You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken.
Sabrina Watts
One of the biggest risk I’ve experienced was flying out across the world to be with my family and to be with my dad who was battling and still battling stage 4 cancer. At the time I was married and my daughter was young, covid had hit unexpectedly causing changes in my life. We and of course most people around the world had gone thru an ordeal during this time. I was caring for my dad, being a mother and studying at all the same time trying to accomplish what I said I was. Read more>>
Mikel Galati
The biggest risk i did was taking a dive into this business full time. I taught myself screen printing, through YouTube videos & trial and error. It was more of and my main focus was to print for my own band at the time. I was maybe barely 21 years old. I was working dog walking gigs, super part time and just trying to make things work. A few months later, i landed a job in the print shop at a local record label. I jumped on it, but was too afraid to take the “screen printer” position. So i settled for shop hand/floater. Basically i did everything, besides print. A few short days into the job and i realized i would have been comfortable in the position, but it had been filled. So i was stuck as the shop grunt! Read more>>
Makati Seekane
As Bophelo Fragrances founders, we took a leap of faith and ventured into business. We wanted to start something that’s meaningful. We want to a candle making course then we came back and did the ground work. We researched the candle market and learned that there was space for our business. We created affirmation candles which provide a safe heaven for the user. We are lawyers by profession and wanted to create a space for recouping and relaxing after a long day at the office. Our affirmations are in Sesotho so ‘re leka gape’ means we try again. Read more>>
LeKesa “Kesha” Whitner
Mrs. Lekesa Whitner became the first woman of color to run for Mayor of the City of Spartanburg in 2017. She may not have won that particular race, but her contributions to her city are undeniably the mark of an outstanding leader. Mrs. Whitner is guided by the mantra and has coined the phrase: “If you build the people, you grow the city!” Read more>>
Stephanie Jameson
A few years ago, I was given an opportunity to follow my inner voice and create something all new and totally illogical. Despite being a highly intuitive kid and young adult, I suppressed my inner knowing and allowed the conditioning I was exposed to in life talk me out of my power. I was taught for year like so many to look outside of myself for the validation of what I felt inside. Being so different and for reasons I later learned in life were for a purpose, this was very hard for me as I was constantly conflicted and my head would frequently battle my heart. Read more>>
Danielle Librera
I worked in the culinary field for many years – 18 years as a Pastry Chef in fact. I loved everything about it. The energy of it all fueled me, but life has a strange way of showing you where you should be, and how you should ride it out. I was running my own business (Bakery) in 2008 when the economy took an incredible decline. I felt like overnight the majority of my customers were gone. I was struggling to pay my businesses rent and was forced to close my storefront and move my business into a coffee shop. Pretty much simultaneously my father became very ill with cancer, and my husband lost his job. We lived in Phoenix at this time; and with this economic downturn the housing market was really, horridly, unpleasant. Of course we had our home on the market and couldn’t sell it. I really felt like I was sinking deeper into a whole where I would never see the light of day again. One day morning I was sitting quietly by myself and I thought – You just have to pick yourself up and go for it. There is no harm in trying. Read more>>
Street Product
I wouldn’t really say it’s a big risk or a small risk but one of the most consistent that I take is investing in my music. Me and friends us this term, you pay what you weigh. That just says you get what you give. Once I started to stop low balling my craft financially, my views started going up, my streams and downloads started going up, I started getting booked for paid events. So basically I just went all with putting my money in the right places and now I’m reaping the benefits and reward. Read more>>
Isabelle Marie
When trying to get your foot in the door in your profession and there us uncertainty of how & where to start, the best way is to just jump in head first with good ol’ fashioned risk-taking. When I first started teaching yoga, I had what is needed for the job- the knowledge, passion, but lacked the wisdom only gained from rolling up your sleeves, a.k.a. life experience. Read more>>
Stacie Watts
It seems moving to Austin, TX was just the beginning of my life of taking risks! In 2016, after my divorce, I moved to Austin, TX with no friends and started from scratch at Bonobos (a menswear boutique). I packed up everything I owned in my small SUV and 5’ x 10’ U-haul and made my way half way across the country alone. I found a random person through a friend of a friend on Facebook who was looking for a roommate and we decided to move in together without even meeting each other first. She was a recent college graduate and despite being in very different places of life we made it work. About a year later, I took a leap of faith, leaving Bonobos to join a real estate team, even though I was being ask to be promoted to manager. Things were going good, but I knew they could be better! Read more>>
Susie Frazier
