What does it actually mean to win at retirement? A bigger house, more expensive vacations, and a larger income during your working years may look like success, but they don't necessarily determine how satisfying retirement will be.

Jeremy Keil compares two composite retiree stories drawn from situations he's encountered over the years. One represents someone who never earned more than $80,000 in a year but consistently saved, paid off a mortgage, accumulated rental real estate, and built investments worth roughly 10 times their income. The other represents a retiree who earned around $300,000, enjoyed spending bonuses along the way, retired with a mortgage, and accumulated investments worth roughly five times their final salary.

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