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.

Paula Rizzo

Taking the leap and starting my own business. I only knew how to be a television producer and did that job for nearly two decades.

And in 2017, I decided to take the leap and start my own business.

I always thought that I would be very good at working for myself because I’m, in addition to being a creative person, I’m also very detail-oriented and structured and organized. Read more>>

Callbackboard

I think the biggest risk I’ve took that changed my life was betting on myself and pivoting from being a musician to a talent manager. I started my company “The Glass Experience” 5 years ago as a production company after finalizing my decision to take a leap of faith and get into the service providing industry within entertainment. Through all of my business adventures in that field of work expanded some vital personal attributes which then led me into managing/advising a diverse atmosphere creative talent such as: song writers, musicians, mural painters, videographers, DJ’s, producers, & other podcast network entities. Read more>>

Peggy Jaeger

I’ve always been a writer. I was the kid with the pink lock and key diary when I was 8, but i never wrote down things about my life, instead I made up stories and wrote them in that book. Fast forward a few decades. I was 54 and going through the worst menopause mother nature ever bestowed on a woman. Menopause induced insomnia had me in its grips and I was sleeping 2 hours in 24. So I wouldn’t keep my husband up with me all night, I went into my home office and began writing a story that had been swimming around in my brain for a while. After 3 months I had a manuscript. I had no idea if the story was any good, so I decided to submit it to a writing contest. Read more>>

Lainey Hashorva

Whenever I’m nervous or hesitant about a decision or situation, I tell myself that if I don’t take the risk or the opportunity presented at the time, nothing will change. If I choose to opt out or stay home, say no, I know what to expect. Safety and sameness. But if I push myself to say “yes” to new experiences, stepping up or stepping out, then anything can happen. Life is so full of twists and turns and chance encounters that if we do the brave thing and show up, it can lead to so many interesting surprises, experiences, adventures and connections. I hope to make brave choices and risk taking is all about getting out of your safe zone creatively, socially and professionally. Read more>>

Alice Halley

I got my first job in the music industry when I was 18 years old, and it wasn’t really even technically a job because I wasn’t getting paid. I was the leader of a street team for a local band that I liked. I started networking and getting other jobs in the music industry over the next five years, including two years as staff on Vans Warped tour in 2016 and 2017. I was 22 at the time with a day job as a server and I let other people convince me that I was never going to make it in music and it was time for me to get a “real job.” So, being young and more easily manipulated, I decided to quit touring and stop working in music. Read more>>

Sara Glenn

My husband and I first fell in love with Italy during our time studying abroad, and when we got married, we chose to celebrate our wedding in Rome. It was then that our dream of one day moving abroad began to take shape. In 2015, we decided to take the leap and make it a reality. My husband was accepted into an MBA program, and I found a job with a tour company—an unexpected shift from my career in design. We arrived in Rome in September 2015, without any concrete expectations, figuring we could always return home once he completed his degree. But, as often happens with Italy, we found ourselves falling even more in love with the country and its way of life, prompting us to stay and build a life here. Read more>>

Stacey Brown

I’m a big believer in calculated risk. It hasn’t always been that way… I was raised in an environment where change was seen as very scary, and the only true goal in life was to keep things completely static, no movement, no change. Completely controllable.

But that’s not life, is it?! Lol.

Over the years, I’ve had to learn that risk is the only way to play this game of life! The most recent risk that I took was relocating from North Carolina to Phoenix, Arizona. Read more>>

Chapo The Brand Man

One of the biggest risks I took was launching SNKR Head Brand and building Chop Shop Boutique as an online store to showcase it. My passion for sneaker culture and streetwear pushed me to create something that wasn’t just about selling clothes but about representing a lifestyle and a community.

