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.

Hope Chapman

I took a risk on me in 2018 when I took $200 and invested in my travel business. I was working 12hrs in the health field and one day I was on Facebook and seen a post that said “Who wants to own a Travel Business” and I have always wanted to travel the world, so I commented on the post not knowing that I had to invested in this business but I had got tired of working for someone else and making them rich. When I took a look at the business overview it was a no brainer it just made since to own my own travel business cause I was already traveling. Read more>>

Susan Rubin

Aaron, thanks for inviting me for an interview. As a children’s book writer I face many risks—spending time on a proposal for a subject I think kids will enjoy, yet not always convincing an editor that it’s a worthwhile project. A particular risk I took was in writing outside of my culture and race when I did a YA biography, Sing and Shout: The Mighty Voice of Paul Robeson. Read more>>

Eric Rimmele

Well, You don’t take the risk they will be no “reward”… I totally agree, however “reward” comes in very different ways. You win big, great, you might struggle for years to get there or you simply loose. In my opinion, ESAY money does not exist. Really nothing in-between. For all the risk takers out there, here is the beginning, you take your life, professional and private, to a level that you did not anticipate. Read more>>

Vinh Nguyen

In the early months of 2010, I made a life-altering decision that would define my path from then on. After dedicating three years of my life to a corporate job at AT&T, I found myself at a crossroads. The role that once held promise had soured, leaving me deeply unsatisfied. The commission structures were shifting, and despite pouring my heart into the work and aspiring to an assistant manager position, it remained elusive. Read more>>

Melissa Papel

Life is all about taking risks, if you ask me! I was born and raised in Paris, France, and just after graduating from middle school at 15 years old, where I was bullied and miserable, I told my parents that I hated France and needed to go as far away as possible. As big world travellers, my parents told me that the furthest I could go, geographically speaking, would be Australia. Next thing you know, I packed my bags and moved to Sydney, on my own, at 15 years old! Read more>>

Roosevelt D. Patterson

Starting the journey of sharing my life story in my book about some challenges and experiences. Being vulnerable and transparent has been a work in progress for me not knowing how my book would impact others. I realize that everyday is a risk in some format. So I started talking thing out with my wife to make my experience as a example how to overcome hard times in this life. Read more>>

Luke Storey

I started in the entertainment industry in the early 1990s in Hollywood as a musician. I grew up on Rock n Roll, so I moved to the city at 19 and jumped head first into the local music scene. Although substance abuse issues limited my success at the time, I did have some meaningful highlights along the way. Over the years, I had the opportunity to play alongside some of my childhood heroes from bands like Motorhead and The New York Dolls. Read more>>

Veronica Njodinizeh

The biggest risk I have ever taken is putting myself first and starting my own business. Let me be clear when I say ‘putting myself first’ is not from a self-centered ‘its all about me’ mentality. No matter what your personality type (I’m a consul), there has an innate desire for me to get to know my strengths and weaknesses for myself and walk in the purpose God has for me. Read more>>

Christine Nguyen

The biggest risk I ever took in my life was opening my own practice. I’ve always known I wanted to have my own clinic. From as young as 13-14 years old I would tell people, “I’m going to open my own clinic one day for kids with autism!” So the idea was manifesting quietly in the back of my mind for years to come. Read more>>

Chianni Powell

Healing is a big risk. Surrendering into the unknown as you delve into and unearth the darkest parts of self that have been buried and forgotten for years is an unexpectedly and yet entirely necessary risk. Read more>>

Adwoa Duncan-Williams

Starting my career as an actor was one of the biggest risk I’ve taken thus far. Packing up, moving from everything I know and was comfortable with to pursue this dream was something I knew I had to risk. It was vital I took the risk to move to New York to become an actor because of the grind of the city. It was what I needed to jolt myself into the industry properly Read more>>

Heather Harvin

In full transparency, I was one to rarely take risks. I would lean more to playing it safe because that resulted in consistency. Then one day, I was challenged, by a mentor, to start taking risks because they would ultimately lead me to my destiny! I haven’t looked back since… Read more>>

