The Rise of the Side Hustle

The Rise of the Side Hustle Header

FEATURE STORY – Pique Newsmagazine, May 31, 2018

Perhaps you’ve heard the adage that the way to fulfil your purpose is by following your passion. Find your bliss. Do what you love and you’ll never work another day in your life. Unfortunately, people are often left disappointed when they fail to secure a job that lights them up. But let’s face it: dream jobs don’t always pay the bills.

That’s why a growing trend in the business landscape has emerged: side hustles.

In simple terms, a side hustle is a job that brings in extra income and differs from your main employment. And although you might think our little resort town is readily familiar with sideline jobs—after all, the high cost of living here means many are forced into working multiple jobs just to make ends meet—the art of the side hustle runs deeper.

While side hustles provide supplemental income on top of your “real” job, they are not the same as a part-time job, with your employer determining the hours you work and the income you make. A side hustle is free from those constraints, giving you autonomy to decide how much you want to work and how much money you’re likely to earn. The more you hustle, the more opportunity to top up your bank account.

Chris Guillebeau, author of the book, Side Hustle: From Idea to Income in 27 Days, defines it brilliantly: “A side hustle is an asset that works for you.” He calls side hustles “the new job security. More income means more options. More options mean more freedom.”

That analogy should resonate with the adventure-seeking, free-spirited people who came to build a life in Whistler, where side hustles are becoming increasingly popular.

Melanie Timms is a prime example. Over this past winter season, Timms has worked as a server at Christine’s on Blackcomb Mountain while continuing to build a clothing design business she launched three years ago, Beauty and the Bandit. Blending her desire to flex her creativity with a longing for more freedom and travel, it was the ideal job.

Working in the service industry, Timms came across many people juggling multiple jobs due to affordability issues and the seasonality of resort life. Although they can be barriers to building a life here, those two factors actually aligned perfectly with her aspirations for a thriving side hustle. “I’ve had to adopt a mindset of discipline and structure to focus on developing my business amidst the distractions of working in a town that constantly entices with social outings and outdoor adventures,” Timms says. “Now that the seasonal job has wrapped up, I have the freedom to make my annual trip to Bali to work with clothing suppliers there.”

While Timms chose a job with Whistler Blackcomb’s fine dining restaurant because of its decent pay, an unexpected benefit was having a chance to meet people from all over the world, which gave her a chance to tap into business expertise and even potential investors she wouldn’t have had access to otherwise. “Tourists show up in Whistler with a positive attitude and willingness to hear your story,” she says. “My business is built from a deep-seated passion, and others seem to gravitate towards it.” That type of interaction over the winter season has motivated Timms to charge forward with her side hustle and continue to fulfil her passion.

Rise of the Side Hustle


There is something to be said for combining a day job that offers security with the opportunity to fuel your creative fires on the side—but it isn’t always easy. It can mean doing double duty at the risk of disturbing a fine-tuned work-life balance. Whether the sacrifice is worth it is a very personal decision, but according to the Financial Post, more and more people are gravitating towards non-traditional work. According to Statistics Canada, the percentage of workers with multiple jobs has more than doubled in the last 40 years, to 5.3 per cent last year. In 2015, almost 959,000 Canadians worked at least two jobs and of those, over 40 per cent reported working more than 50 hours a week—a difficult schedule to sustain long-term.

Amy Fast knows that challenge full well. At 14 years old, she started working at the family business, Cardinal Concrete. Ten years ago, she joined the company full-time to build a career that she loves, and although she doesn’t plan to leave the role anytime soon, she has a dream to create something that one day will allow her the freedom to work from anywhere in the world. In 2016, she attended the Lighthouse Open Forum Speaker Series that left her believing she could turn that dream into a reality.

Rise of the Side Hustle

At that event, career transition coach Lydia Lee shared her story of kicking the “normal” corporate life to the curb and designing a location-independent life in Bali for herself. She designed her business, aptly named Screw the Cubicle, to guide people as they seek to repurpose their skills to find purposeful, meaningful work outside of the 9-to-5 grind. The talk bubbled up a desire in Fast to explore what it would mean to carve out a side hustle. Soon enough, she had signed up for the next Screw the Cubicle retreat in Bali.

People often think side hustles are hatched from a clearly defined career plan, but that isn’t always the case. Lee claims this sense of uncertainty is actually quite common, and can lead to a certain hesitance to fully lean into a side hustle. Although many want to pursue something outside of their “real” job, they often question who would hire them in an entirely new profession when they don’t yet have the experience built up that clients typically look for.

“We so deeply identify with what we do in our work and it holds us back from trying something else,” Lee says. “A lawyer often doesn’t believe he or she can be anything or make money as anything but a lawyer. My mission is to have people looking inward to find the skills and expertise that they want to build on and put out into the world.”

Fast experienced that uncertainty firsthand when she headed to the Screw the Cubicle retreat. She had considered starting a blog to pull from her love of travel, but had no idea how to monetize it in an already saturated online marketplace. But her time with Lee and 10 other “wannabe” side hustlers helped her discover what was right in front of her the whole time.