The risk wasn’t just financial—though investing in inventory, branding, and marketing without a physical storefront was a major challenge. It was also about stepping into a highly competitive industry where standing out takes more than just great designs; it requires a strong identity, strategic marketing, and the right connections. Read more>>

Patrick Powers

I had always known that I am an entertainer at heart. I had to put that dream on hold for a while to take care of my mother, who had numerous health issues, some of which caused her to be bedridden.
Most friends who were in the entertainment industry had been able to start their journey either while in school or shortly after graduation. I had to put a lot of projects and opportunities on hold for over a decade. We had no help other than my father who did everything to keep a roof over our head. We were just scraping by for a long time. Read more>>

Monicki Firouzmand

Music has been an undeniable part of my daily life since childhood. I was fortunate to be born into an art-loving family and immersed in music from the age of four. However, due to the significant restrictions on female musicians in Iran, particularly female singers, I never seriously considered pursuing music as a university major or a professional career, despite my deep love for it. Read more>>

Amy Mastrogiuseppe

For years, I followed the path I thought I was supposed to take. I went to school, honed my craft, and landed a job as a corporate graphic designer. On paper, it seemed like the perfect blend of creativity and stability—exactly what I thought I wanted. But the reality? It couldn’t have been further from the truth. Read more>>

Shanta Kanukollu

I am the eldest daughter of immigrant parents from India. There were certain expectations placed on me because of this role – implicitly and explicitly – and one’s that were based on the basic instincts to survive, be economically stable and stay safe in a new world/culture. This led me to initially consider the medical profession but over time, it became evident that I had a passion and skillset to enter the mental health field. Doors opened for me once I learned this and I was lucky to be accepted into one of the top Psychology doctoral programs at the time – The University of Michigan. I was also given the chance to obtain a dual doctorate in Women’s Studies and Clinical Psychology, which provided me with unique research and clinical opportunities. Despite the rigor of the program and the stresses that come with living away from home, I knew it was where I needed to be. Read more>>

Alina Ugas

One of the biggest risks I’ve ever taken came during one of the most challenging periods of my life. I had spent over 33 years in healthcare management, building a stable career that I thought would carry me through to retirement. However, everything changed when I faced a series of life-altering events all at once. While I was out on disability recovering from health challenges, I was unexpectedly let go from my job. At the same time, I had just purchased a home, had recently become an empty nester after my children moved out, and was navigating life as a divorced woman. It felt like the ground had been pulled out from under me, and I was devastated. Read more>>

Casey Dave

In 2018, I made a decision that would drastically change my life—I chose to leave my long-standing career in the nonprofit sector to pursue a path as a full-time creative. After nearly two decades of working in nonprofit organizations, I realized it was no longer fulfilling my passions, and I felt called to explore a new creative direction, whatever that might look like. Read more>>

Chris Lucore

The story starts in 2020. I was a senior at Hobart College, closing in on a dual degree in chemistry and studio art, with no real idea what to do next. Chemistry was losing its appeal, and painting didn’t feel like a realistic career path. Before I could figure anything out, the pandemic hit. Colleges shut down, and I was sent home to finish my final semester online. Not long after, I had the first of four grand mal seizures — a jarring, unexpected reset.Read more>>

Angelina Spiropoulos

Making the decision to expand Nest Seekers International into the Boston market was a bold move — one that required vision, strategy, and the willingness to take on a challenge that could redefine our presence in the city.

The real estate market in 2023 was a difficult one to be in for most agents. By 2024, about 70% of agents did not do a single transaction that year. It was late 2023 when I felt a need for some change. I never considered myself just a real estate agent. I always tried to view my career from a more dynamic perspective, as I wear a lot of different hats (entrepreneur, agent, podcast host, social media influencer, writer, etc). When you zoom out and choose to view things from more of a macro point of view, the hard times don’t seem quite as daunting. While everyone was sweating about interest rates remaining at a stubborn 7-8%, my mind was on something bigger: Read more>>

Maceo

The biggest risk I’ve taken in life is trusting my visions. I was affirming things before I even realized I was affirming them. The first example I had of that was when I moved out of state in 2016 to start a new life in Milwaukee, Wisconsin. I had never moved out of state for anything, but it was a goal that I had had for myself most of my life. I have no loved ones or friends in the state so I took a big risk coming to a new place where nobody knew me and I knew no on, but I trusted that that feeling inside me that told me that I was gonna be okay. Since then, I have established myself fully as an independent artist, funding my own music videos and projects, starting my own entertainment LLC And, starting my own home Studio to record myself and soon other artist. Read more>>

