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.

Wayne Comick Jr

My whole life, I feel as though I have taken a risk. From transferring from my hometown high school to a technical high school in Newark, NJ (Donald M. Payne Tech) to learn about TV production, attending college for four years, and graduating with my degree in the Bachelor of Arts for Radio, TV, and Film and having an social media internship lined up. My love for TV production runs deep since I was a kid. Getting into content creation was a little nerve-racking, but I wanted to show the world my vision, my POV, while also motivating my peers, family, and social media mutuals that you can do anything you want if you’re willing to take that risk and sacrifice certain distractions.  Read more>>

Nicki Ehrlich

I never would have thought of myself as a risk-taker, but looking back, I guess I have been. I loved climbing trees as a kid. I was shy around people, but I wouldn’t hesitate to bring a stray animal home. I left home for college, choosing a school where I knew no one. My love for horses developed from an early age. My family did not own horses or enough acreage to keep one. I really don’t know where the interest came from. But I couldn’t get enough of these big, beautiful creatures who allowed us to stand near them. And ride them. There was a time I fancied myself a horse trainer, though I know some horses who might take exception to that. Read more>>

DK Kim

I never expected spending 18 months in the South Korean military to change my career path, but it did. I served as a squad leader, guiding and protecting my team. Every day was structured, intense, and mentally demanding. Somewhere in the middle of that experience, I started thinking differently—not just about leadership but also about systems, decision-making, and what makes strategies actually work in high-pressure situations. Read more>>

Tommy Browning

When I was in my last years living in Arizona, I needed a change in life and fast. I had a spiraling romantic and personal life, my professional life was in its prime and facing new changes at my former firm that I wasn’t too comfortable with for my first stint in corporate leadership, I had a close college friend who died by suicide, and I was also dealing with a personal security matter in my neighborhood. With everything in life hitting me at once, I decided the best course was to start fresh. I had my sites set for Dallas, TX for a while and was hoping for a smooth transition before summer of 2023, but God had other plans in store for me? I took a leap of faith, CTRL + ALT + DEL myself and my life in Arizona, and I suddenly respawned in Dallas. Read more>>

Niki Koss

When I decided to direct Homeschooled, which was my first documentary, I knew I was taking a major creative and personal risk. Up until that point, I had only directed narrative films — where you can control the characters, the dialogue, the outcome. This was something completely different. Not only was I venturing into a new format, but I was diving headfirst into a subject I knew very little about: homeschooling. Read more>>

Ally Dalsimer

In 2019, my 30-year career as an environmental policy professional came to a screeching halt when my position as the Defense Department’s Natural Resources Program Manager was eliminated during the first Trump Administration. I took some time off, then hung out my own shingle as writer and editor. After some initial success, the pandemic hit and my business floundered. For a time, I considered following up on one or more of the several job offers I’d received over the last year, but returning to the environmental field felt too much like doubling back. Read more>>

Rebecca J. Jones

Taking risks is important for growth. The risks don’t have to be big. It’s anything that puts you outside your comfort zone. These are the things you might fail at. However, I have realized over the years that failing isn’t necessarily a bad thing. It’s ok to fail if you learn something, pick yourself back up, and keep moving.  Read more>>

Lourdes Rosales

One of the biggest and most defining risks we’ve taken was moving from Spain to the United States to follow a dream. We—Lourdes Rosales and Ignacio Lara—co-own Rebel Strings, a company born from our shared vision: to bring electric string performances to the highest level of excellence and creativity. Read more>>

Shayne Hollifield

It all started with a significant leap of faith. At the age of 50, I decided to leave my salaried management position to pursue my long-held passion for real estate and beautiful homes. I had lost my enthusiasm for my management role, and after my 50th birthday, I resolved to take a chance on a dream. Read more>>

Andrew Morris

In 1993, I made a decision that completely changed the trajectory of my life—and not without serious risk. At the time, I was working as an associate editor at Newsday, a respected newspaper in Long Island, New York. It was a stable job with a good income and upward mobility. But something kept gnawing at me. Read more>>

Yazmin Medeiros

Since launching my business in 2020, I’ve faced numerous challenges and opportunities that have required courage and belief in myself. One of the most significant risks I took was leaving a career in biochemistry — a field I studied and dedicated years to — to pursue my passion for creating memorable events and celebrations. Read more>>

Jeremy & Ellen Sizemore

Both my husband and I have had to take quite a few risks both personally and together as business partners in order to be in the position we are at with our businesses today. Read more>>

