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.

Donna Spruijt-Metz

Writing a poem that is true and that truly moves people always involves risk. Certainly in these fraught times where language has been hijacked, vilified, deemed politically correct or incorrect, labeled as ‘belonging’ to one group or another, the cancel culture, etc.–how do we stay safe without being silenced? Read more>>

Kerriann Otaño

The amazing thing about being an artist is that it gets in your bones. When you are a singer, your instrument is your body and the art that you make can feel like an extension of yourself. Read more>>

Dominique Lindsey

My path to the biggest life change for me started on February 20,2022 when I was sitting in my living room floor after my aunt asked me to complete some signage for her upcoming vow renewal ceremony. Read more>>

Jennifer Tawil

At 52 years old, I took the risk of embarking upon a totally new career and started my own business. In December 2021, my boss at the time, NYS Assemblywoman Sandy Galef announced that she would not run for re-election in 2022. Read more>>

Cody Y

Once upon a time, fresh out of college, I embarked on a quest to pursue a career in professional athletics. From the crack of dawn until late into the night, I delved into our practices and workouts, hoping to make my mark in the competitive world of sports. Read more>>

Jakayla Fenderson

In my journey to establish my spa I faced pivotal moment where I had to decide whether to to pursue my passion or stick with the security of a bed side nursing job. Read more>>

Monica Becerra

Hello readers! Thank you for taking the time to learn my story. I hope this resonates or helps you in some way. Three years ago I felt that I was taking a risk when I decided to start my own small business. Read more>>

Brittany Williams

Embarking on a journey of self-belief was the boldest move I ever made, especially considering the timing. Nearly two decades ago, my focus centered on natural body care when I decided to take a significant risk. Read more>>

Kristy Angelee

“Life is filled with taking risks. The key is finding the risk that is worth taking.” This idea kind of goes with the saying, “Choose your hard.” Read more>>

Talia Tucker L’Whor

The biggest risk I’ve ever taken as a Drag Queen is the decision to quit teaching and pursue entertainment as a full time artist. Read more>>

Mariana Atencio

As a creative, one of the biggest risks I’ve taken was leaving my corporate job as a national correspondent at NBC News. Many of my colleagues and family members thought I was crazy for leaving what most considered ‘a dream job’. Read more>>

Ariza Photography

One of the biggest risks that ARIZA has taken is choosing to transform our passion that initially started as a hobby into a dynamic photography business in the Metro Atlanta area. Read more>>

Troy Scott

In my life I’ve taken many risks both as an author and in reality. In reality, taking risks as an author and in life requires courage, perseverance, and the willingness to face rejection. Read more>>

Sarah Almond

My third and final child was nearly a year old and I had decided I needed to go back to work in 2020. My career is in healthcare (nursing) and I had taken time off to be at home after having my baby. Read more>>

Rebeccah Silence

I’ve taken many risks in my life and throughout my career. My qualifiers before taking a risk are: 1. I educate myself to ensure that, if I choose to move forward, my decision is empowered and informed. Read more>>

Dianne Weed

I was a 57 woman who’s only job for the past 38 years had been to be a stay-at-home mom. My youngest daughter was just months away from high school when I came up with the idea of starting a non-profit that would inspire and encourage the foster care community by meeting their needs in a practical way. Read more>>

Grace Niemitalo

Honestly, most of how I got to be a business owner and therapist was from continuous risk-taking. The first risky decision to step away from traditional education while I was in high school could have really changed the outcome of my life. Read more>>

Karola Raimond

First of all being an artist already withholds a big risk, you decide to live a life that is very unpredictable and definitely not a linear life path. Read more>>

Poojitha / Rasika Palaniswamy / Selva

Taking the leap to push for the creation of Archers was something that was definitely a challenge. We were so passionate about this project, about creating this community for the art of public speaking, but it involved a lot of faith in ourselves to bring about. Read more>>

Misha Hooper

One of the riskiest things that I ever did was bet on myself. Some would say that’s not a risky thing to do; in fact when it comes to self they would bet on themselves every time. Read more>>

Kim Raaf

This is the story of my risk and why people hated me for taking it at first. Growing up, nobody in my family – probably no adult that I knew personally – had a creative profession. Read more>>

Giovanni Salazar

Starting Efficient Soccer Club was a leap into the unknown, a journey from comfort and predictability into a realm where passion and belief were my main guides. Read more>>

Ingrid Kapteyn

The daily risk of recommitting to the creative path is the one that mystifies me, even as I take it, day after day. Freelancing seems to ask for the faith of a saint, the endurance of a triathlete, and the courage of a skydiver. Read more>>

Vanessa Porras

Attempting any sort of creative endeavor is inherently risky. The development of the idea is not the only thing that comes with risks, the execution and final product has its own hurdles. Read more>>

Maddie DePaoli

I’m currently enduring the biggest risk I’ve taken in my life. Maybe the biggest risk I will take in my entire life. But I’ve taken smaller risks that have led up to this, so I like to tell myself that I’ll be okay. Read more>>

Natasha Monique Shivers

In 2018, the national pageant was supposed to happen that October in Panama City Beach, FL. I spent months working on marketing and preparing the area for it’s first national pageant. Read more>>

Serena Dailey

One of the biggest risks I’ve taken is diving into the world of entrepreneurship and starting my own business! I had been working for a company in the immersive pop up event industry for 3 years and I decided it was time to do things my own way. Read more>>

Jes Leneè McCombs

After a break up, my car dying, my bicycle stolen, being kicked out of my moldy rent house to be torn down, becoming ill, and loosing my job all in one summer, I decided at 23, I needed to leave… Read more>>

Jill Hilbrenner

Opening Witch Hazel represented a giant pivot for me. I had worked in media and writing jobs for more than a decade, until getting laid off in early 2022. (The same week as my birthday…that was a weird birthday!) Read more>>

YOUTHYEAR

One thing I’ve learned about taking risks is sometimes the risks don’t feel like risks…and sometimes they do haha. For example not going to college didn’t feel like a risk cuz I was 100% sure I was gonna do music. Read more>>

Andrea Isaacs

My first night in college, I was tormented with questions I couldn’t answer — questions like, “Who am I?, What’s the meaning of life?,” and “Why am I here?” Read more>>

Elaine Riley

I took a huge risk in my business about a year ago when I decided to transition from the soap and skincare space into a more spiritually forward, service based business. Read more>>

Eric Freeman Sims

I feel I took a huge risk going from a stable career in the medical field to being a full-time content creator. Especially not knowing if anyone would be interested in what I had to say as a podcaster and if the investment would pay off. Read more>>

Krista Mason

In entrepreneurship, embracing change and taking a risk can be a daunting task. I used to be someone who was afraid of change, honestly I still am. Read more>>