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.

Quinn Kirby

In March of 2022 I moved from my hometown of Grand Rapids, Michigan, to Pittsburgh, PA and took my photography business with me. I went from relying entirely on referrals from the clients I served and connections I built over several years to starting from the ground up. It’s been a challenge I’ve stared square in the eye, but it’s still a challenge, nonetheless. Read more>>

Kelsey Gordon

Interestingly enough, I am currently in the middle of taking a BIG risk. A pretty life changing risk. I recently left a gym that I have worked at for 4 years to pursue full time building my own training business and brand. Deciding to walk away from the certainty of a busy class (fitness) schedule and consistent client base to go all hands on in my business hasn’t been without much consideration. It’s been a lot of waiting for the perfect time and moment. That “in a perfect world” type of situation. Read more>>

Shelby and Rick John

When Rick and I first started our wedding photography business, we were both working full-time jobs during the week. Rick was working a sporadic schedule for a retail store and I was still in hospitality, with both of us always working weekends and nights. The thought had been on our minds to leave our jobs and do photography and videography full time, but that was a huge leap. Read more>>

Rachel Rodriguez

I had always worked a full-time job since 1994 up until 2018. I launched our business part-time in 2012, then I went full-time with our small business in April of 2018. It was a bit scary not knowing what the outcome would be. I was taking a big jump resigning from a full-time job that would give me a consistent and steady income. The real question was, would I be making the right decision? Would we be successful? The answer was…yes! Read more>>

Tracee Gadson

Before moving to Columbia, SC and deciding to really pursue my photography business, I worked full time as a graphic designer and photography assistant in Charleston, SC. I’d been in that position for five years until the economy went bad in 2009. The photographer that I’d worked for at the time had actually taken another job outside of photography and left me to run the studio. I went from working full-time to only working from home two days a week. Eventually, the photographer decided to close the studio and I was laid off. Read more>>

Rachel Grunn

My journey to where I am now is colored with lots of little risks and leaps of faith I took along the way. Some risks were “rolled ankle risks” – meaning they were about as dangerous as stepping on a loose rock, hoping it doesn’t rattle you off; perhaps the worst injury being a “rolled ankle” or bruised ego. Other risks were giant leaps across gaping crevasses, where much more serious outcomes were at stake. My “loose rock” risk was dropping out of college. Read more>>

Deryck Richardson

I’ve identified as an entrepreneur for most of my life, but early in my career it was because I had direct sales or network marketing opportunities that I was working on the side. I’ll never forget the first time I was able to “fire my boss.” I was working a Network Marketing business and had quickly surpassed my income at my corporate job (which was six figures). My wife thought I may have been a little crazy, but she trusted me and that support was big. Read more>>

Vanessa Veloz

I entered a season in my life choosing between following my passion and purpose verses society’s path of success. We all have the right to make choices in life but when the time presents itself for finalizing a decision, an uncomfortable feeling happens. I realized in the moment when I felt uncomfortable, the start of growth started for myself. I worked at a law firm for almost 2 years and felt super unfufilled day to day. Read more>>

Hannahcamille Thomas

Go big or go home, so they say. We all know relationships can take the speed route to get home, but at what cost. Opportunities in life come quite frequently but, to live in the land of dreams and opportunity is something different. I remember being seven months pregnant and only having one month left till I graduated with my bachelors in science for Entertainment of Business. I knew I needed to focus on having a healthy child so I took the risk and dropped out at school knowing that my measurements of success would never allow me to just give up. Read more>>

Heather Sportsman

As a HBCU grad, two older parents on a fixed income, I played it safe when I received my BA with honors from Southern University Agricultural and Mechanical College in Baton Rouge, Louisiana in 2010. I immediately went into teaching. I touched a lot of lives and a lot of people helped me. I am so blessed. I stopped creating my own artwork for 10 years and focused on teaching, then the pandemic hit. Everything changed. Everyone has heard about the Great Resignation I’m sure. Read more>>

