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.

Daren Osby

I stopped playing professional baseball to pursue my music career. I was a pretty good baseball player but I decided that wanted something different in my life. I have always made music so the decision to focus on my music career was easy and simple. I was of course nervous and scared because I was leaving a profession I have been doing all of my life but I knew at some point if I wanted to be an artist that I would have to leave baseball alone.  Right now it’s still a work in progress but everyday I get closer and closer to my dream.  Read more>>

Yasha Chapman

In the fourth quarter of 2022, I took one of the biggest risks of my life: I resigned from my role as an Instructional Coach and started my own educational consulting business, Elementary Education Evolved, LLC. At the time, I loved the work I was doing, but the work environment had become toxic, and I found myself misaligned with the educational philosophies of the people around me. On top of that, I had just experienced a profound personal loss—my aunt and father passed away within 24 hours of each other. These events caused me to reevaluate everything in my life, including my career. Read more>>

Erika Vaught

The biggest risk I’ve taken so far is moving my career and business from Detroit to Los Angeles. At the time, I’d been behind the chair for about 11 years. I specialize in creative color, which can be a niche offering in some markets. I was doing my best to build a clientele open to what I wanted to create, and was blessed to have a community of people who were into it, but I knew that community would be much larger in a big market- especially Los Angeles. After bugging the amazing people at Hair for over a year, I finally got an opportunity to meet them and join the team and the risk has paid off in a major way. It was terrifying, but it’s incredibly rewarding on the other side of it. Read more>>

Minister Slugger

There was a moment in my life when I had to make a decision that completely altered the course of my journey. You see, I come from a background that many might not expect. I come from a music background, being a music producer to be exact. When I graduated high school music became my career choice and that’s how I made money. But also, I dabbled in the streets and hustling was another source of income. For years, I lived a life that was about survival, making decisions that were fueled by selfish ambition, and the pursuit of quick gains. But deep down, I knew that wasn’t my purpose. God had something bigger for me. Read more>>

Javier Villalobos

In street and documentary photography there are always small calculated risks, a lot of the time while you’re contemplating these risks the moment you’re envisioning passes. There really isn’t a, “I’ll circle back and get that photograph later,” kind of mentality. If you see it and you’re thinking about it then you should take the photograph. I’ve thought about specific photographs that I’ve missed days and maybe even weeks later. These calculated moments have to be decided on quickly, almost without thinking— instinctively. This is where the possible or potential risk or conflict comes into the play with acting on instincts, however, these moments are few and far between. Read more>>

Melisa Pietrafesa Nora Lamela

Leaving stable professional careers to support our husbands’ growth was undoubtedly one of the biggest risks we took in our lives. For us, Melisa and Nora, this meant not only changing countries but also redefining our professional identities. We both had promising careers in our respective fields: Melisa in the legal sector and Nora in corporate leadership. When our husbands’ job opportunities took us to new destinations, we faced the challenge of starting anew. The decision to leave behind what we knew was not easy, but we felt it was the right step to support our families and to discover new opportunities. Read more>>

Motown Maurice

America, 2010, a time of mistrust, division, and unrest. It was a time of fear and violence. Protests spanned the nation. As tension endured, people had to pick a side: Team Coco or Team Leno. It was one of the greatest battles in late-night television history. It was also a peculiar time; everybody seemed to be getting a late-night show. Less than a year prior, NBC welcomed Late Night with Jimmy Fallon, followed by The Mo’Nique Show on BET, and Lopez Tonight on TBS. Every famous comic wanted a piece of the late-night pie, as did an unknown photographer in Tampa, Florida. Read more>>

