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.

Destiny Griffith

Taking risk to me is the equivalent of taking a leap on faith and hoping….just hoping that you’ll land on all ten toes. Recently I resigned from my position as a massage Director to solely pursue my career in music. Here I am an independent artist and creative in Cincinnati, Oh, a full time mother who all the responsibility of managing and financially sustaining her household while pushing her dreams is in full effect.. Facts that I don’t take lightly at all. I took a risk and resigned from best paying position I’ve had since ever working a job. I did it because I believe in ME. Read more>>

KT FYR

The For Your Reference podcast is a lot of fun and I enjoy having a creative outlet to discuss TV and film. We were encouraged by a fellow film podcaster to reach out to be added on publicity lists. I reached out, and as anticipated, did not receive a response. We are an indie, two person operation so was not expecting to be accepted but was glad we put ourselves out there. Read more>>

Makaela Meadows

Risk taking….even writing those two works is overwhelming. Taking risks involves the unknown, doing things outside your comfort zone, and not knowing what is on the other side, which can be daunting. If you ask my friends and family, they would tell you that I am typically not a risk taker, I do things by the book and follow the rules as I like the outcome. HA! I like measured results, I typically like to understand what I am getting myself into and that is the line I walk. That seemed to change when I hit my late 30s – for the better. Read more>>

T’Shauna Henry

In the past two years, maybe three, I’ve made significant choices for my career. Back in 2020, I was wanting to retire from retail completely so I can focus on getting and committing to work in the performing arts; but then the pandemic happened. Honestly, thank the stars for it. In 2021, I left a stable yet steadily slow job as a photographer in a studio since their senior session season was coming to an end and to focus on my business, which was also a photography service, full-time. Read more>>

Young Romantics

Our story to this point has been rooted in risk. Beginning as just two high school friends recording music in a car with little besides a will to create, we’ve become a family through five years of writing songs, playing shows and living the day-to-day uncertainty of trying to “make it” together. However, if we had to pinpoint the biggest risk we’ve taken so far, we’d mention the week we spent this past January at a studio in Franklin, KY, called Thunder Sound, where we recorded our most recent project and first full-length album. Read more>>

Samantha Gordon

I took a risk on leaving my 9-5, to blog, and I’m glad that I did. I always knew I wanted to be my own boss–my great-grandfather(army vet) had a lot to do with that. He was his own boss running a travel agency business, after his many years serving in the army. He taught me almost everything I know in regards to business and he really gave me the blueprint to it all. He believed in me the most, even when my ideas were crazy–he’d tell me to figure it out and make it make sense lol. I left my 9-5 in 2019, Read more>>

Nicole Firth

Event planning is a low risk entry way into the event world. You can start this business as a side hustle while still holding down a typical 9 to 5. That is exactly what I did. I started small and with lower packages to build my portfolio and grow my network. The time came to finally take the risk and quit my day job. It’s easier said than done. For years, my best friend kept telling me to quit my job. She knew I wasn’t happy and knew if I just took the leap I would succeed. Read more>>

Tori Nix

Throughout my life I was conditioned and was always told what life was supposed to look like — that you were doing well if you went to college, you graduated, you got a job, you got married, you had kids, and you work until you’re able to retire. While this suits many, I always went against the grain. Most people call me a “rebel”. Since a kid, I was always drawn to my creative side and had a different vie of what I was taught. At 17 I created a plan and at 19 that plan was in full action. At the time I was in college, attending Howard University, majoring in the Tv/Film Department, and minoring in Electronic Studio Art. Read more>>

Terrence Ashwood

Taking a risk on being a self sufficient provider is one of the scariest and toughest endeavors I’ve embarked upon. Especially because I’m still so new at it. I am still working in my job as a educator as it helps me prepare for the future self I look to be in helping youth in a different capacity. For me there has always been a drive and passion inside to be more then what I’ve been. The hunger for financial and time freedom became even stronger when the pandemic happened and I started to reevaluate things and what I really wanted. So i decided to invest in myself in many ways, one being I started ashwood apparel LLC. Read more>>

Shronda Armstrong

I took a risk in following my dream of leaving an industry I was unhappy in to pursue my dreams of building my own career. I was excelling professionally but, on the inside, there was a huge hole in my life. I was fulfilled and my stress was affecting me physically and mentally. I took a risk in resigning and focused my time in expanding what started out as a t-shirt business. Read more>>

Betsy Stecker

After a 30-year career in communications and education, I made a decision to build a completely new career for myself: one for which I had no formal education, apprenticeship, or professional experience: a career in art. I was always creative, which I expressed when I had opportunity, but rarely through art. In 2018 I made a decision to explore printmaking, and I taught myself linocut blockprinting. Read more>>

