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.
Kristi Brooks

I understand my decision to become a full-time Wedding Officiant and PreMarriage Coach, is a HUGE risk from the outside looking in. With the ability to get ordained in 5 minutes online, there aren’t many of us out there that choose this job for a living. But what others see as taking a risk, is my total leap of faith. When you’re “called” to something, I believe you have a responsibility to answer that call, even if some find it ridiculous. Read more>>
Bryce Loewenstein

When I was 17, I was faced with the option to go on a month-long tour singing for a band out of Omaha I had never met. After facing the expected backlash from my High School (in which my senior year had just begun), I went for it and my life never looked the same again. Still got that diploma later, though! I learned valuable lessons of the road and who I was as a rebellious, teenage human planted on this random space rock spiraling about. I HAD to take this risk and break away from the societal ‘norms’ pressured upon our youth. Read more>>
Amy Cavanaugh

I have been the Executive Director at Maryland Art Place (MAP) in Baltimore City for a decade as of this year 2022. When I first took the job in 2012 I was told by my Board that we were to sell our property across the city because it was deemed and burden to the organization financially. They weren’t wrong. MAP’s beautiful west side building needed a lot of attention at that time, and our leasing initiatives were barely getting us to even. Read more>>
Shannon Whittington

Years ago when our children were little I always had a camera with me (people I didn’t know referred to me as the lady with the camera lol). Other Mom’s at events would say “I forgot my camera would you take a picture of Susie or Johnny”, and I would and then give them the printed pictures (that was before digital). After a while of that my husband said “thats expensive” why don’t you create a website. I did but that didn’t do to much,lol. As I began to have people ask me to take pictures of their children that grew…. Read more>>
Katie Reid

I feel like being an artist is a risk. Financially, you could spend a couple hundred on a painting including new supplies, only for your work to never sell. Now you’re in the hole. That’s what’s most terrifying, the risk. Before you even finish your work, it isn’t successful. However, that feeling when a painting is successful makes up for it immensely. All your hard work and time you’ve put in, finally being appreciated makes up for the fear, and risk, of failure. Read more>>
Iris Mendez

In 2020, at the brink of the pandemic, I took a risk and quit my job as a psychotherapist/EAP counselor. At the time, I believed it to be for good so that I could focus on my mental health, healing, and also take a leap into my wellness business which I had began in 2017 but worked part-time/freelance. This was one of the most profound moments for me as a single woman with no other finance supports. It was the first time in my life since high school that was not working for anyone else. Read more>>
Chaneya Joyner

I think there are two separate moments that come to mind when I think of taking a risk. The first is getting in to blogging sharing content on social media in 2017. I’ve always loved clothing and fashion and waited a long time to just take that leap. Sharing yourself on the internet is a super vulnerable thing because you’re opening yourself up to comments and criticism from complete strangers. Luckily it has only been a rewarding thing in my life and a fun outlet for me, a complete 180 from my 9-5. Read more>>
Angie Williams

Every business owner, no matter the industry, will tell you that with success comes struggle. If they say owning a business is easy, don’t do business with them ! Being an entrepreneur is about taking risks , assessing the risk vs benefits and becoming successful. When Intentional Hairdresser Workshops was in the infancy state , I struggled with pulling the trigger. I knew that I had experience and knowledge to give share and I knew that others were offering similar services , but I had a hard time believing in myself and that people would want to hear what I had to say. Read more>>
Deidra Murphy

When I decided to pursue my career as an actress, my biggest risk was making a decision to drop everything and move to a whole different state. From Ohio to Georgia. I am very proud of my decision. Taking risk makes life fun! Life is so short and I decided not to live in fear anymore, to no longer allow everyone in my ear with opinions on my dreams, My dreams are mine. So I just grabbed all of my things, my children and just went. I was a bit scared of course at first, but then I decided to just live in faith and not fear. Read more>>
Nick Saenz

Since college, I continue to take the risk of financing and creating my own short films. It’s led to disastrous results of having to start my life over again and again. A few examples, I made a feature film after graduating college, and everyone (small group of friends) was on board for the project. They were in love with it. Took years to finish. It went nowhere, bombing hard at the festival circuit. Had to go back lay low for a while (with my parents). Then I tried to have an ongoing improv show but luckily that idea was cut early due to the Pandemic (COVID-19), then my hours got cut and went back to live with my parents. Read more>>
Erika Andersen

Risk is an interesting topic which I love to discuss. My husband and I listen to a podcast called “How I Built This” hosted by Guy Raz. In one of the episodes he interviews the founder of Sam Adams Brewery, Jim Koch. Mr. Koch discusses risk in a way that changed the way my husband and I view risk and as a result, how we plan and live our lives. Because of this podcast episode, we look at risk as being either scary or dangerous; in this context dangerous doesn’t just mean physically, but could mean emotionally, financially, etc. Read more>>
Girl at the Rock Shows

