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All-In Digital Entrepreneur when I Go Back to Canada: Crazy?

Canada: What to Do

I’ve talked about moving to Canada in previous blog posts, and it’s now less than a year away (March 2016). I’ve started preparing in numerous ways such as gathering information about how to get the cats and my stuff back to Canada and also giving away/selling lots of my stuff that I wasn’t really using that much.

How Can I Make Money in the Great White North?

But, the really big question in this whole equation is what I’m going to do for work when I go back. While I do enjoy my job as an ESL teacher, doing that in Canada isn’t ideal due to the serious competition for jobs and the resulting low-pay. Scrambling around for $20/hour part-time jobs really just isn’t my style.

Personal Finance= Soul Death

I briefly considered personal finance but after further research, it seems that I’d likely end up selling things like whole life insurance or mutual funds, both of which would slowly make me feel dead on the inside since I think both of these things are terrible products and I’d hate to rip people off, because that also certainly is not my style.

Human Resources= the 9-5

The next thing I considered was human resources. I’d have to go back to school for a couple years and I think it’d be a pretty good fit for me, with my background in psychology and how in these previous 10 years, I’ve been doing plenty of admin stuff and also working with people for my job. Except doing the 9-5 with only 2 weeks vacation might make me feel a little dead on the inside too. I could potentially make decent money, but I’m not sure I’d be happy.

Digital Entrepreneurship: The Dark-Horse Winner?

What actually makes me happy is doing online stuff and writing books. Like I totally feel happiest when I don’t have any classes and I go into the office and I nerd out starting a new website, or I sit down with a cup of coffee and write, or I respond to a question that one of my readers has and I feel like I can actually help them.

Is it crazy to go all-in on the digital entrepreneur thing when I go back to Canada and try to make a living off of that? I initially thought so, but the more people I talk to, the more convinced I become that this could actually work. During these past 10 years in Korea, I’ve basically had no boss and/or supervision and I’ve LOVED it. Also, I love organizing my time how I want to by getting up early and doing work, exercising, cooking lunch, working more and then chilling out with friends or the cats in the evening.

What I Have Going for Me:

A Pool of Cash. By this time next year, depending on the markets (which seem to be going nowhere but up), I should have around a quarter million in investments and cash reserves. This could tide me over for 10 years in Canada, even if I didn’t earn another dollar, which obviously wouldn’t be the case.

Miscellaneous Skills. I’m pretty good at a lot of things and although I don’t have a lot of connections back in Canada right now, I have no doubt that I could quite easily pick-up some temporary or part-time work if necessary. I’m also really good at networking, so I’m confident in my ability to quickly make the connections I need, wherever I choose to live.

Increasing Sales of my Ebooks. Sales of my 2 books, How to Get a University Job in South Korea and The Wealthy English Teacher have been encouragingly strong, even with no paid advertising. My free advertising consists of about 3 minutes/day of posting in various Facebook groups, so obviously the potential is there for a lot more growth.

A Growing Email List. Pat Flynn and the other Internet marketing gurus talk about the importance of an email list, a lot. My email list is growing by leaps and bounds because of this new website that I started a couple weeks ago, ESL Speaking. The 2 books I’m writing now will fit extremely well with what people who signed up for the list are looking for, so I’m optimistic about future sales.

The Ability to Live Frugally. If necessary, I can live extremely frugally. Like I truly loathe shopping, generally eat homemade vegan food and love riding my bike and walking places. I can give up expensive hobbies like skiing or scuba diving when I go back to Canada without really a second thought.

Time in Abundance. I’m currently making around $500/month and sometimes up to $700 in passive income, and I only spend around 10 hours/week working on it. Only recently have I figured out how to do it well by building an email list and getting into self-hosting my websites. As my friend said to me the other day, imagine if you spent 40 hours/week on your online stuff? It’d potentially be huge. I totally agree with him.


Is this the craziest plan you’ve heard in a while? Or, maybe not so much?


  1. The only crazy thing i see is considering doing something you don’t love.

    Regarding personal finance, it’s not possible be an “investment advisor” without having that piece of paper on the wall? I could see you being a great and affordable account manager for expats (or anyone really..) …

    • Yes, it is possible to be an adviser without the paper on the wall. But, it’d be hard to build up a client base without it (I think). Would you, for example, pay me to help you? I don’t know!

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