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.

Seyan Washoma

As a self-taught artist, I decided this year in February that I would take a risk and host my very own first sip and paint event! I personally love to paint, draw, or do anything involving arts and crafts! I’ve attended at least three sip and paint events hosted by others, and one day, I thought to myself, “If they can do it, why can’t I?” I began calling all of my friends and family and telling them about my huge ideas, including prizes, fun games, food menus, and drink menus as well. I began to create a flyer for my event and promote the event to those around me. I had about a month to prepare without much knowledge but what I did have was a big heart with big dreams. Read more>>

Darian Pinder

The risk I’ve taken is becoming an entrepreneur through my music. (Dp Themusician) cultivated from my living room as a coping mechanism for the passing of my mother. It is sometimes surreal to me that people enjoy my talent enough to continuously book me for shows. My confidence is definitely not in question when it comes to my skill set but I am still dumbfounded sometimes by the reach and affect I have on my community through my gift/talent from God. Read more>>

Kristy Squire

My background was in sales and marketing with a BA in Communication and MBA. I worked in corporate America for years and once I had my first child, I was struggling with the constant travel that came with my profession and began looking for ways to have a better work/life balance. I began working with an agency to possibly purchase a franchise while at the same time bringing my daughter to her ISR lessons during my lunch time. I came really close to buying in to a franchise when I happened to ask my daughter’s ISR Instructor what it took to become certified. That one question changed the course of my career forever. Read more>>

Bonnie Cahoon

I was fortunate enough to land a job as a Writer/Producer for network TV right after I graduated from USC. And I was very successful in that field for over a decade. Then I took my first Pilates class. I fell in love with Pilates in 1999. I met a trainer in an acting class (another career I dabbled in) and noticed how incredibly strong her calves looked. “I’m a Pilates trainer,” she explained. “Whaaat?” Never heard of it before. So I went on over to her studio, disenchanted with the local gym franchise where I could only hope the prior sweaty butt wiped down the stationary bike, and that I might not get hit on today. She threw me on what looked like a cross between a jacked-up hospital bed and an S & M apparatus, otherwise known as a Cadillac. I was hooked. It wasn’t so challenging that I was discouraged, and it wasn’t so easy that I wasn’t challenged. It was just right. After just one session I felt taller. I was standing straighter and muscles that had long slumbered were awakened. Read more>>

Makeda Smith

Life is a series of risk taking. Taking risks, stepping out of our comfort zones – that’s how we grow and evolve. I can recall three life changing events that directed and or/ changed the course of my life. The first was when I was 17 years old. Many of my peers were choosing to attend college locally in Chicago or somewhere in the state of Illinois. I boldly opted for Boston University, going to a city I had never been to or knew anyone in. Living in Boston for four years ‘grew me up’ beyond just academics. I moved off campus during my freshmen year and embarked upon adulthood with no holds barred. The holistic lifestyle I embrace today has its roots in Boston, where counter culture practices became my norm! Read more>>

Youssef Guezoum

I moved to L.A in …2013 and crossed 5 tough years where I experienced hardship and uncertainty about my future but never doubted I’ll make it to Hollywood. During these tough times, I worked many jobs to feed my small family composed from my wife and little daughter who followed me to LA. I took a huge risk !!! Read more>>

Miranda Raine

I’m an autistic musician and advocate for autistic people. Being open about being autistic during my music career is a risk because there’s a lot of stigma and misunderstanding when it comes to autistic people. Being open about being autistic in my interviews and social media leads me to have to be vulnerable and open to criticism. But in doing this, it has not only allowed me to pursue a dream, it has won me several Awards and has allowed me to be an inspiration to many other people like me who need encouragement to pursue their own dreams. Read more>>

Simji

3 and a half years ago, before I was SIMJI, I was a content creator but in a niche I didn’t enjoy. Then one day during the pandemic, I was scrolling on Instagram when I stumbled upon a post of a rug shaped like a cartoon character. This really caught my attention because I had never thought about how rugs were made and that they could even be something other than the typical rectangular or circular rugs we are all used to seeing. Read more>>

Tsg: Ap!