John Sundara

Growing up, I moved constantly— five elementary schools, three middle schools, bouncing between Seattle, WA, and Fresno, CA. Every time I settled in, I had to start over—new friends, new environments, new challenges. Over time, I began to hate change. I craved stability, so I made my mom promise that I could stay in the same high school for all four years. For the first time, I had a sense of consistency—I built lasting friendships, had my go-to food spots, and felt the comfort of familiarity. Read more>>

Romeo Etienne

In my journey as an actor and creative, I’ve always believed in the power of taking risks and betting on myself. Growing up in New York’s 914 area also known as “ The 9” I was surrounded by a vibrant tapestry of stories that often went untold. This background has instilled in me a desire to break away from the conventional narratives we often see in television and film. Read more>>

Anthony Campbell

Often times I don’t like to refer making a difficult or life changing choice as taking a risk due to the negative connotation that surrounds the word “risk”. I prefer to say taking a leap of faith because the point of making such life changing decisions is for a positive change or ascension in your passion , career or life. No matter the choice that’s made you will still have to deal with the pro’s and cons but it’s about what you make out of your choice and how you respond to it. Read more>>

Elizabeth Moore

Getting fired from my barista job ended up being the most important wakeup call of my life. At the time, I was working three jobs just to stay afloat—exhausted, uninspired, and barely making enough to cover bills. Some weeks, I was literally stealing produce just to eat. But even worse than all of that was the fact that I wasn’t creating. I’ve been drawing since I was four—art was always my escape, my peace, my identity—and I had completely lost touch with that part of myself. Read more>>

Ugonna Abakwue

My life has been a continuous series of risks—each one shaping who I am today. The first major leap I took was when I moved to Los Angeles to pursue a career as a stylist. It was my first time living in a city on my own, navigating an industry in which I had no formal training. I had no roadmap, but I had a vision and was willing to bet on myself. I was figuring out how to network, build relationships, and create opportunities where none existed. That experience sharpened my creativity and taught me resilience, adaptability, and the art of advocating for myself—lessons I carry with me to this day. Read more>>

Jeanne Nielsen

Opening a totally new business concept in Omaha during covid was a very big risk. I have worked in small business for all of my adult life. I found myself in a place in life where working for other people just wasn’t satisfying me any longer. My years of business experience weren’t being acknowledge and I felt stuck and under appreciated. This was when I knew it was time to do my own thing. I have a very supportive husband (Mark) who said “find what will make you happy and I will support you,” I jumped at the chance to find something that I would love doing every day. Creating and building Dundee Candle Co has been a dream come true. Open during Covid was a scary time. Opening any new business is hard work and a risk but doing it during Covid made it an even bigger risk. Read more>>

Rickiara Tyson

Risk taking has defined me in many ways in my life. Despite what I was told many times about the difficulty of different things I made sure to use my own discernment and just go for it. Nipsey Hussle says “I bet my life I’m a dice shaker.” That’s me, when I graduated HS I went to college and discovered phlebotomy was a way for me to work in laboratories like I had always dreamed, many people told me things like “it’s hard to find a job” “I’ve had the certification for years and couldn’t figure out what to do with it.” I shook them dice & bet my life for the first time, dropped out of college and took the phlebotomy course anyway. Read more>>

Tiferet Cohen

I recently decided to quit my full time job to pursue my long time dream and become a full-time musician.
This dream was with me ever since I can remember, it took me quite some time to even start. after a few years working on my debut album and try and juggle everything along side working as a SW developer, I realized it’s too much and I can’t keep going like this. I was at the verge of a massive burnout and decided I’m finally at the point of being completely aware of what’s my purpose in this life was, what I came here to do, and I cannot go back from that. I decided to leave my day job (and the paycheque!) and go “all-in” for my dreams and music. Read more>>

Laura Medicus

I was working for another designer and not at all happy in the job. My mom said, “Why don’t you just open your own company?” After I laughed and said yeah right and then laughed again, she said, “No really, what’s the worst that could happen? You find out it’s not for you and just get another job.” Read more>>

Gabriela Zambrano

It is my conviction that, to move forward in life, we need to take risks.
and I understand that we will face set backs, but they don’t define my future.
in the following lines I want to explain why I am who I am and why I am where I am.

