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.
Melanie Webb
I used to say that I knew what I’d accomplished working for others and now it was time to take the risk to believe in myself. But I no longer see pursuing my own path as a risk. In fact, the way I see it, it’s riskier to put all my eggs in the basket of another employer! Going into the pandemic of 2020 I’d already been “sitting the bench,” as I like to call it, for about 8 months. I’d had two mTBI’s (that stands for mild traumatic brain injury, aka ‘concussion’) within a month of each other, and I had my hands full with a far-reaching and complicated healing process. Read more>>
Bianca Stephens
Risk taking is the tool to propel you to your purpose. Without it, you will never touch your potential. Risk taking takes you out of your comfort zone, building new muscles (figurative) that you never knew existed.
I had to step out of my comfort zone and fall off the cliff to greater heights. The opportunity arose for me to be a vendor at a mental health summit. I have never done this before. I was nervous just thinking about it. However, I knew I had to use the nervous energy to rise to the occasion. My teammate had to travel to a new state that had no current clientele. I had to remove any shyness and meet new potential clients and expand the brand in new territory. I had to show up as the expert in my field. Read More>>
Dagmara Loftus
For me there were 2 different moments that changed the way my career unfolded. In both of these situations I had to take the risk. The first breakthrough moment for me happened right in the midst of Covid. Unfortunately the Wellness industry has been greatly impacted by the Pandemic and I had lost my job at the Ayurvedic Wellness Center that I worked at that time. The place ended up not making it ( – so sad) and it gave me to push to pursue my dreams and start my own practice. Read more>>
Nicole Wallace
My name is Nicole Wallace and the risk I took was betting on myself and opening my own mental health counseling private practice. In January 2021, I resigned from my position as a school counselor and took the leap to open my own private practice. This was both scary and exciting for me. As a person of African American/Puerto Rican descent, mental health is not very prominent in our communities. Read more>>
Elle Collins
Becoming an entrepreneur with NO income, savings, or connections has to be the biggest financial risk one could ever take. Here my husband (Mounir Collins AKA Mo) & I were at the beginning of the 2020 pandemic crisis…Unemployed, Stuck, & Stressed out. We had both been laid off by our jobs trying to figure out how we were going to survive with our then two-year-old. Right before the pandemic had struck, I started working at a marketing agency assisting the owner and learning the ends & outs of digital marketing. Read more>>
Kenzel Fallen
Both of our co-founders came from professional careers that focused on risk management with Tio being a Mechanical Engineer in the Oil & Gas industry and Kenzel being a Corporate Risk Manager in the Banking industry. This weighed heavily in our perspective of risk-taking as we understand risk is not always negative but rather should be balanced and calculated against the level of return expected. Risk can be healthy and risk can be positive and some individuals or business have a greater appetite for risk than others. Read more>>
Eli Boyer
Anytime you start something like a band it’s gonna be risky no matter what. When we started talking about forming a band we were in the middle of a worldwide pandemic and we never thought we would be able to actually form the band. Lucky for us things died down and in the summer of 2021 Washington Avenue was formed. Read more>>
Kamilah Martin
In 2020, with the world feeling turned upside down, I resigned from an organization whose lived values no longer aligned with mine. I took a risk as the primary breadwinner for my family of four, and I bet on myself, leaning into my passions and purpose. I started Katalyst and have had the fortune of partnering with and consulting for organizations and foundations around the country. Read more>>
Brandi Holder
I often call myself a reluctant solopreneur. That’s because up until my mid-thirties, I couldn’t see a pathway to success other than working in corporate America. I had been working in multifamily property management for about ten years when I met my late husband. The hours were long, and the demands were many. One evening, he told me he didn’t understand why I was investing so much in someone’s business when I could put that energy into my own business. Read more>>
Kim Duffy Rachel Miklya
