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.

Char Modelle

One of the greatest risks I have taken, was saying yes to clients before I felt prepared to coach, manage or consult them. I said yes, then figured it out. I didn’t always know about the client’s niche, but I knew what I brought to the table so I trusted I could add value to them. I have coached influencers, product developers, football analysts, performance coaches, real estate moguls, investors and more. It blows my mind to look back at some of the clients I have had. Read more>>

Zola Stone

My whole career and life has been about taking risks! The bigger the risk, the closer you are to success I like to think haha. When I graduated from high school, I knew I had to leave Minnesota if I wanted my dreams to come true, also to live a better life. I had only $500 in my pocket and I drove to Los Angeles by myself to find more opportunities and work in the entertainment/music industry. I experienced the Hollywood lifestyle to the fullest for 10 plus years. I went through it all, good and bad. This industry is tough but the number one rule is, NEVER GIVE UP… No matter what! Read more>>

Hannah Leboff

In 2020 the pandemic hit and, at that time, I was a full-time singer/songwriter. I had a real “aha” moment that I no longer wanted to be a part of the music industry, no matter how long I’d been trying. It was a lifelong dream, but I came to terms with the fact that I was no longer happy and it was time to make a big change. So I began teaching online zoom classes to friends who desperately wanted to move their bodies. Stuck in our tiny apartments, we all just wanted a release from the reality of the world around us. Read more>>

Yasmine Wahab

Thank you for having me.  The idea for The Seed came during a pivotal time in my life when I was closing many chapters and embarking on writing a whole new book. After mostly playing it safe all my life, I wanted to do something that would even surprise myself. Although I always wanted to start my own business, I didn’t know where to begin and what the business would be, but I was certain that whatever it would end up being, it would have to fill me up with joy. I’ve always had a love for hosting and entertaining, so I started to dabble in a food blog during Covid to sharpen my cooking and baking skills. It was an incredible feeling to see my recipes and dishes on people’s dinner tables and it sparked something in me. It set me on a path to follow that joy and see where it would lead me. Read more>>

Lori Mitchell

When I was just starting out in my illustration career I wasn’t sure what direction I wanted to go. In art school they were pushing airbrush and “movie posters style”. That wasn’t what I liked to do. I ended up putting together a portfolio of work that people liked, but it didn’t particularly suit me. What I really wanted to do was illustrate children’s books, drawing in line and then adding watercolor. I could picture the paintings but I did not have this style in my portfolio. I was inspired to write a children’s book about diversity and acceptance because of my daughters skin condition, vitiligo, where you lose the color in your pigment. Read more>>

Adam Chambers

Maintaining a life as an artist is a life of constantly taking a risk. It is not for everyone, but that is what makes it special. So much goes into the mental side of choosing this profession but some people don’t realize that you will always continue to have to choose it. So you are constantly taking a risk. I find that many people that are starting out are stuck on something. Bad relationship, past traumas, financial insecurity, lacking confidence, and the list goes on and on. But that is what people are leading with. And right behind that layer is the best thing about them, and what they are so good at, and what they really want. Ask yourself how would you best friend describe you ? It’s usually in those answers that the best thing about you is revealed. Start to lead with that. The risks won’t seem so scary and you will approach them all with a real sense of confidence.. Read more>>

AKIRA KOMATSU

Risk is a trigger to draw out your hidden or unexpected power and ability. You have to think out of the box to find the solution. It is mainly related to money, which means life itself. There’s no doubt you need money for food and rent first. Sometimes, you must throw your pride and ego away to go through the new door, and it’s mentally tough. Why do I have to do this? How can I do this? You may think, but you have no choice when facing the risk. You must find the unexpected ability inside of you and encounter some new possibility in front of you. That is the excellent enlightenment of life. I always take a bit risky way, not overwhelming, if it seems exciting and worth trying when I choose to take one out of some methods and enjoy struggling to find something new. Read more>>

