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.

Luke Bernard

In 2010, my life took a major turn as the conception of my first daughter led to a 2000 mile move across country. My personal goals and intentions got rerouted and my life turned a completely new chapter. Read more>>

Joseph Miller

I have always been told growing up to turn my passion into a profitable business structure. I love creativity, and photography and videography just happen to be the arena it thrives in. Read more>>

Laurie Pace

Many people are not risk takers when it comes to ‘self-expression’ with painting, writing, photography or even with music. Read more>>

Morgan Groff

The biggest risk I’ve taken as a business owner is actually a fresh one. For the last two years, we’ve been working out of an 800 square foot studio. Read more>>

Sebastian Olaya

I’m a pivotal moment in my musical life right now. I’ve spent several years working on diverse projects with people, mainly producing tracks or mixing records that have already been made. Read more>>

Sand Symes

My journey into integrating earth-based and psychedelic medicines into my practice emerged from a profound personal concern. Read more>>

Adam Wise

Without taking a risk, you won’t experience discovery. It rips open the box you’ve been contained in. It builds a new story. Read more>>

Kylie Koscoe

My business story is an interesting one, as I started as an instructor with Mad Science before I became an owner. The previous owner was looking to sell the business, and I reluctantly took it over from her. Read more>>

Nikii Duke

The biggest risk I’ve taken is betting on myself. I’ve given up a regular 9-5 job to chase after my dream of professional wrestling. Read more>>

Faith Vue

The biggest risk I’ve taken thus far in life has been creating and executing my business from an idea, side hustle, & now my full time career. Read more>>

Charles Grayson

Being an independent artist is all about taking a risk. You never known what song will hit, connect with people. The payoff takes an extremely long to happen. Read more>>

Enrico Napoletano

Yes, of course! I was working at a large multinational company, it was a stage in my life where I absolutely had to become independent, and for that, I needed economic stability. Read more>>

Mona Abow

A Single Mother’s Quest for Financial Freedom I came to Canada as a refugee, and I left school to be a stay-at-home mom, but when I got divorced, I became the sole financial provider for my three kids. Read more>>

Zakkiyah Hutchinson

During the lockdown in 2020, which was a tough time for the world, I decided to explore some hobbies to earn some extra cash. Read more>>

Amy McCoy

When I first started illustrating and surface pattern design and didn’t want to put my work (and myself!) out there, my husband would say, “No one knows what you’re doing here in the barn in your back yard. Read more>>  

Xiomara Gonzalez

Life is all about taking risks. I firmly believe that if you’re not taking risks, then you won’t grow in any aspect. Back in early 2022, when I was an esthetician, I realized I didn’t want to do that for the rest of my life, and I wouldn’t be fulfilled if I wasn’t able to tap into my creative side. Read more>>

Shannon D. Bushnell

When I was 28 years old I made a flying leap of faith and bought my first home. I had just started out on my own in my career., had next to no resources and yet I possessed a tenacious desire to own real estate. Read more>>

Lara Salyer

I was shocked to discover myself struggling with burnout 15 years into my career as a rural family medicine physician. To alleviate this heartbreak of feeling trapped in a lackluster career, Read more>>

Deni Baker

Sometimes taking a risk can give the biggest reward of all! Don’t live in fear. Be bold. Read more>>

Justin Douglas

Quacking my 9-5 in order to achieve my goals as a professional makeup artist and influencer Read more>>

Miranda Plum

Over the last decade I have immersed in the artworld, both as a visual artist and performing artist. As a visual artist I painted and exhibited around Australia then expanded in large-scale murals, Read more>>

Hannah Jiao

Taking the risk to transition from journalism to product design led me to my current life. While journalism had been my comfort zone for years, Read more>>

Tony Thomas

Taking a Risk Read more>>

Charla Anthony

• As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that, can you take a minute to introduce yourself and give our readers some of your background and context? Read more>>

Vivian Orozco

I think the biggest risk I ever took was diving into my creative dreams. For a long time, I enjoyed making art, but I always viewed it as a hobby- an accessory to the societally defined “normal” life I was supposed to have. Read more>>

Hunter Turner

From state of the art sound systems, professional software to expensive lighting and all the way down to each cord this line of work ain’t cheap & starting GCPP was nothing short of a big financial risk. Read more>>

Carol Deveney

I was working in a dream job just outside London when I got a phone call that changed the trajectory of my life. Was I interested in a role in Toronto? Quite frankly I wasn’t. Read more>>

Kristy Begin-Patterson

The biggest risk I took was in June 2021, when I decided to leave my high-level corporate career at Apple. After spending nearly 15 years with the company Read more>>

Jade Farhat

Growing up, I was captivated by YouTube. I loved the idea of creating makeup, clothing, and lifestyle videos to share with the world. Read more>>

Dierra Lake

I like to think I’m a risk taker, but honestly, I’m a calculated risk kind of girl. In the creative space though, few things seem to be calculated but more so passionate. Read more>>

Evan Steger

My entire career has been a giant risk. First off my business is a luxury to most people and not a necessity. Metal polishing isn’t something anyone has to do. Read more>>

Dorothy Dillingham Blue

While I’ve continued to appear on camera over the years, I’ve spent most of the past 15 years on the creative team side of theatre, appearing onstage only when personally asked. Read more>>

David Habben

At multiple points in my career, I’ve had the opportunity to jump out of a comfortable situation into something more challenging or even terrifying. Read more>>

Lena Agnello

I feel like the biggest risk I had ever taken within my photography career was accepting an offer to photograph events from the Robert DeNiro Tribeca Film Festival. Read more>>

Amy Elizabeth

If you would have told me 5 years ago that I’d be trying to make a living as an artist and mentor, I am not totally sure I would have believed you. Read more>>

Laura Peterson

As artists – everything we do is a risk. When you make something and put it into the world to be seen or shared you are going to be judged. Sometimes that’s ok. Read more>>

Lina Shatara

Entreprenueralship is all about taking risks and believing in yourself. If I didn’t take a risk to be a full time creative 7 years ago I would never have created endless opportunities for myself or others. Read more>>