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.

Erica Mather

In 2008, things changed in New York City, people had less cash on hand, and I lost many of my private clients. I was new to my business, and felt certain that there MUST be a way to make the numbers work out. So, despite being on my back foot and also having less cash on hand than I felt comfortable with, I invested in a business coach. Read more>>

Brittany McCarthy

Find a career in fundraising was the best decision I have ever made for myself. A career in fundraising and development offers a unique and fulfilling opportunity to make a positive impact on the world while also advancing your professional growth. Fundraising professionals play a pivotal role in securing financial resources for non-profit organizations, universities, hospitals, and various causes. Read more>>

Kimberly Marsh

I believe my entire life has a pretty common theme of taking risks. I left home at a very young age and took the risk of raising myself and surviving on my own. I became a young teenage mom and had to take the risk of figuring out how to not only support myself but also taking care of a baby.  Read more>>

Marilee Clark

Annie Claire Hudson

During the shutdown in 2021, I was working as a video editor. Editing and design had been my career since college. I spent each day at my desk, and I wasn’t happy. I realized that my desk job was the source of not only my depression but also physical aches and pains. I felt like I was wasting my life sitting at a desk all day. And then it hit me, I needed to make a big career change. Read more>>

Jennifer Byrne

Starting a Travel Agency from nothing more than a love of travel and a dream wasn’t something that should have worked out logically. I had a few years experience as a Travel Agent, but I had such a passion for the business, that I just always knew there was no other way. As a child, we would invite neighborhood kids in to play travel agency with our globe and phone books. Read more>>

Ozan Karakoc

‘Risk’ is a powerful word. It’s intense and intimidating. It embodies both the potential for failure and the promise of reward. Therefore, almost all risk-related stories are like a thrill ride, even for the readers. Read more>>

Sal Cerda

I just had a conversation about this with my wife last week. Our son who is now 3 years old was telling my wife Frida to be brave while she was practicing roller blading. Frida fell a few times and our son Sebastian said, ” don’t be scared Momma, be brave, you can do it”. I know, it made our hearts warm and fuzzy too. Frida then said, ” it’s ok to be scared, it does not mean you are not brave”. Read more>>

Kelli Binnings

In 2015, I started a full-service creative agency with 2 other partners. We started with just 4 clients working out of my living room and over the next 6 months, moved into a swanky little office on Magazine Street in New Orleans. In just under 2 years, we grew to 5 team members and some 20+ clients. We were competing with some of the best agencies around and winning. Read more>>

Nellie Svensson

I believe risk taking is one of the most common things an actor has to deal with on a daily basis. It takes a lot of strength and some balls to be willing to even do it in the first place, but once you’ve got the boll rolling it becomes second nature. Read more>>

Kenisha Coon

I took a risk by publicly writing a book about my estranged family and overcoming generational trauma. ‘And Then She Persisted’ is a powerful story of resilience against abuse, neglect, and racism. It began as a collection of blog journals, influenced by schooling, therapy, and deep conversations with friends. It’s a journey of channeling spirituality and confronting childhood trauma, which unknowingly conditioned me to persist. Read more>>

JoAnna DeLuna

The risk I took in the photography world was being a modeling photographer that primarily loved capturing beautiful gowns. Read more>>

David Quintero

About 7 years ago in 2016 I was fired as a manager from Pasco Kitchen and lounge by Ramiro Scavo(the owner). I had worked a year for him at his restaurant and quickly became manager and was responsible for all the day to day reports and shift managing. I was promised a raise and never got it. Then one day I asked him for the money i was owed and he fired me 2 days later. Read more>>

Dhwani Shah

I moved to New York City in December 2021 to pursue a career in acting in the United States of America. The risk with this? I left a blooming career in Mumbai as an actor pursued by both theatre and TV producers alike. I could have stayed and did what my other actor friends were doing, but I wanted to experience world cinema and boy that was a great risk! Read more>>

Equalla Foster

Life is full of risk-taking. Risks were there from the moment a person could start making their own decisions. Risks involve uncertainty and the possibility of success or failure, defeat, or danger. I fully know the courage, strength, wi sdom, and perseverance levels needed to take such leaps of faith, small or big. Read more>>

