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.

Nicole Derderian

My biggest risk was taking my entire business online! I started coaching in 2020 and from Jan 2020-Jan 2023 I always had other “main sources” of income (medical assistant, nannying, in-person trainer). The number one reason why I always failed to grow: I was afraid to go “all-in.” In Jan 2023, I had the experience and support to finally make the jump to working for myself and only myself. Read more>>

Melanie Delgado

In 2008 I decided to move across the country from New Jersey to California. I didn’t know anyone out there or any idea what I would do when I got there. I had faith it was all going to work out. Radical change felt necessary at that moment of my life. I was 30 and ready for serious change. East coast vs West coast. Big differences but I certainly found myself grounded in a community of people who were looking for freedom. Read more>>

Sarah Floyd

I remember so clearly the moment I decided to open my own private practice instead of joining a group practice as I had originally planned. I recall driving home late at night after picking up some ice cream and hearing my inner voice tell me “Sarah I need you to be big. You are living too small and I need you to be bigger please”. Read more>>

RHONDA SPRATT

Over thirty years ago, I took one of the biggest risks of my life. I relocated to Georgia from my home state of Oklahoma City without a job or family members to rely on; only my Faith and I was determined to carve a new life for myself. Through the years, I have connected with a network of associates, established friendships, purchased homes, started a business and a non-profit, gave birth to a beautiful daughter, and created an amazingly comfortable life for myself. Read more>>

Jordan Oram

I took the risk to start a business for an animation IP that me and my partners are selling. We got extremely far in the sale of our IP to Netflix, but ultimately lost it because of Netflix USA cutting their Animation department by 90% to focus on their own IPs which they had bought the rights for. We realized the value we had considering we made it that far, and ultimately decided to start our own animation studio to produce our IP. Read more>>

Irving Lambert

Being the fearless risk-taker I am, one of my most daring leaps was leaving behind a stable life in Michigan after college. The allure of chasing my dreams in LA was too strong to resist. Despite mixed reactions from supportive friends to skeptical critics, I sold everything, slept in my car on the west coast, and tirelessly crafted content. Read more>>

Carmen Friday

Four years ago, I made the risky decision to quit my job of over 17 years in retail management to start my own business. That small voice was continuing to grow louder telling me that I deserved more than clocking in and out of someone else’s schedule and answering to someone else’s bottom line. Read more>>

Amelie Held

I feel like my whole life can be described by just one simple quote: “No risk, no fun!” I never really listened to people telling me what to do or what not to do. Everyone kept saying, I should not go into music. It was always the same: You will never find a job, you will never have any financial stability, you will never make enough money, you are better off studying law or medicine. Read more>>

Natali Ormani

I was always a free spirit but didn’t know why I was so different when I was younger. Why couldn’t I be a normal employee? And why did I feel like being in jail when I wasn’t able to decide about my life? Why did I always desire to see the world and be in Latin America as a kid? I had just a few employee jobs but this didn’t make me happy and satisfied. Read more>>

Marnie Vincolisi

Life does not come with instructions or a glossary so there was no reference point for me to access when I knew change was at hand. I just needed to trust life’s messages and to go with the flow. It took about two years to fully move into a place where I could make a change. The message to move on to a new vocation at first came in a soft voice but that voice became louder as time went on. Read more>>

Anna Barr

I love this question and don’t even know where to start. The first risk I took was becoming a mom when that was never my plan. Then homeschooling my kids when I said I would NEVER do that. Are you seeing a theme here? Then when we were about to lose our house due to financial hardship I went from not even remembering how to turn on a computer to working online in the online teaching space (before this was a thing really). Read more>>

Savy The Creator

Taking risks is an essential part of building a successful brand and achieving your goals. For me, the biggest risk I’ve taken in life was starting my own talent development company. I had no idea what the outcome would be, but I had to trust in myself and the calling that led me to this path. Read more>>

Daniel Gutierrez

In my process taking risk was my only way for true joy, making risky choices mainly monetary and luxurious sacrifices in order to be available to my art, to get major results you need to have the time to earn and master the skills you have to decide do you want to be a professional or is it just a hobby? Read more>>

Jill Stoddard

Willingness to take risks is probably the biggest way I have grown in my career. Most notably, I had an opportunity to give a TEDx talk–a bucket-list-professional-dream I had on my list of career goals. I had been preparing but wasn’t ready when the opportunity arose. It was during the pandemic and I had gained a lot of weight which *logically* I knew shouldn’t matter, but I had been called names as a pudgier kid and memorializing myself on video at a time I felt desperately insecure just hit too many of my old tender spots. Read more>>

Vitorio Nicholson

A big risk Ive took in life is starting a wine business and starting the vineyard in east Colorado. It was such a big risk due to the fact that one I never grew up with wine or knowing about it and two I had no idea on where to start and how i was going to get started on a vineyard and grow it. Luckily enough for me an old friend of mine who has experience and knowledge with wine; seen what I was wanting to do and wanted to join forces. Read more>>