When I was diagnosed with ADHD as an adult at 47, my lifelong hypersensitivity to interior settings suddenly made sense. Cold spaces devoid of nature, with too many lights, hard surfaces, and competing acoustic sounds have been life-long challenges, and I’ve always searched for ways to have personal control over my sensory experience whenever possible. After learning many of my innate coping practices involving nature were backed by research happening around the world, it occurred to me that sharing these methods might be helpful to others who have ever felt uncomfortable inside a workplace or a home of their own, whether they had any formal diagnosis or not. In 2018, I shared my story and philosophies in a self-published book called, Designing For Wellness. Read more>>
Cloe Galasso
One of the biggest risks that I took in my life was moving to NYC when i got stuck in USA during the 2021 pandemic lock down in Argentina. I had travelled to Miami to visit some family and as soon as we landed, we were informed Argentina had closed their frontiers. I decided to fly to NYC to work in my art there while i waited to be able to enter to my country again. It was a great leap of faith that, with a lot of hard work, dedication and constancy started giving its results. Read more>>
Megan Easterday
Once upon a time, a mid-twenty-year-old named Megan Easterday started her baby multimedia company… Ok, I’ll stop with that ridiculous beginning–haha! I had always known I was meant to own my own business. I don’t know exactly why, but I always intuitively felt it within my entire being. Unfortunately, at the time, I didn’t have the confidence and courage to take those first steps. Plus, in my logical brain, it simply didn’t make sense to pour all the time and energy into my own venture. Read more>>
Cindy Eggleton
In 2015 the Brilliant Detroit Founders met. They bonded by a desire to create a radically new approach to kindergarten readiness in Neighborhoods. They saw that the best way to do this was to create a unique model delivery in how early childhood success was approached. Jim Bellinson brought an amazing investment and scaling background. Carolyn Bellinson brought a focus on building people through clear pathways. Cindy Eggleton brought early childhood, impact and community expertise. Read more>>
Lillian Puleo
I took a huge risk buying Board & Brush Marietta- East Cobb. I had never owned a business, much less managed people before. I was a stay at home mom that took a leap of faith! Shortly after the purchase agreement went through, Covid hit and the whole world shut down and I freaked out just a little bit! However, with the amazing support of our community and customers, we’re still here over 3 years later! Read more>>
Alyssa Kulesa
Three years ago, I was walking to Whole Foods on a warm, sunny day in August. While strolling through the park that separated my apartment from the store, I left my phone in my pocket and decided to observe my surroundings instead of mindlessly scrolling. I saw dogs not-so-patiently waiting for their owners to throw a ball, a group of girls chatting on the hill, and far too many men in plaid. Two guys conversing caught my eye as they walked in the direction I’d just come from. I smiled as I walked past. And if that’s all that had happened, I would have never met my husband. Read more>>
J’Marcus Alfred
The biggest risk I’ve taken was quitting my full-time marketing job to go down the path of being a creative full-time. Up to that point I did what was expected of me. Going to college, graduating, then finding a job in my field. For a while I was content with what I was doing because I’m doing what I thought I was supposed to do. Over time I realized it wasn’t a fit for me. I spent a lot of time on the what if’s. I knew what I wanted to do but couldn’t exactly see the path. That kept me from going for it sooner. I knew from my time working that I had the tools to be successful but that would also mean not doing what was expected and if it didn’t work out how others would view me. Read more>>
Deidra Smith
It’s a huge risk to bet on your dream. You don’t realize the investment and commitment. All of your ideas are basic at best. I totally depended on drive and determination. I took my time and had to dig my heels in to get established and flourish. For me, it was a risk well taken. If I had to do all over again I would in a heartbeat. When I first started I knew nothing about the business or what to do. I learned through lots of trial and error and taking multiple risks and thank God they panned out. Read more>>
Breeda Miller
In the midst of CoVid, as I sat on my porch in my robe, I asked myself a big question. “What would I do if I could do anything?”. The answer came quickly and confidently. I would write a one-woman show and perform it all over the world. I had never written a play, I had no agent or connections in the theater world and I was terrified of remembering an entire script. Like my experience as my mother’s caregiver, I didn’t know what I didn’t know. But I did know I needed help. I reached out to a friend who did know about playwriting and directing plays. He said he would help and I asked how to begin. He said, “Just start writing your stories”. So that’s what I did. After six months of putting all my thoughts and ideas down on paper (or digitally to be honest) and then we met up and he read my “script”. Read more>>
Chen Alyesh
Embarking on a creative career is like stepping into the unknown, taking a leap of faith into a world of uncertainties and possibilities. It’s about putting your heart into every piece of work, hoping that people will connect with your art on a deeper level. Seeing others appreciate your creations from their own perspective is a rewarding experience like no other. Read more>>
Allison Conway
I feel like I am taking a risk every year living in Brooklyn. I work part time at a company called Court16. I help make the arts and crafts for kids. It is the perfect part time gig for a cartoonist and illustrator! But it does not cover all of my expenses every month and so every month feels like a gamble. My career is at a steady(ish) flow job wise but it is still hard to make money. When I graduated college I lived at home for a year and then moved to Brooklyn without a job fully expecting to immediately run out of money and have to leave after a year. I have managed to stay in NYC ever since and that was 6 years ago. Every year I resign my lease it feels like a risk but it’s a risk I happily keep taking. Read more>>
