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.

Shayna Norwood

I had been in my little 100 sq ft studio space in Pilsen for 3 years and was desperately running out of space. We were getting monthly wholesale orders from Paper Source (the national chain) for 2000 – 5000 units. I was regularly adding products to my line, and was finding it difficult to fit printing presses, post-production, and warehouse along with employees and interns all in that one small space. We were regularly shifting piles of product around the space to make room to work in different areas. Read more>>

Dawn Ash

Opening my own houseplant store was a huge risk for me and my family, I have worked for someone else since I was 16! It was something I had always dreamed of but never thought could be possible. It came about naturally though and I feel that when things align a certain way it is meant to be so we went with it! A little backstory, I started collecting plants as a hobby for myself, I wanted to grow my collection but my husband was out of work with an injury so I starting propagating my plants to earn money to purchase more plants. Read more>>

Genevieve Harris

One of the biggest risk I have taken, along with my husband, is opening the yoga studio and a second location before the pandemic. Several years prior to opening our first studio in 2017, our youngest son was diagnosed with Dravet Syndrome and suffered a traumatic brain injury resulting in 100 percent dependent care from family and aides. Read more>>

Mallory Ulaszek

I’ve been a risk taker all my life. Whether it’s starting a business (or multiple), beginning a nomadic international life, or uprooting myself in general to get in alignment with how I dream to live daily, it’s in my blood and I never question making a leap. About 1 year ago, I decided to break with conventionality after a divorce. Read more>>

Marticia G

taking wrists is in my opinion the most valuable thing you could ever do in your entrepreneurship career. Life is all about taking wrists, riding a bike hiking up a mountain starting a brand new job you know nothing about. Entrepreneur ship is all of those fears being thrown to the side and amplified times five. Read more>>

Ruben Ayala

I nearly lost my business in May of 2020 due to the mandated government shutdowns following the COVID-19 pandemic. During the month of March 2020, I was forced to let go of my entire staff and lost nearly 90% of our revenues within 2 weeks. I had the misfortune of being in the food and service industry and suffered tremendously. Read more>>

Coach T Speaks

I have been Coaching for 25-plus years but never thought of it as a business. I am a Social Worker and have been working for other agencies. I loved what I was doing and was successfully helping my clients reach milestones they never thought they could reach. But I was always going the extra mile, sharing my story and being transparent with my clients. Read more>>

Brandy Baye Robidoux

I’ve always believe in taking risks, but, most times, play it safe with my career. In 2022 I took a massive leap of faith and traded my journalism career for life at a record label. I wanted to be closer to the art, working directly with artists every day and seeing the smallest seeds and ideas come to fruition. It’s safe to say it was worth the risk and has been rewarding in more ways than I ever imagined. Read more>>

Andrea Brody

For many years I balanced two careers: Graphic Designer and Pilates instructor. I worked 80% of the time as a graphic designer, but longed for it to be the other way around or better yet full time Pilates instructor. One day I thought why not try? I actively pursued my Pilates career. I knew I had to make changes to make space for Pilates, so I turned down design projects from big clients. Read more>>

Steven San Lucas

After we learned about CVID and all restrictions in the process i started to search for other alternatives for work since i am a waiter and several location were closing so i hear about affiliated link programs and started to get all the details to make it work for myself. And just like that became to promote different corporations in the travel industry so i said to myself i just want to do all about tourism and here i am today. Read more>>

Angel Morgan

Hello, my name is Angel Morgan. CEO of Anjewls Cosmetics. My entire business has been based off of risks I have took to elevate my career. Since, making my first investment or finding a vendor who will distribute good product. Having a successful business takes making decisions that will hinder ,affect and grow my line of work.Nevertheless, just not any risk. You have to be able to think about the longevity of that type of exposure. Ask yourself questions like, “How will this impact my business?” Read more>>