Friends constantly praised Fast’s intrepid spirit, and although she didn’t particularly think of herself that way, she admits to having no problem dropping everything for the next adventure—whether it was walking the famed Camino de Santiago trail a couple years back or fulfilling her dream of hiking Kilimanjaro this June.

“You don’t always see what you are already doing, but my time at the retreat led me to recognize what I’m good at and what my friends were always asking me about,” Fast says. “I had already started a Facebook group for friends to connect with other people to go out biking or paddleboarding. Adventure is everywhere and doesn’t have to be a scary thing. That led me to a deeper desire to curate experiences for women to bring adventure into their lives and from there, Amy Goes Adventures was born.”

Side hustles are launched when you align your work with who you really are as a person, Lee believes. She says that often what clients are best at is not what they are being paid to do. And more than anything, Lee extols the value of just doing it. She wholeheartedly believes in moving forward with what she calls “imperfect action.”

“Even indecision is a decision,” she says. “We want to feel safe, but until we act on something, we can’t really see if it makes sense, so it’s important to just start.”

One final nugget of wisdom that Lee doles out to her audience is to look at your side hustle as a way to solve problems that resonate personally. Ask yourself: What do I want to solve in the world? What pisses me off in my life right now? What questions do people ask me?

Rise of the Side Hustle


Kara McMaster is a serial entrepreneur who believes in the power of creative solutions to longstanding problems. Alongside her husband, she started Caveman Grocer, a ready-made paleo meal delivery service, in 2012. The concept was motivated by a desire to eat healthy, but the couple’s busy schedules left little time to cook nutritious meals. They repeatedly heard the same complaints within their social circle.

“Like everyone, we had busy lives and would sometimes sit and dream about what it would be like to have a healthy meal prepared and put in front of us on the table by a personal chef,” McMaster admits. A meal delivery service made sense and since then, Caveman Grocer has grown into a successful seven-figure e-commerce business with new product lines and a business model primed for growth.

But riding the coattails of that success isn’t McMaster’s style, so this year, she added a side hustle to her repertoire. After winning the Whistler Chamber of Commerce 2017 Rising Star Award, the spotlight shined on Caveman’s impressive online presence, and people were calling for her advice on how to replicate that success. McMaster Digital was born.

With a love of digital media and an opportunity to help other start-ups gain a leg up, McMaster grew her knowledge base through courses and other resources. She has consistently built her client list since launching a few months ago and is now finding creative ways to outsource her expanding workload.

As if all that wasn’t enough to juggle, she has a toddler, with another baby on the way in June. “I had no idea just how busy a person could be until I started this business on top of everything else,” she says with an exhausted sigh. “But side hustles are created because you have an itch to scratch and I wouldn’t have been happy if I didn’t pursue this digital media business.”

When asked why she thinks this area has ignited with entrepreneurial ventures, McMaster reckons that the Sea to Sky corridor is a breeding ground for side hustlers. “We live in one of the most expensive places in the world without having a lot of jobs that support the kind of income that it takes to sustain living in this resort,” she says. “I have a friend who sells vintage clothing online and another friend trying to raise two young children while launching a cross-fit business. We could all easily move to the city, where housing is virtually the same price, and find jobs that paid a lot more, but we don’t want to settle. We stick to why we moved here in the first place and hustle to make it work. If you can accomplish that while fulfilling your passion, that is just a huge bonus. There’s a reason why businesses, entrepreneurs and hustlers are born here—we are risk takers who aren’t afraid to work hard and bend the rules.”

Rise of the Side Hustle

Apparently, the Sea to Sky Corridor isn’t the only locale willing to push hard for side-hustle success. Recent research by web hosting provider GoDaddy found that 37 per cent of adult Americans now have side hustles. Further, an Intuit 2020 Report predicts that 45 to 50 per cent of the market will contain independent contract workers by 2020.

It’s a new trend that isn’t disappearing anytime soon. In a business climate where companies are constantly facing staff shortages, it will be vital to foster an open and accommodating workplace.

Lee of Screw the Cubicle has noticed that companies are warming up to the fact that employees must be happy, and often what makes them happy is being a part of ventures outside of their workplaces. “We need to reinvent how we keep our employees because people want to have it all: children, hobbies, dreams, passion—so companies need to adapt to the wave of change.”

Studies support that sentiment. In December 2017, Forbes shared a report asserting that happy employees are up to 20 per cent more productive than unhappy ones. And happy employees are also good news for organizations. The stock prices of Fortune’s “100 Best Companies to Work For” rose an average of 14 per cent per year from 1998 to 2005, compared to six per cent in the wider market.

Happiness seems to be a strong motivator in the realm of side hustles, but for those not quite ready to quit their day job, it goes beyond that. Side hustles can provide an outlet to explore passions, test ideas and gradually build a business that just might become a main hustle.

Cathy Goddard is the Founder of Lighthouse Visionary Strategies and the award-winning Lighthouse Mentor Program.  She writes the Lighthouse Blog and feature stories for Pique Newsmagazine.

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