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.

Arrington Foster

Growing up always having a passion for acting I knew that it would come a time where I’d have to make the decision to leave my hometown in Maryland. So after college and a few years of work a few side jobs I decided to make the big move and go to Los Angeles, CA. Read More>>

Margo Redfern

Farming is, by nature, an outrageous risk. You wager time, sweat, and your savings against weather, pests, markets, and luck. The average farmer in America is now over 60, and only about 13% of farms survive on farm income alone. Each year, we lose roughly 2,000 acres of farmland per day nationwide—an entire landscape slipping quietly away. Read More>>

Saberra Massey-Hill

I took a big risk when I decided to stop treating phlebotomy like “just a job” and turn it into a full business and a school. I didn’t come from money, I didn’t have a big team, and I didn’t have a guarantee that people would trust me with their training or their healthcare needs. Read More>>

Lori Coremin

About 14 years ago, I took a risk that still feels a little unreal when I look back on it. I started my own concert photography company, War Child Photo. It honestly all started with a camera I received, a small point-and-shoot camera, as a Christmas gift while I was in high school. Read More>>

Alexis Rose

I launched my home based floral studio at the beginning of the pandemic in 2020. I had been a floral designer in another shop since I was a teenager and when the pandemic hit that business closed its doors. I needed a way to keep working while also maintaining safety for my family, so I started by doing micro-weddings and no-contact deliveries from my home. Read More>>

Charissa Bates

In the summer of 2019, I was diagnosed with a rare and aggressive cancer – Triple Negative Breast Cancer. During that time, I had to reflect deeply on what was important in life and what was taking up space in my head, heart, and time that wasn’t productive. Chemo, surgeries, and constant unknowns flooded my day-to-day life. Read More>>

Francine Juhlin

I loved my career as an aircraft electrician fixing aircraft for the military. The work felt alive in my hands. I thrived on the precision, the problem solving, and the purpose that came with keeping aircraft safe. When my health declined, everything shifted. Being a female aircraft electrician for the military was my identy. When my health declined, everything shifted. Read More>>

Alycia Clark

I always envisioned myself being a painter. To me, there is nothing more peaceful than getting in the zone and painting a masterpiece. I know the term “starving artist” doesn’t exist for no reason though. I always shied away from taking my art seriously as a career. I looked at as a hobby instead. Read More>>

Charles Grundas

For many years, I was just an accountant by trade, but I was also a heavy smoker, heavy drinker, heavy person. I was living a life that was going downhill fast, and I knew I needed to change. My first risk was small: I quit smoking and became a runner. Read More>>

Alejandra Harguth

THE JOURNEY THAT BROUGHT ME HERE For 27 years, I lived my personal life on a foundation that felt unshakeable. And for nearly 20 of those years, my professional world mirrored that same certainty—as a federal investigator, built on stability, structure, and a clearly defined path. I shaped my identity around that promise. I gave it my loyalty, my time, my energy, and my health. Read More>>

Trevilia Hodge

I took a risk that didn’t look like a leap — it looked like a highway. It was a quiet decision, but it roared in my spirit: packing up what little I had less than $1000.00 tucked in my pocket, and driving down I-95 from New Jersey to Texas, alone. No job lined up. No roadmap. Read More>>

Dianne Lacefield

Being the daughter of an artist, I was raised in a creative environment. I took art lessons from my dad and observed him taking risks which turned out well for him. I did many art projects along the way but I worked in the printing and marketing fields during my career. Read More>>

Carisa Downs

So, when I was 18 I opted out of traditional college. I took 2 years at a local community college to get my basics, and then I started photography with a cheap camera and zero skill. Read More>>

Jay Lauck

The Risk That Changed Everything The Moment I Bet Everything on Myself It was 2023, and I was staring at a decision that terrified me: should I invest thousands of dollars I didn’t really have into laser engraving equipment for a business that didn’t exist yet? I had no customers, no experience, no safety net. Read More>>

