amplify voices that the world often silences. Read More>>

ROS

It actuality, my entire adult life, post-undergrad, has been a risk. I moved to Atlanta initially post-graduation with $735, no job, knowing few people here, etc…with a hustler’s mentality and a head full of dreams. It was magical (mostly) as a whole…but…definitely came with some SIGNIFICANT challenges for sure. Still, from internships at D.A.R.P. Read More>>

Savy The Creator

Becoming a model, published creative, business owner, show producer, music artist, and author was the biggest risk of my life. It was not just a career move, it was choosing to let the little girl inside of me finally breathe. The one who always dreamed boldly but was told to stay quiet, stay safe, and stay small. Read More>>

Lawdan Shojaee

All good things in life require risk, and one of the biggest lessons I’ve learned is that meaningful growth rarely comes from staying comfortable. A moment that stands out is the leap my co-founder and I took to start the Persian New Year Festival. It began as a simple conversation during a hike in Sedona. Read More>>

Choeunchan Lee

I was only in middle school when my eating disorder reached its peak. Having grown up in Korea, I was constantly exposed to unrealistic beauty standards on social media such as TikTok and Instagram. The pressure to fit that ideal led me into extreme dieting and an unhealthy relationship with food and body image. Read More>>

Jeffrey Barrows

When we both graduated from Marshfield High School in 2002 and later both earned our bachelor’s degree in criminal justice. We both never imagined we would end as barbers back then. Back then, I had a steady job conducting background checks but I was miserable. Eric was bartending at the time, thinking about nursing school. Read More>>

Kari Paine

Over the past few years, I’ve prioritized doing personal photoshoots that just feed my creative soul. This has felt risky, because every second you spend doing unpaid work feels stressful as a small business owner. But these sessions have helped me get back in touch with why I do this job. Read More>>

Coran “BIG CEDRO” Crawford

As far as the music, the whole career journey is a risk. It’s not an easy task to go against the norm so you can pursue a passion, especially in this economy. There’s a lot of distractions out here, whether it’s your own family telling you that your dreams aren’t realistic, or going through life situations that can’t be helped. Read More>>

Vanessa Howland

I quit my corporate retail job where I worked my way up to managing a 80 million dollar plus a year store after growing with the company since I was 16 years old. I worked my way up to Store Manager, but one day I realized the biggest risk wasn’t leaving — it was staying. Read More>>

Michael Dillon

The riskiest and most rewarding endeavors for me are in the public art field. The process of being chosen for a project is quite daunting, as there are so many ways to approach it. You are asked to create a monumental, attractive and meaningful work of art for a community, to last a lifetime! Read More>>

Emily Allison

It was back in 2006, 2007, when I was working as a freelance newspaper reporter, for a few different, local newspapers when I first picked up a digital camera. Newspapers were ‘going out’ as I was trying to ‘come in’. The budget didn’t include hiring a photographer for the stories I was writing, so that’s when I picked up a camera. Read More>>

Alia Rocher

Taking over The Ranch House—now The Rochers at The Ranch House—has undoubtedly been one of the greatest risks we’ve ever taken, but also one of the most meaningful. We have never been ones to play it safe. “Safe and boring” has just never been our cup of tea. Read More>>

Kandelyne Gomez

Honestly everything about being an artist is taking a risk one way or another. The risk of thinking out loud or putting your feelings into a palpable state for others to hopefully see and value…. Posting yourself online for others to critique, judge and admire… Or the risk of still creating even when no one’s there buying your art or supporting it. Read More>>

Sergio DeBari

We started off as just a bakery, but I saw more. I wanted more. So I took the risk. What was once just an over the counter bakery, is now almost a full blown restaurant, with pizza, pasta and even beer and wine. Read More>>

Dr Sharon Arrindell

After many years in the fashion industry, my world was shattered when I lost everything to a hurricane in 1999. As a single mother with two small children, I had to rebuild from the ground up. For a season, I found myself crawling—emotionally, spiritually, and financially—until a dear friend reminded me that as long as I was still alive, God wasn’t finished with me yet. Read More>>

Kylie Truman

When I graduated college, I was certain about one thing: I wanted to work in Advertising and Marketing. My passion for photography, videography, writing and trend research all seemed to naturally point in that direction. I pursued my Master’s degree and followed the traditional path, landing a full-time position at a global, billion-dollar corporation. Read More>>

Heather Hicks

For as long as I can remember, I’ve seen the world through the lens of creativity — colors, textures, and balance have always spoken to me. As a child, my parents encouraged my wildly creative spirit, and every piece of art I created was acknowledged and applauded. Read More>>

Elaine Entenza

I’ve taken several professional risks in my life, including back in 2009; I moved to NYC to take a job with one of the biggest Pilates training schools in the US, only to soon discover the company was not going in a direction that aligned with my values. Read More>>

Flavia Goldenberg

Leaving behind a top leadership role in a multinational with over 140,000 employees — along with the comfort of stability, bonuses, and corporate status — demanded not only courage but a deep calling to follow purpose. I chose to dedicate my path to exploring and mastering advanced energy methodologies such as Genetic Radiesthesia, Energy Healing for people and spaces, and both Corporate and Family Constellations. Read More>>

La’Verne Gardiner

I was at my former place of employment but I knew it was time to leave. If I am honest it was past time. After prayer and consultation with my husband I submitted my resignation. Read More>>