Art Vasquez

Like a lot of artists before me I drawing from an early age. would mostly draw cars and moved to drawing on my arms lol Had my first tattoo by the age of 12 Of which I did on myself from a crudely made machine out of a Walkman motor, guitar string and 9 volt battery By 15 I had an entire backpiece and went to my first tattoo convention Invited by my friend David Gama who did my back tattoo. Who still tattoos to this day btw
He would show me some things about his machines and processes. Read more>>

Nkunim Owusu

After I finished college I had two choices go to grad school or pursue content creation. I started making content in 2020 and I was doing really well and impacting a lot of people but never took it seriously because I thought it wasn’t sustainable. So when Covid died down I went back to school to get my degree in criminal justice. Read more>>

Sharon Glassman

When I decided to launch a line of greeting cards, stickers and gifts that sang my original songs from QR codes on the art, I was told that folks in the US would never warm up to using QR codes. Read more>>

Brooke Gary

This year makes 10 years that I’ve been living in the great state of Texas and also 10 years of working in the Plastic surgery field as a nurse. I’m originally from Louisiana, born and raised between New Iberia and Franklin. I graduated from nursing school as an LVN in Louisiana as well in December 2012. At the time my kids were very young at the ages of 1 and 3 years old. I passed my Boards exam in January and immediately started looking for a job in Houston and surrounding areas in hopes of giving my kids and myself a better chance in life. Read more>>

Joshua Caldwell

Whiteness as a construct has always provided a space for me to take risks. With that in mind, I must always hold space for those not afforded the same protections. The risk is not the same the closer to Blackness you approach. Read more>>

Paula Navarro

Taking the risk of following your heart step by step is one of the most challenging ones and also the one that will retribute the most I believe. The act of start creating my videos and sharing my knowledge was a risk taking step for me for sure!, Read more>>

Rashidat Odeyemi

The biggest risk I’ve taken was leaving a great career to pursue a yearning that I had no idea where it would take me… Like most professionals, I went to college, got a degree, and I was fortunate to get a job in my field just 3 months after graduation. But it started in my first career position, and then continued into my second, and I even thought I’d quit it all a become a dog walked during the 2008 recession, but my career pulled me back in then, too. Read more>>

Sara Lennert

Deciding to start my own business has been the biggest professional risk I have taken to date. In college I was inspired by the independent contractors creating and managing wildlife habitat. I wanted to be just like them when I graduated, but I didn’t know how. After graduating, I spent time working in the wildlife field. Over the years I worked as a naturalist, a field technician, and even taught an ornithology (bird ID) class! Read more>>

Kat Beck

I worked in a cubicle for 9 years as an administrative assistant. I loathed driving to my job every day. But I felt completely stuck; I just couldn’t figure out WHAT I wanted to do. When I began reconnecting to my body through energy work and somatic practices, my life slowly then suddenly began to shift. Read more>>

Sarah Hill

“My resignation is effective immediately – to protect my physiological safety.” As you can imagine that sentence was the hardest thing I ever hit “send” on in my life. I was a successful Creative Director for an international beauty company, but my working conditions where toxic and I was being gaslit without room to respond. Read more>>

Lisa Hammer

I always take risks. I always have. It’s hard to know where to start. From my decision to be an entertainer when I was a child – every audition, rehearsal, performance all were risks, as I was very shy. I just knew I had to perform. I seem to have been punished in life whenever I DIDN’T take a risk. When I got to college, I blindly jumped from musical theatre right into filmmaking. Read more>>

Chavali McIntosh

Encouragement is my love language and always will be. Having a mentally disabled older sister led to me working with high-functioning, mentally challenged adults and troubled youth once I graduated high school. During my 20 years of active duty service, I volunteered for the “mushy” collateral duties like Equal Opportunity Representative, Uniformed Victims Advocate, and Substance Abuse Counselor Officer. As a hairstylist, I volunteered and provided Haircuts for Hospice and was a regularly lent and “ear” to my clients. Read more>>

