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Jolene Unland's avatar

Most mainstream retirement content—books, blogs, financial advice, even lifestyle tips—is written by and for the middle class. These narratives often reflect middle-class anxieties: fear of running out of money, identity loss, the importance of staying “productive,” etc. As a result, retirement is framed as a cautious, defensive phase rather than a liberating one. Scarcity, not abundance, is the underlying tone. “Success” is still defined in terms of hustle, busyness, budgeting, or passive income hacks—not freedom, leisure, or optionality.

In contrast, the wealthy tend to retire very differently—often earlier, with more confidence, and on their own terms. But we rarely hear their stories because the truly wealthy don’t need to justify or explain their lifestyle.

Their lives are often private or intentionally under the radar.

When they do speak, it’s more likely through the lens of entrepreneurship, legacy building, or philanthropy—not “retirement.”

In a nutshell, much of the mainstream retirement narrative is limited as the microphone is held by those still living within a middle-class frame. That skews what “retirement” even means in the public imagination.

Thanks again, Jordan, for providing rich content outside the mainstream.

Paul Millerd's avatar

This is sort of a hidden benefit of self employment. Theres no upward smooth trajectory of income and therefore you have to get comfortable with spending more than you make sometimes. This helped me realize I had my own fears of spending I’ve decided to tango with

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