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.

Jennifer Redman

I have been a Realtor in Texas; actively producing, as of 2015. I am a Buyer’s Specialist as well as part of The Cannon Team’s leadership team. As The Cannon Team grew (and continues to grow), our team owner; Christie Cannon, approached me with the idea of a position dedicated to the hiring, training and mentoring of new agents. At the time, she was in conversation with someone outside the team to take the role. After much thought, I emailed Christie with my ideas for criteria and an action plan. Read more>>

Claudia Erickson and Kim Cavallo

Claudia – Kim and I both dove into the field of Digital Wellness as we felt strongly that excessive screen time was becoming a problem that was not getting enough attention. Making that shift has been risky in so many ways. First off, this is a relatively new field and people are still trying to define what it is and how to realistically go about helping people create healthier digital lifestyles. How best to reach people can be a challenge as well. Read more>>

Odette Muzimbe

Creativity is about doing something where you don’t know the outcome, which means it’s about taking a risk. It also means that being creative can have significant gains and there can be significant losses as well. In essence, you cannot be creative while remaining completely safe. I think that’s where some of us tend to get stumped a bit because that is a little bit scary. Read more>>

Travis & BreAuna Burkhalter Motivational Speakers & Mentors

Our Business/Ministry as a whole was a risk for us. The purpose of People of Hope is to encourage singles and those in relationships to grow healthy partnerships. With this goal, we knew we would have to be transparent in our relationship including the bumps along the way. It can be difficult to let others into your personal life but in the end, those we have mentored and those who have heard us speak whether in person, online, or by podcast have given us feedback that it helped them to know they aren’t alone in have test and trials in their relationships. Read more>>

Taylor Strope

Starting your own business feels like taking a step and not knowing when you will touch the ground again. Your foot falls and your stomach sinks, until all of a sudden you feel the step was there all along. I felt that when I took the risk to start Mountainside Events 6 years ago, and again when I decided to take it on full time 2 years later. However, with risk comes reward. I never thought that I would be under 30 and able to build a company like I did in such a short amount of time. I am so grateful for taking the risk so I can be my own boss, and plan so many amazing weddings and events. It truly is incredible to be a part of some of the best days of my clients lives and I will never look back! Read more>>

Just John

Life is about risks, how willing you are to take them and how prepared you are before the outcome. I believe TRUSTING YOUR GUT calls for a certain level of discernment in your own life to see what you will and will not allow, but it keeps you as your most authentic self. End goal is to show you all the sides of me you don’t see, not the sides I think you want me to be. An artists’ responsibility is to raise the consciousness of the people around them, if not what we doing it for? Read more>>

Joel Insilo

Leaving Maryland to move to Miami, Florida in 2018, in which it was the day of my uncle’s funeral was a major risk. The Sole purpose of me moving was because I got drafted to the Rivals Professional Football League which is a professional developmental league. Driving to Miami was extremely emotional and traumatic because I had lost someone who played a vital part in my life. He wasn’t just a regular uncle but he was legit a father to me and the concept of losing a loved one was an extremely difficult and still is til this day. Read more>>

SiMBOLiZM

I took the risk. I dropped out of college only 1 semester in, to pursue music. And I’m SO GLAD I did! I was originally going to college for video technology. Before college I had about 4 years of media experience. College can be great, but at the time, my heart was into music. I felt this energy, like a magnet, pulling me into the EDM scene. I told myself that one day I’d be playing festivals and headlining shows around the country. A few years down the road, I’ve turned that crazy dream into a reality, and it’s been a magical journey. Read more>>

Gayle Fisher

Every day, my son of developmental delays and I take small but life-changing risks: away from safe harbor and yesterday’s habits. It doesn’t sound like a big thing, because it’s more like many little things. If you are a parent with a child who is not keeping up with peers, then maybe you have something on your parental radar that scares you, and you aren’t sure what to do. Read more>>