Jill Massura

At 40 yrs old, I found myself in a place of personal crisis, commonly referred to as “the dark night of the soul.” I was disillusioned about who I was, lost about where I was headed and scared to admit that I was unhappy, in spite of my life looking picture perfect on the outside. My decades long relationship with alcohol had taken a dark turn, following my Mother’s death, and had grown into a dependency that filled my life with shame and kept me from pursuing anything outside of the daily routine of taking care of my family by day and disappearing into the bottle at night. Read more>>

Keir & Ashley Swisher

We also loved the question “what did your parents do right?” So this is answering both! What our parents taught us about investing has encouraged us to believe that risks yet challenging are worth it when you value the relationships that the risk may grow. It is a huge risk taking on a business venture like this with what might better be set in an intercity. Read more>>

Melissa Green

Being an entrepreneur is a risk in itself. One of my regrets is not having started my business earlier. It also hasn’t been an easy road as a business owner. There are constant pivots, learnings, and growth along the way. If it wasn’t for my mentors guiding me, I would honestly be lost. I highly recommend that you obtain mentors if you are wanting to start your own business. But make sure these mentors are successful. Anyone can talk a big game, but it’s those who have been there and made it that can truly lead you. Read more>>

Nina Duffy

Starting a business is taking a risk, financially, personally, and career wise. I took this risk because of an internal issue that arose at my previous spa. This was the push I needed to get started on my own and so I did. I first started with an idea of what I wanted, visualized it, and started putting it together in November of 2021. I was scared and nervous, but anything worth doing usually makes you feel that way. I dove in head first, so to speak and haven’t looked back since. It was a risk worth taking. Read more>>

Karlo Gesner

I was living in an apartment above my parent’s garage at the age 0f 24. College……was a mislabeled attempt to say the least (I had recently graduated from Virginia Tech with an Engineering Degree….but I was not passionate about it). Around the same time, I was gifted a Canon Rebel Xti. I had always wanted a camera as a teen, but it was seen as a “poor investment” by my parents as it was an expensive hobby and they didn’t have faith that anything would come of it. Read more>>

LA Dunhoody

Being a successful artist, producer and business owner in Atlanta, many people often ask: Why leave Atlanta, my home, birth place, family, friends and everything I’ve ever known? How am I going to make it? Get new clients, new fan base? To be totally honest, I didn’t have all of the answers. What I did know is that things were good, but I still wanted more. A better environment to raise my family, and take my business to new levels. Read more>>

Kaladia Chaney

I have always been a writer. I just did not realize my potential. When I began writing my first book, the idea of publishing it was a passing thought. I write to reflect, release, restore, heal, and be revived. When I decided to publish the book I was taking a risk by believing in myself. That my work was worth the read – that it was good enough. Then I thought about what a guest speaker wrote on my vision plan. It went something like this, “You will succeed when you learn to get out of your own way”. Read more>>

Nathan Lubeck

In my honest opinion, taking risks is a constancy in the profession of performance. Every time we audition, self-tape, or perform to any degree, we take risks. It is always a, “what if” situation, when we as performers put ourselves and our art on the line. In my personal career, I’ve taken many small and immense risks, for example; There was a production I was in consideration for, in which all the actors had to be well versed in circus training. Read more>>

Michael Gorney

It was the summer of 2019. My wife, Michelle, was 6 months pregnant and I had just went under for a significant knee surgery to fix an ACL, MCL, and meniscus. Following 6 weeks locked in a knee brace I had another 6 weeks to go until I was allowed back to work. Trying to keep myself occupied I would go on long walks and keep up on my rehab. One day, around the corner from our home in Ferndale, a for lease signed appeared. After peering inside to see the space a sense of urgency washed over me. Read more>>

Bee Johnson

I’ve taken a few risks in my life that have really paid off and helped me live my dream. The biggest risk I took was walking away from my 9-5 medical job 2016 to become a full time personal trainer. I worked in the medical field for 18+ years. I started when I was in the Air Force right out of high school. But at my last medical job, the work environment was very toxic due to disrespectful co-workers and management and no advancement opportunities. Read more>>

Scarlett Santamaria

The biggest risk I’ve taken in my creative journey was producing my first event last year. I used to find event producing highly intimidating, especially after interviewing nightlife producers on my Youtube web series and learning about all their challenges. One night after my work shift I had a conversation with my boss and event producer, John Joseph, about my web series’ 3rd anniversary. I didn’t know how I wanted to celebrate it and he suggested throwing an event at my second home, Rich’s San Diego. Read more>>

