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.

Ashley Arkels

I moved to South Florida from Louisville, KY in 2012, to record my first album. I had just signed with a new label in Nashville and was their first artist. I had traveled to Miami before and recorded some original songs with producers, so I was excited to go back and get to work again. Nothing quite went to plan. I got a bartending job to support myself while I waited for recording budgets to be finalized, but it never happened. I ended up getting a second bartending job because if you’ve lived in the Miami area, you know you need a real career or a second job to pay for housing and food. Read more>>

Roger Langdon

For most of my professional life, I had been making a comfortable living in the new home construction industry in Southern California. While I was “dabbling” in musical endeavors, I never saw it as a primary means of income. It was always a “side hustle.” In 2008, the economy took a severe downturn and hit the new home market particularly hard. I, along with many of my professional colleagues, found ourselves out of work and desperate to find something stable. I bounced around with a couple of small companies, making a fraction of what I was making. It was then that I realized that I was in a position to make a complete change and focus on my “side hustle.” My rationale being, “If I’m only going to make a fraction, I may as well make 100% of that fraction in my own business rather than supporting someone else’s company.” Read more>>

Maryellen Bishop

The biggest risk I ever took was at 25 years old. I was working in sales/marketing, and decided I should’ve gone ahead and followed that original dream I’d had of going into medicine. So I started re-taking college science classes that had expired (most medical programs want the courses to have been completed within 5 years), and dipping my toe back into the idea of changing career paths. I also switched over to a job as a medical assistant with a dermatology practice to learn and get the required patient care hours. Read more>>

David Hector

When quarantine happened in 2020, my job closed down. Since I was in the dance and entertainment industry all of my work was put on hold. That’s when my wife and I came up with A.C.E Studios. It started out as online dance class on zoom, for kids that were stuck at home. Once the quarantined lifted and most of our students left, we transitioned to after school dance. From there we moved into all forms of dance lessons and entertainment, but it started with taking the first risk. Read more>>

Mara Benson

I never planned on being a Realtor. I struggled at school and tried college twice, I just never enjoyed it. My father taught me to work hard. I always had visions of owning my own business, I just didn’t know what that looked like. In 1998 I moved to Arizona, met my husband and we had two children. I had my first taste of sales in the .com era, I absolutely loved it! But, with the crash I was never paid for all of my hard work. My second sales job was in Scottsdale selling CRM Software and support contracts. This was an inside sales job, I was stuck at a desk and driving in traffic to work during horrendous hours dropping my children off at a home day care. I was exhausted. Read more>>

Juliet Mendoza

Risk-taking requires a leap of faith, as it often involves venturing into the unknown with no guaranteed outcome. Last year I took my leap and it has made me grow into a different person with different goals. It has pushed my creativity, resilience, and problem-solving abilities. I have always been a jumper, letting the universe do its thing for me and having faith that I am on the right path at the right time. I was a chef for over 13 years and had a 9 to 5 since I was 15 years old. Doing what I love has given me a new way to look at life. To understand that now I am in control of my future. It’s not easy, you have to have a strong mindset on your bad days and you need to keep a routine to make sure you get your work done. Staying on top of everyday life and family and the lifestyle I have chosen comes with trying your best to find the balance. Read more>>

Fadi

Once I consciously, and intentionally decided to tell fear to F**K off, everything changed. It hit me hard … What was the point in knowing that I hold a specific purpose or passion, and not pursuing this in my life? No point at all, so I went All-In. No “plan B”, on purpose. Fear is not real. Read more>>

Hassan Said

Life of an artist in this day and age is nothing but risks. In a capitalistic society were there is no currency or desire for art as much as “content”. Embarking on the journey of an artist and filmmaker is akin to stepping onto a tightrope suspended between creativity’s boundless sky and the unknown abyss below. With each brushstroke or camera angle, one takes a leap of faith, risking vulnerability to give life to imagination’s vivid tapestry. These risks, though exhilarating, are rife with personal stakes. The risk of rejection looms, a disheartening echo if your masterpiece remains unseen. Financial gambles, trading stability for the prospect of artistic freedom, create a pulse-pounding tension between passion and practicality. Yet, amidst these uncertainties, there’s a profound intimacy in revealing fragments of your soul through your art. Read more>>

Marísa Adame Grady

I’ve always loved movies. I always dreamed of writing and directing my own films — but it always felt unattainable. When I showed a script to a friend who said we could make it a reality, I was nervous. Excited, sure, but nervous and, to be honest — I was scared. What if whatever we made didn’t live up to what I’d been imagining? That’s how I dove into my first professional short film: nervously putting one foot in front of the other. In college, I had made short films where I was the sole participant: writer, director, actor, camera operator, editor. It felt easier to try — even fail — alone. Since then, I worked with video production companies in various capacities, and basically every side of the filmmaking process. Read more>>