The risk? Believing in myself as I had begun the drive down an unconventional route to success. That belief is what got me to where I am today. I was only seventeen when I started recording music. Lying to my parents about my whereabouts because I knew they wouldn’t yet support the idea. Skipping classes to freestyle with my friends in random classrooms. Signing an early decision, full scholarship, to UW-Madison, to get as far away from home as I could, so that no familial shackles, nor expectations, could hold me for any longer. Plunging myself into that world of independence truly radicalized my self image, for no more, could family in my life dictate my next steps. Read more>>

Alisha Bright

Starting a business, particularly in the creative arts, is a huge risk. When you find something you are so passionate about, the dream is “doing what you love for work” and many people don’t pursue it because of the risk it takes and the fears it inspires. My philosophy has always been – if there is something you want, it’s a 50/50 chance you’ll accomplish it IF you try and 100% chance you won’t get it if you DON’T try. I would rather take the risk in hopes of succeeding, than to have never even tried. The regret of trying and failing is much preferred than the regret of never trying.  Read more>>

Josie Phillips-ross

I saw a trend with women being on depression and anxiety medication and got very curious about how I could help in different ways. This was the start of my three additional years in functional medicine school. I wanted to be able to provide the best care for my patients possible, so I received my certification in dosing bio-identical hormones through C4 at PCCA and A4M Functional Medicine Endocrinology Fellowship. Through this fellowship, I had a HUGE “ah-hah!” moment and began to heal my health: my adrenals, detoxification pathways, hormones, and gut health. Read more>>

Phoebe Dawson

I think the biggest risk ive taken was moving to Los Angeles from Australia at 19 years old with just 2 suitcases, no idea how to drive, where I was going to live, work or how I was going to get started and I had no money & didnt know a single person. I also didnt realize that I had moved here during a recession and even finding a basic job as a waitress was really hard, and all the writers in the entertainment industry were striking. As challenging and scary as it was it also was extremely motivating because I had to figure it out and I didnt want to move all the way back home and not make it. So I hit the ground running and everyday I was job hunting, went to any interview I could get, reached out to every makeup artist and agency I could find to ask to assist them even for free to get started. I got a job as a waitress and slowly over time started doing small gigs here and there and that grew into bigger ones until I was able to stop waitressing. Read more>>

Miller Opie

My adult life has been made up of risk taking. Sometimes the risks were calculated and sometimes not, and I don’t regret any of them. Even if sometimes things didn’t work out as I had hoped, I am grateful for the experiences and adventures I’ve had. I grew up in a family of makers: my mother was an artist my dad could build anything, and my sister became a carpenter. Our parents were of the “you can do anything you set your mind to” ethos and my sister and I felt safe that if our risks failed, we would be able to rebound safely.  Read more>>

Charlotte Muff

It was 2021, at this point I’d been an RN for 7 years. I was taking care of my father at the end stages of his life, marriage was in crumbles and I was burnt out on caring for everyone around me. It sounds awful but I knew I couldn’t leave the marriage I was in as a single mother of two working for a hospital as a registered nurse. Nursing just isn’t single mother friendly when it comes to schedules. I was sitting in the oncology waiting room with my dad when he shouted “what about nipples- I watched a 60minute show about tattooing them!” My dad knew I wanted to go back to school to become an NP in Oncology but due to recent events, he also knew I needed to get out of the corporate world.. So we spent the rest of that appointment on YouTube looking up videos of everything permanent makeup. Read more>>

Gary Saperstein

I would venture to say that the biggest risk I took was when I made the decision to leave the restaurant business and start my own LGBTQ+ Tour & Event Company, Out In The Vineyard. Hospitality has been my whole life’s career starting out as a busser in college then moving on up to a server and then General Manager in restaurants. It just felt like a natural fit for me.  After 25 years in the business I was starting to lose my passion for the industry. Once you lose your passion for this type of work it is time to move on, in my mind. Fortunately at that same time I started to see an influx of LGTBQ+ Tourism in Sonoma Wine Country, where I reside along with growth in the gay population in the region. At the same time I wondered why no one was talking to our community. Hence, Out In The Vineyard was born.  Read more>>

