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.

Christian Covington

Anytime one goes beyond the systems and structures designed by society, they concurrently risk their reputation and comfort. I (she/her) identify as a Black, queer, woman who embraces authenticity and utilizes style and fashion to express it. Although I am comfortable expressing myself through fashion now, this was not always the case for me. Read more>>

Alexander Novicki

One thing that gets me fired up more than anything is hearing the term “Keep your day job”. Read more>>

Willie Johnson

I’ve decided to retire from my current day job. The goal is to put my full support into my business, personal, and professional goals of being an independent digital artist and producer. Read more>>

Rodney Damon Collins

When I think of the word “risk” I have learned that there’s an element of risk in everything we do. When you graduate from college (if you decide to go) there’s the risk that you will not receive work in your chosen field. When a couple decides to marry, there’s the risk that things won’t work out. Read more>>

Cindy Kennedy-Gomez

In this industry, most of the women are somewhat younger than me. A part of me felt that I had to keep up with them physically to continue and it was exhausting mentally! I put a lot of pressure on myself. I suffer from anxiety and panic attacks so this would make it even worse. Read more>>

Cesar D’ La Torre

i ALWAYS LIKE TO TAKE RISKS, wHEN I decided to become an Actor, it was a challenge, but also a risk I have to take, moving alone to the capital of Venezuela when I was 18 years old, and before moving I was traveling 12 hours at night by bus to get to Caracas Venezuela in the early morning just to be part of a scene with one line and then travel again back the same day, Read more>>

Sofia Stefou

The most daring leap I’ve ever made was my relocation from Toronto to Los Angeles. At a glance, the two cultures may appear identical, yet delving deeper reveals distinctive mindsets, attitudes, and values that required adjustment. Read more>>

Jamelle Zablow-Moloney

It’s funny how life divides your roads and forces you to choose in ways that set you up for future success, unbeknownst to our current, in-the-moment selves. Before I decided to enter into my Bachelor’s and Master’s studies to become a teacher, I struggled to find a career option that would both support my curiosity of Spirit and help me financially support the family I eventually wanted to have. Read more>>

Dr Eric Holmes

As your journey life you may be faced with taking a risk. Most afraid but you must learn to look at things from another perspective. Just understand that when taking a risk make sure your risk has a purpose. In life you may never move foward unless you take a risk. Read more>>

Skit Karter

I was in the hood down bad, fresh out of jail thinking to myself what am I going to do now? I didn’t wanna work for anyone anymore, I always felt disrespected as an employee & knew it wasn’t for me. Then one day it hit me, “You have everything you need to set a studio up. Read more>>

Kawika Hoke

Starting a film and TV production company from scratch on Maui, I don’t know anything riskier. It’s not only the most expensive economy in the United States, but it’s also the toughest housing and job market. But I know if I didn’t take the risk, no one else would. Read more>>

SinThya The Devil

Music and art in general is all about taking risks. Not everyone is going to love what you make, hell, most people won’t even give a shit. That’s why you make art for yourself. The people will come. Read more>>

Kenan Amori

At 19 years old I took my first risk with writing and releasing music about my personal life in my songwriting. Since I was 13 years old I always had songs about my relationship with God, my complicated love life, my insecurities, and family issues. Read more>>

Mark A. Lembo

As an artist, you face risk in everything from the first brush stroke, to putting the finished product out there, to making sure the bills get paid so you can continue the journey. With that risk, though, can come great freedom and even joy. Read more>>

Fatell

Following a creative career path hasn’t been the easiest road. I started my creative journey at 15 years old where I began blindly pursuing a life where I would be living my dreams and making a living on what I love to do. After overcoming many years of struggle, I developed a I will not lose mentality. Read more>>

Daelen Cory

As an interior designer, I had been searching for an idea for a product design I could create and sell. During the pandemic lockdown, I found a Visual meditation app called Mesmerize. I had guided meditations, soundscapes, and very trippy visuals one night. Read more>>

Casey McDougal

It was September 2017 and I had just finished working on a feature film on the east coast, when I decided to take a trip out to Los Angeles. I knew I wanted to live there, but this trip was meant for me to look around and figure out the city a bit. I was planning on moving sometime in the spring. I drove around, met up with friends, and just took it all in. Read more>>

Kendra Newhart

After deploying out of the country for a year away from my two young daughters, I returned home determined to be with them as much as possible while still maintaining our life and home as a single mother. Read more>>

Krisiz Jay

The first risk I ever took as a creative was the very first music video I put out I had no prior music. No one listening. But when I made it I wanted to put it out and just see what happens. Never did I think about what would happen after that. And since 2019 it’s slowly but steadily getting better with every passing moment Read more>>

Jeff Betten

I’m required to take risks every day as part of my job – every artist signed by a record label is inherently a risk! But some are bigger risks than others. Let me tell you a story about one of my prouder decisions, though: Read more>>

King Dari

. Last year around this time, I took a huge leap of faith and entered into a competition for a chance to go perform in Miami. I was scared. Terrified because I didn’t know if taking this risk would pay off. When I arrived on the Miami beaches, I realized that me taking that leap and trusting myself did pay off. Read more>>

Eric Sierra Marrero

Well that’s an easy one. Read more>>

richard purnell

The pro wrestling business is all about taking risks. taking risks on yourself, in matches, and in big career changing moves. in June I’ll be leaving the country for the first time in my life. I’ll be traveling to Europe for a whole month to wrestle with some of the biggest companies over there. Read more>>

