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.

Heidi Lowell

I have been working professionally as an artist in Austin, Texas for the last decade. This year, I curated my first show, and discovered the I love hosting events, collaborating with other artists, and patrons, and curating shows. When my studio mate moved out of my trailer a month before our city’s big annual studio tour, I knew I had the perfect opportunity to follow my dreams of curating shows. Read more>>

Marchell Townsend

I was just a young lady working a 9-5 ever day not happy with work and trying to make ends meet things I end up getting pregnant on top of that I was doing all I could to my the money work for me but it just was not adding up so I had to look at the situation and see where I was going to go with this, so it could not have been a better time. When the pandemic started I came out of my comfort zone, walked away from my job, Read more>>

Janais , Kathy Lopez, Zikas

The biggest and most important lesson we have learned having our own business is that risks are the only way to get to where you want to be. You need to be uncomfortable, You need to get out of your comfort zone. No way else to grow. One risk that we have taken was leasing our C+C studio. This was mid pandemic time. We were not sure if we would be making enough to pay for our rent since there was so many less weddings and bookings happening. Read more>>

Brette Peeples

Going out on my own 100% was the biggest risk I have taken in my business. There was comfort, security, and reliability with working for a fitness company full-time and doing personal training here and there on the side. I have always beat to my own drum and knew fulling owning my own business was the direction I needed to go, but the unknown was nerve-wracking from time to time. Read more>>

LaShawn Kenley

I come from a corporate background where I was nice and comfortable being in an Executive Recruiter position for nearly 5 years! I was the best at what I did (and this is no exaggeration for when in sales your numbers are blasted all over the company for everyone to know where you stand. There’s no hiding). I interviewed, prepped and hired amazing talent for Fortune 500 companies, non profits, wealth management, PR firms and more. I thought this was going to be my life but I had this one little itch that wouldn’t go away… creating culturally infused fashionable apparel! Read more>>

Blanka Molnar

I have taken a couple “BIGger” risk in my life. But “BIG” is relative. Right?! The first risk – and one of my best decisions – in my life was when I first quit my corporate real estate job in Budapest and with two suitcases I moved to the other side of the world – more precisely to California – to be an au-pair. My family and friends had a variety of opinions about my move, but most of them thought I was crazy to leave my “stable” and calm life behind to change poopy diapers with an economics degree under my belt. Read more>>

Brianna Washington

The biggest risk I have ever taken was simply launching my business. For years I prolonged and procrastinated out of fear of failure, imperfections and just simply overthinking. In a timespan of one to two years I went back and forth with myself on when to launch and if I should ever launch, surprising right? Impulsively, I woke up one day and announced the launch the day of with no promotion nor game plan. Read more>>

Mary Margaret Johnson

Deciding to become a full-time artist this year was one of the scariest things I have done. I was absolutely terrified, but I knew I had to try despite my fear. I am so glad I did because this year I have accomplished so much. I was on the cover of the San Antonio Current this summer, have been in multiple exhibitions including my very first solo exhibition that opened this month, have sold art all over the country, and worked with museums and institutions like Texas Public Radio teaching workshops and art programs. Read more>>

Jerry King

This whole business in a risk. It depends on a lot of things, but outside of your talent, it takes perseverance, focus and listening to the right information. You can’t have what they call the “fireplace mentality, where you come out of the cold, sit in front of the fireplace and ask, “fireplace give me some heat, then I will throw in some logs. It also takes timing and patience. Most new artists are looking for what we call “the 30-second microwave popcorn results” for their career. Read more>>

Tammy Foster Harban Pauline Botchway

As mental health therapists, our jobs require that we are “lowkey” in the sense that we are to maintain our privacy and professionalism at all times when we are at work and even in public–which, when you live in a small town, makes it that much difficult. We cannot even say ” hello” to clients outside their therapy sessions. So fast forward to the summer of 2020 when the two of us decided we wanted to put our faces and lives on the big screen–Youtube. Read more>>

Molly Pearce

I got a new part time job in a workshop making designer books and it was in this large studio building with lots of different creatives working there. I had been a painter doing art events in Atlanta for over ten years already but although it was my passion, I didn’t think it could be my career. Then I saw this studio space and thought what about a studio? Read more>>

Essie Castro

A huge risk I took was deciding to not work for anyone again & becoming a full time hair braider during a hectic time, the beginning of Covid. Even though my skills weren’t all the way there & I knew absolutely nothing about being a business owner, I still took a leap of faith because I’ve never believer in “waiting for the right moment”. Waiting only pushes back your success & possibly buries it all together. Taking this risk was the best decision I’ve ever done. Read more>>

