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.

Andressa Robles

“If there are no risks, there is no story” – a saying that encapsulates the essence of my journey, where taking risks has become synonymous with living out the vivid tales that unfold in the realm of dreams.For me, the biggest risk was not in the challenges faced along the way, but rather the possibility of not taking that leap of faith. Read more>>

SAMORA SMALLWOOD

It’s so important to take risks in your creative journey as an artist-entrepreneur! And I intentionally call myself an artist-entrepreneur because there’s a mind-set, skill-sets and magic from both that are required to thrive. Taking risks is one of the biggest areas where I see artists limit themselves, and to be honest I used to do the same thing! Read more>>

J.S. Hampton

How much time do we have? I’m kidding but honestly most of my career as a filmmaker has been built on taking risks. I’ve uprooted my life a couple of times to chase opportunities. I’ve left successful jobs in search of personal and professional growth. Most recently, I transitioned from solely producing to directing and my directorial debut film, The Unseen, will be released this year. Read more>>

Alex Armitage

In late 2020 I started making YouTube videos full-time. Not long after that, my relationship ended and I was left with the decision to move out and sign a lease or try something less conventional. Since then I’ve been living and traveling full-time in my SUV for almost three years. I’ve done this all while continuing to create Youtube videos every single week. Read more>>

Nolan Jae

The biggest risks I’ve taken happen to be very recent. As I am writing this I’m currently in Australia living with my cousin. Life hasn’t been the easiest recently I’ve had to deal with a lot of loss. My great grandmother passed away last year and it’s been hard to cope with it. Read more>>

Keshawn McBride

The Risk taken was quitting my job to follow my dream as a full-time. Read more>>

Joseph Renda Jr.

Taking risks is one of the most important aspects of being a creative. From the direction of your work, submitting to a gallery, to being your own business, one of the biggest risks most of us take is pursuing art as a career. From an early age there is typically not much support, direction, or influence to treat art as anything more than a hobby. Read more>>

Catie Macken

In September of 2013, I began a five week solo trip through Europe. The trip was my gift to myself in honor of my 30th birthday. I booked my arrival and departure flight and planned nothing else. Every other aspect of this trip I left up to my impulse, moment to moment. Read more>>

Kiera Johnson

In 2019, I ventured into entrepreneurship, laying the foundation for a business that would ultimately redefine my professional journey. Owning and managing a business became my initial foray into the dynamic world of commerce. However, the story doesn’t end there; it unfolds into a narrative of calculated risks, unwavering vision, and eventual triumph. Read more>>

Tiesheedah Phillips

My father was one of my biggest supporters in everything I put my mind too. I guess you can say I am the true definition of a “daddy’s girl”. In 2021, I lost him along with an aunt, two uncles and a cousin to Covid. With their passing, I felt as though I needed an outlet, something that would be able to pull me out of a depressing time. This is when I found my esthetics program. Read more>>

Jessica Ell

The principle I use to guide my life is this: “As you go the way of life, you will come to a great chasm. Jump. It is not as wide as you think.” When my marriage ended in 2020, I left the real estate business I’d had with my former partner and got a job at a PR agency. I wasn’t sure what was next for me, but I’d learned two things about myself from my time in real estate: Read more>>

Risa Paskoff

25. 5 years ago, I was a private psychotherapist, working with children and adolescents dealing with a variety of issues such as anxiety, ADHD, and dealing with parents going through a divorce. My true passion was working with children and adolescents with disabilities. Read more>>

Vickey Easa

I have wanted to be a clinical therapist (mental health) since high school. In college, that dream became a bit more detailed to include “a therapist in private practice, working for myself.” Generally speaking, therapists in this country start out at a community mental health agency, earn enough hours to get fully licensed, and then some branch out on their own and some don’t. Read more>>

Christy Barrett

In 2023, I stepped out of my comfort zone and decided to pursue the development of my art through atypical avenues. I approached a few local gallery owners regarding the idea of a gallery showing for local jewelry artists like me. No one was willing to take on the logistics and security risks. Read more>>

