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.

Chelsea Knowles, MS, CCC-SLP/ RMIII

Chelsea said, “If I had not have fallen off of that skateboard, I may not have taken the risk to step outside of my comfort zone to start my private practice!” Here’s more: Chelsea’s entrepreneurial story began In 2017, when she was skateboarding with some friends, tried out a new board, and fell, breaking her wrist. Due to lifting restrictions at the Pediatric Outpatient Hospital where she worked in Miami, she had to take 6 weeks off from her busy job. She had space in her schedule for the first time in a long while. Read more>>

Stevey Jackson

I wanna say the biggest risk I’ve ever took was quitting my job months back to pursue my modeling, acting, and social media content creating career full time. The reason why I say this is because, around that time before I quit my job I was having a hard time there. There were some things going on between me and management and it got to a point where it was effecting my work ethic & mental health. As I was contemplating on leaving this job after a incident between me and my ex manager that led me to leave the work place after clocking in for only 2-3 minutes, I was already getting signs from God to leave the job. Read more>>

Ruth LaGue

Does risk mean failure? It’s a question I often ask myself and the answer I continue to come to is this; risk is the process of reframing an outcome. For example, in my day job as a user experience designer, I’m happy to fail, because I learn something from users about my designs which will make their experience better. So yeah, I happily fail and keep failing until the product is just right for the user. Read more>>

Jamilah Pollard

I’ve decided after more than 20 years of vacillating to share my gifts as a writer with the world. On the surface this may not seem like a huge deal but at the root is the story of a girl who grew up painfully insecure. I felt most myself by myself, my refuge was often found in alone time. There was no pretense, no judgment, no shame, no critique, just my thoughts, my joy, my tears, my laughter, my heartache. It was in these moments I learned a ton about myself and humanity. How we’re so afraid of literally everything our lives can morph into a complete mess of a thing, and we’ll watch it burn because we’re too afraid to say stop, no, go, next, stay. Read more>>

Lauren Romero

I never envisioned myself as a business owner or risk taker, until life guided me in that direction. Prior to starting my own business, I had a great job at a worldwide travel magazine with tons of perks. In November 2019, we were all required to attend a mandatory call which lead to everyone being laid off due to the magazine ending. I was 7 months pregnant with my daughter and just heard I no longer had a job. Although everyone in the room was terrified, I was weirdly relieved. I knew I needed more- more passion, more risks, more challenges. Read more>>

Dr. Akshata Prabhu

I have been a professional model since 2002. I have had the opportunity to model for multinational brands like Loreal, Smirn Off, be featured in about 14 prestigious National Magazines & Newspapers in India like Times of India, Bombay Times, Indian Express, New Woman and many more. Apart from being a popular & published model, I have had the opportunity to be a host & interviewer on Indian National Television for 3 Shows and feature in Top Charbusting Music Albums as the lead. After having an amazing stint with my professional career in the field of fashion, media and glamour, I decided to quit my modelling career in 2008 for academic enrichment. Read more>>

Marya Nguyen

Starting my web design business was a huge risk! I had just decided I wanted to go freelance and do something in social media after working with small digital marketing agencies. And before I knew it, I lost my first client because the covid-19 lockdown happened and I just pivoted into web design. Suddenly, like millions of people, I was left trying to cope with how to pay for my bills as well as just cope with what was going to happen to life as we knew it. Read more>>

Sarah Casey

Taking a risk is the only way you were going to stand out! Stepping out of your comfort zone and pushing yourself to the next level shows you that you can do things that you did not know you could do. I have been a make up artist for 10 years, I took a break when I became my mom to spend time with my children, but I would still freelance on the side. A few years ago a photographer approached me and wanted to do a theatrical shoot with me… We did a half body skeleton and I had never done body painting before. Read more>>

Abbey Smith

There have been a ton of risks I took in order to be where I am today, but I realized I’d rather take those risks than be unhappy with a life I would be living without them. Between moving across the country on nothing, getting myself through school, and engraving my passions into career, they certainly paid off. But it was painful, it had its hiccups, and brought me to the lowest points in my life. Between speakeazie and being a leader at DreadXP, I don’t regret any of my struggles, I can’t allow myself to to keep pushing forward. Read more>>

