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.

Rosalyn Jefferson

The biggest risk I’ve ever taken was walking away from my career that I thought I’d spend the rest of my life doing… and doing so without a plan! Talk about crazy! A mother of two with no without a plan, a little bit of savings and tons of postpartum depression. A wild suggestion from my sister landed me in an esthetics school and never in a million years did I think I would be in school again departing from my years in the hospitality industry. Read more>>

Brianna Rosemarie Aldridge

There has been many varying considerations that has made pursing my art a risk. A challenging one is the common doubts and disbeliefs that come with careers in art. You always hear the saying “starving artist.” It makes things harder when not as many people believe in you. It is definitely true that selling your art is not the easiest. It does not come with a yearly salary and it could feel similar to walking on a tightrope. Read more>>

Rob Canales

My career can be measured in moments of risk. I’ve been granted so many opportunities to stretch what I’m even capable of to find my next phase of success and it’s led to me just being open to the idea of failure. I hate it, but I’m not afraid of it. Read more>>

Jeanine Pedersen

The biggest risk I took was to leave the corporate world and create Dressedtothej9s LLC. There were a lot of unknown variables, but I was ready and willing to take that chance. Read more>>

Daja Barnes

Risk are supposed to be taken everyday. Calculated risk to be exact. Honestly, If I picked a story, I’d be typing all day. It is very important to understand, your goal isn’t going to fall in your lap, by playing it safe. Nothing big comes out of playing it safe! Taking a risk has its pros and cons, but having an intentional plan to bounce off every hump is what’s going to set you a part from any other business or better yet have you 10 steps ahead. Read more>>

Prince Joshua

After moving to Arizona from Idaho when I was 18 I had started school for fashion, entered the queer community, and started influencing online. Through the 5 years i lived in Arizona i got my BA in Fashion Marketing and Management, became a social media influencer on Instagram, Tiktok, and Twitter, and became a well known gogo boy for my community. Read more>>

Chris Falgout

Stepping away from a 12 year career with a great salary and amazing benefits to open a food truck. Olive Garden was a great place to work, but the company vision on the culinary side didn’t quite match up with the deep passion for food and the culinary arts that myself and my wife share, While on the surface leaving behind stability for uncertainty seemed almost foolish, it felt almost inevitable. Read more>>

Rashira Gomez

The biggest risk that I’ve taken is the bet on myself. Read more>>

Kelsey Tetzlaff

The first thing I would ask you is, which one? Read more>>

Mia Henry

Hello Readers! My name is Mia Henry, also known as “Coach Mia”, owner of “Molded By Mia” Molded By Mia is a fitness company, established in 2020. I am an entrepreneur, business owner, personal trainer, and group fitness instructor. My introduction is so important to this article because I had to take many risks to get where I am today. Today I want to share the top 3 risks that ordered my steps. Read more>>

Anastasia Elliot

My name is Anastasia Elliot. I am an operatically trained pop rock artist and I build audio visual worlds and create art that engages your senses and imagination. Before I dive into my story, I want to talk about taking risks because I believe that our uniqueness and creative spirits thrive or die in our ability to take risks. Whether you identify as a “creative” or not, this applies to you. Read more>>

Antoinette Garland

At the end of October 2014, I landed a job with a major airline working in HR Services. During this period of holding this position, I felt secure in my employment, I felt seen, and I felt appreciated. I knew this opportunity would be life-changing at this point in my life. Negativing this new world, at this same time, my father was diagnosed with stage 4 lung cancer: the highs and lows. Read more>>

Shane Loftin

I’ve been a risk taker many times in my life. From high school sports to joining the United States Marine Corps and fighting during the initial invasion of Iraq 2003 to leaving a multi-million dollar company with a 6 figure income and starting my own company with customer 1. Read more>>

Miranda Ebner

I am not unique to say that my biggest risk was leaving the warm security of a full-time corporate job to jump into the depths of the unknown with starting a small business. Read more>>

Merry Matti

As someone who began their business venture at sixteen years of age, it can be easily expected that many hurdles will be encountered along the way. It takes a powerful mind to strive to keep that fire ignited. As I have grown up, it has become evident that having a business comes in waves of success. Read more>>

Jennifer Thomason

There were multiple risks as part of the journey of opening up Moja Beauty. The first one, and maybe not the most obvious, is that LA and Denver’s beauty scene are not the same. We noticed that some people elected to do more of a dramatic lash or brow style, but in LA there seems to be a theme of “less is more”. Read more>>

Christine Bode

The most significant risk I’ve ever taken was becoming my own boss. Read more>>

Josh Guerra

I knew from the time I was 10 years old that I wanted to open my own Brazilian Jiu-Jitsu academy and be a full time Jiu-Jitsu athlete. I spent my teen years just training and learning as much as I could about how to be the best athlete and coach I could be. I worked a lot of odd jobs before opening my academy just to save money to be prepared for the day I felt I was ready to actually open a gym. Read more>>

Alberto Flores

When the pandemic initially took over the world and shut down live events, our band had just put out a 4-track EP. It immediately eliminated any chance to play live in Phoenix. During this time, we kept writing, composing, just learning our craft in general. Eventually, when vaccines were being rolled out, we had written a larger piece that we wanted to record with a large band. It was super risky at the time, we needed to find a person for everything. Read more>>

Susan Strenkoski

Going out on your own and starting a business is always a risk. The comfort of a full-time paycheck, benefits and knowing how you are going to pay your bills, keep a lot of people in their jobs. So, imagine having the idea of starting two new businesses at the same time. Read more>>

William Curry

No matter how you approach it, starting a small business is a risk. Financially you need to be prepared for anything that may happen and all the variables that come with business. But more than that, is the risk of finally doing what you want to do and believing in yourself enough to make that leap. Even if you are starting out small, you are putting yourself and ideas out into the public and that takes great courage in itself. Read more>>

Alicia Haygood

Every day you wake up, you make a choice on what that day is going to be like. You set goals/tasks for the day. You plan your day out as much as you can. And then something happens that completely throws you for a loop. Welcome to being a Small Business Owner. Where everyday brings a new set of challenges, risks and decision making responsibilities. Read more>>

Rebecca Schaffer

I spent my career working for humanitarian organizations because of my passion for helping people and my desire to change the world. That calling put me exactly where I needed to be for many years and, in addition to helping my community, it allowed me to experience growth in so many ways. I am very grateful for the experiences, mentors, travel opportunities, education, and much more, that I received throughout my career. Read more>>

Amy Sichmeller

In the earlier years of my professional career, working always felt like a dead end situation. Grinding Monday through Friday without much control what I could earn year to year. Back then (15 years ago) working from home and jobs with flexibility were not common and as we started our family, I quickly felt the weight of holding a career and managing a household. Financially we needed more income to make ends meet, so by the time my kids were 2 and 5, I had started my first “side hustle” of many. Read more>>

vonte write

in 2020, i wasn’t really working a stable job at all. like i’d work for a few weeks and quit because i never really liked working for other people, it’s just kinda convenient sometimes you know? so yeah i had a lil job then boom, covid hit so then i started getting unemployment and stuff so it was cool because i was getting paid & really just locking in with music 24/7 for like a whole year straight. Read more>>