Greg Gorga

Maybe the biggest risk I’ve taken is getting into a metal cage at least 18 times and going 30-feet down into the water off of Guadalupe Island to see Great White Sharks, and often they came within inches of our cage. But I am a big believer in taking risks, and I encourage my staff to try new things all the time. I’ve let the staff step out of the box many times here at the Santa Barbara Maritime Museum (SBMM). We’ve held speed dating events, dance performances, opera on a tall ship, hosted a Harriet Tubman performance, tried new education programs like Maritime on the Move, which garnered national recognition. I think taking risks does many things. First, it breaks the monotony, so it keeps life and work interesting, it opens you up to new ideas, new audiences, new relationships, and teaches you new lessons, because generally new actions don’t always go perfectly. But we learn more from our mistakes than from our successes. Read more>>

Mackenzie Bradke

I’ve always been a people pleaser. When I was in high school, I remember someone asking me why I apologized for everything. My response? “I’m sorry.” I did things that made other people happy. A lot. And then I couldn’t anymore. In college a longtime friend became upset with me for making a decision that was mine to make. I struggled to understand why a choice that was solely mine and wasn’t hurting this person, would impact them so much that they could be so judgmental about it. I remember calling my mom asking her if I was really that bad of a person for having made this choice. I decided then it was time to live my life for ME. Read more>>

Dirk Fenstermacher Jr.

As an actor, I always knew I was destined to be in Los Angeles. It was never a city I longed to live in. It was part of some pilgrimage that I could not avoid. It would of course require me to uproot my life from my home state of Arizona. It never struck me as something that was risky or sacrificial, in part due to my naivety. Though I never really felt completely at home Arizona, it was familiarity and security. The plan was to leave after me and my friend Eric Williams graduated so we could live together in the city. The plans fell apart when it came to light that I needed to graduate early. I had no job at the time and no real prosects left in Arizona. So, with $175 to my name and a help from my mom I took the leap. I risked complete and utter failure to chase a career that leaves many high and dry. I’ve gained much more than I have ever lost in that choice I made 7 years back and I have become a better artist, son, friend and a man for doing so. I have built a space for my work in this city, and I continue to peruse my goals with the utmost tenacity.  Read more>>

Chinie Go

A few years ago, I found myself at a crossroads. I had a secure job, a steady income, and a comfortable life. But deep down, I felt unfulfilled, as though I was living on autopilot. I wasn’t unhappy, but I wasn’t living in alignment with who I truly wanted to be. I had a vision for something bigger, something more meaningful a desire to inspire others, especially women like me, to embrace aging with grace and strength. But the reality was, I was a single mom, navigating the challenges of perimenopause, aging, and starting over from scratch. It felt overwhelming. Read more>>

Jessica Murphy

As a single parent who works in mental health many of my stories start with taking a risk. But by far the biggest risk I have taken in recent years is opening Based Gift and Art Store. We had the opportunity to lease and transform the former Cafe Meow at 2323 Hennepin Ave. Jumping in while funding that was promised didn’t come through running off a prayer, a dream, and the belief in our mission. Based offers a space for people facing housing instability to make and sell their art. We also accept donations and anything that is donated to us goes right back into the community for free.  Read more>>

Jenny Vice

When I think about the very definition of an entrepreneur, especially one driven by a creative process, risk is pretty synonymous with what it means to be a business owner. As we are currently preparing to celebrate a fantastic milestone of business ownership surpassing our first year in operation, I think about the numerous risks, small and large, that we’ve taken to get us past this threshold. My husband, Todd, and I were both high performers in Corporate America…. but we always wanted to own our own company. Our relationship with risk has been a stair step approach over the years; one that has been measured and calculated. Read more>>

Hannah A. West

One of the most significant risks I took was starting my own paranormal-themed brand, The Paranormal Lounge. For years, I traveled to incredible, haunted locations for my TV work, which deepened my passion for the paranormal. These experiences continue to inspire me to create something that is entirely my own, a space where I can blend my love for the spooky side of life with my creative skills and have a blast doing it! Read more>>

