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.
Vincent Biffle

The biggest risk I have taken in my life was moving to Atlanta with nothing really under my belt besides a college degree, ambition to start my own business, and faith in God that everything will work out. I was 23 years old when I decided it was time for change. I had just recently dropped out of graduate school and did not know which direction my life was headed in. Read more>>
Cheyanne Glazier Chloe Cosette

Back in February of 2022, we had the idea of starting C&C Productions. We were both still in college and were looking into the future. What was next for us? We wanted to be able to work in film and video production and not have to stumble once we were out of school, so C&C Productions was born. It was taking a huge risk for many reasons. It is not cheap to start a business, and it also isn’t easy. Read more>>
Hasan Morrison Jr

One of the major points in my life where I took a risk was moving to Los Angeles, California during the pandemic of January 2021. I am from Philadelphia born and raised which is a callous place with so many trials and tribulations as growing up an inner city kid. I never thought much of relocating so soon in life until I went on my first trip ever. I went on my first trip at the end of 2020 to visit LA which changed my whole perspective and allowed me to shift my mindset pertaining to business and growth. When I first arrived in LA I noticed a different energy that I wasn’t used to and seeing so much success nearby motivated me immensely. Read more>>
John Shute

In 2016 I was a Marketing Director for a cannabis contract manufacturer in California. My intern and I helped them generate a ton of revenue in the first year we worked for them, so they promised us a long-term position with salary, benefits, etc. About a month before my wedding, they fired my intern and told me they couldn’t employ me any longer. Read more>>
Jenny Sharpe

I’m a college graduate used the degree for awhile. But ended up working for my mom in her restaurant because I wanted to be able to spend more time with my kids. My degree has me working long hours and missing everything. Which then turned me to baking. I’d bake here or there help with sweet treats at the restaurant. I then started making my kids cakes which lead to years of helping friends. Read more>>
Christabell Nunez

I took a big risk to be a vulnerable Latina in the public eye. I have been working for years as an advocate for body positivity and mental health, particularly for women with curvy bodies. I also support small owned businesses and a am proud philanthropist in the Austin community. But there was something missing. I wanted to step out of the shadows and use my voice to make a real difference. Read more>>
Krystal Moreno

My topic is really a cross between starting a company and lessons learned and the biggest risk coming out of the pandemic. The hospitality industry, like many industries, that was severely impacted by COVID-19. As a long term Catering & Sales Director in the hotel industry, the shut down began in the middle of a large program I had for a hotel I was working for in Santa Monica. Read more>>
Damon Ruff

Truly, Throughout this entire process of being a private chef. I had a vision in my early 20s but never pursued it. My mentality now is I’m thankful I manned up in 2018 and learn the craft. I’ve been flown to different cities, said yes to events I didn’t make a lot of money from, and I’ve driven miles in my car. To me that’s the true risk, believing in your WILL POWER. The saying is the Bigger the Risk, The Bigger the Reward. In three years I have been able to accomplish just about every goal I have wanted to get done. Read more>>
Camisha Perren

The biggest risk that I took during this journey was taking a leap in faith during Covid-19 to open up my own business. As a college student, a mother, a teacher, and a wife, I already had a lot of responsibilities at the time. But regardless of the obstacles, I knew what I wanted to achieve and my family and friends encouraged me each step of the way. I spent countless hours planning every detail of my business. Because there were so many small candle businesses springing up due to Covid, I wanted to make sure my brand stood out and truly represented who I am as a person. Read more>>
Anni Lee

Risks scare me. Im not a risk taker. I play it safe, by the book, and through a traditional lens. That’s what I thought until doing a deep dive and self evaluation of my life. If I was playing it safe, I wouldn’t have traveled across the country from Southern California to Maine to go to college. I wouldn’t have moved and accepted my first nursing job in New Hampshire at a Level 1 Trauma Center. Read more>>
Demetrius Angelo

The Bible declares in the Book of James that Faith if it hath not works is Dead! This powerful statement has always put the ideals of following one’s dreams into perspective. We all have dreams and aspirations yet most of us talk ourselves out of or allow others to talk us out of pursuing those dreams and perhaps even our destiny. Read more>>
Julie Speetjens

I am a Psychic Medium, a truth which inspires some people but invites ridicule and judgement from others. Luckily, their fear and ignorance does not diminish the value of what I do. I have seen a good Reading save people from decades of anguish, release them from the crushing grip of grief, springboard their spiritual awakening, and reignite eternal bonds of love. Read more>>
Kirsten Hellmer

The biggest risk I’ve taken would be taking my business full time. About 4 years ago, I was working as a corporate data analyst and was completely miserable. I had gotten my bachelors in Marketing and masters in Market Research/Data Analytics from Michigan State University, so being a data analyst was the next obvious step. I had been working as a data analyst for about 5 years when I discovered the laser cutters at my local makerspace, i3Detroit. Read more>>
Peggie Lyons

