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.

John Watkis

The biggest risk I took happened in 1999. At the time, I was traveling the world as a professional speaker and had just released my first book, “Don’t Bite the Hand That Feeds You – How to Avoid Mistakes That Cost You Customers and Credibility.” My book was in major bookstores across Canada, I was appearing on television as a subject-matter expert, and I was being booked for speaking engagements with speakers bureaus. Life was good. Read more>>

Sara Linden

My first career was launched out of my degree in biomedical engineering. My second career was launched out of doodling my way through a business planning course. I guess I would put that in the category of risk taking. I thrive when I’m out of my comfort zone. I love schmoozing (the yiddish version of working the room) and I have learned to trust the process. The journey may be unpredictable at times and, as I like to say to my Mahjong learners to “stay the course” and the rewards (and tiles) will appear. Read more>>

Marsha Vanwynsberghe

I spent 27 years as a Registered Kinesiologist, working with clients in physical rehabilitation from their injuries. During those years, I worked as an employee, consultant, self-employed, and brick-and-mortar business owner. I have seen all sides of the business and taken many risks. I believe that the lessons we walk through set us up for the following stages of our lives. Read more>>

Heather Goodrich

Risk is a delicious subject. It can be the actual danger, the threat of flukes, or even whiffs of danger from the sidelines. In a writer’s world, I often hear about risk in terms of failure. Failing to get published at a certain place, not getting the award or residency, or getting rejected from a job. Failing at something important to you sucks and doesn’t feel good. I get it…I mean, who likes that feeling?  Read more>>

Billy Sullivan

A recent risk that I took was taking a 6 week long cross country trip across the United States on shoestring budget ($1700) to busk in different cities/towns and explore the country. As a 20 year old musician pretty early in my career and limited in my travel/life experience I thought it might be a really cool opportunity to try out. I took my 2003 Toyota forerunner as my vehicle and home, took the seats out of the back, put a mattress in for sleeping, and I got myself a planet fitness membership for the showers. Read more>>

Cécile Roberfroid

As an abstract intuitive oil painter, each time I approach the canvas, I embrace the inherent risks of the creative process. My process is intensely personal, with emotions and instincts guiding each bold, uncertain stroke. I start with a loosely chosen palette, but it’s the willingness to abandon control that truly shapes my work. I take deliberate risks—letting go of elements I’ve grown attached to, covering up what feels safe, and challenging myself to break free from the familiar. These risks are not just part of my process; they are the driving force behind my art, pushing me to explore uncharted territories of color, form, and expression. Through this fearless experimentation, my work continually evolves, reflecting the courage to step into the unknown with every painting. Read more>>

Jessi Vultaggio

My career has revolved around taking risks to build a non-traditional career. After a year of my undergraduate studies in Creative Arts Therapy at Endicott College, I risked transferring schools and majors to pursue Illustration after being inspired by a visiting speaker and illustrator, Craig Frazier. Taking this leap in my education enriched my eye for design, composition, color theory, Photoshop, and the creative process. My risk and hard work rewarded me with a Bachelor of Fine Arts from the Savannah College of Art and Design in 2019. This choice has strongly impacted my knowledge for my current business and was the driver for everything I’ve done in my creative career. Read more>>

Tara O’sullivan Dye

After eight years in the mental health industry, I decided to step away in favor of uncharted waters. I would like to note that what follows is my personal account and is not a generalization for all clinicians. As a Licensed Professional Counselor, I had the privilege of supporting people in some of their most vulnerable moments. The therapeutic alliance is a sacred connection that I hold with reverence. I loved the art of therapy. Due to several unfortunate factors such as inadequate compensation, insurance debacles, and untenable productivity standards- I needed to make a change. The compassion fatigue was too much. Read more>>

Maddison Keiver

I am always taking risks with my music, and doing things that definitely feel “outside of the box” Back in March after recording 3 new songs (with producer Ian Docherty) in Toronto, I decided to go to New York City for the first time, alone. I didn’t know anyone there really aside from a few friends on social media, and some music connections that I had been given. I took the risk and (as I say in my song “Dont Say No”) I took a chance on myself. It really paid off, and even though there were some really scary moments there, it was one of the best things I’ve ever done. I ended up at the same party as Joan Baez and Maggie Rogers. It taught me a lot about how to carry myself and hold my own, something I’ve been doing this whole time, but now I have even more tools. Read more>>