I had a great day job up until about a year ago. It wasn’t glamorous– it was literally selling nuts and bolts at a fastener supply company– but it was perfect for me. I love my co-workers, loved the family that owned the company, and loved all of my customers with all of my heart. Although I loved it, I felt restless. It was actually a co-worker who sparked this whole idea of starting a blog about my concert adventures (that’s a whole other story) and, as soon as I started it, I felt a sense of life that I had been missing. Read more>>
Leslie Gourley

The biggest risk I have ever undertaken was purchasing Decatur School of Ballet in 2018. I was in my mid-50’s and I had had a fairly successful career as dancer, teacher, choreographer and company associate director. My husband and I had finally gotten to a place where we weren’t feeling the struggle every month. Our daughter (who is a professional dancer in the Atlanta area and a teacher with our school) had graduated college, so that hurdle was behind us. Then this offer was extended, and it felt like it was something I could not pass up – at least I had to try. Read more>>
Brianna Campbell

Opening a business is a risk. It could be the best or worse decision of your life. I started my business (Lacy May Boutique) the year after graduating high school and in the middle of covid. The future was unknown to everyone in the world and making the decision to start a business was one I hoped would be one of the best I”d ever make. Today I still regard opening Lacy May Boutique as one of the best decisions I have ever made and I am hopeful that it will continue to grow into what I know it can be. Read more>>
Jowand Brown

One of my life changing risks was leaving a barber shop surrounded around seven other great barbers to open my first studio at Sola Salons located on south side of Savannah. At first I was scared because I didn’t know how things were going to go, but I had faith and prayed everyday about it. Read more>>
Amy Rivera

I was born with a rare disease called primary lymphedema. All though I know what it is called now, that wasn’t the case for most of my life. I was misdiagnosed for over 30’s years. As I grew, so did my right leg. At its worst, it was 200% larger than my left leg – leaving me disfigured and alone. In 2013, I started my reduction journey and fought for my life. I used to wear long dresses and skirts to work so I could hide my right leg. I asked a co-worker if she wanted to go swimming. Read more>>
Kristen Raymonds

Investing in my dog walking pet sitting business was a big risk. I am a single mom who has years of medical experience and I had a corporate job with possibilities for a promotion and more income. I wasn’t happy at all. When the pandemic hit I took time to do some work on me and explore the reasons I may not be happy. Life in general can be a lot and it catches up with us. I wanted to make a change and I wanted to work with animals but I am risking comfort in a life I may not be happy in but felt safe. Read more>>
Ronkeia Lewis

Where can I even start? My background is in health and wellness and I’m currently a cooperate wellness coach. I’ve dedicated most of my life to helping people, so stepping outside of sports and health was new to me. I never imagined that I’d be an author or a speaker. I always knew I had a niche for helping people, but walking someone through what can be a spiritual journey was not on the menu lol. This project came about from me building my relationship with God. I always felt as if I was built for something greater, but could never put the pieces together. Read more>>
Carly Heasley

“I work for myself.” The phrase I keep practicing over and over again. I just quit my job – a job I loved, a job I was good at, and a job that inspired me. A lot of you are probably wondering, “why?” or thinking to yourself “that makes zero sense.” Trust me, you’re not alone in those thoughts. I’ve asked myself “why?” a million times. Read more>>
Ashley Richter

Dropping out of college! I was in school for three years for elementary education! Growing up I thought I wanted to be a teacher so bad because in small towns having a plan is very pushed as well as a conventional job! I transferred throughout three different colleges, even played collegiate soccer to try to make it work. One day I woke up with a gut feeling that it just wasn’t for me anymore. Read more>>
Dr. Crystal DeBerry, LCSW

Let’s talk about quitting a job to fly an airplane and build it at the same time when you are not a pilot or mechanic! LOL! That was me in 2014. I quit my job as a renal social worker and birthed Indomitable Families Affected by Incarceration (IFAM) a 501c3 nonprofit located in Memphis, TN. During this time I was “physically” a single mother with two small children and and infant as my husband was incarcerated. I started IFAM to create a mental safe space for women who had a loved on incarcerated, formerly incarcerated, or they themselves have had an interaction with the justice system. Read more>>
Mel Lockett

Trying to make art a full time career is a risk in itself. As a freelance artist or an independent contractor your income is solely driven by your ability to market yourself as well as deliver in a timely manner to keep the revenue flowing. When I started tattooing, women were not very present in the community. Black women were almost non-existent. I was mentored and worked under nothing but men and has to find my own way. There were certain aspects to the tattoo community that no one would be able to teach me because they had no experience with the changing technology and social media was becoming a huge necessity in staying relevant. Read more>>
Alle Justyn