Lisa deSouza
Founding the Santa Clarita International Film Festival has been one of the biggest risks that I have taken in my life…and trust me I have taken quite a few. I have always been a creative spirit having started my acting and then writing and directing career in the off-broadway black box theaters of NYC. However, like most artists we have bills to pay and so I had to work and found myself learning how to make content for the web. That brought me out to Los Angeles and I made a lucrative living in the tech industry while digital marketing and internet content was exploding. Read more>>
Sonya Goss
In 2012, I was laid-off from my job due to a RIF (Reduction In Force). I was so worried how I would be able to contribute to my household. My husband said, not to worry, we will be just fine. And he suggested that I turn by part-time Photography Business into a full-time business. I was like, what? I won’t be able to make no real money money. But with his support and investment in me, I took that chance and Sonya’s Creations became a Full-time Business. And I’m blessed and fortunate to not have to get a 9 to 5 job since. Read more>>
ReAnna Romero-Alirez
Back in June 2022 I decided to take a risk and go for my certification as a stretch therapist. This was a field I knew little about at the time, I also had a full time job working for DaVita, a family and busy life already. I took a risk driving all the way to Arizona for the certification and absolutely loved it! I have never felt so at home as I did there, in the presence of other like minded individuals. It really pushed me to take another big risk in November of 2022 when I quit my full time job to just take on stretching clients. I was nervous not knowing whether I would do well, whether I could pay my bills and just not knowing what I didn’t know. Read more>>
Lindsay Leigh
My professional career has been quite a long and winding path. When I was getting ready to go to college, I would get the common, “What do you want to be when you grow up?” and my answer was always something like, “I’m not sure.” or “I’m still exploring that.” I said this because so many things sounded interesting to me from entomology to teaching to interior design. I’ve always been a jack of all trades – interested in many different things – never one singular topic. Read more>>
Holly Gotfredson
A life event in my mid-thirties gave me the wisdom to step out in faith in the business world ten years later. My husband and I always wanted to have a large family. We struggled with infertility for several years and our miracle child, Leigh, was born. As she grew, we knew we wanted her to have a sibling so we went through several fertility treatments and procedures. When none of that worked, we looked at next steps – calculating the risk, fear and trying our best to plan for all contingencies. We spent two years on an international adoption. We carefully planned and completed paperwork each step of the way. Once we completed the process, we were approved for two children and traveled for almost three days to a village in Kazakhstan. Read more>>
Tylar Jane
In 2019, I got out of a very long, awful relationship and moved to Ohio. I started working as a barista again in two of my managers stores with the prospects of opening another one up and me managing it. I love working with coffee, so this was a dream for me! That was 2019. When COVID hit very soon after, I officially started selling my artwork as we had to shut down our cafes. I love working in coffee, so I was honestly devastated! Not to mention, it was featured in a blueberry field in a giant greenhouse. Totally my vibes. Read more>>
Kent Barker
The first real passion of my young life was dance. I studied at a top level academy from age 6 to 18 and then went to Joffrey Ballet as a scholarship student the day I graduated high school. A knee injury ended those aspirations and a couple years later I found my life’s true calling,,,photography. Fast forward 40 years. After a long career as a professional photographer, I suddenly found myself in the middle of a pandemic… sitting at home with no work and nothing to do. My response to this odd gift of time & isolation was introspection…and the result was an epiphany of sorts. I realized that there was something unrequited in my life as a photographer and that was Dance Photography. Dance was my first love and photography… my life-long passion. Read more>>
Erin Bowlware
Im a full time content creator and have 5+ years of experience in the industry. I am now also a mom to an incredible one year old! This is the life I’ve always wanted and that I created for myself with the support of my husband, but struggling with my mental health for over a decade has clouded my lens on life. I’ve recently found myself in an incredibly low slump. My creativity seemed to vanish as the mental fatigue of being a new mom set in, and I honestly felt like I’ve completely lost touch with myself. Something had to change and fast, before I continued spiraling down this hole of depression and anxiety. Read more>>
Caitlin Cipriano
Like most people I was not prepared for what 2020 was going to throw me. I was pregnant with my first baby and due to have him in March which is when the whole world went upside down. I had planned to go back to my stable job working as a High School Athletic Trainer but it became evident at the end of the school year that things were not going back to normal anytime soon and thought of sending my son to daycare in the midst of a global pandemic was something my husband and I were not willing to do. Read more>>
Matt Nestor
Risk is always around when playing music, which I love. Whether it’s changing set-lists, how the crowd will react, or different venues and their set-ups. The challenge of all the risks involved in playing live music is what I really enjoy and makes the performace so rewarding. When a risk works out, it’s the best feeling. When it doesn’t, you take notes on how you could have played/ performed better and move on. Read more>>
