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.

Amanda Stevens

As full time working therapists, wives and moms for many years the day to day physical and emotional demands lead us to a conversation about “what else is possible?” We are people oriented and knew that we had a skill set to build a community and what better way than a good cup of coffee and creating a memorable experience. Read more>>

Lisset Tresvant

Taking risks is my middle name. I was working a full-time job in a company I had been with for over 5 yrs. I had weekends off, a great schedule, excellent pay, and great perks like yearly bounces, vacation, time off/sick time, and all the bells and whistles. But, I was unhappy and unfulfilled in this line of work because I wanted to do something I was passionate about. I was a makeup artist outside my 9-5 doing, I would do bridal and event makeup on the weekends. Read more>>

Trevor Fulmer

In April 2019, I launched Trevor Fulmer Design. I had recently been published in The Boston Globe and client inquiries were rolling in, but in March 2020 life came to a standstill. Covid. My client’s and I were all suddenly stuck at home. This meant no client visits, no vendor appointments, no contractor work, nothing. I thought I picked the absolute worst timing to launch my own business. Read more>>

Erin Cafferty

The biggest risk I’ve ever taken was to go freelance. I was pursuing my Master’s degree in strategic communications when it came time to job hunt. After applying to over 100 corporate jobs because I felt like that was the obvious next step but never getting a single interview, I took a step back and asked myself what I wanted. I dug deep and realized I had talked about becoming a consultant for years, but didn’t go after it because I didn’t know what that looked like, how to start, or whether that would bring me success. Read more>>

Jessica Cowden

We all know what the year 2020 had in store for us. Unfortunately, 2020 was the year everything was shut down. In our case, 2020 was the year we took off. Talk about turning a negative into a positive. With everything shut down, I had a lot of time to think. To think about what I really wanted to do with my time, what my passion was, what I wanted to invest in. It became obvious after being in the event industry for over 5 years, Read more>>

Agnes Pierscieniak

I have heard “Jump and the bridge will appear” but I am the kind of person who slowly walks into the shallow end of the pool and would typically not dive into the deep end fearlessly. Yet, that is what I did with my Creative Business. It was the start of Covid, and I had just hear my Creative Director contract was not renewed for the following year. I had nothing to loose. No health insurance to quit. This was the time to see if I could make a living with teaching art workshops. I had to jump and hope there was a bridge. Read more>>

Jane Burton

In the twenty-five years after art school, I worked in the corporate world as a Graphic Designer, and later as a Marketing Director. My daughter, Caitlin, was eight, I had a full-time job and I volunteered at Caitlin’s school when I started working in clay again. I was passionate about it; somewhat obsessive. I built a small studio in the lower level of our home and would start throwing and hand-building pots and sculptures at 8pm every night. In the wee hours of the night, I’d force myself to bed, knowing there were lunches to pack, carpools to drive and work to get to on time. Read more>>

William Alexander

Do you have something in mind that you could do to leave the oh’ so repetitive life you currently have, but you or others around you may have thoughts that it’s too risky, unsafe or too big of a goal to achieve? What I have learned in life is that the bigger the risk, the bigger the reward. Of course theres is certainly a flip side to that coin & most risks I take are calculated & thought out. I spent a good portion of my adult years working jobs that I hated. I had bosses that would never really recognize my talent & I felt as if I was a just a number. I knew I had more to offer in this life for others and for myself. Read more>>

Abigail Wennerstrom

From an early age, many of my memories are entrepreneurial. Whether that was casting my siblings in home plays and charging my parents an admission fee, or decorating blank journals to sell at school, I was constantly looking to build something with my life. Read more>>

Tarnissha (Moe) Sass

By all accounts I am a statistic. I was a 16 and pregnant welfare mother who made a decision that although according to society I was a statistic, I was not going to be defined by that. I went to the US Army Reserves and left my then 3yr old son with my parents. I came home from the military and shortly after landed a position in a telecom company. I would stay in the company now going on 25yrs. Read more>>

Megan Gonyo

When I decided I wanted to start a business as an artist, I actually started small to limit risk. I think this is probably a common fear for most because not knowing where next month’s rent will come from can be pretty scary. I had a full-time job at a software startup company, and I had every intention of keeping that going until I could fully replace my salary with my business profit. Start where you are is the best advice I’ve gotten, and I share it with everyone thinking about starting their own business. Read more>>

