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.

Batu Ozkaner

Starting a career is taking a risk. You don’t know if you’ll end up being good at it, you don’t know if you love it or hate it, and you don’t know if you’ll make a living out of it. I’ve been through this all, and I don’t regret even a bit the day I started making music. Read more>>

Danny Goldfarb

Growing up, I was the model child. I consistently did what I believed was expected of me. I was raised in a Jewish household, with a lawyer for a father who ensured I always did my homework and maintained a diligent approach to school. My grades typically ranged from B to B+, and I was both outgoing and creative. Read more>>

Trina K. Henderson-Torres

Taking a risk, that is the daily life of a business owner. There isn’t a single day that isn’t a risk. You take on all the responsibilities for yourself, your income and the income of your team. The risk of having others’ livelihoods in your hands is a big responsibility and not one to take lightly. I took a risk to open this business after years of working for others. Read more>>

Eden and Jay Trevino

My wife Eden and I, took a risk on starting our grassroots movement, Preciosa Night. It was something that we had only dreamed about. Creating a safe space for our LGBTQ + community to come together and celebrate Culture and Community. Read more>>

Jamie Greenberg

I’ve been a Celebrity Makeup Artist for over twenty years, and it was a job I stumbled into that unexpectedly combined my love of artistry, makeup, and, most of all, people. It was great, but as the years went by and social media started to blow up, I realized I wanted more. Starting my own makeup line seemed impossible. Read more>>

Corey Gossett

When I was growing up south of Indianapolis I would write all of my finished work in a composition notebook that I started my freshman year of high school. I wrote mostly acoustic pop music, your typical singer/songwriter stuff. When I was a senior I put the last page in that book. On the last day of school my notebook got thrown away and I wasn’t ever able to find it and that caused me to lose my passion for music and writing for a long time. Read more>>

Carrie Graham

In founding a non-profit ministry organization, our biggest annual risks come with fundraising season every fall. Somewhere between 40-50% of our annual budget comes from individuals’ donations, and the majority of the rest comes from grants and contracted projects for which we write proposals a few months in advance, then wait to learn of acceptance or not. Read more>>

Ashley Cherney

Hi, I’m Ashley, and I am from a small town in Wisconsin and also attended college at The University of Wisconsin-Madison, living my first 22 years in cold weather, competitive figure skating, and big coats. Growing up, I always talked about moving after college, even changing my major to focus on film and taking summer courses to graduate college a year early. As I realized that my creativity drove my life choices, I set my eyes on Los Angeles as the next jump to explore myself and my creative ventures. Read more>>

Braylon Kennedy

When I was fifteen, I found myself standing at a crossroads, unsure about my post-high school future. The weight of societal expectations and family influences made this a particularly perplexing juncture in my life. My current path didn’t align with my own aspirations, leaving me with a puzzling question: what should I do next? Read more>>

Bryan Young

I’ve been a writer for as long as I can remember, and a filmmaker as well. When the economy bottomed out in the mid-2000s, it seemed like I was doomed and would never be a freelancer again. So I took a steady paycheck, applying my skills to the world of local government and really enjoyed having health care for the first time. Read more>>

Adom Robinson

For me personally, I felt starting Take One was a risk. In 2023, Take One Sportswear is one of the fastest growing athletic apparel and equipment brands in the United States. Widley known for our uniquely customized sports uniforms and accelerated delivery times, Take One has quickly garnered national attention. Read more>>

Quincy Vagell

I worked at several different television stations earlier in my career. Most recently, I was a Meteorologist at The Weather Channel. Although it was a great experience, I decided that I wanted to be out in the field, chasing storms, rather than behind a desk 40 hours a week. Read more>>

Amy Marcs

I believe we grow when we are uncomfortable. When we give ourselves permission to take a risk not necessarily knowing how things will turn out. I spent covid in NYC. Not having left my small Chelsea apartment for over three months. I have always wanted to live in LA, but there was always a reason not to do it. Read more>>

Lwis

Every artist questions, their work. No matter what they may tell the public. So when presenting a new song or product, do you want to make sure that your supporters love it and there’s no way to be 100% certain. So each release is a risk that you have to be willing to take. Just put the product out and if you believe in it enough, so will the consumer Read more>>

Jeri Fonté

Most of the risks I’ve taken have had serendipitous results. The first major one was leaving American Airlines after four years as a stewardess/flight attendant. I left to travel on my own, in what could be called “a year of living dangerously.” With my only contact being the address of an agency that placed young women as “au pairs,” and without knowing much more French than “Où sont les toilettes,” I moved to Paris for six months and became employed by a fabulous family. Read more>>

Tyler Kotch

Opening a Pizza restaurant during covid was defiantly a risk, but with any large risk there is a large reward. Taking the risk I did allows me to navigate my own schedule and run my business on my terms. I was fed up with working for others, producing income for the companies, and only getting a little slice of the pie. Read more>>

Mo Merrell

I took a risk when I chose to quit my fulltime job in 2021 to open a store in the Mall of America. I shared Community Commons space in MOA with 7 other small businesses. I brought my sewing machine to the store and sat in the window sewing day in and day out between 7-10 hours a day, 7 days a week. Read more>>

