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.

Zac Barnett

From a young age I knew I wanted to be some sort of musician. Growing up performing in bands & musical theatre productions I made the choice to commit full time in high school earning me a spot at Berklee college of music (where I really just wanted to meet like minded musicians to collaborate with). I had no financial backing, missed the cutoff for loans so I took the risk to ask a family friend to lend me just enough to attend 1 semester. Read more>>

Eric Elfstrom

Every day I try to take a risk with whatever I’m in the process of creating. My first and biggest risk would have to be the first time I shot at a stadium concert. It was at Fenway Park in Boston and I was with Illtown Sluggaz because they were opening for New Kids on the Block. I was very nervous because of the massive stage and looking out and seeing a sea of people. Read more>>

Jordan Blanchard

I sort of took two major risks early on in my career. The first was deciding the career path. I already was broke coming out of college, so I decided to become a musician? Lol. I built a name for myself by playing 225 shows in my first year (2021). They were 4 hours each, and I was singing 100% covers. To be honest, I learned to hate it, and I often wondered if I had what it took to keep going. Read more>>

Klementyna Bohdanowicz

I feel like my entire journey thus far has been about taking risks… I was born and grew up in Warsaw, Poland. My parents divorced when I was just 6 years old and I lived with my mom visiting my dad every other weekend. As a child I suffered from insomnia and a fear of sleeping away from my home, which limited my childhood experience in terms of sleepovers, school trips, or sleep-away camps. Read more>>

Azeeza Adam

In the midst of multiple COVID-19 lockdowns, I decided to start my own makeup business. It sounded so stupid to me at the time because why would I want to provide a service if no one can go to events? I was 13 years old when I found my love for makeup. I always did it for fun. I would sometimes stay up till 3am because it was that therapeutic for me and it was sort of an escape. Read more>>

Joseph Goldsmith

To quote J.R.R. Tolkien, The Lord of the Rings, “It’s a dangerous business, Frodo, going out your door. You step onto the road, and if you don’t keep your feet, there’s no knowing where you might be swept off to.” These two sentences speak the utmost truth in life. The decades of my adulthood have been nothing more than a continuous path of risk-taking in both business and personal ventures with each one bringing trials, rewards, and lessons learned. Read more>>

Robyn Reynolds

I often think that life is a risk generally speaking. We never know how anything is going to work out no matter what we do. There could be risk in moving to a new city, taking a new job, getting married, or starting a business. I moved to Los Angeles from New York where I had a career in fashion. Read more>>

DJ Roueche

I moved to Los Angeles from Virginia when I was 20 years old. The only person I knew in California was my buddy, who I was moving to California with. I had a little bit of money saved up to get me on my feet once in Los Angeles, but I didn’t have any job prospects or even a real plan to find a job I wanted. I had the safety net of knowing I could move back to Virginia if things didn’t work out for me in Los Angeles, but the plan was to make it work in Los Angeles however I could. Read more>>

Isabella Kelm

One of the biggest risks I have taken so far in my career was quitting my full time job with no back up plan. I had a decent schedule of clients that wasn’t not very consistent throughout the months, very little profit coming into my pockets, and had no guarantee I would be able to keep the business afloat without my second income. While I was still employed at my previous job, I had moved to a studio that was much more affordable for my budget and customizable to fit my liking. Read more>>

Christina Chao

Life is about taking risks, and if we don’t take the risk, we live in fear and regret. I lived most of my life being risk adverse, taking a bunch of cautionary steps to avoid failure as a symptom of my perfectionism. However, when the pandemic hit, this was a turning point for me in my risk-taking efforts. I was working a full time commercial real estate job, and was completely burnt out, in addition to ignoring my health. Read more>>

TJ Legler

With any creative endeavor one is completely exposed. Throughout the 8 years I’ve been in business I’ve learned it is better to take risks than not, as new opportunities usually manifest from being bold. While many artists do what I consider “pro bono work” I have found the value of actual paid work which follows from doing such things yields way larger returns than being greedy or demanding immediate pay while denying bigger future opportunities. Read more>>

Jamarr Farmer

I see that everything in life is about taking risk. I look at the media that praises the few that “make it” in comparing to the those that done with is an hall of a lot more. That’s when i starting looking at music and podcasting as passions that gives chance to be me and contribute to the world. I do work an fulltime however, I disciplined myself to not be so depending on just that job but give my energy to my creative passion. Read more>>

