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.

Mallory Musante

The biggest risk I’ve ever taken is when I decided to walk away from a previous business I started with a co-worker/friend because I was no longer happy or fulfilled. This business was by all account incredibly successful. We built it into a multiple 6-figure business over 5 years and it was my main source of income. It not only allowed me to pay all my bills but I was also able to purchase my first home as a single, self-employed woman. Read more>>

Kayy Mas

I recently took a very big, life-changing risk with my work and business. Travels with Kayy was started in 2018 as my side-hustle. For financial reasons, I always needed to work a full-time 9-5 job. However, I found myself becoming increasingly frustrated and overwhelmed with the toxic culture that comes along with a typical 40-hour work week. Read more>>

Robert Daniels

Taking a Risk- In 2006, I decided to retire as a teacher in New York City. I had moved to Florida in 2000 and the wear and tear of travelling back and forth was taking a toll on my mental health. I received a letter from my principal that my retirement papers had been denied but upon arriving back in New York, the job had been given to another teacher. This situation left me without any dependable income. I was asked, ” What are you going to do now ” ? I retorted, ” God Provides “…I took $ 600 and started Nappy Head Art. Read more>>

Sandra Lobaina

The moment I decided to go to Midwifery School was scary,overwhelming and exciting all at once. I was a young mom that had dreams of going back to school but once my son was born I knew I had to ensure he would be healthy and well taken cared of. I was determined to breastfeed him and I did everything I could to make that happen. I had to go back to work at 6 weeks postpartum and needed to pump and create a schedule that would allow me to continue producing enough milk for my baby. Read more>>

Adrienne Moch

Never in my wildest dreams did I ever think I’d be an entrepreneur. No way. I’ve always been single, so totally responsible for supporting myself, and I was very comfortable earning a nice living as a salaried employee. What changed? Why did I decide to take the biggest risk of my life and leave my high-paying job with benefits to go freelance? The foundation was laid when I started doing some freelance work “on the side.” One of my clients said to me one day, “You really should go out on your own. Read more>>

ISABELLE ALESSANDRA

The risk I took when I shifted my career from CEO of my own consulting company to full-time artist was a direct result of these words of wisdom from my 96-year-old mother during her final hours in hospice: “I’ve thought a lot about what I would say to you when this day came, what I might say so you’d really hear me, how I could turn these last moments together into a gift. I have one important regret to share with you, and it’s not about what I did with my life, it’s about what I didn’t do. Read more>>

Melissa Furness

My creative life has been a series of calculated risks, big an small or in the middle. The bigger risks are the more personal ones, I would say. One that sticks out in my mind as life changing is when I decided to participate in an artist’s residency in Hungary–the first that I did abroad. I knew literally nothing about the place when I embarked on the experience, which I decided would be best to embrace. I was in graduate school at the time, heading into my final year of my MFA, hyper-poor and had no idea what the future had in store for me. Read more>>

Bertha Osorio-Campbell

The biggest risk I took was purchasing a 200K laser machine in the middle of a pandemic before I even had an office to place it in. Yup, you read that right I had a laser device delivered to my house at the end of 2020 and it was that decision that lighted the fire under my ass to find a commercial property. Read more>>

Brianna Thompson

Moving to Austin to pursue my passion in fitness has been the biggest risk I have taken. I decided to take the rest to focus on bettering my life as a whole. I moved from California to Houston in 2019 and many events began to transpire shortly after. COVID-19 happened in March 20 20, I was domestically assaulted in April 20 20, and was alone in a state 1600 miles away from anyone I knew. In July 2021 I finally said enough is enough and began my plan to fully commit to personal training and a healthier lifestyle in all aspects of my life. I wanted to help others regain their power. Read more>>

paige Pauley

In 2016 after being at the newspaper in the advertising department for most of 20 years and being in the advertising industry for 40 years I had a revelation that i had had enough and wasn’t going to do that anymore. I had no plan. I had no money to speak of but I knew I wasn’t going to do that anymore. I had been creating art all of my life and made a living as a illustrator in my youth before computers came about, potter, painter, stained glass artist, in general design work for agencies and corporations. Read more>>

Freed

Once upon a time in Miami, I once ran down six flights of stairs, ran a mile through several crowded, and busy streets, did wind sprints through the ocean, and then ran back and forth sprints on the beach-all while tied and tethered to 6 people! I took a big risk going out to Miami. At the time, I’d somehow ended up as finalist on one of Grant Cardones internet TV shows. Read more>>

Tenia Pero

Listen. I would definitely have to say the biggest risk I have taken is quitting a 9-5 job and working mainly for myself. It’s a bit hard and challenging at times but there’s a reward at the end. Now, to be completely real I’m not at the end. The end for me would be to have a business that runs itself ( me not being there everyday.) One day I just looked around at the environment I was in. Not to knock anybody at all because I have been in almost every job you can think of. I said to myself “Is this what you really want to be doing the rest of your life?” Read more>>

