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 Harris

The biggest risk I’ve taken is taking a chance on myself. Growing up in Kentucky, it felt like making a living out of a creative career was a shot in the dark and I felt irresponsible to pursue that field even though I knew it was what I loved. I felt like I needed to hide it as my primary interest until I could prove to my family that I would succeed, but I actually needed to prove it to myself. Read more>>

Elexis Vasquez

Taking risks and stepping outside of my comfort zone has brought me to the success I have today. Some of the first risks that come to mind when I think about what paved the way in my career is hopping on flights and traveling to other states to photograph people who reached out to me through social media. Having the opportunity to do things like that is such a huge blessing, but can also be scary as a young female traveling alone to meet strangers to photograph. Read more>>

Lydia Paulos

Being a professional musician is essentially entirely comprised of taking risks. For many of us, there is no safety net or sense of stability. Staring down an empty calendar, or a dwindling bank account is a familiar sight, and we learn pretty early on to be ok with that, or to simply leave the industry. So, finding one story of ‘taking a risk’ is likely pretty difficult for most artists, myself included. Read more>>

Tyler McMaster

Pursuing a career in music is an inherent risk; I am reminded of this every time I put myself out there in an attempt to make it BIG. My success is based on the opinion of others and those opinions, in the age of endless digital content, are often ambivalent. There are a million and one people who want the same dream as me, so how am I going to stand out in a crowd? I probably need to become a giant or something, I don’t know. Read more>>

Hannah Talbot

I put it all on the line. Everything I had, I risked it all. To fulfill my purpose, to execute my dream. And I would do it, again and again. I moved to Spokane, Washington from Seattle two years ago. Now if you know Washington well, you know Spokane has spent a few decades being Seattle’s less cool cousin. It gets a bad rap for not being as pretty, or as cultured/diverse. Read more>>

Dave Di Pietro

Filmmaking is a risk business. You are always dealing with other people’s money, aka the producers. You are always trying to minimize risks and make a profit for the investors, so you can begin to create an on-going partnership in creating new film projects. Read more>>

Devon McLeod

One of the risks I took when I started my practice was leaving my salaried job at an established practice. Despite not having any clients when I left, I knew that it was time to move on and build my own practice from the ground up. During those early days, I got a part-time job as a receptionist at a spa in New York City to support myself. I also taught 10 fitness classes a week. By following my intuition, I landed exactly where I was meant to be. Sometimes, my ego would come in with, “You should be further along by now.” Read more>>

Chloe Deery

I started my Permanent Makeup journey when I had nothing else going for me. I was in school but had no idea when and how I was going to use my degree. I came across Arch and Line and took a risk on taking a training that I had no clue if I would even enjoy doing…. I now have the best mentor ever and have worked at Arch and Line for close to 3 years now. I have met so many good people in my life that I will always remember. I continue making new bonds with my clients. Risks can have the best outcomes Read more>>

Lauren Snell

In 2018 I decided to step way out of my comfort zone and quit my profession as an Elementary School Teacher in order pursue my side hustle full-time, in a new city, on the other side of the country. Read more>>

Amelia Briggs

Throughout my career, I have found that it is necessary to take risks to move forward. The first risk I took was choosing to get a BFA in college. This felt so scary at the time, as I knew there was no clear job path upon graduation. The second risk I took was quitting my job at 25 and moving to a rural town in Michigan to pursue my work as an artist full-time for six months straight. Read more>>

Aron Turner

When I was 18 all of my friends from high school were filling out college applications, working on their college essays, I spent most of my senior year going to the recruiting station for the Marines. I woke up for school around 6am , had school, and then wrestling practice from 5-7 and then after school until 8pm. And on days I wasn’t at wresting practice, I was at the recruiting station from 5pm to 7pm. Most days were long and I understood the risk of going to the military. Read more>>

Santino Becerra

The biggest risk I took was when I decided to quit my job of 20 years to start my own business.. During the last year of working there I remember counting the days down. Some people were telling me what if your new business doesnt work? Do you think they will let you come back if it doesnt work? Even some close relatives and friends questioned this risk I was taking…. Read more>>

