The chapters in our stories are often marked by wins and losses. Getting a new job, getting fired. Getting a life-threatening medical diagnosis, beating it and getting a clean bill of health. Too often, due to a societal expectation of modesty and humility we are discouraged from talking about the risks we’ve taken that led to those ups and downs – because often those risks draw attention to how we are responsible for the outcomes – positive or negative. But those risks matter. Those stories matter. We asked some brilliant entrepreneurs, artists, creatives, and leaders to tell us those stories – the stories of the risks they’ve taken, and we’ve shared them with you below.

Brittany Roberts

At the previous job that I had, I was often passed up for promotions and painted to be an incompetent worker. Though I had been in the field for years and worked with two clinics prior, both of which valued me and showed appreciation to my hard work. At this company for whatever reason my boss just did not like me. I was constantly put on challenging clients, removed off the schedule without warning or reason, and pulled for meetings with HR without clear feedback. This really took a toll on my mental health. Finally one day after a hostile meeting I decided to just quit. I then started my business AMPED in hopes to not only help neurodivergent families, but the professionals that work with them as well. Read more>>

Sam Schmidt

Taking risks is often seen as stepping into the unknown, but for me, it was about following my heart, trusting my instincts, and making bold decisions that ultimately shaped my future. Looking back, the biggest and most life-changing risk I took was transitioning from a collegiate soccer player to becoming a Jazzercise instructor and eventually owning a Jazzercise studio. The journey has been a whirlwind of challenges, growth, and unexpected opportunities, but every step was necessary for me to arrive where I am today. Read more>>

Cassandra Turner

Making the leap to plan and execute my first out of country retreat to a place I had never been was probably one of the biggest risks I’ve taken, followed closely by starting my LLC. Putting the deposit down on the location was stomach curdling but I knew that id I didn’t take that step that this dream would never come to fruition. I did research for months on where I wanted to go and the perfect spot but once finding the right retreat center it took me almost a whole month before convincing myself to put down the deposit. It was in a place I had never been the spoke a language I knew little of but my heart knew it was perfect. Read more>>

DeAngelo & Rachel Webster

When I think of a significant risk that we have taken together, the moment that comes to mind is eloping in Las Vegas. Not only was this an obviously impactful moment in our personal relationship, but it also was the beginning of us moving in to the coaching world unified as one. One of the things that stood out to both of us the first time we met was our desire to be a part of the healing of people. We wanted to make an impact that aided in the growth of humans; leading them towards obtaining a healthy life and relationships. While we had instant chemistry, attraction and engaging flirtatious banter, this common direction gave our meeting meaning. Read more>>

Ryan Kasperek

For most of my adult life, I never truly believed I could be successful without a college degree. That mindset held me back—I told myself I needed to follow a traditional path before I could really “make it.” For over a decade, I worked in the fire and EMS field, committed to serving others but silently questioning if I had what it took to pivot, to chase something that lit me up personally and professionally. Read more>>

Faith Hagan

One of the biggest risks I’ve taken was choosing to leave a traditional, secure career path to launch my own business—Soma Studios, a virtual wellness and personal training program.

My journey in movement started early. I began dance and gymnastics at the age of three, developing a lifelong appreciation for discipline, strength, and body awareness. By fifteen, I transitioned into traditional gym workouts, making fitness a central part of my life. Read more>>

Jennifer Stukey

The Risk of Believing in Something Bigger: How I Built—and Let Go Of—My Integrative Wellness Center

Risk in business isn’t just about money. It’s about putting your heart on the line over and over again. The biggest risks I took as an entrepreneur were emotional, physical, and often invisible to the outside world. They were about trusting myself, again and again, even when it didn’t make sense to anyone else. Read more>>

Nico Field-Dyte

After many years of having a “regular job” and continuing to find the right fit within the 9-5, I found it very challenging to excel in a workforce that did little to nurture talent and ambition coming from a queer, female source (me). The same story can be told by countless women; work harder, smarter, faster and know more than your male colleagues because you have to. Damned if you do, damned if you don’t is what it turns out to be. Read more>>

Aubrey Yee

My adult life has been a series of risks taken and seemingly illogical turns. Changes in a course that appeared on the outside as ʻsuccessfulʻ but was not in resonance with my soulprint. The most recent of these twists was leaving a very stable job doing what I loved during the pandemic to focus on homeschooling my kids – itself a big leap of faith – and starting my own consulting business as a futurist. Read more>>

Isaac ANGUIANO

I went into a new job for welding for short term. ended staying for more than 5 years and took over the business. Read more>>

Ken X

One of the biggest risks I’ve ever taken was deciding to fully commit to my music career, even when everything around me was unstable. There was no blueprint, no guarantee of success, and no safety net, just a vision I felt deep in my core.

