You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken.

Sarahi Mena Enriquez

Starting my business has been the biggest risk I could have taken. I was 22 on my last 2 semesters of college, majoring in Psychology, hoping to advance to my masters in Marriage and Family Therapy. On the side, I had a passion that involved decorating of any kind. I was a bridesmaid in 3 weddings in 4 consecutive months and I fell in love with getting the bridal showers all beautiful, or figuring out creative favors for their upcoming weddings, or anything that allowed me to get creative in transforming a space. Read more>>

Laura Drake

After riding behind my husband on his motorcycle for more than 100,000 miles, I learned to ride my own. I took the Motorcycle Safety Foundation’s course, passed it, got my license. My husband had bought me a motorcycle for my birthday. Read more>>

Talen Arce

The biggest risk I took was getting my real estate license because it meant shifting my mindset and skills to adapt to a foreign career that I had no knowledge about while being unaware of the outcome. A friend of mine who’s a loan officer recommended that I consider becoming an agent when at the time I was working as a low-paid marketing director and late-night restless bartender. Read more>>

Sarah Fenerty

I’ve always been someone who likes to have multiple irons in the fire, and for a long time I kind of got off on how many different things I could be juggling at once. In my early twenties, I had endless energy. At 23 I started teaching high school English at my old high school with almost no teaching experience. Every day felt like an endless stream of creating lesson plans from scratch, learning how to act as an authority figure to kids five years younger than me, grading, and conversations with parents. Read more>>

Jose Martinez

The biggest risk I’ve taken is becoming my own boss. I was in a very comfortable serving job with one of the biggest theme parks which provided and allowed me to live very comfortably. When I took the leap of faith to work for myself I found myself in a very unfamiliar position where I was no longer able to show up, work a few days, and pay my bills for the month. I had to build a pretty thorough budget, and maintain it. I knew I had to grow the business and live in the unknown. Read more>>

Carla Lutz

Growing up, I had a lot of preconceived notions of what being a successful adult looked like. I thought it meant going to college and earning a degree, and having a job working a 9-5. The idea of starting my own business from the ground up, let alone being a boudoir photographer, didn’t exist even in my wildest dreams. To me, photography was “just a hobby” that I enjoyed in high school and college. Read more>>

Regina Craig

The risk I took completely changed my life. In 2004 I was working loss prevention for Macy’s and I would do so with a full face of make up on, and the girls that worked at Mac Cosmetics would always ask me why I wasn’t doing make up. I was confident in doing make up on myself but didn’t have the skills to do it on anyone else so I never took the chance because I was afraid. Read more>>

Roxan Krueger

When I started my bussiness I was doing my full time 8 to 5 job. My bussiness was more of a weekend hobby. As I was progressing, I started losing sleep to catch up on my busssiness orders. I work 7 days a week and will have 4 hours of sleep on regular basis. I took the risk of giving up my full time job to establish and focus more on my bussiness. So far, it has been good, I have goals and working hard to it so I don’t regret choosing my passion over my full time job. Read more>>

Lorde Astor West

My company was in the tenth year of business revenue was up, we had our pick of projects, referrals were flowing in, and our software products had reached a level of maturity that allowed us to increase our margins exponentially. Read more>>

Sarah Davis

Magdalena Tarot has always been a risk. It was a risk when I invested in the basics to start an online Tarot business (like getting my own domain). It was a risk when I opened an Etsy shop and added witchy and kitschy vintage, antiques original clothing designs to my brand. But my biggest risk I’ve taken so far is my independent publishing ventures. Read more>>

Dalai Guzman

My name is Dalai and I’m a full time artist. Being an artist is not that easy but when you find something that makes you different everything changes. At a young age i started being around every kind of art, dancing, drawing, painting, sculpting. At 15 years old i Took my first makeup classes and after that everything went really different. my mom and i thought about make it a career and thats what happend. Read more>>

Chante Joanne

Yes! When I had my skincare brand, I was 24 years old and I started it very spontaneously and sort of just for fun without any real goal, purpose or intention behind it and it grew pretty quickly in it’s first year! At the time I was the Marketing Coordinator for a Luxury Yacht Brokerage in San Diego and we had got the news that they were going to be closing our San Diego office. Read more>>

Stephanie Hernandez

I am my toughest critic. So taking a risk was scary for me because even if I have the experience and knowledge in what I do, I always second guess myself. I suppose that’s apart of the process. Taking what essentially started out as hobby in nails and makeup and making it a full time career, was definitely a risk. Not knowing if I would be able to grow my following, my clientele, etc. not knowing if I’d be able to contribute to household bills by doing what make my soul happy. It’s a risk. Honestly, betting on myself was the best thing I could’ve done. Read more>>

Monique Timby

My story may look like everyone else’s grief story, or it may look completely different. I grew up in what was once a small town that quickly grew into something none of us locals could have imagined… I never once thought I would be a victim of trauma & violence. I don’t think any little girl or boy thought “Wow, thanks for bringing me into a world where I’m about to be wrecked with an insane amount of emotional damage and then some. Maybe add some death in there, maybe some sexual abuse as well” Read more>>

