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.
Britney Robbins
The biggest risk I’ve taken thus far has been quitting my job in 2016 and starting my own business, The Gray Matter Experience. I knew that I was ready to leave my full time job but was clear that I didn’t want to move into another full time employee role. I really enjoyed the work I was doing, but didn’t want to stay at the company I was with either. While I had never started a business before, I had been teaching entrepreneurship for the past 3 years and understood the basics of what to do and had a strong calling to have a deeper impact in the space I was already within. Read more>>
Melanie Shafranek
The first seven years of my career were spent in the photography industry as a creative in a field I sometimes felt like I didn’t belong to. From the ages of 23-29, I dealt with chronic symptoms that guided me down a path to health I never expected. I always knew helping people was something I was passionate about, but until I went through my own health crisis, I didn’t know being a Functional Nutritionist was actually my calling. For years, I went to work exhausted, dealing with food sensitivities and symptoms, surrounded by people who didn’t understand what I was going through. Read more>>
Gen Palmer
18 months ago, with help from a mentor I raised prices significantly and changed my company’s service offering from a “middle-of-the-road” all-inclusive model to a custom, luxury experience. It was a bold and scary risk at the time because it goes against what many clients expect of the photography industry. I knew I would lose clients because of it, which I have, but I didn’t realize I would gain so many new clients and fans for life because of the change. Read more>>
Adam Bucciarelli
Our local scene in south jersey had been so good to us through the years, but we always wanted to give the west coast a shot. Our focus shifted in 2009 to moving to San Diego. It was a much bigger market with a more diverse music scene. Fast forward to 2011 and the band was booking gigs and making its way into the San Diego circuit. Relocating across the country for a band was very risky. Any number of things could have gone wrong. Pulling double duty with getting acclimated with a new area and the band was very stressful. But we believed it was a necessary step to continue to evolve the band. Read more>>
Ryan Matthieu Smith
I take risks every day. Some big. Some small. This practice has become so instinctual that it may go unnoticed, but the reward is always the same. I make the choice to live as boldly and with as much authenticity as possible. This is the one thing that no one can duplicate. My brand of magic is not for another person to make. And neither is yours. Read more>>
Ashley Nicole Marshall
A year ago, May 2021, I left the school system. I am a certified teacher for Texas in grades Prek through 6th. I taught for 5 years certified. When Covid hit, I felt a shift coming, just like so many others, to make a career change. I had already established my Candle Company, BellaPearl-A Candles, while working. On the weekends, I was participating in every vendor event I could find. Once I reached the money to pay my expenses every month, I said, okay, I’m walking away from my salaried position. That step is the biggest step, because you are stepping out of a box, stability and comfort. However, That was the best decision I have ever made. Read more>>
Mike Howard
Without risk there’s no reward. You hear it everyday! That goes for almost anything you do in life. I was 30 year olds with a family, newborn son and wife to be exact when I took the biggest risk of my life. I started my first company and decided it was time to go all in and exit the corporate life. I quit my Job that summer and was full time on my own business. It was the scariest decision and biggest risk I have ever taken, but I knew the potential reward it had. Read more>>
Kristen Kurtz
My husband and I both came from families that valued hard work. The only way you “might” get ahead in your life is through the hustle and maybe some good luck on your side. We were taught that financial success didn’t come easily if at all. I had just turned 30 years old and we lived on the island of Kauai. A home in our dream neighborhood became for sale. We would drive by the home multiple times a day and talk about how we could possibly own this home. We had very little money for a down payment. Read more>>
Patricia Parks
Life throws curve balls. How you respond to those is everything. The vision of creating a space for creatives to flourish and earn a living at their craft was not something I had planned. It just came at me like a “curve ball.” My life had changed for the 100th time when I reconnected with an artist I knew in high school; Michael Roser. His work is amazing; seriously, genius. Read more>>
