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. 

Craig and Tanzania Cooper

One of the biggest risks we recently took was launching the first-ever UpliftUS Collective Mental Wellness Showcase for our DMV chapter. On paper, it may have looked like just another community event. But behind the scenes, it represented a leap of faith. Leading up to the showcase, both of us were navigating significant health challenges. Read More>>

Caroline Tullis

The biggest decision that, for me, felt risking was moving from my small hometown of Cuyahoga Falls to the big city of Cleveland. It was the first time, aside from college, I moved somewhere a bit more further away from where I grew up. Read More>>

Tylia L. Flores

One of the biggest risks I have ever taken happened in my late twenties when I made the decision to step away from being known only as a disability advocate and writer and begin pursuing ministry and Christian writing. For years, people knew me as the founder of Stomping On CP. My identity was wrapped up in disability advocacy. Read More>>

Aje Soberekon

Picture this: it’s 2020, COVID is at its peak. I was in the final year of my undergraduate program studying Architecture and Theater Design & Production. Work was scarce, uncertainty was everywhere, and like many people, I was stressed about what came next. Read More>>

Michael Jacques

Life is all about risk… It’s part of the game, and yet most of us simply stay in a ‘cozy’ place, even though at times it’s not the best place for us in the long run. I’ve had to overcome many obstacles in my life. Some unexpected, some self-imposed. Read More>>

Savaun Young

Being a “Artist” you have to make & take a lot of risk, from being on the road taking time away from your family & kids, everything that comes with it:Studio time, proper promotion & marketing, the shows, interviews, podcasts, building a brand you have to be willing to loss time from certain things & put your focus on what matters most to make sure your people & family will be set for life! The sacrifice to be better! The results are good long as you put your mind to it & actually do it! Read More>>

Kehinde Thomas

One of the biggest risks I ever took was leaving the comfort of a traditional career path to pursue entrepreneurship and financial education. I was born in Nigeria and lost my father at a young age. Like many immigrants, I came to America chasing opportunity. Read More>>

Desarae Dee

For me, the biggest risk wasn’t a single decision; it was choosing to keep investing in my music and business year after year, even when there were no guarantees. I started playing piano at six years old and eventually built a career as an artist, composer, producer, educator, and entrepreneur. Read More>>

Jatoyia Armour

One of the biggest risks I’ve taken was deciding to publicly build businesses and communities around the hardest parts of my personal life instead of hiding them. For a long time, I was the person helping everyone else while quietly carrying my own struggles. Read More>>

Shilpa Cacho

From the very beginning of my business, I’ve been taking major risks and betting on myself and I wouldn’t have it any other way. When I first started, I had zero dollars to my name. I had spent 10 months as a stay-at-home mom, and while I was grateful, I was miserable. I had lost myself. I felt depressed. Read More>>

Nicolas Fanucci

Here is the biggest risk I have ever taken: becoming my own boss and involving my family in our first restaurant venture in Malibu. Nicolas Eatery was originally scheduled to open in October 2018. However, a month before our launch, the city halted construction due to permit issues. Read More>>

3K5 MILES

I’ve always had an internal calling that there was more to life. After graduating high school, I wasted no time following my internal compass. Through travels with my father during his trucking career and eventually our separation, I found myself in Denver, Colorado, camping in the back of a box truck after making the decision to search for truth. Read More>>

Naseera Mays

After twenty-five years in Human Resources, I made a life-changing decision that would redirect the course of my life. After being accepted into a Master’s program, for Clinical Mental Health Counseling, I decided to step away from my role as a Human Resources Director to focus on my studies. Read More>>

Jordan Queira

Five years ago, I left Toronto and moved to Los Angeles to pursue a career in the arts. Like many artists, I spent those years navigating the challenges that come with trying to build a creative career, and those experiences shaped the way I see the art world today. A year ago, I moved to Las Vegas to work at Ikon Homes Gallery. Read More>>

Donnesha S. McBride

Risk is inherent in every path we choose—and not taking a risk is, in itself, the greatest risk of all. One of the most meaningful risks I’m taking right now doesn’t look dramatic on the outside—but it’s changing everything about how I lead, build, and live. By day, I serve as a Director of Center Operations & Strategic Initiatives while also pursuing my PhD degree. Read More>>

Troy James

After 21 years at Starbucks, I knew what predictable success looked like. I performed at a high level in demanding roles for two decades. But the work I was proudest of was never my job description.Read More>>