Nathan Ross

One of the biggest risks I ever took was walking away from the “safe” path and choosing to build my own brand — not just to make money, but to build a legacy my kids could inherit. I went all-in on myself long before I had recognition, partnerships, or momentum behind my name. Read More>>

Michelle Folsom

I am not a born risk-taker. I thrive on stability and reliability. And yet… Once I started a family, I started wanting more flexibility and autonomy of my schedule. So what did I do? I shifted from a very predictable schedule in outpatient physical therapy to the beginning ideas of opening my own private practice. At this point, I had no business training. Read More>>

Angela Landeros

A Business Built on Healing I went from being independent to growing my business into a multiple therapist operation. Massage therapy has always been more than a career for me. It was the craft that helped me understand pain—my own and others’. Specializing in pain management and injury recovery wasn’t just a business decision; it was a calling. Read More>>

Kimberly Laughlin

After nearly 20 years in the marketing/advertising space, I was laid off. (This year – 2025) As someone who has always played by the book, this was never part of the plan. Changes in agency structures and the AI explosion has really changed the landscape of my industry. So I decided to try it on my own. Read More>>

LaKisha DuCreay

One of the greatest risks I ever took was betting on a vision only I could see. Years ago, before La’Creays was a recognized brand, before the luxury menus, corporate events, and curated cocktail experiences, I found myself at a crossroads. I was working jobs that paid the bills but didn’t fulfill me. Read More>>

Mackenzie Shilling

When I first start doing hair 7 and a half years ago I never would’ve imagined that I would be the owner of my own salon one day. I took a risk and ran and I will never look back from it because it was the best decision I ever made. Read More>>

Frances Samson

At 19, just after my first year of university in Toronto, I was given the opportunity of a lifetime. I was personally invited to audition for the world-renowned Limón Dance Company. I jumped on a Greyhound bus, walked into the audition, and walked out as one of the youngest members in its 70-year history. That leap is what brought me to New York. Read More>>

Josue Quintero

One of the biggest risks I’ve taken was choosing to step away from the safety of a consistent 9–5 job to pursue filmmaking full-time. At the time, it felt like standing at a crossroads between security and calling. I had a stable income, benefits, and a predictable routine… but I also had a dream that refused to stay small. Read More>>

RAMÉ

Immigration was one of the biggest risks I’ve ever taken. I was studying music in Chile and the opportunity to come to Montreal to study jazz presented. I didn’t think about it twice. I had been dreaming about leaving to pursue my dream, so I did. I took all my belongings and left my family, my friends, my territory, my life. Read More>>

Victoria Cvitanovic

I used to be a prosecutor. Now I help people establish compliant businesses in psychedelics and cannabis. I left criminal justice disheartened by drug policy in America. So many people I thought should be patients were being prosecuted in one of the most wealthy, technologically advanced societies in the world. Read More>>

Nikolas & Julia Krankl

All signs pointed towards making a career working for my parent’s winery – Sine Qua Non. In 2012, I did just that. Got to work, cut my teeth and learned the trade from the best in the world. Read More>>

Yaretd Alcantara

Hello, my name is Yaretd Alcantara, CEO and founder of Glamour Studio Enterprises, and I’d like to share a story about a major life-changing risk I took: the decision to open my own business.’ In 2017, the risk I took was investing all my life savings—my entire security net—to open Glamour Studio. Read More>>

Sarah Pratz

The risk of farming- is it worth it? That’s the big question, huh? Truthfully when we first started out, me and my boyfriend knew nothing. We were young, and in love, and in 2014 he said… “Let’s get some chickens!” To which we got a dozen chickens. Which then sprouted, “Let’s get ducks! And goats!” And the journey began! Read More>>

DeAngela pippen

I took a break from my career to focus a year on starting my business I’m still successful as of 2025 Read More>>

Dr. Brooke Fantin, DPT

Taking risks… ironically, the concept of ‘taking risks’ has been coming up a lot recently in my daily writing practice. ‘I say that I am open; but how open am I really? Read More>>

James Selu

In February 2024 I officially stepped away from a stable 16-year career and launched my own financial planning and asset management firm, Palm Coast Wealth. It was the biggest risk I had taken in my life/career. It was not easy to walk away from a stable career and knowing there was a chance that I could fail, but I did. Read More>>