Kate Duffy

Many of my business opportunities and successes have occurred as a result of taking risks. Risks are uncomfortable, because oftentimes it’s the unknown end result that can hold us back. In the past I’ve thought “will what I am setting out to do be successful?”, or “will people understand what I’m trying to create and express?” I’m a big believer in putting yourself out there, speaking out loud your goals and vision and taking the steps to move towards them. When I’ve done this, doors either open or close, and the intended path for me becomes obvious. Read more>>

Nina Pearsall

About 10 years ago, in upstate NY, I started my photography business. I’ve always had a passion for photography. I went through Nursing school and had my first child halfway through my second semester in college. Boy, it was rough but she was my motivation to be successful in life so I could always provide for her. I worked as an RN for many years while using her as my photo subject and perfecting my skills. Read more>>

Kayla Harbeitner

Changing careers to become a ceramic artist was a risk. I had been working as a freelance animator for around 5 years when I decided to switch gears. I had been doing pottery since I was 16 and decided that going full time made the most sense. I took an apprenticeship with Charlie Parker in St Petersburg, FL and it was definitely the best decision I made. I learned a lot about throwing techniques to create large pieces on the wheel as well as how to run a studio. Read more>>

Yana Benjamin

In the fall of late 2019, I saw an Adventure Wedding Academy workshop happening in the Austrian Alps with the fabulous Cat Ekkelboom White who specializes in elopements in mountainous landscapes. At that time, I was booking my own wedding clients, but I was also freelancing for a large national wedding photography company, doing 40+ weddings a year. I wasn’t working with my dream clients (the clients usually didn’t care about my style or approach), I didn’t work in inspiring locations, so it was only natural that I was completely burnt out and I had no love left to the photography business. Read more>>

Priscilla Cerdas

Through the risk of saying no to myself (repeatedly), I learned the importance of the risk of saying “yes” to myself. I had always considered myself to be the most low risk, “safety first!” person. I used to be genuinely ok with that. I received a lot of loving – and not so loving – teasing over the years for being such a cautious, responsible person. What I’ve learned now in almost 30 years of life, is that being too cautious is also a risk. Taking no risks can also mean silencing yourself. You know what living in silence for years will lead to? A really big SCREAM. Read more>>

Alli Privitt

I’ve always been a bite the apple, take the risk type of person. However, that realm and area in my life has only gotten bigger as I’ve gotten older. From growing up climbing all tallest trees, to bareback horseback riding, to water skiing, to rollercoaster riding, to trick downhill mountain skiing, to rock climbing, to cliff jumping, to glacier water snorkeling, to deep cave spelunking, to swimming with sharks, to canyoning down waterfalls, to marathon running, to starting a business, and to leaving a teaching career after 10 years, nothing compares to the risk I took when I decided to become a licensed skydiver. Read more>>

Andy Elliott

A creative risk that I’m proud of started in November of 2019, which was the inception of Man to Man Podcast. Like myself, there are so many people out there that love having a hobby or finding a passion project outside of their primary job to work on. I believe it challenges us to stay motivated and to also be more creative as people. Read more>>

Christina & Edward Sledge

We met during the first week of freshman year in high school. We dated for two years on and off in high school. After high school, Eddie enlisted in the U.S. Army, and I went to Temple University. We were apart for three and a half years in other relationships. During Christmas break in 1999, Eddie proposed on a whim, and we were married two months later with only fifty cents in our pockets. We took a leap of faith which was very risky. We knew each other, but we grew immensely in those years apart. We had faith in our union that it would all work out for the best to guide us and here we are 22 years later, happily married. Read more>>

Zach Adams

I’ve always liked photography, ever since high school really. (2004) I did it for a hobby for a long time until 2018. That’s when I decided to start taking it a little more seriously. Slowly started doing shoots for friends and family and kept growing. Then Covid happens… During this time I still had a 9-5 job so when the stay at home orders happened I was out of work for a while. I took this time to document everything around me. Parks closed. Business closed. Streets empty. The George Floyd protests. Everything! I posted them to my photography page on Facebook and they really started to gain some traction. Read more>>

