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.

Polina Raykov

The biggest risk I’ve ever taken is quitting my corporate job with no plan. I got my degree in Integrated Marketing and Communications, before I graduated I had locked in my roll as a marketing coordinator for a national fitness studio and their headquarters and within three months I was promoted to marketing manager. I thought, this is it. This is my dream job and I’ve already made it here. I was thrilled! Fast forward about two years and I was no longer feeling that way. Read more>>

Stephanie Padhye

In the midst of the pandemic, I quit my full-time job to chase after my dreams. That is the BIGGEST risk I have ever taken, but also the most rewarding.In January 2021, I decided I had finally had enough of my corporate job. I was exhausted, underappreciated, overworked, and just fed up. Read more>> 

Madelyn Ryan

I have taken many risks in my life and in my career as an independent Yoga Teacher. From solo backpacking through South East Asia, to moving to India to work and deepen my practice; my life has been all about trusting my intuition and taking these leaps of faith. Never allowing fear to be my guide. Probably the biggest and most recent risk I’ve taken has been moving to Maui to grow my business. Read more>>

Rebecca Azor

I’m 32 years old, so while there is so much life to be lived, I know I have lived many lives and taken many risk. But one particular risk I took was getting into politics. You see, I had just graduated with my graduates degree and had plans to get back into lifestyle and fashion/entertainment journalism. I applied to so many different positions, and NO ONE was calling back. Or I was constantly reading rejection emails, and we know those can definitely make you feel defeated. Read more>>

Taylor Johnson

One thing I find in common with many people I talk to who want to start a business is the fear to take the first step. It can be very intimidating to put yourself out there for the world to see and start a business. I would say the biggest risk I took was starting my business, Heavenly Treats on Earth from scratch as a 17 year old high school student. I had no clue how much work and time it would take to build a successful business. Read more>>

Ahmad Wallace

I was working a government job for 6 years while being a business owner. I wanted to take my business to the level and that required me to dedicate more time to the business. After careful consideration, talks with my family, & prayer I made the decision to leave my good paying 9-5 behind to pursue my dreams. Most people wouldn’t dare leave a job paying 100K, health benefits, & security but I always wanted ownership and had a bigger vision for myself. Read more>>

Domonique Baez

Taking the risk of dropping out of College & pursuing a Cosmetology License was one of the biggest risks I have ever taken! It’s probably one of my most life changing decisions I’ve made for myself and has led me to owning my business. At the time I was in my first semester at community college going for Psychology my parents had encouraged me to take this route since it was the safest for my future. I knew since I was young I always wanted to do something creative and not have a “regular” job. Read more>>

Helena Kelleese Smith

I recently decided to switch from service-based consultant to venturing into an online retail business. Whew! Who told me to do that?! After the pandemic started, it was hard to shift and maintain especially because services like mine are a luxury/privilege to be able to seek out and enjoy. An opportunity came my way by way of keeping great connections and right timing, I was able to secure full-time position for my work an entrepreneur, creative, and educator. Read more>>

Drea Hull

I have always been a risk taker. In 2000 I moved away from my home town in Northern California to start a new life with new opportunities. I had a 2 year old and wasn’t even 21 yet. I left everything I knew with no job or real stability to seek out a better life for me and my son. After over a decade of trying to find my way as a single mother I found a job in aesthetics as an office manager and fell in love with the industry. Read more>>

Amber Williams

The biggest risk I’ve taken had to be starting my business on a whim of faith – no savings, no clientele and nothing but a Facebook business page and an email address. In 2014, I had been working in Corporate America for about 3 years now, my culinary school dreams had been deferred due to facing the cost of tuition coupled with the pile of student loan debt accumulated from college and I was, honestly, drifting into a depressed state. Read more>>

Alyssa Maunders

This year I made a huge life change, all three of us in Down Time did actually, we moved to LA. It was a long time coming for us, we all were feeling that 2021 NEED for change, so we did it. We packed up all our stuff and had a yard sale and moved our many instruments to California. That felt like a big risk, it still does! We are finally feeling really settled out there and just so excited to have made a change after such a long period of stagnation for everyone. Read more>>

Bianca Hernandez

The initial risk was leaving our careers in the big city to move back home to help with family. Coincidently, we both had been with our employers for 12.5 years. I was a paralegal for a great law firm and she was the catering manager for Jason’s Deli. It was a tough transition and felt like I was taking 10 steps back. We placed our house on the market and moved in with my parents until a) it sold and b) we were able to find a new home. Read more>>

Irma Parone

Have you ever thought about writing a book? I hestiated. Will people want to read it? What if it is a failure? How does one even get from start to finish? Well, I did it, and I am excited to say it is launching on July 5, but it was not as simple as sitting on a beach and writing. I have always wanted to change the world, just like many others. And as much as I believed that if I could figure out a way to articulate and lay out a book that could share my experiences and all I have learned and found success through, I would do just that. Read more>>