Karmessa Padgett

My life-changing risk happened in 2018. About a week after auditioning, I received the news that I had been chosen to be one of American Idol’s, Ruben Studdard’s background singers for his “Ruben Sings Luther” tour. My ultimate goal has always been to center my career with music, particularly performing. This was literally a dream come true, a young, black woman from Mobile, AL being able to perform all over the country with an American Idol winner! So you KNOW I immediately typed a 2 week notice, relinquished my job as an Assistant Property Manager and began my full time journey in music. Read more>>

Shiesha Mozee

The biggest risk I’ve taken in business was to even start! A lot of people are afraid to follow their dreams and passion because of the risk and lack of support. I believe as for myself it starts with your mindset you have to believe in yourself and believe your craft or whatever it is that you do and if your passionate about it your more likely to follow that dream and be okay with the risk that comes along. Read more>>

Tyrus Ceo Daniel Pinckney

As entrepreneurs there’s no growth without taking risk. We took the biggest risk of our lives at the time by letting go the biggest blessing that has ever happened to us which is our brick and mortar and decided to go fully e-commerce. From the outside it may look crazy or like we may have failed but we do nothing without a plan. The plan was to target more people, create more revenue and also reach more people and the best way to do that nowadays is online. So to all the entrepreneurs out there we say take that risk and stand on it. Read more>>

Carita Fambro

The biggest risk I’ve taken so far, is taking the leap to put myself out there to share my content. And it wasn’t even starting the blog, it was putting myself “out there” (in social media land). I wasn’t a blogger overnight, there was about six months to one year that I was just sharing recipes on social media to friends and family. No reward, no brand deal, NATHAN and that was the most humbling experience for me. Creating recipes that I loved, taking basic pictures (up against real food photographers) and sharing them to my audience uncertain of the feedback I’d get. I felt the weight of what taking a risk like that was, but it has been the most rewarding. Read more>>

Kim Hix

Aug 8,2016. I walked out the door and away from a secure, yet unfulfilling 10 year job at a local Globo gym, and onto the best decision of my career. After being an employee for 10 years, observing what didn’t sit well with my heart in the health & fitness industry, owners concerned with sales and not people, my time was now to do it my way. Read more>>

Brittney Newton

So, where do I begin? In 2019 when I lost my job at Chrysler or in 2020 when my father passed away from Covid? Either way, both of these major life events led to me taking the biggest risk of my life. In the middle of my MBA program in April of 2019, I was fired from my job at Chrysler. Now let me tell you, I was devasted, you could even say heartbroken. This was my first big girl job out of college, and I was making a great living. At that time, I thought that 9 to 5 was my bread and butter. I believe this is when my journey with depression began. Read more>>

Edwennia Moore

Walking away from the one career I was most comfortable with in corporate America as a banker of over 15 years under my belt to open up my own business was one of the biggest, scariest risk I had ever took in my life. And now after 4 years I have no regrets of doing so even on my slowest months, closing down after a pandemic and not knowing how things would continue to flow. It’s a risk that I value Read more>>

Breanna Perry

At 32 years old, I decided to pivot out of my 6 year managed health care career into a mental health career working as a therapist. This was one of the greatest leaps of faith I had taken in my life because it would require me to quite my job to go back to school full time to obtain a 2nd master’s. I had been working since I was 14 and didn’t know what it would be like not to have steady income and I had promised myself that I’d never go back to school full time in undergrad! Read more>>

Dawn Quintana

I have been making soap since 1994 selling online and doing vendor events, lots of set up and tear down and long days. After a few years I started to get hotels and wedding favor companies asking if I would make favor and guest size soaps for them, it would mean making much more product per month than I had been, after much thought I decided to jump in and try it, I went from making 200 plus bars a month to almost 2,500 bars per month, with the help of family and friends a lot of blood, sweat and tears, but once I got a system down it worked, like a well oiled machine. Read more>>

Séydou

Ever since I was young, my hideaway from the world would be to create things other people couldn’t reach. I’ve always found magic in starting something from scratch or retelling a story that means so much to people. Starting a career in the arts is one of the most significant risks I have taken so far in my 21 years. The arts is a far-fetched dream when it comes to my family, and being able to break out and try it is a tremendous risk. When you love something so much, the risk of failure isn’t the scary part. The frightening part is wishing you would have taken the risk to pursue what you love. Read more>>