Juliann Abecassis-Walsh

After the completion of my post graduate medical internship and board examinations, I was left with the scary reality that there are virtually zero drops on the market within this field of Traditional Chinese Medicine and Acupuncture. I had really only one option: I could start my own practice with no previous business experience and hope I could forge my way. Read more>>

Chelsea Cross

Painting is my first love. I received my first easel when I was 5. I can remember the first time I was given a paintbrush, and from then on, I would watch Bob Ross and pretend we were painting together. I continued to create art throughout my life. However, there were times I took a longer hiatus than I’d like to admit. In 2018, I had made the decision to move back to Ohio to be closer to family. Read more>>

Candace Collins Jordan

• Risk taking is something we’re really interested in and we’d love to hear the story of a risk you’ve taken.
Every job I’ve ever taken has been a risk and has usually turned out not quite as I imagined going in—both in good ways and bad ways. You really have to do your homework ahead of time but, even then, this won’t guarantee a positive result. I worked for Today’s Chicago Woman magazine, under publisher Sherren Leigh. I wrote dozens of stories and styled almost every cover. Read more>>

Aaryon Bird Williams

I’ve been a risk taker my entire life but I truly learned the power of taking risk as a pro athlete and artist—Both have challenged me to step outside of the box and live outside my comfort zone in order to achieve the level of success I wanted in Iceland as an athlete and in Atlanta as an artist. I came to be the best version of myself in both professions realizing my childhood dreams. Read more>>

Shadi Asad

During a time of uncertainty (Covid) I had a choice to make with a business partner/friend. Either I finish out college with some degree I’ll never use, or drop out and start a gym. Thankfully I chose the 2nd option because of all the doors and opportunities that came with opening a gym business. Read more>>

Portia Booker

In March of this year, I was working a job I dreaded. I’ve spent 15 years in the healthcare field, but after Covid, most positions in the administrative arena went remote. I am a social butterfly, the “work from home or remote train” picked me up by accident and held me for ransom. I used to spend an extra 30 minutes sitting on the porcelain stool (toilet) because I found more entertainment there than sitting at my desk in the dinning room. Read more>>

cyndi bulka

After nearly 15 years owning a popular Yoga studio I was itching for something new, interesting and challenging. I’ve always enjoyed learning and like to challenge myself because that makes life interesting and colorful. Not many people want to let go of a well established business that’s successful. I never stopped loving Yoga or my Yoga community. Yet I longed for more freedom with my time and my gut was telling me it was time for the next leg of my personal and professional journey. Read more>>

Anthony Perez

The biggest risk I’ve taken was going with holistic healing rather than the medical care with chemotherapy, removing my thyroid and being on medication for the rest of my life. I was raised playing sports and staying active. I was 27 when I was diagnosed with metastasis papillary carcinoma(stage 4 thyroid cancer) I feel like we should all take risks especially when you feel it in your gut,heart and soul. Read more>>

John Le

At the end of November I decided to take the biggest risk of my life. I quit my full time job to pursue custom apparel. With the small success I found over the summer of 2021 I found myself overwhelmed with all types of work. I started taking a few days off every week to try to tackle the backlog of orders I had from my business. I was working for my uncle at the time. He was very understanding and understood that my new business would require more of my time and attention. As time grew on I completely stopped working for my uncle and started diving head first into the industry. Read more>>

Keysa Smith

I had a dream of becoming a restaurant owner since I was little girl, but didn’t quite know how I would get there. I had some major setbacks, one while attending Mott Community College, I was arrested for distribution of marijuana with other family members and sentenced to 4 in half years in Federal Camp, upon my release I wanted to become the woman I was meant to be. I served on various boards, did many speaking events as I went back to school and finish my degree at U of Michigan/Flint. I also finished at Mott College as well,. Read more>>

