Mike’s a semi-retired Canadian expat off his leash, Oshin is a force of nature that wouldn’t settle for a third-world pay grade. They met after working together virtually for a few years, eloped in the Philippines, and have experimented with the art of living, ever since.

This blog is about where we go, what inspires us, and explains in detail the numerous ways how we consistently make money online that’s required to foot the bill on a travel-intensive lifestyle, month after month, 8+ years and counting.

Start here to engineer your own location independence.

Here we dish out a wide range of proven methods to realistically meet our budgetary requirements for a permanent digital nomad lifestyle, while maintaining a healthy savings account.

Sailing Into the Future

After the 2020 pandemic broke out and Oshin gave birth to our first born son the following September, we felt compelled to plan for the future and plotted a course for the next few decades.

We were going to head to Canada in 2021 but we are no fans of medical segregation and I think Trudeau is an ass hat. So we pivoted and settled into a small tropical island, far from much of the disruption that the management of the pandemic has caused internationally.

When our son Hank is 3 – 5 years old, our goal is to acquire a boat, learn to sail and continue our lifestyle in the tropics.

Working With Brands

We’re always open to partnering with brands, bloggers we’ve met along the way, and individuals who share our interests. If you’d like to hire us for your project we invite you to browse our services.

Don’t miss out on anything we’ve got tucked away on Hobo with a Laptop —start here and begin your own journey to self-sustained location independence.

Related: How to Become a Digital Nomad, Step-by-Step

Canadian Digital Nomad

The Backstory

In 2017 Mike got married to a brown-eyed bombshell named Oshin, after working virtually with one another for years.

Oshin worked from the Philippines as a content manager for a UK search optimization company, and at the time Mike was freelancing under her to finance his travels.

After working together for just over a year, Mike decided it was time to launch another business and he couldn’t do it without her help.

Together they started an internet marketing agency called Copyrise (which was later folded into our services page).

He offered Oshin a position as his full-time virtual assistant, where she held that role for a year –before they finally met in person when Mike was passing through Cebu, Philippines en route to Canada.

nomad family

When Mike and Oshin finally met in the Philippines, everything was natural. It felt like coming home after a long absence, not meeting for the first time. Inseparable, everything clicked. And one year later they got married.

Combining their efforts on Hobo with a Laptop was the next logical step in their passion for travel and building a business through blogging.

Fast forward to present day –we’re proud parents of a little nugget dude named Hank. Our plan is to raise him on a sailboat full-time far from the troubles of land life, we’ll home school, and document everything.

Where’s the Money Coming From?

We funded our early travel experiences with part time remote jobs in digital marketing and design. Today our six figure income is 100% passively generated through mostly evergreen web content.

Let us show you how we did it, start here.

Digital Nomad Lifestyle Blog


Hobo with a Laptop

Mike’s been a Canadian digital nomad since the age of 18, long before there was a term for it. He’s now lived in Asia for roughly a decade.

Before that, he wrapped up his Toronto-based career as an enterprise ecommerce professional who worked with Fortune 500 brands and a team of 20+ skilled developers.

In his early twenties he was art director for the Burlington Jazz & Blues Festival, a freelance web designer, ecommerce consultant, and trained sales professionals in the tech industry.

Since he went ‘full nomad’ in 2013, he’s moonlighted as a film extra, become a best-selling author, professional copywriter, and occasionally helps brands tackle their digital marketing.


Hobo with a Laptop

After acquiring a bachelor’s degree in English, Oshin took the corporate life out for a spin for several years before figuring out there was more to life than a buck fifty per hour and zero job security in the Philippines.

Surrounded by over 7,000+ islands, living in the Philippines was torture if she wasn’t able to explore them.

Travel seemed like a luxury only foreigners could afford and she was determined to overcome the financial barriers that held her back from nomad travel.

She decided she’d had enough and went solo; working through the years as a freelance copywriter, ebook publisher, search engine optimization specialist, virtual assistant, and social media designer.

Buy us a coffee if you dig our content.

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