Doctor Reina Rodriguez-James,MD

I born and raised in El Salvador, I graduated as General Medicine and Surgeon Doctor in my country. Was an earthquake in 2000, at that time I already had my first daughter, and I was working in a small town. Due to the earthquake, I lost my job, my aunt offered me to help me here in USA for a few months. I accepted and came with my baby to EEUU. Here nothing was easy, I had to take care of my daughter (I was single mom) and work to provide and pay for my bills. Read more>>

Weatherly Stroh

The biggest risk I have taken is starting my business and becoming a full time painter. Before taking the plunge and dedicating myself to my art, I was teaching 4th grade. I was in the processor going through. divorce and knew that I needed to make some changes in my life, that I wasn’t following my true calling. I kind of blew up my whole life…I sold my house, was newly single and decided to give myself a year to paint and see where it led. Read more>>

Letticia Gilmore

Wow, taking a risk. At some in our lives we all take risks for something is important to us, something that has meaning, gives us purpose. If there was ever a time in my life that I took a risk, it was deciding to start Solid Ground Sports Academy 5 years ago. I’m not from Sacramento so nobody here really knew who I was. I had just started to get involved in the community. Read more>>

Fox Garza

Owning a business is “Taking a Risk”. It was definitely scary taking the leap and putting your savings into something exciting but also a bit of an unknown. I truly believe that you must risk to receive reward, so making sure it was an educated risk was very important. Also, having my partner, my boyfriend and best friend at the time, now husband ad father of my children, was a definitely a great support. Making sure we had a plan B and really made sure that we put in minimal to test our concept before we went full blow was key. Read more>>

Taijah Bell

When I reflect on the idea of taking risks, it reminds me of a pivotal moment in my life where I decided to step out on faith and bet on myself and my family, despite my fears. At that time, I was in a job within the school system that was mentally and emotionally taxing, and it didn’t align with my true purpose. However, I was skilled at what I did and earned a good income. Read more>>

Alona Sofer

Our names are Alona and David Sofer. Our story started back in 2016 when we decided to follow our hearts and pursue the “American Dream.” We moved in 2017 from Israel to Kansas with just our two dogs; Fender & Gibson. — The beginning was rough; entry level positions, cultural shock and loneliness sat at our doorstep. Read more>>

Taia Johnson

Take the risk. Yes, you read that right. Take it. Take it scared, take it unapologetically, take it. Why? Because it is exactly what you need to be exactly where you need to be. As an avid planner and someone who thrives off stability, I completely understand negotiating the pros and cons of decision making. But let me be clear, anyone who has a success story to share, has taken that one risk that propelled them on that road. Read more>>

Melissa McCall

As I’ve navigated my business, it’s become clear what’s been successful and what’s not. Working with young families, I see the importance of easy actionable items for literacy and children’s development. I’ve tried various approaches like literacy kits, in-person classes, mommy and me sessions, drop-off classes, and coaching, but I’ve learned that parents need simple, research-based literacy activities that don’t demand much of their time. Read more>>

Willow City

We first entered the entertainment industry in 2010 when Ezra was in his first film. Aside from having our childhood home published in books and magazines, we had never experienced what life was really like behind-the-scenes of a movie. We’d grown up in choir and taking piano lessons, but about the same time Ezra began acting we began performing music. It started out around the campfire; Read more>>

Ryan Picone

I think for me taking risks is a part of the musical journey. As a musician we are always faced with the idea of how we will make a living doing what we love, but in the end it seems like things always workout. It’s been almost 18 years doing nothing but musical endeavors and I feel fortunate to be able to make a living doing what I love. Read more>>

Apuroopa Kavikondala

The biggest risk I’ve taken in my life is publishing my first book. It was in COVID, and I honestly had so much time that I just wrote the first story that came to my mind. It was about an Indian girl who moved to America from India and how the difference in culture completely changed how she viewed herself, causing a spiral of deteriorating mental health. Read more>>

Dr. Chakika Williams, DNP

A risk I can remember like yesterday I have taken was “betting on myself”. To be specific, walking away from a six-figure job to bet on me as a business entrepreneur, despite having no background in owning a business. The driving factors behind this decision were the desire for time freedom and the importance of my children in my life. Read more>>

