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.

Rosemarie Kwong

During 2023, I took one of the biggest financial risks in my career. Looking back upon it, I’m glad I did because it reaped rewards that I was hoping for and did not expect. In February/March, I spent a substantial amount of money on 1st AC gear. I bought a wireless video transmitter and receiver, a monitor, and the wireless follow focus I had my eyes on for months. Read more>>

ALLAZEA MARTEL

The biggest risk I have taken was quitting my 9-5 job to solely focus on my business and perfect my artistry. I have quit a lot of jobs. The reason for me quitting and stepping out on faith; is because when I would be at work all I could think of is ” I could be selling my own products” ” I can take this time and create content and etc. Those thoughts alone would literally eat me up mentally. Read more>>

Andrew Campbell

Before I was licensed massage therapist, I was a retail pharmacy manager. I had a salaried position in the nation’s largest pharmacy chain, that provided guaranteed pay, benefits and opportunities for growth within the safety of the health care industry. Why would I want to leave that? Read more>>

Sunshine RA

One of the biggest risks I’ve taken so far is moving to California and staying during the pandemic. After graduating college and being in the field for a year, I changed my plan to go to medical school and left. I wanted to do something different, and California provided the opportunity to both remain in my field and test the entertainment industry. I come from a small town, big family, and other than the money I saved to move I was on my own. Read more>>

Alyssa Lalla

The biggest risk I took was creating my business. When I came up with the idea of having my business I was just 16 years old I started out doing makeup, but then Covid hit and I was working a regular 9-5 job. When I turned 18 I was going to college, and still working a regular 9-5 job. I decided to take a risk and start practicing lash extensions, at this time I was not doing makeup consistently so my business wasn’t running.  Read more>>

Pamela A Torres

I would have to say one of my big risks was entering art into this annual event called Valentween. It’s a romantic goth exhibit that is arranged every February on the second floor of the St. Pete Art Lofts by Brandy Stark, a wire sculptor and teacher who has a passion for the paranormal (as well as her adorable pugs!) I consider this a risk because I live in New Port Richey and, in retrospect, making it to St. Petersburg was an exhausting chore. Read more>>

Paige Hoover

Taking a risk is probably one of the scariest thing to do as a creative. Even more so, they just get bigger. Taking the first leap of faith is definitely a hard one as you have no idea how it’s going to turn out. It’s something you have to learn to be okay with, no matter the outcome. Whether it be an audition, casting, traveling for a job, working with a new company, or even attempting a new skill… the risk is always worth it. Even if it’s just a lesson learned.

John Valles

Creative work in the modern context is characterized almost entirely by risk. • You risk criticism. • You risk rejection. • You risk mistakes. • You risk disappointment. You don’t have to risk everything, though. If you can afford to be creative, most of the risks you can take aren’t that high-stakes. Read more>>

Amanda Waters

One of the most life changing risks I’ve taken was starting my aesthetics business. When I moved back to Phoenix, in 2013, I was working at a small local waxing studio trying to rebuild some sort of clientele in a new city. Clients were curious about my work history, as any new client would be when you’re having someone new working on you. Read more>>

Angelica Menor

I come from a small town , Stockton, California. Nothing really to do besides “make” fun. Most of my memories in my head that replay consist of my always intoxicated absentee father and how I never wanted to be around him. To be honest with you I have no recollection of us ever having conversations where he was sober. But then there were moments where his smile would shine through and he’d pick up his guitar, strum something and say something silly. Read more>>

Chelsea Whitman

I started my business about ten years ago, more as a side hustle, shooting mainly family members and past coworkers. When I started my business, it was a different name that, at the time, meant a lot to me, but I decided to rebrand in 2022 after my father’s passing and my son’s birth. My new business name, Dietz Creativez, is a nod to my dad. When my father passed I made the decision to jump in with both feet and just go. Being a full-time creative is not always an easy thing, but it’s always fun. Read more>>

Jacinda Soto

I took a risk in 2019 during covid. I started to teach classes on instagram live on my own. Many things could have went wrong, but I didn’t let that stop me. I went the route of being positive. Dance has played a huge role in my life, and i wanted to take action. During covid I was able to reevaluate my goals and what I wanted in life. I always say if it wasn’t for covid what would have happened? Read more>>

Willie & Fionna Porter

During the pandemic and the social justice uprising, I began listening to podcasts as a way to escape what was going on around me. The more podcasts I listened to, the more I started feeling inspired to give it a try. So, I began doing research on how to start a podcast. I indulged in as much information as I could. I looked at how much would it cost to get started. Read more>>

Nasir Figueroa

I’ve taken many risks in my life, some bigger than others. I believe taking risks is important because you never know what will happen until you try. Success often comes from learning from mistakes, so taking risks can be a good thing in the long run. One of the biggest risks I took was deciding to focus on my career full-time, without letting anything hold me back. Read more>>