Albert [Abdul-Barr] Wang

I am a conceptual artist based out of the Pasadena area and will be attending the MFA studio art program at ArtCenter College of Design this fall. I just moved last week from the Salt Lake City, Utah area to here and for me, this has been a huge transitional phase as I had to find an apartment within a few days and procure furniture, supplies, technical equipment, art studio materials, art and research books, and assets for everyday living. As I had few friends, mostly from CalArts and my new roommate, I found it challenging to shift to the Los Angeles lifestyle and pace abruptly. Read more>>

Tiffany Kuhwede

I fought so hard to gain my recovery and my health. I finally had a job I thought I was supposed to have for a long time. I had a steady paycheck, mediocre health insurance and retirement, and a few days off each year. I started hosting a group for teenagers struggling with suicide and then a few months later decided to quit my job and become a full-time coach. I just knew it was something I had to do even though it was taking a risk of going back to unstable work. Every week I become more stable and again have a steady paycheck, days off, and health insurance. This time I also have an amazing team of humans I work with, enough money to pay my bills and enjoy life, and a pathway to continuous growth. I am happier in my career than I have been ever before and I know the risk has paid off more than I ever imagined it would. Read more>>

Ivett Flores

The most significant risk I have ever taken as an entrepreneur developing projects as part of my architectural practice is studying for a Ph.D. in Germany in a parallel time framework. This conjuncture has become my life’s most challenging and rewarding experience, offering unique opportunities and considerations. I have always believed that science and business (or, in other words, theory and practice) are complementary concepts, especially in a field like architecture. Since I was preparing my application for the Ph.D. acceptance, I started my approach to Research Opportunities in the area I am passionate about, Energy and well-being in the built environment, which can lead to valuable contributions to the field and innovation potential. Read more>>

Alina Chau

I used to work full-time as an animator in the animation industry alongside many talented professionals. The job paid well; it was the career I had always hoped for as a film student. However, after several years passed, I began to feel like I was losing my artistic voice and vision. Although I enjoyed working on popular commercial titles, I missed the pure joy of creating art for myself. It was like a child’s joy when picking up a crayon and drawing without any pressure to be perfect or judged. Creating art at work became more of a chore, a responsibility, and a job. Even though I made art daily, I stopped growing as an artist. Read more>>

Sam Polesak

I’ve always been someone that is inherently aware that life is short, and in order to make the best of the time we have here on earth, I needed to take the best risks I could to help me grow. The same applies in business, you’ll never get to a point where you’re comfortable and the stars align. There is never a right time to start a business, for most it’s a long drawn out process full of lessons and growth. That gut feeling of terror and excitement when you’re going to jump into the water, is the exact feeling when you should jump forward with confidence in life, because, what’s the worst that could happen? Most things worth it in life are on the other side of fear. Read more>>

Josh McManus

I started playing in bands when I was just a kid, 13 years old. From the fabled no social media days to Myspace, then Facebook, Youtube, and Instagram, it’s been quite the ride. Finally, I stumbled into TikTok when I hit 30, and that’s when things really took off. Before the pandemic, I was part of this band in Omaha, and we were doing pretty well. We were close to selling out local shows, and our single after our first album racked up over a million streams. Then the shutdown hit, and everything fell apart. We all went our separate ways, and I lost all my freelance marketing clients. Read more>>

Ashley Barnett

I’ve always been creative and had an entrepreneurial spirit. Even when I was little, while other kids were playing house I was pretending to run a business. I started off slow, listing things on eBay when I was about 18 while working normal 9-5 jobs into my 20s. Then as things like Etsy, Facebook and Instagram developed I started to see how I could turn my passions into real businesses. I combined my love of antique and vintage with my desire to create art and found that they complimented each other well. I started to grow my Miss Holly Hock brand and following, focusing on curated vintage and assemblage art and it become a full time business. Read more>>

Mandy McGowan

I have historically been in the accounting and tax industry for the past almost 17 years at this point. This past spring, I took a huge leap of faith and fully closed down my accounting practice to step fully into supporting business owners in a different way with their finances. This was a risk because my accounting business was very successful and I knew I could earn enough in 4 months to support my family all year. But the level of work during those 4 months was no longer worth it. I wanted to prioritize my family and my health and to do that, I knew I had to let go of this safety net. Read more>>

