Side Hustles

A great way to build experience and gain control over your income is to become your own boss through gig work or by starting your own business. Here are some steps to keep in mind when striking out on your own:

  • Do your research. Reach out to your network and search online for gig opportunities. You can search for jobs in your area with keywords based on your experience, such as “mover,” “driver,” “bartender” or “stagehand.” Find the best fit by filtering results by salary, experience level or job type.
  • Consider related positions. You may be able to apply your skills to other jobs you haven’t yet considered. For example, if you typically find gigs as part of a stage setup crew, you might consider finding mover jobs for companies or individuals moving from home to home.
  • Consider work for gig apps. There are many options available through online apps that allow you to quickly sign up and start working at your convenience, such as rideshare driving, food or grocery delivery, dog walking, moving services, yard work services, quick tasks and more.
  • Consider your existing hobbies. Think about harnessing the interests and skills you already possess that may lend themselves to a side hustle or a second career, like baking, babysitting, yoga, or makeup artistry.
  • Supplement with remote work. If you’re finding it difficult to get gig work, you might also consider looking for remote or online work. There are many options available for people with little or no experience, such as translation services, data entry or transcribing audio files into written documents.

Important to Remember

Please note that freelancer and entrepreneurial tools, apps, and websites are not necessarily free. Many charge fees and/or take a cut of revenues. Ensure that you have read the fine print before signing up for any service.

Using Self-Evaluation to Choose a Career

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Government of Canada

Starting a Business

Steps to consider before operating a business in Canada:

  • planning a business
  • choosing a business name
  • registering your business with the government
  • applying for business permits & licences
  • getting business support and financing

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City of Toronto

Training & Support for Business Start-Ups

Toronto Small Business Enterprise Centres provide:

  • guidance
  • info & tools
  • one-on-one consultations 
  • business registration assistance
  • business plan review
  • info on small business funding
  • business permits & licences 
  • importing & exporting
  • business seminars
  • youth entrepreneurship programs
  • mentoring & networking opportunities 

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Government of Alberta

Training for Work: Self Employment

Under Training for Work, this program assists with:

  • facilitating entry into self-employment by offering formal instruction
  • business plan development
  • one-on-one business counselling
  • coaching
  • guidance & follow-up

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Manitoba Jobs and Skills


Self-Employment assists eligible individuals with starting their own business through:

  • training and supports to develop business plans & entrepreneurial skills
  • individual coaching/consulting

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Self-Employ PEI

For job seekers, Self-Employ PEI offers financial support and business counselling to new entrepreneurs during their first year of operations.

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Small Business BC

Small Business Marketplace

This digital marketplace supports small business and encourage residents to buy local.

Business How Tos & Checklists

To help small business owners achieve their goals, Small Business BC has complied free business checklists, how-to guides, and resources.

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Work in Culture

Entrepreneurial Resources

Work in Culture has compiled resources for entrepreneurs, including:

  • Business Planning Basics
  • Exporting
  • Partnership Basics
  • Marketing Basics
  • Digital Marketing

CreativeBoost: Countdown to Business

Work in Culture is offering three interactive two-hour sessions on August 25, 26 & 28 geared towards artists, creatives, and cultural workers thinking about starting a creative business.

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The Actors Fund (US) 

The Creative Entrepreneur Project

The Creative Entrepreneur Project equips creatives with resources to successfully navigate the entrepreneurial journey and increase their income and independence through business ownership. The program provides assessments, seminars, workshops, resources, tools, supportive services and groups intended to provide our community with a framework to successfully explore, launch and sustain an entrepreneurial endeavour. 

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Digital Main St.


DMS shopHERE provides independent small businesses and artists with a quick, easy and no-cost way to get selling online. Through the program, participants receive:

  • hands-on assistance setting up and launching their online store
  • training to support their online store, including topics such as digital marketing, shipping and inventory management
  • access to free tools to help support the launch of their online stores

Ontario Grants

The Digital Transformation Grant Program provides training, guidance, and the opportunity for main street business to apply for a grant of up to $2,500

The Digital Service Squad Grant Program is focused on providing one-on-one assistance to small businesses in Ontario. It will include training, advisory support, and a grant to support the Digital Service Squads. 

Future Proof

The Future Proof program assists businesses identify new markets, pivot their business model, develop and implement a deep digital transformation plan. 

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“Etsy is the global marketplace for unique and creative goods. It’s home to a universe of special, extraordinary items, from unique handcrafted pieces to vintage treasures.”

The Etsy Beginner’s Guide takes new members through the steps of opening an Etsy shop. Etsy doesn’t require sellers to have a business license to sell on Etsy. However, when selling on Etsy you’re required to follow any laws that apply to you as a small business selling online.

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Futurpreneur helps aspiring business owners (18-39) launch businesses across Canada through financing, mentoring, and additional resources. Their three primary programs are:

  • Start-Up
  • Mentoring
  • Side Hustle

Airbnb Online Experience

Become an Experience Host on Airbnb and share your talents and skills from the comfort of your home. What can you offer that would make for a fun, unique experience? Some creative online experiences being offered include: 

  • “Make a Traditional Mexian Piñata”
  • “Creative Smartphone Photography at Home”
  • “Virtual Walk-through Athens Street Art”


Upwork connects freelancers with job postings which match their specialized skill set. 

The Upwork freelancer education hub offers tutorial videos which guide freelancers through the entire process and gives tips on how to be successful on the app. 


Like Upwork, Freelancer is a crowdsourcing marketplace which connects freelancers with job postings.


Teaching English online is a great option for flexible, remote work. VIPKid allows you to choose your own hours, provides lesson plans, and pays between $14-22/hour. Teachers are required to have two years of experience in teaching, tutoring, coaching or mentoring, a four year degree from a university, work authorization in the US or Canada, and reliable technology. 


Ride sharing services allow drivers to set their own schedule and earn money with their own car. Requirements do vary from city to city, but generally drivers must meet the minimum age to drive in their city, have an eligible mode of transportation, and submit required documents, including a valid driver’s license. Review the requirements in your city.

Drivers, cyclists, and pedestrians can all work for Uber Eats, delivering food on their own schedule.


Lyft is another ride share company offering flexible work. Requirements vary across cities, but at a minimum drivers must meet the age requirement for their region, have a smartphone, and pass an online DMV and background check. Review the requirements in your city.


TaskRabbit is another freelancer platform. Their “same-day service platform instantly connects…skilled Taskers to help with odd-jobs and errands.”


Fiverr is a platform for connecting skilled freelancers with gig work.


“Earn money transcribing or captioning from home.” This is a great option if you speak more than one language because rates are almost double for translating subtitles.


Delivering food through SkipTheDishes is another avenue for picking up extra work on your own schedule.

Virtual Assistant Service

Another freelance, remote work option is becoming a virtual assistant. Through The Virtual Savvy you can sign up for pre-recorded training called “Become a Booked Out Virtual Assistant.”

Word of Mouth

This spreadsheet, compiled by Rachel Meade Smith, is a list of interdisciplinary, remote-friendly employers.