Lady Obsidian Rain

Like many, I grew up with pleasant and traumatizing experiences and for me, art was my safety, be it music, drawing, or writing. At one point, I wanted to be an artist, inspired by comics, mangas, and cartoons like X-Men, Gargoyles, Sailor Moon, and Ronin Warriors. I would draw and write storylines; I would journal my thoughts about life. Read more>>

Braxtin Angelo

As a disabled person, daily life can absolutely feel like a risk. Ironically, even with all of that, believing in my self and my own abilities has always felt like the biggest risk. I remember the first time I created an online group and truly believed in myself. Watching my art being sold and shipped sparked something in me I always knew was there, but always felt so out of reach. Read more>>

Jenn Henry

To “take a risk”, by definition, is to expose (someone or something valued) to danger, harm, or loss. Funny how it’s a completely relative term that boils down to our own connotations of perceived “danger, harm, or loss”…the options we see at any given time, and the plausible consequences we are willing to accept. The choice is always ours; fear the mitigating variable. Read more>>

Christian Ellis

Our podcast started out as a group chat and we were nervous about branching out because we’re talking about virginity, sexuality, and church stereotypes, and those topics could change the way people think about us. Many of the people in our families had no idea about our real lives until the podcast. Discussing our upbringings, problems with the church, and our own mental health journey was a scary step. We made the decision to lay things out on the table very boldly and without remorse. Starting the pod was a very great decision but definitely a risky one. Read more>>

Ryan Thorbjornsen

Being an artist, you have to risk everything. At the start of COVID, I was working as a Remarking Logistics Supervisor. It obviously wasn’t what I wanted to do with my life but it was safe. I had a steady paycheck, company car, and not many financial issues. Despite the safety, I was considering taking a few months off from work, or even quitting to pursue music exclusively. Read more>>

Breanna Markwell

Taking the risk of following my heart and chasing my dreams to open up a wellness center has been challenging and rewarding for the soul. Without the challenge the reward would not be as beneficial because we learn from the hard times as well. The joy of investing in myself and being able to ask myself what’s best for me and what I really need to heal and change, so I can give that back to the world and be the best version of me. Read more>>

Evalena Matlock-Corley

If someone asked me if I consider myself a risky person, I would immediately say “NO!” However, when giving it just a minute of thought–my life story says otherwise. Let me tell you how. I was raised in East Cleveland, Ohio. Though once a fine suburb of Cleveland, inhabited by millionaires, it was far from fine when I left in 1997. Read more>>

Victoria Holland

Before opening Birch On Main, I was a regional Recruiter for Aveda ( A luxury hair care line) I have always loved people and went to Auburn for HR. Recruiting Was so much fun out of college but I soon realized I was spending more time traveling then spending time with my friends and family and quickly realized this was not the life I wanted. Read more>>

Rotem Alima

While many people say that they love risks and getting out of their comfort zone, I have my life as proof. Opening my production company in LA was probably the most significant risk I took. It was 2020, years of Covid 19, and for many, it felt like the world was coming to an end. Hollywood was literally a ghost town, and no one knew what the future held. Read more>>

Sophia Sophia

I was covered in sand and laying in the sun on the beach in Cape May, NJ during my family’s annual summer vacation in August of 2021 when I decided, after years of working in the service industry, I was going to quit my side hustle of slinging tacos with too much aioli and go full time artist when I returned. Read more>>

RAPHAEL AQUI

When starting the journey of entrepreneurship I realized there was a lot I didn’t know that truly went into the process. I thought it would be simple you know, get an L.L.C and that would be all you need. The saying it takes money to make money never became so real till I began the actual process. Read more>>

Shay Koloff

My success in entrepreneurship came from taking risk alone. I have never been afraid of taking the unknown leaps and when it came to business, many times it felt like I had no choice but to jump! Many lessons and rewards have come from doing so. I moved here to Colorado in 2020 and within those 3 years I have expanded my business more than I ever imagined all because I was never afraid to make decisions and take the risk to succeed! Read more>>

Liza Sperry

There is a great quote by Paul Tillich that is “Decision is a risk rooted in the courage of being free.” When we founded Talley-O Design 10 years ago (we’re celebrating 10 years – yay!) we knew we were taking a tremendous risk in venturing away from agencies and firms. Read more>>

Katrina Henderson

In March 2023, I took my biggest risk during my daughter’s 21st birthday celebration in Mexico which was a life changing experience. For her celebration, she had one requirement for my husband and I on this trip and that was for us to go atving with them. We thought that it sounded like fun because we have always wanted to go. Read more>>

Sara McDonald

When I first started this band, I was 23 and had no money or means to really get anything accomplished. My friends played for me for free, I never made a profit from shows and I was a terrible bandleader. The NYChillharmonic used to be 22-pieces, I eventually reduced the overall size to 18 – replacing some doubling redundancies. Why have four trombones when you can have two and a sousaphone? Read more>>

