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.

Amanda Cureton

Taking a risk on my dream business was one of the best decisions I’ve ever made. Photography has always been my passion. For years, I specialized in lifestyle and wedding photography, capturing meaningful moments. At the same time, I had another love—food and product photography. It was a creative outlet that brought me joy every time I picked up my camera. Even though I felt excited about it, I hesitated to pursue it professionally, knowing it would require learning new skills and making a big transition. After a lot of thought and plenty of conversations where I weighed the possibilities, I finally decided to take the leap. I still remember the day I chose my business name—Creative Thinking 4U Photography—and how real it felt. It was a turning point for me. Since then, it’s been a journey of growth, challenges, and constant learning. But every step has brought me closer to doing what I love. Looking back now, I’m proud of the risk I took because it’s led me to a place where I not only feel excited and fulfilled but also get to help other businesses bring their visions to life through my work. Read more>>

Brianna Toro

With every risk comes growth. Knowing and truly understanding that failure & success both lead to more knowledge & personnel development which we often try to disassociate the two. The biggest risk that I’ve taken in my career is stepping out of my comfort zone and bet on myself. Figuring out ways on how to navigate my business from behind the chair as a colorist and beyond the chair as a stylist has been a journey and It only just begun. 6 months ago I stepped into the styling side of the industry being editorial , bridal & celebrity pro. I assisted along side a friend who is also in the industry for my first shoot . I most certainly try to self sabotage myself into thinking all I knew how to use was a curling iron, which is completely untrue but At those very moments when I doubted myself because I was to afraid to fail is when I proved to myself that my hands are gold and made to create.That step into the unknown and that step out of fear changed my life for the greater good. I put myself out there each and every moment as opportunity was gravitating towards me. I took opportunities that i thought were above me but people believing in me and my work made me believe that there are no limits to my success. In these past six months I’ve worked with top tier makeup artist , stylist, models , influencers , reality celebrities, brides, & top educators. I took risks to explore things I’ve never done and no longer limiting myself because the risk is most certainly worth the reward  Read more>>

Kelly Alexander

Risk Taking may not be for everyone, but when you want to see a difference its important to put your all out there no matter the outcome! Although, my path has privet-ed often while on the same road and destiny, the beginning was about taking a risk. That risk started with me having a vision of working for myself in the fashion industry and selling my own product line but using fashion shows and shoots as a marketing tool. After visualizing this I created a vision board and looked at my finances. They did not match the vision! Yet I refused to allow that to discourage me. If my focus remained on the have not, I would have never pushed for the HAVE! Here is where the Risk kicked in. I sat on the floor and poured out all of the coins I had been saving (you know, those coins that you toss in a jar, drawer or purse), from pennies, nickels, dimes and Quarters, I kept every coin and rolled them up for months. Grand total was $1000.00. I was at the time driving to and from work with an older Lexus that needed some work. Read more>>

Amanda Duncan

This is a hefty topic for me. I feel like I’ve been taking risks my whole life, but particularly, the last few years have seen lots of risky changes. As a creative, spontaneous person with an incurable genetic disease (cystic fibrosis), it’s been hard for me to find the balance between the life I think I should be living and the life I have to live to stay alive. I am 47 years old, a mature age for a CF patient. I have three children and five grandchildren. I had my children rather young, and had spent my adult life, up until 2019, devoted to raising my children. I homeschooled and was a “crunchy” mom in an effort to spend as much time as possible with them as I felt my life was very temporary. I never expected to get old, and honestly, didn’t have any dreams for myself. The only thing I had that felt purely mine was my artistic creativity that I used to help me cope with chronic disease. Read more>>

Kiya Renee

There is always a risk taken when it comes to being creative or going after your goals. You risk being publicly judged, your posts being misconceived, effects of virality, positive and negative interactions. Personally, I had to have a conversation with myself and ask if the risk is worth the reward and if my fears were ultimately stopping me from pursuing my dreams. That said, I took a risk on myself when I decided to become a content creator. I always cared about what other people thought, how people perceived me, if a post would get enough likes, engagement, etc. but I realized, I can’t please everyone and there will always be someone with an opinion. Doing content creation allowed me to be more confident, face my fears and ultimately realize if I like something and it makes me happy, it doesn’t matter what other people think. It can be scary putting yourself out there for the public to see but it’s very rewarding when you can finally say “I did it!” versus years down the line saying “I wish I would’ve.” Read more>>

