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.

Krista Garrett

I have had to take many risks over the course of being a business owner which can lead to some of the most valuable wins and losses I have ever had. In 2014, my husband became sick and had to step away from the business and at the time I was a stay at home mom to twin girls that were just under 2 years old. I was scared and really didn’t want to give up my time at home with them but I was also very passionate about music and the business. Read more>>

Beth Kronenberg

On August 10, 2016, with $500 in my bank account, I signed a sub-letters renters agreement to a physical space for my business. As a health coach I had been operating out of my home, car and just about every coffee shop in town- meeting with clients and helping them improve their health through better eating choices. But I knew that the kitchen was an important piece to all of this. And I wanted to show my clients- in a hands on manner- that working their shift in the kitchen was one of the most meaningful ways to change their health (and their waistline) That year- Kitchen Shift was born. Since 2016- just 7 years later- I have my own brick and mortar shop. Read more>>

Danielle Deihl

One of the most significant risks I’ve taken is studying abroad for a semester in Spain. It’s also one of the best things I’ve ever done. I took Spanish classes all through school and had always imagined studying abroad. I applied, planned, purchased plane tickets, and was in the airport when the nerves hit. It was my first time flying alone internationally, and I was about to spend 4 months in a country where I knew no one and would be speaking a second language. Read more>>

Sally Griswold

I remember the conversation vividly. I was talking with my sister, Josie, on the phone after a difficult conversation with the company we were licensing our concepts and designs with. They wanted to start selling our products through a massive discount chain. We knew that this would obliterate the sales for the many independently owned boutiques we had spent months building trust with and we were backed up against a wall. Read more>>

Toni Witt

Starting a business is all about risk. First there’s a level of personal risk you take, I did this when I decided to drop out of university and move to another continent. Then there’s the business risk itself – starting a business, especially if it’s building a novel product or exploring a new market, is all about making hypotheses and visions about the world. But most of the idea you have when you start is just a list of assumptions. You have no idea if things will turn out the way you imagine them. Plus there are a million unforeseeable things that will get in your way. Read more>>

joshua burnside

I am a US Army combat veteran. Through my multiple deployments, I relied on my faith and trust in God to make it through. Like many of my brothers and sisters, I had no time to make sense of what I’d experienced while deployed. After my injuries in 2011 and stateside post-surgeries and rehabilitation, I began to process war trauma. It was during this time I became angry with God and “the demons” started to surround me. Read more>>

Lisa Sanders

In 2014 I thought I would never make another CD again. I felt like I was done. The music business had changed so much in the 20 years I had been making my way and now I was on my own. I had my own label I had put out six self-titled-released CDs, and continued to tour. I had hoped that I would catch a bigger brake. With each self-released CD costing thousands of dollars. and working hard to make back my investment I grew tired of trying and risking everything I had, to play and produce good music, I felt like I had nothing more musically to say. Read more>>

Justin Stoney

There are two risks in particular that I took which forever altered my life. The first one led to the second one, which led me to where I am today. Academically, I was on track to be a Chemical Engineer. But later I decided to pursue my love of acting, music, and singing. Eventually, I moved to NYC to do these things professionally. This was the first risk – I sought what I loved to do over what seemed practical. Read more>>

Gina Washington

Taking a Risk When I graduated college, my first real job was working in an abortion clinic. That, however, was not the biggest risk I took. Granted, working as a counselor was empowering, scary, and transformative. The activist in me knew that a woman’s right to choose was important enough to take that risk of getting up, walking through protestors, and helping people decide their best personal choice. When I helped people match their heads with their hearts, their world changed forever. Read more>>

Amber Campbell

In July of 2015, I took a leap of faith. It is important however, that I share the moments leading up to that leap. As a little girl, I always loved the art of teaching and learning. However, I personally struggled with learning in school, because I would get easily distracted with sounds, which would cause me to zone out and miss important information.  Because I couldn’t focus in school, I was the kid that would come home and “play school” with imaginary students, Read more>>

Michael Riggins

The most significant risk I’ve taken was using my savings to buy production equipment (my living room was like a production studio: literally!) but because of that I was able to create some of the best work that I’ve ever made because not only did that inspire me to work but it inspired me to not give up. although some projects weren’t released I do believe the most impactful and the ones that needed to be seen were. Read more>>

Valencia George

The biggest, life changing risk I ever took was, leaving the only home and place I knew to go to a total different Island where I knew no one to start my life over. In 1994 I left St. Thomas where I was born and raised to go to St. Croix with just a change of clothes and $10.00 bucks in to my name. I had a rough childhood and I taught it would be best to go somewhere where no one knows me. I met this wonderful woman when I arrived on St. Croix. Read more>>