Yolanda Smith

2 Timothy 1:7 says, “For God has not given us the spirit of fear; but of power, and of love, and of a sound mind.” This verse has been my anchor throughout life, especially when it came to taking risks. I’ve never shied away from bold moves, but one of the biggest leaps I ever made was in August 2022 when I decided to leave my job of almost 20 years. For almost two decades, I dedicated myself to a mental health agency, pouring in my skills, experience, and passion. However, over time, it became clear that the leadership no longer valued the contributions I brought to the table. Despite my tenure and proven ability to shape and lead departments, I was overlooked for a promotion that I was not only qualified for, but had already been performing the duties for. That’s when I knew I had to make a choice. Read more>>

Lilach Mazor Power

I never planned on starting a cannabis business, but when Arizona legalized medical marijuana in 2010, I knew I had a rare opportunity to not only enter a new American industry, but help shape it. Entrepreneurship often goes hand in hand with risk, but this endeavor was challenging on another level. My family and business partner at the time were hesitant since the risks seemed to outnumber the rewards. The federal government wasn’t clear on their position and people were getting arrested in other states. Additionally, because of the hazy legality surrounding cannabis operations, we did not have access to traditional banking and loans and had to self-fund the venture. Another barrier was the steep learning curve. I didn’t know how to grow cannabis, let alone at a commercial level, and early on it was difficult to find experienced employees who felt comfortable working for a cannabis business. Read more>>

Ramiro Leal

One of the biggest risks I’ve taken in my life was leaving everything I knew behind in Monterrey, Mexico, and moving to Los Angeles to pursue my goal of becoming an actor. At the time, it felt like a massive leap into the unknown—new city, new culture, and a fiercely competitive industry. It wasn’t just a career shift; it was a life-changing decision. The backstory is that acting and storytelling were always my passions, but the idea of making a living from it felt almost out of reach growing up. Read more>>

Duke Domino

Taking a risk is a scary, yet rewarding action. Whether that’s deciding which career path to take in life, or even the simple things such as meeting new friends. These risks are what lead to a greater purpose in an individuals life. Before becoming the front man of The Definitive, Duke Domino was a solo artist who participated in a variety of performances, ranging from busking on the streets to big stages and productions in his hometown of Calgary, Alberta. He took the risk of picking up a guitar and making an impression in the Calgary music scene. Although he had many supporters, Duke also encountered many critics throughout his ongoing career. His passion and drive to entertain and bring joy to people’s lives is enough to keep him going. Read more>>

Leigh Berry

In 2021, my business partner and soul sister, Nerissa Manzi, and I found ourselves at a crossroads, both personally and professionally. We had always shared a deep, philosophical connection, with countless discussions over the years that touched on our spiritual and personal evolutions. Nerissa, a profoundly talented Master Stylist and Makeup Artist, had just opened her own salon during the peak of the Covid pandemic, creating an oasis for clients during the uncertainty and isolation of lockdowns. Meanwhile, I was undergoing my own transformation into an energy healer and herbalist, spurred by my desire to offer healing in a world that was in turmoil. Together, we began planting seeds and nurturing a vision – a salon and wellness center where we could integrate her unmatched beauty expertise with my blossoming energy healing and herbalist skills. Read more>>

Laura Masferrer

A year and a half ago I took the biggest, most uncertain and most decisive risk of my life. I decided to move to New York alone, without job references and with the hope of improving my career as a cellist in the big city. I said no to job offers in Spain that I had wanted for a long time, and decided to leave everything to start a new life in New York. One of my great passions is musical theatre, and it’s what I’ve dedicated much of my life to. After doing several productions in Barcelona and Madrid, I became the principal cellist from the West Side Story International Tour. There I learned up close how a great international production works and what it means to be part of a team of such good people and professionals around the world. My dream of continuing to grow as a cellist increased and my desire to work as a musician in New York only grew. So after a long visa process I landed in Manhattan with a cello and two suitcases, not knowing what awaited me in life. Read more>>