Hope Raney

In my life, risk taking has always been the general theme. Not just any risk though, calculated risk that is propelled and fueled by my dreams and visions. Ever since I was a little girl I have been taking the risk of bearing my art, soul, and talent with the world in hopes that one day it will connect with people on a larger scale. I have been very Blessed and supported in my journey by my family and my friends, but at times, the risks that had to be taken were up to me and me only. I went to Berklee College of Music and then took the risk of moving to Los Angeles in 2011 and it was the best decision of my younger years. Read more>>

Kate Kayaian

In the first days of the 2020 lockdown, I knew that the years of experience I had teaching my cello students online (due to my travel-heavy lifestyle) could be helpful to my colleagues who were being asked to transition to online teaching literally overnight. It meant that I was going to have to be visible in a whole new way–not as a cellist or performer–but as a coach. As someone who could teach my colleagues something. That felt bold, scary–terrifying, in fact–and I knew it was a big risk to my reputation. Afterall, many of my colleagues questioned the validity of my online teaching–They didn’t think things could be as effective as an in-person lesson, and swore they’d never do it. Read more>>

Dmitri Zurita

Being an artist generally means committing to a significant degree to the concept of risk. In artmaking without risk there is little to be ventured in the work and for the artist–aside from commodity production–doesn’t “grow” without taking risks. So to be an artist is to be in bed with risk, and in that precarity life can enter the work and something meaningful might occur. Read more>>

Tenaj Faustino

For us, our story of life changing risk began when we decided to quit our jobs, sell our home and move to Malaysia. You see, we lived in New Orleans for ten years and had excellent paying jobs before we decided to pull the plug on “ The American Dream” because we finally realized it really wasn’t our dream. Yes, we were entrepreneurs, we owned our home, and we threw parties whenever we wanted. We vacationed twice a year with our kids and then one day Tenaj had a stroke at work, which she never saw coming. Luckily for us she was treated immediately but we found out she had an undiagnosed aneurysm in her brain. Needless to say, with so much happening, Tenaj took some time off, well during this time we started watching a popular TV show, House Hunters International, and we were shocked by the low cost of living internationally. Read more>>

D Chamberz

I started taking music seriously when I got out of prison. I knew while I was inside that I needed to do better with my life, and took that as an opportunity to figure out who and what I needed to attack when I got out. I used it as a learning experience. When I got out, I got involved with anything and everything I could to make connections and build myself. I was loosely involved in the battle rap world because I was in a group with Math Hoffa, Cortez, Hollow Da Don, BK Bless and a few others called NYB, but, I never got in the ring, it took me a long time to shake that image of me being a battle rapper, and separate myself into the music world. It wasn’t until I got a publicist and manager that I started to steer my career in the right direction. Read more>>

Dale Ellliott

I have taken multiple risks in my Life that has benefitted both my family and my Career. risk 1 : Moving to Los Angeles CA straight from Jamaica by myself with no family members or money. Just a dream. It worked out because I received help from good people and I also learned a lot of things about my industry and how I want to operate moving forward. risk 2: Started stand up comedy without any practice. Now I am risking it by booking venues and selling out my own tours. This could have been a financial disaster as well as a failure but I decided to do what i love and this is what I’ve always wanted to do. Read more>>

Del Bloque

Being an artist is all about taking risks, especially in Mexico. To make a living through art is an act of faith in yourself, your music, and choosing the path of taking the risk to go after what you want – not just in your career, but also experimenting with different sounds and lyrics. Opening your heart while writing and singing is something I find powerful – so it’s important to keep in mind that its always worth it to take risks. Read more>>

Gabriel Yared Aya

In my personal opinion, no big business can be successful without taking a risk. The bigger the risk, the more potential reward. So I equate business ownership or entrepreneurship as calculated risk, or like playing poker. The more in tune we are to our innovations and projects, the better we accomplish them, causing more unique outcomes from these risks. Read more>>

Seyanna Hitt

Becoming a ‘staff’ member of Colorado Cross-Disability Coalition (CCDC) was not the biggest risk I have taken in my life but it is one of the most life changing “risks” I have taken thus far in my career. When I first joined, I was brought on as a Youth Fellow and contracted for two years. At the time, I was semi-fresh out of my Masters program, doing independent consulting with local nonprofits and navigating life with a toddler and newborn. I had taken a significant amount of time away from the traditional 9 to 5 schedule to complete my Masters of Nonprofit Management and be a stay-at-home mom with my first born. Read more>>

