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.

Gianluca Boncompagni

The biggest risk we ever took was starting the business, which then opened the door to a lot of other risks. As a company, we didn’t have much funds at the beginning and that’s scary. It also means you need to be careful and on top of every single detail, since the smallest error can derail your investment and effort. However, the biggest risk we took was attending to our first Overland Expo in Arizona. It meant flying to Arizona from Costa Rica (where our brand is from), shipping our products there and preparing for an Expo which we had never attended. We weren’t sure how to properly prepare, what to expect, etc. Plus, it also meant a huge investment for us. It was a big gamble. Read more>>

Ken Fong

Back in early 2015, my friend Christopher came to me with a surprising proposal: why don’t we launch a podcast that focused on Asian Americans? We’d worked for several years on a documentary film project that was taking longer than expected. Rather than twiddle our thumbs, he suggested that we produce a weekly show that would zero in on Asian American culture-makers and -shakers. While this sounded intriguing, I was a bit cowed because, even though I’d heard of podcasts, I’d yet to listen to any. He assured me that this was an unfilled niche in the podcast universe, and that I already had enough national recognition among AAPIs to attract a good number of listeners. Since May 2015 we have consistently dropped an episode/week, garnering listening throughout the US and around the world. Read more>>

Amya Harvey

Every popup event or market that I sign up for is a risk being taken. Preparing for these opportunities can be time-consuming and financial investment when buying ingredients and supplies. There is no guarantee that you will sell everything or make a profit, but that’s where your other motivators come into play. It doesn’t have to be all about the money, there is a risk of making no profit. But at least you gained a few more followers, gave out business cards, and got your name out there. Anything worth obtaining calls for sacrifice, such as sacrificing time and risking not gaining any profit. Read more>>

AstroKnot Collective

With being a creative, entrepreneur or artist you are always faced with adversities that could discourage you from your journey. The road we often choose isn’t the most popular option compared to working your typical 9-5 and joining the hamster wheel but there are plenty of positives that come with taking those extras steps to create a new outcome for yourself. One of the biggest risks as a collective we have encountered is garnering our multi use art studio. The idea of having and managing our own space has been something we’ve dreamed of for a while. In 2021, we partnered with a space in Philadelphia that acted as our headquarters for a few months. The space included a variety of supplies such as shirt press, video equipment, backdrops and more. Read more>>

Sydney Hoff

Early on in my career, I had to make a decision to either wait for clients to approach me or to take initiative and actively introduce myself to potential clients. Despite the fear of rejection, I chose to take a risk and reach out to various businesses and entrepreneurs. Some responses were disheartening, but I learned not to be deterred by a ‘no’ and to persevere. I’ve had several instances when local business owners have declined my graphic design services due for one reason or another. Whether that be budget constraints, or just not feeling quite ready to pull the trigger to take the next steps with their business operation. However, months or maybe even years later, they approach me, having reconsidered and recognized the value of investing in quality design. We are then able to collaborate successfully! Read more>>

Heather Barlin

To me there were 2 huge risks in forming my newborn and family photography business in the San Francisco Bay Area. The first was when I went from part-time to full-time and the second was when I opened a photography studio instead of going home to home to photograph. Launching a business can be incredibly challenging and sometimes having the gusto to take that leap holds people back. For me, it was about 13 years ago and I was working full time for another photographer and on the side doing my own photography, focused on maternity and family at the time. I was living in Oakland in a lovely 2 bedroom home, with one room operating as my office for my dream business I wanted to launch. Read more>>

Verlancia Tucker

Leaving my dream job as a classroom teacher due to mental illness was the biggest risk I have ever taken. For many years I struggled with depression and anxiety. I started struggling with mental illness while attending my senior year in high school and continued to struggle on and off until I made a decision that saved my life at age forty-one. I took a huge leap of faith when I gave up teaching to go to therapy. Sadly, I felt as if life had gotten the best of me. I merely existed in a world filled with ups and downs, mass chaos, heartache, losses, and regrets. I ignored the conundrum of inner cries for help earlier in life because I wanted to continue to be there for everyone around me. Read more>>

Sydney Anderson

A big risk I took was when I went out of state for college. I had never been to Louisiana nor had I been to the South. I found that this was a huge risk for me, considering I knew nothing about what was to come. I graduated from high school during the beginning of the pandemic and didn’t know what to expect as a freshman. Getting my degree in film and television was also another big risk, as I could now be considered an artist, and the expectation for a high salary out of college was considered gone. As a creative, you are always supposed to take risks, whether they be big or small. I found my creative passion through risk, and that is what fuels my creativity. Read more>>