Shannon Lee

I believe in life that it is very important to sometimes take risks, I personally call it a “leap of faith”. There are many moments in my life that I took risks while not knowing the end result. My content creation journey is one of the risk that I have taken & have not regretted. I wouldn’t consider it a major risk in my life, but I would say it was a monumental risk. Read more>>

Chrissy Fagerholt

When I fell into the world of games and toys, it was with a game called Friend or Faux that I created on a whim with three of my friends from childhood. After a successful Kickstarter, we got the opportunity to license our game with a major publisher. This was awesome, a company liked our idea enough to take it on, handle the manufacturing, selling and shipping, while we sit back and collect the royalties?! Read more>>

Tre’la Peters

The major risk I took in my life was starting my business. I was working in corporate America and knew that there was a greater call over my life. I wasn’t fulfilled and I needed to find make moves to put me in position to walk in my purpose. I took a leap of faith, quit my job and poured everything into my business. I had one child and I was pregnant with another and that was the biggest risk but so far it has given me the greatest reward. Read more>>

Annmarie McArthur

The isolation of the pandemic was a blessing in that it forced me to examine my career. I had worked every side of the food industry up to the point of lockdown. End-user, owner, COP sales, brands manager, broker, food service director and more. Made the decision that being an entrepreneur was what I do best. Took the decades worth of skills and professional relationships I had developed and decided to sell my home and move across the country, to the beach and start a new company. Read more>>

Andres Galeano

When life goes smooth and everything seems to be falling into please, one thought start bugging your thoughts day and night, it only gets stronger and stronger the more you try to ignore it. The question keep floating in you brain regardless. What are you going to do next? is quit frighting to be honest but also it bring an awkward excitement with it. Read more>>

D.A Smalls

I was always a risk taker whether it was stealing food so I didn’t have eat noodles an hot dogs all my life or stealing to survive while I was sleeping outside eating out of a garbage can. To even sacrificing time with my family just to fill a void by striving for greatness due to my life. I have always taking risk, But these type of risk after I developed a relationship with GOD is different. It’s been more so operating in Faith. Read more>>

Rachel Bailey

I created my initial business, Rachel Bakes at Home, in 2020. Rachel Bakes at Home was a food blog as well as my social media brand. I developed recipes and provided photography to various brands as well as posting content on social media and websites. All of this while working a full-time job as an attorney. The scope of work became overwhelming and, piece by piece, things began to fall away. Read more>>

Danny Lau

I started as a passionate student in the “Acting for Film & Television Program” at Humber College. My family and friends strongly disapproved of my choice to pursue this career path. Frankly, they were justified. I had no connections in this industry or any formal training in this craft whatsoever. But I knew I had an affinity for storytelling and I loved films. Films helped me through a tough childhood. Read more>>

Jack Trottier

On May 20, 2023, I left my driveway in Tyngsboro, MA on a handcycle journey to the Shepherd Center in Atlanta, GA. It had been ten years since I was in inpatient at Shepherd from a spinal cord injury when I was seventeen. With the recent start-up of my foundation, we wanted to begin a new chapter of life while doing some good for an organization that needs support. We planned to raise funds over the four-week trek down south to benefit the adolescent program at Shepherd. Read more>>

Wanita Dixon

I’ve wanted to be an artist since age 5, and like many would be creatives, I was discouraged from pursuing art as a profession. In the 8th grade, I met engineering college students and decided that I wanted to be an engineer when I grew up. Read more>>

Sean Martin

I guess most people love to gamble, but I learned gambling with the music business is never rewarded. Whether they admit it or not, everyone wants something for nothing. The pro’s and con’s list, the crucible of scrutiny, the razors of prior experience: these things we rely on to help us determine gain from loss. Read more>>

Blessing Beam

When I first started modeling I had no idea what I was in for. Doing research, traveling, and taking pictures. But the most struggle was doing it alone. Me being one of the first kid in my family to pursue an industry career. Like acting, modeling, and or music. I had to completely do everything for myself. Especially traveling. Read more>>

Shuni

Taking a risk to evaluate myself. My past version of my self I was partying in the club and drinking with so called friends. Back to back to back. Thinking that I was honestly missing out on something. Wanting to be seen. Wanting attention and wanted eyes all on me because mentally I didn’t want to be alone. Mentally I didn’t understand the meaning of life. I wanted to be around people to feel safe. Read more>>

Chanel Kincaid

This past January, I finally decided to quit my miserable job and become a full-time creative. Between my consistent DJ gigs and designing fliers, I’ve been able to get by. Sometimes imposter syndrome gets in my way, but the support and validation I receive from the community is a reminder that investing in myself was the right decision. Read more>>

