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.

Michelle Le

I was working a 9-5 job from home and although it gave me a little freedom of not having to be in the office, I felt so depressed and drained doing something that I wasn’t happy doing. I knew that I did not want to work a 9-5 job forever. My boyfriend played a big part in making me realize that sometimes you just have to go out there and do something out of your comfort zone! It’s a scary ride not knowing what the outcome is whether it’s going to be good or bad but it’s the best feeling once you see your work come to life. Read more>>

Kara Ottinger

“Oh, you’re an Art student… what type of job will you get with that degree? I guess you could always teach.” This is where the “risk-taking” started for me. Although I’ve never been the one to adhere to the status quo, I did ponder a few times if I was making the right decision for my future. I even second-guessed it while gaining an Associate’s degree. Crazy that we are supposed to have our future figured out by the time we are 18 and decide on a major. This is one bit of advice I always pass on to my student assistants and younger family/friends. Take the risk! Do what you love, be whoever you want right now… the rest will figure itself out. Read more>>

Malaysia Evans

As far as taking risks, I’m an adventurer at heart, so risk-taking is kind of my thing! However, I wouldn’t be human if I said I didn’t have fears and insecurities to face with every risk I’ve taken. The most life-empowering risk I’ve taken is making the decision to pursue my dreams of being a fashion designer full-fledge. Talk about facing fears and pressure! I knew I had something great to offer the world, but I had to push past the thoughts of what everyone else would think. Read more>>

Janeisha Mays

When I think about my entrepreneurial journey, it all seems very risky. I remember in college telling my boyfriend, “entrepreneurship is your thing, not mine. I plan to climb the corporate ladder and be the CNO of a hospital.” Tell God your plans and watch him laugh! When I decided to go into nursing entrepreneurship, I honestly didn’t think it all through. I knew that I didn’t want to be a bedside nurse forever and I knew that if I wanted to walk away from it, I had to have something else to do with my life. Read more>>

Bethany Carlson

Getting into the Real Estate world in and of itself is taking a huge risk. In most circumstances, you leave the security of a 9-5 job with regular paychecks and benefits, and dive into a world of ever changing market factors, and dependence on you and only you for providing for yourself. In retrospect, I was always excited for an element of risk, whether that be riding the biggest roller coaster at an amusement park, or studying abroad for a semester in college. Read more>>

Amanda Iwu

After graduating from college, I knew I was not ready to say goodbye to the dreams and goals I had set for myself. Coming from a West African immigrant family, it was taboo to be anything other than something in the medical field, lawyer, or engineer. I have always been fascinated with the beauty industry and everything it encompasses. Anytime I tried to do something else, I always found my way back to beauty. It was a risk stepping out from a cushy, stable opportunity into the realm of entrepreneurship, Read more>>

Titus Haug

Risk goes hand in had with pursuing a dream. It seems that all things that are worth while take a lot of time, investment and hard work to obtain and maintain. That goes for relationships, growing plants and food or in this case, creating art and making a living from that. For me my passion in music led me to a point where I realized I would need to front some serious cash in order to make my first record. I was young and broke, so I decided to do a Kickstarter which was both a vulnerable and scary thing to do. Read more>>

George Paul Knapp

Before I first started my journey into the insufferable void that is freelancing, I was just a guy with a dream that one day; I would be able to make a living doing what I love. Having that mentality is a risk in and of itself, becoming a full-time filmmaker is about as unrealistic as being an astronaut. But, to a bold few, it may seem feasible enough to pursue. I would like to think of myself as one of those bold few. It has been 5 years since I started this journey, and it’s paid off (so far) beautifully. Read more>>

Kimberly Lee-Okonya

I have taken many risks in my life. I have always been of the mind that we have one life to live so do what it is you want, even if you have to do it afraid! But if I had to discuss just one of the biggest risks I’ve ever taken it would be when I decided to leave corporate America and move full time into entrepreneurship. When this move happened, to be honest it was not 100% planned. Long story short there was an imbalance in life. Read more>>

Chloe Shanice

The biggest risk I took in life was deciding to move to a new city with my husband and start a new career in the esthetics industry. Trusting God and knowing that I was moving according to his will was my biggest motivator. I am originally from West Palm Beach, FL, born and raised. During the pandemic my husband and I made the choice to move to Tampa, FL in order to experience a new environment and culture. Tampa is so diverse and there were so many opportunities for small businesses to showcase what they do and offer. So we took a leap of faith and moved. Read more>>

