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.

Michele Schalin

In 2017, after 27 years of marriage, I made the bold decision to separate from my ex-husband and start a new chapter in my life. I chose to move to Spain with the goal of improving my Spanish skills. Little did I know that this adventure would not only transform me but also uncover inner strength I didn’t know I had. Read more>>

Amy Han

It can feel terrifying to make decisions outside of your comfort zone, but you can only grow so much when you stay within your bubble. In my case, I took a risk when I started to pursue music seriously. Read more>>

Morgan Mohler

In 2019, I was in the midst of my Bachelor’s Degree in Biochemistry at Viterbo University in La Crosse, WI. I had just left the softball team, and I was trying to figure out what my next big adventure was going to be. I looked into on-campus clubs, events, and music groups on campus, but then I looked up. In front of me, the theater billboard was displaying the final competition for Miss La Crosse/Oktoberfest as part of the Miss America Organization. Read more>>

Radhika Vekaria

Due to a serendipitous turn of events in 2009, I once found myself at a spontaneous audition in the heart of London, prompted by a friend’s suggestion. Little did I know that this singular moment would become the catalyst for my journey to where I stand today. Read more>>

Rebecca Jorgenson

Before starting my own practice (the risk), I had a health crisis after the birth of my second child. I was recovering from a c-section during the pandemic and returning to work 12 weeks postpartum was very difficult. I returned to managing a clinic and a team of physical therapists and chiropractors during the pandemic with the pressure to conform to all the new rules, regulations. Read more

Jordan Willaby

Before I started Willaby Way, I was working as an interior designer for a residential remodeling company. Although I loved my job, I have always wanted to start my own business. During the pandemic, I began working from home, along with so many others, and found I loved no longer commuting and being able to do my work at home. Read more>>

Hal Savar

When I picked up a guitar and taught myself how to play, every time I would write I song it felt magical and like It was a gift that I was supposed to share with the universe. But as the years rolled on, and life was happening to me and around me, I started to feel a little guilty chasing my dreams when I had responsibilities and important people counting on me. Read more>>

Dr. Tammy Delaney

When I think of taking a risk, I envision this to be comparable to taking a “step of faith.” As a young, African American female, I have faced many challenges in life that have attempted to deter me from obtaining my goals as an entrepreneur. Read more>>

Evelyn McCorristin Peters

Over the summer of my sophomore year in college I worked as an usher at an entertainment and arena venue in Philadelphia. Ringling Brothers and Barnum and Bailey circus was the first event I worked. I met several people working with the show and for reasons I still do not understand forty years later, I decided I wanted to join the tour. Read more>>

Irasema Andrade Badillo

Starting my business was a huge risk, I have no idea what I’m doing. All i know is that i want to make stuff. I started trying to sell my jewelry back in 2016. I was going to smaller events and mostly just wasting a lot of money and time, but it was so much fun, and so rewarding. Read more>>

Juliana Sigthorsdottir

I used to work in corporate Fitness at one of the bigger named gyms. During this time I was starting to work my way up the corporate ladder by evolving my skill set from being a personal trainer and moving into assistant fitness manager, with the potential of going into the fitness manager. Read more>>

Jacqueline Gray

I have been a creative person since I can remember my uncle drawing and me sitting asking how he drew such amazing things. He said if I could draw a straight line without a ruler I could draw anything. As i practiced daily drawing that line, I was determined to conquer that task. I did. An artist was born at the age of 2! Read more>>

Kat Sierra

As an artist, it can be tempting to stick to what you know and create works that are safe and familiar. However, taking risks can lead to greater innovation, creativity, and success in the long run. By stepping outside of your comfort zone and trying new things, you open yourself up to new perspectives and possibilities. Read more>>

Cole Burris and Sydney Burris N/A

Sydney: It would seem that our entire relationship together thus far has been full of risk taking! We were friends in a band together for over a year before we started dating in 2019. We really enjoyed our creative partnership and knew we were taking a risk if our dating relationship didn’t land. Thankfully, it deepened what we already had and took us even further than either of us could have hoped. Read more>>

Andrew Sears

The biggest risk I ever took was flying out to LA from Nashville to intern at a studio that I got connected with through a cold email. Back in 2021, I was asking myself the same questions everyone else was. Do I need a new career? Did COVID effectively kill my opportunity to go into music? I quickly decided that the answer was no but that I needed to put myself out there in a way that scared me. So I started doing the thing everyone says not to do and cold emailing composers in LA asking for a job. Read more>>

Jayson Paulino

Embracing self-trust and belief sparked a transformative journey for me. In 2015, I broke free from the stagnation of my life, embarking on a solo expedition to Southeast Asia with nothing but a one-way ticket and a daring spirit. This wasn’t about finding myself; it was a creative odyssey to define who I am. Read more>>

Ryan Crain

In 2018, I was grappling with a big decision of whether to quit my steady and stable job to go see the world. I had an urgent itch to explore, but I just couldn’t seem to overcome this inherent belief that I had to keep my head down, work hard, retire at sixty-five, and then go travel. I was thirty-three years old at that time, and I knew the stoplights of my life would never have so many green lights as it did then. Yet, I hesitated… time and time and time again. Read more>>

Conney Williams

moving to california from shreveport. 1981. i had been in the air force from 1975-79. but i was stationed in my hometown my entire enlistment. i worked as a disc jockey in clubs and a couple radio stations. after a bad breakup, i decided to move to Los Angeles. Read more>>

CeCe Gangemi

When I was a young girl I had always dreamed of being an artist in the “Big City” but knew it was a huge risk that many people didn’t take. These risks never stopped me even though I knew I could fail. In 2018 right after I graduated High School I moved to New York City to continue my journey as a dancer. Read more>>

Alleah Moore

Taking a risk is how I’ve gotten to the point I am today, a seasoned digital content creator with a collective following of 10k supporters across various social media platforms and working with top beauty and wellness brands in the US/worldwide! Read more>>

Alexis Schlitt

I gained my experience in the event industry through many avenues and amazing mentors. From venue management, to event design, to wedding day bridal coordinating! Each person I worked with trusted in me and supported my goals of growing into the industry disruptor I am becoming. I was burned out from working my corporate 9-5 routine, I decided to travel across the globe on a ship. Read more>>

Lara Supan

Taking risks is one of the most important things I’ve seen on the industry side of the music world. Just recently I was faced with having to find a new place to work as my previous agency was downsizing. Read more>>

Olive Huffman

Risk taking is a huge part of how I got to where I am today. One of the first big risks that I took in my career was when I made the decision to niche down from doing all hair services to specialize strictly in hair cutting. Ever since cosmetology school I was drawn to hair cutting over coloring, styling, nails, facials, etc. Read more>>

Mimi Choi

Entering the makeup world was a big risk for me as I had already graduated from university and obtained my early education certificate. After years of post secondary education, training and work as a Montessori preschool teacher, I realized that I was not completely satisfied with my career. Read more>>

Jillian Rigert

In 2014-2017, I was an oral and maxillofacial surgery resident and active duty military member. During long periods of sleeplessness in a high stress environment, I developed pervasive suicidal ideation. In a culture that often stigmatizes mental health challenges, I looked around and it felt like it was just me as not many people were open about their struggles back then. Read more>>

Amy Emde

I was running my business as a mobile swim school for quite a few years. After a while, I was starting to feel the stress of providing lessons at various locations. The frustrating tangle of traffic, rush-hour congestion, and extra planning was becoming a nightmare. Plus, I was paying my teachers to drive between lessons despite the fact that those drive times didn’t bring in any income. Read more>>