Logan Evans

I feel like the biggest risk I’ve taken is being a self taught nail technician and being able to apprentice and work towards my license! It was such a big risk because I started in college right before COVID happened and I was already in school for Computer Science. I took a huge risk teaching myself and seeking out the opportunity to apprentice while in school virtually due to COVID and being self taught. There was a master cosmetologist my mom has been going to my whole life and she loved my work and didn’t mind taking a chance on me. From then on I realized it was one of the best things I could’ve done. Read more>>

Dr. KIMBERLY R. MAYES, LCSW

My biggest risk thus far is attaining my doctorate degree. Not because of the challenging nature of becoming of subject matter expert & embracing the title of doctor, but because I decided to study, research & develop an intervention that is not common within the mental health field, culturally responsive interventions. As a Black Caribbean mental health therapist, I recognized an abundance of clients reaching out to Essence Therapy & Wellness Center (my private practice), because they identified with me integrating holistic practices into our therapy sessions. Clients gave the feedback that most BIPOC clinicians aren’t offering this as an option. This was relevant to the clients, because talk therapy is not the only intervention the BIPOC community uses to find mental & spiritual peace. Read more>>

Angel Lunetta

The first risk I took, was at the age of 13 when I first starting running away. I don’t know what happen, I just woke up one day, stared at the Chicago skyline, and felt that there was something important waiting for me. Apart from being stuck within an unhealthy environment growing up, I felt like the outside world had something significant in store for me. Being raised and adopted into a conservative family, I frequently felt like I didn’t belong. I craved adventure and I wanted to live, fully and freely in a space where I could embrace being myself. I was always so curious about the world around me. I longed for discovery. Read more>>

Rachel Craig

When my daughter was born, in April 2022, I was working for a major insurance company as a ‘clinical nurse reviewer’. I hated the job, but it paid the bills. And allowed me to work from home. As my maternity leave came to an end….it was time to go back to this job. It crushed me, as it does with most parents, to have to split my time between my baby and my job. I would get up at 4am to get work done before my baby woke up. I never fully got to be present with her. Read more>>

Anne Stedman

I am so grateful that in my 40’s, I can look back on every exciting career turn I’ve experienced and know that I have no regrets. That is because I have always been willing to take risks. And by risks I mean, always saying yes even when I was scared of the unknown. Whatever has come my way, I have said yes (and I mean everything). Actor, producer, writer, influencer, shoe designer, improv, talk show host and stylist. Now all those careers may seem like they don’t coincide with one another, but when they came into my life throughout the years it actually did make sense. Read more>>

Takiya Saavedra

Last year I was offered the opportunity to make something completely outside of my comfort zone. I also thought it was outside of my creative ability. A client wanted an abstract 12′ wide x 10′ long fiber mural. I purchased hundreds of dollars in material, practiced lots of new knots and worked for weeks to make the largest, most intricate, macramé piece I’ve ever created. My client was thrilled and it looks beautiful hanging in her home. I’m really proud of conquering that project. Read more>>

Trecy Kent

I joined the USAF at 18. I was bored and not interested in attending college yet and needed to find a way to pay for it. In joining the United States Air Force I signed up for the GI Bill and had my ticket to be able to attend college when I chose to. I spent 13 years on active duty and earned my Bachelor’s Degree in Business Administration. After 3 tours in Saudi Arabia during and after Desert Storm I left the military to become a High School Social Studies/ Economics teacher. I earned my Masters in Education and Education Specialist degrees and rejoined the USAF as a reservist at Dobbins ARB in Marietta GA. I became an assistant Principal not long after and then Deployed to Joint Base Balad, Iraq in support of Operation New Dawn. Read more>>

Ryan Kimball

The biggest risk I have ever taken in my life is when I decided to leave my “career” as a preschool teacher and chase my dream to live full time on road out of my truck camper. I was finally using my college degree becoming a teacher. I truly believed that having a career was the answer. I was excited to tell people, I am a teacher. I very quickly realized that the 9-5 wasn’t the life for me. I loved my kids but I could feel that I was losing myself. I realized it was time to finally chase my long lasting dream of living full time on the road. Read more>>