Michelle El Khoury

For more than 20 years, I had built a stable and successful career first in healthcare and then the pharmaceutical industry. I was proud of the progress I made, climbing the corporate ladder and earning a six-figure salary with annual bonuses. From the outside, it seemed like I had it all—financial security, recognition, and a thriving career. But what most people didn’t see was the toll it was taking on my mental health and the constant internal battle I was fighting to keep it all together. Read more>>

Ann Johnston

Being an artist is all about being willing to take risks. Every piece requires choices and once I make them, I can only go forward. I don’t know what the outcome will be until I decide the piece is finished, and then I have to just let other people decide what they think. Every quilt I make has a different creation story, and a different measure of success, depending on who is measuring. The risk to me is distractions from the art world that might make me afraid to create in my own voice. So far, for over 40 years, I have mostly been able to avoid them. Read more>>

Ashley Scott

I have been in this industry for about 12 years now. For the first 10 years I worked and paid my dues in a medical clinic where I got my start as a medical assistant specializing in post operative lymphatic drainage massages for a plastic surgeon in Los Angeles, CA. I later went back to school and received my estheticians license. Flash forward to June 2020, I became a mother, giving birth in the thick of the pandemic. When my daughter was 1.5 yrs old, I was a single mother, however at that time my daughters father was helping me financially with her preschools tuition, $2,000.00 per month. Read more>>

Jose Diaz

Hello my name is Jose an at a young age i had to take a risk to change my life for my goals and where i want to be in my future of success with art. Taking the risk by asking gilbert high to be apart of their project, which opened many doors and gave me this great opportunity to gain knowledge and experience. Read more>>

Miriam Home

In my previous career as a project manager at in-house advertising agencies in the corporate world, I often sought fulfillment outside of work by volunteering. I found deep meaning in roles such as a hospice volunteer, a mentor for at-risk youth, and a liaison for athletes fundraising for the Leukemia and Lymphoma Society. The joy I experienced through volunteering inspired me to pursue a career that aligned with my passion for helping others. Read more>>

Maria Perryman

In 2019 I was diagnosed with breast cancer. I was given the protocol which I thought was too harsh. Especially since it was detected early. The doctor wanted to schedule my surgery right away but I was due to do missions work in Zambia Africa. I was scheduled to board my flight in four days. I was not going to cancel that trip. The trip was for 14 days. God prompted me to wait. Well, I thought the wait was until I got back from my missions trip. But the wait was longer than that! Read more>>

Sasha Aitken

Taking the leap to bet on yourself without a safety net is the biggest risk I’ve ever taken, and it’s exhilarating! Growing up, I watched my dad thrive as an entrepreneur, and I was captivated by the freedom he created for our family. It planted a seed in me, a desire to one day carve out that same independence and give my kids a childhood filled with the same kind of magic. Read more>>

Diego Tirigall

In the whirlwind world of a multimillion-dollar company, boosted overnight by investment funds, I reached a critical juncture. Suddenly, the company’s direction shifted dramatically, forcing me to confront an existential choice. At 40, with a robust career and the option to join any leading company in the industry, I found myself facing the most challenging decision of my life: stay in the safe and familiar world of art direction or dive headfirst into my latent passion for art. Read more>>

Ryan Stubbs

One significant risk I took was the decision to expand K9 Clubhouse from Canada to the USA. This was a big, life-changing move for my business. The backstory begins with my journey in dog rescue and training, which started around 18 years ago when I began rescuing pit bulls from dog fighting rings in Alberta. Over the years, I transitioned from a career in the oil field to become a full-time dog trainer, specializing in dogs with behavioral issues, particularly aggression. Read more>>

