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Prepared by: Willow Wealth Management

June 04, 2026

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Playing the Long Game

 

One of the best investing stories out there follows "Mark," the world's worst market timer. The premise is almost too simple... But the conclusion is the kind of thing that shifts how you think about investing.

 

The chart shows the growth of $1 invested in the US stock market (inflation-adjusted) from 1870 to 2025, It highlights major crashes and downturns, such as the Great Depression, WWII, Black Monday, the COVID-19 pandemic, and recent inflation. Despite setbacks, the market’s long-term trend is upward

Source: https://www.morningstar.com

 

Mark started saving in 1970 at age 22. The problem was he could never bring himself to invest until markets had already run up significantly. He'd wait, second-guess himself, and finally pull the trigger at the worst possible moment. Let's go over all the times he pulled the metaphorical trigger:

  1. End of 1972, right before a nearly 50% crash.
  2. August 1987, right before Black Monday.
  3. December 1999, peak of the dot-com bubble.
  4. October 2007, right before the financial crisis.
  5. February 2020, right before the pandemic.

Five investments, five market peaks, and five crashes that followed immediately after.

 

Over his lifetime, Mark put in roughly $184,000 of his own savings.

 

And by retirement, his portfolio had grown to more than $1 million.

 

You may be asking yourself, "huh?" Because Mark didn't do anything right, except one thing: he never sold. Not after 1973, not after Black Monday, not after the dot-com collapse, not after the financial crisis, and not after the pandemic crash. He held through every single drawdown and collected every recovery that followed.

 

There're a few things worth taking away from Mark's story. Time in the market matters more than timing the market, and the math becomes increasingly forgiving the longer the runway you give it. Truthfully, the only market variable you can control is your behaviour. The next correction cannot be predicted, but whether to panic-sell when things get uncomfortable is a decision you have full control over.

 

Perfection is not required; patience is. And as Mark Twain once said: "history doesn't repeat itself, but it often rhymes”.

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<p>CIBC Private Wealth consists of services provided by CIBC and certain of its subsidiaries: CIBC Private Banking; CIBC Private Investment Counsel, a division of CIBC Asset Management Inc. (&ldquo;CAM&rdquo;); CIBC Trust Corporation; and CIBC Wood Gundy, a division of CIBC World Markets Inc. (&ldquo;WMI&rdquo;). CIBC Private Banking provides solutions from CIBC Investor Services Inc.(&ldquo;ISI&rdquo;), CAM and credit products. CIBC Private Wealth services are available to qualified individuals. The CIBC logo and &ldquo;CIBC Private Wealth&rdquo; are trademarks of CIBC, used under license.</p> <p>Clients are advised to seek advice regarding their particular circumstances from their personal tax and legal advisors</p> <p>&nbsp;</p> <p>This information, including any opinion, is based on various sources believed to be reliable, but its accuracy cannot be guaranteed and is subject to change.</p>
 
 
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CIBC Private Wealth” consists of services provided by CIBC and certain of its subsidiaries through CIBC Private Banking; CIBC Private Investment Counsel, a division of CIBC Asset Management Inc. (“CAM”); CIBC Trust Corporation; and CIBC Wood Gundy, a division of CIBC World Markets Inc. (“WMI”). CIBC Private Banking provides solutions from CIBC Investor Services Inc. (“ISI”), CAM and credit products. CIBC Private Wealth services are available to qualified individuals. Insurance services are only available through CIBC Wood Gundy Financial Services Inc. In Quebec, insurance services are only available through CIBC Wood Gundy Financial Services (Quebec) Inc.


CIBC Private Wealth services are available to qualified individuals. The CIBC logo and “CIBC Private Wealth” are trademarks of CIBC, used under license.