Bianca Smith

Hello , I’m Bianca Smith and the risk I would say that I took was raising my niece . Between school and working long hours I was afraid I didn’t have the time or patience because I’m a person that always doing this or doing that . And one day I got a phone call and that was the most scariest and upsetting call that I got back in June 2023! Read more>>

Manuel Gamboa

To begin with, since I was a small child I had an incredible love for music but I had not had the opportunity to expand that love because there were not many resources, after a while I had the opportunity to learn to play instruments and sing; I started making videos on YouTube singing and thanks to that the followers began to grow and support me greatly, thanks to this I began to perform in different schools and shopping centers. After a year of doing this, I made the decision to risk releasing my own songs. Read more>>

Kamil Lewis

One of the biggest risks I’ve taken was the decision to go to graduate school. From childhood, I’d always wanted to be a lawyer. I envisioned myself as a high-powered attorney for decades and made educational and professional decisions that supported that vision. After finishing my undergraduate degree, I worked at two different corporate law firms as a law clerk before ending up in the legal department at a large media company. Read more>>

Briana Ramos

I wanted to work with children since I was a little girl. Being a teacher was how I fulfilled that dream for 10 years. The last 2 years I faced lots of struggle from being hurt on the job to the lack of leadership. Having my daughter showed me that I needed to value myself more. Read more>>

Chris Garner

How I stumbled into the fitness business… Read more>>

Molly Cain

A decade ago, I had an accident at my home in Colorado, where I was paralyzed and in a coma. I tumbled down a flight of stairs and demolished the wooden maple table with my face, fracturing the right side. If I woke up from my coma, the journey was unidentified. Read more>>

Isabel Hawk

I started my career in 2017 as an Esthetician in the small town of Grand Rapids; I worked at a salon and spa where the spa was new and just starting. The spa was moving at a slow pace, and I was not as busy as I would have liked. After being there a little over a year, an opportunity opened to work at a salon and spa in Bloomington. Read more>>

Ev Marquee

I’ve always been considered somewhat of a risk taker, outside thinker and someone who does not follow the crowd. From this lens, I have come across many major choice points that have required I take those dreaded leaps of faith. I’ll share a couple. Read more>>

Jude Wallace

took the biggest risk of my adult life last year to pursue music full time. I moved away from my home town, left a relationship that was hindering my purpose, started pursuing a masters degree, quit my full time job and began working on music full time. This all happened within a month or two. I can truly say this was something my soul needed. Read more>>

Velo

As an artist, we take risks every day., that’s just a part of the artistry. There’s one specific risk I took that drastically changed my life, Read more>>

Sierra Emery

I think the biggest risk I took was deciding to begin On Tour Candle Co. with the intention of catering to the interests of a somewhat niche (at the time anyway) customer base. For many years as a female fan of classic rock artists, I have felt like there really aren’t that many ways for me to show my love for my favorites except going to see shows. Read more>>

Grace Schupp

Being an entrepreneur is full of risks every single day but this past August I chose to take a risk that could’ve had make it or break it results. I chose to take the month of August off from work. I stopped teaching, found friends in the yoga industry to take on my group classes and did not open my computer for a month. In the world of solo-entrepreneurship that is crazy. Read more>>

Brady Michael

I’ve always been a firm believer in the fact that when we are uncomfortable, we grow the most. Since I was a teenager, I have always gone for and created projects that seemed a little illogical or made me the slightest bit nervous, because I knew that regardless of the outcome, I would learn something from it. I think the biggest story of a risk I’ve taken that I could offer would be my first full-length show in 2019. Read more>>

Mariah Diaz

A life changing risk was changing my actions. In my life I’ve taken many risks to be where I am today. Read more>>

Abby Dormer

At the beginning of my adult life, I was a young 20-something with a musical theatre degree scraping by weekly to pay my rent in New York City- a familiar story, a common trope, but the desperate truth for many creatives trying their best to make a living. I was no different; this life seemed very glamorous in my teen years, but was decidedly less so while I was pouring boiling water into my styrofoam ramen cup for the 5th night in a row. Read more>>

Kendra Roberts

Blackfish Gallery is the longest running, artist owned and operated gallery in Portland, Oregon. Celebrating its 45th anniversary next year, it is one of the pioneering galleries in the Pearl Arts District, home to many of the city’s blue chip galleries as well as up and comers. One year ago, we vacated a space we had occupied for over 36 years, moving into a new, historically significant building that is three times the size and almost three times the price. Read more>>

Sydney Smith

As someone who is not naturally a risk taker, my art making journey has become the very thing propelling me to grow in this area. Art continues to be an unavoidable theme and desire in my life that I just can’t shake. Pursuing it full-heartedly is perhaps one of the biggest risks I’ve taken thus far and is the very journey I’m stepping into. Read more>>

Briel Emani

For one, life itself is very risky. Anything can happen at any given time… I learned this at a young age just by being observant. The risk that got me where I am today was when I chose to not go back to my job at Macy’s after giving birth to my first born son in 2014. I wanted more for myself and I always had the dream of being an entrepreneur, so I decided to try to make something work that I knew I was already good at. That thing was hair. Read more>>

Krisan Harrison

Taking a risk for me was twofold. The first big risk I took was leaving my country of Jamaica to come to college here in the States. I got my BSc in Biology and a minor in Psychology. I followed a very traditional path. That is, getting a degree, then getting a job, I wasn’t fulfilled. I had always been curious about skincare. Read more>>