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.
Frank Reteguiz
In the summer of 2020, I decided to pursue writing as a full-time career after I was laid off from my job with Tesla during the pandemic. Prior to that, I was on furlough during the Spring and it put things in perspective for me and how much I working for a corporation and how much I truly love storytelling. Read More>>
Shannon Lazovski
For over two decades, my world was defined by clicks, conversions, and the relentless pace of the digital landscape. As a social media strategist and digital marketer, I lived on the front lines of an industry that is forever changing and intensely competitive. Read More>>
Elyse Flynn Meyer
One of the most defining risks I took was starting my own marketing consultancy in an industry where leadership tables were, and often still are, dominated by men. At the time, I had a strong career, a growing reputation, and a clear understanding of how marketing could drive real business outcomes. Read More>>
Kyara Ofuani Esq
One of the biggest risks I’ve taken was choosing purpose over predictability at a moment when most people advised me to play it safe. After law school, I did what I was “supposed” to do. I had credentials, elite training, and doors opening that would have led to a traditional, stable legal career. Read More>>
Sophia Kohler
The risk I took didn’t feel dramatic at the time, but it fundamentally changed the direction of my work. I’ve always been interested in fashion, but as I learned more about the industry, particularly its environmental impact and labor practices, that interest became uncomfortable. I started to realize how much of what we wear depends on systems most consumers never see. Read More>>
Brianna Nonnon
I made a giant change in career path after jumping into esthetics right after highschool. I was working part time while going full-time to esthetics school. Read More>>
Ruoyun Killian
At 23 years old, I took the risk to run my own social media agency, C3nami. It was a simultaneous act that scared me absolutely shitless and felt 10000% right. That feeling meant I was stepping outside my comfort zone. Read More>>
Rami Kalla
I remember when I had my first big boy job out of college and I was very honored to receive the position that I did at a big Fortune 500 company. However, about 2 years into my job, I had become disenchanted with the work and the company. I had always had the dream of starting my own business and I thought why not now! Read More>>
Chris Heuisler
I knew – since the age of 12 – that I wanted to be an actor. I loved the stage and working with actors to tell a story and make an audience FEEL something. Right after college (Penn State, ’01) I took a risk: I went to California with one suitcase and one meeting with a casting director through a friend’s connection. Read More>>
Ken La Salle
I work as an independent author because I have a lot of dreams to fulfill. I don’t believe in bucket lists, which puts me on a ticking clock. I wrote my entire life, as I tried to fit into the corporate world, but didn’t invest in writing full time until 2012, so I’m relatively young for an old author. Read More>>
Kelsey Webster
The biggest risk I’ve ever taken was starting up my freelance work, and it’s also been the best decision of my life. During my last semester of college, I took a film photography class and I haven’t looked back since. Read More>>
Rebecca Martin
Many people dream of lives where they have more time, flexibility, and overall freedom. However, acting on dreams, ideas, or opportunities always comes with risk. When I decided to leave my job and start my own business, I was terrified. I knew in my gut it was the right thing for myself and my family but fear can be paralyzing. Read More>>
Micah Crée
The first risk I ever took happened when I was just three years old—when I discovered that I could sing. That may sound small, but it was actually the beginning of everything. Something I’ve never openly admitted is that I was scared of my own voice and how far it could take me. Read More>>
OGONNA
Pursuing music and becoming an artist was one of the biggest risk I’ve taken. The risk pushed me to go against cultural standards. The risk forced me to go within myself and answer tough questions that challenged my growth. Read More>>
Michaela Kennedy
I’ve taken a lot of risks in life: most of us have. Many artists and creatives experience a similar crossroads in their lifetime. It’s the risk of believing in yourself and pursuing your art full-time or continuing on a different, much safer and dependable career path. Read More>>
Tiffany Hanchett
The biggest risk I’ve ever taken, both personally and professionally, was choosing to step into the unknown simply because God called me to. My business, Faith Over Fear Coaching, was born from that exact decision. The name isn’t just branding; it’s the story behind everything I do. Read More>>