Mitch Segura

A big risk I took was starting Experimental Brunch with Sam Gucwa. Back in July, Sam played the saxophone for a gig I was headlining at Dazzle. We were chatting at the bar before the show and had the idea to turn our music into a full project. There was only one problem: she lives in Michigan while I live 1,300 miles away in Colorado. Despite the distance, our combined efforts are stronger than ever. We write, produce, and even record together from afar. Sometimes, for bigger gigs, we fly out to each other and perform with local talent. Last August, I finally got to visit East Lansing for the first time and played with some amazing musicians at Michigan State. Even though we’re just starting out, I’m super excited about the future of this project. I never would’ve had this experience if it weren’t for that casual conversation at the bar. Read more>>

Sherèe Browne

When the Pandemic first hit and the world shut down, the financial planning and literacy business I was in the process of building quickly came to a halt. I have known since a young age that my life’s purpose was to be of service to others, and I really believed that was my path. I have always been determined to find my true purpose in life, although I knew it centered around helping people. For over a year I had studied to acquire multiple insurance and financial licenses while bartending full-time at night. I set out to build this practice and target under-served and over-looked communities and industries while teaching them about finances and how to have a better relationship with their money, so they could live more empowered lives while better preparing for the future. Read more>>

Uma Mehta

I was born and raised in Ann Arbor, Michigan, which is one of the wealthiest and most privileged places to grow up in America. I was born into a family that always had enough. My Strict Indian family worked hard and became upper middle class by the time I was a teenager. I was always given everything that I needed, and I never wanted for anything. My childhood was wonderful and privileged. However, my parents were not in support of my artistic and creative dreams. They did not believe that this would make money and were adamantly against me pursuing the career that is actually right for me. I am an artist, and a healing artist at that. I am great at drawing, painting, singing, sound healing, dancing, fashion, design, performance, creative direction, event production, counseling, holistic, and alternative healing modalities, natural medicine, plant medicine, healing arts, etc. Read more>>

Wesley Schauble

I’ve taken multiple risks during my career and every time I take one I’m always taken aback by the reward that I receive. In recent times, the first major risk I took was when my career as a graphic designer began to stall and I was feeling unfilled by the work I was creating. This was back in 2016 and my wife and I were about to have our first child. I was working at Digital Kitchen in Seattle and even though the work was interesting and aligned with my skill set, something was missing. Prior to accepting the job at Digital Kitchen I turned down an opportunity to join Amazon as a contractor and I was beginning to regret passing up that opportunity. I decided to reach back out to Aquent where I had initially received the Amazon offer and spoke with them and mentioned I was regretting my decision and it just so happened that they had another opportunity open up for an Art Director role with the same team. I went through the interview process again and this time I accepted the role. Read more>>

Mark Mcgillivray

Nearly every risk I’ve taken has exponentially improved my career prospects, often after days and nights (and weeks, and months) of hemming and hawing both before and after the singular moment. The two most impactful that come to mind are A. moving to NYC with no job, internship, etc. lined up and B. quitting my full time agency job to strike out on my own as an art director. I didn’t approach either of these lightly. I spend way too much time hedging for downturns and uncertainty, which delays each big leap – only for me to wish that I took each of those risks sooner, so as to reap the rewards. I wouldn’t have been able to be in this career at all if I didn’t move, and I would have much less comfortable and fulfilling of a career if I didn’t strike out on my own.  Suffice to say – take that risk! You can endlessly over prepare for the downsides for the rest of your life, but you can only take the leap once. Read more>>

Lynn Potyen

For six years I helped my eldest son, Erik, navigate his learning disability and one day my husband suggested that I should use what I was learning and share it with other game players. My biggest concern was that there was no template for a game store that focused on brain health. I wanted that to be the center of everything that I did. There was always the potential risk that the world didn’t have an overwhelming need for something like I envisioned. Not just learning disabilities but aging brain issues, socialization issues, and critical thinking, gameplay was a vehicle to help people learn. The biggest problem was that a store like that could be stagnant or fail if I pushed the envelope about brain health too hard. Read more>>

John Gold

Life is all about values. What is the thing you value so much that you would be willing to sacrifice everything for it? Surely it’s not something that anyone can have? Would you stake your life for something that’s not worth it to you? As a spiritual person I value above most else altruism; acts with no remuneration.  To me being aligned with deity is a commitment to caretake those around you and treat them as blood even if they are not. It’s a commitment to make the world a better place. You have to use the life you were given to do the most good. That’s my path. There have been a few times in my life I have come to a crossroads where I felt the right decision was to put into jeopardy stability, comfort, and consistency for the sake of serving others. Read more>>