We took a massive leap of faith last November after leaving our full-time jobs, with benefits, to start our own business from scratch. Neither of us had much knowledge of running our own business so the last year has been an amazing, yet anxiety-provoking, learning experience. Prior to launching Strength in Nutrition, we worked together in a large, level one trauma hospital for 8 years. Rachel worked in the medical intensive care unit while Kim covered the hospital-based cancer center. Read more>>
Andrea Guerra
We decided to open Balloons by Jolie in Austin because there was not any store who supplied biodegradable high-quality balloons in the area. I started in the balloon world by working for a balloon store in Houston, were I got a lot of knowledge on how to operate a store like this. Starting with a new company, in a new place were nobody knew us was very scary, but we decided to take the risk; and it was the best decision of our lives. Read more>>
Tristan “Art”
As an entrepreneur I think there are many risks taken but for me personally I think the biggest risk I took was sacrificing my 20’s to chase a dream with no clear destination. There’s no direct path you can take as an artist to make people love your work. I didn’t grow up rich so I’m making a conscience effort to make sure my kids have that luxury. When I do have them. That’s truly the way to pay it forward in my opinion. Read more>>
Charishetta Hart
Opening a storefront doing a pandemic.. Read more>>
Nachaye (Pep) Blanks
One of the biggest risks you can take is chasing your dreams….. Sometimes we hold ourselves back because we are not sure what the outcome will be, or we are scared of trying something new. Me on the other hand, I craved to try something new. I am coming from Detroit, MI to Dallas, TX….that was a extreme decision especially with a 3 year old baby girl! Read more>>
Shannon Payne.
I started my photography business when I was on maternity leave with my 2nd son. I have my Masters degree in teaching, but once I became a mom I lost my passion for education. My husband talked me into getting a nice camera after our son was born, and my love for baby photography was born. I learned how to use my camera by taking photos of my 3 month old, and before I knew it friends were asking me to take photos of their kids. The next thing I knew, my bank was asking me if I was running a business and suggested that I open a separate business checking account. Read more>>
Danielle Graves
I quit my six-figure job – twice! I was fresh off an exotic vacation to the U.S. Virgin Islands celebrating milestone birthdays with loved ones. It was a long overdue break that I needed and, apparently, I came back with more clarity than I bargained for. It was at a time in my career when the weight of leadership and what it took to show up every day and excel in an organization that was not my own became too heavy. Read more>>
T.J. Cornwall
People have always labeled me as a dreamer. When I was younger, I took this as a compliment, but as I grew older, I stressed about becoming the old man who never went after his dreams. I experienced true analysis paralysis as I pondered what to do with my life. It got to the point where it was affecting people around me and my mental health was at an all time low. My friends were saying, “I miss the TEEJ from five years ago.” Read more>>
Jason Johnston.
Back in 2009 (26 years old) I had gotten to a place in my life that I had done all of things I was told were good or needed to do as an adult and found being an adult wasn’t as exciting as I told it would be. I had an adult job, I was debit free, about to be engaged and surround with lots of great friends but found a void in my life to do more. I wasn’t content with what I was told was successful, I needed to do more with my life and help others as much as possible. Read more>>
Mo The Model
I took a risk on myself when i was 18, that little did i know would change to whole course of my life. I got an offer to audition for a modeling and acting school, and at the time modeling was not even something i was interested in doing. I was a freshman in college and i didn’t know exactly what i wanted to do with my life. I was confused on what i wanted to do in this world. I swallowed my nervousness and went to the audition and they loved me! I was accepted into the school and took my 8 month course to get my diploma and Graduated with modeling and acting training. Read more>>
Brittneye
The biggest risk I ever took was thinking anything other than Plan A was an option, taking “no” as the end all be all answer, and allowing the opinions and fears of others to manifest within my psyche. You may think these scenarios aren’t risks. Or maybe you were expecting something along the lines of investing in a industry-first business venture, but no. I took a risk of not betting on myself. But, I had to shake that mess off. Read more>>