Lindsay Giedl

Opening The Studio Athens during the pandemic was a huge risk. At the time, I (Lindsay Giedl) was living in Atlanta and looking to move back to Athens. I was in negotiations with a local dance studio that decided to close during this time. Coincidentally, Cathy Rumfelt was renting space at the same local dance studio for her business, Allegro Athens. Our mutual connection, Grace Bagwell Adams was looking to return to dance after being on maternity leave. Read more>>

Jewel The Gem

My life as a Radical Black Queer Woman involves everyday risk taking. One of the biggest risks I took was leaving my full time salary job as a Director in a non profit in New York City where I was abused, disrespected and underpaid. Leaving that job and moving across the country to be a full time entrepreneur doing what I loved was one of the best decisions i’ve ever made. It took a lot of spiritual guidance, community support and most importantly the belief that the time was now and that I could do it. Read more>>

Jason Tobias

Making the leap to pursue a career in the entertainment industry wasn’t something that anyone I’d known had ever done… and whenever you’re the ‘first’ in any respective journey within your tribe, be that family or friends – you’re filled with an immense amount of questions. How do I do this? Can I do this? What’s the best way to ‘begin’? Can anyone show or help me? …and on and on. Read more>>

Alison Stevenson

I developed my first roll of film as a teenager and knew instantly I’d found what I was meant to do. But the world around me said otherwise. Parents, guidance counselors and just about every adult in my life told me that making a career out of photography was impossible. “It’s too much of a risk” they’d say as they encouraged me to shift my career goals elsewhere. And so I did. Read more>>

Maverick Malone

Risk is a word that used to follow me around like a ghost. Every time I would be presented with an opportunity for growth or something that would push me out of my comfort zone, she would materialize from the back of my brain and quietly ask, “Now? Is this a good time?” I would always swat her away but the more I did, the deeper I was digging my own grave. Read more>>

Rachael Vrielynck

I am magical… or so I’ve been told. But the secret is that I’m not magic, I take risks by creating my own opportunities. One of the first instances of this that sets the foundation how I live my life now goes back to high school. It was my sophomore year in 2018 and I was taking all senior classes but the private school I went to wouldn’t allow me to graduate early. What did I do? Instead of wasting two more years taking filler classes, I moved out of state to Chicago and went to a community college. Read more>>

Mona Jhaveri

Perhaps the biggest risk I have ever taken was starting Music Beats Cancer, a charitable crowdfunding platform that supports innovative biotech startups and partners with independent artists to help raise funs and awareness. It was a risk at many levels. First, cancer charities typically support research in hopes of finding a “cure.” As a trained cancer researcher, I and others like me know that research does not end in cures. Research generates discoveries that then need to be advanced and translated for use in the clinic. Read more>>

Nyla McKraken

I moved across country during the beginning of COVID. I lived in Seattle, WA for 10 years and built my business there, but for me it was time to leave Seattle. I decided to take a few trips around the country to places I could better afford life and Baltimore had the right vibe. But I didn’t know anyone here. My move date was set for April 1st 2020 and then COVID hit. I ended up moving about two weeks early to make sure that I could get out of Washington and not get stuck in quarantine. I had found a job but I wasn’t able to start for three months after I moved. Read more>>

Mara Peverini

I think the biggest risk I took is deciding to pack my life at the age of 25, leave everything and everyone I knew in my country, Italy, and move to the United States. I have been dreaming of living in the States ever since I can remember. There are so many things to love in this country. One of them is the high diversity among the people living here. There is a place for everyone, it doesn’t matter what you look like, or the way you talk, or how different you can be… you have a place where you can feel yourself and where others embrace diversity, because they are different too. Read more>>

Willie Contraband

Well, it’s been a journey for sure. I moved to North Carolina in July of 2014 from New Jersey in hopes to start fresh and change my life from the negative environments I experienced in my previous timelines. 2014 was a really tough year. Everything in my life was falling apart from the people who I thought loved me to financial situations and even regarding my own personal identity in terms of who I believed myself to be was changing. Looking back it was a time of complete rebirth and what I thought my life was had to die in order for the new to come. Read more>>