Last year, PJL Candles was a vendor for Earn Your Leisure’s Invest Fest, which is a huge financial festival in Atlanta. A friend sent me information about it several months prior, and once I saw the vendor fee….I did not feel like my company was ready for something of that magnitude. I had so much doubt, and I was ready to say no right away. My friend truly believed in me and my company and was super encouraging and made me feel like I could and should do it. Read more>>
Alan Hyde

A risk I have taken was the time I transitioned from military life to civilian life, I had served over half a decade in the US Army and decided that I wanted to pursue a career in entertainment. I knew it was a risk because there’s always the known whenever there is a career change. I loved serving my country and dedicating my life to being in the armed forces, but deep down inside I wanted to pursue something that I was passionate about, and that is the world of entertainment. Read more>>
Victor Lopez

The most risky move I have taken starts when I was 18 years old. After I graduated high school I knew what I wanted to be, but I didn’t know the best way to go about executing the idea. A business owner was all I could think about even as a young child. I tried college, not just once, but twice and it simply didn’t feel right. I felt out of place each day and unsure if I was making the right decisions although I knew what I was going to school for, business administration and automotive & high performance tech, was what I knew I was good at. Read more>>
Natacha Voliakovsky

Making socially engaged art is always a big risk. As a South American survivor and high testosterone women, making art as a form of social claim is not an easy path. My performances do not seek to be attractive, but their mission is to make visible many injustices and problems that we face today as society. Read more>>
Demi Cortez

Life is all about taking risks and wholeheartedly believing in yourself. That was the biggest lesson I had to learn as an entrepreneur and business owner. I dreamt about what I have accomplished thus far in my career and have a very optimistic outlook on the future to come. When I decided to leave my full-time job to follow my passion it was scary. Terrifying actually. It was the best risk I could’ve taken on myself. Read more>>
Natacha Voliakovsky

Making socially engaged art is always a big risk. As a South American survivor and high testosterone women, making art as a form of social claim is not an easy path. My performances do not seek to be attractive, but their mission is to make visible many injustices and problems that we face today as society. I use activism-based-practice and performance pedagogy to address my work towards social-bodies. Read more>>
Kali Edwards

When I started my business in 2013, everyone was building big websites with long, drawn-out timelines. I worked as an agency Art Director at the time, and I once spent almost two years on a website between client feedback lags and a poor process outline. I started June Mango because I knew I could do it better. I launched June Mango with my signature Go Live in 5 web design process. During the Go Live in 5 process, I would design AND build a website in just 5 days. Read more>>
Jennifer Agee

In 2018, I was feeling burned out and stressed out. At the time, I owned a solo-private practice and although I absolutely love being a therapist, my first passion is being an entrepreneur. I was not honoring that part of myself at all and the monotony of daily practice was draining my energy. Read more>>
Christian Johnson

In 2019 I quit my job and bought a camera, a drone, a GoPro, and a one-way ticket to Italy to fulfill my dream of traveling the world and running an online business. At the time I was working a full-time dead-end job as a nanny in Hollywood. There was no corporate ladder to climb or promotion to be gained, and despite how much I loved exclusively working for that family and caring for their children, I knew I needed to learn skills that would build a sustainable career that would provide the lifestyle I had always dreamed of. Read more>>
Audra Agen

Starting a podcast is definitely outside my comfort zone, especially one that requires you to be vulnerable. That’s why my show works; my vulnerability allows my guests to be comfortable with theirs. Getting to this point wasn’t easy and I needed to be pushed to do it. I started this platform as a form of rebellion. I was tired of being overlooked and unseen because my value and contributions didn’t look like my male counterparts. Read more>>
Anita Alberto

I was a single parent working at a grocery store full time. I started studying photography for fun. I enjoyed photographing people and was asked to photograph a small wedding. Without hesitation I said yes. It was an amazing experience and confirmed that I wanted to pursue a business in photography. I had a lot to learn. I took more photography classes and quickly started to build my clientele. I also began networking with other business owners. Read more>>
Nikki Lawrie

I left a very secure leadership position at a well-respected non-profit, where I had worked for nearly a decade to start my own business. I made the jump with only a few thousand dollars saved. I was also a single mother at the time. I jumped not really knowing what I was doing and had to figure every aspect out very much in the moment. Read more>>
Yanet Borrego

I worked for 9 years in corporate with two wonderful Fortune 500 companies as an Engineer, Supply Chain Expert, and Management & Strategy Consultant. In those 9 years, I also built my coaching practice on the side, got certified as a coach, speaker, and trainer under the John Maxwell Team, got board certified by the Association for Integrative Psychology as a Master Practitioner, Trainer, and Coach of Neuro-Linguistic Programming and Hypnosis. Read more>>
Elizabeth Sanchez

