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.
Alyceson-Grace Eke
I’m in the middle of the biggest risk I’ve ever taken, actually. Come May 2026, I will be self-employed for two full years. It’s scary when it’s not what you initially planned. The transition came from being unexpectedly laid off from my corporate job at a private community bank in 2024. Read More>>
Davis Kurepa-Peers
With the current state of the job market, I was in a rare circumstance where following my passion was just as risky as having a corporate gig–so why not go for it? Read More>>
Mikey Oshai
In May 2022 I shot Love Damini, Burna Boy’s album cover. That project changed something in me. It confirmed the level I was capable of operating at and made me hungry for more. A few months later in August I came to LA on holiday. No plan, no agenda, just a trip. But something clicked while I was here. Read More>>
Lisa DeLugo
One of the biggest risks I’ve taken was using my voice in a way that could actually expose me. Starting Mom Is My Emergency Contact Podcast wasn’t just launching a podcast. It was stepping into a space where I knew I’d be seen and judged for saying the things most women only say in private. The backstory matters. I’m a single mom. Read More>>
Pamela Joy Trow
The greatest risks I’ve taken in my life have come through physical moves. Over the years, I’ve moved to seven different cities in six different states, and each move required courage, reinvention, and a willingness to start over. My most recent move, in July 2025, was one of the hardest and most meaningful risks I’ve ever taken. Read More>>
Jess Novak
My entire adult life has been one risk after another. I was very brave as a child, but extremely reserved as a teen. When I was young, I sang all the time, led cheerleaders even though I was never on the cheer squad, performed musicals for my mom and was generally fearless. Read More>>
Monica Martin
My journey into this work really began in the middle of real life—not in a studio, but in the in-between moments of raising a family. About fifteen years ago, I was newly divorced, and I made the decision to take a risk on myself. Read More>>
Marty Cynclaire
One of the biggest risks I ever took was moving out of my parents’ house with only $1,000 to my name. No real safety net, no backup plan—just belief that I had to figure it out. At the time, I was working at Kmart, just getting by. Rent was due every month, whether I was ready or not. Read More>>
Vivian Ah
I didn’t start out planning to do astrology professionally. I actually started with tarot. When I launched my channel in 2019, no one was watching at first. Then one night, it suddenly picked up. Within a few months, I had over a thousand subscribers, and people started reaching out for personal readings. Read More>>
Mari Hashimoto
I think the biggest risks I took, is to be myself without fearing judgement from others and not following mainstream advice. This came in two major waves in my life. The first was leaving the corporate world after back-to-back burnouts and I went into building a career as a psychic and Akashic Records reader. Read More>>
Brandon Doherty 
Taking the risk to build DORTI was easily one of the biggest leaps of faith I have ever taken. At the time, I was working a solid job in real estate as a leasing manager. It was stable, reliable, and the kind of job many people would be grateful to have. But every morning I sat at that desk, I felt pulled toward something else. Read More>>
LIIA KAMKADZE
One of the biggest risks I’ve ever taken was coming to the United States. I had dreamed about coming to the U.S. since childhood. I grew up watching American movies, loving musicals, listening to American music, and I was completely immersed in American culture. I first started talking about coming to the U.S. when I was 15. Read More>>
Tajia Lagomarsino
⸻ The biggest risk I’ve ever taken hasn’t been in my career, finances, or even moving across places—it’s been in love. Love with family, friends, and partners has required a level of vulnerability that nothing else in my life has demanded. I grew up learning how to be strong, independent, and self-sufficient. Read More>>
Ryan Rumpca
A year ago I took the biggest risk of my life. I left a career that I had worked very hard in, and of which many people would see as ‘successful’. I spent 7.5 years working my way up the corporate ladder as an engineer and eventually a project manager in the aerospace industry. Read More>>
Noelle Jones Aladesuyi
Risk-taking isn’t a one-time thing for me. It’s the baseline. If I had to name the most life-changing risk I’ve taken, it’s becoming an entrepreneur and, more specifically, when I decided to fully step into it. It was October 2020. We’d been in quarantine for months. The world felt paused, but at the same time, everything felt urgent. Read More>>
Taja Jayy
One of the biggest risks I ever took, I honestly didn’t even realize how risky it was until it had already happened. I met a fellow musician online (Instagram) and he asked me to fly out to Kansas City to film a music video to a song we had worked on earlier in the year. Read More>>
Dorrett White
You have to be willing to be seen! Just after the pandemic and two years of not booking a single acting gig, I was working a desk job to support my family and I really struggled with depression, low self worth and crumbling confidence. My identity as a performer was so tied to what project I was working on. Read More>>
Melissa Zehner
Starting my business was by far the biggest risk I’ve ever taken. I’d love to tell you that it was calculated and thoughtful, that I spent months planning and preparing — but I didn’t. I leaped, without any kind of plan or net. My last employed job was the most toxic employment situation I’ve ever been in. Read More>>
Emily Bargeron
The biggest risk I’ve taken was choosing to shift my focus away from a business I had spent over a decade building—my fashion brand, Mamie Ruth—to fully invest in something entirely new. Mamie Ruth was my foundation. It gave me international recognition, took me on countless music festival tours across the country, and sustained me for years. Read More>>
Tamela Carter
A little back story about how my vision went from a ‘what if’ I could build a business doing something I love that I could build from my own home into becoming a woman-owned business that is still growing 26 years later? I have always been a creative person that loved the art of sewing and creating beautiful things with my sewing skills. Read More>>
Jasmine Keen
I took a gigantic risk starting my photography business. I was a new mom, new to adulthood and I hadn’t touched a camera in almost 10 years. One Christmas I asked for a camera…. I got it. A beginner Canon Rebel, that baby got me to where I am now. Read More>>
Caroline Jordan
I have been a certified health and fitness coach for over 25 years. I had established my business in San Francisco where I was very successful for 10 years with in person work teaching classes, consulting companies / corporate wellness, and working as an ambassador for large fitness brands. However it was a big dream of mine to move to San Diego. Read More>>
Tierra O’Neal
One of the biggest risks I’ve taken was quitting my 9–5 job without really knowing what was going to happen next. At the time, I had what people would call “stability.” I had a steady paycheck, a routine, and something that made sense on paper. But I wasn’t happy. I knew I was meant to be doing something more creative. Read More>>
Emily Barth
There’s a version of me that almost didn’t go to Paris. The version that overthought the timing. The money. Leaving my babies. Whether I was “ready” to stand in rooms I used to only dream about. But there was another voice, quieter, but stronger. The one that said: this is what you’ve been praying for. So I took the risk. Read More>>
Cecelia Steidinger
I started my business in July of 2013 in Billings, Montana. My husband and I (and our puppy!) had just moved across the country from Indianapolis, Indiana to a brand new state for his job! I was in (unhappily) in grad school and (happily) nannying on the side. Read More>>
Jori O’Neale
I remember sitting inside a CarMax dealership on a warm evening, holding a folder that represented a decision I never thought I’d have to make. Read More>>