Mark McKee

I took a risk by moving to Los Angeles in 2013 with no job, barely any friends there, and only a dream and a mission, I was living and working in Raleigh, NC as the owner and engineer at a recording studio I had since age 21. I knew I wanted to work with the best musicians, artists, and creators in the world, whatever it took. When I arrived in LA the first few years were incredibly hard and I was sometimes broke and depressed, but I also knew I had to be there and learning so much so fast. Read more>>

Kate Kincaid

Every year at SWLF feels a little bit like taking a risk and that started with our very fist year. Sara and I had traveled to another conference on polyamory and it was great but we thought, we could do this and add our own spin on it. Neither of us had ever run a conference and we didn’t know what we didn’t know but we decided to go for it anyway. We wanted to start small but this conference has a mind and heart of it’s own so it had other plans. Read more>>

Scott Hersch

I’ve always wanted to be in the restaurant business, since high school. I knew it was a bad idea, hard work, competitive industry, most fail, no formal training. Read more>>

Kai Eckhardt

The biggest risk I ever took in my life was to become a professional musician. The story goes back to the year 1973 when I had a key experience that made me fall in love with music. I lived in Germany at the time and had just entered high school in the city of Mainz. One day my class mate Christopher Schneider invited me and a few friends over to his house to show us how to rig a conventional stereo system into a guitar amplifier. Read more>>

Dylan Storme Smith

Within my story lies a captivating tale that traverses continents, crosses oceans, and bridges cultures. It is the story where I embarked on an extraordinary journey, leaving behind a familiar landscape and venturing into the unknown, driven by a profound desire for a better life, a risk that I took. From the challenges of leaving one’s family and friends behind, adapting to a new culture and way of life to the bittersweet yearning for the sights and sounds of home, this story paints a vivid portrait of the immigration experience. Read more>>

Jordan Padilla (Meek)

The biggest risk I’ve taken was moving to the US from Australia to study at Berklee College of Music, where I attended on. I was fortunate enough to have been able to attend on scholarships and grants that I auditioned for. Growing up in the Condell Park and Campbelltown areas of Sydney, I never thought pursing this kind of dream was a possibility. Read more>>

Donna Sheratan

What your parents did right. Read more>>

Earnest Marshall

I took an extraordinary risk by moving to California with no job, all for the pursuit of their acting career. Against all odds, they chose to follow their passion, leaving behind the familiar and venturing into the unknown. Read more>>

Chaslyn Reynolds

Relocating to a new city involved a lot of risks, yet it was a decision I felt was necessary for growth. I was at a point in life where I felt like I did everything I could do in my hometown (Paris, TX). Days were passing without purpose, and I had a feeling of not fully living or being in a space where I could reach my full potential. Read more>>

Bruce Languren

Starting a business as most business owners will tell you its not much of a challenge, mechanically speaking but the it is self decrementing. Let me explain. Read more>>

Tamara Miller

I always dreamed of living in Los Angeles. That’s where all the action takes place! I knew that’s where I needed to be in order to grow and expand my career. I often travelled back and forth for conferences several times a year. After some time however, it was clear that I had to make the move in order to pursue my dreams. I had to take the risk. Read more>>

Marlissa (Mars) Herring

The most significant risk I’ve ever taken was packing up and moving to sunny San Diego, which meant leaving behind my family and friends in Chicago. At the time, I was working part-time for the Chicago Bears, a role I deeply cherished. I had also recently completed my Masters degree at Northwestern University and my Bachelors at The University of Chicago. Read more>>

Heather Wiest

“Appreciate you for joining us today. Risk taking is something we’re really interested in and we’d love to hear the story of a risk you’ve taken.” Read more>>

Drysen Carsten

Ah, I love this question. I’m looking back on my career, I’ve consistently put myself in seemingly emotionally and mentally risky situations. In high school, I was terrified of social interactions, along with public speaking. To overcome it, I intentionally ran for State VP of the South Dakota Future Business Leaders of America, which obviously, required being social and public speaking. Read more>>

Holly Brown

While I was attending Esthetic school I got a call from my Dr. that all the lymph nodes in my lungs were enlarged to an alarming size. They had seen the lymph nodes on a routine MRI I had because in 2000 I was diagnosed with Multiple Sclerosis. After having a surgical biopsy, I was diagnosed with Sarcoidosis and because I now had 2 autoimmune diseases my form of treatment was changing. Read more>>