Brittany Michelle

I finally got my “dream” job on March 28, 2018 as a customer service representative for Verizon Wireless. Verizon was the call centers of call centers. If you worked at a call center your goal was to get to Verizon because of the pay and the benefits. I was there for almost a year until things started to go downhill for me. I loved it there at first. Read more>>

Christine Williams

Growing up in North Carolina with a Belgian mother, I was fortunate enough to travel to Europe several times as a child. I discovered that the world is so much bigger than the parameters of our daily lives and our hometown. My hometown was very small and felt stifling. I was bored and wanted more. I wanted a warmer climate and like many, I was always fascinated with Florida. Read more>>

Kelsea Koenreich

The biggest risk I’ve ver taken was completely letting go of my identity and rebuilding my life. After my third arrest, I had finally hit rock bottom and knew that if I didn’t change – I wasn’t going to ever be happy, or live much longer. After getting out of jail I remember sitting on my bed in a puddle of tears because I knew I would have to change everything about my life, my friendships, my conversations, my habits, where I went, how I took care of myself…everything. Read more>>

Andee Rudloff

I literally climb walls and hang off tall buildings to create colorful murals rooted in community, so you could say I take a risk every single time I work. Yet, I feel the biggest risk was committing fully to my career as an artist and muralist. I always thought I needed to have curator of this space or educator of that space with my name so people would trust me and feel confident in hiring me. Read more>>

Rob Amato

The time I took a risk is when I started my brand was at the end of 2018 when I found out the company I was working for with a salary was going to be shutting down and I decided to gamble on myself and take a chance and start my own Streetwear brand, It was always a passion of mine and I had a talked about it several times over the years, this was a chance to do it, so I started designing again since it was the 1st time I had gotten back into it since I was in Architecture design school in 2006. Read more>>

Amber Amrhein

I had been doing spiritual work part time for ten years by the time Covid lockdown hit in 2020, Throughout the years I would dance around the idea of pursuing it full time, but was scared that I would ultimately fail. At the start of 2020, I was working as a Marketing Director for a dance studio. A few months into Covid lockdown, I began reconsidering everything in my life. Read more>>

Glenn Lamp

Born and raised in San Diego, California, the love for the sea and art has been a part of my life since as far back as I can remember. From a very early age, I began pencil drawings and my love to create began. After attending college on an art scholarship, I went on to work with a large publishing company in Charlotte, NC. Shortly after getting married, I took my first leap of faith in 2000 and started my own business, Glenn Lamp Studio, providing commission art to the area’s designers, business owners, and high-end custom home market. Read more>>

Adam Tenny

I have been in the construction world for the entirety of my adult life. I started my first business at 19 with one of my roommates and am still self-employed in the industry today. About 4 years ago I started going to a local gym at the request of a good friend who had been training there for a while. As time went on I began to really enjoy my time at the gym and developed a friendship with the owner. Read more>>

Carolyn Kelley

The first major risk I ever took in my business was quitting my full-time job while a single mom to work my own business from home. I didn’t have security, was 22 years old and had a 2 year old to provide for, along with a home and car payment. It was terrifying, and at first, I panicked, thinking that I couldn’t be successful enough to make the income necessary for our living. Read more>>

Alina Kravchenko

I have always wanted to start a company ever since I was a little girl and I was not going to let anything or anyone stop me from living my life to the fullest. I had my life perfectly planned and did things by the book, that was until I was faced with an unplanned pregnancy in the middle of the economy crashing in 2008. I was 23 and left on my own to raise my son. Read more>>

Stephanie Nardella

Let me paint you a picture of the biggest risk I have ever taken in my life and why I did it. I wanted to be a lawyer since I was in high school after taking a Practical Law course. It was my dream and something I hoped to make a reality one day. I spent 7 years of my life post high school working towards that goal— 4 years in undergrad and 3 years of law school.  Read more>>

Palmer Lee

I was working in a completely different field before Assisted Lymphatic Therapy. I was a full-time songwriter in Nashville, TN prior. Studying music in college, I had always planned on music being my exclusive career in life. It wasn’t until the summer of 2019 that I decided I wanted to shift things. Read more>>

June Orocio

It is safe to assume that taking risks is key to owning your own business but it is also something that carries over into life. There a few things that need to be at play for any action to be considered a risk. Factor number one is that there is a potential for loss. Factor number two there is a potential gain involved. Read more>>

Lolita E. Walker

Three small words changed my life forever, “no thank you.” After working at a thriving business leader for almost twenty years, my manager called me into his office and offered me a lucritive and exciting new opportunity to relocate to a new city and help start up the same department to which I was leading at my current location. Without thinking too much in the moment, I simply uttered those three words. Read more>>