Halie Behr

I have taken risks my whole life. It was a risk at the young age of just 15 years old, to attend auctioneering college with folks who were much older and who were already established in the industry. It was a risk to continue to pursue auctioneering and move off to Colorado where I knew only a handful of people at 18 years old. It was a risk to move into the male dominated automobile auction industry as a female. It was a risk to ditch my 9-5 job and go full time into the auction industry with my fundraising business and contract work as an auto auctioneer at just 26 years old. Read more>>

Jeff Perreca

One of the biggest risks I’ve ever taken is going from writer to writer/director. After years of writing screenplays and pilots and having varying degrees of success like winning contests and optioning scripts, I found myself at a crossroad. I didn’t have any reps (agent or manager) and staffing on a TV show is close to impossible without them. (Though I do know a few who’ve done it.) Mostly, I was tired of writing stories and having a computer full of PDFs. Read more>>

Alex Golden

After my first couple years of DJing and working at my day job, I came to a point where I knew that continuing to pursue both was unrealistic. I was resenting my day job, and coming in tired every weekend from burning the candle at both ends. One day I was at a party and had been chosen to have my tarot cards read by a psychic. She said I was working two very different jobs, one that I thought I should be doing and one that was a creative passion. She told me if I chose to focus on what I was passionate about, my career would flourish. About six months later I quit my day job, and a week after that I was booked my first music festival. Read more>>

Emilee Melin

A lesson I have learned is, it’s not about taking one risk or about having one huge experience that has defined life…but rather embracing everyday with the idea that there will be risks and challenges throughout the whole journey and it’s within our power to conquer ahead. When I try to narrow down a time when I had one risk that affected my path, a hundred memories come to mind. Memories of when I was in a situation that made me uncomfortable, scared the living wits out of me, or made me feel unsettled. Read more>>

Mariana Blanco

Taking a risk is always scary, I will always think on doing something very important but I am one of a kind person that thinks too much and won’t do it because of the cons, most of the time I tend more towards the bad things that can happen instead of focusing in the good positive things. But one day when I started noticing that I was getting busier than last year I took the risk, thought about it and couldn’t get that out of my head so I did it… I quit my full time job to really work on my business!!! so this year 2023 my business its been my full time job and believe it or not is not as bad as I thought for many years. Read more>>

Jerrilyn Lake

I remember when I quit my job in 2018. I was scared, but I knew what God had shown me. I knew that I could trust Him, but also myself. So, I took a leap of faith and decided to pursue a full time entertainment career. I love that I was able to make money online from home, because just a year and a half later, the pandemic hit. While everyone was scrambling, I was taking advantage of a new social media platform, TikTok. I gained over 1 million followers in the next year and haven’t looked back since! Read more>>

Jackman Raps

Committing to becoming a full time artist is one of the biggest risk a person can take. It takes a lot of faith in your self, and in your craft to take that leap. We all have a dream, 99% of people never take that leap to go and chase it. There is a lot of fear and questions that hold people back. With that being said, just taking that first step towards chasing your dream is the biggest risk ANYONE can take. Read more>>

Ollie Briggs

Back in 2017 I had a good secure job as a teacher of art and design. Steady professional progression pretty much guaranteed, decent holidays, etc But I was moved and motivated by different things. Around this time my partner became pregnant with our first child and that seemed like the perfect time to jump ship and start a new career! Much to the stress of my dear supportive partner :) So this tale is about risk, albeit managed risk. Starting something new, in my case a youth organisation built on the unshakable belief that the arts and creativity have the potential to form structure for freedom required to change lives. Read more>>

Dorica Benson

In January 2022, armed with only $300 in my savings account, I took a leap of faith, packed what I could and left behind my familiar life back in Ohio to pursue my dreams in New York City. I moved into a stranger’s basement, far away from my family and hometown friends, and embarked on a journey filled with uncertainty and challenges. I know that sounds crazy as f*ck, unrealistic, on like some movies type sh*t, but yolo right? The odds were stacked against me but I promised to never let the environment I grew up in define my destiny and I. I be insecure sometimes because I don’t come from a wealthy background, however, I’m courageous and smart as hell, with a wealthy mentality so I believe in the power of alignment and conscious manifestation. Read more>>

