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.

Breanna Decker-Grant

Every choice presents a gamble. Each step down one path is a further deviation from another option. And for so long, I tried to walk the line between entrepreneurship and having a stable, full-time job. Read more>>

Maryella Porras

My journey into the world of mortgage lending began with a whisper of possibility and a seed of ambition. Read more>>

Kash Thompson

As a child it was instilled that success was measured by the level of profession you acquired. To be a doctor, lawyer, etc was the ceiling. Being a creative was not something that was honored nor pushed. Read more>>

Claire Dunn

Before arriving to the US, in the past years I did a series of adventures by myself, with only a backpack and a tent, following signs and intuition. Read more>>

Jason Bass

I built a newly formed relationship with the incoming general manager of a boutique hotel in midtown Baltimore, MD. Read more>>

Webb Travis

Taking risks in life has been a defining journey for me, Webb Travis. I made the bold decision to step away from the familiarity of corporate America, where I had spent over eight successful years at Equinox as one of the top producers. Read more>>

Lisa Knight

Becoming the leader of this organization has been one of my greatest joys and accomplishments. There was a long time in my life growing up that I didn’t know who I was or where I was going. Read more>>

Taniqua Miller

In the Spring of 2022, I found myself behind the wheel of my mini-van sobbing. I was incredibly anxious and professionally burnt out. Read more>>

Amira Smith

After beating terminal Cancer I became a competitive strength athlete. I also started coaching and wanted to open up my own facility. Read more>>

Erin Thomas

I have taken two major risks in my life, both of which proved to be two of the best decisions I’ve ever made and both laid the foundation for the incredible life I’m living- and multi-six figure international business I’m running- now. Read more>>

Janis Treiber

In the retail world, risk-taking needs to be calculated, and based on not only past performance, but spur new growth and innovation for both merchandise and the ability to reach new audiences. Read more>>

Tessa Lee-Thomas

I have always provided child care as a side business since 2011. However in 2022, after being laid off from my sales position, I decided to take a risk and bet on myself! Read more>>

Christine Anastasia

The last several years through the pandemic have been transformative. I was furloughed, laid off, unemployed, started a business, was working as a stay-at-home mom and entrepreneur, and went from a secure paycheck to the uncertain financial stakes of being a new business owner. Read more>>

ERICA PARR

I have always loved accessories and color from a really young age. You could usually find me draped in what my parents lovingly referred to as ‘junk city’ – a collection of colorful plastic chain necklaces and bracelets with charms that I could clip on and off. Read more>>

Honest Skin

We absolutely love sharing our story because it’s not just a part of our origin story; it’s what keeps us motivated to keep moving forward. In 2020, we realized that we shared a similar vision and skincare philosophy. Read more>>

Yazline DeJesus

Growing up in a single family low-income home. I learned through all the many struggles in life to always take a risk on myself. Read more>>

Sannchaz Blackmon

I’m a firm believer in taking good risk. Especially if I know that there is a possibility that it would be for my greater good. Read more>>

Steven Lufkin

In early 2019 I had the idea to bring a handful of of indie-artists together for a music tour up the West Coast of the US. I had never planned a tour like this before but, I have a way of letting my passions drive me into things that I don’t always have the expertise for. Read more>>

Rae Solomon

The belief that life can be entirely risk-free is ultimately illusory. Society often encourages us to pursue the path of least resistance, opting for conventional careers deemed ‘safe.’ Read more>>

JacquieO Silvia

Biggest risk I ever took was betting on myself. As a young child, I took a lot of risks. Mainly, because I lacked any fear at all as a kid. Read more>>

Jenny Chasteen

I never meant to start a business. I just wanted to tell stories about adventure and magic and treehouses. Read more>>

Sara Bruno

My transition from burlesque dancer into the world of go-go dancing started by me taking a risk. I was back stage at my first electronic festival, Astral Harvest. Read more>>

Elizabeth Lambert

Recently, I took the leap and moved to California after living in Arizona for my whole life ( Shout out to New Jersey for keeping me real until I was 2 years old lol). Read more>>

Kena Ramírez Dillon

Looking back, it seems my life has been comprised of many risks. All leading me to where I am at the moment. One of the biggest risks was deciding to bet on myself. Growing up, I was the art kid. Read more>>

Sarah Krippner

Well, being an entrepreneur is its own risk in so many ways. Going out on your own, reaching out and finding your clientele, opening your own space and knowing each month it is totally up to you to make things grow and flow. Read more>>

NATALIA PERSHINA

Living in Belarus, I dreamed of traveling the world, exploring countries, cultures and languages, showing my creativity and unlocking my potential, recognizing myself in the world and discovering the world within myself. Read more>>

CRYSTAL M EADS

I think that anyone who makes the jump to pursue their dreams and step out on faith, is taking a risk. A risk that the business may fail. Read more>>

Jill Garcia

Kim and I met during the height of Covid and it was already scary enough to talk to some one new in person. Read more>>

Elaine Tsung

Three years ago, amidst the chaos of the pandemic, I found myself at a crossroads in my career. Read more>>

Tamara Thomas

When I first started my journey I was 19, I was a soon to be nursing student in my third year of college at Texas A&M in Corpus Christi and dedicated. Read more>>

Trevor Carlson

Back in 2017 I had taken some time off after working at a health tech startup and gotten a job at a local marketing company. Read more>>

Veronica Sanders

One of the most significant leaps I’ve ever made was diving into the world of interior design entrepreneurship. Back in 2019, I found myself in a design firm that didn’t align with my aspirations. Read more>>

Mark Gallo

“More often than we care to admit it, we don’t get what we want because we quit early or we didn’t take the necessary risk to get it” -Matthew McConaughey Read more>>

Tanya Kaiser

I moved to Cleveland in November 2023 without any family or professional connections. I was excited to be in a new city, looking forward to exploring the place I would call home. Read more>>

Jonny Ezra Thompson

At the age of 18 I moved out of my parents’ house and out of my home state. I knew that I wanted to pursue music, but even more significant to the conclusion of my decision, I knew that expanding my worldview was paramount. Read more>>

Maya Bernstein

I wouldn’t call myself a “musician” – but a few years ago I noticed that I often heard melodies in my head. It’s likely I’ve heard melodies for years, but I never slowed down and got quiet enough to pay attention to them. Read more>>

Angela Moore

In 2021 I was employed by a Day Service Facility that specialized in care for Veterans with Dementia. I was able to learn the history of some of their lives , and see the spark in their eyes that Dementia was slowly robbing them of. Read more>>

Nadine G

Embarking on the journey of starting my own business was not just a leap of faith; it was a monumental risk that reshaped my entire life. As a counselor and a self-published author, my career had reached a point of stability and comfort. Read more>>

Jennifer Fleming

Risk is inherently connected to almost all entrepreneur stories; as risk drives actions, decisions, and hopefully successes. Read more>>

Lacey Boucher

My journey led me to being an elementary school teacher. In 2022, I decided to take a step down from full time teaching to pursue my dream of being a children’s book author. Read more>>