Kimberly Parkman
While I design most of the handmade jewelry that I sell, there are a few items that I have to have parts made by an outside vendor. This step in the process adds a 2- to sometimes 3-week turnaround time for these items. While my customers are very patient, I like to make and ship orders in a more timely manner. In addition, I have so many ideas for jewelry designs but the creation time from start to finish can take weeks, sometimes months, if I’m not happy with the sample and need to have the design tweaked and a new sample sent out. Read more>>
Darrin Miller
Stepping into music is a risky business… for some people, it becomes all risk and no business, and there’s definitely a lot of money that goes into producing music long before you ever see a return… IF you see a return. But, I didn’t start making music for money, I started making music because I was driven by purpose. I started writing music in 2016, shortly after teaching myself guitar. I had never sung before, music wasn’t a hobby, or even much of an interest until then, but I had been serving full-time as a pastor and figured that learning the guitar would be helpful in case I need to lead worship occasionally. Read more>>
Kailee Marie
One of the biggest risks I have ever taken is being self employed and going full time with the business I started at 19 years old. I was midway through college, taking 5 classes, working an internship, working a part time job, managing my business, and photographing weddings every weekend. After graduating from college, I knew photographing weddings was where my heart wanted to be. Read more>>
Patty Hillkirk
When I look at this question about “taking a risk” I reframe it as a question about “following a dream.” In 1995, I had the dream of creating a therapeutic community for children coping with HIV/AIDS. My journey began with my volunteer work with adults living with HIV/AIDS in 1987. Around that time, I learned that my best friend was diagnosed with HIV. I wanted to learn more about the disease, and I became an HIV/AIDS educator with the Red Cross. This led me to serve as a volunteer therapist for seven years with an organization serving adults living, and dying, with HIV/AIDS. Read more>>
Paul Childers
The ability to take a risk is the definition of creativity. Being creative in any way, shape, or form is always going to be risky business. That’s what makes it so intoxicating to people like me. When you have an idea or you have something that only you can say, you risk being ridiculed, pilloried, and criticized. Read more>>
Leah Morgan
Prior to becoming a business owner, I worked in 2 different industries. I was in radio advertising sales and then pharmaceutical sales. I opened my first yoga studio with a partner while still employed full time. After realizing that would be too much to juggle, I left my corporate job to work on the studio full time. This was a massive risk, as the business was not yet profitable. Read more>>
JEROME WHITAKER
When you got money , you have to learn to take the L “You can lose more money by try making a point then just taking a L” It’s a risk most aren’t prepared to take .. A learning experience in losing or just taking the L & starting over As a brand CEO , we must learn to Lose to be successful in some cases – we can pin point to some songs I create or videographer where I had to showcase my losing experience to be able to say ..I had to go through this to get here. Read more>>
Derrick Collins
I took a risk when i left the safety of a corporate job and backing to starting my own practice. I went for it, and now i’m here. Read more>>
Joe Michaels
I say I’m not really a risk taker, but I think my history would say otherwise. As far back as I can remember I’ve always been a fan of extreme sports and participated in them on some level since I was in my early teens. So yeah, I suppose I am a risk taker. One of the biggest risks I took in life was opening my own chiropractic practice. I had gone to school to become a chiropractic physician and worked for a doctor up in the mountains of Colorado. Read more>>
Toi Sweeney
I took a huge risk 5 years ago leaving my corporate job as a styled director at the worlds largest shopping net work QVC. I left and started The Well Dressed Brand. It was very scary and I had not plan on leaving my job for another 4 years. I spent 16 years at that job. I had no saving no real plan but I jumped. Today I have written a bestselling book.