Charlene Goa

At the tender age of 19, I embarked on a life-altering journey that would shape the course of my future. Leaving behind the familiar warmth of my beloved West African homeland, Ivory Coast, I set out to follow in my father’s footsteps and pursue my dreams in the United States. Arriving in a new country—indeed, a new continent—without knowing English was daunting, to say the least. Yet, for me, it was the beginning of a grand adventure. I was ready to spread my wings and immerse myself in the academic world, just as my father had done before me. Read more>>

Lisa Giles

I’m a lover of risks, big and small, but the biggest risk I’ve ever taken was (reluctantly) selling my 6 figure salon I had owned since I was 19 to start over in California from scratch, broke. here’s the story; I opened a cute hair salon when I was 19. I expanded it to a 4 chair salon and an esthetician room 4 years into ownership and owned it for 2 more years after the fact. but after I expanded, I just felt like I needed more – the expansion wasn’t challenging enough I suppose. now, I always knew I would move to California because it just felt right, but I didn’t expect myself to move after dumping thousands of dollars into an expansion. Read more>>

Chris Crofut

The biggest life changing risk I have taken was following my dream of acting and filmaking. As an actor I have been turned down by many agencies, that either didn’t have time for me, others didn’t feel I was worth the risk, and then there were those that said they didn’t want to because I wasn’t a big star and wasn’t worth their time. I have also been turned down for many roles that I felt I did an amazing job at the audition(s) just didn’t fit what they were looking for in the character and their vision for their project. I just took all of this in stride and decided to take a chance on myself since others didn’t want to take a chance on me. I eventually landed roles in multiple projects from short films, commercials, to features all throughout California until I met this local director Thomas Sahagun and I auditioned for a role in his first film/ project and the rest was history. Read more>>

Trina Hannah

A big risk that I took was when I decided to quit what I loved doing most in the whole world, which was gymnastics. But when I was 14 I got into a really bad car accident that broke my ribs. That took me out of gymnastics for a few months. Which once you are out for a bit it is really hard to get back to where you were. I was trying to get to the level to where I could compete in college, so I had a really hard time catching up. Eventually it was just getting so mentally taxing on me that I had to make the hard decision to quit. I had to learn who I was outisde of gymnastics, because from 9-14 years old that was all I really knew about myself. But then when covid happened I started taking online dance classes in my basement because I was bored. Read more>>

Rashod Mckay Jr

I took a risk with this company because I positioned myself for this to be my career after college. There have been many rough patches, but I just took the “no’s” with a grain of salt and moved on. I am still learning from the no’s. I recently sat in rooms with many other CEOs, Founders, and Venture Capitalists—people who are paying themselves more than I could’ve ever imagined—because I had limited myself due to the rooms I had been dealt before I even started my business. It’s really easy to lose sight of what’s important when things don’t go the way you want them to. I am so thankful for my friends. They truly feel like a community because all of them are dreammakers. Read more>>

Gretchen Schoser

Leaping into something unknown is always a little nerve-wracking, primarily when it’s rooted in something as deeply personal as a mental health crisis. For us, jumping into the podcast world was that leap—a risk we took without really knowing where it would lead. In fact, it started out almost as a joke, something we thought we’d try once or twice and then move on. The idea came after Gretchen, aka G-Rex, had a mental health breakdown on Christmas Day in 2022. It was a turning point that forced us to confront just how meaningful mental health conversations are, not just for us but for so many people who struggle silently. We had been having honest, raw conversations about our mental health behind closed doors for a while, and one day, we thought, “What if we recorded this?”” The goal was huge. We figured we’d do a couple of episodes, maybe share a laugh or two, and that would be it. Read more>>