Michael Sutton

I spent 43 years of my life in Detroit Michigan…..born and raised……in 2016 I took a leap of faith….hopped on a greyhound bus with $500….a backpack…..and a suitcase….headed for Houston Texas…..I only knew one person in Houston…….7 years later I can say this has been the best decision of my life…..inspiring myself to do better and treat myself better….make better decisions with my life because there was no way on earth I was moving back to Detroit! Read more>>

Charles-Henri Avelange

Deciding to go into an artist career is a pretty big risk in itself. But I think the biggest, and scariest risk I have ever taken, was to decide–in addition of becoming a film composer, that I was going to do it in the United States, very far away from my native French Riviera in the south of France. When an opportunity came to me to leave France and go to the US, I jumped on it without hesitation. Even though nothing was really waiting for me here. I was barely speaking english and I had $500 in my pocket. I purchased non-refundable airfares to make sure that no one could talk me out of it. I quit my job in Paris as soon as I saw the opportunity and never looked back. Read more>>

Chase Martinez

There’s been many times in my life where I’ve taken risks and made decisions that frightened me but nothing beats the feeling of betting on yourself, trusting in what God can do and putting in the work only to see the results for yourself. The fear attempted to paralyze me but in the end it empowered me. Here are some of my life changing decisions that led me here. One of my earliest memories taking one of the biggest risks of my life was probably when I was in the UK. I just turned 17 and I remember coming downstairs one day and I told my parents “I decided I’m gonna be a singer and I want to move to London to pursue my dream” I remember feeling very confident when I said it but my idea was immediately shut down. There was no way my parents would let me leave my home at a young age let alone attempt to chase a delusional dream. Read more>>

Dee Dee Stephens

I am taking 5 years to separate my art from income. I consider this a risk because I am no longer actively auditioning so there’s a chance that my industry contacts will dry up. You might be wondering why I would do such a thing. Well let me tell you why. Covid scared the crap out of me! In February 2020, I moved in with a man I was dating at the time. Things were serious in our relationship and we were talking about getting married. When the pandemic hit, we put together a financial plan for me to start teaching while being an artist. He was in a financial position to cover the rent and household bills. But that got me to thinking,,, what if the pandemic hit at a time when I was on my own? Read more>>

Olga Avezbakiev

It all began during the tumultuous times of the pandemic when uncertainty seemed to grip the world. It was in the midst of this chaos that I found the courage to take a leap that would eventually redefine my success and personal fulfillment. The turning point came when I decided to step outside my comfort zone and start growing my social media accounts. It wasn’t an easy decision. But something inside me shifted, and I realized it was time to break free. Read more>>

Calen Otto

One of the biggest risks that I’ve taken was deciding to ride a pedal bike across the country at just 19 years old on my own as a female traveler. I started the journey with just a. $300 Visa gift card, hoping that I could do work exchanges, random jobs, and find free places to stay along the way. To my surprise, I was able to do just that! Although it was a safety risk and a challenge, I learned so much on my bike trip from VA to CA. It taught me that I can travel on an extremely small budget, something that I write and share about often today. While I wasn’t thinking about my own future successes during this trip, the experience itself inspired me to publish my own budget travel guide to the USA, has allowed me to get speaking gigs, and reminds me just how powerful I am on a daily basis. Read more>>

Diona Devincenzi

The first big career risk I took was back in the mid 90’s when I decided to go “all in” and move from the Bay Area to Nashville to be in the “center” of what is the songwriting industry. This was the best way to learn and up level my songwriting craft, in addition to being around other talented and aspiring writers, musicians and producers . I figured something might rub off on me. It was a scary decision and it was hard for me to adjust, as all of my family and friends were thousands of miles away. But It was a great place to learn the craft of songwriting and the wealth of talent there was ridiculously high. Read more>>