Amy Prenner

In 2007 I was laid off from a job I loved that gave me a sense of purpose and I didn’t know how I was going to proceed. With the help of some amazing friends and mentors I took a leap of faith and realized that had a lot more knowledge and understanding of how to run a business than I gave myself credit for. Using my relationships I signed my first client NBC Universal, and landed a high profile client launching a reality singing competition called THE SINGING BEE, hosted by NSync’s Joey Fatone. Read more>>

Hannah Day

I think part of being a business owner is taking risks. Every big step in my business has seemed like a big risk. When I opened my online shop 3.5 years ago, I spent about $150 on inventory. Then, that seemed like a big deal. Now, I’m glad I started small. I have never taken a business loan. I’ve worked my way up from the bottom. It took a while to get my first sale and it’s not been until now do I actually get sales every day. Read more>>

Rose Dernburg

Back in 2021 I had decided to sell my condo in Fort Collins, CO. At that time I was a working actress/model who had a bigger picture in her career. Where it all began: Back in 2019 I had started my acting/modeling career. I also had two jobs on top of that to keep me at float financially. As I was progressing in my career I kept thinking of moving out of Colorado, I just didn’t know where. Read more>>

Jenise Collins

I was at my job for 15yrs, regular pay check, work regular hours, plus working with kids to help change lives. I started my business with no team, use.my own money, plus I did not have all the tools to be in business.. But I have passion Read more>>

Sana Yusuf

Tell us the story of a risk you’ve taken – it could be a big, life changing risk or a small risk. Either way, paint the picture for us, tell us the backstory and all the relevant details so we can fully understand the context and circumstances around when and why you took the risk and tell us how it turned out. Read more>>

Cheri Barbo

I’ve been an artist for as long as I could hold a pencil in my hand, but I never completely jumped into it as anything more than a hobby until 2 and a half years ago. I come from a long line of artists, rather they were writers, painters, or musicians. My family was also very poor, because 30+ years ago art wasn’t what it is today, growth wasn’t something that was common as an artist, but it made a nice side hobby! The lucky ones were able to make it into something far more. Read more>>

Keenan Schuur

Real estate had always been something I was interested it but it was kind of a scary thought to dive into, since it is 100% commission based and I was married with kids, so I started small. I got my license in May 2015 and worked as an agent part time, while I worked as a sales rep for a wine & spirits distributor. The first couple of years were pretty slow, I didn’t put a lot of focus on building my business. Read more>>

Just Acting Up

When we started our show most didnt understand it at 1st. We had to work hard to grow this platform. Most podcast at the time were pretty one dimensional. So introducing something new and different can be risky. Will we be able to even get people to check out the show??? That was a big question, but having the right team was key. Our chemistry on the show translates just as well behind the scenes, Read more>>

Richard Robinson Jr

The Biggest Risk I’ve taken was back in August of 2020 I went to Orlando Florida for a content creator event and to stay at the Mansion resort with famous creators. At the time I had low followers on both Instagram and Tiktok, but I still went to network an show my face. I networked with a lot of top content creators even today like Robiii World, MatteBlackBoy, and Zale. Read more>>

Natasha Federico

When people hear the word “Risk”, they tend to turn away from it because the word “Risk” is typically associated with the words such as “fear”, “Loss”, “backward”, “start over”, “devastating”, etc., but I when I hear the word Risk I think of excitement, a gamble with the unknown, a chance to win and to succeed. Read more>>

Ranetta Perkins

As a veterinary student, I promised myself at graduation that I would own a veterinary practice one day. I had no idea how and with what money! I had no mentor or example of the type of leader that I wanted to be. I didn’t know someone that could talk me through the process or advise me on how to best be successful. No road map. No business acumen. No financial investors. All I had was my learned clinical skills and a desire to be excellent. Read more>>

Ol’ June

“With talent comes responsibility.” What do I mean by that? Let me fill you in. I was always musically talented. I come from a family of singers, some saying my grandfather was a monster vocalist. I never got the pleasure to hear this though as he passed when I was a child. As a kid my father would say, “This boy can sing” when I would be humming to myself. Writing song on the back of the bus to avoid the bullies and being in my own world. Read more>>