Khadijah Williams

In 2022, I gave up my job to follow my dreams. This was a risk because I am a single mom with two kids living in a state with no family or friends. At the time they were 11 months and 7years old. It all started on March 24th, 2022 when I became a client at Aesthetics Salon in Arlington, VA. From the moment I walked in, all I could think is “this is everything I dream of.” Every appointment I would ask my stylists Nikka and Frey about their journey and I finally expressed to Frey that I do hair as my side hustle. She called Salem over, they looked at my work and told me I need to go to school and get my license and stop doing hair in my living room. Read more>>

Anna Bruursema

In December of 2022, with no solid plan, I quite my stable corporate job to be an artist. My entire life, I have known I was an artist. This took on different forms over the years; a creative, a designer, a photographer… but my truest love has always been in the fine arts. However, being a professional artist never even came into my realm of possibility as a career direction… I remember a specific moment when my dad, a serial entrepreneur, told me that painting could always be a hobby but I should have a career in something with more stability. I struggled to decide on a creative career direction, eventually landing in graphic design. But that was short-lived and I spent the majority of my corporate career in marketing roles. Read more>>

Amy Thang

I moved away family at 23 years old to Southern California. I moved in with a friend that I barely knew. I had to rebuild clientele. I had to learn to live in an environment that I wasn’t familiar with. There was so much to learn all at once and it was really challenging. Although I was devoted to my work, I still had to learn that there was a difference in culture in the way that I had conversations with people, or it was trying to remember the street names or learning which city I was driving in, I had to learn how to cook, but most importantly, I had to make sure that I could pay all my bills and take care of myself. Read more>>

Alicia Anderson Pieri

In the fall of 2023, the startup I had been working at for nearly four years closed suddenly. I had just returned from my wedding and was taking on a new role that I was really excited about, and suddenly, I found myself without a job, severance, or a plan. I am a person who likes to jump into action in a crisis, so I immediately jumped into the job hunt. I polished my resume and LinkedIn profile and started networking, reaching out to anyone and everyone, and applying for jobs. I did at least 50 interviews in those first few months. Although it felt good to be taking action, honestly, I wasn’t all that excited about many of the jobs I was interviewing for, and I wasn’t finding the right fit. However, finding another similar role felt like what I needed to do to move my life and career forward. I had been working in tech for nearly 10 years at this point and it was what I knew and was comfortable with. Read more>>

Jeanine Young Rn

I have always been interested in the aesthetic field and worked in several cosmetic surgery practices as a registered nurse. Investing in skin treatments, good skin products, and maintaining healthy skin habits have always been a priority. About 2 years ago I realized these passions and routines I had developed could be a potential business. I took the leap and started my own aesthetic practice offering treatments, injectables, and skin care. My husband is an MD and my medical director. We have the opportunity to work together and collaborate to offer high quality, safe treatments in a comfortable setting. Read more>>

Francisco Marquez

Embracing Risk: My Journey into Filmmaking I believe that life is a series of choices. You can opt for the safe route, or you can embrace the risks. Personally, I’ve found life to be far more rewarding when I choose the latter. Here’s a story about a significant risk I took this year. Since 2021, I’ve been inspired to produce my own films—projects that could elevate my career in unique ways. Without an agent or manager, I knew I had to think outside the box and take control of my journey. Let’s be honest: many actors are caught in a cycle of refreshing their emails, hoping for auditions or for someone to discover them. I realized long ago that this wouldn’t happen for me. I’ve learned that action breeds confidence and inspiration, while inaction fosters fear and doubt. I refuse to dwell in that negative space, so I keep myself busy. Read more>>

Keitza Garavito

For as long as I can remember, I’ve had this dream of opening my own small chiropractic studio. I envisioned a space where I could see my ideal patients in an environment that wasn’t rushed or clinical—something personal, safe, and inviting for families. I wanted to move away from the sterile, impersonal healthcare settings and create a place that felt like home, where people could connect, take care of themselves first, and feel empowered to take care of others. Read more>>