Maidy Morhous

As an artist most would not think we are risk takers – maybe in the sense that we find it difficult to support ones self through sale of artwork (although I did successfully in my early years, but that is another story for another time). We artists, or those I consider artists, are definitely risk takers, maybe not in the sense of dramatic adventure, life at risk as such, but we definitely to remain fresh and creative must take risks daily – be it our medium, technique, subject matter. I believe that to be a true artist one must not be afraid to experiment, take risk, operate outside their comfort zone. Read more>>

Sydney Yeager

When I decided to return to school and pursue a degree in art, I had 2 young children and no idea what would happen. I gave up an opportunity to pursue an advanced degree with a more “practical” end result. I credit my spouse, who made this remark as we discussed options: “You don’t want to look back on your life,” he said, “and wonder what might have happened.” We were struggling to make ends meet, and there were two children to be cared for. It was a risky decision that we made together. I gave up graduate status, went back as a freshman to study art. I didn’t dare dream that I would go on to get an MFA, have a career as an artist and a teaching job. It was a risk I am so happy I took. Read more>>

Claudia Starr

Biggest risk I’ve taken… well in October 2019 I had just got laid off from my job of 4 years. I had a ton of bills of course that come every month and a severance package of only a few thousand dollars( like less that 3k) and I remember sitting Indian style on my floor in my room and talking to God. Asking do I find another job or do I take everything that I have and fund my business! The biggest and scariest risk that you will ever take is to have faith in your self and your abilities. START THE BUSINESS ! I took everything I had and never looked back. Best decision I ever made in my life and I love what I do. Read more>>

Nicole Lopez

At the age of 17 right after high school I was confidence I wanted to be independent. I moved out of my moms house right after high school being completely scared of the unknown and taking on adult responsibilities. What is where I Understood the concept of taking risk. I truly believe that taking risk is the most important part of one’s life. At the age of 33 When I became a mother , I decided to take the biggest leap and risk of my Life. I went from full-time corporate and part-time small business entrepreneur to them becoming a full-time business entrepreneur. Read more>>

Kia Leiani

Leaving my 9-5 and making my entertainment career full time. Taking a risk and really putting in the work to make this a reality. From casting calls to actually landing roles and being featured in films. Also, stand up comedy is something fresh but I’ve started doing comedy shows and really loving the craft! Music has always been a priority so adding more crafts to my plate has really been a great risk I’m glad I took. Read more>>

Crystal Charles

Taking a risk can be scary but DO IT! “If it’s still in your mind, it’s worth taking the risk” Paulo Coelho once said. I remember late 2020, I wanted to quit my 9-5 retail job because I was so miserable and wanted to pursue my wardrobe styling business full time. For months, I kept asking myself: How would I survive with no consistent income? What if I fail? Will people book with me.. etc. all the doubtable questions you can think of. Until one day, I told myself “you will never know unless you take the risk”. Read more>>

Nick Snow

In most cases, when we look back on truly life altering decisions, it’s done with the benefit of hindsight. The biggest risk I ever took was a decision that I knew would reverberate forever in my life – and I was only 21 at the time. The biggest risk I ever took was dropping out of college and moving out of my home state. I was a gifted student, but I was lazy and unorganized. I was nearly failing out of school and completely burnt out. I wanted nothing to do with my major and nothing to do with school. I made lifelong memories and friends, but I also know that I wasn’t mature enough to fully take advantage of my time in school. Read more>>

Hope Hughes

We all experience defining moments in our lives. Mine happened in 2018 as I was nearing the end of my chemotherapy treatments for breast cancer. It was a pivotal time in my life. The realization of a potentially life threatening illness has a way of paring down society’s extraneous expectations and forcing us to narrow in on what’s truly important. I knew I wanted to do more than sell real estate all my life. Although I was quite passionate about it throughout my career, it was beginning to lose its shine so to speak. And with my daughters grown up and out of the house I had time to pursue other interests. Read more>>

Jalia Pettis

Ever feel like you knew you were destined for more? That is exactly how I felt when I relocated to Arizona and decided to work my business full-time. I quit a full-time corporate job, packed up my belongings, put my three kids in the car as a single mother and drove cross country. I felt like I had reached the cap of where I was in the job I was in and the place I lived. It was time for me to take a risk or what I like to refer to as a leap of faith. I had several people who made comments on my decision both discouraging and encouraging. However, I knew that is what I needed to do in order to allow what I visualized within my imagination become a reality. Read more>>