Tracey Schultz

As a teenager i lived in a small town in Arkansas. I was a rebellious child. My mother had threatened to send my to juvenile detention. I am never one to be boxed in so I devised a plan to escape I convinced my best friend to move to Detroit with me. That summer we hustled money to purchase one way tickets on the greyhound and we was D Town bound. Read more>>

Thomas Ng

Great question and Absolutely! The Biggest Risk I’ve ever taken was when I decided to quit my corporate job to follow my dream to be a Spiritual Self Love Coach and start my Self Love apparel company, Affirm Your Transformation. I was 6 years in at the corporate job when I finally pulled the trigger and submitted my resignation. Read more>>

Stacey Kohl

My life changed when I decided to become a personal trainer. I was in the best shape of my life at the age of 50 and my friends and family kept telling me to start training people professionally. I was working out with my friends for fun at the gym for a while and never considered doing it as a profession. The idea of studying or taking a test, especially on muscles, bones, or anything to do with biology scared me to death. The risk of failing would be so embarrassing. Read more>>

Ieema Copeland

The biggest risk is the leap I took to pursue my dreams. My mom always taught me to keep a job at young age. Hollister, Jamba Juice, Enterprise, and 24hr fitness were all the 9-5’s I worked at before I took my final jump. I noticed my pay checks just weren’t doable for the lifestyle I wanted, or my needs to be completly honest. I would make five hundred dollars every two weeks (if that) because I would call out so often for auditions. Read more>>

Connor Frost

I left my full-time teaching career in 2012 to better position myself to pursue my music. This decision, scary as it was, propelled me to releasing 8 albums over a decade, touring the country and internationally, and launching my dream songwriting mentoring business. After I left my job, I picked up some tutoring work to make ends meet, and moved into a $460/month bedroom in Jersey City. That’s when things really started to happen. Read more>>

emily rich

at this point, it feels like risk & i are close relatives lol. i’ll speak on my most recent significant risk. in may of last year, i had to make a decision on whether i wanted to sign a new lease, or move out of my apartment.. moving out meant i’d be jumping into the unknown bc i only had one month to decide & i had no plan whatsoever. although, i had been craving change for a long time. Read more>>

Bungalow

For me, taking a risk is going outside of yourself and creating something that is beautiful in its own way. You never know where the outcome of that risk will take you so just trust your skills and the process. Read more>>

Laryssa Birdaeye

I started music a little later in life, though it had always been a passion of mine. I had started writing music at 14, singing basically when I could talk, and putting songs together in high school. I was terrified of sharing any of it with people, but there was always a little voice in the back of my head that urged me to pursue it. At 25, I was working a corporate finance job, wearing stilettos to work and hating every day of it. Read more>>

Tia Lee

In January 2019, I decided to take a leap of faith. It was a hard decision because people knew me as an event planner and editor, mostly. What I was about to venture into made sense to the people closest to me, but for everyone else, it was different. I would create a place where corporate women could become their best selves and do this by adding value through coaching. I made flyers and put them up in coffee shops. I sent out invitations to friends and family. Read more>>

John Patinella

The “known” feels safer, more familiar and usually has a level of consistency that provides comfort. Going all-in, head-first into the “unknown” for something you love is utterly terrifying. That fear of taking a major risk also comes with an excitement of future possibilities, but it’s hard to think everything will work out when you pack up everything you own into a U-Haul and drive across the country to move from Baltimore, Maryland to Hollywood, California to pursue music, not knowing anyone. Read more>>

Daisha Agboola

I took a significant risk when I decided to turn my passion for natural and beneficial products into an online business. With little knowledge of how to start or sell products to others, I invested all the money I had into buying materials, ingredients, and new gadgets. At the time, I wasn’t sure if this venture was realistic or if people would trust and buy my products. Read more>>

Ryan Chisesi

Starting my own business. Fully committing and leaving the “security” I had prior and going all in on my skill sets was a huge risk. But I would choose it again every time. You learn so much from running your own business. More specifically you learn more about yourself than just business. Read more>>

Stacy Cook

About one year ago my husband and I sold our 2800 square foot home to move into out 19′ camper and move to another state. We bought a piece of property site unseen. The property had no water or septic. The only thing we knew about the property was it had a small cabin, a shed, and a large pole barn. The property also had electric and seemed to have a good cell phone signal. Read more>>