Don

The biggest risk I have taken was moving to Dallas moving. It was one of the hardest things that I could have ever done. I was 22 moving out of my home state New York; specifically The Bronx. I had some money saved up, but I knew that it would only last me so long and moving during COVID a lot of the opportunities I had not only as a creative, but as individual with a master’s degree in PR were removed for me because of the virus. Read more>>

Maria Filar

I left my corporate design job – what had once been my big dream job – to pursue a freelance career, that in turn led me to starting my own business designing products. I’d been at my office job for over 6 years and was really starting to feel stifled and burnt out. Creating designs for a large company and not seeing any of the reward was really starting to wear on me. In 2018, a day before my birthday, I left the job and never looked back. Read more>>

Rachel Sudduth

In 2021, I took the biggest leap of faith and risk of them all! I quit my job to focus on my creative adventures as a Spiritual Life Coach and Tarot Reader. I had a few bucks saved and I used it to invest in some tarot cards, some candles and some bracelets! I was amazed but the outflow of support from everyone. Friends, families and people I hadn’t spoke to since highschool were purchasing bracelets and booking tarot readings. Read more>>

Laura Thompson

When I decided to leave a salaried job in the restaurant industry to open up a 300 square foot space of my own that was a huge risk. Honestly, if I hadn’t had a partner to provide for me during that time I wouldn’t have been able to do it. Not taking a paycheck for almost two years, some of that during pandemic times to add more stress, made me think I was crazy for deciding to go out on my own. Read more>>

Meredith Corning

The biggest risk I took was a couple of years ago when I decided to completely stop accepting new wedding clients for my successful wedding planning business and switch course to start my own PR firm. It was 2020 and the event industry was facing many new challenges. I felt it was time for me to step back as a planner and utilize my public relations skills to help wedding industry businesses bounce back from the chaos of the moment. Indeed my first clients were fellow wedding vendors I had previously worked with as a planner and it all couldn’t have worked out better. Read more>>

Annie Truax-Dunn

Signing a lease on a new space for communal gatherings during the height of a pandemic! When I initially purchased our business from Hayley, the individual who first started the studio, it was Jan 2019 and there was only one year left on the lease, with option to renew for an additional year. I figured it was a very low-risk venture – if I found, after the course of a year, that the business wasn’t profitable or that owning a boutique fitness studio simply wasn’t for me, we had an “out” so to speak. Read more>>

Zeke Man

Everyday when we wake up we have decisions to make. From the clothes we wear to what we will be doing that day. We have the option of reinventing ourselves everyday if we wanted to. I personally like making those decisions and taking risks when it comes to my career, I believe I wouldn’t be where I am today if it wasn’t by taking risks. A little over 2 years ago, during the pandemic, I started an unexpected journey repairing guitars and equipment for friends and people referred to me. Read more>>

Natalie Preusser

In life, we are faced with choices and decisions everyday. Some easy, some not. Moving to Cincinnati at 18 years old from Youngstown OH was a risk. I was alone, broke & didn’t know what to expect. However, I was determined to make it work and push for my dreams. I didn’t expect to go into massage therapy and leaving UC to pursue massage school was a huge risk. I took it and I haven’t looked back since. Read more>>

Brandy Avenue

I have always believed that you have to create the life you want to live. You have to work at your goals, no matter the obstacles. I took my own advice last year, when I decided to start a coffee business. I wanted to combine my passion for coffee with my background in business management. I’d been successful in creating opportunities with my film production company and felt confident that selling coffee would be straight to the point with little complications. I was wrong. Read more>>

Lauren Thompson

I would never describe myself as a risk taker. I usually attribute that description to people who regularly take actions that are seen as reckless, short lived, and mostly for the thrill of it. I prefer to think of myself as a person who dabbles in the unconventional. But when I really think about it, most of the highlights of my journey through life have all been the result of taking risks. Importantly, risks that have gone well. Read more>>

Brittney Young

When I first decided to start my own catering and private chef business, I had a job. In fact, I had two jobs and was going to school part-time. I was making pretty good money, saving money and making some plans for the future. Deep down inside of me, I knew that working for someone else wasn’t my future. I knew early on that I wanted to have my own business. One day I had a deep prayer to God, to say the least, and I asked for direction. Read more>>