Assia Micheaux Johnson

The biggest risk I’ve ever taken in my life is trusting myself, my voice and my purpose. That purpose has been a guiding light, even when I felt unsure of that purpose or when the weight of the world dimmed my light. So, when the world seemed to come to a screeching halt, I took a risk with an old creative collaborator on an idea for a podcast. Prior to launching the podcast, we taught a drama class to teens and young adults with cognitive and physical disabilities and we knew that we wanted to do something that continued to tell stories once that class came to an end. We didn’t know what, exactly at first, maybe another show or web series like her previous projects with other creatives, but nothing quite stuck. Read more>>

Vanessa Flowers

I think the biggest risk I ever took was quitting my job in 2019. I knew I wanted to do something more creative and felt the only way to achieve this was by leaving my role. I launched my own social media consulting business soon after, aimed at helping socially-conscious people and brands show up better online. I found clients through previous co-workers who knew my work and while organizing my community events, I would meet experts who needed help with their social media, so they’d hire me after they saw how successful I was at promotions and cultivating community. They’d ask me to do the same for them. Read more>>

Shannon Mack

There are many different ways to look at risk. Risk can be calculated or reckless. It can be intuitive or reactive. As I am writing this, I am reminded of the ways in which I do and don’t take risks in my daily life. Those moments where I wanted to say something and didn’t, and feel the twinge of, “that’s not something I would do.” Or, the opposite, when I act or initiate “out of character,” and I feel a sense of opening within myself…like “what else is in there?” I think this applies to life on a larger scale too. The biggest risk that I am deeply afraid of taking is the risk of not taking risks. I’ve always loved Anais Nin’s quote, “life shrinks and expands in proportion to one’s courage.” I feel this in a very literal sense. I start to feel my world and sense of self shrink when I am not actively taking risks. Read more>>

Jayne Sanders

Like many entrepreneurs, I’ve taken many risks, both personally and professionally. I’ve started three businesses, moved across country alone three times, I ride my horse nearly every day, I’ve bungee-jumped and done a sky dive, and more. I think most people are most surprised at the sky dive. In my 20’s and 30’s, I was drawn to doing a sky dive. I would often tell myself, “Okay Jayne it’s this year!” But it didn’t happen. I kept putting it off, my procrastination fueled by fear. Then one day in my late thirties I woke up and knew this was the time! I was SVP of Sales & Marketing for an international graphics design firm. The owner, Keith, was the best boss I ever had. I called him at home early that morning to tell him I wouldn’t be coming in because it was the day for my skydive. Read more>>

Sarah Granahan

I feel like we are always taking risks in life, that is, if we want to evolve and experience real growth. Some definitely prefer to remain where they are and that is fine too. But if you don’t pursue a risk or change, how will you know what could have been? How will you grow? What new lessons will you miss along the way if you don’t try? If you ask me, I AM a RISK TAKER – are you? Let’s start with how you know if you are someone who enjoys taking risks… So how do you know if you are a true Risk Taker? Have you ever felt like a change needs to be made and it simply can’t be ignored? It calls to this deeper part of you and as much as you try to ignore it, and you just can’t! It’s on your radar or it slowly begins chipping away at your current reality, just waiting to be discovered. It can’t be ignored or stuffed down anymore. Read more>>

Ashley Landavazo

Before starting my career in film, I was Director of Operations in a tech development business. I had a retirement account, I had insurance, I had a regular paycheck, and I had weekends. Previous to that I worked for the American Cancer Society and a bank, again with all of the above with even better benefits and career paths. Admittedly, when its the 18th hour on an overnight, my brain will often swing between thoughts of having a regular job, getting fruit snacks, or focusing on whats on the glowing monitor. Then I see my crew, my team, my fellow soldiers in the trenches, and I realize that there is nothing like being on set. Read more>>

Zihan Zhao

I had a full time job as a singer/musical theater when I was in China and I didn’t know any English. It was a big challenge and risk for me to move to the US. But I really wanted to take the risk as I just simply enjoy it. I know I’m adventurous in the way that I would challenge myself without knowing the outcome, or I wanna say that I always think things will work out at the end. Although it’s not all true. With the tremendous language barriers, all the skills that I had in China couldn’t work here in the US. I had to go to a community college to learn English which means I had to take years of break from my professional career. But somehow I knew this would be a very an exciting journey! And indeed, it has been very exciting to me. I met good friends and mentors during this journey. Read more>>