Abbigail Staples
I have trained in my sport for almost 4 years. About 2 years ago, I took a break from training kickboxing to focus on Jiu Jitsu and competing. In January, 2022, I accepted a kickboxing fight short notice ( like a week before the fight) and my coach was not able to go to Oklahoma with me. My grandpa took me to Oklahoma, I had a physical , we got my fighter’s license and got taped up to fight. It was one of the most exhilarating experiences of my life! My adrenaline was pumping and I finished my FIRST ever amateur kickboxing fight with a WIN! It is experiences like this that keep me wanting more. The adrenaline rush is the best thing ever! I have my second sanctioned fight coming up on June 18th! Read more>>
Alavia Khawaja
Taking a risk is always scary, especially when it’s personal art. When I first started my clothing business, I did nottt want anyone to know that it had anything to do with me. There are so many “what if’s”. “What if my designs suck? Or worse, what if I genuinely liked my designs but it turns out everyone else thinks they suck?”, “what if it isn’t original enough”, “what if nobody buys anything”, “what if people think I’m a try-hard”, “what if everyone watches me fail?”. Read more>>
Diego Morales
I worked hard all of 2019 to build up my brand and take my comedy on the road professionally. I had dates booked for the year of 2020 up until November. This was January 2020, Kobe was still alive. I took a risk with my stand up comedy career and my well being when I quit my day job of 11 years to pursue comedy full time. Then the world decided to stop. So, my last day with a normal day job was the last “normal day” pre pandemic – March 13, 2020. I was forced to give back a lot of advances and deposits. My old day job gave my entire department a severance check worth 6 months of salary on one check 2 weeks after I quit. So I called my old job and told them I was just playing about quitting, they didn’t believe me. Read more>>
Ashley Miller
The biggest risk I have ever taken is finishing cosmetology school and moving to Texas from South Carolina within three months. You may ask why that is risky, but as a new stylist you depend on family and friends within your home community to help build your business. When I took the risk and moved here, I became involved in many of the “social media mom groups” and became obsessed with my online presence. I even went to every single business in the town I moved to and handed out my business card with a discount attached to the back. Read more>>
Jennifer Terrell
Risk—this is a word that many people run from mentally when they hear it or think about it. Even so, I do the exact opposite when there is something that I want to pursue. A risk that I took was becoming a business owner. Many people think about opening a business, but they lack the confidence that it takes to pursue this goal. For me, I took my love of cooking and turned it into a restaurant. Time and time again I had my family, friends, and community members express their love of my recipes, and how they loved the taste of my food. Read more>>
Susan Semmelmann
I have always said, you will never know unless you try! You have to convince yourself starting out with nothing at the beginning that you have nothing to lose, and the biggest challenge is being willing to fail! I have a different approach than a very studied, educated decision maker. I launched my own brand 3 years ago on pure faith! Thats it! I felt the call to go out into the world and had no vision other than freedom in store. I only wanted to do what I love to do, design. I had a hand full of co workers who believed in me and wanted to do what they love, sew, design and encourage each other from the ground up. Read more>>
Dr. Sharmee Pratt
I believe one of the best client advice I have given was to teach them it is okay to say no and to learn to put themselves first. So many times people struggle with understanding that they matter in life. To help people to understand who they are outside of what they do is a challenge for many in life. I have had to help them to tear down blocks in their understanding that everyone else comes before them. When an individual has lived their life based on their function meaning what they do or have done most of their life it becomes difficult for them to understand who they are out side of how they function. Read more>>
Jennifer Martinez-Duque
It was a small risk I took I had no clue how to start a business or how to go about marketing. Luckily my cousin Stephen Who is an entrepreneur showed me how to get started and how to market my business. With his wisdom has help me grow . Read more>>
ALEX KAUTZ