Billie “Bowtie” King

In the world of business, taking risks can be a daunting endeavor. For Bowtie, the owner of a cigar brand, the decision to step outside the conventional advertising box was a gamble that could have easily gone awry. In 2009, he made a bold choice to infuse a high fashion aesthetic into his brand’s imagery, a stark departure from the typical cigar brand advertisements that all seemed to blend together. Read more>>

Autumn Shelton

After returning from a 16 month honeymoon, I was in search of a commercial real estate job, but ended up deciding to take a finance position with a Dutch cut flower grower that had just gone through bankruptcy instead. I diligently worked toward getting his company back in the black, which we did. Read more>>

Daryl Bouchard

The biggest risk I have ever taken was to leave the Canadian Armed Forces, after 9 years of service, to start my own Nutrition Practice. The military takes care of everything for you, your pension, your paycheck is steady, every two weeks you know exactly how much you are going to make, dental, medical, everything is covered. Read more>>

Colin Vanatta

Home State Brewing Co. is our team’s execution of a dream I had in 2017. I never planned on being an entrepreneur, or a business owner. I planned on working as an engineer like my Dad, and working at Lockheed Martin like my Mom, Dad, my aunts, uncles and grandparents did. Read more>>

Liz Vaughn

In 2007 I was looking for additional ways to broaden my exposure in the art market. My original oil paintings were being collected, and I felt a greater sense of confidence about presenting and selling my work. The caveat, of course, is that as an artist you can only create so many original pieces. My thought was that printed versions of my work would expand the audience, but it had to be something more than the standard giclee print. I wanted a fresh idea. Read more>>

Va’rai Unique

I’ve taken quite a few risks in my life, as I love the exhilaration. I think one of the most significant risks that I have ever taken, was moving to a different country than the one I was born and raised in. What made me move from London in the United Kingdom to the United States of America? Read more>>

Adam Taylor

Sara Siegel

My entire Los Angeles career in Fashion started with taking a risk. I moved from my hometown in Michigan to California with $10k (that I saved up working as a waitress three months before) and a deep gut knowing that I would get a job if I take the risk and move across the country. Read more>>

Rebeka Davila

I love this question because despite attempting to NEVER make a mistake as a kid, risk has been a theme in my life. Read more>>

Christine Blackburn

After college I became a flight attendant for USAir. I flew for over seven years and traveled around the world with the airline and also in my free time. It was a wonderful job to have in my 20s. But as you know the first day on the job as a flight attendant is the same thing you’re going to do on the 10th day of the job and the 30th day, after five years and after 10 years. Read more>>

Justin Trabue

In 2013 I graduated high school in Washington DC and moved across the country to study wine business at Cal Poly San Luis Obispo. During my first quarter at school I decided on their business program, they asked us all, “if you could do anything in wine what would it be?” I told myself I would one day open a boutique winery specializing in lesser discussed varietals. Read more>>

Melissa Phillips

We took a big risk and invested back into the business a lot this year. Having two small children and at our ages it has been a lot. We hope the risk pays off which we know it will with our attendance last year and what our guests have asked for over the years. We finally took the leap and did what was asked to make sure everyone enjoys the farm as we have for so many years. Read more>>

Mark Englebrecht

I have taken many risks in my life since I was 17 years old, the first risk was when I joined the Navy as it was a big step in my life and then 10 years later would turn around and make a career change switching to the Army. Being in the military especially when you have a family can be very hard because they have to adjust to your lifestyle and make a huge number of sacrifices in there life consistantly ( any military brat can testify to this lifestyle) making friends at a new duty station, or even when the service member is deployed in many cases that was my lifestyle. Read more>>

Chivaria Cooper

I took a risk when I stopped procrastinating and started my YouTube channel in 2020. I started with what I already had which included my iPhone, tripod, ring light and microphone. Getting where I am today took patience, consistency, dedication, focus and always believing in myself. Read more>>

Jake Faun

Around 7-8 years ago, I decided I wanted to explore Los Angeles to see if it were somewhere I could live/work as a musician. I’m from the UK originally, all my friends and family are back home, so coming out here has been a big risk. I didn’t have a solid plan, didn’t even know if things would work out, in fact had I known what was required to get here, who knows whether I would have gone through with it all. Read more>> 