Jamie Buttars

Opening this coffee shop was a huge risk. After attempting to start and then failing at operating three prior businesses, of course I was apprehensive to try again. However, I knew if I wasn’t willing to try at least one more time, the chances of me failing at it would be 100% Very early on Mindie and I decided we wanted to do everything we could to give back to our community, the first big one being my idea to host a free Thanksgiving dinner for people in our community that could not afford to have one, or for people who didn’t want to spend the holiday alone. Every single person told me it was a bad idea. Read more>>

Birgit Huttemann-Holz

Taking a risk is the fastest way to learn something new and to be propelled forward in your life, your aesthetics, your experience. Taking a risk is an immanent step in the creative process. It is being curious and fascinated by the challenge, the possibilities, the steep learning curve in failure. Accepting the unexpected and working with it is the path to progress. To be an artist is to be courageous, to be a risk taker. Every day, I enter my studio and let go of expectations. Read more>>

Jenny Day

Over the last few years as an artist I have primarily made paintings and sculptures. Recently I have expanded my artistic practice to include a massive installation, A Feast To Remember, to be exhibited in December 2023 at Alabama Contemporary. It has been a long term project that has required learning new skills, getting help from other artists, and being open about the finished product. It has been uncomfortable and there have been many failures. It has felt like a huge risk to not think of myself as a painter or sculptor but as an artist. To be open to any material that needs to be used to express an idea. Read more>>

Monica Bell

Embarking on the journey of starting my own practice and leaving behind the comfort of a stable job has proven to be one of the most rewarding risks I’ve ever taken. I made the bold decision to step away from my position as a cardiology nurse practitioner at a local hospital clinic and venture into the realm of Optimal Hormone Health. Years ago, my fascination with hormone replacement therapy took root, fueled by the compelling evidence of its myriad benefits in mitigating the effects of aging. In my 40s, I faced my own hormone challenges, prompting me to embark on a personal hormone replacement journey. The transformation was nothing short of life-changing – renewed energy, increased libido, enhanced concentration, and reduced anxiety all culminated in a profound sense of wellbeing. Read more>>

Martha Frassica-Rivera

The biggest life changing risk that I have taken was purchasing the land that the Everglades Outpost Wildlife Sanctuary runs out of and taking over the sanctuary and continuing the mission with my family. This all happen two weeks before the shut down due to the pandemic in March of 2020 so it was a big emotional and financial risk. A little back story on how this all came to be! My husband and I began to volunteer at the Outpost over 12 years ago. We became very involved with the sanctuary, leading to me eventually leaving my job in the human ER to fully take on the management role of the sanctuary as the founder was caring for his terminally ill wife. When she passed away, we all sat down and discussed what we wanted to happen to the sanctuary and my husband and I agreed to take on the responsibility of running the sanctuary. Read more>>

Kady Hinojosa

Publishing my first book, #HuntedLives, was a risk because I was putting myself out there when I am usually a pretty quiet person with folks I don’t know. Writing the thriller was the easy part. The first time I attended a market days in the Texas Hill County, as a vendor, was scary. I was definitely out of my comfort zone. It was the same when I spoke in front of a group of people for the first time. It was a risk and it forced me to accept being uncomfortable but doing it anyway. And now I really enjoy the events I do, whether speaking in front of a group, signing my books at our local bookstore or the library, or meeting folks at various market days. It’s fun. The risk definitely paid off. Read more>>

Elyanna Wyatt

Starting this business was a huge risk for me. K-Pop is not very popular in the Ohio and I really didn’t think people would be interested in anything related to it. I have never started a business before and I didn’t think it was possible. Before I started CincyPop, I was a college student working a part-time minimum wage job struggling with depression and anxiety. I really wanted to do more with my life but I did not know where to start. When I was at my lowest I got the idea to create a space for people who like K-Pop, like me. I noticed there wasn’t a huge market for it in the Cincinnati. I was not sure if anyone would notice or care. Read more>>

De’Viar Woodson

BLACCENT got its start in the world of politics. Raising awareness and using our collective voices, to join millions in outrage – over the murders of George Floyd, Breonna Taylor and Ahmaud Arbery. The back to back protest/rally were undeniable successes – and everyone, including us, were asking “where do we go from here?” We now opened a Pandora’s box of responsibility, and honestly, at the time, we didn’t know what we were gonna do next – we just knew we needed to do something. Read more>>

Shanik Hughes

In this interview, I will take you on a journey through my life – a life defined by risks. From moving to a different country at the tender age of 12, to choosing a career path with no certainty, risk has been my constant companion. Throughout my journey as an artist, I’ve embraced risk in every step. From portraying diverse characters in various movies, spanning musical theater to soap operas to film, I’ve dared to explore uncharted territories. Read more>>

