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.

Mario Quintero

There have been many risks throughout my career and one major thing I’ve learned is that taking risks, though in the moment might be tough and scary and even seem like a terrible decision, in the end they are the most rewarding. When I was 27 I moved to San Diego from Boston where I attended Berklee for a few years before realizing college wasn’t worth the money when trying to be a musician or engineer. I had the idea to build and run a recording studio from scratch with my bandmate Mike. Read more>>

Deborah Crowley

Fifteen years ago, I embarked on a transformative journey that led me to leave the corporate world and establish Exclusive Cleaning Services. The catalyst for this pivotal decision came during a reflective walk around the office, where I found myself surrounded by the individuals I had personally onboarded to the company. As I observed their experiences and interactions, a realization dawned upon me – the desire to break free from the confines of Corporate America and pursue a more fulfilling path. Read more>>

Emily Barresi

I fundamentally believe in taking risks. You have to as an artist. If you’re not an artist, I still think you should jump head-first into what scares you. Of course, protect yourself where you can. Try not to put yourself in financially dubious situations or environments that are unsafe for you spiritually and creatively. But remember there will always be another day to work. Another day to tweak the art or self-correct. Read more>>

Lauren La Bella

I can honestly say that as a full-time creative I have taken several great risks in my life that have all been extremely scary but also pivotal moments for me as far as reaching the next level. The one that comes to mind in this instance would be taking the initial plunge into the tattoo world. When I graduated from college, I began working as a freelance photo editor for a couple publications. This was a great experience but I knew that ultimately I wanted to make a living off my art and tattooing had been calling me for some time. Read more>>

Amanda Held

“One of the most defining risks I took was the decision to start HOOVES. It began with a deep, personal journey. As a veteran myself, I grappled with the challenges that come after service – the transition back to civilian life, the search for purpose, and the need to heal from invisible wounds. I found solace and healing through my connection with horses, which inspired me to think bigger. Read more>>

Arthur J. Davis

I recently took a risk with writing a short film as well as producing and acting in it. Originally the plan was to apply to as many grants as possible to help finance the film; I applied to over 40 grants without receiving a penny. When something like that happens it is a very hard pill to swallow. A reality check. It messes with your head and starts to make you question yourself, your vision, your creativity. Read more>>

Kelsey Eide

Before I knew how to read, write or to tie my shoes I had a great idea of what I was meant to do here on planet Earth. One of my clearest childhood memories was looking into the mirror as I watched myself softly singing into a faux rose I was using as a microphone. After my mom finished helping me practice a piece from my beginner piano book, I rewarded myself by composing my own song, a simple tune not more than twenty seconds called, “What a Nice Day”. Read more>>

Jun Osaki

I’ve taken a lot of risks in life, following the steps of my mother who decided to immigrate us to the US. One of the biggest risks I’ve taken is choosing art as a career path after high school instead of something more traditionally stable – I almost went into psychology and pharmacy work. Within my tattoo career, moving workplaces has been a major theme with lots of risks – the unfortunate thing about the tattoo industry is that it tends to be filled with large egos and therefore lack a community or accountability. Read more>>

Emmanuel Amido

Although comfort is wonderful, it frequently has a hidden cost that comfort’s greatest tool fails to reveal. We, all 8 billion of us, are made to serve a purpose. That purpose might be to knit the best sweaters to ever come in contact with human skin or to be placed in the same ranks as the knowns like Dr. Martin Luther King Jr. or the unknowns like Sophie Scholl. Most of us fall somewhere in between knitting and life-costing activism. Read more>>

Darryl DJ DLIFE “Payne”

I was working a 9-5 job with the aspirations of one day diving full-time into my career of djing & entertainment, but that had to be something I would need to plan for because I was a single dad raising two young children. My job at the time would allow 2 weeks vacation a year and as a rule I would’ve taken my vacation around Miami Carnival (October) which give me the opportunity to make some extra cash doing something I loved with the benefits of my 9-5 back home on my return, or so I thought. Read more>>

 

 

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