Patty Saggio

While I was a Sophomore in high school I took an elective called bookkeeping. It was during that class that I decided to pursue a degree in Accounting. I went to Pace University and graduated with a degree in Accounting. Once I started working the jobs were very specific areas of accounting but eventually I landed in general accounting. It took me about 8 different jobs to get to this as I learned what I needed to at that employer and then moved on to another. After working in corporate for 12 years I was diagnosed with ulcerative colitis and boy did that mess with my long term plans. I was out on disability for a year and realized that if I went back to the corporate world it would have an adverse impact on my health but wasn’t sure what I would do. Read more>>

Cristal Delgado

This past May, just before my 24th birthday, I made a decision that felt both exciting and terrifying. I realized that the passions I had held onto for years and the path I was on didn’t quite fit me anymore. At the time, I was working as a creative entrepreneur, helping to lead a startup that was really making waves in the community. I had found my groove in things like business organization, team building, PR, marketing and social impact. But despite everything going well on the surface, I just didn’t feel that same spark I had in the beginning. Read more>>

Ashenafe Tessema

One of the biggest risks I’ve taken in my life was creating my brand, Risk Takers International. As a first-generation American who immigrated from Ethiopia, I’ve always felt a deep connection to the concept of risk-taking. My parents took a significant leap of faith in coming to this country to provide a better life for me and my siblings. Their journey inspired me and laid the foundation for my belief in the importance of taking risks. Read more>>

Chance Sanderlin

Taking risks has defined my entrepreneurial journey, starting with my first business at 12, followed by my move to Atlanta as a 19-year-old full-time entrepreneur. With two growing businesses, I’ve been balancing the challenges of scaling them while managing life and school. This bold decision has been the biggest and best risk I’ve taken to change my life. Read more>>

Orion Queer

I’ve taken many risks in my career path to get to where I am now. Today, I’m a Healing Companion and Somatic Wizard, but I started off as a farmer. Before I moved to Los Angeles in 2019, I was a farmer in the Northeast. I grew up in rural Pennsylvania and then lived in rural Maine for 7 years, growing organic vegetables & working at a creamery making cheese out of goat and sheep milk. I even spent time apprenticing at a traditional biodynamic butcher shop in Germany so I could learn traditional German charcuterie and sustainable animal husbandry practices and bring them back to the states. I thought I’d be farming for the rest of my life. I worked at a handful of farms over the years with the intention of learning & preparing to run my own farm someday. I had dreams of opening an organic local butcher shop and getting my community into nose-to-tail cuisine. Read more>>

Valerie Wei-haas

After I graduated from high school, I remembered thinking it would be a huge risk to study photography. I felt like there was a chance I wouldn’t be able to make a living with a degree in photography, but I had this pull to follow that path and see what happens. So I went to a tech school and studied photography and videography, after graduating I said yes to any gig that came my way and began working with a restaurant marketing firm in Tulsa, OK. Now, over 10 years later, I’m still working with food and restaurant clients as well as many other commercial clients in Tulsa. Read more>>

Gabriel Alejandro

I’d never done Improv before but one day I decided I wanted to try it because I thought it would help me out as an actor. So I moved to Colombia, a place I’d never been before, to do a Long-Form Improv certificate at El Bosque University in Bogotá. It was one of the most challenging and rewarding experiences of my life. I learned a lot about myself as a performer, but also as a person. I built personal relationships with people that continue to be in my life (this was in 2018) and ti reaffirmed my love for performing and I knew I could never do anything else. Read more>>

Zachary Keely

Pursuing any passion can always be a risk. Most people set aside their true passions because of how much of a risk it truly can be. You could risk your job, home, relationships, and financial stability. When I first started my career as a musician I knew there would be risks. But at the end of the day my passion is my passion for a reason, and in my heart I knew I had to fulfill that desire to make my passion more than a dream. I have always played music but when I decide to fully pursue music I took a risk and I nearly lost everything trying to make it happen. Read more>>

