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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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11–20 of 541 posts

They drove away from their old life with doubts. Six years later, the road still appealed.

Sep 2026 · Year 6

Life at the time

  • Extended road trips explored different parts of the United States.
  • Travel and visits with relatives replaced the old work-centered calendar.

How it felt

  • He reported substantially less stress. “much less stress”
  • New places and conversations kept the experience enjoyable. “a fun journey”

The portfolio soared. Feeling free took much longer.

Sep 2026 · Year 5

Life at the time

  • Pursued language learning, art and small consulting projects.
  • Became more willing to pay for comfort and convenience while traveling.

How it felt

  • Recognized that leaving work had not automatically ended anxiety. “Anxiety doesn't end at retirement”
  • Felt his identity had broadened beyond being a programmer. “I feel like a more complete human now than I ever was”

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.”

Less stress made room for more life. Choosing the right challenges took longer.

Aug 2026 · Year 2

Life at the time

  • She was coaching, writing and running university programs.
  • Language learning supported a future move to Portugal, still in preparation.

How it felt

  • Building a new university initiative felt energizing. “I haven’t figured out the balance yet”
  • She was still working out which commitments were meaningful and sustainable. “the energy that starting a new job used to give me”

Missing the team gave way to building—and a new need for boundaries

Aug 2026Recalled in 2026

Life at the time

  • Product development began in May.
  • School drop-offs and activities fitted around chosen work.

How it felt

  • Making things felt enjoyable again. “building is fun again”
  • Launch sprints threatened the balanced life he wanted. “one-dimensional life”

A travel sabbatical became a flexible working life

Jul 2026 · Year 3

Life at the time

  • Consults for one client at a time, taking breaks and testing business ideas between engagements.
  • Tried renting out the apartment for three months while travelling; the administration outweighed the appeal.

How it felt

  • Feels reassured that returning to work remains possible and would not mean failure. “I now know that I can return to work”
  • Values deciding when to take a break more than the original idea of never working again. “being able to decide when I take a break”

The adventures changed as his body did. He kept finding another project.

Jul 2026 · Year 15

Life at the time

  • Tried successive projects, including software, outdoor goals and a memoir.
  • A software effort brought back long hours at a desk.

How it felt

  • Found some skills rusty when he returned to software work. “I was out of practice.”
  • Saw mistakes and completed projects as part of an ongoing search for worthwhile effort. “My answers were not always optimal, but they were educational.”

The portfolio cleared the target. Purpose did not arrive with it.

Jul 2026 · Year 2

Life at the time

  • Built a week around book clubs, exercise, volunteering and family.
  • Made investment changes in response to financial anxiety.

How it felt

  • Appreciated a rhythm that left room to choose, though loneliness remained. “We've settled into a rhythm, though not a schedule”
  • Wanted to set the next direction personally instead of taking it from another job. “I'm determined the direction will be set by me”

A year without work proved the exit was real.

Jul 2026 · Year 1

Life at the time

  • Returned to employment after a year away.
  • Considered a partner’s wish to retire together and keeping professional skills current.

How it felt

  • The trial had increased confidence in the option to leave work. “That freedom is a wild feeling.”
  • Was evaluating employment week by week rather than assuming a long commitment. “Right now I'm taking employment week by week”

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