Erin Black

No guts, no glory… right? Being raised in dusty south Georgia and having two older siblings that were prevalent closed some opportunities but made me realize that I have to think out of the box when it comes to being recognized for who I am, acknowledging all of this in my adolescence. I couldn’t talk to others, most couldn’t even hold a normal conversation without me being consistently referred to them when people saw me, leaving me thinking, Does any know my name? Read more>>

Cj Esher

I worked immediately from high school graduation until I was 25. I always had considered college too much and kind of out of my grasp, something I couldn’t do. I worked plenty of retail and some other odds and ends, Storage property manager, surveillance, and other odd jobs. When I was 25 though I was offered the chance to go to college for free, but I had to move two states. My aunt offered to pay for it and house me if I went. Read more>>

sintia magana

My story is about taking risks. As the CEO of my company, I also had to take steps and measures to make sure that my company’s mission and vision were aligned with. I had to phase out some activities that were not healthy for me and cut out people that weren’t helping in my personal growth. Since I started my business, I have become a different person—more courageous, a greater risk-taker and smarter. – Read more>>

Maria Rodriguez

Everyone talks about taking risks, but no one really talks about what that looks like. For me taking risks means trusting your gut that everything is going to work out in your favor, despite what the actual situation looks like and understanding that failing is not a weakness but part of the process. I could hear my alarm ringing from across the bed, and I thought about snoozing it like all the other days, but I realized it was Friday, and I just had to get by one more day. Read more>>

Teaira Abston

As a business owner you’re always taking risks in order to elevate. A prime example was when I decided to pivot my business to a completely new audience. I had previously been a stationer that served the wedding and events industry for about 5 years and felt as though something was missing. I had become a little burned out and I thought that maybe entrepreneurship wasn’t for me. Read more>>

Casey Stallings

I was born and raised in a small rural town in North Carolina. After graduating high school, I had plans of moving to Nashville, Tennessee to pursue my degree in Audio Engineering. College began and after 6 months of sitting in front of a computer compiling sound files, I realized it wasn’t something I truly enjoyed. Afraid to drop out of college, I had considered the animation courses at school. But I never felt I was good enough. I liked to draw and I knew I was creative, but growing up, my twin brother was always known as the “artist” of the family. I felt like I’d be settling in his shadow. Read more>>

Victoria Todd

One the biggest risks for me was launching VivaVik Artistry. I rebranded into VivaVik Artistry during a time recovering from a horrible car accident. I was told by multiple Doctors & specialist that I’d never be able to walk or function as normal again. I’m a woman of Faith. God told me to break down my old and to plan my new business in my hospital bed. I did just that. He helped me to structure it brick by brick and it wasn’t easy. Read more>>

Cyasia Zackery

My journey of becoming an entrepreneur and black business owner started with significant risk. In the fall of 2014, I was sitting at home, in the small town I was born and raised in, York, Pennsylvania. I remember feeling bored, stagnant, and somewhat useless. It could have been because I spent most of my life in a town with nothing to do and no real opportunities, or because the seasonal depression of Winter was quickly approaching. Either way, I knew I had enough. Read more>>

Sarah Miller Gelber

In 2016 I left a really cushy, high level role at a large gallery + design firm. I was 26 and had been given the opportunity to manage a huge business at a mere 22 years old. By my 24th birthday I was making well over 60k working in the arts(!), planning gallery openings, directing 40+ artists, and helping clientele design their dream homes. Buying trips to High Point Market and New York City were a part of the job. Budgets for exhibitions were flexible (within reason). It was totally dreamy, but still felt wrong. I was living out someone else’s dream. Read more>>

Julietta Wenzel

I chose “taking a risk” because it pretty much defines my whole career as a physical therapist. From my first job out of school taking a position that I didn’t feel even remotely prepared to handle, to accepting a senior therapist position with only 3 years experience when senior therapists I knew had 10+ years of experience, to taking a job that required I also treat children when I never had before. Read more>>

Carolyn Miller

When I was 27, I took my first ever trip to Nashville. Hooked was an understatement. Nashville became like a drug I couldn’t get enough of! It’s called Music City for a reason and it really is Disney World for the musician/artist/creative. I put out original music for the first time when I was 29 and haven’t looked back since. Not living in Nashville, not growing up on country music, not beginning this venture until I was nearing 30 might’ve been considered a “risk” by most. Read more>>

Kayce Laine

There have been three big risks I’ve taken that have altered the course of my life. The first was when I left home to move to New York City to pursue my career in music. At 22, a few months after graduating from the University of Virginia, I auditioned to be the synth and vocalist of an indie-electro pop band based in Brooklyn and after receiving the gig, packed up my belongings and moved there! Read more>>