Cinzi Lavin

Early in my career as a playwright, I heard the same advice from everyone: Try to win a contest or festival to get noticed, and hope an agent or licensing house would express interest. In the meantime, rely on institutional arts grants. I was also advised to post my scripts on an online play exchange so “people who matter” could browse my work. Read More>>

Jawar VanDyke

The biggest Dream killer in the world, it is caring what people think because that alone will stop you from doing the things you love or chasing a dream because you’re so worried about how you look. According to what other people are saying, and that keeps you in a box and you diminish or sit on your dreams and your gifts and your visions. Read More>>

Kaila Symone

For years, I was living a life that looked successful on paper. I earned my degrees, built a career in federal consulting, worked on high-impact projects, and followed the path that made sense. Growing up in a single-parent household as a first-generation college student, practicality mattered. Creativity was something I loved, but it never felt like something I could build a career around. Read More>>

Young Han

I turned 40 and spent four hours with my financial planner modeling every version of my future. More savings, less savings, retire at 60, retire at 70. Every scenario landed in the same place: a mediocre life now so I could afford a mediocre retirement later. Then hope I die before the money runs out. My planner said this was normal. I called friends. Read More>>

Ciera Latrice

One of the biggest risks I’ve taken was pursuing music as an independent artist. It’s easy to dream about being an artist, but it’s a completely different thing to invest your own money, time, and energy into making it happen with no guarantees. While building Hands Of A Goddess Beauty Bar, I continued recording music, performing, and growing my brand as Ciera Latrice. Read More>>

Shannon Fernado

In January 2023, I approached the Ethiopian Government, alongside local leaders and partners, to negotiate the sharing of an indigenous Ethiopian crop called Enset. Enset is a marvel – drought-tolerant, climate-resilient, nutritious, related to the banana family, and a source of food and income for families, especially women. It’s a staple food for 20 million Ethiopians and buffered communities from famine during the 1980s. Read More>>

Demi Michelle

When I started songwriting, I only focused on pop music, since that’s what I grew up listening to the most. At first, I thought I would always be a pop artist, but then, I fell in love with country and decided to be a multi-genre songwriter. Read More>>

Jared Diaz

How Paniolo was started was a small Hobby that turned into a risky decision. I had been a contractor in construction for years focusing on framing ,drywall,and then Mainly hardwood floors and stone work. Having my brother as a partner we would talk a lot about doing something different (we grew up in the trades). So being from Santa Maria Ca. Read More>>

Bethany Zachman

As a Type A perfectionist, I always had a plan for my life. By the time I was 11 or 12 years old, I knew I wanted to become a marriage and family therapist. I spent years working toward that goal—earning scholarships, taking PSEO classes, and completing my bachelor’s degree in psychology in just two years. Read More>>

Jackie Scharenberg

I am not a risk taker. Let me start there. These days I spend a lot of time posting photos online, talking about my journey as a photographer, and sharing my perspective. And I have gained so much from being willing to share. Read More>>

Kevin Orozco

Life as a cook in Mexico is tough — minimum wage, 12+ hour shifts, six days a week, surrounded by vices, with no real work-life balance and little time for friends or family. The biggest risk I’ve ever taken was immigrating to Canada in search of a place where I could truly live through my passion. Read More>>

Daisy Camarena Yulliana Camarena

Taking the risk to start our own business was one of the biggest decisions we have ever made. Before opening D’Fifth Rose / The Garment Clinic, we had already been working in alterations and tailoring, and we could clearly see that there was a real need in the market. Read More>>

Trevon Hobson

I have been working in the education system for a while, when I was working with a non-profit visiting kids at a local school. The principle at the time saw me working with the kids and asked if I wanted to teach. I was afraid at first because I have been a teachers aid but never lead teacher. Read More>>

kamil hudgins

For a long time, I prioritized stability while keeping my true passion for the beauty industry on the side. I even launched my hair brand, Beauty From Above by Kamil, but I was balancing it all while trying to maintain a safety net. The turning point came when I decided to go all in.Read More>>

Ty Morrell

Taking risk so you can achieve your goals is necessary. Taking risk can be as small as making a phone call or as big as the money and time you put in. Nowadays it’s a risk to believe in yourself knowing that a lot of people may no believe in you. Read More>>

Sara Lynn

Risk I believe is at the essence of the potential of our greatest path ahead. Risk is vulnerable & courageous – this is the path and difference between truly seeing what’s possible and out there for you. Read More>>