Jenna Wentland
The biggest risk I took, was going into business ownership with a business partner whom I had never met. I was contacted one day by a person I had never met, Aditya Rengaswamy, in regards to the current owner of the former salon I had worked at (Shag Salon). The owner of that salon was looking to sell the business, and this person had reached out to me to ask a few questions about why the owner might be selling, seeing as how I had worked there with him and may have some insight. Read more>>
Colleen Quinn
Recently, I have taken the risk of renting a space to sell my clothing line, CQuinn, at the Glendale Galleria pop up shop: The Drop at Glendale. It’s a large investment of my time and money while I’m in the middle of wedding season – my busiest season since I make custom wedding dresses & offer alterations. While this will be an incredible learning experience for my brand – seeing what styles/colors/fabrics sell or not – it’s scary to be putting in such a large personal commitment when I don’t know what the payoff will be exactly. I also am not much of a risk taker – I’m pretty good at talking myself out of doing things – but with the incredible support of my family & loved ones, I can always count on them to help me take a risk that could end up with a great reward in the end! Read more>>
Madonna Cicconi
One of the significant risks I took on my entrepreneurial journey with Cicco Aroma was deciding to open The Wellness Studio much earlier than originally planned. Our initial vision was to open the studio in our 5th year of business. However, the opportunity presented itself when we received the Vaughan Main Street Grant award of $10,000. It was a turning point for Cicco Aroma as it meant the potential to accelerate our growth and expand our impact on the community. However, I was initially hesitant about deviating from our carefully laid out business plan and timeline. I had concerns about the readiness of the business to open a physical location and whether it would negatively impact our long-term goals. Read more>>
Christian Ojala
I decided to take the risk of being a business owner instead of having a normal 9-5 job. Starting a business from scratch is extremely stressful and can be an extremely big risk. Starting from scratch, you are essentially starting from the bottom and having to work your way to the top. Meeting new people, working for free, building a portfolio, and building your network takes lots of time and a proven track record to finally start making money doing something you love. In my case, I wanted to follow my passions and start a full time career flying drones and filming the world through the vision of a camera. It so happens to be a new path that hasn’t really been understood by many yet, but it clearly can be extremely enjoyable and profitable. Read more>>
Myles Nye
After navigating the business from its inception through the lockdowns, my business partner told me a year and a half ago that he wanted to bow out of our partnership. In an amicable way, I bought him out and went from being co-founder of my first business to, fifteen years later, a first-time sole owner. I can’t tell the story of how the transition went because it’s still happening: this is a story I’m in the middle of it, and it is hard, especially with the state of the events industry feeling uncertain. This sector hasn’t yet landed where it’s meant to be in the age of COVID vaccines. But I do not need to worry about failing to push myself or getting opportunities for growth, because I am being pushed and I am growing as a business owner. Read more>>
Olivia Orona
The biggest risk I’ve taken in my career was not going back to a Corporate job to become a full time Creative. I use to be very successful in managing a team and reaching company goals. I was passionate about training, development and helping others grow into management roles. I pushed a positive work culture constantly. I then realized my mental health was failing and I made a hard decision to pursue not only something I loved but something that could help me manage my mental health better. Read more>>
Melissa Esmeralda
I like to describe myself as someone who’s 97% introverted. A common misconception is that I’m shy (I used to be) but the reality is that I just don’t do well in groups. I don’t know what I’m supposed to do so I’m usually wherever the snacks are. I had just quit my job to pursue my business full time and had never been to a “real” networking event before. I was extremely fresh to business–hadn’t even made my first $1k yet–and I knew this event was going to be full of seasoned business owners with way more experience than me. I sat in my car for a while because I didn’t want to go. I had very little experience and a bit of a babyface which didn’t help. I wanted to be taken seriously but how could I if I wasn’t willing to put myself out there? Read more>>
Catherine Leone
Although my main artistic outlet is painting and digital illustration, I create in a variety of mediums to keep my mind fresh and to push myself and my abilities. Taking risks in the art world is a very scary feeling, but is very rewarding. Often I will see something online that I have never tried and I encourage myself to jump in and fully immerse myself in this new process. This can feel risky, especially when you are creating for an audience or with the intention of bringing items to shows because nothing is 100% guaranteed to bring success. A recent leap of faith I have taken is into the world of glass sublimation. I was very nervous at first, both for the sublimation process, but for the finances I would be dedicating to this new medium. After contemplating it for months, I finally jumped in feet first and quickly found this art to be my new hot seller at conventions and markets. Read more>>