Carissa Rolle

The biggest risk that I have taken is leaving my full-time teaching job with benefits and income security to run my business full-time. I did this all while pregnant with my daughter. When I was 3 months pregnant with my daughter I decided that it was time for me to run my teaching/tutoring business full-time. At this time COVID was running rampant and many people wanted more in-home/virtual teachers rather than physical teachers. I knew that covid wouldn’t last forever but I felt it was a great time to step out on faith. This was the best decision I could have made for me and my family. I am still running my business now and it is growing. Read more>>

Paisley Bird

Any creative endeavor is a risk. Creativity is your vulnerability expressed and it can be frightening to share it. I face this fear every day in every medium I work in. My biggest risk I’m taking is sharing my deep thoughts with the world as an Insight Coach and writer. I am an insatiable learner; I’m addicted to knowledge. However, compiling all the information in my head into a digestible form for my audience as an Insight Coach is a daring feat. I expose my innermost opinions and wisdom. It’s been a wonderful lesson in authenticity, being okay with whatever consequence comes from publishing sensitive topics. Read more>>

Betsabe Roman

I was a professor for 10+ years. I went and did my phD and a postdoc. But the biggest risk I took was to leave my lifelong profession and go back to school to start a new career and my now bridal business. Sitting in a chair listening to someone else teach a class was hard, I hadn’t been in that chair for so long! I remember the fear and the anxiety I had. I didn’t want anyone to know that I was doing this, I kept thinking that people would judge me for leaving a very promising career for a “hobbie”. However, for the first time in my life I also felt fulfilled! I had always loved art, ever since I can remember, it was always my first love. Read more>>

Dwight Hwang

I used to work as a storyboard artist for movies, animation, and games for 20+ years. It was what defined me and it was my identity. As exciting as it was, I eventually got burned out. My wife and I had our son and yet I rarely got to see him. I pretty much missed out on the first two years of his life. When I would hold him, he would push me away as he did not know me. I knew that I needed a change. During my seven years working in Tokyo anime studios and movie sets, I picked up a hobby called Gyotaku, which is basically their version of taxidermy. Instead of stuffing a fish and hanging it on the wall, they would print the fish with calligraphy ink and rub a sheet of paper to create a fossil-like image. Read more>>

Shina Reynolds

The greatest risk I’ve taken in my career so far was deciding to publish my first book independently. When I finished writing what would become A Light in the Sky, I queried agents. I planned to test the waters and hopefully find a good fit with an eager agent, and then they’d help me find a great traditional publishing company. I also knew I could, if I decided to, publish independently, either under my author name, or by starting a publishing company. Read more>>

Angela Hansen

My initial decision to learn the art of Pinstriping was a huge risk, especially since it was something I had never attempted before. Also, being a woman in an industry with mostly men was very intimidating. But the driving force for me was when one of my professors in college literally laughed at me when I told him I wanted to learn Pinstriping. It was the right amount of motivation that I needed to prove to him, and everyone else that doubted me, that my goal was achievable. Read more>>

Samantha Wood

When I first commissioned into the US Army as a 2nd Lieutenant on active duty in 2008, a welcome reception was held at Fort Sam Houston, TX. Among many speakers was a medical officer, at the rank of Colonel, who spoke to the young officers quite candidly. I had no context for his words at the time, but he said something like this. “In your career as Army officers you will be told what path to take; there is a timeline for various positions and commands, a career path so to speak. You will be told that you must follow this path in order to be successful. Read more>>

Sppike Mike Muellenberg

When this idea came to me it was all about “am I ready to commit completely to this art.” 7 years later I’d have to say the apparent answer is yes. Risk? I mean we’re talking about a band made up of middle aged men with dad bods playing Spice Girls songs Sex Pistols style in DRAG. So Risk? Really? HAHAHAHHA Yeah. There’s been plenty of that. Like the time we took a risk to submit to America’s Got Talent. That was a risk. I sent a fan phone video of the band with the application and was contacted in a couple days. Telling us to show up at open auditions in Pasadena. We were escorted past the walk ons directly to the basement to perform for 8 of the producers sitting behind laptops. Read more>>