Venessa Abram

After losing my brother to suicide and almost losing myself, I embarked on a journey of self-discovery. While doing this, it became more and more evident that services providing assistance and resources to victims of suicide and suicide survivors were in serious demand and I saw a demand that needed to be filled. Fueled by my own experiences and a desire to make a difference, I started SDp3 to raise awareness on mental health and suicide prevention and partner with key players in the industry to achieve that goal. However, when starting out, the organization was new and small, it was just me, and as such, we weren’t receiving any external funding. Read more>>

Daishaya Gadson

Immediately after I got off my deathbed, I took a risk by starting nursing school. Returning to school with a new onset of uncontrollable seizures may have been a poor judgment of timing. However, adopting a victim mentality or putting my dreams on hold was not an option. Pursuing a career in nursing was a big life-changing decision for me after a recent pulmonary embolism and multiple fractures. I always wanted to be a nurse ever since I was a child. At first, it was just my calling , then it became my purpose, and there was no getting away from it after experiencing both sides of the bed. Read more>>

Danielle Fewings

Going into business with a partner is and has been the biggest risk we’ve taken. Jason and I came from different backgrounds, me having run a business independently for many years and he had a very full time job. We came together through one idea and built from there. It took a lot of trust and willingness to get to know each others strengths and weaknesses in order to fully be able to work together. We had to be committed to building each others strengths up and pushing each other work through areas of growth opportunities. Read more>>

Kenzie Perez

The biggest risk I’ve taken so far was opening Fresh Cosmetic Studio. I opened in May 2021, so the pandemic was a factor, but also Austin was having an influx of people moving here making prices increase on almost everything. Previous to opening my studio, I was a cosmetic tattooer working in tattoo shops around Austin. I wanted to create a studio that Austin hadn’t seen before, where all are welcomed and we serve the best permanent make up and lash extensions in the city. Read more>>

krista nerestant

I’ve taken multiple risks beginning from when I was 17 years old in the verge of graduating Belleville High School NJ while also receiving a cosmetology license to risk it all; say no to a college education and instead pursue my entrepreneurial dream to become a salon owner. That required defying the elders in my traditional Filipino family whose desires were to have the younger generation be all college bound and academically driven offsprings. So when my college counselor called to ask if I was ever going to show up for my classes, I said. “No, I will be learning all about the beauty industry instead and open a salon. I cannot do that if i’m not focused at a 100%.” Read more>>

MRK SX

After serving 13 years in the US Air Force, I left to pursue a career in music. I was living in Tokyo, Japan at the time, and had been producing music for major label artists there for the 2 years prior. After finding out that people would pay me well for doing what I loved, I could see no other pathway for my life. I had a wife and child at the time, so I was definitely putting them in financial harms way. I bet on me, and ultimately moved back to America in 2007. Read more>>

Annette Licitra

A few of the biggest risks I’ve ever taken in my adult life were leaving my corporate finance position after nearly 15 years to start my own business, and at the same time, making some drastic changes to my diet and lifestyle. This happened for a few different reasons. I was not passionate about the corporate life or the positions that I held, and I was super stressed out. I was very tired, fatigued, and my stomach was in knots more days than not. I was starting to feel and see the emotional stress manifest as physical discomfort, and honestly, it scared me. I didn’t want to live this way for the rest of my life. Read more>>

Nelson Cardenas

I have always expressed that there are two things in my life I can do without any fear art and cooking. Mainly with art I take lots of risks, I don’t follow the conventional rules I create my own canvasses in unusual shapes and forms, I paint with fire, I use a welder to draw on metal sheets, a belt sander to create indentations on wood, I make strings from leather scraps to resemble hair or a mustache, sponges to smooth out large surfaces with paint, polishing tools to create texture, Oh! and let’s not forget the usual artist brushes. Read more>>

Destinee Love Sanchez

I have been a single mom if 2 boys for 13 years. I have absolutely no family near and raising them and running a household with one parent has been challenging and exhausting! I was working full time for an appliance company doing accounting work for very little money. There was no opportunity to move up or make more money so if I stayed, that would be my future. I knew I had to make a change and I went home and wrote out what I would need to do in order to quit my job and I realized it was very doable. Read more>>

Anthony Wilson Jr

Taking risks could sometimes mean pain will be involved. I’ve taken many risk stepping out of my comfort zone to pursue music. Many people told me I shouldn’t do it because I was already good at something else. What they didn’t know was, I’ve always wanted to be a singer since I was a little boy. Stepping away from a job I’ve been doing for over 15 years was something I didn’t want to do but it’s something I had to do in order to pursue my passion! Read more>>

