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.

Marcus Miller

I personally have never been an Executive Director before they hired me. I had been a Director at a Boys & Girls Club under multiple layers of management, been a Director or Coordinator for our counties District Attorney’s office, coached high school basketball, laid concrete and served tables. The first risk was the Board taking a chance on my when I wasn’t even working at that moment. Read more>>

Omolara Oloye-Adelusi

Pursuing a passion for business can be a big risk, especially if you have a day job and are deciding to work less than full-time hours to create time for your craft. However, taking risks is often necessary to achieve success and fulfillment in life. Read more>>

Anna & Adam Heinauer

In 2020, we were living in Denver and working remote corporate jobs in the health care industry. With an interest in food and wellbeing, we began scheming on small business ideas in an effort to find passion in our careers and to feel connected to our community. Our goal was to establish a business that aligned with our interests and supported the health and wellbeing of those around us. Read more>>

Joana Sosa

I have taken a couple major risks in my life and they have all brought me to a point in my life where I can’t help but be thankful to God for letting me get to this moment. Growing up in Kentucky, I was surrounded by creative minds (I know that’s surprising) but I genuinely had some amazing and out of the box people around me. Seeing how my friends were pursuing their talents, I realized that I had something to offer, albeit something that wasn’t going to be so mainstream. Read more>>

Jordan Jones

I’m not a natural risk-taker, which can be hard as an entrepreneur. I love having a plan and knowing exactly what I need to do to accomplish it. But in the world of entrepreneurship, there’s often so many ideas and so many ways you can implement them successfully. What I’ve found is that taking small risks at each stage has helped me get better at taking bigger risks. Read more>>

Nina Tulio

I was a salon owner for 11 years and a hairstylist for 20 years It is my life and all I know. I had a dream to become an independent educator and really wanted to serve the commission salon owner and all stylists. But I owned a salon and leading my team and showing up for them way my number 1 priority. So after a few years of sitting on this idea and working around the clock. I decide to sell my business and start my own consulting business in Jan of 2017. It was scary, it was hard. I mean really hard. I had doors close in my face all the time. I had many sleepless nights. I had many moments of wanting to quit and just give up. Read more>>

Susan Gregory

Necessity breeds invention. Additionally, it warms appetite for risk. In the spring of 2019, we lost our group studio to market forces in the booming real estate market of our city. Working in ceramics requires relatively expensive equipment and space. Because of that, sharing in a studio with other clay artists is mutually beneficial and I have worked in several shared studios throughout my career between South Carolina, Colorado and California. Read more>>

E.B. Hunter

Being a writer is pure risk. You may not be dangling from cliffs or walking across rickety bridges (though we make our characters do) but we as writers risk our minds every time we open up the laptop. We risk putting our souls on the page and then having it mocked. We must risk starting, even if we don’t know where we are heading. I started an online writing alliance last June, and I have talked to a lot of authors since then. Read more>>

Ana Pedraza

In 2010 I found myself amid the dissolution of my marriage with my 3 young children. My situation was not an amicable one and as a trusting Latina wife, it ended with financial hardships that included no home, no vehicle, and negative credit. The positive side was I had my children with me and a stable job, lots of courage, and a drive to improve our lives. Read more>>

Courtney Roten

I worked at a big USA Bank for over 4 years. It was comfortable and paid well. When my little brother died suddenly at the age of 24, I took an extended leave from my bank job. While I was grieving, I found comfort in my bearded dragons. They have so much personality and are often described as scaley puppies. I decided that life was too short to spend it doing anything other than what you love. I aspired to work with animals my entire life. Read more>>

Marie Darling

I just recently left the K-12 classroom. It was March 31, 2023 to be exact. I decided after 12 years, two of them during a pandemic, that it was time to stop teaching middle school art. I was burnt out, exhausted and was becoming someone I didn’t like. Throughout my whole teaching career, I have always created art and even before becoming art teacher, I was an artist. I always wanted to be an artist but also a teacher so a better term would be “artist teacher”. Read more>>

Jessica Meunier

Starting my financial coaching business during the pandemic was simultaneously the easiest and hardest decision in my career. While I’ve always known I wanted to create something meaningful and close the gap in the personal finance industry, I’m also a structured, Type A person with a family, mortgage and responsibilities – so this was a scary leap in a lot of ways. Read more>>

Nell Tice

On March 3rd, 2021, I walked into work and put in my resignation from my COO position at a successful coffee and tea manufacturer. I had no intent of doing so that day, no plan, and now, no recourse. Don’t get me wrong, I was unhappy in my career and had planned on doing this one day, but with a little more preparation. Read more>>

Clayton Williams

If you had asked me a year ago whether or not I was going to get a tattoo, I would have given the classic response, “I want one, but what if I end up regretting it in 20 years?” If you had asked me whether or not I was ever going to work full time as a creative I would have given a similar answer. What if I end up regretting it? Read more>>

