Keen On America

The Unluckiest Generation: Confessions of a Millennial

Sep 16, 2025
Charlie Wells, a vibrant Bloomberg reporter and author of What Happened to Millennials, dives into the complexities of the millennial experience. He argues that millennials are 31% wealthier than boomers were at the same age, challenging the notion of them being the 'unluckiest generation.' Technology, he asserts, has merely amplified age-old struggles, making them visible but not unique. Through personal narratives, he highlights the loneliness and identity crises shaped by social media, while advocating for authentic connections beyond screens.
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INSIGHT

Recessions Scar Careers Long-Term

  • Graduating into a recession can suppress lifetime earnings because early low-pay roles are hard to overcome.
  • Millennials faced high youth unemployment after the 2008 crisis, shaping career trajectories for many.
INSIGHT

Data Upsets The 'Unlucky Generation' Story

  • Millennial narrative changed as underlying data shifted; millennials are now about 31% wealthier than boomers were at the same age on average.
  • However, wealth inequality within millennials is much wider, revealing a split between very successful and struggling cohorts.
ANECDOTE

A Subject Whose Father Died In 9/11

  • Charlie interviewed five millennials and one had a father who died in 9/11, showing deeply personal consequences for some.
  • He contrasts direct victims' long-term trauma with broader societal witness of the event.
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