Aisha Mae Bada

In 2020 I started a Handwoven Filipino Bag business to showcase my culture in Miami. It was a huge surprise how quickly it got accepted. I was going to various pop up events, farmers markets, store openings, fashion shows, photoshoots back to back. I was doing all these while handling social media, our website and packing and shipping orders by myself. It grew more than what I expected in just a few short months. I was ready to scale. Read more>>

Alysa Kowis

Leaving my 9-5 corporate job of 13 years to follow my passion! For sure my most considerable risk. The corporate job I had for over a decade never made me happy, but I was good at it. When I got married, my husband and I decided to put his career building first since he had a clear path he wanted to follow. So, I was the stable steady income for such a long time! We both saw my burnout hitting hard, and how it was impacting my mental health and every aspect of our lives, so we jumped.  Read more>>

Claudine Miles

In 2018, I was an Assistant Principal at a high performing Middle School in Atlanta. I deeply loved my work, my community, and the people I was lucky enough to serve. At this particular time though I was really struggling in my motherhood journey my son bounced into the terrible 2’s and was giving my husband and I the business and at the time he was in a daycare where I had to make special arrangements to drop him off at 5:30 AM. Read more>>

Sophie Arnold

When I first thought about the idea of becoming a cosmetologist I always had a preconceived Notion that I could never do it. I was influenced growing up in the Instagram era seeing tons of talented people post their beauty “art”. I constantly was comparing myself to them because I felt like I could never create some of the looks they were creating. Read more>>

Uri Redler

The most significant risk I took was moving my life entirely to a different country. When I decided to invest and study in Miami, I didn’t grasp the magnitude of my decision, and I just went for it. I usually say that Im not a fan of getting out of my comfort zone, but I find myself out of that zone many times. Read more>>

Mariah Frisella

I had what most envied. I had a successful and decorated nursing career of 11 years. I was well respected by my patients, peers, and providers. I had dedicated the last 15 years of my life to serving others in the best way I possibly could when I was faced with the biggest decision of my life. In 2021, I was faced with losing my job or taking something I didn’t feel comfortable with. I realized that sticking to my convictions meant risking it all and putting my career, pay, reputation all on the line. I ultimately chose to stay true to my beliefs and ended up losing my job because of that. Read more>>

Taylor Luna

I recently quit my full time job to pursue art fully! I remember waking up realizing that I’m just not happy anymore, don’t get me wrong my job was cool I got to work around awesome people all the time and got paid pretty well but I wasn’t happy. One day I finally had enough and needed a change in pace. I decided I would contact a local artist and ask to be an assistant working along side him to create wonderful art. Honestly best move I ever made! Taking that risk was scary as hell yea but now everyday is a new breath into life. Read more>>

Scherica Lockhart

Stepping into the music industry is definitely a risk. It requires financial investment into your projects, sacrifice of time away from your family, making good judgments in all areas and trusting the process. I didn’t want to accept the calling upon my life to pursue music. I was content with my life working in Corporate America, being a wife, mother and singing on the praise team. I had a rough time with a job in Corporate America and I felt like things became very difficult. Read more>>

Dr. Latoya Appleton

Taking a life-changing risk doesn’t always seem to be the best Idea in the moment. I found that the reward often outweighs the risk. I managed to finish a Doctoral degree while in the midst of a divorce and then launched a podcast “Black Girl, Say Something” to discuss my realizations to get to the point where I can speak freely and with peace. The most significant risk was finding my voice and not being afraid of judgment and moving from shame to healing from the pain. I manage to handle all of my adversities while running a Mobile and virtual Optical Top Notch Eyewear (topnotcheyes.com), being a mother and an advocate for women and infant nutrition. Read more>>

Dr. Genevieve Dobson

In 2006, I was working for a small company in Harrisburg, Pennsylvania in the student loan industry. I was asked to move to the Florida office and I jumped at the opportunity to move myself and my son to a state where we knew no one. After working for the company for 5 years it was time to jump into my own business. The company moved to Boston and I stayed in Florida. I took a job in Tampa in a similar industry but it was horrible. We were very poorly treated and knew I needed to make a move to working full-time in my business. Read more>>