LAVIK BHOJWANI

I came to NYC 11 years ago on a school picnic and as a 11 year old kid I fell in love with NYC and I was too young to understand this but, I felt that I had a calling from this place and I always wanted to move here in my 20s and initially I wanted to come here but because my father had some financial troubles in his business we couldn’t afford it so I applied to canada and australia and I got in the all top 8 colleges in both of those countries but, destiny as I would say during the visa process for australia there were some errors on the financial paperwork and the fees was way out of our budget I dropped it with a heavy heart and I paused moving abroad and decided to do CPA in India and I was doing pretty good but, during the second level I felt mentally burnt out and I decided to quit and I gave my family the ultimatum that I want to move to NY and well see on how everything goes and then I took an education loan Read more>>

Jemischa Albo

In 2020 I was living in Maryland, where I’m from, and I was watching Wanda Sykes’s Netflix special “Not Normal”. There was something about it, maybe it was just somebody who looked like me (Afro) doing comedy, that inspired me to want to try Stand Up. At the time I was working for a company that I had been with for almost 9 years. The thought of leaving stability to pursue something that might not work out was frightening. But over the next several months, I started writing down anything I thought was funny! During my mundane days at work, or in general life, I took notes and wrote jokes in what would be my very first Joke book. Read more>>

Amy Regan

A risk that I took was opening See Saw Art. I knew I wanted to create more exhibition opportunities for artists, learn more about being a curator, owing a business, and help build community. Through my work at the Rochester Museum of Fine Arts, I had 10 years of experience in grass roots curating, and a large network of artists. Taking the leap to run my own gallery was both exciting and scary. I wasn’t sure how a different city would feel, or if there was a need for what I wanted to create. Read more>>

Jamie Azar

Breaking the Rules to Reclaim My Life—and My Pleasure

For as long as I can remember, I’ve had a deep love for learning. I come from a long line of educators—teaching was in my blood. So, it felt only natural that I’d end up in the classroom, English degree in hand (despite the warnings that I’d never find a “real” job with it). Teaching high school English, Creative Writing, and Journalism across the U.S., and even a year abroad in Costa Rica, felt like answering a calling. Read more>>

Ameenah Carroll

Taking risks can be fun and scary. For me, life changed for the better when I took the risk of starting my own business. Before starting my business in 2022, I had a six-figure income working at one of the world’s top semiconductor companies, Intel. I was comfortable in my position but yearned for experiences that provided my life with more purpose. When the unexpected happened, and company policies of working at home changed, I found myself caught in the middle of two important decisions. Did I want to continue working for corporate America by relocating 4,000 miles to go back to the office site? Read more>>

Nichelle Jenkins

Hi, I’m Nichelle. Master Health Coach and Certified Personal Trainer. I’m named after the real-life actor who first portrayed the iconic Captain Uhura on the one-of-a-kind TV drama Star Trek. My mission is to help people at every stage boldly chart course toward their strongest selves. Read more>>

Katherine “Kitty” Harris

Taking a risk often means stepping into the unknown, trusting that your passion and purpose will outweigh the uncertainty. For me, that risk began when I chose to leave the security of stable employment to follow my deep love for physical movement. I became a certified yoga instructor and launched my own business: Secret Stash Yoga. It was a leap into entrepreneurship that required not only belief in my craft, but the courage to wear every hat in the business. I was no longer just a teacher—I became the marketing strategist, the scheduler, the financial planner, the administrator, and the one responsible for building a team of like-minded instructors. Read more>>

Jill Sigman

I build site-specific structures out of trash. Called The Hut Project, my structures are used as gathering spaces for
performance, community dialogues, micro-agriculture, food sharing, and workshops. They shine a light on issues about environmental justice,
waste equity, sustainability, and refuge. About five years after I started doing this, I was commissioned to build one
of these huts out of electronic waste in Aarhus, Denmark in connection with composer Line Tjørnhøj’s opera Tomorrow’s Child. Read more>>

Jamika Steen

One of the biggest risks I ever took was launching my food and lifestyle brand, Jay Chef Behavior, while being a full-time parent with no huge formal culinary training or big media connections. I started creating recipe videos from my kitchen, using whatever ingredients I had and turning them into bold, flavorful dishes that felt like home. I had no guarantee it would catch on—but I believed in my creativity and my ability to connect with people through food. Read more>>

Gnece Quari

I took a leap of faith as a recording artist, knowing it takes serious money to build a music career. I chose not to further my college education after obtaining my Real Estate degree so I could fully dedicate myself to this path—even though I understood the odds of making it big are one in a million , I still took that risk of being a recording artist! Read more>>

Tony Marsico

After graduating high school I pursued a career in taxidermy and worked part time as a drawbridge oiler. I realized that being a musician just might be the easier path to take. Read more>>