Lauren Kurtz

I had 2 big risks. My largest risk I think was taking a chance on myself. Making a plan and hoping for best to Juno into the unknown and work for myself. 8 years later I’m still here. Has it been a bumpy road? Yes! But with that I’ve been rewarded by making so many amazing connections and being able to do what I love everyday. My 2nd risk was to finally have my own booth at Dapper Day. I was so scared but now it’s one of my busiest events twice a year. Read more>>

Jay Parikh

The biggest risk I have ever taking in my life was following my passion in an industry where the odds of success are very low. To do this, I gave up the typical , everyday life. I started my filmmaking journey while I was still studying engineering and eventually I left my engineering career behind to fully chase my filmmaking dreams. Along the way, I had to work many odd jobs and had very little time for my personal life. Read more>>

Neil Aaron

I love risk!! Risk is the key to sparking a manifestation of an upgrade and better life. When we risk, we take a step beyond what we think is our maximum and it catches the universal energy’s attention. Whether the risk results in what we would consider a fail or a win, it does not matter. A risk moves the needle forward and opens doors. The biggest risk I took was going to Bali to learn this modality. Read more>>

Kate Eliza

I think anytime an artist shows their art, it can feel risky. Will it be perceived the way it was intended? Will people like it? Will it sell? I have taken a break from showing my paintings for the past few years while I have built up my other business; making handmade art supplies for other artists. That felt a bit safer than trying to make a living off my paintings. Read more>>

Cellista

The last major gig I performed was at the Lincoln Center. I, in partnership with the Howard Zinn Education Committee, was brought on to perform a composition while students read excerpts from Zinn’s works. As a classical cellist, it was a dream to perform at this legendary place. However, I felt particularly proud to be there, performing my own music, accompanying students while they read leftist literature. Read more>>

Triniity Fantroy

Betting it all on yourself is one of the riskiest things you can do as an adult. In 2016, I was working a corporate job in logistics. Steady income, medical benefits, opportunity for growth in the company.. the standard option for career development in the capitalistic structure. Read more>>

Carly Haupert

As long as I can remember I have always wanted to create & own my own business. There was never a question about whether I would go down the entrepreneurial avenue, however, as the far off dream started to become a reality, the fear started to increase. When I graduated from college, I got my first job in real estate & although it was a pivotal learning experience, it ultimately was not where I wanted to be. Read more>>

TEDDY SOURLIS

At 23 years old, the biggest risk I have taken to date is starting a non-profit organization without a psychology degree, or any prior years of experience within the industry. For the entirety of my life, I strongly identified with being an athlete & eventually, I was gifted the opportunity to play collegiate basketball. Read more>>

Wendy Spillar

I got a divorce final on 1 Apr 22 and had been afraid of going on my own for years because I have a severely disabled 17 year old daughter, along with her 17 year old twin brother and 14 year old brother. I’m unable to work full time because I’m her full time caretaker, but I also could not stay in the relationship, so I started the process in Aug of 2021. Read more>>

Katharine Hargreaves

I’ve taken many leaps of faith over the course of my life – and these risks have more often than not become the initiations I needed to open the next chapter of my growth and development. There are two big risks I’ve taken that come to mind, because they are deeply connected. Read more>>

Mitchell Vinokur

In 2018, I knew nothing about the process of making music and becoming a band. I was just a guy who liked to play around on his guitar like the millions of other people out there who do the same. One day I went to see one of my favorite bands live. I remember watching the band that was opening for them and thinking, “I feel like I could do this.”  Read more>>

Chris Von Hoffmann

If you decide to pursue a career in the creative arts, everything is a risk. Especially if you wish to be in the movie business. However, by a country mile, the most prominent risk I have ever taken is making my debut feature film, Drifter. It was a film generated by my unhealthy anger and frustration at that time. Read more>>

Jahmar Hill

Taking a risk is very important. If I never took a risk on myself, I wouldn’t be a filmmaker. I would have gotten where I am today. Having the #1 movie on BETPlus or closing my first million dollar deal. It took my 4 years to get my film Sisters off the ground, it was so many hiccups then the average person would have quite. Read more>>