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.

SJ Russell

Operating a community resource and mutual aid organization is never without risk, and I’ve learned to embrace the uncertainty along the way. As a Sagittarius and a very regretfully type-A person, it took me longer than I’d like to admit to lean into the “mutual” part of mutual aid. Read more >>>

Sarah Penna

The biggest risk I’ve taken was walking away from my executive career in tech to start Flock White Doves with my parents. I remember sitting in back-to-back meetings one day, my phone buzzing with texts from the babysitter, and realizing I was missing everything. My kids were growing up, and I was watching it happen through chaotic weeknights and weekend catch-ups. Read more >>>

Leanne Elliott

After 25 years as a successful entrepreneur and event planner, I found myself running on empty. What once inspired me had become a source of exhaustion. Despite the outward success, I was experiencing deep fatigue, burnout, and a cascade of physical symptoms that only grew worse the harder I pushed. Read more >>>

Christina Williams

Taking a risk was the first step in my entrepreneurial journey. Coming from a mother who dabbled in sales back in the ’90s, I didn’t have a blueprint or role model for what running a successful business looked like. My first inspiration came when I received the idea for a script while in the shower and at that moment Ahava Hherouth Productions LLC was born. Read more >>>

Leah Danley

After 26 years as a licensed therapist working in a traditional counseling setting, I took what felt like one of the biggest risks of my life—starting Quiet Mind Collective as an online presence. I wasn’t raised with social media, so stepping into a public space felt foreign and overwhelming. Read more >>>

Marcus Artico

When I decided to be an actor in Brazil my dad and cousin laugh at me and told me to forget and that was not for me . Read more >>>

Tia Javier

The biggest risk I ever took was starting my own therapy practice — right in the middle of the COVID-19 pandemic. The backstory is that I had earned a second master’s degree in communication sciences and disorders after my daughter inspired me to go into the field. Read more >>>

Rebecca Reynolds

Back when I started Destination Weddings, it was a learning curve for me. I found that the majority of destination weddings booked had a risk of travel. I learned how to travel from Destination Wedding couples. Read more >>>

Carlos Bown

My life has been about taking risks since day 1. I am originally from Caracas, Venezuela. I played Golf for the National team since the age of 15, my goal and dreams were always to play professional Golf. At the age of 17 I decided to move to the US. by myself, without my parents, to chase my dreams. Read more >>>

Joan DiGiovanna

You know, when I think about taking a big risk, it was the decision to go into real estate at 57. At that point, I was over $100,000 in debt, and I couldn’t afford real estate school. A dear friend believed in me enough to pay my tuition—and that changed everything. I had already been working over 80 hours a week just to stay afloat. Read more >>>

Ericka Evren

The biggest risk I took was summoning the courage to not only write the story I’ve wanted to tell since I was thirteen, but actually publishing it. I spent several years writing and rewriting draft after draft, applying different knowledge as I went, trying to perfect my craft. I tried plotting and failed. Read more >>>

Emma June Jones

The greatest risk I ever took was the day I moved to New York City. I had just graduated from the Savannah College of Art and Design, holding an illustration degree, a suitcase, and only a few bills tucked into my pocket. I landed in the East Village with the stubborn belief that within a month I’d find work and make it all come together. Read more >>>

Kelly Mockbee

In 2019, I decided to start my own travel business as a way to supplement my love of travel. At first, it was just a side gig. I started with zero clients and figured it might be something I’d grow into after retirement. I honestly never imagined it would become more than that. Then came Covid. Read more >>>

Lala Torres

The risk I took was starting my business. The idea was pitched to me, and I thought it was crazy and wild that someone wanted to entrust me to take over such a legacy. I have never owned a business before but I had a lot of experience in the service industry . Read more >>>

Heather Arroyo

Travel has always been my first love — it’s where I’ve felt most alive, most grounded, and most myself. Long before I became a mom, I dreamed of seeing the world, and once I had my daughter, I dreamed of showing it to her. Read more >>>