Christine Lam

It’s always a risk when you decide to dedicate all your time and effort to your passion project. Is it going to work out? Is it worth all my time and money? It’s honestly scary, especially as a creative, but I knew I wanted to work in music since I started collaborating with other musicians in 2016. This is when Faerie was born. It was the first time I felt like people wanted to hear my stories through my music and that it could turn into something really special. Read more>>

Karen Benitez

So many big decisions in life can be taking a risk; not knowing the outcome can be scary, but you’ll never know until you go for it. The biggest risk I took was leaving my job at a nail salon to open up my own independent nail studio. When working for a nail salon, you’re set up with the space, equipment, products, and the clients, so taking the risk of losing that assistance can put a lot of doubt in your mind. Read more>>

Bernail Fluellen

One of the greatest risks I’ve taken in life was moving to a big city to pursue a job opportunity. The move was lateral and did not seem like much at the time, but it led to the greatest turning point in my life and career, where promotion after promotion took place. Never did I think I would live to experience one of the fastest growing cities in the south. This one faith move took me on a journey of discovering community, purpose and my passion as an entrepreneur and creative. Read more>>

This Summer

There are a lot of risks that go into pursuing music professionally, but by far the biggest we’ve ever taken was going on our first tour. In September 2022, we set out to Columbus, North Adams, Chicago and Muncie to play with bands we’d never met, for people we didn’t know at venues and DIY spaces across the Midwest. Honestly, we didn’t know if anyone would even come to a single show. Read more>>

Cameo Turner

As a yoga teacher in a certain special field I cater to the plant lovers. I wanted to host a Ganja Yoga Mothers Day (CannaMoms Event) at a Crystal shop in Oakland California. After Calling the owner for months with no response, I lost faith and did not think it would happen that year. About three weeks before Mothers day I got a 333 number I did not know calling me and almost did not answer but something told me to. Read more>>

Kendra & Kelvin Brown

We were in Maldives on a once and lifetime experience and find out about Covid and the possibility the border was closing. While there many people loved our images and shared how everything looked beautiful. When we returned in March we had so many travelers booked for travel in 2020 and 2021 that we were knee deep in making changes and updates. But we knew from how amazing this experience was that we wanted to go back and bring our community. We already had other group experiences like Bali, Greece and Italy that we had to rebook so there was a risk in 1) launching a trip during the pandemic but also 2) launching a luxury bucket-list experience like Maldives. Read more>>

Christine McFarlane

The biggest risk I have ever taken was launching Christine McFarlane Events and taking it full time! If you were to google “How to Start a Business”, or read any self- employment books, it will provide you with a list of tasks to complete to properly apply for a business license and file for an LLC in order to best prepare yourself for your small biz start up, but those are all the easy steps- the less risky aspects of being small business owner. Read more>>

Victoria Smith

I planned to launch my online store in March of 2020. Two days before I planned to go to City Hall to sign my DBA it was indefinitely closed, and I had no idea what was coming or what I should do to move forward. I left my last retail job in December the year before because on top of it being a terrible work environment my physical disability had continued worstening to the point where I spent almost all of my time outside of work in bed. Read more>>

Teiwan Williams

I started Yoni Steaming for myself in 2018, When I discovered on how it was very beneficial for me as a woman, so I began learning about different herbs that was great for Vaginal Health. My daughter pushed me to start business to share and help other women. I was very scared to do it, there were places that women would go to do yoni steaming, but not where I was from were places offered that service. So I started creating handmade blends and products for women that didn’t know about this practice. I started out small and my own money that I saved, went local herbal shops and brought herbs to make blends to steam with. Read more>>

Elena Sonnino

One of the perhaps small, but could be big in the future – risks I’ve taken has been to name one of my biggest dreams. The idea of opening a retreat center has been percolating in my heart and mind for a few years, and in 2022 – I gave that dream permission to be a seed that I’m nurturing. The thing about naming a dream is that it can feel scary, because once I name it – I have the choice. Will I nurture it? Allow it to take space? Or will I let it seem too big and scary and have it fizzle? Read more>>

Megan Martinez

Myself as a nail artist/ business owner was a huge risk. I have been a hidden gem since I was 19 years old when I first started beauty school and became pregnant with my first child. I didn’t finish beauty school until I was 25. I was in and out of school throughout that time due to lack of motivation, having 2 kids, battling with staying in a toxic relationship and being a single mother of 2, my son battling Kawasaki disease, losing 3 family members in a year,, working nights cleaning commercial buildings, living in the courts, not being financially stable and in general just not loving myself enough to make the change for my small family. Read more>>

Jasmeen Wilson

In January 2020, right before we had any idea of a pandemic coming our way in North America, I quit my stable job at the University of Texas, Austin, to focus full-time on building my business, House of Chiron. I was about four months away from graduating with my bachelor’s in psychology, working full time, and a single woman raising two young boys. Read more>>