Darkroom Zaddy

Since I was five years old, I have lived on the same block in the Bronx, where I was raised. Growing up was difficult because I was raised in an immigrant home with only one parent, so I witnessed my mother’s financial struggles. My greatest source of motivation in life is her. She encouraged me to complete high school and somehow made it happen. In addition to looking after my two younger sisters, my mom would always make an effort to make sure I was doing the right thing, even when I was struggling. I joined the photo club in high school, and since the school possessed a functional darkroom, Ms. Joanna Wegielnik taught me everything there was to know about film. Read more>>

Isabel Garcia

One of the best decisions I ever made was also one of the most challenging risks I’ve ever taken, not just for my career, but my life in general. Deciding to choose myself, my craft, and my dreams taught me to persevere regardless the circumstances. Read more>>

Alexis Hamey

You know, it’s interesting because I’ve always prided myself on being a hard worker, someone who puts in the effort. But risk-taking? That wasn’t necessarily in my DNA. Starting my wedding photography business, though, that was undoubtedly the biggest leap I’ve ever taken. Read more>>

Atharva Tyagi

I’ll never forget the night I decided to start SMYL-Fit. I was sitting on my bedroom floor at 12 AM, watching my younger brother, Rey, pace back and forth in the hallway. He is on the autism spectrum, and ever since he was born, I have seen his struggles in trying to “fit in” wherever he goes, rarely finding a safe place where he could be himself. I kept thinking about how Taekwondo had been my refuge for 14 years, where I learned to channel my energy and find my voice. Rey deserved that same sanctuary. That night, I felt an overwhelming need to create it for him and kids like him, so they wouldn’t have to fight the same battles alone. Read more>>

Dianna Cochrane

I have taken a few risks in my life, and I would say that me and my husband have pushed into a little more of a risk filled life perspective intentionally. The particular risk I’ll talk about is when I opened my first Pilates Studio location. I had started thinking about opening a studio for a few years before I actually did. I think the thing that was slowing me down most was a little analysis paralysis (over thinking) and fear of people watching me fail. While I was in this phase I was pressing into a lot of resources that kept pointing me towards a growth mindset, and the perspective that “failure” is really a way to grow. This perspective helped me tremendously to realize that I would never make ANY movement in life if I was stuck in that fear. Read more>>

Jane E Fendelman MC

I randomly came out of denial at age 30 after watching the movie “Thelma and Louise,” that I was attacked and raped by a 16-year-old boy, when I was 12. I came from a family of good “soldiers.” Soldiers meaning… Don’t complain, don’t talk about your feelings or the past, just shut your mouth and keep marching. I didn’t tell anyone about the rape. In fact, I risk judgment even now at age 65, for laying down in print, what I am saying here. Read more>>

Kathryn M. Whiteley

Originally from a media background, I was asked on a few occasions to be a guest speaker in the School of Business Marketing/Advertising at the Queensland University of Technology (QUT) Brisbane in Queensland Australia. It was through this experience that I was approached by a professor (who became a colleague and friend); if I would consider becoming a faculty member and teach in the advertising program. I applied and soon began teaching there as a lecturer, never having taught in academia previously. A great learning curve! The role of teaching and research was rewarding, and I had some amazing colleagues and students. Read more>>

Pastel Bryant

Back in 2017, I was working as a loan underwriter at JPMorgan Chase by day and slowly making a name for myself as a part-time DJ by night. On paper, it looked like I had stability—but something inside me always longed for more creativity and freedom. Then, seemingly out of nowhere, I was laid off. What could have felt like a crisis oddly felt like clarity. I wasn’t upset in fact, I felt a calmness settle over me, almost like an awakening. Read more>>

Todd Montesi

Right now, I’m taking the biggest creative risk of my life with my project PN & FRIENDS. I’m finishing the final episodes of this acclaimed series, pouring in everything—my artistic vision, professional experience, even my philosophical outlook. It’s bold, funny, and deeply innovative, especially in how it uses AI. The stakes are high because I’m using these episodes to pitch PN as a fully backed TV series. If it doesn’t land, I’m not sure what’s next—that’s how all-in I am. But I truly believe PN has the potential to be a major pop culture phenomenon, and that belief is what keeps me going. Read more>>

Alaina Curran

The first time I ever went to California as a St.Lous Missouri native as a freshman in high school, I recorded a video of myself saying ‘Alaina if you work hard, you can live here, so work your — off.’ And here I am.  Read more>>