Alan Donovan

In 2015 I found myself in the mists of a custody battle to be a part of my sons life. I hired a lawyer and went to court only to find out that in the family court fathers have little to no rights. I fired my lawyer taught myself family law and went on represent myself twice in family court ultimately winning full custody of my son. When people found out that I was teaching myself family law they thought I was absolutely crazy and there was no way I could take on a licensed lawyer and actually win. Everyone thought for sure I was going to lose not only my court case but my rights to be in my sons life. I’ve since passed what i learned on down to other fathers who are in the same situation I was once in. I’ve worked with thousands of fathers around the world over the last almost decade of advocacy. Read more>>

Justin Schnapp

My name is Justin schnapp I come from a background of poverty in and out of homelessness as long as I can remember. I started life at the bottom , made some mistakes and winded up in prison. I dug my self in a deeper hole than I was. I did my time formulated a plan to build my influence and worked hard to get back to square 1. I have been a musician and artist all my life music dance and art an all around artist. I worked in the sneaker/clothing resale industry and acquired a decent foundation of capital and i decided to get involved in the creative space adound me by creating a creative HUB , virva is more than a studio its a third place for creators ive brought thousands of people to downtown norfolk who have never been just to experience what im building .  Read more>>

Kristopher Fernandez

I decided to take a risk betting on myself and that these vending machine business would work, down to my last dollar and once I decided to go forth full time into my business boom and now we are set to expand Read more>>

Superman Mccoy

Recently, I took a risk on myself leaving everything that was my safety and comfort zone. I deconstructed my life going through everything as I was getting rid of everything and moving out of Austin. Finally taking the leap to travel and share my life fully with others while advocating for Trans Rights as well as LGBTQIA+ Rights standing up against injustice as well as moving forward and letting go. After heartbreak and a long legal battle with the LA Sheriff’s Deputy’s Department overcoming and surviving a hate crime in 2016 then being attacked in 2020 from LA Sheriff’s Deputies, I found myself again having a battle of what I am wanting to pursue in life. Read more>>

Leslie Perez

One of the biggest risks I have take is leaving my stable 6 figure income as a Sales Account Manager to go 100% in with my Fitness Online Training Business. It has been almost a year and I am almost matching my income at the corporate job. Life is too short to not be doing something you love. Success is not defined by how much money you make but how happy you are with what you do on a day to day basis, Read more>>

Sarah Mccallum

I took a massive risk three years ago and began investing in myself through a healing arts program that was priced outside of my comfort zone. I was a mother to young children and had all of the reasons as to why this money should go towards other obligations or commitments beyond myself. But I had the desire to take a risk and jump in, not knowing where I would land. It was terrifying and yet I’ve grown more in the last three years than ever before. As an entrepreneur I have learned so much around how to fully embody my gifts and embrace my process. Taking risks is simply part of the journey of entrepreneurship. I am so grateful to have found the strength and courage to go full steam ahead for that decision completely shifted the trajectory of my life for the better! Read more>>

Karrie Leblanc & Amanda Reynolds

The biggest risk we’ve taken was starting our business, MPower Marketing Group. It was a leap of faith, stepping into something we felt strongly that God called us to do. As planners—and maybe a bit of control freaks—leaving the security of our jobs for the unknown was daunting. But we knew this was the path we were meant to take. The fear was real, but so was our determination. It’s been an incredible journey, filled with challenges and growth, and we’re grateful for the opportunity to follow our calling. Read more>>

Iyanna Pierre-louis

Every day presents a new gamble, an unseen dance with the unknown orchestrated by God. With each sunrise, we face 24 hours of unforeseeable moments. Despite our best hopes and expectations, we cannot fully predict or control the outcome of our day. This realization transformed my understanding of risk. It’s not confined to monumental leaps; it’s also in the small details of our daily lives. I’ve learned to redefine risk, seeing it not as a looming threat tied to fear, but as a gateway to infinite possibilities, all within God’s grand design. This shift in perspective came from embracing the notion that even small decisions can significantly alter our paths. Armed with this new understanding, I now welcome risks, recognizing them as opportunities for exponential personal growth. The true test of our choices’ outcomes only comes from taking action toward our goals. Read more>>