Madison Liedtke

Madly is the biggest risk I have taken. I always had this incessant feeling that I needed to pursue something creative on my own. It would show up in different ways. First, it was starting a “business” selling bracelets in the back of my 3rd grade classroom. Then, it was “Skye Denim” where I upcycled thrifted denim, getting messy with bleach and paint. I was very entrepreneurial but felt directionless. Read more>>

Daniel Hagerty

About 14 years ago I had decided to go back to school full time and was personal training out of a local gym. My wife at the time and I were running a weekly bootcamp at our local church in the parking lot. Some friends approached us about opening a gym together since I had years of experience in the industry. We prayed about it and felt a calling to do so. Read more>>

Julie Kostic

In 2019 my husband and I decided that life in the DC metro area was starting to wear on us, and we set a five year plan to try to figure out a way to move further south to sunnier skies. Well manifestation can be a powerful thing because about a week later a job popped up for my husband that happened to be in Orlando. When he received an offer we decided to take the leap to leave the home we had known for years and start again in a brand new state. Read more>>

Donovan Bridgeforth

Starting The Official Black App was a big risk at the time. In 2016, racial tensions were at an all time high and the cancel culture was just beginning. Starting a platform for black owned businesses received much criticism in its first year, but it was that risk that paid off just two years later when Jay-Z and Diddy wanted to come out with a platform similar and in turn gave us all the buzz we needed to become successful and relevant. Read more>>

Devin Perkins

Recently I took the risk of moving to the Atlanta area after being in the DMV for 29 years. I moved to be closer to the network of people I work with now and it has been life changing experience for the betterment of my future. I’m closer to my mentors and opportunities that come with working in a closer proximity. Second to becoming a Christian, It was the best decision I’ve made in my life Read more>>

Kayla Harper

This year, I took the biggest risk yet with my business: I left corporate America and took on my business full-time. For the past eight years, Coasters & Co has been a side business that I spent my nights and weekends building. After dropping down to part-time at my day job in the fall of 2021, to experience more of the holiday season with my craft, I knew I would be making the leap in 2022. When April rolled around, I officially became my own boss and navigated a new life. Read more>>

Emily Dralus

Around the time that COVID happened I was furloughed from a job I had as a lifestyle specialist. During that time my mom, who is also a small business owner, hired me for some part-time virtual assistant (VA) work for her business. Then when I got back to my job I realized how unsatisfied I was cleaning chairs by the pool and working on the same neighborhood newsletter each week. Read more>>

Christina Bastian

Before I became a small business owner, I worked for an amazing business partner and colleague who owned a small mental health practice. It was never my goal to have my own business because it seemed too impossible for me to be able to manage the responsibly and bring in enough income to make it viable. Read more>>

Amanda Renkel

In the summer of 2021, talk began to stir about the possibility of my job going under. I had been an online ESL teacher for students in China since the winter of 2018. It was a fantastic job, and although demanding with its early morning hours it was an outlet of joy for me that also happened to pay the bills. When discussions about Chinese regulations on American teachers began, I started to panic. In the summer of 2021, talk began to stir about the possibility of my job going under. I had been an online ESL teacher for students in China since the winter of 2018. It was a fantastic job, and although demanding with its early morning hours it was an outlet of joy for me that also happened to pay the bills. When discussions about Chinese regulations on American teachers began, I started to panic. Read more>>

Emily Burke

I am a risk taker, and proudly so. In 2012, I made up my mind that a traditional lifestyle, shift work and spending all of my time in one place wasn’t for me. After a successful career as an Emergency Room nurse of 13 years, I began working in real estate marketing, but that simply wasn’t enough. In 2015, I became a licensed Realtor, and in 2018, I became a licensed real estate broker and grew a team of real estate agents. Read more>>

Ashley Clemens

For 4.5 years I taught in a charter school in Brooklyn, NY. During 2 of those years I was in grad school working toward my master’s degree, and the latter 3 years I spent coaching teachers as an instructional leader while teaching. Needless to say, life in the high pressure and pace of a high performing charter school with all the additional roles and responsibilities had me working 70+ hours each week for years on end and began taking a toll on my physical and mental health. Read more>>