Calvin Brown

In our lives we take risk everyday from the decisions we make. For me I played it safe for most of my dance career. Stand in the back and never be seen or heard, but I realize I wasn’t being true to myself and my artistry so I took the leap of faith and went to Washington DC to audition for the Washington Wizards NBA dance team with little to no money in my pocket. Not knowing that the risk I was taking would lead me to joining the first team in the NBA league to go co-ed. Read more>>

Danilo

The biggest risk I would say I’ve ever taken would probably be to just pursue an artistic career. Trying to make a living or even become successful creating art is one of the most difficult things to do. It is also super misunderstood by anyone who isn’t chasing that career. I’ve been interested in the music industry for as long as I cam remember. I don’t know many people who have been fortunate like me to be so sure about what they want to do with their life. Read more>>

Marco & Miguel Peralta

I remember a time when I was about seven years of age. My brother and I were walking, and a friend asked us. What do you want to be when you grow up. I didn’t want to be an astronaut, a professional athlete, or a firefighter; I wanted to get paid for my brilliant ideas. In our industry, as in any other, taking risks will determine how far you want to go. With this statement, I don’t suggest making foolish decisions but rather trusting your desires and going as big as possible. Read more>>

Lauren Faria

Last year, after committing to Cal Poly San Luis Obispo’s Engineering program and my parents putting down a dorm deposit, I received a United States appointment to the United States Naval Academy Preparatory School (NAPS) in Rhode Island. Earlier that school year, I applied to my reach school, the United States Naval Academy though I knew I had little to zero chance of moving along the process. Read more>>

Ryan Isabell

As a business owner, everyday is a risk. That’s actually part of the definition of an entrepreneur. “The one who takes the greater risk.” I literally dove head first into an industry that doesn’t have the best track record for people without a huge name or platform. Here I am, some regular guy, with about 400 followers on Instagram, thinking about starting a clothing brand. You want to talk about risk. I had 1 shirt idea, no capital, and no following. I constantly had to put myself out there and make people see in me, the same thing I see in myself. Read more>>

Nicole Ingram

When I was diagnosed with gestational diabetes while pregnant with my daughter, Bella, I really struggled to find an on-the-go, low sugar, snack bar that was good for me and wouldn’t spike my blood sugar. I knew if I was struggling, other people out there who were looking for the same criteria were as well. I decided to create my own snack bar and start my own company without any prior knowledge of the food industry. Read more>>

India Travis.

One of the biggest risk that I’ve taken in my life is when I decided to go to hair school at the age of 26. Majority 18-year-old young ladies and was out of my element. I didn’t have any experience in the beauty industry and on a whim, decided to pursue it. Read more>>

Jademan Baker

2020 was a tough year for a lot of people and I was no exception. In September of 2020, I lost my job to COVID-related layoffs and in that moment, I had to make an immediate decision – sink or swim. I cried that night thinking how am I going to pay my bills and worried about what the future held. The next morning, I woke up with a new sense of motivation and decided to start a business – LOM & MOY. LOM & MOY is an online clothing brand that is reimagining faith-based apparel. Read more>>

Adam Bird

I would have to say the biggest risk I’ve taken was quitting my day job, and just going all in on starting my business. I was at a job where I knew more about the job than my manager. He would pull me aside and ask questions about what we can do to bring sales up for our team and get the team to listen to him more etc. Then the next day he would call a team meeting and say everything I told him the day before. I didn’t have a problem with it at first, but then he started doing it all the time. I got sick of doing his job and I felt like I should be doing something else. Read more>>

Krystal Dyer

In 2016, I was working as a Curriculum Development Specialist. I designed art programs and projects for students in schools that did not have art classes. I loved my job, but sadly all of the staff started being pulled in other directions, and the work we were hired for, was no longer getting done. I did what was asked of us for several weeks but quickly felt depressed from it. I thought I was holding myself together but apparently my boyfriend could tell I was not happy. Read more>>

Karla Barcus

In 2012 I quit my teaching job to pursue an MBA overseas. After an illness made it impossible for me to leave the country long term, I started tutoring independently. I decided to turn it into a full-time business, since at the time I was unemployed. My original goal was to pursue an MBA and then start a business offering Educational Services such as tutoring. Read more>>

Sheniqua Shanklin

The Biggest risk I’ve ever taken was on myself. When I had my 2nd child in 2017 it was a life or death event for my family and I. I spent 3 days in ICU after recieving a transfusion of all the blood in my body after a hemorrhage. Once I was home and healing I started going through this transformation of body, mind, and spirit. Read more>>

Yalini Dream

Choosing to follow my calling to be an artist was a huge risk. It was the 90’s. There wasn’t anyone on TV films, or mainstream theater that looked like me. The economy for darker brown skinned femme performers was rife with racism, colorism, and gender oppression, A clear path to a career as Tamil performer was not clear. My family is a socially conservative Ilankai (Sri Lankan) Tamil family. Read more>>

Angela Quach

There is no great reward without great risk. I learned to never settle for less. Every path taken will always have challenges; that’s life! I’ve learned that if I’m going to endure challenges, the reward should be worthy of my dreams. I had to let go of my fear of not succeeding in order to make room for greatness. I had to fill that space within me with hope, faith, and conviction. Read more>>

Dawanna Jones MPA, M. Ed.