At the time, I was balancing jobs that drained me, living check to check, and fighting the doubt that comes when you’re chasing a dream most people don’t believe in until it’s “proven.” I remember sitting alone one night, just me, my music, and the weight of knowing I either had to give this everything or risk living a life where I’d always wonder, “What if?” Read more>>

Laura Stiffler

Entrepreneurship is all about risk taking, in my opinion. The first risk, and most important one I took on myself and my business venture was to leave my job and be fully reliant on the income from my business. In 2021 I was working a desk job in an office setting and I was yearning for more out of life. I wanted so badly to carve out my own path and set my own hours- I knew I could handle being a business owner… I just wasn’t sure yet how to achieve it. I began researching and obsessing over microblading techniques (a form of permanent makeup) and found an artist that I felt was incredible. Read more>>

Joshua Leverett

A risk I took was leaving somebody I truely loved to chase my dreams and be successful knowing the outcome would be they may never come back. Read more>>

Charles Huurman

The biggest risk I ever took wasn’t about tattooing — it was walking away from the life I thought I was supposed to build.

By the time I was 21, I had a house mortgage, two car loans, a couple of businesses… and the crushing weight of debt. On paper, I was a young entrepreneur, but inside I felt trapped in a life that wasn’t mine. When it all collapsed — the businesses failed, the money ran out — I hit rock bottom. Read more>>

Paul Madahan

Over the years, I realized that taking risks—the right kind of risks—is where real growth happens. It’s not about acting impulsively. It’s about preparing carefully, then trusting yourself enough to take the leap even when the outcome is uncertain. Some of the proudest moments in my career didn’t come from times when everything felt safe and certain—they came when I stepped into the unknown and had to figure things out as I went. Read more>>

Diane Nichols

My story can be long for the risk I took to get to where I am at now. I come from a long line of abused women who were meant to feel like they could do life with out a man. Watching my mom be abused by my alcoholic dad made me want more for myself. She tried to teach me to be independent and smart. Growing up I was the educated artist, I was the kid who made good grades and was artistically talented. I loved drawing and painting and anything art related. But I knew education was important and I wanted to be smart. My grandpa once told me I wouldn’t make money as an artist and needed to focus on school.  Read more>>

Alexander Laughlin

Within the first year of offering my Soul Portraits and spiritual guidance sessions, I was also working full-time at an escape room. I enjoyed the job, but I was also looking to escape it—longing to pursue my passions more fully.

Around that time, I came across a belief shared by a spiritual teacher on TikTok: that what excites you the most is actually your purpose—and when you’re aligned with your purpose, you’ll be divinely supported in following that excitement. This idea resonated deeply with me, but I had to ask myself: Was I really willing to follow my excitement and become a full-time artist while diving deeper into spiritual education? Read more>>

Angel Ludwig

I moved alone to Costa Rica one year ago. As 46 year old, divorced mother of 4 adult children, I decided I only had one life… it was now or never.

Risk is different for everyone, defined by fear and how we handle it.I decided I was no longer going to allow fear to define me or my choices.

My work allows me flexibility of location as my clients are in multiple timezones and countries, so travel has been a frequent part of my life. As a people strategist and high-performance consultant, I interact with those with a high tolerance for risk, an impervious level to handle fear, and often, a desire for high-stakes situations. Read more>>

Aaliyah Armstrong

The greatest risk I’ve taken in my nursing journey was relocating to Dallas, Texas from my hometown of Baton Rouge, Louisiana—a place where my support system was strong and familiar. I graduated with my Bachelor of Science in Nursing from Southern University A&M College in May 2018, and just a year later, I made the bold decision to move to Dallas with little to no family nearby. It was a leap of faith into the unknown, but I knew it was necessary for my personal and professional growth. Read more>>

