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.

Julia Germeroth

“The greater the risk, the greater the reward”. I read that from a fortune cookie once, but I’m almost positive someone wiser and more famous said it first. Pursuing art is a risk within itself, and taking risks within your art pushes you to become the artist you strive to be. Some of the riskiest choices I’ve made as an artist opened doors both professionally and personally for me. As a comedian, it was a risk to step on stage performing stand up for the first time. Did I bomb? No. Did I kill it? No. But the fear of the unknown was gone. Because now I knew. And when you know better, you do better. The confidence of taking a risk gave me confidence within myself, within my art. This led me to taking bigger chances with jokes, riskier topics to tackle. Or with directing, such as “Monster In the Closet” . Read more>>

Marcela Isaza

After 20 years as one of the top entertainment journalists in Los Angeles, I decided to pivot and completely change careers. I wanted to be of service to others and knew one day I’d use my first passion to do so: fitness. So I went “back to school” so to speak and got certified as a personal trainer and group fitness instructor. I work 1:1 with clients, helping them get stronger, by teaching people how to gain confidence through movement. I also teach a really fun high-intensity spin class twice a week at a local independently-owned gym in Los Angeles called Everybody. I love it! I am so happy! Read more>>

Tyler Farnham

In 2009 I was a lifeguard Captain EMT in my hometown of Cocoa Beach Florida with plans to go to Fire school when the unthinkable happened. On a routine skydive with my mom performing her first ever jump, I suffered a near death accident. What resulted was two broken femurs with a near amputation of my right leg, multiple bone breaks in the right arm, shattered jaw, nine broken teeth and a fractured skull. Confined to a wheelchair and mouth wired shut I had strenuous rehab looming ahead along with a future dependency of Oxycontin in the midst of the Opioid epidemic. Read more>>

Blaine Schultz

Every day, we are faced with choices that can define our character and impact the lives of others. Among these choices, taking a risk to help someone in need stands out as a profound and selfless act of kindness. Such acts of compassion often require us to step out of our comfort zones and overcome our fears. In this article, we will explore the significance of taking a risk to help someone and how it can lead to meaningful and positive change, both for the individuals involved and for society as a whole. The Courage to Act: Taking a risk to help someone demands a certain level of courage. It means pushing beyond our own insecurities, doubts, and fears to extend a helping hand. Read more>>

Claire Bechard

The goal is to take a risk. The goal is to be brave and step through the unknown, taking challenges in stride and staying consistent in practice. Creativity thrives on risk and the ability to trust your gut and fellow creatives when taking the risk. I’ve been in many rehearsals where options are questioned and eyebrows are raised, but having a strong vision and a sense of group cohesion can pull most anything off. We were creating a piece in 2022 that utilized projections, sheets, and ladders and I really appreciated the way the team stood behind our ideas and we presented a fully conceived work. It could have been a hot mess but it ended up being better than my dreams. Read more>>

Donald Kimbler Olson

Risk is such a personal thing – whether big or small, it’s certainly not a one-size-fits-all.   I sometimes think when people tell you it’s OK to take a risk, I think that it’s probably  gonna happen once or twice in a life time,.. What is your biggest risk…?   You know, taking a risk wasn’t my problem- I was charmed, you could say—Risk  seemed to find me—I found 4 ways to knock around my teeth, and I lost an eye from a  childhood kerfuffle. And It didn’t really avoid me as I grew older.  Read more>>

Thunderstorm Artis

I was 18 when I decided that Music was going to be my career path, definitely wasn’t easy at first at all lol I remember playing 4-8 hour gigs at hotel’s for just a couple hundred bucks and busking on the street for whoever would stop to listen. Being an artist in general is definitely risk but the reward is definitely worth it in my book, Read more>>