Taking risks are necessary if you wish to move to a new level in life. You will never know what can happen unless you take a risk. I started my proofreading and editing service by taking a risk. It was not something that had ever crossed my mind. I love to read. When I was in middle and high school I loved to write poems and short stories. I think I have a vivid imagination. One night in 2013, I finished reading a book that I thought was pretty good but it was filled with errors. Read more>>

Sundele

In August of 2017, I started my professional singing journey as a background singer. Of course, ever since I could remember I wanted to be a singer, so starting off as a backup vocalist definitely put me on the right track. Fast-forward to 2022, I’ve have the opportunity to sing back up for amazing artist, I’ve been able to perform at some really cool venues all throughout Colorado, and I’ve learned so much about the business side of music. Read more>>

Loren Schmerler

At the age of 73, I have chosen to reboot my career by building a lifelong portfolio of education, experience and success stories in order to assist the next generation with business opportunities. Risks that I have taken also include: Listing and selling Businesses that are losing money. Listing and selling Businesses with no tax returns or financial statements and listing and selling Businesses with significant errors in their daily, weekly, monthly and annual records. Read more>>

Chelsea Lazard

On my right arm I bear a tattoo that says, “Risk Everything, Lose Nothing”. It was my very first tattoo. Ultimately I didn’t realize at the time that this would also set the tone for how I lived the rest of my life. Everyday I wake up, it’s a constant reminder to take a risk and bet on myself no matter what my circumstances are. I was always creative, I always felt like I had so much waiting for me in this world. Read more>>

Jake IV Lambert

One of the risks I have taken is changing my photography business into a content creation business. I chose to change my business from photography to content creation is that everyone nearby is working in photography but with that said I don’t know anyone in my circle managing the people creates a constant for people who do photo, video, and social media work. Read more>>

Leisha LaCarla

Two of the most faith-tested risks that I’ve taken both involved relocating with limited finances. I’ll begin with my relocation to Dallas, Texas. In pursuit of taking success to the next level, I financed the move using my credits cards. This is a place that I had not been familiar with prior to coming. I had been settled in upstate New York with my family. There were no family or friends waiting here in Dallas to greet me. I knew no one. It was a scary and bold move, however I refused to be controlled by the fear. Read more>>

Steve Vicera

I was born and raised in Philippines. We move to the United States in 2003. Starting from scratch at the age of 37 yrs. old. In 2006 my family and I decided to open a Personal Fitness Training and Pilates Studio. We applied for an SBA loan for $700,00.00 and was approved. We put 15% downpayment and put our home as collateral. Read more>>

Thya Sanders

With starting any business, it’s scary going from idea conception to the physical service. Especially when it comes to technology, you never know what hurdles you may come across. A business owner always has that worry that people won’t be as excited about their idea like they are, however, when makeup artists started to jump on board, we realized that the interest was really there! Read more>>

Mike Donnell

I have always recorded previous albums at major studios but where I’m at in my life right now I had to make some cuts so I decided to learn the art of recording, build my own home studio and do it myself! After countless hours of online courses and videos I think I figured it out because I have a new full length album ready to release and I’m proud to say not only am I the sole writer and vocalist, but I also recorded every instrument myself, tracked, mixed, and mastered all at home in my studio! Read more>>

Lydia Morris

Oh man! I would say in both businesses, I was jumping in feet first, with no prior knowledge of the industries. When I was 16/17 was a single, teen mom, who worked multiple places, and never went to college. So, when starting my own businesses, I always felt that not going to college was something that disqualified me. I was very wrong. I had grit, determination, a massive support system, and faith. Read more>>

EnJunaya Canton

I have always been a risk taker. The biggest risk I took was moving to Los Angeles and shortly thereafter quitting my 6 figure job to start my business. I survived by working part time at Sephora to help me learn about skin care products. I would literally survive off the sales from my online store (at that time) and the minimum wage from Sephora (where I did not have regular hours). Read more>>

Britney (Bre) Jackson

In 2019 while working as a full time school counselor, I decided to open up a mobile nail salon business, Klassy Koats Nail Lounge. The initial goal was to operate on the weekends to supplement my primary income. Everyday I consistently researched and taught myself about the nail business. I then decided instead of just hiring nail technicians and overseeing the business that I wanted to go to cosmetology school and learn the craft for myself. Read more>>

Deejay Young

One of the hardest things I’ve ever had to do was leave my college education, in an effort to pursue a full-time career in entertainment. I graduated my fine arts High School with the intent to major in English & minor in Theatre. Once I got to my college, by default, I went to what my natural instincts were, by way of my high school environment, & dove right into networking with different organizations in the school, as well as out as outside of the school as it pertains to Music, Entertainment, & the Arts. Read more>>