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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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21–30 of 194 posts

Monday golf with Dad becomes non-negotiable

Mar 2026Interview snapshot · published 2026-07

Life at the time

  • Working three days a week in municipal projects left four-day weekends and a standing Monday golf game with his father.

How it felt

  • He felt the balance was finally right after full-time work had repeatedly displaced family occasions. “this is a non-negotiable”

He retired with $2.7m. Three years later, he wanted back in.

Feb 2026 · Year 3

Life at the time

  • Accepted another engineering job after three years away.
  • Hoped the lower-paid role would preserve flexibility; that outcome had not yet been tested.

How it felt

  • Wanted challenge and mentoring alongside concerns about higher spending. “I want a new challenge somehow.”
  • Valued the family experiences during the break and did not regret taking it. “I do not regret having a 3 year sabbatical”

He left surgery for adventure. Grandchildren changed the destination.

Feb 2026 · Year 9

Life at the time

  • Reduced travel and sold an underused RV as grandchildren became a bigger priority.
  • Continued writing, coaching and making music alongside family time.

How it felt

  • Accepted that a satisfying retirement could change shape over time. “Your plans will evolve, so just go with it.”
  • Did not miss the RV’s upkeep. “I certainly don’t miss all the upkeep it took.”

A prepared exit opens time for family, theatre and service

Jan 2026 · Year 1

Life at the time

  • His year included months with parents and a meditation retreat.
  • He wrote plays, acted, traveled by RV and expanded education volunteering.

How it felt

  • He reported no regret about retiring. “I cannot think of a single regret”
  • Helping children through a nonprofit was especially fulfilling. “one of the most fulfilling parts”

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

Jan 2026Recalled in 2026

Life at the time

  • He left corporate employment at year-end.
  • The first months went into research and planning.

How it felt

  • Losing daily involvement with colleagues hurt. “left out of the team”
  • He gradually distinguished missing people from missing the company. “It got easier”

A negotiated step down follows the children's calendar

Jan 2026Interview snapshot · published 2026-03

Life at the time

  • A self-demotion gave him a flexible work schedule aligned with school hours, holidays and the children's needs.

How it felt

  • He called the arrangement a form of semi-retirement and remained unsure what the next stage would be while his wife enjoyed working. “I’m sorta semi-retired now.”

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.”

The layoff ended the waiting. Retirement became an experiment.

Dec 2025

Life at the time

  • Taught a college course and brought former colleagues into a student discussion.
  • Traveled with friends and family, and attended a first FI/RE meetup.

How it felt

  • Enjoyed sharing professional experience with students. “I enjoyed bringing industry experience to college students.”
  • Disliked the administration involved in managing a class of 250. “I didn't enjoy the administrative overhead”

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

Oct 2025 · Year 5

Life at the time

  • Signed an apartment lease in upstate New York and bought a car.
  • Planned to keep traveling while using the apartment as a home base.

How it felt

  • Missing ordinary time with her partner’s family helped prompt the move. “the FOMO of not being around my Partner’s family got to us.”
  • Was happy with the decision, despite the added cost of setting up a home. “But I’m happy with our decision”

Learning to retire, then learning to leave a beloved project

Sep 2025

Life at the time

  • She paused blogging to support her son after a serious cycling accident.
  • After returning home, she announced the end of regular blog writing.

How it felt

  • She felt grateful for her son’s recovery and support around him. “ready for something new”
  • Unexpectedly deep blogging friendships made the decade feel valuable. “deep and lasting friendships”

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