Seton Edgerton

The biggest risk I’ve taken is putting my life on hold for a couple months and committing to a promise I made to one of my best friends while he was in the hospital. He was recovering from his second open heart surgery in one year and had just received a heart transplant at UCSD. He is an avid cyclist and set out to bike across the country for the second time to raise awareness for organ donation. This time the journey would begin at the hospital he received the heart transplant in San Diego to Jacksonville, Florida where the donor was laid to rest at Jacksonville National Cemetery. Read more>>

Keera Belviy

I always had the dream of a completely self-employed persona. Going straight from a vocational High School with a Cosmetology degree, I was shaped into a master hair stylist for 10+ years. Knowing I was making customers happy, and making a living wage at a young age of 18, I didn’t get to focus on what made ME happy, or really even think of it, until it started to affect my mental health. I knew it wasn’t normal to feel anxious driving to work every day and crying on your way home. Read more>>

Cachia Lewis

One of the biggest risks that I have taken was moving to Arizona by myself while married. I was at a point in my life where I needed change and wanted to grow mentally, physically, and spiritually. I could not do that where I was residing at the time. My husband and I took an impromptu vacation trip to Arizona and fell in love with the people, mountains, and heat. I knew that this is where I wanted to be so what did I do. Read more>>

Gina Michelle

Taking a risk, or rather, stepping into my responsibility as a practitioner and leader in the wellness industry. The average career length for massage therapists is 5 years. I have been practicing for 22 years now and owner of a private practice for that long as well! Along the way I have taken measured and calculated risks and they have everything to do with being clear of my purpose and knowing what I have to offer. My purpose and what I have to offer has been a sort of navigation tool. Just like a captain at sea keeping their eyes on the constellations for staying on track, no matter what risks or choices I make, it involves some amount of reflecting on whether those choices are aligned. Read more>>

Suzane Joseph

In 2018 my life took a turn, I walked out of an abusive relationship of 12 years. And before I knew it I was starting my life over again. I was stuck in my bed severely depressed not sure what my life had for me. Imagine crying every single day for months. Coming home from a long day and having to deal with your kids who are not happy, no more money left, I am unhappy and life just looked to be a hot mess. I really started to feel disgusted with me and started to contemplate ending my life. Read more>>

Carlito Black

I’ve taken so many risks in my life to survive. Selling Drugs, Robbing, Traveling across the cross to play football as a walk-on with no guarantees of a scholarship or even making the team, and more. Coming from nothing and having nothing has been my greatest gift in life. When it comes to risk I only see what I can gain cause I have nothing to lose. Moving to Atlanta to start my rap career without a car, without a job, without a place to sleep or a dime to my name was the best risk for my career. Read more>>

Candice Bottomley

I’m a single momma! I got divorced 4 years ago and had to start over. Literally. With nothing. I was terrified. Luckily I had background in real estate and I was a notary. Because of my good reputation in the industry and my connections I was able to land a job as a title rep for a company that i liked and respected. But sales in title is hard and it takes a long time to build a book of business. I was hustling and still am but I knew i needed to do more and that I didn’t want to work a 9-5 and sacrafice my life to someone else and their dream…. Read more>>

Bridget Farhat

I was working my first ever 9-5 job and I hated it. I knew going in I wouldn’t like it, but it had been a while since I worked with people and I missed that since of community since I was in a new city. 4 months in and I got to the point where I was crying in the bathroom almost everyday because I was absolutely miserable. The work I was doing was so unfulfilling. I felt like I was a robot & it was sucking my soul away. I knew I had to make a change. Read more>>

Dawn Tucker

The biggest risk I’ve ever taken was starting my own theatre company. My dream was always to live in my hometown of Flagstaff, Arizona and to create theatre. After graduate school, I worked for several years in Phoenix, Arizona and was involved in some wonderful theatre in the valley. When I got the opportunity to move back up the mountain to Flagstaff, I knew I had to take it even though it meant moving to a place where there was no professional theatre. Read more>>

Amorette LaFranchi

As far as I can remember, I was exposed to holistic medicine through my mother and father who were both from Mexico. Every Christmas break and summer my parents would take us to Mexico to stay with our grandparents for a week or two, and during that time, if any of us would come down with a cold or a fever, my mother and grandmother would gather some dried herbs from my grandma’s garden and boil it with water and we would then drink the tea. Read more>>

Monica Schwingel

Two years ago, I had my second child at 36 years old. I was an elementary school teacher and took the year off to stay home with my baby. I started working with an NTP (nutritional therapy practitioner) during this time and fell in love with the idea of healing my body through whole foods. I decided to quit my career as a teacher, go back to school to become an NTP and start my own business. There were many times I was afraid I would fail or that people wouldn’t think I had enough credentials. Read more>>

Amy Vander Linden

One of the biggest risks I’ve taken in my life is my husband I deciding to purchase a building for me to expand my physical therapy practice, add a yoga studio and collaborate with other providers to serve women in our community. We bought the building in December of 2018 and spent 2019 learning way more than I ever wanted to about permits, corrupt contractors and commercial building than I ever wanted to. We initially thought we’d be open in the spring or early summer of 2019 and had no clue what was in store. Read more>>