Steve Seidel

Growing up, the world seemed massive. However, with each day that passed, I was able to understand that we are all connected in one way or another. Eventually, I started to realize that the power of connection, was my superpower. Read more>>

Theo Elwell

Being a professional artist in any capacity is an inherently risky decision. Everyone has to sell something in order to make money and pay the bills… Whether that’s selling your time, your services, or in our case – our art. This presents a paradoxical scenario when embarking on a career as an artist, and begs the question ‘Do I make something which will appeal to the masses and has the most chance of making money, or take a risk and produce something that is authentic, hoping that it will be a success?’. Read more>>

Alex Poppe

I woke to the wail of New York City sirens, assailing the streets. Outside my bedroom window, clouds drifted zoologically over squat, repurposed factory buildings in the early morning light. Rolling over on my air mattress, I was greeted by a steady, hissing whisper. The mattress had deflated almost to the laminate hardwood floor. The toilet flushed, the bathroom door clacked open, and the ZZ Top-bearded man from whom I sublet the bedroom padded down the hallway, probably scratching his belly. Read more>>

Caitlin Love

Starting my own business is by far the biggest risk that I have ever taken, I never dreamt that it was something I would have done or even wanted to do, but it kind of came out of necessity. When I was 27, I had been in my own home for about a year that I had purchased, I had a truck payment and a decent job that I was happy at. The place that I was employed at was giving me more challenging projects and more responsibility, and I was really enjoying the tasks. Read more>>

Jacqui Lauko

Entering into a field that is experiential (not research-based) was a huge risk. Investing several thousands of dollars in an equine-assisted therapy certification along with $1000 in liability insurance annually. Not to mention the 1000lb horses which cost a fortune to feed and maintain (they are like children). I did all of this in 2010! I didn’t even have any equine clients lined up or even a job that would let me do EAP once I gained licensure. Read more>>

Denzel Hill

In a way, moving to Savannah was a risk. I was offered a job that casted a great vision of longevity and my overall career development, yet it did not go as planned. In hindsight, there were plenty of unknown factors that I should have taken into account when considering my relocation from Maryland. I could have taken more time to understand the town that I was moving to, who I was set to work for, and develop a strategy that would allow for professional agility in case of unexpected happenstances. Read more>>

Elizabeth Dowland

The biggest risk I’ve taken was abandoning a stable career path to pursue creativity. Since I was a little girl, I always knew that whatever career I chose for myself, it was going to allow me to be expressive and creative. My dream was to be an author for quite a long time, with storytelling being one of my greatest passions – from writing whimsical short stories to thrilling graphic novels. It wasn’t until I was about to go into high school that my direction really changed in a surprising way. Read more>>

Kaitlan C. Farrior

Among the risks I’ve taken, one stands out as the most significant: transforming my dreams into reality through writing and publishing books. Initially, the prospect of putting my thoughts and creations out into the world was daunting. My first book felt like a leap into the unknown, filled with uncertainty and self-doubt. However, despite these fears, I took the plunge and published it. Read more>>

Kat Roe

The biggest risk I have taken was starting my apprenticeship and leaving behind what I knew and what I was used to. Starting my tattoo apprenticeship was something that took so much focus and determination, adjustment and a lot of learning. I went for over 2 years barely making money. Read more>>

Erik Fellows

Picking up moving from Maryland where I grew up to NYC when I was 20yrs old to follow my dreams in entertainment and then after 1yr of living in NYC and after the tragedy of September 11th 2001 and then yet again made another move but this time it was to Hollywood to continue on my path in entertainment! Read more>>

Rickeyia Lolla

My most challenging risk was my family and I moving to Los Angeles, a city that was unfamiliar, but familiar to us. I was always intrigued with fashion, beauty, and music. I knew I possessed an eye for fashion and style, I thought, why not pursue fashion styling? Before moving to Los Angeles, I was a military wife and mom of three. Read more>>

Becka Rahn

As artists, we are risk takers by nature. It’s not the same kind of thrill-seeking risk as jumping out of an airplane or wrestling alligators, but it’s a series of little risks every day putting your art out there into the world. I feel like every day you make a new gamble: Will this piece get juried in or rejected from the exhibition? Will someone buy this from my Etsy shop so I get paid today? Read more>>

Dan Alex

In October of 2021, I had just quit my job, was living in a rundown apartment with every pest infestation you can think of (yeah, even that one), severely depressed, and had no idea what to do next. I had only attempted stand-up a couple of times since coming to Atlanta and the results were NOT reassuring. Read more>>