Anna Volokhova

I feel like taking a risk is part of my character. In 2017 I was working as an emergency doctor in an ambulance and everything seemed to be ok. Suddenly, my grandmother passed away and as she was my closest relative I felt completely lost about what to do with my life. So that’s when I took a risk, left my job, and decided to go Santiago way (Camino de Santiago). This is a pilgrimage that can help to clarify your thoughts and feelings. Read more>>

Jason Hurt

One of my favorite quotes is “No Test equals No Testimony” from motivational speaker Les Brown. Back in 2014, I was going through a transitional phase and trying to figure out what my next steps were. At the time, I had been bartending 3 nights a week getting home around 4:30am and was working event gigs whenever an opportunity came across. I was grateful to earn some cash, but bartending was not something I was super passionate about. Read more>>

Shawn Davis

Take the risk to become greater. My journey started back in 2018 where I left my dream job, Mac Cosmetics. As a single mother and big dreamer my dreams came to an screeching holt when my I realized I was missing out on important moments with my daughters. Grueling demands of retail left me with no time, no weekends off and no elevation. At this moment I realized I want to become my own boss , my own freelance makeup artist . Read more>>

Princess Jones

One risk I’ve taken was retiring from the corporate world to focus on my dream of owning my own bakery. Baking is a passion of mine. I just got to a point in my life where I said life is short. I don’t wanna be in my 50’s or 60’s wondering why I didn’t do this or that. Why not try now? If I fail then At least I tried. So I made the decision to leave my corporate job and focus on my dream of establishing my own bakery. So I put in my notice which was a shock to everyone but I did it for me. Read more>>

Melissa Smith

I am dreamer. I literally have fully ideas that come to me in my sleep at night. I often wake up and write them down or I remember them the next day. In the last 4 years, I have had 4 ideas and acted on 2. Those two were successful in my eyes. Meaning I wrote down the vision, told a trusted person who believed in the power of dreaming and helped me see the vision from beginning to end.  Then rewards and accolades started happening. My short film is still being requested for festivals and now I am beginning a new venture in my entrepreneurial journey. Read more>>

Flynn Heathcliff

I decided after graduating from Georgia Gwinnett College that I would take a position there as a staff-member . While there I spent a lot of time encouraging and showing students how to find themselves, figure out their purposes in life, and live in their dreams. I was doing what I was passionate about, but I still felt an emptiness inside. The job helped me to scratch an itch but not satisfy the flame that was burning within me. The truth is, I wanted to pursue my own dreams and passions, not just support other people’s. I wanted to make music, do photography projects, create my own fashion lines, not just help and encourage students to do theirs. Read more>>

Diemond D

When friends/family or acquaintances ask me about starting their own business, or what it’s like to run a business, it often gets followed up with questions about risks. The truth is, as a business owner, risks are taken on a daily basis but I will always say the biggest risk you’ll take in entrepreneurship is the investment in yourself. The willingness to see your ideas all the way through. I’ve been messing with music my entire life and I only just recently decided to take the risk and turn it into something bigger. Read more>>

Jehda Archer

Being a business owner is a risk in within itself. When I first started my lash and lip gloss boutique I was working as a customer service representative. I took a risk investing in my business out of my paychecks not knowing what the outcome would be if my products would sale ect . I quit my job and focused on my business full term a year later I expanded into clothes , and shoes business was picking up and it felt great to accomplish a dream I’ve had since a kid . Read more>>

Shanta Sweet

In 2016, I left New York and everything and everyone I knew to move to Jacksonville, FL. I didn’t have a job lined up. I wasn’t sure if I’d like it or that I’d stay. I just knew I wanted a change in life. I suffered through some brutal winters over the years in New York and after a life changing, near fatal motor vehicle accident, I decided the cold weather was no longer for me. So, I took a big leap of faith and ended up 1,000 miles south in Florida! Read more>>

The Vending Machine LLC

The Vending Machine LLC is a pandemic baby. I have had many businesses before, but nothing like this one. I sat for some time, taking a mental break from everything… including my previous businesses. Having been on the “scene” for almost 5 years and closing EVERYTHING at once, was risky! I wished that I had a way to take that break as an entrepreneur while still growing my brand, but in my circumstances I did not. Read more>>

Catherine

The biggest, life changing risk I’ve taken so far is giving up a potentially lucrative and stable career path in engineering to pursue environmental conservation work. I always had some interest in nature and the environment but was also a practical person. In college, I thought I could work in industry on sustainability projects as an engineer, but as much as I tried, the day to day tasks did not appeal to me. I made it through the degree but after college, I was exhausted, burnt out, and lost. Read more>>