I grew up in Trujillo, Peru.
when I was 2 years old my mom left and me and my sisters stayed with my dad, and in the mids of all the pain and confusion we stayed together. My dad took good care of us, but the pain didn’t go away. We grew up in a christian environment and faith became an anchor to my soul, but somehow I needed something more, I needed to find expression for the silent cry of my soul. Read more>>

Dylan Floyd

Sometimes life doesn’t just knock you down—it sucker punches you, leaves you gasping for air, and dares you to get back up. That’s exactly how I felt when I was fired from an agency I absolutely loved. It was one of those moments where you realize that even when you do everything “right,” life can still throw a curveball. I had two choices: I could sit in the corner, wallow in self-pity, and play the “poor me” card, or I could take a leap of faith into the unknown. Spoiler alert: I chose the leap. Read more>>

Kelsey Schiefelbein

Back in September of 2022 I decided that it was time for me to go out on my own in business as a transaction coordinator. Up until that time, I had been working full time as a transaction coordinator with a team, under a team leader and that team leader’s own LLC. It was scary and risky stepping out on my own, but I felt it was time and needed to be done. My husband was working full time as a teacher, however, he was having some problems with his health and the stressful environment at his work was not helping the situation. After a lot of discussion, we felt it would be best if he came home and homeschooled our three kids. This would give him the chance to heal thoroughly and give our kids the opportunity to learn in a more flexible environment. Read more>>

Eeland Stribling

Honestly, the biggest risk I’ve taken was quitting my job as an environmental educator to do stand-up full time. I had a stable thing going—benefits, a solid paycheck, a career I could’ve stuck with. But deep down, I knew it wasn’t me. Comedy was the only thing that made me feel like myself. Read more>>

Christopher Scott

My career has been a series of risks. Sometime they are calculated and sometimes they are done with no thought and full trust in what may come.

One that always stands out is from about nine years ago. I was working at a tattoo studio in Maryland, and planned to move with my wife at the time and our kids across the country to New Mexico. It was a smaller town we where moving to and I had never lived there, Another tattooer at the shop asked where I was planning to work (at this point it was all set up) once I got to New Mexico. I told him I had no idea and that I would find somewhere once we moved. He looked at me like I was crazy “You’re moving across the country with a family that you support alone and have no job lined up!?” I just laughed and said “No, but things always work out.” Read more>>

Patrick Hogue

Reflecting on the journey that lead me to where I am, it’s only with hindsight that I’m able to recognize the decisions in my life that so many others would classify as “risks”.

The first risk that set the precedent for where my career would lead me was in between my junior and senior year of film school, having just accepted an unpaid summer internship at a production company (Echo Lake) in Los Angeles. As I sat on the plane, flying from Rochester, NY to Los Angeles, CA, I felt a familiar nervousness in my stomach, personified by these uncontrollable butterflies that always warned me when I was about todo something that was “too much” or “too scary” to handle. Read more>>

Ashley Dildine

Introducing holistic healing through soaps, salves, and aromatic roller oils was a huge risk that I took in the business world. My goal in taking this risk was to provide consumers with a safe, effective alternative to traditional cleansing and healing options. Nature provides us with everything we need to survive, and the use of essential oils in my products helps to incorporate that idea. I created a line of soap bars that are full of benefits for the mind, body and soul, which led me to introduce what I call healing oils that can aid in calming the mind and body during stressful situations and as a meditation tool. I have always believed that nature works in our favor, and I have shown that with my products. The risk was worth it because I am able to serve multiple people with different situations and ailments that my products help to relieve the burden of. Read more>>