Oscar Granados

I had Owned a few other businesses prior to Scottsdale Collision Center, The one right before this one took 4 years of blood sweat and tears. At the end of that for a number of different reasons and many of witch I couldn’t control, we had to dissolved the business. this really took a toll and I thought this is where I draw the line as an Entrepreneur. at this point at had been going at “owning my own business” since I was 21 yrs old, at the end of the last business I was 34yrs old. Read more>>

 Jennifer McCabe

In many ways beginning a career in the arts is a risk. Without a definitive path, one must chart their own course. What I have learned is that it is important to look for opportunities even when they appear to be risks. I was 34 years old when the first chance to run an institution as director and chief curator came my way. Read more>>

A. R. Redington

Probably the most significant risk I’ve taken was quitting my full-time job, on two separate occasions, to pursue my author/freelance career. In 2014, I quit my full-time job as a graphic designer at a newspaper firm to finish and publish my first book, The Esoteric Design. I had attended a bookstore where authors and poets gathered to do live readings. Read more>>

Adam Gaines

I’m a writer/producer in town. Written on a few TV shows and had a couple movies produced. So when the first friend I made when I moved here seventeen years ago told me over drinks that he was interested in taking his comedy game show from a web series to a live show and I found myself offering to help, it was (and to this day continues to be) a risk. Read more>>

Sabbie Narwal

Leave no stone unturned…that’s an idiom that’s always stuck by me. A long time ago, when I was very young, being an artist and small business owner felt like the most natural thing in the world. It wasn’t long, of course, before those dreams were quashed by a world that believed that to be an artist is to suffer and be destitute. I eventually put the artist career out of my mind and replaced it with what I thought was the perfect compromise: interior design. It was creative but came with a salary and clear-cut career path. Read more>>

Tracy Holt

Recently leaving my full-time corporate career to pursue art full-time. Historically, I would describe myself as fairly risk averse. Always following the rules and safe path that we are ‘supposed’ to follow in life…graduate high school, go to college, get a full-time job based on the major you graduated with and the list goes on. Read more>>

Robert Newman

One of the biggest risk I’ve taking to date has been leaving my job on wall street, to pursue my art career full time. Read more>>

Shreyas Makam

Several years ago, I found myself at a crossroads in my life and career. I had been working a steady job, but I was yearning for something more, something that would allow me to pursue my passion for food and Indian cuisine. It was during this period that I decided to take the biggest risk of my life – quitting my job and fully committing to opening my own restaurant, Makam’s Fresh.Indian.Fast. Read more>>

Jeremy Lux

When I decided to start Illumine in 2016, launching in 2017, I had no idea the risk I was taking. To me it seemed simple – I had a passion for the outdoors, traveling and the adventure that came with it – I just needed to find a way to share that passion with others and help them experience the same thing. Read more>>

Chaysen Beacham

In short, simply moving out to LA. I come from a small town in NC so to move to one of the largest city’s in the world was at best unpredictable. Breaking into any industry is tough, but I think making a name for yourself in one that doesn’t necessarily have a clear path to success or “corporate ladder” is very daunting. Read more>>

Cristina Mormorunni

In March of 2022 I co-founded INDIGENOUS LED. I had a secure job, but the world was cracking open around issues of equity and justice. I recognized that this was the moment to bring every creative fibre of my being to the task of re-imagining what our relationship to the natural world could/should be. INDIGENOUS LED exists to protect, heal, and celebrate our wild relatives and their homelands. Read more>>

Erica Taylor Sanders

When I first started Taylormade Counseling Services in 2015 I was 30 years old and had no idea what it took to run a business. What I had was work and educational experience that allowed me to interact with people of all races and economic statuses. That experience taught me time and time again about the disparities that exist in minority communities that prevent them from having access to services that could change the trajectory of their lives. Read more>>

Toyosi Sanni

I feel like everyday is a risk. A risk if you’ll live up to your full potential or not. A life changing risk for me creating the type of music I make. Being boring in America & my identity being Nigerian I had to really find myself within the music. I explored sounds & took influences from Sade to 2pac to Wizkid. Read more>>

Rebel Kitty Kunzite The Glitter Alchemist

I feel like I took the biggest risk of my life when I quit my dog walking business to pursue the arts full time… but I mean some would say even attempting to start my own dog walking business was a risk within itself. I don’t like being told what to do and I definitely don’t like being underpaid which is the norm as an employee in Amerikkka. Read more>>

Nikki Rung

Taking a risk?! Oh this is definitely taking a risk. There is no guarantee in gig life- its risky. You just have to keep putting one foot in front of the other and keep pitching yourself to EVERYBODY! Sometimes I feel like I’m crossing that line but I think everyone close to me now knows that I will not pass up an opportunity to share with anyone that will listen to me about what I do. I carry business cards with me all the time…. *just in case!* I happen to get into a conversation with someone that might be interested in what I do. Read more>>