Keyring

Back in 2020, I ended up boarding a one-way flight to NYC with $300 in quite the trope fashion. I ended up miraculously finding a job and a place to live thanks to community support when I needed to spend time, not at my biological family’s house. During my year living there I did digital drag shows, performed maskless at some parties that I definitely should not have been at, cried, celebrated the de-election of Trump, and more. I actually have written a short memoir about my time in Brooklyn but I’m unsure about the best time to release it. If anyone reading this bothers me about it I just might put it out, or hold onto it forever out of spite :) Read more>>

John Burns

For us it seems like the biggest risk was making the decision to start the business in the first place. We had a fairly comfortable life and jobs that many people would be happy about. At the time we had four children, with three in their teens. They were all involved in youth sports, trying to succeed academically, and had active social lives. (Little did we know that kiddo number five was coming right about the same time we were going to take this leap.) My point is that life was already busy enough and the bills were getting paid. Why take any risk at all? Read more>>

Ariella Beamon

When I started my spa business in 2018, I trained with multiple skincare lines and choose one to retail within my business. From 2018 I retailed a major professional skincare for my business. But in 2021 I decided to release my own all natural corrective skincare line called Skin on Beam. Taking this risk was scary; I had to invest thousands, took a lot of losses, and totally rearrange my personal life schedule and business schedule. Read more>>

Sabreena Covington

I lived in Maryland for most of my life. I was undervalued and unfulfilled with my job, but I had been with my company for 20 years. Who leaves a company after being there for 20 years? Well, I did. I didn’t just leave the company, but I left Maryland, my family and my friends and moved to Texas. This was a big, life changing risk. We didn’t know anyone in Texas, but my family and I took a leap of faith. Even though it appeared, we were moving because I received a new job opportunity, we were really moving because it was part of God’s plan. God had to move me out of a comfortable and familiar environment to see if I would trust Him and this was just the beginning. Read more>>

Jenny West

I have had my own business practicing Medical Massage for several years. Once my husband retired from the military in 2016, he started up a brand new business, and asked me to join him. It was a completely different industry, a completely different mindset, brand new people, places and experiences. I took the risk and decided to join him. In the security industry, there are several hard skills that are common among all of the practitioners: shooting, fighting, driving, protecting, exploring, all while providing top notch customer service. The security industry is still a customer service industry, and there are many ways to gain a customer, and many ways to lose a customer. Read more>>

Jessica Gil

Putting yourself out there, in the public eye, is always a huge risk. You risk emotional losses, financial losses, and rejection is never easy. The possibilities of financial failure are very real, as well as the risk of people not liking your product or services. I took that risk starting Satnin Polish, my hemp oil infused nail polish line. But I have also taken that risk recently by finally singing in a band, The Rebel Hearts. Its been a dream of mine since I was a child to be a singer. I would sing “Part of that World” from “The Little Mermaid” everyday in my first grade class. I joined all the chorus classes I could all the way through high school. But as I grew older, I also grew more and more shy. Read more>>

Robin Finney

I feel like my life is full of risks, taking chances, and leaping into the unknown. I’ve taken many leaps over the years and one of the most notable is when I left my corporate career to travel the world. When I started my career in the multifamily industry in 2007, I developed a “work to travel” mentality. I would work, save up money and vacation time, and then take a big trip each year with a couple of friends from college. We traveled to countries across Europe, Australia, New Zealand, Iceland, and several countries in Africa. While these trips were thrilling, I would come home with a sense of longing and wanting more. Read more>>

Rachel Ritter

We saw the need for fashionable roller skates that are fairly priced. We weren’t happy that the current brands out there were using subpar materials just to make things affordable. We wanted to offer budget friendly components that are still higher quality so beginners wouldn’t have to spend more money just to have to upgrade soon after. After a brief conversation where we just happened to be on the same page, we decided to just go for it and start producing our own line of recreational skates. At the time we were designing our own apparel to send in monthly subscription packs geared toward people that roller skate. We had been doing this for 5 years and it just felt like a natural progression to level up and offer another aspect to the roller skating lifestyle. Read more>>