Jaiye Empress

Deciding to pursue my passions full-time as a creative entrepreneur was (and is) a major risk I took this year (2022). The world as it currently exists does not wholeheartedly embrace nor support nonconformists. Which, I guess makes sense because most folks enjoy the seeming certainty that consistent order and structure provide. Read more>>

Hannah White

If it doesn’t challenge you, it doesn’t change you, right? Before I moved to Castle Rock, I had been working as a physical therapy assistant in my hometown in Northern Nevada. It had been a lifelong dream of mine and truly, it remains some of the most rewarding work I’ve ever done. From industrial rehabilitation, to geriatric care, to standard outpatient therapy, I loved helping others overcome pain and regain their strength. Read more>>

Dineta Williams-Trigg

So I started in front of the camera many moons ago. I got tired of being typecast as the black best friend ,the hooker with the heart of gold or the drug addict. I understood that if I wanted this situation to change, I had to change it. I bought a camera and started telling stories about relationships that I wanted to see, with people who look like me. I didn’t go to film school, I just read everything that i could get my hands on about movie making and watched a lot of movies. then started submitting my short films to festivals and alas it was rejected time and time again. Read more>>

Jon White

Though Ink Monstr has been in business over 17 years in Denver, my tenure as owner and CEO is still a rather new development for myself and the company. My entire life I’ve known I wanted to be a business owner. I assumed everyone wanted that for the longest time. I assumed they saw it as the same pedestal as myself, though as time passed and I grew older it seemed to be a smaller and smaller lot that wanted to take on the challenges and burdens of ownership which only stoked my fire more. Read more>>

Evelynn Jones

$60, riding with a stranger, new city with not friends and family. I’ve always been a mover and a shaker – literally. I’ve moved to and lived in multiple cities. The first was Sacramento for college, where I did everything on my own senior year; from packing to paying for tuition and dorm room. Read more>>

Dana Buckmir

Becoming an independent author was a huge risk. I contacted traditional publishers for a while, but after multiple rejections I decided to do it on my own. It was the best decision I could have made. I tell anyone that wants to become an author not to wait for someone to validate their craft. You just have to believe in yourself. Read more>>

Luz Angel

The biggest risk I’ve taken in my life is leaving the highest-paying secure job I’ve ever had at the beginning of a pandemic to follow my passion for Creating. I grew up in an environment where art was just a hobby, nothing to make a living off of. I was always encouraged to find a “good job” with great benefits that I could move up in so that I could buy a house and be financially stable. I tried, for so many years, but I never lasted more than 3 years at any job. Read more>>

Chelsea Beamer

Last year, my boyfriend and I did something that most people think is crazy… I had only just picked up my camera in November of 2020. I had been working as a corporate recruiter for years, and had even owned a children’s clothing company for three years. I’ve always had an entrepreneurial soul, and it had been a dream for years to be a full time business owner. Read more>>

Nancy Nu Nguyen

The BIGGEST risk I ever take was leaving my family business to follow my intuition. There was a deep passion for me in beauty, entrepreneurship, and self discovery. There greatest achievement was failure, that was the only I learned to pick myself up and do it again. I knew if I sat there and wondered, “What if’s?” , I would end up driving myself crazy! Looking back in my twenties to my twenties to early thirties, I took so many risks to make up for all the years of being shy. The young version of me was all about the comfort zone. Because it was SAFE. No failure would Take action that I would be part of. Read more>>

Joshua Stuart

Starting my business is probably the biggest risk I’ve taken in my life so far. Since I was a child I’ve always loved pizza and it has always been my favorite thing to eat. When I was in college I was a business major and the point of me getting my degree was to figure out mistakes that can be made in new businesses. It wasn’t until my 2nd year that I realized I wanted to be in the pizza business. Originally I wanted go the franchise route with a pizza place based in New Jersey. Read more>>

Gina Barosy

Each job opportunity I’ve landed I took a risk on. I was unsure of what my purpose was until I found it by working my way up in the corporate ladder and finding myself through meditation. I believe that the opportunities that are in front of you aren’t luck it’s what was meant to be for you and no one can take that away from you. Applying for jobs can be tedious and honestly there is only one job that I’ve applied for and gotten. All the jobs that I’ve gotten is because a stranger walked in and wanted me on their team. Read more>>

Dominique Kirven

At some point in your life you take a risk right? I know for me taking risk seem the only way to go. I always hear the saying no risk no reward. I defiantly believe in that saying because my life is a true testimony of that reward. I want start off with my idea of really working for myself FULL-TIME!!!! It was the biggest risk I took during the pandemic. I was so comfortable having my 9-5 until I was let go and forced to take the biggest risk on myself and sell vintage full time. Read more>>

Jon O’Neal

In the start of my music career, my path was very much at a stalemate. The current project I’m involved in started as a band and after a while, things fell apart. I decided upon myself to continue to pursue this endeavor on my own terms and wasn’t sure of the outcome from this decision. Almost three years since that decision, my musical journey landed me many opportunities including working with people I looked up to in my genre of music. I never knew that taking that risk would lead to where I am now. Read more>>