You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken.

Brittany Gee

I’ve never been a huge risk taker; I prefer to play it safe and like stability in my life. Recently however, I have taken one of the biggest risks I will likely ever take by starting my own business and launching my company, Revive Functional Nutrition. Read more>>

Kaleb Duggan

Art was always that thing that nagged at me in the back of my head. I wasn’t really successful in my art classes growing up. None of the projects that were presented to the class really inspired me so most everything I handed in wasn’t something I was necessarily excited about. Read more>>

Taylor Stevens

I’d like to think that I’m a big risk taker in life. I never want to look back on moments and think to myself “I should’ve done this” or “I should’ve said that”. Read more>>

Fabius Santos

I feel I have taken my fair share of risks but the biggest one was starting my own mental health private practice in 2020. I had just graduated in 2019 and was working for a private practice and started to become unhappy with my role. Read more>>

Jonathan Shapiro

One of the most significant risks I’ve taken was leaving Mixology Clothing Company, a business I founded and built to great success, at the height of its prominence. Read more>>

Yin Yin Liow

Taking a risk can be exciting yet scary. 2 years ago, I decided to leave the rewarding marketing career I’ve built for 10+ years and moved back to Los Angeles to build an acting career. Read more>>

Romanistan Podcast

We are Jezmina Von Thiele and Paulina Stevens of Romanistan podcast, and every day from the very first day that we chose to work together, we are taking a risk. Read more>>

Kelly Swanson

My entire career has been a series of risks. I always thought I would be more of the “get a job” type than the “start my own business” type. Read more>>

Courtney A. Clardy

My life has been a series of moments where I’ve had no choice but to step out on faith and take risks. The most recent of these moments was during the fall and winter of 2023. Read more>>

Alise Willis

Life is all about taking risks- and I am quite the risk taker. Every piece of my journey thus far has involved some form or another of risk-taking. Read more>>

Dr. Cami Malinski-Gillett

There are so many risks in life. The fear to jump without knowing the outcome is present with each task but there’s an excitement with chasing your desires that spartan kicks you off the edge. Read more>>

Donovan Will

For some, risk is a small step; for others, it’s a life-altering leap. My journey to Japan was the latter, a childhood dream I never thought achievable for a young person of color from South Jamaica Queens. Read more>>

Asha Weal

Starting a photography company and becoming a full-time entrepreneur is an exciting journey, but it involves significant risks and challenges. We all know some of the most common risks are Read more>>

Hannah Phillips

My first job out of college was teaching high school Spanish at the same high school I attended myself. I chose Spanish as my major because I enjoyed the language and culture, and also because I knew it would provide a reliable job as a teacher. Read more>>

Melanie Green

I have always been a creative person and wanted that to be a part of my life. Like many art school graduates, my art had to take a back seat to a job that could pay my bills. Read more>>

Chen Chen

One of the biggest risks and boldest decisions I’ve ever made was when I decided to resign from my job in Beijing and booked a flight to Los Angeles within half an hour. This spontaneous move marked a pivotal moment in my life. Read more>>

Georgia Mitchell

I’ve done plenty of starting over. I approach life like a work of art — when it feels like the current version isn’t working, I’ll try a bunch of revisions, but at some point if I decide the whole scene is off, I’ll chuck that draft and start a completely new piece. Read more>>

Lisa Linger

My educational background is in psychology, biology, and mental health counseling. I earned my Master’s of Science in Couples and Family Counseling about ten years ago and worked as a counselor in a variety of settings from hospitals to the foster care system. Read more>>

Sidney Gage

With many creative endeavors I undertake an element of risk is always involved. Usually, it comes to a choice of quality over quantity, feast or famine, buy now and cry later. Read more>>

Erin Smith

Imagine being burnout from the ups and downs of being an entrepreneur and seeking the current workforce system for support, just to find no support at all? Read more>>

Lisa LaFrance

The two biggest risks I ever took were starting a hedge fund firm and leaving a hedge fund firm. These decisions are discussed in the next section, which talks more “about me.” Read more>>

Michael Biagiotti

After college I was lost and confused because I realized until that point I was living my life trying to do what other people wanted. I decided to throw myself into the “void” and become an artist for better or worse. Read more>>

Ben Phelps

In the fast-paced world of entertainment, where uncertainty looms around every corner, taking risks isn’t just a choice; it’s a necessity for those seeking to make a meaningful impact. Read more>>

Dr. Meshia Miller

The scariest but most necessary risk I have taken was the decision to launch A Chiropractic Hub alongside my business partner and long-time friend, Dr. Dara Geiger. Read more>>

Andy Jo

In 2019 I moved to NYC and quickly adapted my weekend routine to include Saturday visits to the Brooklyn farmers market for grocery shopping and, most importantly, to drop off my food waste of the week – which had spent all week in my freezer. Read more>>

Michelle Poitier

I wanted to share a pivotal moment in my journey that led me to where I am today. After returning from a transformative trip climbing the Andes Mountains in Peru with 10 other military veterans, being the only female in the group, I had a profound realization. Read more>>

Hettie Rich

I went into opening a laser salon without any prior experience in the industry other than as a client. I fell in love with lasers and the many things that they can do to help people feel more confident, be it tattoo removal, hair removal, skin care or scar reduction. Read more>>

Justin Mink

The biggest risk I’ve ever taken is a bit of a double-edged sword: I got sober. Getting sober was risky, as I didn’t know what the future would hold for me, how my life would be different. Read more>>

Brian Tryon

In October of 2023 myself and my business partner opened up a brain child called Shutter and Strum. A community art center working primarily with underserved youth “at risk” youth. Read more>>

Marianna Smith

Almost one year ago, I packed my bags, said goodbye to my hometown of Fredericksburg, Virginia, and drove to Syracuse, New York, to pursue a Master of Fine Arts in Illustration at Syracuse University. Read more>>

Ciearra Tati

At the young age of 20, I became a mother with very little community support. I went from being out with lots of friends all of the time, to being home with my newborn mainly alone. Read more>>

Brooke Sobh

The biggest risk I have taken was quitting my 9-5 job and creating my own business. I was working full time as a clinical dietitian in the ICU, but this was not fulfilling. Read more>>

Milton Matsuyama

My name is MILTON SUNAO Matsuyama Junior, I’m Brazilian, 38 years old and I’ve been working as a music producer and mixing engineer for at least 20 years. Read more>>

Jomil Luna

Embracing Risks: A Journey of Growth and Empowerment I see risks as a series of unknowns and life is a series of risk aka unknowns Nevertheless, each decision is an opportunity to carve out a unique path. Read more>>

Mackinley James

Starting Woobie Sewing was the biggest risk I have taken in my life up to this point. I should preface, I’ve always been interested in becoming an entrepreneur; but, I didn’t quite know the route I wanted to take for the journey. Read more>>