Hannah Volpi

I didn’t enter the market with clear channels, I entered because I couldn’t imagine myself not trying. Risk doesn’t always assume financial context. Although when starting a new business that is the bulk, more of the risk is related to vulnerability and putting yourself out there. My jump off stemmed from the true essence of who I am, so the risks, even today, feel personal and exposed, but I couldn’t have imagined a different life for myself. Read more>>

Amanda Hart

Recently, I embraced the challenge of rebranding my business. When I founded Body By Amanda over 12 years ago, I didn’t anticipate that the name would eventually feel limiting. However, after a decade, it did just that. My work with clients had evolved significantly, delving deeper into the realms of stress management, hormone balance, and nutrition by adopting a holistic and sustainable methodology. Read more>>

Kathryn Tapper

It was the beginning of the first quarter of the year when I sat down with my friend and dear colleague who was also my nephrologist (kidney doctor) at the time. It was my first doctor’s visit with him that year (2021) and he told me that it was time to start thinking about going back on dialysis. Read more>>

Candace Black

When starting a business, there are definitely risks that are involved. A little backstory that leads to my story and risk taking started when I was young. Growing up I wish I could say I came from the white picket fence with a family that supported me in whatever career field i decided to go in, but in reality for most of us that’s not true. Read more>>

Amanda Vinet

Before starting Fully Fit Meals I sat on the idea for a very long time. I was so afraid of looking “stupid”. I was terrified to start at the bottom and build. I was coming from a place of insecurity and I often worried what others would think of me.. “oh look at her little business” “she’s really trying to meal prep” “meal prepping isn’t profitable” “that will never grow enough to ever be something” “she’s broke and has to sell plates to feed her child”, were the thoughts that ran through my head all of the time! Read more>>

Danielle Williams-McCord

I knew jumping into a world of ministry after coming from the porn industry would be risky. Anytime you shine light on darkness and expose the truth about what people find to be their enjoyment, you take a risk of being ostracized. Telling my story is still risky because you never know how you’ll be received. Read more>>

Tom Harmon

Wedding photography is actually not my first career. In my previous life, I was a police officer. I became a police officer seeking respect. Growing up smaller in stature, I felt overlooked and believed that wearing the badge would change that. Read more>>

Erica Allen

From Mail Carrier to Success: A Big Step Back in February 2018, a slip at the post office put me on an unplanned three-month break. Luckily, disability insurance had my back. But in that break, I thought of a new career. So, I took a big step, quit the post office, and jumped into real estate. Read more>>

Tommy Grasley

I’m going to flip this on its head so that maybe you find a different way of looking at risk. Sure there are all kinds of risks in life. Even the ones that you don’t take. And yet, the one risk that I’d like you to really consider, is not being afraid to follow your passion, interests, or goals. It’s also knowing that it’s not a risk if you trust yourself and what you’re capable of doing. Read more>>

Sarah Larsen

A big, life-changing risk I’ve taken is when I chose to leave my comfort zone and home in Nebraska to take my art career higher. I’m a small town girl and with the way my art career was blossoming, I knew I’d outgrown the only thing I’d even known. I’d explored plenty of art scenes all over the USA but there was only one that spoke to me in a way I felt different and that was Baltimore, Maryland. Read more>>

The Realists

We originally met through a mutual friend, Evan Upton, where we both found a common interest in rap / hip hop. We expressed how so many artists before us and even in our lifetime have inspired us to even build the courage to rap. Read more>>

Christin Lowe

The biggest risk I’ve taken thus far in my business journey, was when I encountered a remarkable opportunity that pushed me to take a leap of faith. It all started when I came across a laser machine through a crowdfunding platform, and despite having no prior experience with such equipment, I felt an inexplicable urge to invest in it. Read more>>

Rochelle Merriweather

The risk of simply starting my business was a major thing for me. Yes, I do mean major! lol There was a point in time where I felt completely lost within myself and my purpose in life. I was not working at the time due to the company I worked for decided to outsource and laid off my entire department. Crazy right! Read more>>

Danielle Anatra

As a business owner, I take risks all the time. In my opinion, it’s how you upscale your business. Those leaps of faith are the difference between staying where you are or upleveling your life. I always make decisions and take chances based off my gut. I feel into whatever it is and take action on what feels most aligned. Read more>>