Taking a risk is one of the most important things I’ve went to do in life. I went to business school briefly and learned in a marketing class that the best thing you can do is trial and error. You have to see what works for you as a brand and filled off of that. In my experience, Writing songs that might take the listener out of their comfort zone – but are authentic to me, are the songs that work the best. Read more>>
ROYCE SOBLE
One of the biggest risk I took was a professional one. While I was getting my BFA degree in Photography, I had worked in the restaurant industry. I stayed in the industry for 20 years while I built up my career as an artist. The last “real job” that I had was working for an amazing restaurant called La Tavola Trattoria. I worked there for 14 years and I loved my job. I started off as a server the first few years and then became a full time bartender the last decade. I had an amazing clientele who were loving and loyal customers. It was a neighborhood favorite, so people would come at least once or twice a week. These folks were like family and they also supported me as an artist. Read more>>
Tyra Mitchell
It was March 2020, I had given my all to my former employer when I turned in my keys to the store and stepped out on faith. I didn’t know where I was going to do for work but I knew that God was going to provide. Never had I walked away from any job. This was different and I had peace behind my decision. The night before I had spoken to my district manager via text message about me switching my shift. Instead of me opening I needed to close. I told her that I had a shift manager that agreed to switch with me. Read more>>
Caroline Young
I learned at a young age that following my intuition and my heart also meant taking risks. It also often meant going in the opposite direction of what many of my peers were doing or of what my elders were advising. And the hardest part — it meant enduring discomfort as I took the leaps into the unknown. It’s funny — I’ve had people tell me I am fearless. I always laughed at this because I am certainly not fearless. All of the risks I’ve taken thus far have included hefty amounts of fear. Taking risks is about being afraid and doing the scary thing anyways, because it is the path that feels the truest. Read more>>
Britt Vasina
The biggest risk that I have taken in my career as an artist was really just sharing my work in the first place. I created an instagram account (I think in 2017) to just post photos when I started painting again. I figured it would be fun to look back and see my progress. To my surprise, I had family and friends who wanted to buy my work and encouraged me to continue painting. What started as a therapeutic way for me to ward off anxiety had suddenly become a business I never knew I wanted. Read more>>
Jaszy Shavers
Pursuing your dream or heartfelt purpose is always a risk. For a calculated individual as myself it was a huge risk but thankfully I have no regrets. Going full-time with my music was one of the scariest decisions I’ve ever made. It seemed unrealistic, untimely and unpromising to be honest. Many people didn’t understand or even support it and the journey has shed much light on who/what really matters to me. It wasn’t flowers and sunshine for a while because not only did I do it on a whim but I also did it with little resources. I had and have a very small support system who truly wants the best for me but through thick and thin we always make it shake. Read more>>
Gabby Emslie
In 2020, when Covid started and everything shut down, I was forced to make some hard decisions regarding my future. I decided to homeschool my daughter, who was 6 at the time, which meant I had to quit my job. I had worked at a bakery for the past 6 years, and leaving was not easy – I wasn’t sure what I was going to do for work. Luckily, my partner Beck was there to support me through everything, and I was able to homeschool full-time while also figuring out what to do about my income. Read more>>
José Miguel Mike” López”
Back in the year 2010 there was a call for a contest, organized by the Stan Lee Foundation through talenthouse.com. The idea was to create a superhero with all of the character traits of one. The winner would have the chance to meet the judges, Stan Lee and Todd McFarlane, and would also have the opportunity to publish his/her superhero story. I entered my characters in the contest. They were inspired by real-life actual events that are of extreme importance not only for our planet but for us as well and that teach us who we really are. Read more>>
Shannon Low
Risk, well there are surely some people out there who would say that while I like consistency I have taken my fair share, some good, some bad, some ugly. It may be evident in the story of Great Heights, that starting it was a series of risks I took that I wouldn’t call good, bad, or ugly, rather purposeful, hard, and educational, but as the work I did with Great Heights shifted over the past year I of course needed new excitement, because what’s life without risk? Read more>>