Alexxus Carr

The biggest risk I have ever taken was taking a risk on myself. It was quitting my job and moving to Atlanta, GA with just $5,000. Now some may say agree that this is or isn’t enough to start the move, which in 2018 it was a good start, however, it didn’t last long. Read More>>

Thomas C. Keller

For most of my adult life, I followed a fairly traditional path. At age 25, I started a remodeling business specializing in high-end homes and spent the next 40 years building that company. Creativity wasn’t something I thought of as a career. It was simply not on my radar. Then, at age 45, everything changed. Read More>>

Mike Shisler

One of the bigger risks I’ve taken was building my art business around actual lived experiences instead of following a more studio-based career path. I studied architecture, and for a while, I thought my professional life would stay in that world. But I was also always drawing, traveling, biking, and doing my best to document the places around me. Eventually, those things started to merge. Read More>>

Kerri Steele

One of the biggest risks I’ve ever taken was starting a nonprofit after my husband died from cancer. At the time, I had no business background, no nonprofit experience, and honestly no roadmap for what I was doing. Read More>>

Marlene Goldman

Taking a Risk: Betting on Myself in Miami Real Estate One of the biggest risks I ever took was leaving a successful career working with ultra-high-net-worth clients in Miami’s financial district to pursue a career in real estate. What many people don’t know is that my connection to real estate began long before it became my profession. Read More>>

Lia Pualena

I recently just moved across the country by myself, and can definitely say that was one of the biggest risks I have taken in my life thus far. I was born in Southern California, spent some time living in Madison, Wisconsin, and just recently moved from Atlanta, Georgia where I was living for the past 8 years. Read More>>

Justin K. Rivers

I did some acting in high school, but a wise teacher told me not to go into theatre. Of course, I’ve had a day job in theatre admin for over a decade now, so his advice didn’t quite stick. Read More>>

Devon Teeple

One of the biggest risks I’ve ever taken wasn’t in business—it was deciding to believe in myself again. I found myself at a crossroads. On paper, I had built a successful career in leadership and financial services, played professional baseball, and achieved many of the goals I had set for myself. Read More>>

Scott Tilford

Leaving Fortune 500 corporate jobs to start Depot Brewing Company is the biggest professional risk I’ve ever taken. When I started at Procter & Gamble in 2005 I thought it would be my forever path. Even in 2020 if you had asked me, I’d retire from there. Then unfolded a series of events that pulled me toward building something more meaningful. Read More>>

Nova Wallace

The biggest risk I have ever taken in my life was the decision to become Nova Wallace and build my brand. In the beginning, my dream was to become a Human Resources Manager at General Motors. I was on my way. Read More>>

Chassity Arnold

Following the pandemic, I decided to completely change the direction of my business. At the time, I had healthy vending machines. I realized the importance of offering an essential product. So, I got rid of my machines and created VITA-RUB. A pain relief topical inspired by my mother who suffers from chronic pain. Read More>>

Yael VanGruber

One of the biggest risks I took was creating a counseling practice that integrates traditional relationship and marriage counseling with creativity, mindfulness, and holistic approaches to personal growth. While conventional counseling often focuses on communication and behavioral tools, I found that many individuals and couples also needed opportunities for self-expression, reflection, and reconnecting with their authentic selves.Read More>>

Shelly Kentner

One of the biggest risks I’ve ever taken was opening my own restaurant in my late twenties. I had spent years working in the service industry and absolutely fell in love with hospitality — not just the food and drinks, but the feeling of creating a place where people could gather, celebrate, unwind, and feel at home. Read More>>

Jessica Moncrief

Back in 2018, I was working a desk job, and photography and music journalism were just side gigs. I had achieved some goals as a photographer, including being published in Vogue, but during the day I felt completely chained down. Read More>>

Caleb & Madelyn Seeks

A few years ago, we made a decision that did not make much sense on paper. We stepped away from stable routines and started building our lives around long distance trails, storytelling, and making art. Since then we have walked thousands of miles across the United States while documenting the experience through photography, poetry, and writing. Read More>>

Kary Hyunjeong Rho

One of the biggest risks I’ve ever taken wasn’t a single decision—it was choosing to rebuild my life from scratch when there was no guarantee it would work. A few years ago, I found myself at a crossroads. I was raising three children, navigating a difficult life transition, and trying to keep my creative career alive at the same time. Read More>>

Dave Williamson

I think the biggest risk I have taken was deciding to quit my 9 to 5 job and going out freelance on my own. I had been working at a home service company running their marketing department. I was facing a good bit of issues within the company but the biggest was that it was a toxic work environment. Read More>>

Erin Brassard

Taking the leap to start STAND was one of the biggest risks I’ve ever taken. I didn’t have formal education or a clear roadmap for how to build something like it, I just had lived experience and a deep, undeniable feeling that there was a gap in support that needed to be filled. Read More>>

Syah B.