Allison Gordon

I had a moment where I kind of “re-thought” my life. I was unhappy with the road I was on and wanted to be on was a sacrifice and was very stressful for my personal life. I remember my fiancé and I taking a vacation to the Smokey Mountains, and I was sitting in the beautiful mountains by the river. I thought to myself, “I don’t want to go back to my stressful life back at home.” It was then that I realized I was on a path I didn’t want to be on. I wanted to take control of my life and do what I wanted to do. Spending more time with my kids, because, let’s face it, we aren’t here forever, was very important to me. Read more>>

Brian Smith

I’m generally conservative in nature which leads me to be fairly risk averse. But many years ago I took a big one that, looking back now, had a big influence on my life today. I spent my high school and college years in small midwestern towns, and my first job out of school was in another small town. Despite being close to family, having a good job, and getting good work experience, I had a persistent feeling that I wanted something different. The only two specifics I had in mind were a warmer climate and the excitement of a bigger city. After feeling this way for a couple of years and living through another cold winter, I made what seemed to many to be an abrupt decision: I quit my job and moved to Houston, Texas. I had a little cash in the bank, and everything I owned fit in a mid-size car. Read more>>

Mercedes Cherelle

My name is Mercedes Cherelle. I’m a master cosmetologist specializing in healthy hair. Not only am I a cosmetologist I am an author of a book called, “More to Natural Hair Than Just an Afro”. I also do a natural hair health and beauty expo once a year “Saecher Natural Hair Health and Beauty Expo” located in Rockford, Illinois. Every year that I put this natural hair health and beauty expo together I am taking a risk. I do it for the love of the Caribbean culture and natural hair and also promoting self-love and appreciation to women and children no matter what. Shape, size, skin complexion or hair texture you have. The risk that I am taking is the responsibility of ensuring that this event runs the way that it should. Read more>>

Laela White

I decided to take a risk on myself and apply to grad school for my MFA. I wouldn’t say it was a spur of the moment decision because I had been mulling over it for months at that point. I started my application, did all of the admin stuff, but when it came time to upload images of my artwork, I felt stuck. I had photos of my work, most of them on my public portfolio and some as unshared files in my computer, but something was preventing me from uploading my photos and finishing that last step needed to submit my application. Read more>>

Matthew Lucas

I think I’ve taken many risks as it relates to my business. I moved from the city to the suburbs and decided to make a change from part-time to full-time. The pandemic certainly altered the industry and I also added virtual training (still a significant portion of my business). I also finished my beautiful home gym. All of these were risks I took, but I have persevered and grown my business substantially. I’m thankful for all my clients that have trusted me with their health and allowed me to do something I love in the process. Read more>>

Tara Willey

Not only as a creative, but as a human being, it’s necessary to take risks. It’s rare that we make a choice in 100% certainty. It’s nearly impossible to know what the outcome will be when we take a risk. But if you give yourself permission to take them, I promise you’ll be given gifts you couldn’t have been given if you stayed put. You owe it to yourself to take chances. So often I’ve held myself back from opportunities because I convinced myself I wasn’t ready yet. When we go for anything in our lives, sacrifice is unavoidable. We must face it with bravery. The lives we want to build inherently cost us our current one, in some ways. We’re scared to take risks or trust our path because we focus too much on the things we may to lose. But what if we focused more on what we could gain? Read more>>

Alexander hallowell

The biggest risk I have taken in my life has been the decision to try and make music and DJ as a full time career. It all began with the idea that making music was the only path in my life that I wanted to take and that there was not going to be a plan b for me. I believe in life that I you want to become something or complete a goal you cant have any other options for yourself and that you need to remain focused on the single goal you set out for yourself. As I got more serious with creating music specifically I knew I had to buckle down and take it as serious as any other job. It has been as tedious as it is gratifying. Read more>>

Thom Allen

As a psychotherapist, one of the most profound risks I have taken was when I made the difficult decision to close my company’s physical location after more than 30 years and pivot to offering counseling virtually. Taking the leap from seeing my clients in person at my cozy office to embracing the world of remote online therapy was a risk that changed my life and my practice. Doubts and uncertainties weighed on my mind as I pondered the shift, concerned that the intimacy of face-to-face interactions might be lost in the digital realm. However, the yearning to extend my reach with the deeply meaningful work that I provide pushed me forward. Read more>>