Tia Maniscalchi

I believe a huge reason I was able to become a business owner at such a young age was that I was not afraid to take risks and always bet on myself! I became a mom with my first daughter at 22, went to hair school when she was 9 months old, and then decided to stay home with her while my now husband worked on getting his plumbing license. I decided to go back to work on a very limited schedule at a small salon to get my groove in the hair industry-I learned a lot there, and once COVID hit and the whole world was shut down, it really made me think. Read more>>

Vava Venezia Dellert

Some people take a risk once in a while — a big move, a job, a leap.
For me, risk has always been part of my blood. It’s how I survive. It’s how I feel alive.

The first real risk I took was when I was a child. I was different from everyone in my family — too serious, too sensitive, too aware. I decided to become a vegetarian at ten, back when that made you a weirdo. I used to carry vitamins in my pocket when others carried candy. I exercised like a soldier, even as a little girl. My body was already screaming for a different kind of life. Read more>>

Dani Barker

didn’t grow up in music, and I wasn’t raised on stages. In fact, I was halfway through my nursing degree when I made one of the most pivotal decisions of my life: I walked away from a stable career path and moved to Portland to pursue music—something I had never formally studied or performed before. Read more>>

Jennifer Zimmermann

My mother was a true entrepreneur, a spirit she inherited from her own family. She came to this country from the Dominican Republic at the age of 16. Her own mother, my grandmother, was a school teacher, and my grandfather was an entrepreneur as well. My mother later opened her first business, a children’s boutique, when I was in third grade. By the time I was in sixth grade, she’d had two businesses that failed, but instead of giving up, she decided to pivot into an industry she knew nothing about: motion picture camera houses. Read more>>

Lyn Belisle

One of the biggest risks I ever took came when most people in my field were thinking about retiring. I’d spent 35 years teaching high school art, mostly to kids with learning challenges. It was deeply meaningful work—these students learned to express themselves through art when words didn’t come easily. I loved it and thought I’d finish out my career there. Read more>>

Sharon Macey

I’ve taken two big risks in my life. The first? Moving to New York City straight out of college to break into advertising. I visited NYC for the very first time during spring break of my senior year at the University of Texas at Austin with the Advertising Club. The moment I stepped off the plane—back when you walked down a staircase onto the tarmac—I saw the skyline and knew I was coming back. Read more>>

Laurie Oakes

For me, starting this entire business was a risk.

It was the middle of Covid. The world was upside down. My career as a professional chef had come to a complete halt. My mom’s health was rapidly declining. And I was walking away from a 5.5-year relationship that I had poured so much of myself into. It seemed like the worst possible time to make a big move. Read more>>

Emily Hollingshed

I grew up with a good back bone & parents that pushed me. I graduated Highschool, and went straight to work as a CNA at a big hospital in Tulsa. I started doing shows, and more and more and decided I was going to risk it all, and my future by going full time as a musician. Since then- the best, but scariest decision I ever could have made for myself, it has been a roller coaster of emotions, highs and lows in this business, but I couldn’t be more grateful and hopeful for what the future has to hold. Read more>>

Genevieve Love Lake

By the age of 40, I had settled into a successful realestate career (after multiple sort of successful previous careers), married an amazing partner and found myself back in Miami after 8 years of living in London and a few in NYC. All in all, things were what my younger self would have described as ” pretty darn good”, but for some reason I was constantly having issues with anxiety. My gut knew before I did that I wasn’t where I was supposed to be. Covid forced me to take a pause and reflect and thats exactly what I did. I also happened to have just finished renovating our house, which to my surprise turned out great and I really enjoyed the process. Fast forward to Covid calming and life re-starting and I just could not bring myself to get excited about the world I had taken a break from. Read more>>

Dante Fleming

Despite my dream is being in and making films, my personal risk for me was directing and editing my first music video. I didn’t have the knowledge like I do now compared to before. I didn’t know anything about camera settings or lighting. I knew how to edit, but didn’t know how to use effects. I was afraid because of my lack of resources and knowledge on a laptop and camera that I JUST bought but people liked my b- roll videography that I recorded off my phone. B- rolls and music videos are 2 different things. A friend of mine thought I could make a music video. Read more>>