Imagine working from your laptop anywhere in the world—earning Canadian dollars while sipping coffee in Spain, watching sunsets in Montenegro, or taking beachside breaks in Thailand. You’re keeping your income, but leaving behind freezing winters and sky-high costs.
In many countries, your entire living expenses such as rent, groceries, meals out, and even weekly cleaning, can cost less than a cramped $2,500 apartment in Toronto or Vancouver.
That’s the digital nomad lifestyle—and it’s no longer just a dream. Over 35 million people are living this way, and more Canadians are joining them every year. From 2020 to 2024, long-term emigration quietly climbed as remote workers chased freedom, affordability, and sunshine.
I’ve lived it myself—working across Asia, Latin America, and Europe—and now I help Canadians navigate the financial and tax realities of making this move.
In this blog post, I’ll walk you through 7 key steps of how to leave Canada and become a digital nomad—from beginner to advanced.
💡 Don’t skip Step 3. It’s the one that makes or breaks your plan.
1. Decide What Kind of Digital Nomad You Want to Be
Before you book that one-way ticket, take a step back and ask: What kind of digital nomad do I actually want to be?
Do you want to travel every few weeks, chasing new countries and passport stamps? That’s fast travel—high energy, lots of variety… but it can be exhausting. Or are you more of a slomad—someone who likes staying in one place for a few months, getting to know the local café owners, joining a gym, and finding a routine? Slower travel is often cheaper, more sustainable, and easier for remote work. A lot of people start off fast then transition to slower travel.
Ask yourself:
- Are you comfortable with risk, flexibility, and solo time?
- Are you in pure adventure mode, or looking to build a long-term lifestyle?
- Do you want this to be a temporary escape, or the start of a new chapter?
Your answers will shape everything—from where you go, to how much money you need, to whether you should apply for long-term visas or just hop around on tourist stamps. If you’re not quite sure what type you want to be, you can…
🌍 Find Your People
This journey’s way better with community. Here’s where to find one:
Online:
- Reddit: r/digitalnomad
- Facebook groups, Discord channels, Slack workspaces
In-person: (doing a test run)
- Join coworking spaces, local Meetups, or hang out in nomad hotspots like Lisbon, Medellín, Chiang Mai, Da Nang, or Bali
- Stay at coliving spaces like Selina or Outsite for built-in community
- Want structure? Try programs like Remote Year, Nomad Cruise, or WiFi Tribe
You’ll grow faster, avoid mistakes, and have more fun when you connect with others doing the same thing.
2. Research the Lifestyle and Destinations
Once you’ve figured out your travel style, it’s time to get into the details.
Start with tools like NomadList and Numbeo. These sites help you compare cities based on:
- Cost of living
- Internet speed
- Safety and weather
- Visa rules
- Expat/nomad friendliness
Look for places with reliable Wi-Fi, good infrastructure, vibrant communities, and great food. Bonus points for visa flexibility.
✈️ Great Starter Cities
- Chiang Mai, Thailand – Legendary nomad hub. Super affordable, safe, full of coworking spots. Avoid burning season (Jan–Mar).
- Da Nang, Vietnam – Beach city with great cafés, fast internet, and fewer crowds than Bali.
- Bali, Indonesia – Beautiful but crowded (especially in Canggu). Still great if you find the right area.
- Medellín, Colombia – Spring weather all year, affordable, solid coworking options.
- Kuala Lumpur, Malaysia – Super underrated. Clean, modern, diverse, with great food and easy transport.
- Lisbon, Portugal – Popular among European nomads. Good vibes, good food, decent visa options.
- Mexico City / Playa del Carmen – Cultural, vibrant, affordable, and a short flight from Canada.
Meet jason. He is an online web developer. He was spending about $5,000 a month in toronto, and barely making ends meet. He negotiated a remote work with his company, and now he lives in chiang mai for $2000 a month, eating out almost every meal, having a maid, and more.
🛂 Understand Visa Options
Most nomads start with tourist visas (30–180 days in many countries for Canadians).
Looking long-term? Many countries now offer digital nomad visas, including:
- Portugal, Spain, Croatia, Colombia,, Estonia, and more
These usually require: - Proof of income
- Health insurance
- Clean criminal record
- Minimum monthly income (e.g., ~$1,200 in Colombia vs. $6,000+ in Estonia)
- There’s also other types of visas
3. Build Monetizable Skills for Remote Work
This is the most important step, and the one that will make or break your plan. You need a skill that earns money online.
There are three things to figure out:
- What kind of remote work you want
- What skills are in demand
- Where to find paid gigs
A. Career Paths
1. Remote Job
Work for a company full- or part-time from anywhere.
✅ Stable income
❌ Time zone issues, fixed schedule
2. Freelancing
Offer your services to clients on a project basis.
✅ Full flexibility
❌ Income ups and downs, always looking for clients
3. Online Business
E-commerce, coaching, SaaS, or digital products.
✅ Unlimited upside, full control
❌ Slow to grow, risky at first
4. Passive Income / Side Hustles
YouTube, affiliate links, online courses, investing.
✅ Long-term freedom
❌ Takes time—don’t rely on this to start
Note: In-person teaching jobs in Korea or Japan aren’t truly “digital nomad” paths. You’re not online or mobile.
B. In-Demand Skills
Tech: Web/dev, software, data science, cybersecurity, automations
Creative: Writing, copywriting, video editing, graphic design, SEO
Communication: Online ESL, customer support, translation
You’ll also need to know tools like Slack, Notion, VPNs, Zoom, and project trackers.