How many of us are told that once we graduate college or finish high school we have to immediately go into the workforce? I know for me that’s exactly what I was told. I was told that after I finish school in exactly four years, I then needed to find a 9-5 corporate job with full benefits, and work my way up the ladder until retirement. If there is one thing that I know, it’s that I’ve never been an ‘inside the box’ thinker or someone who follows the norm. Read more>>
Abigail Melton

I would have never described myself as a person who took risks, at least not ones where I wasn’t fairly certain of the outcome which, ironically, makes it not very risky. In the beginning of 2021 I was entering my final semester of college and was facing the rapidly impending graduation date. I was looking at the potential career options after graduation and the uneasiness about graduating only rose. I was working full time, going to school full time, and panicking the rest of the time. For our final semester we had to complete a marketing project which we worked on the entire semester. Read more>>
Tamara Mlynowski

Early winter 2020 I took the risk in quitting my full-time salary position in accounting to help grow our business. Did my husband still have a full-time salary position? Yes. Did I have 5 month baby? Yes. Did I know what I was doing? Nope. Fast forward to November 2020 when we took another risk in launching our one of kind dessert truck. Did we know it was going to work? Heck no. Did everyone fall in love with the concept during a pandemic? YES! Now July 2021 we signed a lease to our very first storefront. Read more>>
Patty Dando

Often I remind myself that if you are not on the edge of fear, then you are not growing. The small business I started over 15 years, Zen Cowgirl, has been a constantly evolving entity and everyday is a conquering of challenges.
Started as a small creative side hobby of vintage resale, our little business has evolved into a full time enterprise that now includes my husband as co-owner and sidekick. Read more>>
Hannah Park

I think the biggest risk I’ve ever taken was quitting my full-time job to pursue something else, even though that meant taking a huge pay cut. At the time I wasn’t sure what I wanted but I knew it was anything but my current job. Unfortunately the pandemic hit shortly after I had quit, businesses and offices were closing down, and it was tough to find a new job. I kind of took this as a blessing in disguise because this gave me a lot of time to focus on things I really enjoyed which was photography. Read more>>
Amy Chenevert

Risk taking is certainly a topic in which I can relate to as a business owner. The introduction of the “Gleaux Girl Sequin Spirit Jacket” is certainly an impactful story in my entrepreneurial journey. Back in 2019 a big group of us had a dear friends birthday party in New Orleans. After a fun filled celebratory lunch at Galatoires, complete with a Second line and ALL THAT JAZZ, we journey into the French Quarter and all started buying fun accessories such a sunglasses, wigs, hats etc. In the far back corner, I found a jacket with tufts of sequins popping out, black, teal, purple and hot pink! Read more>>
Steve Torres

I was an independent contractor with a courier company. Earning a great income of 5 figures a month. I was basically working 24/7 would sleep in my car and shower at gym. I would commute from San Diego to Los Angeles everyday.
I never had time for my family or even photography. This one day the company I was working under, had wanted to stop my pay for commuting from San Diego to Los Angeles but still wanted me to commute everyday, that’s where I said I’m gonna take the risk and pursue in my photography. Read more>>
Marhia Johnson

The first risk I took that was life changing was making the decisions to have my oldest son at the age of 17. I knew that this will be an extremely scary experience. But I was able to persevere through the hard times and look at how much of a blessing this was. My oldest son was actually the motivation for me to start my hair business. I was in college but I was struggling to provide because I was a full time student. Read more>>
Shakela Etter

The biggest risk that I have taken was when I decided to continue my salon business off of the vision alone. Let me just say that life was really kicking my ass from every angle you could imagine. I carried it well, so most people didn’t even have a clue as to what all I was juggling. I felt like I had the weight of the world on my shoulders. Yet, the faith in my vision, that God gave me, kept me going. As I was deciding to resign my lease, I was also deciding to become a new person. Read more>>
Lenore Lyons

So, I was perfectly happy teaching second graders…until I wasn’t. I spent 15 years launching my own children through college and beyond, empowering other people’s children to be their best selves and finally it was time to launch myself. I wrestled with the decision. I knew I needed to live a more creative life. I thought about it constantly. Finally, my big idea… I will make books with people! Yes. That was it, as crazy as it sounded. I wasn’t sure what that would look like but it sure felt right at the time. Read more>>
Adrien Paczosa

A risk that I took that changed the course of my life and company was so simple and something we all do daily, answer an email. I answered a random email from someone asking to learn about the dietetic field and if I could take the time to answer their questions. I love talking about the joy and passion I have about being a registered dietitian, so taking time to talk and share that with someone I am all for. Read more>>
Jasmine Kelley