Ashley Wood

A risk I have taken is writing my first book, which was officially released on September 12. I started the journey near the end of last year after returning from my birthday trip. While it may seem small to some, you just never know where the writing path will take you. I successfully accomplished the very extensive tasks of self-publishing. It’s not for the faint! But it’s a non-fiction book based on the full circle healing of my and my father’s relationship. I address the daddy issues I carried throughout my childhood and adulthood, the rejection I felt as he and my mom were at odds, and the impact of their divorce as an adult. I’ll tell anyone that divorce is harder for adult children than for small children. We don’t bounce back as easily. Read more>>

Mikayla Szathmary

So to start, this may be a very unconventional answer, but very on brand for myself as I don’t tend to do anything the conventional way. This story isn’t something I talk about very openly except for with family and a few close friends, but reading the writing prompts it’s something I felt called to share so here it goes. The biggest, most life changing risk I’ve taken thus far would be making the decision to end my marriage and raise my son as a single mother. Taking the risk to leave everything I had known and grown accustomed to the last 4 years, including the house we brought our son home to, to completely start over was the most challenging thing I’ve ever done. I wanted so badly for my son to grow up in a happy, healthy, loving home and the hard truth was that our current circumstance was just not going to be that for him. Read more>>

Rachel Kelly

Two of the scariest things I’ve done in my life were moving cross country alone from NY to CA to fulfill a life long dream of living the California dream and quitting both my therapy jobs to join a business coaching program and start my journey as an entrepreneur. There were so many valid excuses to stay in NY. I fell in love with someone four months before my scheduled flight, my mom had just passed and I had a job I was happy enough in…and yet my soul knew I needed to make the move. Despite it breaking my heart, my gut knew I was meant to do the move and I’m so glad I did. I just had my four year anniversary of moving to San Diego this past August and I’ve never looked back since. Read more>>

Elisa Wiggins

With trepidation and excitement intertwining within my spirit, I embarked on a journey unknown, leaving behind the comforting embrace of a place and a career I held dear. In this new city, a tapestry of unfamiliarity greeted me as I ventured forth, accompanied solely by my father and my bonus family. I had so many questions that casted shadows of doubt on my path, like where would I find my purpose, why here, where would I find a place to call home, who would I meet, and how would I be provided for? And I had two weeks to figure it all out once I gave my notice where I had been living. Yet, an inner compass guided me, a whisper or still small voice inside, urging me to seize the opportunity to begin anew. Enveloping the winds of change, I embraced the risks that lay before, relinquishing possessions and embarking on a cross-state adventure. Read more>>

Vikki Gladney

Wow, this is an easy question to answer. I imagine, as my business has grown, and decisions are made, I have taken some definite risks. Yet, the biggest risk and the first that comes to mind is stepping out with big faith to start my business. I founded Natural Measures in 2020 after walking away from the stressors of a corporate level job, and opened my doors October 2020, during the pandemic no less. Read more>>

Hunter Bates

Life is all about taking risks, learning, and growing. I’m a pretty firm believer that everything happens for a reason, and without taking some risks, I’m not sure where I’d be at the moment. When I moved out to Denver in 2018, I took the risk of moving somewhere where I knew few people, and no real timeframe of how long I would be here. And now, as I’m hitting 5 years of being here, I feel like I’m supposed to be here playing music, and I’ve been more motivated and eager to learn and create as much as possible. Read more>>

Matthew Reynolds

I believe most people would call it a “risk”, but I call it living life. There have been several major risks that I have taken, and since the past is our education, I have chosen to learn from each and everyone of them. Passion one, theater and dance. I started out at the University of Minnesota as a Mathematician and Aeronautical engineer. I was really good at numbers, math, and equations, but it didn’t bring me any joy. Plus all the people around me telling me I should go into these fields could only tell me that I would be making a lot of money, and nothing about being happy. Read more>>

Julian $tyles

I’m Originally From Columbia,SC Where My Friend Mellow & I Had Hosted our Own Music Events With our Collective 187BLVD Where we had Performances Merchandise & Artist Development we have some artists their first opportunity to perform n with that We decided to Take a Risk to move to LA to Further our Creative Vision & So far its been going great Started my own clothing brand picked up new skills like photography Read more>>