Patrick Shepard

Being calculated and taking proper risks has gotten me the furthest in my artistic development. I worked as a barista at UofM hospital for more than 4 years before I got my first national/international tour with The Black Opera(a hip-hop crew based out of Detroit and Ann Arbor). It was here I had my first decision to take the risk of leaving my comfortable corporate job and pursuing my dream. Read more>>

Thomas Musil

The whole beginning of being a DJ (Full Time) is a risk in its self. Even though the public perception of DJing has got much better then in the past, it is still something that a lot of people don’t consider a “real job” so the risk factor can be big. In my case it was an “all in” situation. I had to borrow money from my mother because we weren’t a money family. Read more>>

Jeff Leach

Over the past year I wrote, performed, self-produced and directed my debut stand-up comedy special. It was a labour of love and a process that provided me immense learning even after twenty years of professional work in my entertainment career, As the changing landscape of entertainment continues to evolve and shift I felt that it was more important than ever to retain creative control over the art I put out into the world and the way it reaches my audience. Read more>>

Eric Bonham

At this point in my life, I feel the biggest risk that I have taken is starting my woodworking small business. It wasn’t a crazy life or death risk, but a calculated and planned out sacrifice to challenge myself and do something that I truly enjoy. Being a teacher and Coach before for seven years, I decided to take a chance and try something different. Read more>>

Polly Walshin

Life is full of risk. If you don’t risk anything, you’ll never know the possibilities and the highs that you can reach. When the world was shut down during the pandemic, I decided to write a book. At the very same time I decided to open my own business ,and also sell real estate. I have been in the real estate business for over 20 years . However during that time. It was very hard to show properties and my passion was health and wellness. Read more>>

Michelle Pusateri

When I started Nana Joes Granola in 2010 the landscape for small businesses wanting to enter the Natural food manufacturing sector was a very short runway. There weren’t many books, podcasts or even coaches to help. I decided I wanted to start a granola company as a side hustle to my pastry chef job. I never imagined we would grow into a legitimate certified gluten free granola company. Read more>>

Alyssa Cass

For my latest music video for my single “New Moves,” I knew I wanted to shoot this fun 80’s themed dance music with this pink and blue color scheme. I found these amazing locations that perfectly matched the vision in my head but admittingly were a bit outside of my budget. I decided to go ahead and take a risk and bet on myself and the song. I ended up splurging on five different set locations in total and I even got robbed at one of the locations in DTLA but if you asked me if it was worth it, I’d say yes and I would do it again in a heartbeat. Read more>>

Jenny Evans

As an entrepreneur, taking risk is a huge part of the job description – whether it’s stepping onto to the MGM Grand stage in front of 18,000 people, firing a client that was 90% of my business but no longer shared my values, self-funding product launches, or putting myself into business scenarios that are a stretch, I like to give myself the benefit of the doubt. Read more>>

Domanique Lawrence

The biggest risk i ever took was becoming a doula. Imagine this, you’re 21, just graduated from MTSU with your public health degree, and you feel like you aren’t sure what you should do next. You know what you want to do in life isn’t aligning with your degree and your current career. I found out about the world of birth work at 16, and it’s been eating at the back of my mind. In Spring of 2023, before I started Nursing school, I told myself “Let me do this one thing for me first”, and I did. Read more>>

Melanie Porter

I’m Chef Lynn a local Kansas City private chef, and caterer, but also known as “the risk taker”. I’ve been taking risk for most of my life with just about anything that I felt was risky. The unknown is scary to most but influential to me, if you never take a risk, you never know what the outcome will be. I should know because six years ago I took a risk and started my business and still did not get my business up and running legitimately up until four years ago. Read more>>

Taz Street

I took the risk of creating a business with another experienced facilitator who is a successful business person. We only knew each other online and through Zoom meetings. We both had the same vision of how we wanted this business to be and how it would support others. Read more>>

James Dean Johnstone

Being a digital creator you are vulnerable to people online. You show people your life through a camera and sometimes it can be scary. I have a podcast “Hot Shots: A Sports Podcast” (@hotshotspodcast on all socials) and I remember being nervous releasing my content. I. made sports content for years, but only centered around my high school athletics. Read more>>

Christina Phavilay

When was the last time you walked away from a good thing? Have you ever left a situation before it got past the point of no return? Why would you? My life seemed fine and I had manifested so many things that I had only once dreamed of having: the boyfriend, the travels, the home. I was making strides out of debt and growing in my career. Read more>>

Sharon Clawson

Working anything outside of your typical 9-5 wasn’t even a thought for me, especially coming from a Southeast Asian background. All my mom ever worried or cared about was having a sense of stability and to her, that meant working anywhere in the medical field. She was an LVN nurse majority of her life, therefore inspiring me to pursue a similar path. Read more>>

Hassan Dahik

I’ve always considered myself a risk-taker, perhaps even a bit of a player. At the age of 22, I ventured into the unknown, leaving everything behind to pursue a dream in California. Armed with just my bass and guitar, I embarked on a journey in the heart of the gold rush state. While taking risks may not be everyone’s cup of tea, I wouldn’t trade the life-altering decision I made in 2015 for anything else. Read more>>