When I created 2:22 Fashion RX it was one of the biggest risk I ever took. I had been managing retail stores for over 12 years and always wanted something of my own, but was always afraid of the behind the scenes aspects of business such as operations, marketing, finances, etc. I knew from seeing what I had did for other big companies the power and ability I had for selling product as well as training and developing teams, but did not know how successful I would be pushing my own brand. I decided to take a risk in 2018 and I have not looked back since. Read more>>
Gene or (Geno) Budowski

Life is all about taking risks. Whether it is you risking something little or something big. I took the risk of being a Tattoo Artist around the age of 2o, I was so broke haha. Dropped out of college and fully committed to this craft. This industry has only been legal since the late 90’s, making it even more “risky”. When I first started out, a lot of people/ friends and even family, shamed me for wanting to get into this kind of business saying it was only for druggies and bad people. I quickly learned that some of the nicest people in the world are covered head to toe in tattoos, and I learned quickly to never judge a book by its cover. Read more>>
Shyam Kumar Nair

Film has always been my dream. A dream that I was never able to pursue due to my family pressure for doing 9-5 job and they thinking about (log Kya kahenge- “What people will say”). Taking risk was not my cup of tea, until the day I realized that my life is not going anywhere with this 9-5 job, and I am going to end up like every single one of those who just keeps on dreaming and move on with their regular work. Read more>>
Stephanie Garza

Early in my career, I worked for a few doggy daycare companies and trainers in different cities in and outside of San Antonio. When it came time to start Pup Pup & Away, I knew San Antonio was the place to do it and that I could offer something a little more outside of the usual doggy daycare box. But, would a training-based dog daycare be something San Antonio would be interested in, especially if the service cost more than other daycare facilities? Read more>>
Myrna Steinbaum

I had prayed many of years 1989-2010 that God would bless me with this business, and it wasn’t till I worked in this industry, taught in it, and managed in it. Then in 2010 I felt the call clear as day and took the risk starting our business in the back room of our home and never looked back, and here we are in 2022 with over 60 employees God continues to lead this ship and we will be here till he moves us. We have been truly Blessed:) Read more>>
Amber Cavanaugh

The best risk I’ve ever taken, in regards to music, was simply putting myself out there. I’ve got a hilarious story for you. It was back in college, and the only “performing” I’d ever done had been school talent shows (I’m talking middle school and high school, way back in the day). There was this adorable café downtown, and they had put up flyers for an open mic. At this point in time, I played a little ukulele, a little guitar, and I could get through a song or two if I really psyched myself up, but I’d yet to ever really sing in public, let alone on a stage. Read more>>
Martí Noguer

I’m Martí Noguer, a film and TV composer from Barcelona. Before moving to Los Angeles, I learned a bachelor’s degree in Music Composition from the Conservatori Superior del Liceu de Barcelona in 2019. During my studies, I obtained a full scholarship granted by the Ferrer-Salat Music Foundation. Also, I studied at the Royal Conservatory of Ghent with renowned film composer and conductor Dirk Brossé. Read more>>
Alisha Ward

I think that as a business owner… you take a risk every time you decide to invest in your business. Espcially when you’re doing it out of your own pocket! The biggest jump you will take will be an investment in yourself! The constant need to do better and wanting your business to grow is a moment where you will be the hardest on yourself. Trying to figure out whats next and assuming that your plan will work out is all apart of the game. Read more>>
Debra Roark

When I decided to scale up my business was very necessary. I was in a very nice comfortable space prior to my current location, during COVID I was thinking of doing an event to help other entrepreneurs in growing their businesses along with myself. The idea was to find an event space where we could set up and sell our products to the public, network and etc. So I was driving around and saw this sign that said they had temporary leases on a property, given the fact that a lot of businesses were closing – landlords aren’t making any money. Read more>>
Amanda Byrd

After working in the Pharmaceutical/Banking industry for years I noticed that folks were drawn to me. I would sit and listen to their stories, encourage and pray for them. One day while working in my home office I felt led to write a new vision and I did just that. This vision included Biblical Counseling and a farmhouse to work in. This meant that we would have to sell our home that we built, and I would have to resign from my job and go back to school. After much prayer and so much confirmation we sold our home and moved into a small farmhouse nearby. Read more>>
Lexx Strickland

Going into business for myself was an automatic risk. Luckily, I had my mother helping pay for daycare expenses temporarily but everything else was on me. Everyone kept telling me I needed to keep a part time job to secure some type of income, but I was hard headed and totally against that idea. I wanted to make myself 100% available to my clients. If they needed me there at 8am or 8pm I could be available and not working around someone else’s schedule. Read more>>