Yari Mena
My risk taking story starts with me taking quite literally no risk at all. I had just graduated from GSU with an art degree in the summer of 2019, thinking I would try to find a job at a museum. I was at the time, working part time at a non-profit organization to pay my bills as a student, sort of bouncing around programs and sites. When I graduated, I was asked what my plans were, did I want to stay and work on an healing arts project- which would be a very small part of my job, or was I planning on leaving and seeking work elsewhere? Read more>>
Mighty Tim Young
Risk taking, I’m convinced, is an essential facet of being an artist (in any field). My artistic and personal life have been layered with risk taking. The summer following my graduation from Mansfield State, in Pennsylvania, I was married. Five years later I was able to convince my wife it was time to move to New York City to pursue our dream of the actor’s life. We had both studied theatre at Mansfield, where we met. Read more>>
Daniel Knoll
I quit my job during the pandemic to start my photography business. It was one of the scariest things I’ve ever done but it was the best decision I’ve ever made. I was working as a property manager at the time and doing photography on the side. When the world shut down and everybody was watching Netflix and learning how to make bread I got right to work. I spent everyday on all the back end work of starting a business and when I wasn’t doing that I was taking as many photos as possible. Read more>>
Matthew Griffin
I was a beverage consultant for a restaurant group in Oklahoma. The position was designed for me. I would change the cocktail program for multiple locations and assist in training their staff. It was a really good job with an incredible company. I left that company and took an hourly position as a bar back in Tulsa. Why? Risk. The job was incredible but I felt like I was beginning to piece myself together bit by bit. Read more>>
Aaron Roberts
Betting on yourself can be one of the hardest things to do. You have probably heard before that the hardest part is taking the initial leap. And that’s not wrong. Quitting your day job. Dropping your savings on an investment in your business. Leveraging capital investments and credit card lines to keep you afloat. Whether it’s a small video business, a restaurant, a clothing line… the risk of “losing everything” is what usually stops people from ever taking the leap. Read more>>
Mo Lima
Risk taking is healthy – It’s part of a life well lived. I’ve taken risks all my life. Some measured and others dramatic. Moving from New York to Atlanta was a risk. I was 31 years old with a small child. We were so used to small apartment living that we never noticed. I never learned to drive.. ‘Cause in the hustle and bustle of Manhattan—the “concrete jungle,” few people have or even want a car. But I needed something different in life—a chance for change, growth, and it was a wonderful risk. Read more>>
Sarah Lightman
I’ve taken a good amount of risks in my life so far. I’ve risked my safety, my bank account, my career choices, choosing to fall in love completely, choosing to accept failure, and even chose to have vocal surgery during the pandemic in 2020. However, the biggest risk to date I’ve ever taken, which may sound incredibly cheesy to some is committing to love myself 100% and consistently. Read more>>
Kemoni Williams
I have been doing music originally as an Artist since I was 13. I never had a lot of money as a kid so I did not go to professional studios, mainly because I always thought that somehow you had to be famous to go to one and it would be expensive. So, I did what I’m sure a lot of kids in my situation did, go to Walmart and buy a mic, then shop around for some free daws (Music Maker at the time). I have always had a passion for creating music, However, I never took it seriously or even had the means to do it. Read more>>
Molly Drake
I imagine many other business owners say this same thing – but going full-time with my business was just about the biggest risk I’ve ever taken! I’m a self-taught graphic designer. Everything I know I learned from Google, YouTube, hands-on practice, and a few semesters of online design classes from a local technical college. At my last job, I was part of a very small management team at a local restaurant/brewery/private event space where I had a lot of leeway to take on new projects and responsibilities that I believed would help the business. Read more>>
Moon Taylor
