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W-2 by Day, 1099 by Night: The New Middle Class LLC

W-2 by Day, 1099 by Night: The New Middle Class LLC

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 This podcast first existed as a newsletter. Read it here. More Americans need multiple jobs just to stay afloat. What used to be a “side hustle” has quietly become a second paycheck, a safety net, and for millions—a way to survive when one full-time income no longer covers the basics. In this episode, we break down how the old social contract—one job, one income, one safety net—has unraveled. We look at the data behind the shift, from rising 1099 filings to falling wage security, and hear the real stories behind the statistics: Maria in retail and rideshare, Jamal in security and IT, and Carla balancing office work with weekend catering. We unpack how inflation, credit rates, and unstable schedules have made side income essential—and how this new class of workers has learned to treat time like money. They plan their weeks like businesses: tracking margins, protecting sleep, and managing taxes on every dollar. The takeaway is clear: the side hustle isn’t on the side anymore. It’s the scaffolding holding the middle class together. Learn more about your ad choices. Visit megaphone.fm/adchoices
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