Secrets of A Well Dressed Brand. And I have the pleasure of working with some of the most incredible C-suite executives. Read more>>
Natalie Deering
I am a person that typically takes very little risk in my decision making. I am a first born and usually follow the “rules” of life. So when I was faced with the realization that a part of me was no longer feeling fulfilled in my full-time 8-4:30pm job, it took me a while to pause and listen. The pandemic forced me to look at this part of me that wasn’t feeling in alignment with my purpose at that point in my life. I had given birth to my first child in January 2020, and was soon faced with the major life changes of motherhood and a pandemic. Read more>>
Maranda Johnson
A big risk I have taken since becoming a business owner is getting into a contract with a huge storefront in New York City called Flying Solo. Flying Solo is a business located in Soho New York that allows other small businesses to sell their products or merchandise out of their store front and online store. Was I scared? Of course I was. Here I am all the way in Georgia shipping hundreds of dollars worth of products to another state that I had never even stepped foot in allowing others to be in control of my business an money.. Read more>>
Desiree Jones
Prior to what I do now, I used to work part-time at Home Depot as a Garden waterer from 5am-9am. At that time, I decided to move out my parents house with little to no money and no car. In order to get to work I used to take a Lyft, but Lyft was so expensive I couldn’t afford that either so I had to think of another way that I could get to work. Read more>>
Justin Jenkins
At the age of 19, I was living with my grandfather and working 9-5 at McDonald’s, making beats, songs, and working extremely hard, so I started praying and talking to God, asking him to show me the way. So he used my mother, and she informed me of a position, and a higher paying job, overseas. I was afraid of losing everything, including my surroundings and the people I was with, and I realized that I wasn’t missing out on anything because I did everything that a normal adolescent would do, so I finally got tired of working so hard for $800 every two weeks and told my mother that I’m ready to grow up and make me and her proud, Read more>>
Lindsay Love.
My biggest risk was starting my practice, TherapyLuv, PLLC. I was working at a large community behavioral health clinic as a clinical manager and I would tell my peers that I never wanted to start a practice. The idea was scary to me and owning a business seemed complicated and confusing for me. I started my practice in 2020, during the height of COVID like everyone else. I felt underappreciated in my job and I wanted better. Read more>>
Kristian Gilmore
When I think about all the times I wanted to play safe I realized that not only was I holding myself back but, I was letting others do the same. All the creative work I’m mass producing now is about challenge and edge within myself. When I started podcasting it was about a year and some months ago and I wanted to go to therapy again but couldn’t afford it. As my thoughts and anxiety kept banging around in my head I kept questioning what would make me feel better in the mean time? Read more>>
Will & Jorge Garcia-Kesler
We decided to start a food truck in the midst of the COVID-19 pandemic. We were married right before everything shut down. We were working from home and after a while felt that we needed something to do together. Jorge has worked in and managed kitchens and I have always wanted to open some kind of bakery. We came up with this idea for a breakfast food truck. After a lot of researching we were told it was a bad time to start a business because of the pandemic and that generally, “restaurant” business take forever to turn a profit. Read more>>
Erlee
I think the biggest and craziest risk that I have taken is moving to California during the pandemic with no job no real place to stay and no real plan other than to make my dreams a reality. Having the pure motivation of knowing that even though the situation at the time seemed insane I knew that it was gonna work out for the better. I just knew in my mind that this was what I needed to do to further my career and to really light a fire under myself to achieve these goals. Two years later and I don’t regret my decision at all it was extremely difficult and at times seemed impossible but I wouldn’t trade the experience for anything in the world Read more>>
Tavious Peters
I come from a family of educators, military and just school oriented people. I’ve always had a love for the arts but didn’t go after it as a child because I felt I had to do what family did and that was to go to school. Once I got to a point and on my own I decided I’m going after my dream of acting and modeling, the entire entertainment career. It’s been difficult but it has paid off. Sacrifices are definitely inevitable but hard work and dedication makes it worth the hard times. I’ve been on some tv shows/movies, campaigns for big brands and continuously striving for more every day. Keep the faith and don’t let anyone stop you from going after your dreams Read more>>