Cal Barnes

I’m a risk taker by nature, but I’d put myself in a category called “The overthinking risk taker”. I’ve never been one to throw myself off a cliff without thinking, but after mulling it over for a while and waging war with my fear, I’ll usually find the balls to jump. I have to win the battle with fear and take the risk so I can sleep at night. If I was a straight risk taker with no thought involved, I’d probably be a professional skateboarder or sky diver, not an actor. Read more>>

Morgan Berry

I wouldn’t be where I am today if it wasn’t for me taking a risk. I got into the voice acting industry by competing in a voice-over contest at an anime convention. I almost backed out of the competition because I was so scared of putting myself out there and possibly making a fool of myself, but I’m glad I pushed through that fear and made the decision to try it anyway. I stepped into the opportunity with the thought of “if this is what the Lord wants for me, then I will win this competition. If not, then I guess I’ll just explore a different creative avenue.” I remember stepping up in front of the crowd holding the script in front of me. Read more>>

Madilynn Beck

Health and wellness aren’t “new” but in 2019 it felt that way. The start of the pandemic catapulted the world into a mainstream acceptance of wellness methods that it didn’t have prior. Massages in your backyard, yoga en masse at a park and virtual therapy, all became norms for the years that followed. Read more>>

Cornelia Gyura

I am a former IFBB (Body Building) German- European- and World Champion from 1986. I always represented the female side of Body Building. Yes, in the 80s there were a couple of female looking body building girls. I was able to get big sponsors like Nike International, Multi Power ( Weider Europe) Nutrition, Galaxy high end fitness equipment. I was in every health and fitness magazine issue, on all the covers, inside as poster and I was one of the first Germans having a one whole page in the US Flex Magazine. Read more>>

Lindsey Roach

I worked in the social work and insurance industry for 15 years prior to getting into the spiritual & holistic wellness arena. In 2020 I was fully burnt out and completely dissatisfied with my career path, longing for something I could do to help others in a deeper and more meaningful way. I dove into sound healing training in summer of 2020 and reiki training in early 2021 and noticed my whole outlook and life was shifting and expanding. After having to take medical leave in 2021 due to work stress at my day job, I decided enough was enough. Read more>>

Bee Thomas

I have a natural inclination for taking risks, which, to me, means questioning societal norms. For instance, starting a business might not be considered “normal” by some, yet countless entrepreneurs globally have embarked on this journey. In my case, I founded my own company back in 2007. Entrepreneurship itself is a prime example of risk-taking since both success and failure are possibilities. It requires a deep well of intrinsic motivation to persevere through the toughest moments. Taking a risk in the business world involves stepping into the uncomfortable, such as the year I invested $25,000 in business mentorship alone. Read more>>

Marty Smith

I was always told I had a good voice. People would tell me, “You need to be on the radio”. I thought, “Why not” and starting applying to radio stations all over Kansas City, where I lived at the time. After three years of being told no, I wound up at a radio station just north of Kansas City, MO. I walked in and asked them if they were hiring. The Program Director was there and asked if I had any radio experience. I told him I had no formal training. He told me they weren’t hiring and escorted me to the door. I went back in and filled out an application then went home. Read more>>

Darci Roberts

Being an entrepreneur or business owner takes a huge risk. You have to trust in yourself like you have never before you have to give into the idea that patients equals perfection. I worked 10+ years as a security supervisor. It was great fun way to pay the bills, but definitely not nothing that my heart was set on nothing that I wanted to see myself doing long-term. After getting a concrete idea of what I wanted to do with myself, and with the support of my husband, who I owe all my success to I was able to make my dream a reality. After realizing security was not in my heart, the job became more miserable. I left security and pursued my passion for permanent make up and eyelash services. I took the risk and quit. Read more>>

Brent Fannin

While living in Florida for the past ten years or so, I’ve been an animal trainer, zookeeper, and environmental educator in most major theme parks in the South. Working with so many different people and different types of animals was incredibly rewarding and I consider myself lucky to have done it. But issues with chronic pain eventually removed my ability to work with animals. Around that time, I met the most incredible person. She was there for me through some of the worst times of my life, and when the time came for her to accept a new career opportunity and move to Atlanta, she invited me to come with her. Read more>>