Matthias Hollwich

In the fall of 2022, I had dinner with some tech friends from Google, Meta, and Apple, and we began experimenting with DALL-E. It was mind-blowing to see how AI on a phone could generate unique visuals. Six months later, after trying out all kinds of AI tools, I gathered our firm’s staff with my partners to announce a bold, three-month AI experiment: every process in the office would explore how AI might be integrated. As an architectural firm, we saw enormous potential but also recognized the risks. The energy and curiosity in the office were palpable, and everyone participated fully. Read more>>

Pia De Girolamo

I have been an artist since childhood. Growing up, I studied with a local artist and took painting and drawing courses in college. I also took a pre-med track and trained and practiced as an Infectious Diseases physician for many years. I had a successful private practice. Eventually, I experienced burnout trying to juggle the clinical and administrative demands of a private practice with family and an art practice. Many colleagues who were experiencing the same thing were leaving clinical practice for jobs with medical insurers or Pharma — a route that did not appeal to me. I had started taking painting courses at local museums and art centers in what little spare time I had, and eventually, began entertaining the notion that I could paint full time. I put off this decision for several years until my husband and I could be sure we could sustain our family on his salary. Read more>>

Mason Engel

I’ve been writing science fiction and fantasy since I was a senior in high school, and through promoting a self-published novel that I released when I was in college, I stumbled into making documentaries. I made a documentary about a book tour that I took and turned that into a film about independent bookstores, and I landed in this weird niche of making documentaries about books. Years later, I had a job in L.A. as a receptionist for Discovery (right before the Warner Brothers merger), and I saw the writing on the wall and knew that our office was about to close. Thankfully, it seemed like I was going to be able to pivot my current position into a new job. An assistant for an executive. I would just have this gap of about two months of unemployment when my original job as receptionist would end and my new potential job as an assistant would begin. I also had this idea for a documentary, this crazy literary road trip. I would travel to 50 states, read 50 books, and interview 50 authors … all in 50 days. I couldn’t really take two months off of a brand new job to go and do this, and I didn’t want to wait a year or two years until the new gig was over. Lucky for me, I had a two-month unemployment gap to fill. Read more>>

J. Lou

Nothing is ever guaranteed in the first place, so anything you pursue is a risk. And I think I knew that from a young age. Seeing my parents divorce and struggling with jobs they weren’t even passionate about. Subconsciously I adopted a mindset of just doing things I wanted to do. Sometimes that was for better or worse, but it was always my decision. So when I decided to pursue music, I wasn’t scared of the possibilities of failure because that didn’t matter to me, I was doing it. Now I’m releasing my own original music and performing multiple shows a month in NYC. Read more>>

Emily Palacios

a risk. What do I mean by that? Well, whether you are a painter, a playwright, an actor, a podcaster, whatever, you are never more vulnerable then when you are creating your art. You are literally sharing a part of yourself that maybe no one has ever seen before, so in that is a big risk. Will people like what they see? Will they connect to it? Will they understand what you are trying to do? I took a big risk in 2020. I was, and still am, a professional actor, in the touring company of a show called Old Jews Telling Jokes. I was on contract in California for 8 weeks when the pandemic started. We were luckily just a few shows away from finishing our run, so we closed the show early, and got to fly home to our loved ones. That same week, the Children’s Theater I had worked for two years decided to close their doors. So in one week I lost two jobs. For a while, like many of us, we thought the world would open back up, but a few weeks turned into a few months, and I knew I needed to start doing something and moving my life forward. Read more>>

Mackenzie Crumbley

I believe that putting yourself out there creatively is always a risk, no matter how you do it. During the COVID-19 pandemic, many people found a chance to reset their lives. At 20 years old, I decided to take a leap and took on a door-to-door sales job. Little did I know, this would lead me to travel away from the East Coast for the first time! In just three months, this job taught me valuable lessons. One of the biggest lessons was about taking risks. I learned that you can hear “no” thousands of times before you finally get a “yes.” But that one “yes” can open doors to bigger and better opportunities. I also discovered the importance of pushing through challenges. Sometimes, your next big opportunity could be just a door away. Read more>>

Kevin Reyes

The biggest risk I took was going full-time into real estate, with no mentor to guide me through the process. I knew it wouldn’t be easy, and the weight of that decision was heavy. But I was driven by a clear vision: to make my mark through social media marketing. Growing up, I’d been far more inspired by content creators on social media than by traditional TV. I’d seen how powerful platforms like Instagram and YouTube could be in building real connections and communities, so I felt this approach could set me apart in real estate. Read more>>

Juliana Shun

I was at a crossroads in my life, caught between the comfort of anonymity and the desire to express my true self. I always knew I was a creative person. Art really resonates with me. I was not always into fashion; however, I used it as a form of visual communication due to my hearing loss. I later became infatuated with fashion itself and admired this art form. Something shifted within me as I first discovered the world of thrifting and vogue magazines. I realized I wanted to embrace my individuality, not just for myself but to inspire others to do the same. Read more>>