One of the biggest risks that I recently took was to start my own mental health podcast. I have been a therapist for the past 10 years and worked and different settings but never have I ever been apart of a podcast. I decided to take a leap of faith and start Cafecito y Calidad a mental health podcast that aired March 1st 2023 on YouTube, spotify, and apple podcasts Read more>>
Shanika Henry

Taking risks means leaving your comfort zone to achieve greatness, That doesn’t always mean we get it right, and that’s ok, failure oftentimes equate to growth. I’ve always tried to bet on myself when it comes to accomplishing my goals. Growing up I was taught to play it safe, go to school, get a job, and retire with a pension. For me, that didn’t seem too rewarding but, leaving that comfort zone is scary. Read more>>
Jamie Maglietta

My career has been built on taking risks, rejection, and reputation. These three Rs are essential to success. My recent decision has been the biggest risk of all, after being laid off after my show on CNN was cancelled I decided to invest in myself. After years of working in TV news I decided to make a change and pivot. At first the risk was rewarded. I began freelancing in unscripted production management as a Line Producer. Managing live TV shows had more transferrable skills into this new line of work than I initially realized. Read more>>
Tez Hailu

My friends that know me would describe me as a person that is careful and calculated. This can be a good trait or a bad trait to have. One example I have is, while I was running my own business (Silent Echo Studios) a childhood friend of mine called asking how he could start his own business (Cleaning Service). I shared the information with him and roughly a few weeks later he asked if I could meet with him on a weekly basis to go over ideas and planning. Read more>>
Nikita Desa

Participating in a skydive! Which ultimately led me to the path that I am on now. Around nine years ago, I organised a charity skydive at my workplace where I was at the time. Upon landing, I injured my lumber spine which caused a fracture and I immediately knew something was wrong. After several appointments with specialists and doctors, I was advised that the only way to fix the injury was to have a major surgery where a disc would be removed and a metal cage would be placed around the area. Read more>>
Maggie Wu

I will finish my Bachelors degree in Fine Arts (Painting and Drawing) in May 2023. I would have never thought of graduating as an artist when I was younger. Being a first generation college student in the traditional Asian family, my parents would expect their children to take on big name careers like computer science, engineering, or doctorate fields. In high school, my original plan was to become a software engineer. I have never coded before, but I was a fast learner, great with computers, and just wanted school to be over with. Read more>>
Amanda Canales

In March 2020, I got laid off from my marketing job. Like everyone else I took the 2 week break and realized that the world wasn’t going to be the same. I had freelance social media clients thankfully, but I knew that something had to charge. While I applied to marketing jobs I also pitched freelance social media clients. I realized that I needed I closed 2 freelance clients and had interviews but I wasn’t landing anything. Read more>>
Gen Li

Taking risks is an essential part of achieving success, especially when it comes to pursuing your passion. As a young undergraduate student with no prior art-related background or knowledge, I faced a difficult decision during my senior year. Despite the job market favoring science majors, I decided to take a risk and follow my passion for visual effects. Read more>>
Laniece Listens

It was a hot summer day in July as I prepared for the meeting that would change everything. I rehearsed the lines over and over in my head and even out loud in the mirror. A week or so prior to this day, I called a meeting with my flight chief. During this meeting, I was going to request support as I prepared for my husband to be deployed for 6 months. I had been working in this government position for almost a year. Read more>>
Mary Langlois

During the pandemic, I was not creating and doing aerials. I, like most others, was sad and scared of the way the world was. As the pandemic lessoned and the world started to open I was excited to get back to teaching at the studio I was previously at. But to my chagrin, they closed their doors not to open for a while if ever. That little gleam of hope was dashed. Read more>>
Kamau Tafari El

Life is about taking risk. Healthy, well thought out and calculated risks are necessary to achieve your goals. Chance meets opportunities when you take risks but chance never meets opportunities if you only sit on your thoughts. My big life changing risk I personally took was to believe in myself and fully immerse myself into being an entrepreneur. I have always been creative since a youth and a very intelligent person. Many say I have a creative and great perspective on life. Read more>>
Sydney

In 2019 I decided to take a leap and start my own business. I have been assisting for a long time, but outgrew the position I was in. There was no more growth for me where I was currently at the time. I knew the only step up was to make a leap. I was scared but I knew if not now when would I ever do it.It was the best decision I’ve ever made. There was no look back it just felt so right. Read more>>
Sonya Blesofsky

My art practice is unusual in that it’s very improvisational. I make site-responsive installations, and each installation gets made on-site, in-the-moment, based on what I find in the process of excavating or researching a space. Every installation I’ve made has been structured around the possibility for failure, and involves some sort of risk-taking. Read more>>
Mariela Aguirre