Jonathan Redavid

I personally chose this specific panel discussion topic because it reflects my general life style. My life it’s all about taking risks. Read more>>

Shane Guffogg

I think just the mere act of being an artist, and by that I mean wanting to dedicate a certain amount of time to expressing yourself., is a risk. I say this because our society doesn’t really promote self-expression and especially in the form of the arts. I was drawing as soon as I could hold a pencil and by first grade had been plucked out of the group as the class artist. Read more>>

Chris Lawrence

To be honest, starting Cactai Agency was one of the biggest risks that I’ve ever taken in my life so far. After being laid off in Feb 2023, I knew that I never wanted to be in that position again. While I didn’t love the work that I was doing with the company, I knew that I deserved to be working in a field where I could wake up every day and do work that I was genuinely passionate about and felt I was properly compensated. Read more>>

3250 mondo

The biggest risk I ever took was jumping on plane and flying down to Houston with nothing but about 130 dollars to my name I had my 1 year old son with me and his mother. We didn’t have money or anything I invested all my money into two artist TEC and Honcho yolo both from Baton Rouge Louisiana apart of click called spider gang. Read more>>

Linny Monteiro

Relocating from Brazil to settle in a foreign country, miles away from my family and childhood friends, and venturing into a place where I wasn’t fully proficient in the language, all at the age of 20, marked the most significant risk I had ever undertaken in my life. It had always been my aspiration to become proficient in English and attending a university in the United States stands out as one of my most significant achievements. Read more>>

Hermes Baroli

I was born in Brazil where I grew up as a dubbing actor. My parents used to work as actors and dubbing actors. One day, while I was following my mom during a dubbing session, the director asked me if I’d like to try recording my voice to dub a boy in the movie “Superman IV”. I was 10 years old at that time. I accepted and never stopped dubbing anymore. Read more>>

Angie Kim

While working as a physician in the hospital setting, I began noticing little things over time that pointed towards the toxicity of the working environment, such as how little control and autonomy physicians have in taking care of their own patients, the backstabbing from other healthcare workers, and how physicians from other healthcare systems all had similar stories. I came to the realization that this would not change if I just changed jobs. Read more>>

Raeykwon

I feel like it’s been all or nothing specially since the beginning of this year. I feel you aren’t truly chasing your dreams until you’ve doubled down and you’re all in. Getting on yourself is the biggest risk with the highest reward. Telling myself “this is who I am” and not settling for a life of lesser. It’s had its ups and downs too and I’m still figuring it out. Read more>>

Lara Popkess

Being an artist may seem like all fun and games, and it truly is, until the need for financial stability arises. The world often fails to provide a conducive environment for creatives to thrive economically, despite the essential role we play in society. Creative expression distinguishes human beings from artificial intelligence in an increasingly technological society, yet artists frequently find themselves with the short end of the stick and expect to only pursue art as a hobby. Read more>>

Betsy Lane

It’s always hard to be in business and is always a little risky. I have been in business for many years and one needs to be ready for changes. In the last 40 years I’ve experienced many changes including the invention of the computer. Read more>>

Yvonne Camper

6 years ago I quit my six-figure corporate job to launch a business I did not even know I had. I just knew there was something more for me to do in this world and my life had a greater impact than what I was presently experiencing. I had one goal in mind when I quit and that was to write a book that I had been working on for several years and the urgency to finish it was haunting me. As a wife and mother of five, I was investing in myself, which I had not done for a long time. Read more>>

Andra Watkins

Every written piece should be labeled “Taking a Risk.” Even when a piece is not autobiographical, our stories reveal hidden bits of the creator. Read more>>

Will Dudla

When I was a little kid I loved to read and collect the Sunday paper comics. I would also spend hours reading comic strip books like Peanuts, B.C., Calving and Hobbes, The Far Side, etc. It was, along with 80s cartoons, what inspired me to become an artist. I drew all through grade school, then high school, and finally through college to attain a Bachelors in Fine Arts. Read more>>