Laura Bartlett

The pandemic caused a lot of disruption in the world and specifically the fitness world. When everything shut down, as a studio manager of Orangetheory Fitness I realized how vulnerable my career choice was and the effects that a public emergency like that could have on the world and my personal life. I lost my job, like many others, and found it very hard to see the light at the end of the tunnel during this crazy time. While I had lots of time to think, I was bored and felt I needed to find a way to create another stream of income or study for a new career path in the case that the gym was to never re-open. Thankfully, at the time I had a close friend entertain the idea of becoming an Insurance Broker and I knew it couldn’t hurt to get licensed. I got to studying and became licensed as a Life & Health Insurance Agent in the state of Colorado within a couple months.  Read more>>

Luke Dicola

The risk I took was leaving a job I was comfortable at to start my company at the age of 25 without technically having a single client. I was 3+ years into my role as the in-house videographer, editor, and motion graphics designer at a higher ed marketing firm, which was my first “real” job out of college. I’d had an incredible experience to that point, but the routine was becoming a bit stale, and I couldn’t escape the feeling that I’d outgrown my role at the agency. I put in my two weeks and mentioned to my boss and mentor that if there was any opportunity to freelance in the future, I would love to continue working with them in that capacity. They told me they’d consider it, but I wasn’t counting on it. At the time when I left the agency, I had a few shoot days lined up and a trip to Wisconsin for 3 shoot days, but nothing beyond that. Just days after my final day at the agency, the Wisconsin shoot was cancelled. I didn’t panic, but there was a bit more free time in that first month than I would have wanted. Read more>>

Nicolas Cambi

Making the leap to hobby to Professional Status I originally won my procard in 2015 when I went to Wilkes-Barre PA and beat 27 other guys for the chance to win the professional status. However, I didn’t really feel I made the full commitment to be a professional strongman until 2020 after the pandemic. Once the sport was taken away from me, is when I really bought in to come the strongest version of myself. Making the leap would potentially strain my progression in corporate America but would allow more time to compete in more competitions domestically and internationally. In addition, allow me to improve every aspect of my strongman game, technique, diet, conditioning etc. Read more>>

Jaamal Mckeithan

I am a sneaker head that fuses culture with art. I’ve been to tons of events, shows and stages where women always been an after thought to the sneaker and art community. I’ve used my platform to highlight women who are dominating the sneaker game and art industry. I wanted to break that , by using my brand to put women in the spotlight daily and first! Read more>>

Corey Barnes

Back in February 2021…. My life changed forever… Life happened and I wasn’t equipped to handle it… came out of nowhere… I decided to deal with it all alone… and it was tough…real tuff.. but I endured… minute by minute.. day by day… I dealt with it… Then… I made a decision that I thought was mine at the time… I now know that it was God ordering my steps… I went away to hit the restart button.… didn’t tell anyone, didn’t plan anything, I just left… All of my life…I had never really been a risk taker. I had become very comfortable with being comfortable… I have since learned that a comfort zone is where most people go to die…So, one day I decided to take a risk that would change my life, but ultimately it looks like exactly what I was supposed to and needed to do.  Read more>>

Ari Spence

It was 2019 and I was set to graduate law school. I had already worked at one of the best known civil rights firms in New York (arguably the country). I had already been cited as establishing new case law in prosecutorial ethics. I was already working in an office in Executive Boulevard at the District Attorney’s Office, as an intern. To those around me, my legal career seemed like a slam dunk. It could have been, too, if I decided to continue. I came to a jarring realization in my third, and final year, of law school: none of that was what I wanted. My whole life I wanted to be a creative. I wanted to write, to perform, to make and share art with people. However, growing up in a trailer by the river did not make that a practical choice. Now, I was an adult with a dying mother and a choice to make. The time had come to choose my happiness or practicality. I chose my happiness. Read more>>

 

Lamia Pierce

Oftentimes we stumble through life trying to find our purpose without realizing that our purpose is within and in our hands. I believe this outer quest is based on uncertainty because we are unsure of where the next step will lead us. For years I lived with that uncertainty, I was a woman with words bubbling inside of me, yearning to be released but I could not release those words beyond the pages of a journal. Fear held me back! I never thought about becoming a writer, yet it has been the one thing that I’ve been doing since I learned to write. Somewhere in the back of my mind I questioned how being a “writer” could be my purpose. The idea of becoming a writer, much less a published author was too risky. By putting my written work out into the atmosphere and in the hands of the public I felt I was risking rejection, embarrassment, judgement-I was also risking my identity and my passion. Read more>>