Tashara Childs

The name of my private practice is Brave Counseling and Consulting. Before becoming a private practice owner, I worked as a manager at a bank. I had a very secure job financially, but I was not happy emotionally, mentally or spiritually. I knew that I wanted to be a counselor, but I did not know how I was going to work a full time job and also intern to finish the Master’s program that I was in. Read more>>

Leigh Kubin

I found myself in a space of playing it safe. That was the way I lived. Everything I did was well thought out and intentional. If it wasn’t safe, I wanted no part of it. The problem was, I wasn’t growing, I wasn’t inspired and I was bored. I would analyze all the things that could go wrong with a particular idea and talk myself out of anything “risky”, including my dreams! Read more>>

Amber DeBoy

I took a large risk during the 2020 Covid pandemic. My wife and I moved to San Diego from the Midwest one week after I graduated with my Master’s in Social Work. Shortly after arriving, I was finding it difficult to get an interview for any jobs relating to my field. I was beginning to feel bored, stir crazy and purposeless. I started thinking about providing cleaning services as a way to bring in some income. Read more>>

Xiangni Song

Pursuing a career in the arts comes with its own set of challenges and uncertainties. If you’re seeking a comfortable and easy life, it may be best to consider a different path. The truth is, the life of an artist is not always easy, and success is not guaranteed. Despite the efforts and hard work of many talented artists, they may still go unnoticed by the world. Read more>>

Stephanie Thomas

We’re trading the daily grind of corporate America for the pursuit of a new dream – one rooted in southern hospitality and sharing a good many things around the fire with new friends. It all started in 2017 when the frustrations we encountered in our own travels inspired us to create a design-forward bed & breakfast that caters entirely to dog owners. Read more>>

Christopher Mandujan

I started out producing only Hip-Hop & R&B records earlier in my career, however over the last 2-3 years I have branched out into producing more projects that fit in the Dance & Jazz genres. I believe it was a risk considering that my fan base or anyone familiar with my music in general was not accustomed to hearing that type of music from me. I wasn’t not sure if me attempting to displaying my range as a producer would work in my benefit. Read more>>

Courtney Dorsey

I’ve always been a bit of a risk taker when it comes to decision making, not necessarily when it comes to riding a rollercoaster or zip lining, but I’ve always wanted my life to be a curiously amazing story. Although, I am a small town, country girl at heart, I was tired of living a small town life. As a Louisiana native, though full of culture, my curiosity and higher purpose required me to evolve into a more well-rounded person. Read more>>

Meridith Grundei

In 2017, my husband and I decided that we wanted something different. We were living in a town called Lafayette in Colorado, just outside of Boulder. Where we had lived and raised a family for the past 10 years. We adopted our baby girl in 2011 and my stepdaughter had recently graduated from high school and was going off to college. Read more>>

Nia Alexander Campbell

A risk that I have taken that I am most grateful for was my decision to study abroad in Doha, Qatar in 2018. I was in my third year of university studying Painting & Printmaking and Art History at Virginia Commonwealth University (VCU). My university has a sister university in Qatar (VCUQ) exclusively for their arts program, so as an arts major I was eligible for the exchange. Read more>>

Anne Ylvisaker

Having a career in the arts is an extreme sport. It means continually leaping into the unknown with no promise of a safe landing. But without the leap, nothing new would be born. The act of creating is its own risk. I wrestle with this all the time. Hours, weeks, months, years, can be spent on a project that few people even know about or believe in and there is no guarantee that at the end of that time it will find a place in the world. So have I wasted my time? Read more>>

Sherelle Speed

The biggest risk I’ve taken was quitting my 9-5 and becoming a full time artist, I’ve always manifested a lifestyle that allowed me to be free with my schedule and not have to work for anyone and have the availability to work as i pleased. Which ironically i work more now then i did with a job. But the risk was necessary in order to be pushed to the next levels. Read more>>

Ronald Fields

Last year I was dealing with a few personal difficulties that had surfaced in my life. I wasn’t satisfied with my job, the lack of opportunity in my city or a relationship that I had maintained since college. As I began to think about my passion and the things that made me happy, my thoughts always led me back to my love for fashion, music, art, and modeling. Read more>>

Lisa Charles

Taking a risk involves stepping into a position of uncertainty where there is no guarantee of success. It can be daunting. It can be humbling. And if you’re not careful, the risk decision can stand between you and your dreams. This fear factor, which arises from the inability to know the outcome, presents the most significant potential stumbling block. I have faced that stumbling block in my career but have allowed fear to be a great motivator. Read more>>

Angela Williams

As a survivor of child sexual abuse turned advocate, I have decided to take a huge risk to be both a vulnerable, and transparent about my own abuse and courageous in speaking out on such a taboo subject. My goal is to provide child sexual abuse prevention and healing resources so that we can both help save the next generation of children from this horrific crime and help the millions of survivors of child sexual abuse find hope and healing from the trauma. Read more>>

Mutmainah Adeyemi

One of the risks I have taken recently is related to my love for traveling. I have experienced missing out on so many great places and deals because of friends who always cancelled or just were unavailable. This was around the time I got my first ‘big girl job’ living rent free with my parents so I was eager to use this opportunity to explore the world. I got tired of waiting on people or dealing with people who constantly cancelled on me and decided to take the risk of going to a country solo, by myself. My first trip was in the U.S, Tampa Florida to be specific. Read more>>

