Catching Up to FI

Why Your Financial Plan Will Fail (It's Not the Math) | Dan Haylett | 192

68 snips
Jan 25, 2026
Guest
Dan Haylett
Dan Haylett, a UK financial planner and author focused on retirement psychology, challenges the old retire-and-fade script. He explains why retirement is a human problem before it’s a math problem. He reframes risk as lost experiences, maps the three phases of later life, and urges structure, curiosity, and meaningful spending over spreadsheet comfort.
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INSIGHT

Retirement Is A Human Problem

  • Retirement is primarily a human problem, not a math problem, because emotional and identity shifts drive outcomes.
  • Dan Haylett says a perfect spreadsheet can still fail if people lack purpose and structure after work.
ANECDOTE

Leaving Corporate For Purpose

  • Dan left a high-paying corporate role at 35 because it felt hollow and unimpactful, prompting a career change.
  • He retrained into financial planning to align work with purpose and human impact.
INSIGHT

Old Retirement Script Is Outdated

  • Modern retirement assumptions are outdated: longer lifespans, knowledge work, and defined-contribution plans change the stakes.
  • Identity tied to work and higher aspirations create a money-meaning conflict most grandparents didn't face.
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