The chapters in our stories are often marked by wins and losses. Getting a new job, getting fired. Getting a life-threatening medical diagnosis, beating it and getting a clean bill of health. Too often, due to a societal expectation of modesty and humility we are discouraged from talking about the risks we’ve taken that led to those ups and downs – because often those risks draw attention to how we are responsible for the outcomes – positive or negative. But those risks matter. Those stories matter. We asked some brilliant entrepreneurs, artists, creatives, and leaders to tell us those stories – the stories of the risks they’ve taken, and we’ve shared them with you below.

Layonda Reason

Taking a risk is a big thing. I have always been a risk taker my whole life. I was the one person in my family that would be person to jump of the cliff to survive. Read more>>

Tiffany Zhou

One major thing to know about me: I used to do venture capital investment. From my very first day, I was taught a tough lesson about risk and rewards. Read more>>

Dominic Jordon

When it comes to being an entrepreneur, taking risks is a given. The first leap of faith started when I took that first step in my journey. It was Spring 2019, and I was in the last semester of my undergraduate degree. Read more>>

Valery Lafontant

I feel like god works in mysterious ways I have always worked since I was 15 . Once Covid hit and my boss getting everyone where i worked sick and him letting most of us go I panicked! Read more>>

Cheyenne Bell

When I was 18, I was lined up to go to the Air Force and right before I was supposed to go to basic training. I decided that I was going to be a hairstylist and an entrepreneur.. Read more>>

Devon Thompson

This music career that I have chosen is taking a massive risk for me. As someone who wants stability in finances, yet a fulfilling creative life, the battle of choosing what I wanted to do with my life wasn’t easy. Read more>>

Vinny Pacifico

Diving deep into a passion/ chase a dream is one of the scariest yet fulfilling things. I took a huge risk, quit high school football to chase my dream of being a professional wrestler, and I bet on myself. Read more>>

Mady Macatula

I believe that the biggest risk I’ve taken in my life thus far is having a complete 180 career change and jumping into something more entrepreneurial. Read more>>

Lori Baudino

My risk taking started when I stomped my feet, expanded my arms, and yelled out my feelings as a young child. My risk taking continued when I pushed back on the dress code of my private school and decided to wear pants instead of the required skirt. Read more>>

Lehua Parker

Back in 2011, I’d just finished a multi-year project and was thinking of doing something completely different. Everything I’d done professionally had an element of storytelling to it, so when a friend challenged me to write a book, I decided a book wasn’t enough. Read more>>

Jaspal Singh

The risk : Transforming Adversity into Opportunity The risk I took wasn’t about physical adventure or financial investment; instead, it was a profound leap of faith in myself. Read more>>

Jennifer Carey

I’m not sure there is anything more vulnerable than singing on stage in front of an audience. Maybe being naked on stage. Still, having something like “our voice” be out there for everyone to hear feels like the biggest risk I have ever taken. Read more>>

Glory Ebinama

In August 2021, I took a leap of faith by leaving Maryland for Los Angeles, seeking personal growth and adventure outside my comfort zone. Read more>>

Annelise Asch

Posting about being happy in a fat body is asking for online harassment. That may seem pessimistic or sad, but in my experience, it has been the truth. Read more>>

Charmaine Broome

I took a leap of faith coming from singing with Kirk Franklin full time, to now being a Master Vending Machine Business Coach. My pivot was scary. Read more>>

Admin Staff

So, it’s less about a risk that we have taken, but rather the one we haven’t taken. At the creation of the project, it was well known that our former president possessed a vindictive streak that manifested into calls for political violence, a trait that foreshadowed the events of January 6th. Read more>>

Deborah Daughetee

I was working as a contracts administrator for a computer software company. I had a 401K, 2 weeks vacation, and my own secretary. Read more>>

Tatiana Velazquez

The biggest risk to take as an artist is to be vulnerable. Vulnerability is the scariest and simultaneously most freeing feeling. I’m in a constant state of vulnerability by putting myself out there with my art and music. Read more>>

Cheyenne Somers

An experience in which I took a risk in my life was when I went rescue a family member from another country with the assistance of the FBI and the local police. Read more>>

Renee Nicholson

I am currently in the risk-taking moment: I have given notice to my employer to devote my time to my creative work. Over the last few years I have manage to save up money so that I can step away. Read more>>

