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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.

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She escaped the office. Then burned out planning the next trip.

Oct 2026 · Year 6

Life at the time

  • Combined an upstate New York home with nearby travel and several international trips. “I think we’ve settled into it nicely.”
  • Renewed the lease through at least May 2027 while planning additional travel.

How it felt

  • Felt comfortably settled after more than a year with a home base. “I think we’ve settled into it nicely.”
  • Enjoyed discovering a new shared routine after her partner retired.

She sold the house—and the identity built around it.

Oct 2026October 5, 2026 essay

Life at the time

  • Lived aboard a sailboat with her partner in less than 500 square feet.
  • Chose experiences over possessions while learning the routines and uncertainty of life at sea.

How it felt

  • Felt relief after voicing the decision to sell a home tied closely to memory and identity. “Who am I?”
  • Began separating self-worth from titles, recognition and constant accomplishment. “I chose to strip away the external validation loop”

Within months, slower days began to feel normal

Sep 2026

Life at the time

  • Had taken a three-week Newfoundland retirement road trip.
  • Averaged over 10,000 steps daily, golfed weekly and cycled over 100 kilometres a week.

How it felt

  • Enjoyed having time to think and act on his own schedule. “time moves differently”
  • Was surprised that the household worried less about money. “we don’t worry about money”

Financial safety opened into a brighter home and deeper friendships

Sep 2026

Life at the time

  • She renovated a sunnier home.
  • New friendships joined reading, yoga and walks.

How it felt

  • The move brought joy. “real joy”
  • She valued room to grieve her parents. “grateful that I can feel”

The imagined transformation never came. Ordinary life became more valuable.

Sep 2026 · Year 5

Life at the time

  • Family difficulties and a communal project took substantial time.
  • Writing, hiking and home renovation happened, while many planned hobbies did not.

How it felt

  • He valued ordinary moments with his wife. “It feels like heaven”
  • Helping others made him feel useful despite a difficult year. “it made me feel useful”

Small pleasures made the first weeks rich. Years later, home still competed with adventure.

Sep 2026

Life at the time

  • Traveled in Nepal and took a scenic flight near Everest.
  • Looked forward to returning home for family birthdays.

How it felt

  • Wanted to be home again without dismissing the trip. “My nose is turned firmly towards home now”
  • Described the holiday positively; adventure and familiar routines both appealed. “It’s been a very good holiday.”

Freedom once meant the road. Later, it included a growing family.

Sep 2026

Life at the time

  • He shared life with his partner and daughter.
  • Personal websites and outdoor activities filled free time.

How it felt

  • Parenthood had become a welcome change. “pretty special”
  • Making connections in Lisbon felt easy. “Making real connections”

She escaped the office. Then burned out planning the next trip.

Sep 2026

Life at the time

  • Helped with a week of detective games her mother created for a six-year-old.
  • Continued writing, reviewing and learning despite falling blog traffic.

How it felt

  • Did not need creative interests to earn enough to support her life. “receiving money for my creativity was never a goal of mine.”
  • Valued making things for the enjoyment they brought her and other people. “These days, I bring joy to myself and others with my creativity.”

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