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.

Felix C. Arroyo

One of the biggest risks I’ve taken was leaving a good paying job for a job that payed way less but offered me more time so that I could focus on my podcast and quality of life with my family. Read more>>

Zeinab Saab

The biggest risk I have taken was choosing to be an artist. I think there doubts among many people surrounding me, but something told me that nothing else would satisfy me in life. It look a long time to get where I am at. I first started out as a photographer when I went to college. Read more>>

Scott & Stephanie Shangraw

Scott and Stephanie have always been risk-takers. Pursuing the arts full-time was a pretty easy decision. They rely solely on their artistic endeavors since they are a husband and wife team. Read more>>

Jessica Hawks

Starting my business felt like a GIANT risk to me. Prior to starting, I was in one of the worst spots of my life. I had dropped out of college, was 20k in debt, working 60+ hours/week and couldn’t afford therapy which I desperately needed. Read more>>

Lexa Goldman

Despite my passion for seeing clients in private practice, I always worked a full-time job as a therapist, whether it be in a non-profit agency or school system, in order to have the security of consistent income. Read more>>

Connie Toavs

I take pride in my roots in where they’ve led me to today. My father is a farmer and I’ve enjoyed being able to grow up in that environment. Agriculture has always been close to my heart and in my roots. Read more>>

Ashley Baylor

The greatest risk I’ve taken was investing in me. I know that sounds crazy. 2023 was the year I did everything that scared me. I created a writing journal for black men, I networked with career professionals in my dream field (physical therapy), and I started my own business. Read more>>

Hannah Saunders

In 2020, before the world shut down, I did the most incredible solo road trip and drove from Jackson Hole to San Francisco and then down the entire coast of California. Read more>>

Nicholas Rhodes

Between 2015 and 2017, when I wanted to move away from being NickyDigital, I realized I’d have to take a major risk if I wanted to continue to be challenged and successful as a creator. Read more>>

Antwan Perry

For those of us who have the opportunity to pursue higher education, many times, it seems that our paths are chosen for us. We go to college, pick a major, and depending on what we are studying, we choose a career path, internship, or advanced degree based on that particular major. Read more>>

Jane Nicholson

Starting my videography company, Arrow & Knot Productions, at the age of 19 while still in college was a huge risk. However, at the time it felt more like second nature. Read more>>

Sarah Teubner

I have always enjoyed performing. A few years ago found me with full-time professional job in education, mother of three, side hustle entrepreneur, but with no real outlet for my performance creative side. Read more>>

Charlotte Grimm

I had a bit of a rocky start to getting into the arts as a career. I knew I wanted to pursue an art degree but I was discouraged to do so in high school so instead I took a year off, moved 1000 miles away from my hometown to a town in Colorado, and worked odd jobs in the food service industry until I figured out what I wanted to do. Read more>>

Nata Galati

I can’t imagine what my life would be like if I didn’t take risks, feel the pressure squeezing me tight and breath into the uncomfortable places that my gems are hidden under. I have always been a risk taker: a woman thinking, walking, talking and feeling outside of societal norms. Read more>>

Kryssi Jeaux Miller

Quite a few risks were taken along the road to founding the Knights of the Tempest in 2016. The sport of jousting is dangerous and hard. Performing with swords and other medieval weaponry similarly requires much training and practice to do it as safely as possible. Read more>>

Pakiza Munir

I came into this world during a time when the dark shadow of Taliban rule cast a long, suffocating pall over Afghanistan. From my earliest memories, my mother’s words painted a vivid picture of their brutality, particularly for women like us. Read more>>

Brittany McMahon

In 2021 I left my first “big girl” job in corporate America at a Big 4 Accounting Firm to join a small social media start up here in Dallas. It was my absolute dream job and it honestly sounded too good to be true! Read more>>

Abra Kadab

My move to Los Angeles in October of 2015 is the biggest risk I’ve ever taken. Before my move to Los Angeles, I lived in Denver, CO. My “past life” was very settled and, for the most part, very predictable. Read more>>

Kim Anderson

A domino of risks lead me to today. It all started when I was accepted to attend a writing and running retreat in Bend, Oregon hosted by Olympian Lauren Fleshman in May of 2020. Read more>>

Evelyn Sprigg

I was burnt out. From a long, draining career in big marketing agencies. From not listening to my gut, my heart, my body for too long. I left the agency world and I had everything — and nothing — in front of me. Read more>>

Sarah Bossio

The short story? I quit my tenured, secured, full-time public school teaching job. The long story? I had been in the special education classroom for almost 15 years and was starting to feel the burnout creep in, which only multiplied when COVID hit. Read more>>

Mylo Stone

My biggest risk in my journey as a creative was to let go of preconceived ideas of what my journey would look like. We are fed my societal norms that the life of a creative should some how be monetised and industry success is the parameter of you being valid as an artist. Read more>>

Katie Wiggins

When I moved to LA in 2010, I was fortunate enough to be able to transfer my position from my previous corporate salon employer in Detroit. Moving across the country to start a new life no doubt includes major risk in itself. Read more>>

Yo It’s Jojo!