Haley Wells

I began wire wrapping in 2018, at the ripe age of 29. At the time, it was a hobby, but from a very early age, I always had a strong entrepreneurial spirit. Throughout my life, I found myself perpetually trying to find a way to turn my artistic passion and creativity into financial freedom. Very quickly on my wire wrap journey, I found I could make a quick buck with relatively low risk. It was never anything outrageously substantial, and certainly not enough to cover the bills. After about 2 years of making supplemental income wire wrapping, while simultaneously becoming a new mother, and temporarily becoming a stay at home mom, I found myself dabbling around on TikTok. Read more>>

Jennifer Jones

In 2011 I was between jobs. I had two young children and desperately wanted to be home with them; however, working or staying at home was not a choice, or so I didn’t think it was a choice. I was wrong. I immediately took the risk of starting my own company with no money and a lot of phone calls to people who I had worked with in the past to see if they needed any assistance on the projects they were working on. I got a lot of noes, but those few yeses took a risk on me and gave me the confidence and courage to keep going. Today I own a couple of businesses and am so thankful I was able to be home while raising my kiddos. Read more>>

Seth Menne

At the age of 27 I couldn’t believe I had just landed my dream job. My family was astatic it was a massive accomplishment. After 8 years working in the field as an electrician starting as apprentice, moving to a journeymen, then to a Forman running Large projects and now being promoted to project manager? It felt like such a Blessing from the Lord. Little did I know he was giving me this position so that I could learn the skills to be project manger and then He was going to ask me to give it all up. Read more>>

Thomas Mascola

A few years ago I tried something totally against my instincts: I bought a shiny new collector box—and left it sealed. For someone who lives for the crack of a fresh pack, that was agony. Still, I told myself I’d see what happened if I just…waited. Read more>>

Johnny J. Blair

I made 4 different long distance moves across the USA to pursue my music career. That involved leaving my comfort zones of family, friends, and steady work, and sometimes I took the leaps in less than ideal circumstances. The first time I was 17. The last time I was 54. In two of these scenarios I trusted people I shouldn’t have trusted and the landing was very rocky. In fact, the last one I almost went bankrupt and was functionally homeless for 8 months, but I rebounded. In fact, I learned and grew amazingly from these experiences, and I learned skills and built relationships that have gone beyond my dreams and expectations. Were it not for these diverse experiences I might not have the testimony I have today. I’m sober in more ways than one and am thriving creatively, economically, and spiritually. Moreover, I have a heart for service that I never had before. Read more>>

Delphine Delphine

In my late twenties, I made a decision that shocked everyone around me: I walked away from a coveted role in the City of London as a trainee fund manager at Merrill Lynch. It was a golden opportunity, the kind of position many work tirelessly to secure, with the promise of a lucrative, prestigious career ahead. On paper, I had it all. But in truth, my heart wasn’t in it. Read more>>

Dean Cycon

I have always been a risk taker. Maybe that’s the result of growing up in a broken home and on some mean streets, but I have always sen the world through my own lens and tried to create my own path. I wanted to be a lawyer to change the world for the better. I did some good work for the environment and for marginalized peoples around the world, but ultimately realized that the legal system was not a place for me. I turned to non-profit development work, co-founding the first development organization in the coffee world, Coffee Kids. My task at Coffee Kids was to visit indigenous coffee communities, discover challenges to their development, create programs and seek funding from the coffee industry. Read more>>

Dr. Parul Baranwal

There’s a saying that the biggest rewards often come from the biggest risks. For me, one of the most defining risks of my life was leaving everything familiar; my home, my family, my culture to pursue higher education in the United States. It might sound like a common tale of ambition, but for someone like me, it was anything but typical. Read more>>

Jackie Padich

Choosing the path of an artist is an ever reaching into the unknown. To pursue this archetypically challenging life is to blindly trust the next stone will appear in the path as you take each step. There is no straight shot, no roadmap you can truly follow to “succeed” in this field. It is a deep listening to your own will, intuition and the synchronistic way of the universe that guides you. Trying to make a living in this way is akin to the ancient mystic who ventured into the world with no money or shelter in order to instill full trust that the universe will provide their needs as long as their spirit is true. Very few parents would exclaim in joy if their child tells them they want to be an artist, and yet, people continue to make the courageous choice to pursue meaning, expression and passion in life. Read more>>

Ameia Mikula-Noble

Like everyone, I have a part of me I show the world and a part of me I keep to myself. It’s not as if I’m lying about who I am, but more so that it’s simpler to just be the light hearted entertainer, the younger sister who put on ‘funny shows’, or the tough one my parents didn’t need to worry about, as my grandfather would say, ‘no one is going to spit in her oatmeal’. Read more>>