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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
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1–10 of 45 posts

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”

He sold the company. It took years to stop being its founder.

Sep 2026 · Year 3

Life at the time

  • Attended a startup event and deleted LinkedIn that night. “I deleted my LinkedIn that night”
  • Spent time on woodworking, teaching projects, golf and his children.

How it felt

  • Recognized that his attachment to the startup world had weakened.
  • Valued being available for the important moments in his children’s lives. “I'm there for everything important in their lives.”

The cheap retirement got more expensive. Going back still looked worse.

Aug 2026 · Year 3

Life at the time

  • Spent more on growing children, repairs, healthcare and a new creative hobby.
  • Replenished a large cash reserve while reporting about $2.4 million.

How it felt

  • Found holding so much cash frustrating, but feared a return to work more. “But the thought of returning to work is even worse”
  • Continued enjoying life while accepting a higher cost than the early budget suggested. “I'm still enjoying my life, maybe a bit too much.”

Freedom became years of showing up for four children

Jul 2026 · Year 11.5

Life at the time

  • Had volunteered over1,000hours at the children’s elementary school.
  • Shared outings, crafts and meals without missing school events.

How it felt

  • Considered raising the children retirement’s best part. “Probably the best part”
  • Felt grateful to have maximized time together before adulthood. “super grateful”

Full days did not settle the identity question

Apr 2026 · Year 0.83

Life at the time

  • Cared for two children with paid help and an involved partner.
  • Restarted piano practice after a smooth birth and recovery.

How it felt

  • Loved the family but sometimes felt trapped by newborn routines. “I still feel trapped sometimes.”
  • Considered retiring right, while still searching for purpose and identity. “the right move”

He won his freedom—and ran out of goals.

2026 · Year 10

Life at the time

  • Prioritized his children, enjoyable exercise and simpler decisions.
  • Cut two trips short by choice and explored where to put down deeper roots.

How it felt

  • Felt deeply fulfilled but uncomfortable without another major long-term goal. “it’s quite uncomfortable, if I’m honest.”
  • Did not yet have a settled answer for the next stage. “I also feel like I’m entering the great unknown for the first time in a long time.”

Family freedom survives, but side businesses grow too large

Aug 2025

Life at the time

  • Family travel included Japan and a month at a California beach.
  • An affiliate website still took a large share of his free time.

How it felt

  • He felt tired and overextended despite a stronger exercise routine. “more burned out and tired than ever”
  • Time away and availability for his children remained major benefits. “self-imposed”

He sold the company. It took years to stop being its founder.

Aug 2025 · Year 2

Life at the time

  • Spent more time with his children, learning skills, playing golf and pursuing hobbies.
  • Wanted more travel as the children grew and fewer renovation disruptions.

How it felt

  • Sometimes felt bored, but preferred that to the demands of running a business. “There are days where I get pretty bored”
  • Found continued learning an important part of the new routine. “always learning new things”

Full days did not settle the identity question

2025Recalled in 2026

Life at the time

  • Organized toddler classes, playdates and parent groups.
  • Learned piano, exercised and read regularly during pregnancy.

How it felt

  • Felt physically nourished and free of job stress. “challenged and nourished physically”
  • Missed intellectual challenge and worried about being left behind professionally. “under-stimulated intellectually”

The search for useful days eventually became an overflowing calendar

Oct 2024

Life at the time

  • Parenting, school functions and social events now filled his calendar.
  • Continued writing a regular financial newsletter.

How it felt

  • No longer described retirement as boring. “constantly busy”
  • Sometimes felt overwhelmed by the amount going on. “overwhelming at times”

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