Jessica Feuerbach

Ever since I was a young competitive gymnast, I have been somewhat of a risk taker. However, my biggest risk to date is purchasing Rocky Mountain chocolate factory in old Sacramento. I had never owned or ran a business prior to owning Rocky Mountain, but when I saw it listed for sale, my heart skipped a beat. One day, I happen to be browsing Biz by cell when I saw the cutest picture of a confectionery store. The more I inquired about it I ended up realizing what store it was. It was Rocky Mountain chocolate factory! I used to go to this particular store as a child and it brought back all the feels. I immediately text my husband and randomly asked if we could buy the candy store in Sacramento. He was extremely confused, but trusted my instinct and agreed that we could proceed. Little chocolate factory, but my gut was telling me that this felt right. I have never looked back since.  Read more>>

Jennifer Axcell

Being an artist requires bravery. It can be terrifying to bare our souls through our work and launch those creative expressions into the world, opening us up to critique and financial failure (the term “starving artist” exists for a reason). Will it be “good enough?” What if nobody buys it? Will I ever be able to support myself through my art? These questions plague most aspiring artists, which is why so many creatives never pursue their talents beyond hobbies; it’s risky. Read more>>

Jetson Slayter

The biggest risk I’ve taken was becoming a content creator. In the beginning stages of my career I had a lot of people tell me that I needed to be realistic and pursue a “regular job”. In my mind being a content creator was a regular job. I’ve been making content ever since I was a kid. Making little videos as a young 6th grader with my little sister, Anyssa, and editing them as well. Being behind the camera and In front of it has always felt so normal and natural to me so it just made sense for me to pursue this as a career despite what anyone thought. Read more>>

Sharon Short

About ten years into my publishing journey as a novelist, I found myself without agent representation, an editor, or a book contract. I’d enjoyed the publication of nine traditional mysteries, in two different series, all with one of the “big 5” publishers, all as paperback originals. But almost all of the authors who shared the imprint for my second mystery series were let go–en masse. My then-agent suggested I write a nonfiction book about retirement, although I was nowhere close to retirement and did not have a nonfiction platform. (I’ve wondered since if this was just a convoluted way of letting me go.) I parted ways with that agent, and then wondered… what now? The editor for my second mystery series had also left publishing. Read more>>

Alejandro Sanchez-ochoa

Being raised by Immigrant parents feels like the stakes were always higher leaving little to no room for error. That being said I knew that I was going to have to pursue something of great notoriety. In 2017 I Graduated with my undergrad of Food Science and Nutrition which at the time I wanted to pursue Food Chemistry while I also had just started taking photography more seriously. Shortly after graduation I moved over to Bellevue and started working full-time at Microsoft where I was Admin and eventually became an optometrist tech. Read more>>

Lauren Juarez

My whole life has been about taking risks. When I was younger I risked having a typical childhood in order to make it to my hours of dance class. In high school I took a big risk and got married at 18. I took a risk when I started posting on social media with a dream to work with brands one day. When I was 20 I moved across the country to an apartment sight unseen and risked not liking the area. And when I was divorced at age 21, I took the biggest risk sharing that information publicly on my social pages. I wanted to share my experience and what I was going through, however, I had no idea how people would respond. Read more>>

Leslie Hoyt

As a photographer, I was trained to get an image right in camera. My focus and exposure should be spot on. If I was photographing a flower, for instance, it should be sharp front to back. It needed to be perfect. So then the pandemic comes along, and a friend suggests I take an online class from Martin Osner, a South African photographer who uses a lot of experimental techniques to create fine art with photography. This was SO far out of my comfort zone! I took a perfectly good photograph and used various methods, including using hand sanitizer, to transfer it to watercolor paper. Of course it was impossible to get it to transfer perfectly.  Read more>>

Anja Carron

High-performance consultancies are at the heart Risks and balance are among the most critical topics in our times. As we venture into uncharted territories, much like the pioneers of old, the key to success lies in maintaining balance and relying on our inner compass to guide us through our journey. Risks are not fixed entities; they are relative and shaped by our culture, societal background, environment, education, level of capabilities, and our understanding of our limits within a given context. Read more>>