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.

Leah Ferezan

I was a wedding planner for 14 years and I loved it. I started out in college taking marketing and wedding planning courses. Then I interned with a wedding planner for year before becoming an assistant and helping day-of. Read more>>

Dale Blankenship

You have to take risks, you have to risk your normal life, relationships, jobs, and even respect, at least that is my experience. It is a risk to believe in yourself. Read more>>

Keri Welch

After spending 25 years working as a licensed physical therapy assistant and having a steady income and job, my husband encouraged me to take a risk to start my own business. Read more>>

Matt Chessco

I quit my engineering career 4 days after getting my first job. In the summer of 2018, I finished my Mechanical Engineering degree. I got my last exam on a Saturday and I started working the next Monday. Read more>>

Susan Richards

Ever want to try something new but fear holds you back? Doubt creeps in? Questions of doubt flood your mind? What am I doing? I don’t know how to start? Who am I as an artist? Am I good enough? How do I portray myself to the world? Etc? Read more>>

Nathan Robles

When we “take a risk” we’re pushing through the boundaries of what we believed was possible. When we don’t take a risk, it’s because we have a compulsion to stay where we are familiar. Read more>>

Susan Hohlman

Life is series of choices and those choices lead to being a calculated risk taker. The best gift my mother taught me was to be a calculated risk taker. She would say to me when I was young…” Read more>>

Tionta Witherspoon

8 years I stepped out on faith because Delta didn’t want to give me my benefits. I was tired of building up everyone else’s job but I was treated like I didn’t matter. Read more>>

Alistar

Risk taking is essential to the wellbeing and growth of any individual with a dream. Whenever you take risks in life, you’re essentially opening an invisible door that shapes you and delivers you closer to where you want to be. Read more>>

Lauren Frazier

Betting on yourself is hard. It’s definitely not something we teach in our culture. In fact the opposite is taught. We are trained to pick an already established path. Read more>>

Kendra Neal

The first two years of my business, I had been working out of a really small space, training a couple of apprentices, and I knew that I wouldn’t be able to grow anymore unless I had a bigger space. Read more>>

Volodymyr Prysiazhnyi

On August 27, 2023, at the Sport of Kings in Hallandale Beach, FL, an Emigrant took a leap of faith. Armed with only $100, he dared to organize a concert for 1,500 people. Read more>>

Gabrielle Garofalo

Risk is built into my DNA. I’ve always been open to experiencing and learning new things which helps build risk taking mentality and behavior. Read more>>

Kelly Hurd

I grew up in a household where there was a lot of instability – financially and emotionally. I remember times when we could not afford groceries and my parents going through bankruptcy. Read more>>

Raehanna Evans

It all started at 7 years old when my grandma taught me how to make my first dish, deviled eggs. I had always been in the kitchen sitting at the barstools watching timeless classics while my grandmother would cook. Read more>>

Insa Verbeck

Awwwww, what an intriguing question to begin with. The word “RISK” already is glittering in my mind, tempting, and magnetic. In fact, few things thrill me more than what my friend Connie calls the “unknown Unknown”. Read more>>

Alexi Gonzalez

In 2020, after six years of dedicated work in the TV and Film industry, I found myself at a crossroads. For the past three years, I had been deeply involved with the hit Netflix series “On My Block” as an Associate Producer/Story Consultant/Assistant to the Showrunner. Read more>>

Britni Treadway

What is the meaning of life if you’re not taking a little gamble with your aspirations? My entire art journey has been a risk. Deciding to finally change my major from Math/Accounting to Studio Art was risking the success of my future with an illogical route. Read more>>

Indre Buechler

Taking a leap of faith after putting the corporate world on pause to focus on raising my young daughters was undoubtedly a risk, but little did I know it would lead me to an unforeseen passion. Read more>>

Jamie Lee

In 2003, I was preparing to take a leap of faith. I was divorced, my mother had just passed away, I was unemployed, and I was living in a community with minimal opportunity for advancement Read more>>

Morris R. Austin

They say the entertainment business is one of the hardest businesses to break into! That’s all I heard as a starving actor coming out of Richmond, Virginia. Read more>>

Johanna Hribal

I started my photography business in 2018 as a way to make extra money as a teacher, but within 3 years I actually beat my teaching salary (with 8 years tenure and a Master’s degree) and was shocked that I could be so successful and so happy in such a short amount of time. Read more>>

Katerine Blume

I feel as though my life has been one risk after the next the last couple of years. Even if I didn’t necessarily feel ready, the universe has been doing it’s thing! Read more>>

Nikita Hill & Ameriah Miller

For Nikita and Ameriah, the dynamic duo behind 30seven Trinkets, a mother-daughter business specializing in unique accessories, embracing risk has been a cornerstone of their journey. Read more>>

Lara Wolf

I believe playing things safe is a form of self-protection, which sometimes – of course – is necessary. However, I don’t think I’ve ever achieved anything by playing it safe, especially not as an actress in this industry. Read more>>

Latisha Pickens

My full time job was at Aramark where I was working as a supervisor, a job I had held for six years while trying to make ends meet. Starting out, I faced challenges such as not having transportation, which made it difficult to get to work. Read more>>

Valentina Merico

I spent 10 years working for a big American corporate and building a great career, but just when I reached the peak of my professional journey and was about to move to the USA, I quit my job, sold everything I had and decided to travel around the world for a year or two. Read more>>

JEANNINE CURTIS

I’d like to talk about a current/ongoing risk. It’s the risk of showing my work. In the last year I made a rigorous assessment of what areas were my liabilities for getting my work out to the public. Read more>>

Henry Tran

Sometimes you face a fork on a road which is often inhibited by fear of failure and being judge. I took a risk to move across the country to be with the one I love, I am now happily married with two beautiful girls. Read more>>

Brenda Gonzalez

I took risks giving up my stable, day job in the financial services industry into owning my own business in Fashion. It was a leap of faith, but I believed in my self, knew I had what it took, and when all else failed, life pushed me into this direction. Read more>>