Jenna Volpe

The most top-of-mind risk I’ve ever taken has to do with meeting the man who is now my husband, who basically ripped the rug out from under my entire life as I knew it up until that point in time. In 2017, on a whim, I had booked a trip to Toronto, Canada (from Boston, MA) to attend a class on metaphysical healing. (Booking the trip and attending the class were not the risk! Stay tuned.) Read more>>

Andy Wu

When I left my comfortable corporate finance job at Siemens to go into the private SFR sector, at the time, my friends & family thought I was crazy when I left such a promising career at a Fortune 50 company. Now looking back, that was one of the best decisions I have ever made. I have learned a lot and made a lot of good connections since then. Read more>>

Diana Cordoba

I started my business; Simply Blue when I was 17 years old in the state of Indiana. I built an amazing clientele, great connections with other vendors in the wedding industry and was doing very well. But I was not happy being in Indiana, so I randomly decided to move across the country from Indiana to Orlando, Florida with my best friend. It was the SCARIEST decision of my life. I knew I was taking a big risk leaving my business behind, and starting all over, but I needed to do this. Read more>>

Kaili Spear

The biggest risk thus far has to be the time I decided to invest in my very first vehicle and first apartment in October 2021. I knew soon after I graduated college from the University of Tennessee at Chattanooga that I would need to have saved up enough money to move into my first apartment and purchase my first vehicle. I graduated December 2020 with a Major in Communications and a Minor in Psychology. I wasn’t really sure what I wanted to do with the degree but I knew I wanted to be able to invest more into my personal self-taught business. Read more>>

Jhonny Puttini

I have been working in the pro wrestling business for 15 years, not only as a referee, but also as promoter, manager, and I even founded my own federation here in Italy. I basically did all I could do here, I achieve all I could here. I found my self wanting to do more, I always had the dream to work as referee overseas and maybe move in USA, the land of big opportunities. So I decided to take a big risk, I quit my job, sold my car, took a plane and went to America for a 2 months long wrestling tour. Read more>>

Mishawn Costen

After giving many years of myself to the corporate world, I had decided it was time for me to put more effort towards my true passion in creative arts. It wasn’t until my grandmother had become severely ill during the pandemic and I needed to step away from my 9-to-5 to visit her. That dreadful time came when the company I had been working for was going through some transitions and needed all hand on deck. Read more>>

Tilda Boyd

Risk can always be scary to take but could be amazing at the same time. I used to have a 9-5 job but wasn’t necessarily happy with it. I took a risk to start my own business, my clothing brand business. It’s probably the best decision I’ve made so far. When you can work for yourself doing exactly what you love is the best feeling in the world. I design and make clothes for a living. Read more>>

Coach Roxy

I worked in law firms as a legal assistant for many years and I worked in radio for a short time as a newscaster. All of my life I sang and wrote music part-time. I also travelled with local bands and started advising other singers and creating performances. When companies began to layoff and I went from job to job I also began to have problem with my voice and later found out that I needed surgery. Read more>>

Lauren Holloway

A few years after I graduated college, I was stuck. I had obtained a Bachelor’s Degree in Film & Media Arts and started in the industry working at Golf Channel for 2 years until I was ultimately laid off along with the rest of my department. Shortly after, I started a job at HSN working on-call as an Assistant Producer, and after my 6 weeks of training would often work an 8-hour shift at Publix (a job I had since high school and kept throughout the years) and would make the commute to St. Pete and work a 10-hour overnight shift at HSN. Read more>>

Corey Hustle

Taking a risk!! Well I’ve spent most of my life working 9 to 5 jobs I’ve done retail,warehouse,construction etc..because of these jobs I was able to invest in music career plus pay bills & all that good stuff. I took the risk of leaving those jobs alone back in 2020 & I haven’t been back since. Read more>>

Karyn Rosenberg

When I started my private practice it was in the summer of 1999. In fact it was July 4th weekend. I was working for a local hospice at the time, and I knew I wanted to be “independent” for Independence Day! I was basically quitting my full time job in one fell swoop with salary and benefits to opening up a practice in Florida, in the summer, which used to be a relatively quiet season. Snow birds knew to get out of dodge in the heat of the summer! Read more>>

Courtney “Chikin” Patrick

As a kid all the way throughout my teenage years I was always drawing. I’d lost my drive and passion for creating shortly after graduating hs. About a decade later I found my love for creating again and it came back with a vengeance. I didn’t want to lose that fire but I had a problem. I was working a full time job that didn’t really leave much room for me to focus solely on art. After while I decided I was going to quit my job. Read more>>