Dennis Lichtman

After graduating from conservatory with a music degree, I found myself in dire need of a job. I had very few gigs performing, and it turns out they don’t just give out “music jobs” to anyone with a degree! After applying for every type of job imaginable, I found myself working as an entry-level assistant for a small law firm in my hometown near Boston. My bosses were very kind, the work was easy, and I was good at it. It was supposed to be a one-year position, but as the year came to an end the partners offered me a big raise and a promotion – a golden ticket to an easy life. Read more>>

Sherri Rose-Holmes

Each year we decide to push events here in Savannah, is a risk all on its on! Savannah is a hard market!! Even well known artist have been known to cancel shows due to low ticket sales. Our event Rock-Ur-Natural hair health & Beauty expo has been going on for 5 years. Still the 150 to 200 that attend is low compared to the number of years this event has been going on. Places around us for example Jacksonville and Atlanta. Have a number of events year round with a good amount of participation from the community. Our event Street Food & Poetry Festival had its 2nd year this past September. Read more>>

Tyler Pennington

I believe that risks are necessary in anything that we do in this life. Risk taking has played a major role in my business. The biggest risk to date I have taken in my career is making the decision to become a full-time entrepreneur. The risk was very calculated and planned and has made me confident that not all risks are bad. Entrepreneurship is the career path of risks. Read more>>

Ramon Navos-Moral

I often share that I work to feed my tummy, engage in boxing to sharpen my skills, and create music to feed my soul. Over my 18 years in California, I explored various industries, seeking my purpose and a niche for personal growth. This journey led me to the video game industry, where I worked at Hyperkin, developing licensed accessories for Microsoft, HTC Vive, and Oculus Rift. Read more>>

Lasaunia Thompson

In February 2023, I took a leap of faith and decided to participate in Speaker Slam, the largest speech competition in North America. Prior to this, I had never spoken publicly, but I was determined to share my story. At that time, the competition’s theme was “Body Beautiful.” Read more>>

International Kool

Wow ! So , I’m zooming through a packed airport in the Windy City of Chicago ! I noticed a woman wearing a very innovative backpack for her travel accessory! I spoke with her briefly and complimented on how sleek and lightweight her backpack looked ! We parted ways before I headed to my connecting flight to San Fransisco (SFO) for a recording session in Oakland ! Wildy enough , after boarding my plane the exact same woman was sitting next to me with her BallnAudio®️ backpack ! Read more>>

Lola Dada-Olley

In 2020, my family launched the “Not Your Mama’s Autism Podcast” in the midst of the pandemic. Some well-meaning people in my life warned me against doing so over concerns that I would be discussing personal topics not typically shared in my culture relating to disability, neurodivergence, health care access and cultural stigma. In the end, after speaking to my husband, I realized that it was time for our advocacy journey to be more public and that public advocacy needed to be done in storytelling form. The hope is that our podcast, part memoir/part interview style podcast would help some people see that they were not alone and to have our children be able to better understand their journey when they come of age. Read more>>

RM47

Being an artist requires embracing risk. It’s a beautiful and fulfilling journey that demands trust in yourself and your talents to pursue your dreams. However, it’s a double edge sword where rejection, instability, and uncertainty can also play a part. It’s those challenges that taught us resilience and learning to navigate through it all. We’ve had to build thick skin along the way to keep pushing forward. Outside of creativity, some of our biggest risk taking comes through investing time (often away from our loved ones), and investing finances as entrepreneurs to sustain our art / business. Read more>>

Lala Loves

I had spent almost a decade of my life slaving away in corporate America, working for some of the top companies in the fashion industry. Yet, after hitting my seventh or eighth year in Corporate America, I remember my favorite times of my job were the end of the day when I got to go home and the days when I didn’t have to be at work. I was in my late twenties and realized while I loved my career in digital marketing and merchandising, I needed a change because I was burned out. So, I decided to go back to school in 2021 to get a Masters in Business Administration and stay in marketing and the digital space but broaden my horizon and work within a different industry, whether it be health or tech. Read more>>