Robbye Kirkpatrick

A partner and I recently launched Texas TransformED, which is a non-profit that seeks to make Texas #1 for K-12 public education. Texas is currently ranked #44. This transformation will require leadership, cultural changes, and data transparency throughout the state system. Read more >>>

Ashlyn Tarp

When I started Simply Twisted Co., the biggest risk wasn’t just financial—it was putting myself out there in an industry where I knew I’d be compared, questioned, and challenged. At the time, there were safer paths I could have taken. Read more >>>

Laura Romero

My landlady, Velia Chavez, inherited the property and wanted me to do something with it. The only thing I could come up with was a Christmas shop, since when I had young kids I decorated to the point that my friends would tell me I should charge to come in & see my house. Read more >>>

Cody Rager

When we started Rager Fencing, my wife and I had a 1 year old and my wife was in college. I had quit my full time job at a factory because I wasn’t seeing my child very much working nights and she was trying so hard maintaining everything. I had always been around fencing so I thought to take the risk. Read more >>>

Bobby Brown

Grew up in the Financial Services industry, first in banking, then in the Cotton Futures trading, then with name-brand Investment firms. Built an investment book of business that was based on sound advice, relationships, service, and hard work. I had positioned myself well with a reputable Investment Firm, and it looked as if I would be there for the rest of my career. Read more >>>

Amanda Sinnott

One of the biggest risks I’ve ever taken was leaving the 9-5 world to start my own tutoring business! After a season of loss and the chaos of Covid, I had to take a step back and really ask myself what I wanted to do with my life. Read more >>>

Marina Badillo

In the summer of 2023, I began planning to launch The AI Social Worker on January 1, 2024. At the time, ChatGPT was still new, and almost no one in the social work field was talking about it. In fact, many professionals were outright against using it, voicing strong opposition and skepticism. I knew stepping forward could be risky. Read more >>>

Tarneshia Barnett

I worked for UnitedHealthcare for eight years, moving up from community health worker to team lead, community engagement coordinator, associate marketing specialist, volunteer coordinator, and even a volunteer board member. It was a solid career with benefits, 401k, paid time off, and stability. I was working on my bachelor’s degree in healthcare administration leadership to eventually step into management. Read more >>>

Shaqueria Dial

One of the biggest risks I’ve taken was starting my creative business while still working full-time. I didn’t have help or a roadmap—I had to figure everything out on my own, from building my brand to learning how to market myself. Read more >>>

Kimberly Hohensee-Gualnam

I was recovering from Breast Cancer Treatment, and I heard Yahweh say that I need to open my own mental health agency. This was a shock because I went to school to help people maintain and regain their mental health, not to be a businessperson. Read more >>>

Amy & Nell

When we met, we quickly realised we shared the same dream. We’d both always wanted to start a business, something mobile and community focused, but had never quite found the courage to do it. Read more >>>

Joshua Booth

Opening this business was a huge risk. I was in Austin Texas working for one of the top BBQ restaurants in the state, but always wanted to have my own restaurant. I have done nothing but working in restaurants my entire life, from dishwasher, to executive chef, to area director, and so on. But I felt like God was calling me to do something else. Read more >>>

Rich Robledo

During the last recession, I lost everything in 2006 2 years before the stock market crash. I questioned my career and myself at the time. I was blessed to have several mentors help me through this time with many great lessons and insight. They each were able to point out that, being in business for ourselves is always a risk. Read more >>>

Johntay Jones

I recently took a pretty big risk On the last movie I made. After I Paid for my first film out of pocket I swore I would do everything in my power to not use my own money To finance Another movie. Read more >>>

Christina Ewing

If you had told me 3 years ago I would own a cafe in the sweet little town of Berlin I would have thought you were crazy! But as a side gig I started making french macarons, people liked them, they wanted to buy them, and I was thrilled at the thought that I might be able to do something creative…maybe as a profession. Read more >>>