Growing up on the farm I’ve always had the pleasure of dealing with animals, But as an adult I wanted to carry that passion further but wasn’t given that opportunity until later in life. It was just one day while bottle feeding domestic orphan kittens I realized I missed working with animals and wanted to be able to do more, so I started to do research on wildlife and what it would take to be able to rehab and help the wild animals, during my research i found out that you have to have certain license and training and classes and in addition to certain supplies and equipment and their was no financing available, So I had to make a decision and choose between giving up because I’m a single mom or take a big Risk. Read more>>
Lizzie Hillard
After marrying my husband, Keaton, in April 2021 at just 18 and 20 years old, we were just getting our feet off of the ground! Keaton decided to start his own Handyman business the day after we got back from our honeymoon! Soon after, his business took off and the Lord blessed and provided for us in every moment. I was still unsure as to what route I was going to take job wise! Being new to Texas, I was striving to plant my Photography business’ roots in Tyler; deep in a passionate community full of like-minded creative entrepreneurs! Read more>>
Hannah Ricke
I like to endanger myself every so often, and my story of BECOMING MYSELF started with a big one. I was finishing a Masters in Clinical Social Work (mental health) when I knew that my reserves were depleted and I needed to turn my deserts back into the lush rainforests they once were. So I decided to undertake a momentous backpacking trip. Mexico to Canada, along the wilderness path called the Pacific Crest Trail. Read more>>
Kyle Asperger
As the creative director, my job is to make sound creative decisions on behalf of our clients. Decisions that will inevitably push them toward their established goals. The hard part is seeing when creative decisions need to be made internally for my company, Studio 301. Risk vs. reward. Will the reward outweigh the inherent risks of the proposed shift? Read more>>
Nina Obier
It was 13 years into my corporate career. My husband and I had recently bought a new home and a new van. We wanted and new neighborhood for our daughters to grow up in. They were 6 & 4 at the time. Both of our incomes were necessary to keep a roof over our head. Alongside my mom, wife, work, family member, friend duties I had taken on a hobby that I loved, scrapbooking. We were so happy with our decision to move. Read more>>
Jim Stevens
I was shot in the head in Vietnam and it left bullet fragments in my head. Twenty-three years later, one of those fragments caused a stroke in my visual cortex, taking all but a pin dot of my vision and leaving me legally blind in just 30 minutes. I lost my job teaching at the University of Colorado, ended up divorced and was suddenly the blind single parent of two pre-teen daughters. I also stopped doing the artwork I had loved so much. My bouts with depression and anger were crushing at times, so much so that I destroyed most of my unfinished art, notes, drafts, and records. Read more>>
Lisa Gunshore
As an entrepreneur, I have taken many risks. The invitation to be adventurous comes daily since the 2020 pandemic. It was March of 2020 that I pulled together the women who supported me during my journey of self-discovery in order to provide global support. I had never been on YouTube and I had never been live. I did it and the first One Heart One Earth Global Healing Summit was produced. Read more>>
Bernadette Youngquist
Risks come in all shapes and sizes. I know people who are really excited to take physical risks that I can’t imagine taking. For me, risk means standing strong in who I am as a person and feeling confident in my decisions. Allowing myself to be vulnerable to others is a risk I take in my art and on social media regularly. As I began to explore my creativity I did it in tiny steps and in safe ways because I wasn’t ready to risk vulnerability. I am now at a place in my life journey where I am okay with standing in what I believe in because I know it is true for me. Read more>>
Ali Stone
When I graduated in college with an English degree, the country was in the middle of a recession. I cycled through a series of retail jobs before I found myself in my first B2B marketing role where I began mastering skills in digital marketing, content development and online branding during the time of the “internet of things”. Over a course of 10 years, I worked in a variety of B2B marketing and communications roles at global companies and PR agencies. While I loved the tactical work, Read more>>
Narvie Madison