Steven Cuoco

In the world of entrepreneurship, where running your own company is a delicate balancing act, the art of time management and choosing the right clients becomes paramount. Financial landscapes fluctuate, economies ebb and flow, and projects can be abruptly halted, leaving you grappling with the weight of bills to pay and a dedicated staff to support. Read more>>

Barbara O Stephenson

I’m kind of a “risk-it-when-you-have-nothing-much-to-lose” person. Taking a risk is about being proactive and living your life by not taking the simple/easy/or obvious path. There are so many opportunities in life and understanding your tolerance for how much risk to take is key to running a business. Read more>>

Peace Ransom

My biggest risk was selling all of my possessions and buying a one-way ticket to Las Vegas. I have learned that to achieve anything great, you must leave your comfort zone. I was comfortable in my hometown but I wanted more for my life and to expand my business. I did not have a home, a job, or anything set up but my soul was being called to move to Las Vegas and so I listened. Read more>>

 JP Haley

I recently got hired – and left – at my local McDonald’s. I worked there for close to a year and the amount I learned is crazy, but I absolutely hated it. I’m sure a lot of artists can relate to trying to create while working a 9-5. They had me on closing shift and management was awful – I was quickly moved to a shift manager and handed a huge chunk of the responsibilities for the store. Read more>>

Damon Terry

Sacrifice with unimaginable Faith and with risk must come with reward. Read more>>

Ashley Woodcock

When I married my husband I obviously never dreamed that our fairytale romance would end in a separation, especially after giving birth to our beautiful daughter and miracle baby. Yet here I was, a new business owner, a new mom, and now finding myself single at an age where society makes it seem scary to be on your own and starting over. Read more>>

Matthew R Kerns, MFA

Learning to love is a big risk. Life changing. I was living alone and resigned to own the moniker: Confirmed Bachelor. Buried in work, staying late, and never feeling great, surrounded by toxicity. Solitude. Sadness. Frustration. Until that afternoon of pride, and evening of Verdi, On a dime, it was all different. I risked to love and learned to trust. Read more>>

Kate LaVigne

I opened my business as an independent contractor within a larger, successful chiropractic practice in March 2015. In August 2020, during the height of the pandemic, I went completely on my own and moved my office into my own space. It was a risky thing to do during a time when the economy was unstable and I work in an industry that requires physical human contact. Read more>>

David Goolsby

I’m the type of person who thrives when backed into a corner. My best projects and papers in school were almost guaranteed to be done right before the deadline. I guess you can call me a “clutch player” of sorts, or maybe more accurately, a chronic procrastinator. Nothing motivates me more than high stakes. Read more>>

Ty David Lerman

I was late to come out as a gay man, at 23. There was bullying, but never about being gay, there was no homophobic trauma, there was no specific reason for me not to come out, it just took me a while to get there and be able to speak about it. It derailed my early college life and I dropped out of my second year of school with a dismal 1.9 GPA. Read more>>

Chee Bravo

I left my home country Trinidad & Tobago to pursue an education in the Arts in the United States. I had saved just enough money over a period of four years to attend a small private college in Miami, Florida for one year. As an immigrant I could not work so the money I came with was all I had. I plunged into my studies, pushing myself to the limit while relishing the opportunity to follow my dream, even if it was only for one year. Read more>>

JAN RENTENAAR

I love working with clay. It can imitate any texture or shape . No power tools necessary to form the sculpture. Many ceramic artist are intrigued by the science of firing the clay, the formulations of glazes. I am not. I see it as a huge risk. I was fortunate to meet a group of people who spent years building and learning how to fire a kiln that uses wood called a “Anagama”. Each firing of this kiln is a seven day challenge. Read more>>

Kartar Diamond

 

To become a Feng Shui consultant in the early 1990’s was, for me, taking a big risk. Hardly anyone in the United States had heard of Feng Shui and I didn’t even bother with a business card for a long time. “Feng Shui” sounded more like an exotic Chinese dish than a metaphysical discipline which studies the influence of man-made and natural surroundings. Read more>>

Chioma Okoronkwo

I used to be a corporate superstar, but my drive for perfection was fueled by a “lack mindset” from childhood, and it was slowly killing me. Art was always a hobby, but it wasn’t until I moved to Philadelphia and met young artists that I truly found my voice. After retiring from the corporate world due to burnout and physical exhaustion, I struggled with uncertainty and dwindling savings. Read more>>