The biggest jump with the highest risk would have to have been leaving my safe corporate job of 16 years. I loved my job and what I did, however, the newfound world of real estate was a world I wanted to be a part of. All the pieces were coming together one by one that the decision was almost too obvious. With the leap of faith, I went on to pursue real estate and have not looked back. I know for certain this is where I am supposed to be and will pave its way to the road I am after. Read more>>
Christa Hines

Entrepreneurship can often feel like a heady ride on a roller coaster. Some days you’re slowly trekking up the hill toward your goals and all is calm and peaceful. Other days you’re riding the high of a stomach-in-your-throat drop with the air whistling through your ears. And on other days you’re getting jerked around on a twisty learning curve! Some days you get all three. Although I can hardly be described as an adventure junkie, I love how I’m always learning through owning my own business and how no day is quite the same as the day before. Read more>>
Leslie Collins

I wanted to create a podcast that was inspired by my father and his tradition of telling incredible and hilarious bedtime stories. When I created it, I thought, “Hey, why not have Dad tell a story live, record it and then have improvising comedians voice all of the characters.” It brought together two of my favorite things, bedtime stories and improvisation. At the time, podcasting was just starting to happen but not for a children’s market. Read more>>
Tijuana Hairston

I started off by doing my friends and family’s hair, with doing so I never thought this would be something I’d continue doing as an adult. As the years went by I began to realize and understand how so many individuals loved to change their look which made them feel much more beautiful as they already were. Wigs, bundles and extensions were becoming the highlight of people lives and they were loving it and so was I. Read more>>
JJ Hardy

The big risk I took was when I decided to leave my job and start a business. It definitely was not an easy decision to make but I knew it was time. I was lucky enough to work for a company that knew it was my time to go. I helped them create a leadership development program and always had a passion for developing the people in my organization on the principles of leadership! They knew that starting a business is something that I wanted to do and they supported me in that decision. Read more>>
Susan Pohlman

On a business trip to Italy in 2003, my husband Tim and I took a break from entertaining clients and walked along the Ligurian sea where Christopher Columbus had learned to sail as a boy. The elegant beauty of Santa Margherita lulled us into silence as we ambled along, lost in our own thoughts. We had been married sixteen years, had two beautiful children, a cozy home on the outskirts of Los Angeles—and we were, quite frankly, sick of each other. Read more>>
Melina Crabtree

When my daughter was born, I wanted to spend as much time with her as possible and I knew I didn’t want to return to my time consuming corporate marketing job. So I took a leap of faith and started a wellness business with Sunrider offering moms the best plant based products for their family and a side business they could do from home. Read more>>
Gladys Bortot

I am a person who takes risks, I do not like staying in my comfort zone. The first one I took on a professional level was leaving my job at the advertising agency, a career I studied, to work in my father´s art gallery, that’s when I realised that it was something that I really liked. Read more>>
Rosia Parrish

Once I graduated from CU Boulder, it took me another seven years to complete pre-medicine required classes and apply to naturopathic medical school. I actually also applied to conventional schools to be an MD or DO, but deep down, I’d always wanted a nonconventional approach to care the valued lifestyle, nutrition, and better living than the mainstream approach that is often centered around pharmaceuticals and surgery. Read more>>
Maria Delgado Gambini

My sister and I officially opened up our business together in the winter of 2011 and has been the absolute biggest risk we have ever taken. It took a lot of work, but it took a lot of heart too. Leaving our former jobs to open up something from the ground up was something that really tested our minds, bodies and the relationship we had with each other. Read more>>
Anne Archambeault

I started my career as an elementary school teacher. My love of learning and working with children came naturally to me. I loved to be in my classroom and work with children and watch them grow. When Covid hit, I was unable to have the same level of interaction with the kids. The struggles of virtual learning and not being able to interact with my students became increasingly difficult. I woke up one morning during the summer break and decided that I wanted to explore some other options. I fell into insurance through a friends referral and fell in love with it. I could still teach and help people. Read more>>
Kevin Kehoe
My mission as an artist couldn’t be simpler. My mission was to answer the slightly daunting question…”What if?” “What if I became an artist? What if I became a photographer at the same time as becoming a painter? What if became a storyteller about becoming both a painter and a photographer? What if I left my successful thirty-year career in advertising to do all of the above?” What if I took a risk the size of Utah? “What if? What if? What if?” I wasn’t interested in a partial answer either. I was after the whole enchilada of an answer. Read more>>
D’Asia Scott
I started my business in the middle of a pandemic! (COVID-19) After being let go from a large franchise company due to sales, I used my last $3200 I had in my savings for start up costs. Not knowing if I would succeed or fail, just literally having faith and a clientele that believed in me. I purchased a suite, inventory, materials etc. and things took off! I eventually outgrew my small space and was able to put all of the money I made from services in 2020 back into my business and lease a storefront in March 2021! Read more>>