I worked in Corporate America for 10 years. In 2020, I lost my mom and my job. I decided to pursue my passions and create content showing my life with my piglet. We travel in our camper van and explore as many new places as we can. It was the best decision I ever made. My mental health is a million times better. I’m learning valuable life lessons and figuring out how to navigate life without the support system I depended on for so long. It’s been a wild ride, but worth every minute. Read more>>
Natalie Tuman
I feel like I’ve taken a few risks along the way in my journey. The first risk I took was when I left my full time corporate career in business development for a large hospital organization. I was doing personal training and running a boot camp while also growing my online health and fitness business. I had 2 young children at the time and sat outside of the hospital every day with dread and a knot in my stomach. Not because I didn’t love my job, but because I knew that I was being called to more purpose. I knew what my heart’s desires were and it was to do health and fitness on a full time scale. Read more>>
Christy George
Taking a risk for my business was the biggest risk I’ve ever taken. My husband and I put everything we had into taking over ownership of Bronzmopolitan Spray Tan Bar. I am grateful every single day we decided to live in faith and not fear. We took the leap and I am so happy we did. Owning a business is a ton of work, non stop, but I could never go back to working for anyone else but US! The previous owner, Bethany, was so wonderful and full of knowledge when I started here as a Spray Tan Artist, Read more>>
Kameel Gaines
We all talk about how taking risks is a part of doing or running a business. But they don’t tell you how to calculate the risk to maximize results. Typically it is done by trial and error. I do believe in taking risks, but they must be thought out. Rig on Wheels is a freight broker and truck driver recruitment agency. The core of what we do is find Class A CDL holders their ideal job. ROW has a recruitment team in the US and a recruitment team in India. Both of them recruit American drivers to drive for American companies. Read more>>
Kelsey Barnes
The biggest risk I’ve ever taken was allowing people in. Spiritually it’s always risky to be apart of a group of even a leader of it because it’s so much energy that has to be fed others. Dealing with the masses alone and being a voice is a fulltime job Read more>>
Ian Burse
It was summer 2019 i believe and I had the opportunity to film a pilot tv series to be pitched to major networks. The budget was very low but I was willing to grind to get to the goal of being a DP for a major tv series. I had 2 weeks to build a team on a low budget and managed to get one. We filmed the episode and I did an extra day for free because we couldn’t finish it in the time allotted. Then once filmed, I had to edit it. I had limited time to edit a 40 min episode because I was also working full time. Read more>>
Lyndsy Foshion
The biggest risk I have taken so far in my career was when I left my commission salon and starting working for myself. At the time I had only been in the hair industry for 5 months, and hardly had enough clients to support that move. But it was one that I knew in my heart I needed to make in order to grow as a stylist and business owner. I was terrified at the time, and I just remember telling myself “if you build it they will come” and it’s so true! I did a deep dive into my branding and started working really hard on my social media to attract my dream clients. The growth I experienced was amazing. It was such a scary risk, but it paid off immensely and I am so grateful I did it! Read more>>
Akasia Lee-Nicholas
They said it couldn’t be done! Returning Mardi Gras to the Westbank of unincorporated Jefferson Parish for the first time in 30 years….. they said it couldn’t be done AND WE DID IT! Defied the odds, pushed through and made Carnival history on 2-22-22! Read more>>
Sarah Anderson
Taking risks are what make life interesting, and define our destiny in many degrees. I grew up in Kansas City Missouri, where it was not a real risk to stay where I was raised, but little to my own memory I was already manifesting one of the biggest risks in my future at age 7. My Mom recalls ” I knew you would go to Dallas one day, when you were 7 you told me you would live in Dallas Texas when you were older.” Not knowing at that young precocious age, in my mid-20’s I would do just that. Read more>>
Joey Da’Mauro
Well in 2019 I was living in Tampa Fl , I was so depressed living there. I just didn’t mesh well with the city. But It had always been a dream to move to California, to chase my dreams. Then one Monday morning I was watching TV and a. “Move to California “ add was on tv. So I said F—— it sold everything in my apartment and left by that Friday. No job just savings. Now I have 2 great running businesses. That was the biggest risk of my life. Read more>>