Viviana Arroyo

About a year or 2 after I graduated Cosmetology school and got my license, I decided to take a risk and open my business providing luxury lash extension services professionally. I had been a home based lash artist for about a year with several clients who had been my practice models during school. Read more>>

Cassandra Spence

How this whole thing started. I had a friend at the Des Moines Social Club that told me I needed to come and teach cooking classes after I was at a low in my culinary career. I felt incapable of being in the industrial kitchen and didn’t think I was going to continue working in restaurants. He kept telling me to come check it out and I finally caved. Read more>>

Kit Cummings

Over the past 15 years I’ve been in over one hundred prisons, jails, and detention centers across the nation and around the world. From working with cartel members in Mexico, to death row prisoners in Louisianna; from prisons in South Africa to prisons in Ukraine. Read more>>

Evelyn Fuson

Recently I planned to roll out a brand new program that I felt fully aligned with and felt strongly that it was going to be a smashing success! I created the most beautiful trailer that captured the essence and set up a nurture sequence that felt more organic and relational. Read more>>

Jen Johnson

I’m a former elementary art teacher. I taught for 20 years, I didn’t retire. I quit. When our youngest graduated high school in 2020 we vowed we’d move to the coast even in the middle of a pandemic. Risk #1. The real estate market was begininning to get insane. Read more>>

Jonny Bakoulas

This one is a big one! I think one of the biggest risks that everyone has to take at life is to decide if you gonna follow your dreams or if you gonna chose a safer path. Don’t get me wrong both choices are respected. But in case you go for the first one as I did then you have to make risk part of your life. Read more>>

Joshua Nelson

A lot of people in the industry are afraid to take risks as you never know the outcome of the path you choose. That is the biggest problem in music industry especially when the game has changed (meaning it’s no longer a you have talent and a message to spread, its copy culture and spreading degeneracy in music). Read more>>

Leila Rhodes

Moving to California in the middle of the pandemic was definitely a wild risk for me but after a few struggles it ended up being more than worth it. I didn’t have a job and it was scary at first but I managed to find my way. I was in Pittsburgh where I’m from and while I love how our music scene is starting to develop it just didn’t seem like a place I could grow past a certain extent. Read more>>

Nadia Tulin

When I think about the most intimidating part of pursuing a career as a stylist, it’s the fact that there is no real roadmap to success that makes taking the first steps so intimidating, but I if you know me you know I love a challenge. The thrill of the unknown has always motivated me to push my own boundaries. Read more>>

KC Mackey

The Uhuru Movement asked me to come here and organize support for the Black Power Blueprint, its economic initiative led by the Deputy Chair, going on nearly 7 years strong now. It was a risk to move here, not knowing more than a few people or where I would live permanently or what I would do to sustain myself. Read more>>

Aamber Mckinney-Williams

One of the very first jobs that I obtained as an adult was working in retail. I worked for a big box well know-retailer in fact. That career lasted for almost 15 years (2006-2020). I worked for the company from the ages of 19 years old to 33 years old, which was most of my early adulthood. Read more>>

Bryana Holcomb

In 2010 I graduated college and was excited to enter the workforce. The excitement probably lasted for about 60 days or so when it quickly became apparent I wasn’t going to find a job in the industry I wanted (fashion), in the city I lived in (Chicago), for the pay I felt I deserved (enough to live) especially now that I had a degree. Read more>>

Jasmeen Miah

A big risk I took was coming out as autistic, especially professionally. I decided to become a therapist in 2016 and only recently found out I am autistic in 2022. I was just beginning my private practice following licensure. Part of being autistic, for me, is my directness and openness. A significant part of my mental health journey has been learning to unmask and embrace who I am more authentically. Read more>>

Musa Aden

First time I took a risk was when I was offered the role of Abdelle in the movie “Malbatt Misi Bakara” in Malaysia. I didn’t have any PTO (paid time off) at my current job, and I didn’t know what to do. This was a once-in-a-lifetime opportunity, and I had to make a decision. Read more>>

Brent’lee Williams

Opening a restaurant/cafe is a risk in itself the profit margin is so small. A successful day can literally mean 2 customers come in. I think risk is part of the daily for us. We started as a trailer during the pandemic and then jumped into a brick and mortar. Read more>>