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.
Mimi Alexa
I took a very big risk by leaving my job a week before my son birthday, jobs always give you stability because you know exactly what date you are getting your paycheck. Being an entrepreneur you don’t really know what is going to happen but you know that this is your purpose and you are going to do everything in your power to make it work. When I worked at my last job I literally was missing out on clients all day long because I was at work from 10am-6pm , now that I quit my job I am able to go all the way with my business and I couldn’t be happier. Read more>>
Hannah Linder
Even though it was my dream since early teenage years to design book covers for publishing houses, I did not seriously pursue this path right out of high school. Instead, I worked locally and took graphic design college classes from home—all still very uncertain how/when/if I could someday make my dream job happen. Read more>>
Darrion Nimrod
When I was 18, I started my journey in entrepreneurship. I had no idea how even to run a business, if I’m being honest. When I started, I was working at a local radio station. When that partnership ended, I moved to a different radio station to continue my journey. When I started to feel unfulfilled, I began to branch out and tried to find my own capture outsiders’ true identity without being under someone else’s umbrella. I got offered an opportunity to speak in Pittsburgh, so I grabbed my team and drove 18 hours in a snowstorm to do so. Read more>>
Brittany Ha-Nguyen
The biggest risk I’ve taken was very recent when I decided to leave my 9-5 job and pursue my own business as a photographer and videographer. It was definitely a difficult choice to make, but I knew deep in my heart that if I never tried to do it, I would end up regretting it later on. It took me months of going back and forth until I was finally able to make a decision that I felt at peace with. Through the process of trying to choose what path to take, I had the most incredible support system who encouraged me to take a leap of faith. Read more>>
Ethan Elalouf
Wow, where do I even start. Throughout my entire life, I was always considered the risk taker of the family. With countless broken bones and dozens of stitches to prove it. However to me, I have only taken one risk in my entire life. Post college, I was living in Denver working a 9-5, living the so called “dream”. Every day was worse than the last and I was beginning to lose the joy that used to come so easy to me. One day, at one of the lowest points of my life, I called up my Mom and essentially told her that I hate everything that I’m doing. Read more>>
Ben Young
After college, I was living and performing magic in Knoxville, TN. In 2015, I was attending a magic convention in the tourist town of Pigeon Forge, TN. While there, I met Murray Sawchuck, a magician from Las Vegas who has his own show on the famous Las Vegas Strip, countless TV appearances, and a huge online following on Youtube and Facebook. Read more>>
Stacy Skolnik
As a dancer my entire life, the biggest risk I took was packing the bags up and trying out the Big Apple. At the time, I was with a company from North Carolina where it was project base. Not the most stable way to keep a salary. Therefore, I knew I had to find another way to make income. It was only then natural that I become a Pilates Instructor. It has truly changed the way my body operates and so fulfilling. New York can be a challenge as you are pretty much a little fish in a HUGE pond. Read more>>
Saint Sergy
One of the biggest risk I took and currently living at this moment in time, is becoming who I am now, “SANTI” Saint Sergy. I was 17 when I decided to drop out of my senior year of high school to pursue my career in arts. I could’ve gone to college, gone to a trades school or just focus on a job but that never felt right with me, I knew I was destined to become something much greater than regular, I knew I was destined for this. Read more>>
Maria Davis
There’s a lot of risks a person will take. In my case, it was reaching out to other producers that had a similar sound to me. Most of the time I never heard anything back, and sometimes I would be told no for one reason or another. I was about to give up on the idea of collaborating until I decided to contact one more person. I was listening to Pandora one day and a song came on by the artist, 7and5. Read more>>
Mario Canon
One of the biggest risks Ive ever took was putting my job I had for 6 years after recently being promoted. I was an assistant manager at cellphone company. I was working full time plus overtime and pursuing my music career. I had recently gotten into fitness as well so for the past couple years I had been sculpting my body. I was exceptionally well at my job so I had a lot of repeat customers. One of them owned a gym franchise and told me I was wasting my talents celling phones and I should work for myself being a persona trainer. Read more>>
Taquasia Holmes
Knowing when to hold and when to fold. During COVID-19, no one knew what was around the corner as it pertains to employment; lay-offs, reduction in hours, and business closures were like second nature during this time. When I decided to go out on my own, I had a full-time job, benefits, and all the perks that came with it including the feeling of hopelessness from being trapped in an unhappy relationship with work. Read more>>