I quit my job in the middle of the Covid-19 pandemic. I know… seemingly foolish. Who quits their job in the middle of great uncertainty? The world was reconciling with social interaction and safety. America was forced to face centuries of racial oppression through the rise of the Black Lives Matter movement. At the time, I was overwhelmed. Read More>>

Amy Roosa

One of the biggest risks I’ve ever taken was starting The Safety Rack. The idea came to me during the tail end of COVID, at a time when life already felt overwhelming. Professionally, I was navigating a major career transition. Read More>>

Areon Jackson

Taking this risk didn’t start with a grand plan it started with a phone call that caught me completely off guard. Read More>>

Cassie Butcher

One of the biggest risks I’ve taken was choosing to build a life centered around healing and wellness before I fully felt “ready” or secure enough to do it. Read More>>

Nick Stubblefield

After graduation from college, I didn’t exactly have a 5-year plan. I’ve always been a bit more of an intuitive type, and often imagined myself trying out big city life. I had grown tired of the limited opportunities where I was living, and up until that point, life had largely been prescribed to me by a school schedule. In 2012, Read More>> 

Nia Thomas

Taking risks, for me, isn’t a single dramatic moment—it’s the baseline of how I operate as an entrepreneur. It’s a daily practice. Every decision I make carries some level of uncertainty, and I’m constantly weighing potential upside against very real constraints—especially cash flow, timing, and capacity. Read more>>

Teresitta Jones

3 years ago my husband passed away which left me as a single mom and widow to 7 children 3 are under 10 3 are grown 1 teenager I didn’t have no money ,no business skills so I started searching for work unfortunately due to childcare I had to pivot into a career of my own through disappointments, grief and side hustles failing I then found my way now 3 years later I’m hosting free credit & consumer restoration seminars , have a caregiver for my kids and much happier now I knew 3 years ago I had to take that risk to push more for a better futureRead More>>

Emerson Geter

 

The biggest risk I’ve taken was choosing to build a system instead of just building a business. Read More>>

 Railey Molinario

One of the biggest risks I’ve ever taken was leaving everything familiar behind to rebuild my life from scratch. Read More>>

Michael Nestor

The gap I kept seeing at J&J was the same one I’d watched stall promising science for years: scientific platforms with real therapeutic potential, and no clear path to get them into drug discovery pipelines. I had built some of the earliest functional screening systems using human brain organoids, watched the technology mature, and kept waiting for someone to build the right company around the drug discovery platforms we were building. Nobody did. So in 2023 I co-founded Autica Bio .Read More>>

Chanel Green

One of the biggest risks I’ve taken is choosing to fully invest in both Morgan State University and Green Goals Beauty Academy at the same time while raising my children and serving my city as a Commissioner for the Baltimore City Community Relations Commission. Most people would look at those responsibilities separately and think they are already overwhelming, but for me, they are all connected.  Read More>>

 David Atkins

In May 2021, I took the biggest risk of my life. Read More>>

 JuliAnne Wright

To some degree, any and every creative venture seems risky. You have to paste your heart and soul to the outside of yourself and hope nobody points and laughs – and that maybe at least one other person hears your song and can identify with it, or dance to it, or – and this is the best – is somehow healed by it. For me, it felt a little risky investing in audio engineering as a side-hustle at the age of 40, after a successful career as a public school music teacher with a consistent paycheck. Read More>>

Shakira Stuart

Firstly, let me start this one by saying that I am naturally very risk averse. I prefer surety, safety, and predictability to a certain extent. I don’t take risks lightly. With that being said, leaving my 9-5 corporate job is the risk that comes to mind immediately. Read More>>

Todd McLaughlin

One of my biggest risks was opening our yoga studio 20 years ago. Read More>>

 Darren Hartford

As a small business owner, I recognize that optimism, problem-solving, and calculated risk-taking are essential traits. Since purchasing Oliver Pluff in 2018, I have often faced a decision point between playing it safe and seizing an opportunity. While planning, forecasting, and seeking counsel from mentors and prayer is essential, ultimately, a timely decision and action are required. Here are two situations where I took a significant risk that proved successful. Read More>>