Kyree Hamlett
Recently, I moved out of my hometown to explore all of my opportunities in fashion. Frustrated with lack of resources time after time, i decided to move and start over. I was once told “Everything you’re looking for is right outside your comfort zone”, and I can say after moving that statement is very true. Read more>>
Jettana Okoye, LCSW, NBC-HC
Taking six months off of work for maternity leave has been the biggest risk I’ve taken in my business thus far. You might be thinking, “maternity leave isn’t (or shouldn’t) be considered a risk”. However, when you live in America, happen to be a woman, Black, and a solopreneur that relies on consistent work…The amount of time you’re off can end with the closing of your business, a decline in income, or decreased clientele. Read more>>
Alma Fernanda Regalado
The biggest risk I’ve taken by far is changing my business model and going 100% online. Prior to march 2020, my business consisted of in person cooking classes. I had a minimum of one per day and was basically fully booked. Everything was going great and I LOVED every minute of it. Come march 2020 and with it tons of uncertainty and no chance of having in person events, especially not food related ones. Read more>>
Ellie Curry
It was the beginning of my personal development journey. I had worked all throughout college looking to land a job in my major (fashion merchandising). After graduating I finally achieved what I had been working toward, I was hired as an assistant buyer for a well-known fashion company. I thought that landing this job was going to solve all my problems. That it would give me the confidence I was craving. Instead, I ended up spiraling. I wasn’t performing well at my job, I was struggling with loneliness, and eventually, I fell into a depression. Read more>>
Charles Tyson
I think the biggest risk was when I moved to Houston Texas. I’m originally from New Haven Connecticut and at times i use to have a feeling of fear. This fear came from not knowing how my career was gonna go? As an artist, it’s tough to make a name for yourself but sometimes you have to move away from your comfort zone to make things happen. With any risk you take you gave to be smart with it. Never take a risk without thinking about positive and negative outcomes. Read more>>
Kamryn Murphy
I took a huge risk, when I decided to move away from home. I’m from a small town in south Louisiana called Amite. I’ve lived in Louisiana my whole life and even went to college in Ruston, Louisiana at Louisiana Tech University. When I graduated from college in 2022, I decided to leave everything I’d ever known and move to Nashville, TN to pursue my career as an artist / singer-songwriter. Upon moving, I had no job lined up, no upcoming performances, I didn’t even have a band together, nor did I know any musicians at the time to even reach out to. I moved into an apartment connected to a family’s home in the Franklin, TN area. Read more>>
Julie & Grant Schultz
When we decided to purchase Costas Candies in 2009 it was a life changing decision for us. Julie was currently a stay-at-home mom, with the intent to go back to teaching someday after our babies were in school and Grant was in the construction field working with his dad’s business, in line to be the 3rd generation owner of Schultz Homes. It was 2009 and the US was in the middle of a recession. Costas was in need of new owners with a vision and a heart to bring the business up to its full potential. Read more>>
Bilan Joseph
Six years ago, after graduating with my doctorate of education and delivering my third child, I knew that my family and I had outgrown our home. My husband and I, in the small town that we had adored raising our children in, had outgrown any opportunities that would financially take our family to the next level. As a woman of faith, I felt a strong desire to pack up our three-bedroom starter home and set off to greener pastures. Read more>>
Sixman
Big risk I took was at the beginning of this year. I planned and booked a 3 day cultural experience in the city of Grand Rapids, Mi called Return of the BoomBap. A major saying used for a lot of overseas hiphop shows and festivals. I coordinated the “Industry Mixer” held at “Wasted Clothing headquarters” where we had two live Djs playing music, industry influencers, Artist and business types networking in the room. Which is not always the easiest thing in a city filled with a lot of hate for others. Read more>>
Christopher Missimo
Law school was one of the biggest risks I’ve ever taken. In 2020, amidst the pandemic, at age 28, with a thriving and full therapy practice and a second practice about to launch, I began law school at Texas A&M School of Law. I already completed seven years of college education across two degrees in five years, eradicated $80,000 of student loan debt, and yet I was about to put life on pause to pursue one of the most difficult academic endeavors. Read more>>