Kiki Carr

Everybody wants to be a diamond but very few can take the pressure . I inherited a talent for taking risk. Strong Matriarch women in my family gave me the dna and witnessing thier trials and triumphs gave me the courage to take no look leaps of faith . Earning scholarships to assist in my college tuition .Making The cut to enter the Military and Soon after Extreme discipline in handling full time employment while in Beauty school to become an Esthetician. Read more>>

Amanda Lambert

The year was 2020. The world was absolutely unknown. Prior to shutdown I was still working my 4 days a week serving job. I honestly loved that job. Serving is what I had known for almost 20 years at this point. I loved the company I worked for, my hours, the easy money. I had been building Mandy Rae Photography on the side for 3 years at this point. In October when it was time to go back to work full time, I made the decision to not. I was like I think I can be successful and not work both jobs. Read more>>

Kirsten Nicole

In July 0f 2022 I was on a week long roadtrip through the midwest with a few of my friends. We ended our trip in the southeast, in Nashville. At the time, at home I was working in a salon full time in Philadelphia. My career life was “okay”, it felt stable and I thought that meant it was good, but I longed for something more. While still on the trip, I began looking at jobs in Nashville. Read more>>

Josh Short

In my position there can be a temptation to program work that has already been “proven” as successful. What’s hard is learning how to provide opportunities for artists and work that takes risk. Audiences are smart, and while it can be easy to convince ourselves that audiences just want familiar programming all the time the truth is that they come to the theater to experience something new that they’ve never experienced before. Read more>>

Marquis Stewart

The biggest risk I have taken was last year of 2022. I was already battling myself and went ahead to take the risk to cut the people of of my life that were no longer for me and it lead to me becoming homeless and having to stay with family. Although this risk lead to that it also lead to my biggest breakthrough ever for the stardom of my entertainment career. I was apart of and casted on “The Prank Panel” on ABC and streaming on Hulu premiering this Summer 2023, as well as casted on “I Can See your Voice” Season 3 winning some life changing money. Read more>>

Canon Tyler

Coming into the summer of 2022, I was met face to face with what was both an exciting and terrifying reality. By this point, I had been steadily building a show schedule – growing from a sporadic show here and there during the late summer of 2020 to a constant 1-3 shows a weekend into ’22. At the time, I had been doing this while working full-time at a non-music related job Mon-Fri. The turning point came when I began having to refuse weekday, out-of-state shows – the type necessary to continue building a following – because of my day job. Read more>>

Kassi Schuppe

In May and November of 2019, I took two of the biggest risks of my life. The first was quitting my job as a Center Manager at one of largest physical therapy clinics in the country. The riskiest part was that I did not have a back up plan. I had grown extremely unhappy in my position and it was starting to take a toll on my mental, physical, and emotional health. This was starting to leak over and impact my relationships with my partner and children. Read more>>

Thurro Alexander

Starting the Hiker Lyfe Podcast was a life changing risk for me. Not knowing if I would fail, succeed, or if people would even listen… So far I’m 8 episodes in and every episode seems to get better and better! Read more>>

Ashley Easton

When we talk about risks, I think everyone commonly thinks of negative implications. Why is it that we’ve become so focused on the potential of bad when there’s also potential for something great with risks, even when one fails!? Within my own life, one of the biggest risks I’ve ever taken was quitting my comfortable career to move out to the middle of nowhere and start brand new. Read more>>

Mariah Kaminsky Artist/Painter

In 1997, I had just graduated from Ball State University with my bachelor degree in Technical Theatre. I was accepted and began my graduate studies in the same at Carnegie Melon University. One month in, I made the very difficult decision to drop out. I was not loving my technical drawing courses but loved my figure drawing class (my only class in the art department). I chose to listen to that instinct. Having no idea what the long term plan was at the time, I knew I just wanted to start painting…whatever that meant. Read more>>

Lisa Caroline Toon

Risk is scary. The last thing you want to do is fail. I think everyone at one time or another takes a risk. It can be as simple as tasting something new, starting a new job, or as big as investing a heap of money and praying it will pay off. What I get out of risk is the thrill of making the attempt and the possibility of a good outcome. I am no gambler. and I think I lean more on the conservative side of risk. Call it naivete. or gutsy, I love a challenge. Read more>>