Clara Lieu

I spent 16 years in academia, teaching studio art at several art schools and colleges. My dream was to be a tenured college professor, which was the perfect balance of my passion for teaching and maintaining a lively studio practice as an artist. The hustle and bustle of campus immersed me into a creative culture that was stimulating and exciting. Read more>>

Daniel Erro

In 2017, I stood on the edge of a decision that would change the course of my life. With a group of close friends in San Francisco, I decided to take a leap of faith and start a record label, the XILE Collective. We were all passionate about riddim and dubstep, genres that pulsed through our veins and echoed in the underground clubs of the city. But starting a record label? That was a whole new beast. Read more>>

D.c. Johnson

One-Way Ticket to the Unknown: I suppose the old cliché of “falling into the writing and visual creative industry” best describes my journey. I was on track to build a career in finance when the 2008 recession abruptly changed everything. Job opportunities were drying up, and just as I was wrapping up an internship at AAU in Central Florida in August 2011, my college friend called with a wild idea: moving to Los Angeles with barely any money, no job, and no concrete plan. The only thing that was solidified was our potential apartment that she found on Craigslist. Read more>> 

Misha Mullany

The story of this particular risk was unexpected. For my entire life, I had only ever considered myself an actor. I was lucky enough to graduate from a B.F.A. program and grew up doing community theater. The path was always: “Find A Way To Act On Broadway”. But like every other theatre creator, I was affected by Covid-19 taking away the ability to practice the art I love. My art. But “Pre-Covid,” I hadn’t taken ownership of my art yet. I was still reaching for some far off vision of success, spending my days in audition waiting rooms and praying for my big break. Covid forced me to become desperate.  Read more>>

Ashleigh Chevalier

Any time you start your own business, you take a risk. Any time you support a start up, you take a risk. Any time you choose a business partner or client, you take a risk. Any time you pursue art as a career, get on a stage in front of hundreds of people, you take a risk. I have taken numerous risks, and risked all of the above. I’ve been lied to, used, “played,” underpaid, lost money, paid for someone else’s mistakes, and made money . . . all as a result of taking these risks. I can say I have failed more than I succeeded, which is part of life’s greatest lesson. I am stronger, wiser, and more resilient for it. The lessons never stop, and neither does risk or opportunity. Now, I calculate risk and its consequences differently. Read more>>

Alina Macks

I’ll tell you a little about myself. I grew up in a small town, and I started working as a makeup artist there, doing makeup for holidays, weddings, and I never could have imagined that I would be doing makeup for big brand advertisements and Hollywood stars. In 2022, I moved to South Carolina and had to change my profession because I needed money, there wasn’t much work for makeup artists, plus I was super insecure about my work. I started working as a waitress and spent my free time filming videos and learning something new in makeup industry . Read more>>

Jazmine Kennedy

A huge risk I took was stepping out on faith and pursuing entrepreneurship full-time. I launched my online boutique XIXV (Eleven-Fifteen) at the end of 2021. Naturally, I was nervous because I had a full-time job that provided a stable source of income. I told myself if this is something you truly want to do then you have to take a chance on yourself. Read more>>

Micheline Bowman

Taking a RISK or as my acronym brain says “Remember I’m Strong…Keep” going, pushing, moving or whatever positive word comes to mind after that “K”! I had to keep telling myself that daily. In 2017 my job was eliminated and after 27 years of employment and being over the age of 50, I had to instantly become a risk taker. I had to figure out what my next step would be. While most people have a career they feel they will retire from, you don’t go into it thinking you will be let go. The possibility is always there if it’s not your company, but for the most part you show up, do an amazing job and the ride the waves of employment. Read more>>