“Risk” has always been a close companion in my art and life. I grew up in a place that normalized things like cliff-jumping, skiing, dirt biking, trail running, among other activities, and seeking adventure was an imperative. The freedom I had to explore was constrained mostly by the potential for physical harm. I wouldn’t describe myself as an extremist; for example, before diving head-first off a three-story cliff, I had a respectable amount of practice jumping feet first. Fast forward to today, and my favorite recreational activities are ice climbing and backcountry skiing, which are not particularly risk-averse sports but can be done in a reasonably safe manner. Read more>>

Cortney Jones

When I first started investing in real estate I was just 19. I didn’t know what I didn’t know and maybe that was the secret sauce. I just learned and took action; learned something else and took action; and so on. I didn’t question those that had come before me. My belief has always been that if someone else can do it then I can too, so as I would read a book about something someone did to buy an investment property with no money down, I implemented what I learned day in and day out and just kept going until I made it work. Read more>>

Joseph Orlov

This year I took a huge risk when I decided to become music partners with one of my best friends Matt Barri. We knew this was a risk for the obvious reasons like what if we fail and waste our time etc. Yet, the largest risk was our relationship. We wanted and still want to keep our personal relationship at its best. That’s why for every studio session or meeting we have, we also just hang out together, watch stupid youtube videos and catch up. It was a decision that I think we’re both very thankful for. We keep each other on our toes and working and it’s been a delight working with him on art. Read more>>

Sukey Molloy

It took a lot of courage and faith in myself to embark on a musical performing arts career. The teaching came more naturally and developed on its own, but bringing my own choreography, voice, lyrics, and melodies created a tremendous personal and financial risk. Without my teaching, and my husband’s help, along with my gifted co-producer, Larry Alexander, I wouldn’t have been able to sustain it. I was older, with children still at home, and wasn’t sure I could capture and keep the interest of a much younger parenting generation as well as survive the digital listening and viewing changes that took over the market. Read more>>

Josh Almeida

Just the act of starting your own business is risky enough! I’m convinced that there is little differences between playing black jack in Vegas and running a biz. You never get all the answers, you’re making the best call you can in the moment and hoping for the best. The name the game is lower the risk as much as possible while not holding yourself back. Read more>>

Ursula de La Sotta

I started creating Cuentologia, my first ever self founded company, when I was starting my family. I was 30 and recently married. We had just made the decision of moving to the United States so my husbando can study his master´s degree on a school he wanted in Chicago. I couldnt land the job I wanted in the US, so we didnt have financial security. But we trusted each other´s capacities and drive. So when I saw the huge need of resources to help parents deal with so many new challenges nowadays, I took a risk. A huge one… Creating a business and a family at the same time, with no guarantee nor salary. Read more>>

Beata Jutila

Talking about taking risks is something I genuinely enjoy because I believe that stepping out of your comfort zone is when life’s most amazing experiences happen. I’ve always been someone who enjoys taking risks, and I’ve been fortunate to have the support of my family in trying new things. In the beginning, my risks were relatively small, like picking up random hobbies. Read more>>

Janyre Tromp

I’ve worked in the publishing industry for more than 25 years. Part of that time I worked in marketing, part of that time in editorial, and ALL of that time, I worked for a traditional publisher. I’ve lost track of how many books I’ve acquired and edited. I’ve even lost track of how many went on to win awards and become bestselling titles. Read more>>

Azure Davis

Let me take you on a journey back to when I was 23 years old. I had a well-paying job in the supply chain department of a large medical corporation. It provided stability, great benefits, and a sense of security. On top of that, I was in the final stages of completing my bachelor’s degree in business management. Life seemed pretty sorted out, but there was something more that tugged at my heart. Read more>>