Braxton Fuller

I graduated from College in May 2016. I couldn’t find a job for quite some time when I graduated. I worked with my best friend being his assistant, served part-time, worked construction, and worked a non-paid internship that summer. I put in probably 50 applications and never got a callback. One day, I got a callback for a job I wasn’t qualified for but I impressed the managers during my interview. I was dead broke and was just getting by. Read more>>

KAYKO

Earlier this year I transitioned from my band project “Your Best Friend’s Favorite Band” to a solo act “KAYKO”. It was one of the hardest things I’ve ever done because I put my blood sweat & tears into my band project, but I knew in my heart that it had to come to an end. I feel like as an artist it’s our duty to create what feels authentic, and I got to a point where I knew I needed to change my sound and my branding to better represent where I am in my life. After a difficult transition time, Read more>>

Angela Tyler

You always hear these wild stories of entrepreneurs taking crazy risks. I do think it’s true that a lot of entrepreneurs thrive off that. But, I’m not one of them. I’ve always considered myself pretty introverted and relatively risk-averse. I say this to illustrate that you don’t have to be a big risk-taker to be successful. That said, you do have to take some risks. Read more>>

Nicholas Agrinzone

The date was summer 2019. After being completely burnt out from the education system, my now 19 turning 20 year old self decided to get my associate’s rather than my planned bachelor’s degree, and kickstart my film career earlier than expected. For the majority of my life, I had always played it safe and that in turn got safe results. My family and friends were highly skeptical of me choosing to leave school early, believing that I would come to regret it in the future years to come. Read more>>

Mackenzie Stanley

In March of 2021, I made the decision to start my business – Socials With Kenz! I had always felt like entrepreneurship would take a spot in my life, but I never knew to what extent. Although I am so grateful for taking that step, there were a lot of mental hurdles to overcome. Read more>>

Murlande Mede-Ducksworth

One big risk I have taken is relocating to another state. Leaving my hometown to move with no family besides my husband and daughter. To build a business off of word of mouth and strangers. Read more>>

Charmion Thrasher

My name is Charmion, and I was born and raised in Cleveland, OH. Growing up I spent a lot of time participating in after school activities and attending church with my family. I come from a large family, so I learned early on the importance of speaking up and sticking together. As a kid, the church was the first place I learned about being a part of a community, and the positive impact that can be felt when people truly care about their neighborhood. Read more>>

Amy Schultz

It all comes back to the financial pain that I experienced. When my first son was born, I had $30,000 in credit card debt, $50,000 in student loan debt, and no savings other than my 401k, despite having made a very good salary for a long time. His birth was traumatic, to the point where I ended up on life support. I needed more time than I was given to heal but hadn’t planned for that, so I had to go back to work despite not being physically or emotionally ready. Read more>>

Kristen Clemons

Starting from a young age I loved the beauty industry. I fell in love with an industry that encouraged diversity and uniqueness. One that allowed people to be vibrant and bold if they wanted, or soft and natural. An industry that makes people feel confident and beautiful. Read more>>

Tamika Bickham

When I was in college at the University of Miami, I was pursuing internships in Broadcast Journalism. I wanted to be a TV reporter and I wanted to move to Los Angeles. So, I applied to an internship with CNN Los Angeles, a reputable media outlet where I felt I could also get experience in the entertainment industry. Over 1500 students applied for this internship. I was thrilled when I got a call from the HR Director, overseeing the internship program. It was an initial screening call, but we had a bad connection. The woman who’s name I thought was Gina, asked me a few questions, but we got disconnected after a few minutes. I never got a call back. Read more>>

Carla Rodrigues

I still remember the very day it hit me like a lightning bolt- you need to open your own practice. Once this thought made its way into my conscious mind, there was no turning back. The question then was- well how am I going to do this ? I was flooded with ideas for the practice, business plans, location, investment, demographics, general practice or specialty?! Read more>>

Manisha Tailor

Since the age of 8 years old, my twin brother and I together ate, drank and breathed football – which at times got us into quite some bother at school. I was an Indian girl who wanted to play football. An Indian girl who was perceived to be going against what everyone had always done and defying cultural norms; one who had to fight and would not be defeated. Read more>>