Bella Barajas

I’m a big believer in facing my fears—choosing to “be scared and do it anyway.” While I’m a therapist with knowledge of many tools and techniques for healing, I’m human first. I have fears and struggles too. Personally, I’ve battled performance anxiety and perfectionism throughout my life. So, I decided to face this fear head-on—like exposure therapy. I believe that everything we truly want lies on the other side of vulnerability and risk. Read more>>

Miela Foster

As an artist and entrepreneur, I’ve always believed that waiting to be “discovered” is not a strategy—it’s a delay. One of the biggest risks I’ve taken was pitching foster the studio, my design studio, to curate a solo art show. It wasn’t just about securing a venue; it was about proving to myself that I could carve out my own space and create my own opportunities in the art world, blending creativity with business strategy. Read more>>

Carina Marino

In 2021, I decided to change publication from twice a month to once a month. This was a risk. It was a risk because the newspaper has always been twice a month since the early 1900s. I would be changing the cadence. The familiar cadence for the community, advertisers, and supporters. This was a big deal. We had the potential of losing advertisers. We didn’t. I was shocked! We were not questioned why we were scaling back and keeping the same prices. We were thankful. This change proved a lot. It showed us that no matter what we need to do for the sake of the newspaper, we will be understood and trusted. Read more>>

Sara McCready

The biggest risk I took was leaving behind the familiar world of corporate structure to follow my soul’s calling after experiencing a complete emotional breakdown. This wasn’t just a career pivot – it was a total life transformation. Moving from a career in financial services and balance sheets, to creating a business and programs for mind, body and soul, has been life altering. Read more>>

Maria Mondragon

I think the biggest risk I’ve taken in my life—besides choosing to pursue a career in filmmaking (lol, still waiting to see how that turns out)—was coming out in a Catholic family and a deeply conservative social environment. At the time, it felt like the hardest thing in the world, almost impossible. But today, I couldn’t be more grateful that I did it. Read more>>

Jennifer

I have always had a passion for health and fitness. I went to college and graduated with the dreams of becoming a high school math teacher. I was a teacher for 5 years and realized my heart wasn’t 100% in it. At this time, after being on my own health journey for 3 years, I decided I wanted to invest in my education and take the steps to become a functional health coach. I left teaching after 5 school years and became a health coach full time. It was the best decision I could have made for myself, my health and my family.Read more>>

Destiny Harris

The biggest risk I ever took was starting a business while I was still an unemployed college student. Before attending Tennessee State University, I dreamed of becoming an entrepreneur in the beauty industry, but it felt like just a dream. That changed when I took a leap of faith and began making lip products by hand in my dorm room. I failed badly at first, but I was proud that I had started. Read more>>

Mónica Rivera

One of the biggest and most defining risks I’ve taken—more than once, actually—was leaving home with practically nothing to my name. No safety net, no solid plan, just intuition, ambition, and a suitcase. It’s what first led me to live in Atlanta, opened the door for me to experience life and work in New York, and ultimately taught me something invaluable: there is absolutely nothing to fear when it comes to starting over somewhere completely new by yourself. Read more>>

Laura Paisley Beck

Picture it: cleaning the house at 5 AM and finding whiskey in the Klarbrunn cans, liquor and beer bottles hiding in the closet, bathroom, waste baskets… after the umpteenth time they said how great it feels to be sober. The day prior, a client called asking about their insurance coverage while their partner was asking them why they were lying to me, and why wouldn’t they mention [specific policy-changing information]. I was done. I was done with all of it. Read more>>

Racheal Smith

One of the biggest risks I took in my business was stepping into engraving without any prior experience—I just decided to go for it.

I had been doing modern calligraphy and signage for a while, but I started seeing other calligraphers online engraving perfume bottles, wine glasses, and luxury gifts. Something about it fascinated me. I thought, I can do that. But I had no formal training, no expensive tools—just the belief that I could figure it out. Read more>>

Carmen Spillette

The hardest part about starting a business—especially in content creation—is honestly just starting. Finding the courage to begin without getting stuck in all the “what ifs” can feel impossible. The risks are real too: financially, emotionally, and with your time. Read more>>