Derrick Green

Years ago after returning from the oncology lab my wife began to cry. She was absolutely distraught so I sent our then 5-year-old daughter next door to play with the neighbor’s kids so I could try and provide some comfort to my wife. By now she was wailing in a gutteral way that you can hear at funerals of a soulmate. Read more>>

Poiab Vue

As a child to Hmong refugees who came to the United States after the Vietnam War, like most children of immigrants, I was stuck in two cultures. I wanted to embrace the American culture that told me that I could be American even though I didn’t look like the rest of my classmates growing up in a small city in Wisconsin. When I would go home after school and prepare for the weekends, I would let go of my American identity and try to embrace my Hmong heritage. Read more>>

Jeanette Razo-Gonzalez

As a Play Therapist who works with children and families, I saw a need to extend some of the activities that we were doing in the therapy playroom to the home. I wanted families to be able to continue the work in their own home after graduating from therapy. I also wanted to reach families who have limited resources or fear the stigma of therapy. Read more>>

Adreyauna Lewers

During year 4 of my business, Ink to Prosperity, which is this year I have taken a “risk” to niche down even more than what I offered in the past 3 years. For 3 years, I focused on bring spiritual and personal guidance to any and everyone. I was new to business so it seemed smart to open my doors to all. But after some troubling experiences with a few white clients and clients that just wanted me listen to their problems without action, I was finally ready to niche into what the biz gurus call “your ideal client”. Read more>>

Christine Garcia

Apprenticeships are a huge risk to aspiring tattoo artists because you can never know when you’re going to actually start making money from your craft. Some apprenticeships can last months and others can last years. While everyone’s apprenticeship looks different, it’s a universal struggle to determine when you’re ready to start tattooing people. Read more>>

Letizia Silvestri

Sometimes life puts you in a fork on the road and you have to decide which path is best for you. On one side, there is the well-known path – the one you have been on for a while, the path most of your peers take, and that your friends and family support. And then, on the other side, there is the less-travelled road, the unknown that makes your heart pulse faster. Read more>>

Rare Xano

A risk that changed everything for me was when I quit my job to shoot videos full time. I was working at Champ’s Sports selling sneakers for about a year when I finally decided to quit. I felt like I was wasting my time there (even though I was making money) because I was making more money shooting videos, but couldn’t devote more time to working on them due to work and college. Read more>>

Catherine Baran

I’ve always been somewhat of a risk taker, but when it comes to my career, and the high-level of competition and pressure that it entails, most of the time my approach to listing appointments was to impress the seller as best I could from a professional standpoint. Read more>>

Chantelle Marie

” You are going to sell slushies”? ” A slushie bus”? These are the comments I heard when I first told a few people about my idea! Each time I would respond with” Yep, and it’s going to be so cool”! No one really believed in my vision when I first started out. When I attended college at North Carolina A&T I was a sports reporter and media host, killing the journalism game! Read more>>

Destry Carter

Being an artist in itself is one of the greatest risks a person could ever take. From showing talent to an unlimited amount of critics, the money needed to invest in yourself because you believe in yourself, to the experiences with all different kinds of personalities. The lost goes on. All for that huge question that we are start out with……WHAT IF IT DOESNT WORK OUT?! Read more>>

Jennie & Aaron Berger

The biggest risk we’ve ever taken was starting High Vibe Collective. It began in 2017 as a passion for building and creating pieces for ourselves and friends. That carried through until 2019 when we decided to commit to the idea of this turning into a business. Through those years we sacrificed our free time and weekends to building custom pieces for clients. Read more>>

Meg Holmes

Biggest risk: moving and starting an architecture firm in a city where I had never worked as a professional and doing so without a backup plan. Having worked for firms in Shanghai, Chicago, Portland OR, and San Francisco, for 10+ years, I decided to quit my job, move back to my hometown of St. Louis, and open an architecture studio. Read more>>

Alice Su

The best things in life come from taking risks. One of the biggest risks I’ve ever taken in my life was one of the best decisions I have ever made. The decision to become an independent hair artist. Graduating with my degree in business then going right in to hair school to being an entrepreneur /studio owner and now opening my very own salon. Read more>>

Laura Rosenthal

I graduated from law school in Colorado in 1993, took the bar exam and failed it. Took it again, failed it. I decided to take a break from studying for the exam, my ego needed to stretch and besides, I was getting married. Then I moved with my Ex-husband to California. Eventually, nineteen years out of law school and two sons later, a couple of friends told me they believed that I should “woman up” and take the California Bar Exam. Read more>>

Tamora Henderson

When I first started, it was easy for me to help birth the dreams of other’s apparitions. For many years, I sang the background for other people’s dreams and visions. I did it because I was blind, afraid, and unaware of my own importance and talents. Despite being told often how talented I was, I still struggled. Read more>>