Abimael Acosta

When I was 45 years old and already had a well-established career as a writer and director in Puerto Rico, I decided to pursue a dream I had since childhood – which was to move to Los Angeles and start working in the film and TV industry there. Despite many people telling me not to do it and that the risk was too great, I chose to follow what my heart was telling me. Within a year, I organized my move from Puerto Rico to Los Angeles. Read more>>

Blanca Amaya

Deciding to leave my 9 to 5 corporate and secure job and take the risk of starting my own practice that had no guarantee to have success was extremely scary. I grew up in a household where it was encouraged and promoted to obtain secure employment, stay in a job for 30 years, and collect a pension. That was my origin plan and I worked hard to get that but I found myself unhappy, unfilled, getting burnt out, and wanting more. After having my baby, having different priorities, talking to friends that had made the leap into private practice, I decided to take the risk. I decided to bet on myself and I have been winning ever since. Oftentimes I think to myself, why didn’t I do this sooner! Why did I let fear and self doubt get in the way! Read more>>

Brent Stubblefield

Turning a creative hobby into a business is always risky. It’s especially crazy to do when you are the sole provider for a family of five and that hobby is hand crafted knives. Several years ago I made the decision to shut down my residential renovation business to pursue knifemaking full time. The truth is that I never was very good at making money in the remodeling business so it actually made sense to fall back on my hobby. This is the opposite of the traditional “don’t quit your day job” wisdom but for me in was the right thing to do. Read more>>

Adele Etheridge Woodson

The biggest risk I’ve taken (besides committing to working full-time as a musician!) was moving to London earlier this year. I spent months preparing my visa application, gathering evidence to prove to a whole government (!) that I am a working artist. After a few months of preparing and a few weeks of anxiously checking my email, I was approved to stay in the UK for five years! Moving was a whirlwind, and it was more of a learning curve than I anticipated. But after seven months here so far, I can say it was the best decision I ever made. I live in a city full of amazingly creative people from all over the world, and I feel lucky to be surrounded by talented composers and filmmakers! Read more>>

Brianne Atkinson

A great risk that one can take is to move out of your comfort zone.. At one point in time in my career, I had outgrown my environment. I took a risk by moving from my hometown to a totally new environment in a different state. My hometown whom I loved dearly, had become too comfortable and stagnant and I needed to scale my business in a more creative way. And, as a domestic abuse survivor, I needed to breathe new air. The move was exciting and scary all at the same time and I knew that building a clientele was most important in order for me to be able to build a business from scratch. Social media played an intricate part in that strategy. Read more>>

Carlos Zatch

Take risks… It’s a great phrase that carries a lot of responsibility. I’m a person who likes to jump in and act quickly when it comes to creative projects. When I have an idea, I look for a way to achieve it, making all possible efforts and using the resources I have at that time. I think that one of the best decisions I have made has been to take the risk of dedicating myself to content creation and running a business out of it since in my environment it has been seen as something not very common and that it entails many risks since that, not everything is safe. Read more>>

Tina Naidu

In 2020, I felt a slight burn out in the healthcare field. I had always been a fitness enthusiast and due to my own struggles of being overweight and having an unhealthy relationship with, fueled me to find more answers and educate myself. I signed up for a fitness and nutrition coaching certification with no real plan in place other than educating myself. I shared a lot about this journey on my Social Media Page and connected with several like minded people in this industry. The more I spoke to them, the more I realized I may want to do something in the fitness industry in whatever small way possible. I connected with the founder and CEO of a virtual fitness and nutrition coaching company called The Boss Body Revolution that focused on south asian nutrition and limitations. Read more>>

Evan Rosenblatt

At 25, I had my master’s degree and had been steadily teaching and dancing professionally while staging my own creative work. It seemed like life was good, but deep down there was a sense of dissatisfaction. While dancing in a company, I was experiencing debilitating hip and back pain. With an advanced degree in kinesiology, too many certifications to name, years working in a PT clinic, and lots of medical resources, it didn’t seem logical that the pain remained a mystery. As conventional practices failed one by one, I was losing hope. Enter the first risk in the shape of a choice – to continue forcing the path I clung to, dancing through the warning signs of increasing pain or question the very path itself. After a lot of anguish, I set foot to the latter. Read more>>