Julian Oyanedel Santiesteban

I believe life is about taking risks in order to comply with your convictions; this mentality has stuck with me since a young age and embracing uncertainty in order to achieve my goals is what has brought recognition to my career and respect for me as a person. I grew up in Chile, where the opportunities to shine doing what you love and thriving are basically non-existent. Read more>>

Missy Kershaw

My entrepreneur journey started in college, I packed up my life and bet on me. In 2016/2017 I had finished my first two years of undergrad at a juco and decided to move to a new city to go to a university in a city where I didn’t know anyone other than my boyfriend. I also decided that when I went to a university I wouldn’t work. Read more>>

JoJo Guevara

I have always wanted to work with big production houses as a collaborator. It was the entire reason I went to film school and began my journey down the digital cinema path. I felt that if I was apart of those high profile companies, then I would feel truly accomplished and accepted among those I had always looked up to. Read more>>

Ashley Lacy

Deciding to start sharing my music has been the best decision I ever made. I had been writing songs for a few years but had never seriously considered doing anything with them. However, when the pandemic struck, it compelled me to delve into that creative side of myself. Read more>>

Ginger Britt Daniels

I have been in the entertainment industry in some facet for a couple of decades now and I believe that living a full life that is rich with experience, good or bad, hopefully both helps creatives to have a better perspective with taking risks. A risk can be a scary endeavor, but if you don’t try, you’ll never know, will you? Read more>>

Cameron Gilmore

In 2019 I had pitch the idea of starting a company with part-time college students with little to no business history. The first run at building the company failed bad..really bad. What I learned from that, made adjustments and in 2020 the birth of the company happened. In 9-months we did $34 million. Read more>>

Grace Bors

One year ago my life looked very different. I was engaged to a man who made me cry more than laugh, I was isolated from the people that made me happiest, and I worked at a job without benefits and no possibility of growth. I settled for this life; I thought I was meant to live in mediocrity. Read more>>

Stephanie Maier

Before Covid we were doing mostly wedding cakes and dessert tables but once lockdown started all of our events were being cancelled. There was a moment of major panic but I told myself to give it a week to see what would happen. Within 6 hours I had a menu up for people to order family meals for contactless pickup or delivery. Read more>>

Guy Holmes III

Being a creative you’re going to have to take a lot of risks. In the beginning you will have to invest you time and money into your vision, and you may not receive any help but that’s okay. Most people won’t see YOUR vision, which is perfectly fine, but keep going and don’t stop till you see it through. There will be nights you won’t sleep, Read more>>

Bhroovi Gupta

Leaving behind the familiarity of India, I embarked on a daring adventure that would change the course of my life. The risk I took was to journey to America, a land filled with opportunities and uncertainties, with the sole purpose of pursuing a career in graphic design. Read more>>

King Judah

It’s said that if you don’t take the risk, you’ll lose the chance. I feel that I’ve lost so many chances at achieving greatness due to internal fears, self doubt, and public opinions. I can assure you that taking risks is a necessary action when looking to elevate in life. When I first relocated to Georgia, I started in the public safety industry. Read more>>

Ashley Michelle Miller

If we think about it we all take some sort of risk every day. It is part of life. But I now know it is truly a blessing when you take on life-changing risks. My biggest life-changing experience happened about 13 years ago. I decided to release the desire to be a people pleaser and started the journey of listening from within and discovering what I wanted for myself. Read more>>

Gina Tang

Trail-blazing is inseparable from risk-taking. Going off the beaten path means risking one’s footing, so to speak. It challenges whatever concepts of security, stability, and sometimes safety that a person has held. Read more>>

Vanessa Nank and Maribel Mesina-Geib

We can both agree leaving our 9-5 jobs and opening our own business was one of the biggest risks we’ve taken. We came to a point in our lives where our priorities shifted and our well being took the forefront. We walked into the unknown but in our hearts knew this was the best move for us. Read more>>

Sherree Rogers

I kept telling myself that I’m going to walk away from my job and spend my time helping people. Everyone thought I was crazy because I was leaving a paying job to work for free. I had no idea how I would pay my bills or if I would love my job or not. Read more>>

Masho Margishvili

During my teenage years and early adulthood, I embarked on a quest to find a creative pursuit that would truly inspire me, to which I could entirely dedicate my efforts. While I found designing intriguing, I always knew there was something out there that would bring me true fulfillment. Read more>>

Mecca Hunter

So I’ve taken many risks in my life but I feel like one of the biggest ones I had taken was leaving my job at Home Depot as a paint mixer. I really held that job tight for a very long time (well to me a year and a half is a long time but you get what I mean). Read more>>

Kevin Abril

As a teenager I fell in love with cars and knew I wanted to be part of that world. After high school I meet my mentor who was crazy enough to work on a design that I had for my car. working next to him I learned a lot on design process, materials, procedures, etc. From there on I decided to take a risk and pursue designing automotive exterior parts. Read more>>

Brittney Kilgore

Creating a non-profit without initial funding is the BIGGEST risk I have ever taken. I had no idea how much time, money, and effort went into creating this business. While I was creating this business, I was constantly thinking about the legacy I wanted to leave my children. What type of events I wanted to host? The purpose. The reason. The why. Read more>>