The Canadian Money Roadmap

Expectations, Upsets, and Investing: Lessons from Baseball and the Market

Oct 15, 2025
Discover the surprising parallels between the Toronto Blue Jays' playoff journey and investing. Explore how emotions can cloud judgment during winning streaks. Learn why managing expectations is crucial in both sports and financial markets. Understand the role of cash for short-term goals, and how stocks and bonds differ from speculative assets like Bitcoin and gold. Gain insights on risk management and the importance of preparing for market declines. Tune in for valuable tips on staying grounded in the world of investing!
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ANECDOTE

Blue Jays Surprise Run

  • Evan describes recording from his truck while the Toronto Blue Jays unexpectedly reached the ALCS despite low preseason expectations.
  • He uses the team's surprising run to illustrate how short-term success can reshape expectations and lead fans to assume winning will continue.
INSIGHT

Momentum Can Warp Expectations

  • Evan connects sports momentum to investing, warning that living in the moment makes us assume current states will continue indefinitely.
  • He highlights that positive streaks can create unrealistic expectations about future performance.
ADVICE

Keep Cash For Planned Expenses

  • Remember "this too shall pass" when markets are high or low and treat stocks as risky assets that can decline in value.
  • Keep cash for planned expenses so you don't force selling investments during downturns.
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