Chris Harvey

Several years into my career, I had made the transition from assistant editor to editor, working on un-scripted projects (reality shows, docu-series for Animal Planet and Discovery Channel and the like). I considered myself strictly an editor at that point… but work dried up and I couldn’t find anything. One of my friends, a post supervisor, offered to bring me onto her current project as an assistant editor — I was reluctant but needed the work, so I accepted. Read more>>

SL Redd

Maybe I’m crazy, but I find risk-tasking compelling and exciting. I believe you have to be open to taking risk if you want to run any kind of business….everything in the building process is taking a risk. Including the team you build, the product/services you offer, the partnerships you establish, etc. I’d have to say the biggest risk I have taken has been relocating from the East to West Coast. My label, #MIHUSTLEENT, has established it’s reputation amongst the Detroit underground scene. Read more>>

Sharnice Sherrod

You know those times when life takes a sudden shift or unexpected turn? That’s the story of how I became a full-time entrepreneur in 2021. I’d been working as an operations manager for about 6 months with no plans of leaving…ever! This role fit me so perfectly! I was constantly working in my zone of genius, strategizing and implementing ways to make multiple companies more productive & profitable, when it was suddenly over. Read more>>

Alexis Allen-Brown

I have been painting for 3 years now. It’s always been for fun and to have something to hang up in my apartment. A couple of my friends knew about my artwork, but never actually seen it. Until the beginning of 2022, one of my friends hooked me up as a vendor at a dance event. I was extremely grateful and nervous at the same time. I never thought about selling my artwork, let alone as a full-time job. A dilemma came along between the start time of the dance battle and my work shift, I kept going back and forth on should I go? Should I call off? Or should I just wait until it’s more convenient? Read more>>

Talulah Rodriguez-Anderson

The biggest risk I ever took was pursuing music in general. I’ve always had a passion for music but didn’t grow up in a musical environment and wasn’t classically trained, but deep down in my soul I knew it was the one thing that would make me feel truly fulfilled and motivated creatively. I grew up practicing visual arts as a child and went on to study communication design in college, but always had my heart in music. Read more>>

Audria Turnbull

When I first stated my business making clay jewelry, I look up tons of videos on how to and got the list of supplies I needed. And because I was just starting out, not knowing if anyone was even going to buy my jewelry,I only stated with the BASICS. Clay, a clay roller and basic metal cutters. If did not take long to realize that I needed much more. If I could go back I wish I would have spent more time researching the right clay to use, the importance of a pasta or clay roller machine, quality cutters and earring pieces. Read more>>

Kristina Wright

The biggest risk I took professionally was the decision to leave my day job and pursue photography full-time. For eight LONG years, I worked a retail job at a grocery store. At first, it was like every other job. You get ready, you clock in, do your job, and go home. In the first few months of this job, was when my partner gifted me my first DSLR. Read more>>

Melissa True

I have always been someone who pushes myself a littler harder than I should when it comes to work. When I moved from Maine to Texas there was this feeling of disconnect from my hometown. I begin exploring the world of Telehealth to be able to still provide services to my Maine community while also beginning work in Texas and establishing a life here. This was in 2016, where my private practice was formed as a part-time practice. Read more>>

Myesha B.

After completing my studies in Trichology, I started my practice as a Holistic Practitioner of Trichologist, I was still employed as a 9-5 employee. It was difficult working my full time job and just opening my own business. I did not have the time to fully work my business and came to a point where I had to make the decision to pursue my business full time. It’s was a big risk because my business was not making the revenue needed to cover my business expenses or my personal expenses. Read more>>

Jameka | Hart

“Go ahead honey, take a chance.” – A quote I took directly from Eddie Murphy’s “Coming To America”. And it’s been my motto ever since (ask about my dating life). I was 1st led to radio by encouragement of a fellow radio personality to put my voice on the air. She said, “u have a voice for radio”. Before that i never thought about it or even liked how I sounded for that much. Fast forward myself & others helped to pioneer what’s now known as podcasting before its time. Read more>>

Alicia Osmera

I’m taking a risk right now. No, not with this interview, with jumping into starting my own business. I’m coming from a twenty-nine-year career as a licensed and certified respiratory therapist is an alarming move to make. After writing and publishing my first book, Terror In the North Tower eight years ago, I knew what I wanted to be doing as a career. Read more>>

Dava Giustizia

Life, I believe, is always built on taking risks. It is what keeps us moving forward and growing. It never feels comfortable when you take a risk in life, but most of the times, the things we are most grateful of now, were once a risk that we took, consciously or not. Read more>>