Sergio Hodar Pla

For me, being a creative is all about taking risks at every turn. When I was 18, finishing High-School, I still didn’t know what to do with my future. I remember wanting to be an engineer all of my childhood, to mimic my Dad. Read More>>

Martha Burich

A meaningful risk I took was walking into a county jail for the first time to work with addicted and alcoholic women. I’ve never been in jail myself, and I had no idea what to expect. I only knew that something inside me kept telling me to go. It wasn’t comfortable. It wasn’t familiar. Read More>>

Varsey Laurelle

Entrepreneurship is the biggest risk of all. Once you make that risk, to not get a ‘reliable’ check every two weeks, not have people directing you on what to do, there’s just a whole bunch of associated risks that come with that in your duration of entrepreneurship. Read More>>

Dr Catrina Grigsby-Thedford

One of the biggest risks I ever took wasn’t loud or dramatic. It was a quiet moment—just me, my pain, and the truth that I couldn’t live the way I was living anymore. After more than a decade of addiction, instability, and over 100 arrests, I reached a point where I didn’t recognize myself. I had survived so much, but I wasn’t living. Read More>>

Rang Tan

The greatest risk I have ever taken as a restaurateur was the very first one: choosing to open a restaurant in Las Vegas—a city famed for its food and hospitality—without any formal culinary training or prior restaurant industry experience. Read More>>

Heather Gugliotta

A risk I took that completely changed the trajectory of my business—and honestly, my creative confidence—was the moment I decided to build Dolly, my now-signature 8×8 disco-ball wall. What makes it even wilder is that Dolly didn’t begin as some big, ambitious project at all. The original idea was simply to create a small piece of art to hang on my wall. Something cute. Read More>>

Len Noe

Most people talk about taking risks as if they’re clean, simple moments, switching careers, moving somewhere new, starting a business. My biggest risk wasn’t any of those. I chose to turn myself into the research. Several years ago, I made the decision to selectively augment my own body for the purpose of offensive security research. I have implanted 11 microchips into my hands and arms. Read More>>

Chante Pantila DBH, LPC (CA-11292)

One of the biggest risks I’ve ever taken was choosing to build a career that honored who I actually am instead of who I was told to be. I started my practice because I wanted to create a space where high-achieving women—especially BIPOC women—could feel liberated, inspired, and deeply supported. Read More>>

Fendi Despres

The most impactful risk that changed my life was the abrupt decision to move to Aurora, Colorado from Albuquerque, New Mexico in 2014. My mom, stepdad and younger sister had moved to Aurora a couple years prior. My sister has autism and my mom is her caregiver. Read More>>

Kellie Roesler

I have been around horses my entire life. My mother was a barrel race and showed halter class. My father used his horse for hunting. Both gave me a love of horses and helped me understand the versatility. Even with all my exposure to horses I never thought I would be running a business that was centered around them. Read More>>

Kate Ellen

I think we have it backwards when we talk about risk. We celebrate the bets that paid off – the gallery that said yes, the investor who came through, the leap that landed perfectly. Those stories make us look smart, like we had some inner compass guiding us to the right choice. But that’s not really how risk works. Read More>>

Yeonjoo Kim

As one of many international students who moved abroad, leaving behind my beloved family and hometown, I can confidently say that my biggest life changing risk began the moment I arrived to U.S. Read More>>

Miss Primrose

One of the biggest risks I ever took was choosing to fully bet on myself as both an artist and an entrepreneur, at a time when stability would have been the “safer” choice. I had already earned my degree in psychology and was on a traditional path that made sense to everyone around me. But creatively and spiritually, I felt unfulfilled. Read More>>

Dr. Tiesha N. Bryant

One of the biggest risks I’ve ever taken was choosing to share my story openly and honestly about being 13 and pregnant and the woman I eventually grew into. For years, I carried a quiet fear of being judged. I worried about how people would view me, and I worried about the impact it might have on my daughter. Read More>>