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How To Make the Most of Your Side Hustle


Increase your chances of success with these three Ps

Women's hands typing on white laptop, a cup of coffee, office table
iStock:Delmaine Donson

Twitter, Groupon, Under Armour, Craigslist, Etsy — these are all big-name companies that started out as passion projects. Today, out of necessity or restlessness, more people than ever are trying to capture their own lightning in a bottle. 

In the past year, according to survey data, 42 per cent of Canadians pursued opportunities to supplement their income and 64 per cent were considering ways to do the same in the year ahead. The side hustle is growing in popularity south of the border as well, with 40 per cent of Americans currently operating a small business on the side.

“Doing an additional thing next to your full-time job sometimes comes out of necessity,” says Nusa Fain, director of the Master of Management Innovation and Entrepreneurship program at Smith School of Business. “On the other side are people identifying a problem that they’ve had that they want to solve and are passionate about.” 

Fain notes that the effects of the pandemic have inspired many people to re-evaluate what’s important to them and how they want to spend their time. “We’re seeing a move away from the ‘work to live’ mentality, and more people seeking and opting for work that has purpose,” she says. 

Launching an entrepreneurial venture is one way to align work with values. Doing so as a side hustle can also be a great way to test the waters while minimizing risk. On the flip side, finding your entrepreneurial footing requires time outside of work that could be devoted to family and friends or personal wellbeing.

So how can those looking to dive in or who have already taken the plunge increase their chances of success? Fain and two business owners who launched their ventures off the side of their desks — ­Kristi Soomer, founder and CEO of Encircled Inc., and Connor O’Shea, co-founder and CEO of Westgen Technologies Inc. — agree that you can boost your odds with a combination of passion, planning and people.

Passion: Find something that fuels you 

There are different schools of thought when it comes to the role of passion in the entrepreneurial journey. Some research suggests passion is what fuels the entrepreneur’s persistence and no-quit attitude. Other literature proposes that passion can evolve from entrepreneurial efforts.

It’s possible that both are true. Soomer, a former strategy consultant in the retail industry who travelled extensively for her job, says she felt called to create an adaptable clothing product that could take her from the plane to the office to dinner and, finally, to the couch.

“I was also looking for more values alignment in what I was doing personally and in my career,” she says. “I was wanting to focus more on sustainability and ethics in business.” A decade later, Encircled has grown into a sustainable work-leisure clothing brand. 

“You’re going to live and breathe this idea for probably the next five to 10 years so you better be passionate about it,” she advises. 

In O’Shea’s case, he was more drawn to the concept of entrepreneurship itself. “I’m living my dream in terms of what I’ve always wanted to do,” he says. 

His company, Westgen Technologies, offers emission reduction solutions for the oil and gas industry. It’s an area he and his brother-in-law and business partner know well: both have backgrounds in mechanical engineering and spent time working in oil and gas. 

“In hindsight, I’m glad that I did something that was in my domain of expertise because it really helped us to fast-track the process,” he says. “Because we had relationships, we were able to establish trust, we had credibility, and that made a huge difference.” 

Whether the source of your passion lies in offering a solution to a business challenge or the desire to invest and build a business from the ground up, the important thing is that you feel empowered. “A side hustle should be something that really fulfills you,” Fain says. 

Planning: Time management is your friend 

Translating passion into performance is no simple task, but as Theodore Roosevelt said, “Nothing worth having comes easy.”

The biggest challenges entrepreneurs face when growing their side hustle is the lack of time. Juggling a full-time job, new business and other obligations is a challenge. “Plan where you want your side hustle to be in the short term and then plan backwards,” Fain says. “Having a roadmap will help with your time.”

You also want to be mindful of your current employer’s interests. “They are the ones paying your salary at the end of the day, so you want to give them the best time and the best efforts,” says Soomer. “As an employer, I can tell when someone is not engaged in the business. It’s very obvious.”

You’ll also want to ensure there are no stipulations in your employment contract that limits moonlighting, she notes.

O’Shea says your relationships and reputation are all that you have and that they need to be nurtured. “You don’t have a big organization or a track record if you’re a first-time entrepreneur. So it’s really important you don’t burn bridges and you’re seen as having integrity.” For him, this meant working in the evenings and on weekends, and not discussing his side hustle at work. 

The important thing is to set a sustainable pace. Operating a side hustle can be exciting, but burning the candle at both ends can lead to burnout. If maintaining a social media channel is a key component of your business, consider social management platforms such as Sprout Social, Later or Planoly to automate some tasks. As well, consider outsourcing work, such as accounting or website design.

“Don’t give up too much of your life for it,” says Fain. “You’re no good to anybody, or your side hustle, if you don’t take care of yourself.” Sacrifices will have to be made but finding a balance is key. “Things you do outside of work are what give you energy to keep going.” 

People: Don’t be afraid to ask for help 

The road to entrepreneurship is rarely a straight line. A study of 400 entrepreneurs whose businesses began as side hustles found individuals spent an average of 20 hours per week working on their venture and it took an average of 19 months before they led their business full time. 

“You’re not doing it wrong if you feel like you’re spinning in circles and going backwards and forwards,” says Soomer. “That’s just entrepreneurship.”

One area that side hustlers sometimes fall short is seeking out help, be it within their personal network or the entrepreneurial ecosystem itself.

O’Shea says he was astounded by the number of resources available to help entrepreneurs take their ventures to the next level, from government programs and funding to accelerators, incubators, courses, workshops and events.

“Do a Google search and get on the mailing lists of any entrepreneurial-related organizations in your geography and then just show up at their events,” he says. “You meet people and benefit from the network effect. You tell someone what you’re trying to do and they say, ‘Oh, I know somebody who can help you with that.’”

You may also reach a point where you’ll need to lean on people in the operation of your business. “A lot of founders really struggle with losing that piece of control,” Fain explains.

She adds that, aside from quitting a full-time job too early, holding on for too long and thinking you can do it all on your own is the other big mistake side hustlers make. “You will need to give up some of that control in order to be successful and facilitate growth,” she says. “You can outsource stuff without giving away equity.”

There is no one right way to successfully pull of a side hustle. There are side hustlers whose dream it is to take their venture full time and those who are content to keep their hustle on the side. (Doing so can even have positive effects on your full-time gig.) Regardless of the route you take, having a combination of passion, planning and people will increase your odds of reaching your goals.

“Always remember why you’re doing it,” says Fain. “A side hustle that empowers you will make it easier to overcome any obstacle.”