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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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81–88 of 88 posts

Retiring from first careers opens a life overseas

Nov 2013Interview snapshot · published 2020-08

Life at the time

  • After early retirement from their first jobs, the couple moved overseas to combine continued professional engagement with travel, arts and entertainment.

How it felt

  • They enjoyed the mix of work and leisure and were unsure that staying home without work would suit them. “We moved overseas so that we can be professionally engaged”

They imagined months away. Home, friends and flexible work changed the plan.

Jun 2012

Life at the time

  • They had moved from Denver to a Florida condo.
  • Steve reduced work to a few transition-consulting hours as their sons prepared for college.

How it felt

  • They loved their new home and anticipated longer journeys. “we love it”
  • Raising their sons was their proudest accomplishment. “our greatest accomplishment”

A search for community met an uncomfortable market lesson

2008

Life at the time

  • Their diversified portfolio lost 23% on paper.
  • The decline drove a decision to live in Mexico full-time.

How it felt

  • The loss felt large enough to change their lives. “life-changing”
  • They regretted not discovering a more conservative approach sooner. “worry about not having enough”

A market crash threatened the journey; a seaside home later felt enough

2008Recalled in 2023

Life at the time

  • His portfolio fell toward its starting value during the financial crisis.
  • He updated his résumé in case travel became unaffordable.

How it felt

  • The losses felt like a personal crisis. “gut-wrenching”
  • He feared the traveling life would collapse. “collapse in ruins”

A home fit for a while. Traveling light fit better later.

May 2007 · Year 23

Life at the time

  • They combined a country home near Buenos Aires with continuing travel.
  • Paul made wine with two Argentine friends.

How it felt

  • They felt fortunate and expressed no regrets. “We feel fortunate”
  • Vicki wished she could be in several places to be present for loved ones. “wanting to be in more than one place”

A long retirement became a community life, with room for changing health.

2003Recalled in 2019

Life at the time

  • Volunteer work and unfinished chores filled his first year.
  • Once his wife retired, they spent two months visiting their children.

How it felt

  • Leaving emotionally wearing work brought relief. “For me, I felt relief.”
  • The extended family trip helped the transition feel natural. “felt very natural”

A search for community met an uncomfortable market lesson

2002

Life at the time

  • Kevin left Allegro; Erin had retrained in massage.
  • Occasional consulting and massage replaced conventional careers.

How it felt

  • More time together proved pleasantly compatible. “feel blessed”
  • Their priorities no longer aligned with many working friends. “out-of-synch”

They left intense work for island time, then spent decades exploring.

Jan 1991Recalled in 2022

Life at the time

  • They spent the first months on Caribbean islands.
  • A radical change of surroundings replaced long workweeks.

How it felt

  • They had to release accumulated intensity. “learning to slow down”
  • Family resistance made the choice emotionally harder for Akaisha. “wasn’t easy for her”

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