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Explore turning points, everyday joys and unexpected challenges after financial independence or retirement, with the date and original source for each account.

Age
Wealth
Years
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61–67 of 67 posts

Gardening replaces the paid day she could not let go

2018Recalled in 2023

Life at the time

  • She worked one day each week for a friend’s company.
  • Rental income and the small job covered living costs without investment withdrawals.

How it felt

  • Even a single working day brought the old Sunday dread. “Sunday night feeling”
  • Declining extra income felt difficult despite financial independence. “struggled with turning down money”

A travel fund makes room to enjoy retirement

Oct 2017 · Year 2Interview snapshot · published 2017

Life at the time

  • Two years after retirement, the couple took frequent trips and spent substantial time at their mountain cabin.

How it felt

  • Keeping a separate travel fund helped him enjoy spending on experiences. “fun to figure out how to spend it.”

A trial in Mexico grew into a home and a different health routine

2017Recalled in 2022

Life at the time

  • Two snowbird seasons gave them spending records.
  • They moved full-time to Mexico and budgeted for local care.

How it felt

  • Tracking costs gave them confidence in the move. “we knew”
  • They accepted leaving Ontario’s familiar coverage. “lose our OHIP coverage”

He kept accepting offers. Real retirement began when he started declining them.

2014Recalled in 2020

Life at the time

  • A final visit with his father was followed by transition work and coaching.
  • Consulting filled much of the first eighteen months.

How it felt

  • His own interests kept being postponed. “almost nothing that I wanted”
  • He realized appealing requests could still be poor fits. “not at all what I had expected”

A search for community met an uncomfortable market lesson

2008

Life at the time

  • Their diversified portfolio lost 23% on paper.
  • The decline drove a decision to live in Mexico full-time.

How it felt

  • The loss felt large enough to change their lives. “life-changing”
  • They regretted not discovering a more conservative approach sooner. “worry about not having enough”

A market crash threatened the journey; a seaside home later felt enough

2008Recalled in 2023

Life at the time

  • His portfolio fell toward its starting value during the financial crisis.
  • He updated his résumé in case travel became unaffordable.

How it felt

  • The losses felt like a personal crisis. “gut-wrenching”
  • He feared the traveling life would collapse. “collapse in ruins”

A search for community met an uncomfortable market lesson

2002

Life at the time

  • Kevin left Allegro; Erin had retrained in massage.
  • Occasional consulting and massage replaced conventional careers.

How it felt

  • More time together proved pleasantly compatible. “feel blessed”
  • Their priorities no longer aligned with many working friends. “out-of-synch”

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