Emily Northrup

Opening my small business, Sunless Silhouette Custom Spray Tan. I took a chance on myself, and honestly I wasn’t sure I could do it! When I was a little girl I was labeled the “bad child” in class, I was relentlessly picked on, left out, and had little friends. I grew up with a learning disability, which left me telling myself, “ you aren’t smart enough, you aren’t capable, don’t speak out loud you will sound dumb, they won’t be your friend you don’t even know how to read or tie your shoes”. All of my peers were far ahead of me both mentally and emotionally, and I allowed my identity to become all those things I told myself. In high school I met a guy, who I thought was everything. Read more>>

Shawn Plant

Putting myself out there as a digital video creator and hard rock miner has all sorts of risks involved. Being a DJ is the safest part about my daily routines. Being a hard rock miner has risks such as getting seriously injured or possibly worse from a mine collapse. Other risks potentially can occur during the refining process of the ore. One can get silicosis from processing precious metal bearing ore by breathing in dust particulates from quartz. Caustic fumes and vapors often occur during the smelting and melting processes. The biggest risk really is whether or not that ore you’re working with has enough values to sustain the current cost of living. As of recently I’ve been financially struggling because of a broad spectrum of issues that started in March 2023. Read more>>

Sadie Moss

It all started with my grief of losing my husband, who was killed by a drunk driver; less than 6 months later, I lost my surrogate son Quinn and his wife in an auto accident. The worst part of this was me losing my 7 year son Jonathan from my grief. (We caught up 21 years later, and he had so much anger and bitterness that we never connected again.) I hit so rock bottom and even lower. My 10-year-old son Jake came to me one day. Mom, you still have me, and you need help. Which I got my counselor said I needed an outlet for my grief. My son Quinn’s whole existence and lifestyle was about the steampunk world he lived and breathed. So, I started making hats and jewelry upcycling lamps in memory of Quinn, so a little of him lives on. Read more>>

Samantha Ward

I feel like my entire journey as an entrepreneur has been a series of risk taking. Isn’t it for all entrepreneurs. My beginning as an entrepreneur i actually was a wedding planner. Now what seems like about 700 pivots later I am a photographer specializing in elopements and branding photography. But I’ll get a little more specific. Elopements. I offer a very niche service. With my background in wedding planning, design and hospitality along with my craft as a photographer I realized I can offer a service that is pretty unique. But niching down is a RISK in itself. Closing the doors on other offers to showcase myself as an Elopement Expert was a bit scary. But I am so glad I did it. Because that is exactly how others view me.  Read more>>

Andy Williams

I serve as President & CEO of Visit Roswell, a destination marketing organization responsible for driving tourism into the city to bolster the local economy and positively impact business. A community 20 minutes north of Atlanta, Roswell largely relies on leisure tourists coming into town to experience our nature-based amenities, dine in our majority chef-driven restaurants, visit our attractions and attend our countless special events that take place throughout the year. Read more>>

Benoit Kim

I pivoted early into the non-profit and policy sector from the private sector upon graduation after working for six months due to early recognition of the endless corporate rat race without any purposeful direction in sight. I then committed to Teach for America (AmeriCorps program) teaching in inner-city Philadelphia before taking a military leave from this commitment and graduate studies at the University of Pennsylvania due to 2017 near-deployment. In this near-deployment to the North-South Korean border, I experienced my first major depression and had to acknowledge that perseverance does not always prevail, which catalyzed my venture into mental health. Read more>>

Jacob Harrison

One of the biggest risks I’ve taken in my life was transitioning from military service to running my own business. I had a solid career path in IT, but after leaving the military, I felt drawn to something different—something more aligned with my passion for health and wellness. That’s when I decided to open Deep Wave, a wellness shop in San Diego. It was a huge leap from everything I’d known. The risk wasn’t just financial—although that was certainly a major factor—it was also the fear of venturing into a completely new industry, leaving behind the stability I was used to. I had to quickly learn about running a business, marketing, and the wellness industry itself. Read more>>