Jodi Carey

Does this have to be related to teaching? or anything? Here are two and you can choose: Born and raised in NYC, when I turned 18 I was the epitome of a teenage independent thinker/artist with unconventional aspirations; attending college was not on the of my list. However, I did end up at a university in the midwest, not based on my grades and SAT score, but with a recommendation letter based on my role in a performing arts company affiliated with the university. My mentor at the time was the theater director there and I was just beyond grateful for this relationship and opportunity, as for the first time in. my life I started enjoying “school”. Read more>>

Danielle Aikens-Holland

I knew I wanted to own a dance studio and teach music lessons as my career around the age of 10. I never wavered in what I wanted to do because I loved dancing and playing the piano so much, I just had to share it with others. My husband knew that this was my dream, so we set off to start getting an idea of what it would cost to rent a space. After driving around all day and calling for prices, we were very discouraged and not sure how we would ever manage to afford a lease that was so expensive. At this time, we were only 8 months into our marriage, and I was a junior in college. Read more>>

Andrew Daniel

As I approached graduation day for my Master’s in Music degree from the University of Southern California, I realized that so many of my colleagues that graduated ahead of me were having a difficult time finding work. They were going back to school, pursuing alternate degrees with the promise of lucrative employment. I had already spent an enormous amount of time learning the craft of classical guitar and was determined to not be derailed from my musical journey. Read more>>

Marina Gonella

The biggest risk I took in my life was almost 20 years ago when my husband and I decided to relocate from Argentina to South Florida. Although I am not originally from Argentina since I was born in Chicago to Argentinean parents, I grew up in Buenos Aires surrounded by family and friends.
So, leaving everything behind and taking the risk of migrating here with my husband and a 4 year old daughter was very hard. At the time we made the decision, the political, economical and security situation in Argentina was complicated. Read more>>

Mandy Hancock

In my experience, taking a risk and getting out of your comfort zone is where we really grow as individuals. Not necessarily knowing how things are going to work out but taking that first step anyway can be scary, liberating, terrifying and exciting. But the important thing is that we take that first initiative. I’m a firm believer that the Universe is always working in our favor. Having that trust, a passion for your work and the confidence to take inspired action is the recipe for entrepreneurial success. Read more>>

Karrington Sneed

The biggest risk that I’ve taken was taking a break from college to pursue my music career back in 2020. I think the hardest part for me was falling through with what my heart truly desired the most. I’ve always pursed the dreams of others rather than my own.. unconsciously. We strive for our friends and family to be proud of us even if that means doing what they want. That’s where my fear peaked in. It’s not that I didn’t have a great support system or parents that didn’t believe in me because I did. Read more>>

Peter Toth

High altitude mountaineering and rock climbing is high risk high reward. It all started when my son was about 15 years old and a high achiever academically but I wanted to teach him about my love of outdoor adventures. I took him rock climbing on a trip to Colorado. We both pushed the boundaries ever higher. I eventually started climbing high mountains all over the world. My highest was over 20,000ft. in ice and rock. Together my son and I climbed many peaks in the US, Mexico and Killimanjaro in Africa. Read more>>

Roberto Jolliffe

In the summer of 2018 I was taking monologue and acting classes locally in San Antonio, Texas. I started taking these classes because I seen so many shows on Netflix I was like I have some ideas I want to turn into a show. So for me when I want to learn something or be involved I dive in and commit all the way. One day a prior student came to the class to tell us his experiences in LA at the Groundlings Improv School in LA. Then it hit me like I have to get out of my comfort zone to learn and really see if this is for me. Read more>>

Jamie Papish

When I was a teenager, music was my passion. I went to concerts every week and all my social interactions revolved around music. I took guitar lessons as a child but never really worked at it and was never really encouraged. As a teen, I was a frustrated guitarist and eventually gave up. My dad was an accountant and always pushed my brother and I to have a profession. He believed that security was the most important thing and once you made a good living and supported your family, then you can do whatever else you wanted. Read more>>