Britnee & Dorian Alphin

Being highschool sweethearts and later business partners already comes with basic risks (example: burn out from each other). One of the biggest risks we’ve taken is choosing to make our relationship public to inspire others. When we created our platform (on accident) we didn’t anticipate that the reach would be what it is nor did we have a clear direction or goal. Read more>>

Dakota Smith

Taking the risk of having a home birth was the most life-changing decision I’ve ever made. Some might see it as a big risk, others not so much. Personally, the idea of labor and birth terrified me, especially since it was my first pregnancy. My husband deployed to Japan when I was 6 and a half months pregnant. Wanting a natural birth, I veered away from the idea of a hospital birth. Read more>>

Laura Suttin

One of the biggest risks I have taken was starting my own business as a life coach for physicians. I decided to become a coach in 2019; a physician colleague of mine had recently earned her coaching certification. At the time, I was leading several physician engagement and mentoring initiatives in my healthcare organization, and had also participated in personal development work for 5-6 years. Read more>>

Leslie Lerner

Starting Leslie Lerner Properties was a huge risk. I have been in the real estate business since 1993. In 2013 I decided I wanted to start my own brokerage. There were so many established brokerages in the Houston area so I had to figure out a way to be different than the rest. One day, I sat down and wrote a plan on a napkin. My plan was to offer full-service flat fee listings to sellers and rebated commissions to buyers. Read more>>

Michael May

I graduated with my doctoral degree from Vanderbilt University and began my academic career as an assistant professor in special education and behavior analysis at Southern Illinois University Carbondale in 2007. I met my wife during this time and we got married in 2011. I was granted tenure in 2013 and continued serving as an associate professor in special education and behavior analysis. Read more>>

Jan Daudi

A sad fact is life conditions us to please people. We are taught that putting people first, before our own needs, is the “right thing to do”. Don’t get me wrong, as a mother of five children; I understand well the responsibility and nobility in catering to dependents and that this may mean I experience a level of intentional sacrifice. However, many of us carry this mindset in a manner that is; Read more>>

Laura Woellner

I’ve wanted to start a business since I was in elementary school, but taking the leap was difficult. The comfort and stability of a full-time banking job was hard to leave, but I wasn’t happy. After giving birth to my first daughter, I didn’t want to leave her to go back to a job I didn’t love. My husband was a business owner so our income was unstable. Read more>>

Loren Howard

Entrepreneurs will tell you that the biggest risk they took was becoming an entrepreneur! For me, it was the next step after my football career ended, and I took the leap to start my first business. I had no idea what I was getting myself into and all the details involved, and while that first business never got off the ground, it was fundamental in teaching me everything about business and how to run a company. Read more>>

Rafael Larin

A saying has stuck with me over the years and that is the worst risk is not taking one. I’m a calculated risk taker for sure. I don’t just take any risks, especially ones that are purely thrill-seeking that can end in personal injury. But risks that can alter the course of your life are important to take. The first one I took was to join the military out of high school. Read more>>

Chaz Hodges

Your heart is beating fast as you gulp air. The world is fast and buzzing between your ears. Questions outweigh the answers, as you count the amount of odds that are stacked against you. One decision could change everything. You take a deep breath from the bottom of your gut. Intuition takes over and everything else dissipates. You surrender. Read more>>

Katie Croft

The biggest risk I’ve taken as a creative is when I left Texas for New York alone with two children. I was 38 and had two kids, a comfortable house, a close community and wonderful support system, but I had wanted to get my MFA for twelve years. I realized that I could wait until my children were grown and gone from home, or I could take them along for the adventure and show them what it was like to pursue your dreams. Read more>>

Junli Song

In many ways, becoming an artist is the greatest risk I’ve taken in life. Growing up, I never saw this as a feasible career choice. I was raised by immigrant parents who moved here hoping for a better life, and so something as unpractical as art was simply not an option. I grew up unthinkingly checking off the list of Chinese American stereotypes: straight-A student, good at math, took all the AP courses, played classical piano, always obedient, attended prestigious universities (and more importantly, studied respectable, employable disciplines). Read more>>

Brenda Umana

So there I was at 23 years old, working as an accountant in San Francisco, CA. Just a few years prior, I graduated with a Business Degree from UC Santa Cruz. At the time I thought everyone hated their jobs. It sounds trivial to me now but I didn’t realize that I had a choice. It seemed like you graduated college, get a job, wore office clothes and high heels, and spent time in a cubicle. Read more>>

Katie Mason

I’m a big dreamer (I’m talking night time dreams here). I moved to Denver, Colorado 24 years ago because of a dream. And I never looked back. My dreams guide so much of my personal, professional and creative life. I teach dreaming practices to clients as a licensed psychotherapist. I’ve developed my own relationship with dreaming as a guidance system for my health, my healing, my relationships. Read more>>