Stephanie Page

Right now we are in the final stages of raising money for a $1.8 million project that will be a social enterprise, Storyteller Cafe. Storyteller Cafe will be a breakfast and lunch restaurant serving coffee as well as a boutique with local products. Read more>>

Rell Godly

Taking a risk in the entertainment industry is always needed. Something different about entertainment is you have people as your sole consumers rather than products to sale. Read more>>

Benjamin Dutill

My entire life, my mother has always told me that I should take risks. But first, always weigh your options. What are the pros and cons of the risk you are taking? In this case, the pros most definitely outweigh the cons. Read more>>

Livelife Lit

Taking a risk is something that’s synonymous with music and business overall. I feel like learning to take risks as as a person evolves is the best thing one could do for his or her self. Read more>>

Kristen Acosta

A former colleague of mine planted the idea of writing a book based on an activity I’ve developed for math classrooms. I wrote a proposal to a publisher of education resources in hopes to get them interested in my idea. Read more>> 

Kendra Baker

When I first became a DJ – I had just lost my underwriting job at Quicken Loans. I had been there for about 5 years, and I was fired for using my wife’s parking spot after mine was taken. Read more>>

Brianna Rojao

Taking risks is something I normally stray away from as a type a (a is definitely for anxiety). I was working at a salon as a sophomore in college and I felt like there was something better for me. Read more>>

Michaela Donahue

It all started with my first big risk. Running down train tracks and sneaking under a fence into a nightclub (don’t do this!) to see what surely became my favorite drum and bass DJ when I was 16. Read more>>

Renae Baca

back in 2009 my boyfriend Shane Stowell owned a Recording studio in Hollywood before I came into his life called QRS STUDIOS. We met at Astro Burger on Santa Monica Blvd 2011. Read more>>

Dr. Cassandra Sanders-Holly

I loved my job. Fresh out of my grueling Doctor of Physical Therapy program at the University of Southern California, I landed the first job I interviewed for, my dream job, working with a county program that served disabled children. Read more>>

Emily Spiers

In the fall of 2014, I unexpectedly went from making soap for my family to making soap for strangers. The shift happened during the Christmas season of 2014 when some neighbors asked if I would be willing to make some soap for them to give as Christmas gifts. Read more>>

AmberLee

Sometimes in life, taking the path most traveled is the easiest way out. Going to college because society deems it necessary, getting that job you don’t love but can bare because you’re afraid of your parents opinions if you follow your wildest dreams instead. Getting a 9-5, because “at least it pays the bills”. Read more>>

Julia Choldzynski

It’s funny to think that if we’d met about 2 years ago, I’d never have chosen this theme to tell an anecdote. I was finishing my second year of a master’s degree in business law, specialising in taxation, and I was going to sit the bar exam to become a lawyer – my life seemed already mapped out for me – but it all seemed unreal, as if it wasn’t really my life, my choices. Read more>>

Olivia Hendren

Honestly, having a business like mine in the South sometimes feels risky in and of itself. Sure there are more liberal areas of our city and state, but for the most part, there are a lot of people in this area of the country who still have a disconnect between “alternative” or “holistic” health practices and having those contradict their religious beliefs. Read more>>

Fran Vives

As a creator, taking the risk of moving to another Country in my mid 30’s where I would start from 0 and leave my safe zone is a challenge I thought about a lot due to all the uncertainties especially when you have a family to support. Read more>>

LaNelle Renfro

The biggest risk I took after opening my first business (Dyvyne Events) was taking on a project that I had NO IDEA how I would complete once the call ended! Read more>>

Barry Jennings

One of the biggest risks I’ve ever taken was starting my own business. It’s a big leap to go from a bi-weekly paycheck to finding your own work and income. Read more>>

Christina Lovelace

I became a registered nurse at 19, tending to numerous patients, managing hospitals, and pursuing a medical business education. Read more>>

Keith Moy

My risk taking started in 1998 when I decided to move from the town I grew up in (Monroe, LA) to Longview, TX. This would turn out to be one of many failed attempts to save my first marriage. Read more>>

Naima Beasley

When I graduated high school I Had a full ride scholarship and an internship that also offered me money towards school. Before I went to school that year I enlisted in the army and was in training for a year. Read more>>