Denise Khumalo

The biggest risk that I have taken in my entire life was leaving my hometown (Harare, Zimbabwe) to move to the US to pursue my film career. Moving to another continent, alone, as a teenager was definitely not easy. But I knew it would allow me to have more opportunities, which I am happy and grateful for. My journey to America started off in upstate NY at SUNY Fredonia where I received my BS in Communications: TV and Film. Then I moved to Los Angeles over a decade ago to get my Masters in Filmmaking at New York Film Academy located in Burbank. Being exposed to the film industry on both the East and West Coast has made the creative that I am today. I went from working on projects for free to making a steady income as an independent contractor which is not an easy task. Read more>>

Matt Ellis

I served in the Army and Department of Defense for over thirty years and have never seen our country more profoundly divided along ideological, cultural, and racial lines. In a country that projects progressive values and inclusion, irresponsible political rhetoric has led to the targeting of underserved and vulnerable communities. These dangerous agendas were never more apparent to me than when I witnessed the migrant caravans cross from Honduras to Guatemala, where I served as a senior security attaché. Conservative voices at the highest levels of our government demonized the migrants when they only banded together to protect themselves against the transnational criminal networks, human traffickers, and Narcos, who would exploit, rape, and kill them on a whim. Read more>>

Christina Morgan

I had been introduced to a areola tattooing through some permanent make up forums that I was a part of. I did not think I was capable of doing such art, since I was only focused on doing really good eyebrows at the time, and I had a friend who had gone through breast cancer and breast reconstruction. I was totally willing to refer her out to those locally within the central Texas area that could help her out if she wanted to have her nipples tattooed; maybe to help her return to a sense of normalcy . Then I came across a student of my mentor, who produced such beautiful realistic Areola tattooing that it gave me goosebumps and still does to this day by the way. Read more>>

Tatianna Mack

This year I told myself that I would no longer let fear control me. In June of 2023 I went to an open reception at the Tanya Weddemire Gallery the exhibition on view for “A Tree Grows in Brooklyn” by N Carlos J. I was so moved by his work. So I took a risk by pitching my idea to the founder/curator about hosting a meetup. We set up a meeting and I pitched my idea. Tanya Weddemire & Dianne Gibbs agreed to having the meetup. So we had the meetup on 6/24/23 and it was a success! Now I work with the gallery. Read more>>

Sydne Blahnik

It’s easy to miss your calling when you avoid taking risks. Growing up, I always tended towards risk taking – from climbing trees, to cliff jumping, to spending 16 years as a gymnast – I was always looking for ways to push my limits. Something I realized quickly is that many people think that being “brave” or taking risks means that you aren’t scared – this couldn’t be further from the truth! Bravery is FEELING that fear, facing it, and overcoming it. Read more>>

Rick Rusch

During the COVID-19 2020 lockdown, I made a decision it was time to move forward by changing my direction with my photography. Up until this time, I was a freelance photographer skilled in editorial and lifestyle photography. Several years prior to 2020, I started a blog telling stories about people who made a difference in life in words with photos. In 2020 I decided it was time to be freer in my life by selling my house of 20-plus years, plus I sold most of my belongings. Since then I haven’t bought or rented a place to live. I live freely staying here or there. Read more>>

Gerardo Christ

I worked for one of the big car companies and I was already Management but it wasn’t my dream my dream was art music and Culture. I am the lead singer Of Heavenly Trip To Hell an industrial metal band SO i quite and openwd a Rocknroll store called No Regrets that was open for 13 years were we supported local music local art and unity in the community..That lead me to the Tattoo world….Now I Own Belmont Hights Tattoo Boutique In Long Beach Ca I also direct and produce Road Dogs Tv were we showcase local talent with international Bands … music Art Culture =unity. Because I took a risk Heavenly Trip to hell will play hell and heaven music festival 2023 wish is the biggest music festival …Take a risk you cant change the whole world but you can change your world the world around you. Read more>>

Daniel Grier

Starting anything is to take a risk and bet on yourself. Starting my brands has been the most challenging thing to date but those same challenges define your character. I have learned so much about people and business through my journey over the last 10yrs. I am grateful to have seen this journey through for this long. To have impacted the lives I have, dressed the stars I have been able to work with, champion some of the causes I have brought light too, and inspired and uplifted others in the process. I am grateful to do what I love and to continue to see myself grow as an artist. The risk does come with rewards and it’s important to really take those wins in and smell those flowers. Read more>>

Heather Rogers

Starting a food truck business, essentially any business, is a risk. There’s an idea, an execution, and a prayer that it will succeed. the most challenging part of being self employed, is being totally reliant on yourself to be motivated every single day to get up and get the job done. Read more>>