Marco Aguirre

I think the time I decided to start my production company, Soul Prophet Productions. I just had a falling out with business partner and friend. I wasn’t sure where to go or what to do. Then I remembered I had this script I finished and a love for this industry. I decided to produce the short script into a short film called “Umbra” I was scared to ask people to help me out with this project. But I asked for help and got it. Read more>>

Emma Gullo

Risk taking is one of the biggest necessities of being in the entertainment industry. You constantly need to be pushing your boundaries, trying new things, and overall just be unafraid to put your whole self on display. My biggest risk I’ve taken so far for my career is relocating – I recently left my home state of Georgia and moved to the infamous music city, Nashville, Tennessee. Read more>>

Ben Gardner

In 2021, I was 8 months into running business and everything was moving fairly steady. I found the opportunity to be a vendor and Pumpkinfest in Franklin, TN and decided to look into it. From what I read, 100,000 people come from all across the state of Tennessee to attend this festival. I thought having exposure to a new client base and that amount of people would help grow my business. I decided to apply to be a vendor and the costs associated were far higher than I was accustomed to. Read more>>

Angel Laketa Moore

My entire career has been risk taking. Becoming an actress and deciding to move out to california where I knew no one was a huge risk. It was one that I tried to back with a lot of research and with a lot of training but at the end of the day it was still a risk. I do feel as though a lot of the things that have the most payoff are the biggest risk. Even getting married and deciding to tie yourself to one person in every way financially, legally , emotionally is a huge risk. Read more>>

Solomon Savoy

One of the biggest risks was starting my own business. Starting a business is something that I had never done before. I did not have anyone to go to to ask them about where to begin. I went to the only person that I knew could provide an answer and that is the Great I am God. Through God, I was able to come up with a business plan, logo, and motto, start a YouTube channel and become certified as a narcissist abuse recovery coach. Through God anything is possible and I firmly believe that. Read more>>

Synphonie Conway

I was a teacher for 7 years.. I completely trusted GOD and I walked away from my job without a plan! Although I was risking everything my faith in GOD was (and still is) bigger then my fear. I was no longer happy in my career.. the career I once dreamed of was no longer my passion. I’m a firm believer that GOD will make you uncomfortable in a situation when it’s time for you to move.. Read more>>

Reggie Jackson

Taking risks involves some calculations but also an authentic belief in yourself and what you are pursuing. One thing that must be considered when taking risks is that it could fail, we have to be prepared to deal with the fallout of that. Taking risks includes being able to deal with the anxious thinking about your decisions (i.e. did I overstep my capabilities? What’s my plan if this does fail? Impostor Syndrome).  Read more>>

De’Netra “Netra” Norris

I am a Kansas City, MO native and I recently took a leap of faith and relocated to Orlando, FL to expand my brand, networking and personal growth. I am forever grateful for my hometown yet I began to feel like there was something missing or even a sense of feeling stagnant. So I began to talk to my mom about my decision and wanting to be in a different environment to learn new things. When my mom caught the plane to come get me that same day I told her I wanted to get in my car and drive to Florida that same day, so we did. Read more>>

Laura Narpaul

I think many people have a million dollar idea and do nothing about it. And I don’t necessarily blame them. We get so used to our comfort zone that we can’t imagine what life outside of that would look like. I can definitely say, being out of your comfort zone is taking a risk. We don’t know what to expect. But you can’t grow or reach your potential if you stay in a comfort zone. Consider that the comfort zone is a physical place not a mental place, where you take refuge at the end of the day. Read more>>

Kendra Julion

One of the biggest risks I’ve taken just happened a few months ago. I was working full-time in the Public Health space and being a Travel Agent part-time. I was doing well in the Public Health space but I knew that I wanted to work for myself and that my true passion is being a Travel Agent. With the full-time job I couldn’t dedicate the time/effort it needed to make my business flourish – really pushing my social media efforts, developing group trips, attending trips for Travel Agents to learn about destinations, and learning sessions. Read more>>