Donna Walton

Daring to Be Visible I didn’t set out to be a rebel. I set out to be seen. Years ago, I stood at a crossroads—one leg amputated, the other trembling with uncertainty. I had spent decades building a life of purpose, but the world still didn’t see women like me: Black, disabled, vibrant, whole. Read more >>>

Stephanie Sica

For starters, I genuinely believe that we open ourselves up to risk every single day, in various situations. Whether it’s in a personal or professional setting, choosing authenticity — to show up fully and unapologetically as yourself — is always a risk. That is: the risk of someone rejecting who you truly are. Read more >>>

Madeline Stewart

The biggest risk I took regarding the business was the desire to ‘push the envelope’ so they say with our product and displays. I wanted to incorporate bold colors and patterns, large floral designs, and botanical stems with big furniture and textiles. My goal was and is currently, to bring joy and fun to the mundane. Read more >>>

Demetria Sheckles

I remember scrolling through YouTube one day, watching people talk about how they were making good money as notaries. I thought, “Wait a minute people are getting paid to stamp papers? Where do I sign up?” So I took the plunge and enrolled in Mark Wills’ Loan Signing System. Read more >>>

Sabrina Guler

If I had to point to one theme that has shaped my journey, it would be risk. Taking risks has been the pillar of my entire career in entrepreneurship. The biggest risk I have ever taken was walking away from stability to start over, and it has happened at multiple points in the past decade. Read more >>>

Kelli Bell

I opened an ice cream shop. I saw that there was a need for a place where families and friends could gather just to enjoy each others company in a fun, upbeat environment. There were no dessert or ice cream shops in our community, so I took a huge risk and invested all of my own savings, and took out personal loans, to open Chillville. Read more >>>

Liberty Stavinoha

I quit my 7 year corporate accounting job and jumped full time into stained glass and running a small business. I used my last paycheck from my accounting job to buy the supplies and began selling within a few weeks of making my first piece. Read more >>>

Abby Austin

Opening my store was no doubt the biggest risk I’ve ever taken. The opportunity came out of nowhere — the business consultant from the retail store that was previously in my space called me one day in March of 2022 and told me I had about two weeks to decide if I wanted to take the leap. Read more >>>

Dylan Keene

My journey has been a consistent trend of risks that have gradually gotten bigger as gradual success has been achieved. Read more >>>

Kris Corbett

Fit 4 Adventure is celebrating its 25th anniversary this year! I am celebrating my 5th year as one of the owners of the company. If you do the math, then yes, that means I bought a travel company in the middle of a pandemic. Read more >>>

Monica Fullerton

When I first had the idea for Spouse-ly, I had no clue what building a multi-vendor marketplace actually looked like. On paper, it sounded simple enough: create a place where military spouses, veterans, and first responders could share their products and talents with the world. Read more >>>

Hyeonsu Kim

When I first started working at an architecture firm after Pratt, I was deeply engaged in design details and enjoyed the creative side of the work. But I realized that I never thought beyond “someone else will build this.” That changed when I learned about the role of general contractors. I’ve always loved walking around New York and watching how quickly new buildings rise. Read more >>>

Becca LaPage & Nicole Edmond

Starting Parable itself was a risk, because from day one we chose to build a faith-based creative agency with a missional model. In business terms, it doesn’t really make any sense. We’ve intentionally narrowed our market instead of broadening it, and we know that some people will avoid working with us because of our beliefs. Read more >>>

David Pettibone

I’m a believer in doing what makes you happy and everything else, you figure out along the way. After I received my master’s at the New York Academy of Art in 2007 I had been doing the artist hustle: painting at night and on the weekends, teaching art as an adjunct professor, art handling and, also, mural work for an advertising agency on the side. Read more >>>

Zeinab Diomande

The most life changing risk I have taken thus far is going after my dreams. For context, I was born in the U.S but grew up in my parents home in the Ivory Coast. Coming back here in 2017 has had its set of issues and setbacks but I will never look back on standing firm on pursuing my dreams. Read more >>>