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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
Posts
71–80 of 95 posts

He won his freedom—and ran out of goals.

2020 · Year 4

Life at the time

  • Reconsidered a proposed two-home arrangement before buying the properties.
  • Absorbed a sharp fall in unexpected post-retirement income while keeping spending restrained.

How it felt

  • The pandemic exposed how quickly the travel assumptions behind the plan could fail. “the entire travel industry would just go poof overnight”
  • Did not want the stress of managing that arrangement under pressure. “I don’t think I would be comfortable with that.”

Semi-retirement still includes a business

Nov 2019Interview snapshot · published 2019

Life at the time

  • As a staffing-company co-owner, he worked to his own schedule and avoided the office commute when possible.

How it felt

  • He described an excellent work-life balance, while also acknowledging some struggle with being semi-retired. “I’m kind of semi-retired and I’m struggling with that a bit.”

He protected the weekends—and discovered he wanted to protect the weekdays too.

Oct 2019Recalled in 2020

Life at the time

  • House projects and motorcycling filled the first three months.
  • He spent weekdays at home after years of commuting across states.

How it felt

  • The transition felt unusually smooth. “seamless”
  • He barely thought about his old job. “My newfound freedom”

He left the office, but a screen could still consume the day.

Sep 2019Recalled in 2020

Life at the time

  • He kept his longstanding early-rising routine after leaving the office.
  • A side business continued while accrued leave extended his pay.

How it felt

  • He felt ready and positive about leaving. “It’s been awesome”
  • Keeping balance was harder than finding things to do. “struggled with balance/routine”

He slept through the first adjustment. Later, even Sunday evenings felt free.

Jul 2019 · Year 4

Life at the time

  • Family dinners, workshop projects and occasional delivery work filled his days.
  • His wife crafted and made things for their granddaughters.

How it felt

  • They enjoyed choosing how to spend their time. “no demands on my time”
  • Both still missed some school colleagues. “miss some of our coworkers”

Flying and service gave an unexpectedly early exit direction

May 2019

Life at the time

  • Runs, voluntary work and legislative meetings structured days.
  • Flying and short road trips supplied recreation.

How it felt

  • He enjoyed choosing his own schedule. “doing what I want”
  • The speed of passing retirement time surprised him. “time passes”

He could choose his projects. Their shared adventures were still on hold.

Apr 2019 · Year 0.75

Life at the time

  • Writing, pro bono consulting and household tasks shaped his days.
  • Travel and an overseas move remained plans for after his wife stopped working.

How it felt

  • Creative interests were returning. “I feel like I’m in limbo”
  • He felt guilty about adventures she could not share. “a part of me feels guilty”

Freedom came easily. Finding nearby friends took more work.

Mar 2019 · Year 6

Life at the time

  • Home repairs and helping relatives filled parts of the week.
  • His wife pursued yoga, food preserving and fiber arts.

How it felt

  • New friendships required deliberate effort. “Still working on it.”
  • Formal volunteer roles felt too much like work. “Working as a volunteer is still working.”

The money was enough. Learning to spend it took longer.

Mar 2019 · Year 1

Life at the time

  • Slept, cycled, read and took music lessons as a loose routine emerged.
  • Turned down job offers and spent less than the planned allowance.

How it felt

  • Initially felt unsure how to use the time. “I didn’t know what to do with myself, but I got plenty of sleep”
  • Became interested in selected creative work for engagement rather than simply income. “it’s not about the money anymore, it’s about the experience.”

A pilot retires as his wife considers more work

Jan 2019Interview snapshot · published 2019

Life at the time

  • Newly retired from the Air Force, he enjoyed recreational flying and a relaxed routine while his wife considered returning to full-time nursing.

How it felt

  • He liked the improved balance and was still anticipating how an empty nest and different work schedules would change it. “Since I retired, I wear a straw hat and Hawaiian shirts.”

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