David Wolk

I was 18 years old when I started Cranky Yellow in 2005. I didn’t go to college and moved to the nearest city, Saint Louis, to open a store, which was my dream. I’ve always taken big risks, mostly because I’m driven to create and put stuff out there, which is risky. When you create things that are personal, as most artists do, you don’t know how others are going to respond and so it opens this conversation about risk. Read more>>

Tawana Rice

I’ve taken many risk during my real estate career and I’m learning that my biggest blessings come from stepping out of my comfort areas to explore newer levels the career brings. When first beginning to explore Real Estate, I held such a strong passion for the career I couldn’t wait to make the first move. It was time to make the dream a reality. Read more>>

Nomeka Tyson

I remember as a child dreaming of owning my own hair salon and beauty supply store. Although there were obstacles throughout life that could have changed that course, I was able to graduate from beauty school in 2009 to become a licensed cosmetologist. After working from my home for 3 years, I was able to obtain a 1,500 sqft space in the business district of the town I lived in. From December 2011 til May 2021 the business successfully serviced over 200 clients and their families throughout the community. Read more>>

Joedian Douglas

My partner and I decided to start our business together. When we started we knew that one day we would want to own a Brick and Mortar store. We didn’t know when but we know it was the goal. As we continue to make new items and explore our ideas we quickly realized that it needed to be sooner than later. Added in with the hardship of me finding a job that was ok with my schedule of taking care of our children, we decided to take the plunge and dove head first in. It is definitely the biggest risk that we have ever taken. We have only been open a little over a month so we are crossing our fingers and hoping for the best. Read more>>

Bini Sebastian

I feel like I take a risk anytime I bring my art into a space where most folks know me as a therapist or class instructor. I’m being vulnerable and showing parts of myself that are human through my art, and I fear that others will see me as less credible (so much to unpack here). A memory that comes to mind is performing spoken word at ZouSoul in May 2022. ZouSoul is an amazing Black-led student organization that supports University of Missouri (Mizzou) students who want to perform music, art, spoken word, and more. Read more>>

Ms. Béquille

You learn from taking RISK! Since most people tend to avoid risk, those who are brave enough to take risks already have a competitive advantage. They are the ones setting the pace and leading from the front with new ideas, fresh offers, and bold inventions. Risk takers are the most adept at pivoting when the going gets tough. Traveling to different cities/states with the show where people are unfamiliar with the brand is a huge risk we took but it also worked for us as well. RDBXclusive was able to connect with new talent to help grow the brand. Read more>>

Tre Main

Growing up in a rural farm town in Kansas may not have been in my control as a teen – though it was farthest from what I envisioned for myself. Read more>>

MercyK Khenie

Being laid off pushsd me to take a risk! From home health, door-door sales, to customer service, I tried to use my buisness degree. I even moved to another state and yet, nothing worked, so I came back to Nashville. After fighting to get a job in corporate America for 3 years, I got hired, for what I thought would be my career. Promotion after promotion occured for the next 2 to almost 3 years, and then the pandemic hit! I was laid off, after just getting promoted to a new role, less than 3 months prior! Read more>>

Yani Nikole

I’m actually in the process right now of taking the biggest risk I ever have, and it’s been an emotional rollercoaster. My partner and I are in the process of relocating to a new home in a new city and we’re starting our own gym! It’s definitely going to be a labor of love, possibly for the rest of our life. The home is from 1883 and it’s beautiful but requires a lot of work. Read more>>

Kevin Kist

When I was 19 I dropped out of the University of Cincinnati to pursue the journey of an entrepreneur. That same week I moved out of my parents house and into an apartment with my friend Clif. I had zero dollars and zero plan other than the self belief that I was capable of building this vision in my head which was to build the best strength and conditioning facility possible! Read more>>

Torey “VIVA” Evans

As an event curator, I’d typically incorporate local food at my live pop-up music events. Whether that is having food vendors, food trucks, or local pastry chefs. At times I’d run into schedule conflicts with vendors. Being a creative entrepreneur I thought I’d take a swing at providing food and beverages at my Nothin’ But Luv Music Series launch event at XO Lounge in March of 2022. Not only did I provide the eats, but I also challenged myself to create a brand to present to my audience. Read more>>