Rebecca Fritz

One of the most transformative risks I’ve taken was stepping away from a predictable path and saying a full-body “yes” to creating Sutra Studios. It was a decision guided more by intuition than logic—a leap into the unknown driven by a deep soul calling to create something that could truly help people heal and grow. Over fifteen years ago, my husband and I were at a crossroads. My husband was in a well-established professional path, and I was deeply rooted in the sacred work of being a stay-at-home mom, nurturing our family. But there was this inner nudge—this whisper from the Universe that kept telling us there was more we were meant to do. We felt this undeniable urge to create a sacred space where people could explore their wellness journey in a way that honors all aspects of who they are—physically, mentally, emotionally, and spiritually. Read more>>

Patrice Malloy

Oh, let me take you back to a pivotal moment that flipped my entire world upside down—in the best way possible. Picture this: I was working in a cushy, high-paying corporate gig, wearing my finance queen crown and living the so-called dream. On the outside, everything looked flawless—big titles, fat checks, the whole nine yards. But deep down? I was suffocating. That corporate ladder was feeling more like a cage, and I knew if I didn’t make a move, I’d lose myself in a life that wasn’t even mine. Read more>>

Mackenzie Rawls

I am a professional freelance dance artist, yoga instructor and SUP instructor. One of the biggest risks I have taken was moving to NYC with no job, no connections and on a mission to find a work that challenged me, my art, my technique followed by the choice to stay in NYC throughout COVID. After graduating college from the Boston Conservatory, I moved home with an ankle injury. My favorite company had closed its doors mere weeks before their scheduled audition so I decided to apply for a high school PE job. I ended up building a full middle states approved dance curriculum at a high school in MD. It wasn’t until one of my dearest students said, “You are always telling us to follow our dream… are you?” That I realized, I wasn’t, not fully anyway.  Read more>>

Alicia Collins

One of the biggest risks I’ve ever taken was deciding to start my own group counseling practice, The Well, right in the heart of Uptown Dallas. I was tired of the stale, clinical therapy settings where so many women felt misunderstood or disconnected. I wanted to build something different — a space that felt like a warm hug, a place where women could truly open up, heal, and grow. I poured every dollar and every ounce of energy I had into renting a space, hiring a team, and marketing our practice. There were so many nights I lay awake, wondering if I was completely out of my mind. But I was driven by this belief: therapy shouldn’t feel like a chore. It should feel like coming home. And I knew that to make that happen, I needed to create a practice where therapists also loved showing up. So, we pay them well, let them make their own schedules, and support them in living lives they’re genuinely excited about. Read more>>

Addison Bowen

After starting my business and seeing great success in a short amount of time ($10K+ months in 8 months,) I was growing rapidly and yet I felt pulled in a different direction. I was contracting for health and wellness coaches and helping them grow their businesses but really desired to ultimately support and help people heal myself. I decided after using subconscious reprogramming, and breathwork myself to become a certified hypnotherapist and nuero linguistic programmer. I spent thousands and thousands of dollars on the certification, unaware of who I would even serve, what my path looked like, or what the next steps were for me. Read more>>

Lucia Sastre

The Woman Who Dared: How Risk-Taking Transformed My Life and Career Taking a risk is often seen as a leap into the unknown, a daring step that could lead to either success or failure. But what if I told you that the real failure lies in taking no risks at all? This is a lesson I’ve learned throughout my career, and it’s one I’m passionate about sharing. When I started my journey in wellness marketing, I knew I was stepping into a niche field. The path wasn’t laid out for me; in fact, it was full of obstacles, especially as a minority woman. But I was driven by a deep passion for wellness and a desire to make a difference in my community. The challenges were many—breaking into an industry that often seemed inaccessible, proving myself time and again, and navigating the complexities of being a woman in a predominantly male space. Read more>>

Delfina Correia

In 2023, my world was upended with the loss of my mother. Her passing was a profound moment of reflection, and it became clear to me that I needed to be in a new environment and closer to family. Miami, where my loved ones were, began to feel like the place I needed to be. During this period of introspection, I found myself reassessing my life’s direction. After 20 successful years as a banking director, overseeing 18 retail locations across New York and Miami, I knew it was time for a significant change. I had always nurtured a passion for health and wellness, and the idea of entrepreneurship had been a dream I kept on the back burner. Read more>>