Afam Onyema

When my father attended a prestigious British boarding school in Nigeria back in the 1950s, he served as a student assistant to a British missionary doctor who was caring for his school and the surrounding community. She instilled in him a passion for medicine and a desire to care for his people through improving their healthcare. As a young man, he made a promise to that doctor that he would bring better healthcare to his homeland — that he would save lives there. He left for the United States with my mother with that promise still warm in this heart. Read more>>

Elizabeth Robbins

Becoming a professional artist is probably one of the most risk taking business there is. My older brother wanted to be an artist but my Father told him that he couldn’t make a living at it so he became a lawyer instead. I think most people have the idea that artists don’t make any money. I’m one that defies those odds. In my circle of art friends it’s more common to make money than not but it does take a lot of hard work, Read more>>

Emmanuel Smart

Being a rapper or an artist in today’s time alone is a risk but they’re were plenty more that i took on the way to where I’m at right now and more i’ll take in the future. When i decided to do music full time, I didn’t quite have an idea of what exactly i was getting myself into, but i took that risk because music is something i love, cherish, and a way for me to express myself in any situation. Read more>>

Teri M Brown

Although I said I wanted to be a writer when I was a child, that was never something I believed could be a real job. My parents believed that being a writer was saying that I wanted to be a starving artist and work as waitstaff in some dive restaurant. So, I went to college and received two majors and two minors because I couldn’t settle on something that fit. Read more>>

Trina Randall

Wow!! Where to start!! Back in 2021 I was working for children`s social services. This was a job I had done for 10 years. The stories I could tell you!! I loved my job. I loved helping and supporting people. I worked with a really amazing team who were friends as well as team mates. Things were really good. Read more>>

Tatiana McCrea

With any career shift, there is a leap of faith. Sometimes, the hardest thing you decide to do involves having full faith in yourself. I’m currently the sole owner of Devil’s Milk (but of course I ask my husband for feedback and help). I’ve always held down a full time job along with running a company on the side, and this time I’m not. I am throwing my entire being into this company, and it’s actually harder than maintaining it on the side along with having a day job, Read more>>

Julie Greene

People in the business and creative world talk a lot about taking risks. Things like, putting yourself out there, getting outside your comfort zone and fake it till you make it permeate the vernacular. While all those are true, I think the biggest risk you can take is NOT doing those things. Read more>>

Emmanuel Guarino

My wife and I had great jobs that paid us well and had us traveling around the country. We were teaching on how to start assisted living homes and it was a lot of fun. We had been working at this company for around 7 years at the time when my father the CEO of the company suddenly passed away. Read more>>

Cindy Gardner

The most significant risk of my career was choosing to make Swing Dance my full-time profession. I had always wanted to work in music and dance, but didn’t know what it would look like or how I’d get there. At first I just followed opportunities came my way, and right up until the point of making the transition into a profession I felt like Swing Dance was “just a hobby” regardless of the amount of work I had put into it. Read more>>

Latribia Brown

As a private chef, taking risks can be both exciting and challenging. Here are some tips to help you take calculated risks in your career: 1. Know your clients – Before taking any risks, make sure you have a good understanding of your clients’ likes and dislikes, dietary restrictions, and expectations. This will help you avoid making any decisions that may not be well received. Read more>>

Sherell Mckamey

I took the risk of becoming a small business owner not knowing if I would succeed or fail .It’s like everything else in life it has it’s good days and bad .Sometimes I want to quit because sales are slow or it just isn’t cutting it .But I love doing it I can’t just quit even if I am only making stuff for myself or family for gifts I love wood working .People think that your a business owner you get to do anything you want and call the shots ,to some extent yes but it’s a lot of work and you win some and loose some money ,customers, friends , battles …etc. Read more>>

benjamin starks stewart

After working for a Mobile Cell Company, I constantly keep seeing my time fly by, and I was building someone else dream I became frustrated and hated the policies & politics, that never seemed to help protect the working guy, there was an incident that happened, and that partnership ended, I was determined not to find myself in that position again, so I became a gambler, Read more>>

Woody Sylvain

I got into boxing around 2015 when my wife wanted to try it. I eventually took to the sport and started training as well. Some time passed and I eventually started helping my coach train fighters. Fast forward to 2018, I was working full time, training, and helping my coach train his amateur fighters. My father in law was recently diagnosed with cancer and I began to help my wife take care of her father. Read more>>