Penny

The world is fully saturated with talent. Our phones give us access to millions upon millions of people who have a craft and want to share that craft with the world. Today, the biggest people in our industry all have one thing in common: they stand out. Which is what I have set out to do. Being primarily a writer for so long, I always envisioned the hurdles and obstacles that I would face heading into artistry. I thought that if I went for it, who would listen? Who would care? Read more>>

Tierra Lynn Hester

She has taken many risks her entire life. She was a “kitchen beautician” and underage in a state where braiders had to have cosmetology licenses. She spent many years, throughout middle and high school, braiding hair to be able to purchase necessities like: school clothes, shoes, food, pay her phone bill, feminine products, and more. She has always been self-sufficient, she just needed structure. Read more>>

Shelbi Aiona

Opening Black Box Creative felt like one of the biggest risks I’ve ever taken! When I moved to Austin, I started working toward finding a permanent Pole Instructor position. I found VAMPS Dance and scored a position as a seasonal instructor. Eventually, I fell in love with the studio, the community, and the life. I worked incredibly hard at teaching as much as I could and developing my skills for sharing knowledge. Read more>>

Sauce Papi

My entire life has been centered around taking risks, whether they have been financial or life altering. The most recent risk I’ve taken was in 2019 when I quit my 9 to 5 to fully pursue my music career without any distractions. It began beautiful with finding myself with having nothing but time on my hands to work on my craft. I started to dive right into my passion and even managed to make some celebrity connections with artists such as Mike Will Made-It and Slim Jxmmi. Read more>>

Jack Babel

Starting a business especially in the heat of COVID was a huge risk. It really just started out as a hobby and turned into something much more. We soon created a community of like minded people in the greater Nashville area. Whether it’s vending or throwing shows, pop ups or just being at events we make it a point to change the game even if it seems out of place. I dropped pretty much everything to get badworld going and we’re still in the early stages but I can confidently say it was well worth it:) Read more>>

Rafa Tarin

ive always been a maker – a creator, a builder, an experimenter, a cook, a crafter, a trash picker, a mess maker – someone who takes various materials and turns them into something else. an alchemist maybe. a rasquachero definitely. being an artist is/was always how i saw myself even if i didn’t know exactly what that meant in a day-to-day way. Read more>>

Tami Kress

The studio was just two years old when two professors from UNCG Department of Professions in Deafness approached me about doing an ASL shadowed production. I had never even heard of a shadowed production or had any understanding of how it would work. I really respected the women who asked me to consider it and I loved the inclusive concept of it, so I said yes. It has been a life changing decision for me and for the studio. In a shadowed production, the ASL interpreters are brought on to the stage and become part of the cast. They create the characters with the actors and help move the story forward. It is an amazing art form, and I am proud we do it at Studio 1! Read more>>

Melvin Stakely Jr.

My whole career has been me taking a risk or risks to achieve goals or progress in life. It was the summer of 2008 when I made up my mind to take the right risk. Not the typical risks I was accustomed to like selling dope for basic needs of survival, or risking my freedom by stealing what I did not have to make it day to day,… I mean the type of risks that can only benefit all involved and not one sided. I played high-school and Junior college football, had I not dropped out due to financial issues a would have earned a scholarship. Read more>>

The Suit Of Swords Daniel Ramirez

One of my biggest risks taken was fully investing myself into my art when I didn’t really have the confidence in me at the moment, I think it truly is something I see a lot of people experience and endure, there’s always the risk of failure but there’s also the risk of success. This goes back to when I was still a teenager right out of school and deciding that living in my car and making art would somehow one day lead me to a success path in art and in life. Read more>>

Jasmin’e Gentry

Starting business a few months prior to Covid 19 shutting the world Down completely, was a roller coaster. Fearing that I would have to close due to not being able to afford being shut down, I decided to take my last $200 and put it towards buying product to make soaps and other cosmetics for the skin. I had only 4 products on my line and with all the down time I had, I knew I needed to research, learn and prefect some more recipes. I took the entire time to put everything into my business literally my last and now we are upto 56 different soaps, oils, scrubs, Shea butters and more! I went from shipping 5 orders a month to shipping about 40 every week, Read more>>