Hannah Brown

I feel like my entire professional career has been built off of taking small (and big) risks… I was working as a Visual Merchandising Manager in Louisville, KY when I got the call to move to Houston, Texas to work at a design firm in Purchasing… I had no idea what I was doing, but I took the job and a month later I was living and breathing in a totally new environment. Read more>>

Tamara Leigh & Nikki Theroux

Starting with an answer that many of us can relate to, creating a company is a big risk in itself! During the pandemic, as dancers, we and so many of our creative collaborators lost our work. We wanted to find a way to create community again. So in 2021, while temporarily living in different cities and with only out-of-pocket funding, we decided to start Wldflwr Dance Collective. Read more>>

Lisa Clontz

In the fall of 2021 I took the risk of diving into Web3 as a very new space with emerging technologies that are not widely understood. It was a risky decision as it called for me to stop being a solopreneur and start working with cofounders. Read more>>

Preston Williams

Starting our brand, while in college in Massachusetts, was a risk. Having no prior technical fashion knowledge or understand the business of fashion, we set out to learn as we went – going as far as adding Fashion Merchandising as minors in college, connecting with local creatives and investing in our vision saw a lot of trial and error. Read more>>

Nicole Alexander

I started Ivy Alexander during the pandemic after I noted that strangers would approach me while dining al fresco and ask me about the bag hook I was using. I thought that now more than ever, people wanted to keep their bags off the ground and germ free. But the purse hooks I was using weren’t made well. So I endeavored to make a better, more elegant version. Read more>>

Vanessa Matibag

At the outset of 2023, my career took an unexpected turn that left me feeling unsettled. I lost the position I held for 17 years with the organization and found myself experiencing a range of emotions – anger, fear, and sadness. I went through all the stages of grief and was unsure of what my next steps should be. Until then, I had envisioned spending the rest of my professional life with that organization and preparing for retirement. Read more>>

Adam Starek

I went to Colorado College and majored in Philosophy. I ended up transferring to CU Boulder, and the same year my parents began construction on three really unique post and beam straw bale buildings on their new farm (our childhood home burned in the Four mile canyon fire years before). I decided to defer my application to CU for a year to work as a laborer, and then a carpenter for the General contractor doing the construction – Leaf Running-rabbit (Owner of Running-rabbit Fine Art In Home Building). Read more>>

Andrew Gonzalez

Oooof. Probably first big risk, was graduating out of college with a degree and not using it at all. Instead I really wanted to start a screenprinting shop. So I did. I hired my friends, and fired my friends. It did well and then not so well. Typical 19-year-old trying to start something behavior. Read more>>

Chad Huskins

A very large risk you take as any creative person trying to turn it into a living is that it simply isn’t as reliable as, say, a job you pick up down the street by submitting and application or resume. Those jobs have hierarchies of titles, ranks, positions with specific job titles and requirements–in other words, “have this much experience and a bachelor’s in that, and then you can expect X amount of pay, for a few years, and you should expect to move up in the company by X amount of years.” Read more>>

Krystal Martin

I gave up my childcare career an just decided to pursue the idea of owning and operating a skincare/candle company. I knew I wanted to create products that solved common pain points and created a non-toxic solution to skincare, as well as candles. In the process of leaving everything behind I knew that this risk was worth taking. I began to create a vision of what I wanted to create and how I wanted my potential customer to experience it. Read more>>

Tatiana Arias

In business and in life, I believe taking risks is necessary. Stuff happens, live your life. If it doesn’t work out then it’s not meant for you. Something bigger and better is coming. I have learned to always trust your gut. The only thing we know in life that is for certain is, “Things are about to change.” To make a long story short, the biggest risk I have taken in my life was moving to Miami, Florida to what I thought would be … the beginning of my fashion career … It was NOT. Read more>>

Pa’Koulajp Lee

The biggest risk I’ve ever taken is starting my business. I knew that my parents wouldn’t support this path of mine. It was so new to me and I had absolutely no idea how to run a business. I am the oldest of 4. My parents are refugees from Laos and my siblings and I are the first generation born in the US. As the oldest, first gen, AND, a daughter, I had a lot of expectations. I was supposed to be proper. Read more>>

Justin Scott

In the beekeeping world its a lot about large apiaries. Beehives on pallets moved across the US pollinating and chasing the honey flows. This is the commercial side of beekeeping. Another side of beekeeping is backyard beekeeping. A person who keeps a few to a dozen or two colonies. Maybe all in one spot or maybe on an outyard. Then there is the sideliners. They keep a a good amount 50 to a few hundred colonies. Read more>>

katheryn labosky

I was widowed young with children to support. My life was full of risks. I worked at a college for a degree, and landed a job afterward with the degree, as a Chief Enforcement Ofiicial for a Municipality. I then took several Civil Service tests and became FEMA certified. I started my business with 54 dollars and a half-functioning computer. I invested in land. Read more>>