I have taken many risks to create a life that I am happy with and proud of. My whole life has been about “change” as I didn’t take the “normal” route because I had a vision for myself. To be the person that I want to become and create the reality I want, it required me to be out of my comfort zone. Read more>>

Legin

About 10 years ago I decided to leave my job as a youth pastor and a pursue a full time career as an independent faith bases/positive hip hop artist and professional speaker. Read more>>

ALIZA1K

Being Myself in front of the whole world. Online everyone feels entitled to their opinions and hateful comments or views on how someone should look, dress,live, etc.. Read more>>

Elissa Jane Mastel

Going back in time, I’d like to tell you about one of the biggest failures I had early in my career, and what I learned from it. In 1993, my then partner and I embarked on producing a music festival in Vermont. Read more>>

Mikayla Prioleau

Don’t be afraid to take risk. I took a risk when I first graduated college and applied for a job that I was not fully qualified for, but I knew that I could do the work and do it well. Read more>>

Alma Rojas

I believe the biggest risk of all was starting! I had this idea of starting making mini doughnuts as a hobby fueled by pregnancy cravings but seeing the potential and how much people really liked the concept my 36 well pregnant self just took a leap of faith by starting an actual Facebook page and initiate this mini donut business thinking I would just wing it while it lasted… Read more>>

Kaylen Ross

Risk-taking is something I never really partake in outside of the artistic world. In school I would always stay between the lines, follow directions, and never question the rules given to me. Read more>>

Daphne Pollard

Taking a leap of faith, I teamed up with an associate to kickstart The Co-Lab Collective. It all started when Ossie my now business partner, dreaming of her coworking space, explored spots in downtown Montgomery. Read more>>

Kathryn and Sarah Griest and Peterson

It was 2019 and the buzz of the election was all around. My friend Sarah and I were feeling like we wanted to speak up and make an impact about a topic we both feel passionate about…women’s reproductive freedom. Read more>>

Tony Vallejo

As a creative we tend to be our biggest critic. Whether we fully believe in what we are doing or even if it is “good enough” taking a risk is one of those things that we you have to do in order to chase your dreams. Read more>>

Emily McCracken

I’ve always had something inside me that was creative. Throughout my life, I tried MANY different outlets, singing, dancing, poetry, song writing, painting (and the list goes on) and none of them felt like they fit. Read more>>

Amy Schuber

Ten years ago I started a podcast without really knowing what a podcast was, it was scary and risky. Ten years ago, it wasn’t as common as it is now. It feels like everyone has a podcast now, which actually isn’t true, just feels like it. Read more>>

Luz Valencia

I grew up in South Central, Los Angeles in a small house with five older siblings. My mother was a single parent who, on a minimum wage salary, somehow managed to take care of all of her children. Read more>>

Carrie Boone

Taking risks has always been anxiety provoking for me. Growing up with an introverted personality, taking a risk has always been the last thing I’ve wanted to do. Lesson by lesson as I grew into womanhood, I learned that if you take no risk, sometimes you get no reward. Read more>>

Kat Gaffney Jellicorse

I originally started out doing musical theatre and allowing other people to write the script for me and my career. I had always written my own music but was genuinely convinced that it wasn’t that good and that no one would want to listen to it – to say I was terrified is an understatement! Read more>>

Melody Godspower

I have always wanted to be in the artistic world but I never guessed in will be the path I am currently on. As a graduate of software Engineering, I think it’s safe to say choosing a musical career or running a business in fashion and writing ,was a very high risk to take especially when you have no idea how far it could take to get to where I need to be. Read more>>

Marla Mase

Well, first off, I want to say that everything we do is a risk. Life is a risk. Every second of every day, a risk… Falling in love is a risk – looking at yourself in the mirror – a risk Becoming a parent — “You become an asshole when you become a parent.” Read more>>