C. Where to Find Work
Remote jobs: Try to ask current employer if applicable. We Work Remotely, FlexJobs, Remote OK
Freelancing: Upwork, Fiverr, Toptal
Networking: LinkedIn, Reddit (r/remotejobs, r/freelance), nomad Facebook groups
Pro tip: Tailor your resume for remote roles. Show time management, async experience, and ability to work independently.
4. Tax Planning: Should You Become a Non-Resident?
If you’re planning to live abroad long term, it’s crucial to understand your tax residency. The CRA doesn’t care where you physically are—they care about your residential ties: things like owning a home in Canada, having a spouse or dependents there, or keeping Canadian bank accounts, memberships, or health coverage.
You’ll usually fall into one of a few categories:
Resident – You’re taxed on your global income, even if you live abroad.
Factual Resident – You’re away temporarily but still considered a resident. Same global taxation applies.
Non-Resident – You’ve severed most ties and are only taxed on Canadian-source income (like rental income or dividends).
Becoming a non-resident has benefits—you no longer have to pay Canadian tax on your income if you’re not physically there—but you need to sever your ties and deal with the departure tax. That means reporting and potentially paying tax on capital gains as if you sold your assets the day you left.
- Form NR73 (to request an official residency opinion)
- T1161 (list of assets over $25,000)
- T1243 (departure tax report)
Don’t guess on this stuff. Taxes for digital nomads can get complicated fast, and one wrong move could cost you thousands in penalties. At Blueprint Financial, we help Canadians navigate this exact process — from deciding whether to become a non-resident to finding the most tax-efficient way to live abroad.
As we like to say, “Build the life you want, with the right Blueprint.”
👉 Book a discovery call with our Exit Canada planning team
👉 Learn more at BlueprintFinancial.ca
5. Financial Prep Before You Go
Let’s talk money—because digital nomad life can have a lot of unexpected costs, especially at the start. First, total up your relocation costs: flights, visas, insurance, initial accommodations, vaccinations, gear, and any final bills in Canada.
Then, save at least 6 months of living expenses based on your target country. If Da Nang costs $1,500/month, that’s $9,000. Use sites like Numbeo or NomadList to estimate accurately.
On top of that, add a $5,000 CAD emergency buffer. This covers medical surprises, visa runs, tech breakdowns, or last-minute flights—so you’re not financially stranded.
Set up a travel-friendly banking system:
- Open a Wise account for multi-currency access
- Use cards with no FX fees like EQ Bank, Wealthsimple, or Scotiabank Passport Visa Infinite
- Set up mobile banking so you can freeze cards instantly
- Carry a backup card, just in case
Get your money organized before you leave. It’s the difference between freedom and financial stress.
6. Cut Ties, Get Prepared
Before you leave Canada, you need to do two things: lighten the load and stay reachable.
Start by cancelling anything you won’t use abroad:
- Phone plans, subscriptions, gym memberships, utilities
No sense paying for services you’re not using.
Next, deal with your stuff:
- If you’re coming back, rent a small storage unit or use a friend’s garage
- If you’re going long-term, sell everything. Facebook Marketplace and Kijiji is your best friend. Travel light, live free.
To keep your Canadian phone number, use a VoIP service like Fongo. It works over Wi-Fi and lets you receive texts and calls for banking, 2FA, and staying in touch.
And don’t forget healthcare and connectivity:
- Most provincial health plans expire after 6 months abroad
- Get international health insurance
- Staying long-term somewhere? Look into local insurance too
For staying online:
- Use eSIMs like Airalo or Holafly, or buy local SIMs
- Bring a portable router (Skyroam, Netgear) for backup Wi-Fi
Before we move on, if you’re thinking about leaving Canada, make sure you’re not missing any key steps. I put together a free guide on the 7 biggest CRA tax traps Canadians face when moving abroad. Download it free—link is here:
📥 https://blueprintfinancial.ca/exit-canada-tax-guide-download
7. Go Time: Book It and Go
This is the fun part—actually making the leap.
- Book your flight
- Reserve an Airbnb or short-term rental for your first month
- When you land: get a local SIM card, test the Wi-Fi, set up your workspace, and make sure your bank apps work
Pro tip: Start slow. It’s easy to burn out if you try to work full-time and explore every day. Ease into the lifestyle and find your rhythm.
“You miss 100% of the countries you don’t book flights to.” – NOT Wayne Gretzky
Bonus: Long-Term Global Living
If you fall in love with this life and want to stay on the road, here’s how to go next-level:
- Apply for a digital nomad visa or residency permit (many countries now offer these)
- Look into second residencies or citizenships for more travel freedom
- Consider setting up offshore structures or international businesses for tax optimization
- Track your travels carefully to stay under the 183-day rule and avoid triggering tax residency
This is where tax planning, legal setup, and strategic travel combine to give you total freedom.
No matter how far your digital nomad journey takes you, I can guarantee you this: you will learn a lot about yourself and about what you want out of life.
“Travel far enough, you meet yourself.” – David Mitchell
Living a location-independent or globally mobile lifestyle can be incredibly rewarding—but only if your finances, taxes, and long-term strategy are working for you, not against you. That’s exactly why we created Blueprint Financial: to help Canadians with international goals gain clarity, confidence, and a real plan for the future.
👉 If you’re curious about what’s possible, check out our financial planning services and see how we can help you map out your next steps.
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Your global dreams deserve a solid foundation. Let’s build it together.