Lauren Cooley

My business originally started as a side hustle, which is common story for many of us small business owners, especially of the creative sorts. I have a BA and an MA in Psychology so was working with kids and families doing job training for homeless youth, providing educational advocacy for youth in foster care and then onto dropout and truancy prevention in the public school system. Read more>>

Terri Morgan, Sarah Mathis-Luesmann N/A

Terri: I basically stumbled into this business. Needing specialty fabric for my sewing business (Fancy Pants 4 pets) and my resource was closing, I was not finding other good options cost wise. I discovered that I could have my own chosen designs printed myself. I had another person join in the ordering for her own sewing business of custom made cloth baby diaper.s We quickly realized what a good price point this was and wondered if others would also want to buy. Read more>>

Michelle Barzallo

If you had told me two decades ago that I would transition careers and transform my graphic design hobby into a thriving business, I would have chuckled and dismissed it as wishful thinking. You see, back in high school, I set my sights on the medical field, aspiring to become a Forensic Pathologist. While I did achieve significant milestones, being the first in my family to graduate high school, college, and pursue an advanced degree as an M.H.S. Read more>>

Maria Palacio

Taking risks is an inherent part of any transformative journey, and in my case, leaving behind a stable fashion job in New York to embark on a mission to rebuild the coffee supply chain was a decision fueled by passion, purpose and an unwavering belief in the potential for positive change. Read more>>

Joey Bartlett

I don’t perceive ‘risk’ as something negative; in my opinion, comfort leads to stagnation. The biggest risk I have taken is leaving my permanent job in 2020 before the pandemic affected the world. This decision was necessary as I was tired of complaining about the lack of preservation regarding Trinbagonian culture. As a result, my book ‘There’s Something Strange Happening in Talparo’ was birthed, focusing on Caribbean folklore. Read more>>

Kenielle Jefferies

My first loc client was my brother. 12 years ago he asked my mom to start his locs, but he did not like the parting style. He asked me to redo his grid pattern the same as box braids. At that time, I didn’t know how to comb coil. I started his locs with two strand twists and maintained them for several years. I also started and maintained locs for some of my family. I began to gain clientele from word of mouth in my hometown. I continued doing all styles, but realized I only enjoyed retwisting locs. Read more>>

Drew Newman

Back in 2021 I was filming an award winning short film called “Blackout” while simultaneously going through a break up. So everything that comes with a break up was happening, having to move out with no where to go, the back and forth, all of that. So yes that means while I’m on set, these were things I was dealing with, where are me and my daughter going to go, can I make this acting thing work faster? Read more>>

Matthew Stanners

The story of a leap into faith. February 2021, Austin Texas was hit with an anomalous ice storm. For five days the ground was covered in over two inches of ice, water mains burst and electricity was out for 90% of the city. I had expected to spend the week as I normally do, working remotely from home for the development company that brought me to Austin after graduating from Wharton. Read more>>

Jshauntae Marshall

On March 19, 2019 my life changed forever. Waking up to death threats against the lives of black children at my son’s high school and then to see his photo pictured as 1 of 9 targets on social media captioning the most hateful and derogatory words towards black children I had every seen in my life. While, this should have invoked fear, it had the opposite affect and ignited a spark that lit a match, which became the blaze of civil rights in education across Nevada. Read more>>

T’aira Flint

Taking a risk is an integral part of any business venture, and I’d like to share the story of how I made a daring decision to purchase a SheShed for my wellness and beauty services. In 2021, I noticed a growing trend among women who were transforming their SheSheds into salons, especially in the wake of the COVID-19 pandemic. Witnessing their creativity and resourcefulness inspired me, as I struggled to find an affordable space to perform my services. Read more>>

Dr. Lulu

3wks ago I decided to take a break from social media. A much-needed 3 wk break I might add. For those who didn’t know, I lost not one or two, but 4 members of my “family circle”, During that time, I did a lot of thinking: thinking about the meaning of all the loss and how I could help my clients through it. Read more>>

Camara Feagins

From a young age I always played it safe when it came to my career. I started working in the mortgage industry in 2004, and that become comfortable to me. I always had dreams of owning my own business. In 2022 I was laid off because the mortgage industry wasn’t the best at that time I was unable to find another job. I took this time find myself. Read more>>