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Chautauqua Portugal 2019: What Makes You Happy?

Well, we are back from two straight back-to-back Chautauquas and once again it has been an EPIC time for everyone. This year we did 3 weeks: one in Stratford-Upon-Avon, UK and two in Portugal, and what I love about Portugal is It’s relatively unknown. People tend not to know what to expect when you mention Portugal. The landscape is frigging breathtaking. So having been here multiple times in our travels, it was with a great deal of enjoyment as I watched our guests board the shuttle, get driven up and down the windy, mountainous roads of the Douro Valley, and […]

Guest Interview with Craig, Author and House Hacker Extraordinaire

Long-time readers of this blog (thank you!) know that we retired at 31 to travel the world by doing the exact opposite of what our parents have been preaching—not buying a house. Given that the average single-family home cost over a million dollars in Toronto, instead of getting into massive amounts of debt, we rented. With all the money we saved from not owning a home, we shoved it all into the stock market, built a diversified portfolio and the rest, as they say, is history. The only real-estate we own are REITs (Real-Estate Investment Trusts), which lets us earn […]

Book Review: Choose FI, Your Blueprint to Financial Independence

“The FIRE is spreading.” One of my favourite things about the FIRE acronym is how powerful it is. Finance is generally a dry topic, so when most people think about finance, they think about spreadsheets, charts, graphs, reams of numbers—I just fell asleep in the middle of that sentence. It’s difficult to give it feeling and pizzazz. But the term “FIRE” makes finance sexy. So, when people hear the phrase “the FIRE is spreading”, it makes their heart pound faster, and as a result, they’re driven to act. This is why I love that phrase. And guess who came up […]

At Chautauqua, Drinking Port.

I must confess, sometimes retirement is not all it’s cracked up to be. Today is not one of those days. Most days I wake up and wonder out loud whether this awesome life we get to lead is actually real. I pinch myself to make sure it’s real. Every time, it is. But today, it is my honour and privilege to share this life with 30 other people! Because today, Chautauqua Portugal 2019 officially begins. It’s no big deal. Just hanging out with J.L. “The Godfather” Collins, our good friends and frequent ChooseFI guest stars Alan & Katie Donegan, and […]

Reader Case: Going Back To School In His 50’s

Usually when I read an email from someone asking for a case study, I can usually tell where it’s going within the first paragraph or so. This one, however, I must admit I started getting more and more alarmed the more I read. Our reader has made some…let’s say…expensive mistakes over their life, and as a result is writing to us at the age of 50 with no money and still going FURTHER into student loans. Needless to say, I wasn’t hopeful that we could pull him out of his financial nosedive, but people who know me know that I’m […]

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