Juliette Angelo

One of the biggest risks I’ve taken in my life was leaving the entertainment industry when I was 21. I had been living in Los Angeles since I was 13, working consistently in film and television. On a gut feeling, I decided to move to Nashville, TN when I was 21 years old. I didn’t even know what I was doing, just that I had to do it. It was chaotic and very abrupt, but I managed it somehow. Shortly after, I wound up getting sober, which lead me down an entirely new path. If I hadn’t left when I did, I have no idea what my life would look like now, or if I would still even be here. It was the best decision I ever made for myself. Read more>>

Courtney Birk Ashleigh Coffelt

One of the biggest risks we’ve taken was making our short film First You, Then I. It was a time when Everything Everywhere All At Once had just come out and we were so inspired by the film. It was also a time when we hadn’t been on set in a long time because of Covid restrictions, and the film strikes. We had been feeling down on ourselves, our creative process, and if this industry had a place in it for two girls from Maryland who just love telling weird stories. While EEAAO had ignited that spark enough to make the film, we also had a very honest conversation about this being the end of our film journey. We said that we would go into this film and have the most fun we could have, because this very well may be our last one. Read more>>

Dave Richardson

Life is too short to be unhappy. So what’s the move when you’re unhappy at your job? Time to make a change. In my case, a complete left turn out of (seemingly) nowhere. My 26 year-career in public education had run it’s course. I’d taught middle school, then high school. I’d been a high school Vice Principal and Athletic Director, and then come full circle to teach middle school again. Each of my moves had been precipitated by a need for something different. But now that I’d done all of that, what’s the next move? Read more>>

Manuel Garcia

Approximately thirteen years ago, in 2011, I found myself at a crossroads in life. Recently married and about to become a father, I was working as a diagnostic technician for electronic components at a manufacturing company that produced electronic devices. While the job provided the basics for survival, I felt stagnant and aimless. My parents taught me the value of hard work and responsibility, but the spark of dissatisfaction burned within me. Read more>>

Nick Annunziata

I truly believe that the greatest risk is trusting in yourself to pursue your passion and dreams. After working in NYC theatre, I knew I wanted to transition to television. So, I packed up everything I owned, took my cat, and drove across the country without an apartment or a job waiting for me. I placed a bet on myself, confident that I would find a way to make it work. I dedicated myself to my craft and kept pushing forward. Just two months later, I landed my first audition and was hired on *Days of Our Lives* for almost a year. Being an actor is a full-time commitment—constantly working to stay working. Every day, I continue to bet on myself as I navigate the challenges of this coveted industry. Though progress has sometimes been slow, I’m still incredibly happy I took that risk—I wouldn’t change it for the world. Read more>>

Soya Soo

To be frank, the moment I chose to pursue audio engineering in college I inadvertently started my journey in taking life changing risks, big and small. Growing up in a traditional Asian family, my parents could not see how I could pursue a career in Malaysia with a bachelor’s degree in music due to the limited job opportunities and resources. At that time, I also had limited understanding and knowledge about audio engineering as well. In addition to that, I decided to obtain my bachelor’s degree in the United States; it was like throwing myself in the Sahara Desert and try to find the oasis by myself. Read more>>

Randi Rheaa

Perusing art in college was the biggest risk and investment I could have ever taken as a photographer. It meant stepping into the Uknown, dedicating time, money, resources and energy into a passion that had absolutely no guarantees. Starting college in the arts, I encountered skepticism from many who questioned the practicality of investing in an art degree. Some believed I could learn everything independently or questioned the financial sense of perusing the path. Despite the doubts, I still chose to follow my passion and invest in formal education to deepened my skills and understanding. This decision wasn’t just about acquiring technical knowledge but also about immersing myself in a community of artist, mentors, and resources that would nurture my creativity and ambition in ways self-study couldn’t replicate. Read more>>