Rucha Muley
I was born and raised in Mumbai. Since the age of three, I would draw everywhere and on everything. In high school, I lost a textbook at school. My father went to the lost and found and immediately identified my book from the pile. It was the one with elaborate doodles on every page. That story reminds me how drawing was almost my way of communication. My family consists majorly of engineers and doctors. They didn’t perceive art as a lucrative career option. Read more>>
Jennifer DaSilva
I was doing very well in my career, but I had just lost my mom. I was five years sober and was looking to purchase my own home. I looked at several different houses in the DFW area. I was walking out the front door of the last house that I looked at and noticed something compelling. Keep in mind, I was getting frustrated and wanted to give up on the house hunt and had said out loud in my car “God, or mom, whoever, help me know what the right decision will be”. Read more>>
Nancy Kaul
What is your destiny? How does grace move through you? What does love ask of you? It is said that when you invite the grace of Hanuman, the knower of all hearts, into your life, the obstacles on your path will be removed, and his divine energy will lead you to your destiny. I’ve always been drawn to Hanuman, the ideal devotee: a symbol of strength, perseverance, loyalty, and devotion. Hanuman can be called to teach us the unlimited power that resides within. Through resilience and compassion, we conquer adversity and come out stronger. Read more>>
Jeffrey McKenna
It doesn’t matter what industry you’re in – there’s always some risk, competition, drama, and reward. Being in the fishing world is really no different! There is an amazing network of people who are supportive and awesome, but unfortunately, there is a small number of people who are not. I felt like I was moving forward with most, learning and growing in the industry but felt the need to take the risk and separate myself from those critics. Read more>>
Leticia Reed
I believe life is filled with risk taking moments. I have taken risks large and small all of my life. While most avoid risks, risk provides me with an adrenaline rush and make me feel vibrant and alive. Risks are important in that they truly define who we are and what we are truly made us. As humans, it’s naturally to desires a road map for every step we take and with risk taking that is definitely not the case as life itself is unpredictable and comprised of many twists, turn, hills, valleys and even desert moments. Read more>>
Vincent Orsolini
Being a full time musician and entrepreneur comes with a variety of unknowns. It truly isn’t a straight path or really definable in any way. As an artist you kinda navigate these mysterious waters in an ever changing music industry, working with different personalities, taking chances and grabbing each opportunity that is either thrown at you last minute at your previous gig or something you have been wanting to do for the longest time. Read more>>
Kym Terribile
The biggest risk that I have ever taken is investing in myself and business. I knew for years that I wanted to work for myself and start a business. Read more>>
Jessica Baum
I feel like my whole life has been about taking risks and following my heart. I’ve done this with starting my own private practice, writing and publishing my book, Anxiously Attached: Becoming More Secure in Life and Love, starting a second sister business called Be Self-full, and truly putting myself out there every single day online. Somedays, I feel like putting my pants on and getting out of bed is also a risk. Read more>>
Vanessa Freeman
When I set out to become a psychologist, my plan was to work in higher education until I retired. Most of my experience has been working within the higher education system and I truly enjoyed working with college students as they figure out who they want to be in this world. I was especially excited to land my first job out of my doctoral program working to specifically support African American and Black students on a predominantly white campus. Read more>>
Jamie Impastato
I’m kind of impulsive, and acting on impulse is often viewed as something to avoid. But my impulsivity has been a character trait for as long as I can remember. Whether it was spending my only quarter in the gumball machine, cutting questionable bangs, or trying to adopt a third rescue dog, my impulses have driven some of the very best and some of the not-so-great ideas (like the bangs) that I’ve ever had. Read more>>
Luzelly Frias
It’s December 2020 and I am working in a hospital as the pandemic continues to wreak havoc through the world. At this time I had already had covid, recovered, and returned to work on a covid unit for 8 months. The weight of the losses and grief began to affect me immensely and by mid month I had decided that my plans to transition into my own business needed to happen sooner than I thought. On a whim I submit my resignation, gave myself a month before the transition to put some things in place and by February first I had my first client as a full time private practice therapist. Read more>>
Lorreen Pryor
When the pandemic hit I was a full time Legislative Employee who moonlighted as an Education Advocate to help families navigate the k-12 system. In 2021, much to my husband’s shock I decided to leave my 16 year career to embark on a journey to live out my heart-work full time. I had no plan in place to what doing this full time looked like, but I just knew that I would be more effective when I wasn’t limited in my movements or my ability to speak freely. Read more>>
Jade Dixon
You ever hear that saying, “When it feels scary to jump in, that is exactly when you should jump.” When I was working my 9-5, I would sit at my desk, look around the office and realize there was not one person’s life I wanted. Everyone was comfortable with their secured jobs. As for me, I felt there was more I could do outside of my job. Read more>>
Tessa Markle
My career path is not exactly traditional and certainly not linear. While supported by my representation team, my acting career is in my own hands. I run a film production company and podcast with my incredible business partner, but again, it’s all up to us. The arts are inherently risky. You never know when your next gig is coming unless you’re creating it for yourself, and even then, you have no idea if you will be a success. Read more>>
Kathryn Gilbert
I finally felt at home behind the chair when I made the move to Charlotte. I had worked in the Lake Norman area for the majority of my career. I got wind of some friends opening a local goods shop in the Midtown neighborhood, and they were looking for a stylist. There was a need for someone to help out a fellow stylist as she was going on maternity leave in June of that year. I weighed my options and decided in February of 2021 to work at two locations. Read more>>
Cara Czarnecki
Born and raised in Chicago, I decided at the age of 40 to move my family to CO. I grew up in Brookfield and later moved to the south side with my husband. There, we started a family and I went into private practice. I had developed a good network system there but something told me that I couldn’t grow in the ways I really needed to. I felt stifled. Like I needed to rip my way out of a box. My brother in law got a job opportunity in CO and he and my sister planned to leave quickly. Read more>>
Jourdan Taylor
The most important risks I’ve taken as an artist were the ones that were borne out of opportunities that I wasn’t sure I was qualified enough to take advantage of. I began DJing at 12 years old. As a child/early teen it was difficult to be taken seriously in professional circles. By my late teens I was frustrated that I had developed and polished my skills for years and had nothing to show for it. I believed that I was “good enough” to perform on stage – but realistically I had zero experience. Read more>>
Chase Busath
A big risk my wife and I took was to leave a cushy corporate job and go all in on our own businesses. It was scary at first to not have the stability, but just the thing we needed to light the fire under our butts and go all in. It was too easy to say to ourselves day after day “we’ll build the business tomorrow”, but now we push every day to grow and build and it’s super exciting. Read more>>
Yusuf Bayraktar
Most of us grew up in a way that our parents or the society used to tell us go to school, get a permanent job, pay taxes get married etc. But I never found this idea proper for myself. Life has more meanings for that. I’ve found myself that I needed to take risk for personel growth or for my business in order to grow and develop myself. ı did follow my instinct put my first business when I was 21. Read more>>
Clash
Right now, I am the only artist in my city (outside of thee Boss Dogg) in the Web3 Space and it has come with blessings and bull-. It all started with waking up one day feeling like the whole world was washed in some weird gray. Yet, I felt color. I got the opportunity to do a private event which I soon found was about to change my life. I met my new home I guess quite randomly. Gala Music. Because after I ripped the stage, I became a Gala Music artist. Now two releases deep I have felt the highs and lows of NFT Music. Read more>>
Jaime Allen
Starting a metaphysical business was a big risk almost 10 years ago. This is why I waited a couple years before actually pursuing this dream of mine. This line of work wasn’t seen as legitimate. Even now, as it becomes more mainstream, it is hard for some to see this as a legitimate line of work. When I decided to start my business, it was as though I was sticking my big toe in a pool of water. Testing it to see if it was going to be OK to dive in. Read more>>
Michaela Miller
In 2019, I was working a corporate marketing job for a major hotel brand in New York City. In July of that year, I gave birth to my first child. To say I loved my job until I had my daughter is an understatement. But once she entered my world, I started to see time in a whole new way. I saw time as the most valuable thing in the world! I couldn’t bare the long commute, the long hours, and the inability to get home quickly if my daughter needed me. I ached for a world where I didn’t have to be away from my baby. Read more>>