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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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41–50 of 65 posts

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

Sep 2019Recalled in 2020

“It’s been awesome, purely!”

ESI Retiree 24Read original post (opens in a new tab)

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”
RoutinePartnersFreedom
ESI Retiree 24
Read original postesimoney.com

Permission to enjoy retirement takes time

Jul 2019Interview snapshot · published 2019

“Felt somewhat guilty and antsy, even with plenty of things to keep me busy.”

ESI Millionaire 138Read original post (opens in a new tab)

Life at the time

  • After leaving a second consulting career, he did some oil prospecting and served on a school-board finance committee while becoming more involved in church.

How it felt

  • It took nearly two years to feel comfortable, with guilt possibly connected to his wife still working. “It’s taken me the better part of two years to get really comfortable with retirement.”
IdentityPartnersPurpose
ESI Millionaire 138
Read original postesimoney.com

Loving freedom and still feeling unsettled

Jun 2019Interview snapshot · published 2019

“I do feel unsettled at times.”

ESI Retiree 14Read original post (opens in a new tab)

Life at the time

  • She attended classes and theater, met friends and learned canasta, while her husband's work schedule limited longer trips.

How it felt

  • She loved not working but sometimes felt uncertain about purpose; talking through the transition had helped. “I do feel unsettled at times.”
IdentityPartnersCuriosity
ESI Retiree 14
Read original postesimoney.com

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

Apr 2019 · Year 0.75

“I feel like I’m in limbo”

ESI Retiree 5Read original post (opens in a new tab)

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”
PartnersCreativityFreedom
ESI Retiree 5
Read original postesimoney.com

Losing the job was painful. Life afterward was mostly good—and sometimes boring.

Apr 2019 · Year 4

“My wife is the opposite — she loves not working and has no interest in going back.”

ESI Retiree 4Read original post (opens in a new tab)

Life at the time

  • Gym visits, friends and outings filled a relaxed week.
  • The couple regularly visited their second home in the Southwest.

How it felt

  • He sometimes felt bored or obliged to work. “there are days I’m just bored”
  • His wife remained content without another job. “she loves not working”
IdentityRoutinePartners
ESI Retiree 4
Read original postesimoney.com

The bucket list did not run itself. Neither did the friendships.

Apr 2019 · Year 3

“many of our friends are still quite busy with their own jobs (and kids) and are not as free as we are to make plans.”

MrFireStationRead original post (opens in a new tab)

Life at the time

  • Regularly initiated invitations and renewed friendships from earlier stages of life.
  • Kept separate morning activities and shared dates, volunteering and later plans.

How it felt

  • Recognized that a social life needed someone to make arrangements. “designated planners”
  • Made reaching out to other people an almost daily habit. “I try to reach out to someone almost every day”
FriendsPartners
MrFireStation
Read original postmrfirestation.com

A layoff became a travel business—and time to help his parents.

Apr 2019Recalled in 2023

“I guess I wasn’t happy I didn’t get to leave on my terms”

ESI Retiree 51Read original post (opens in a new tab)

Life at the time

  • An unexpected layoff ended his treasury career.
  • He began building a travel agency around an existing interest.

How it felt

  • He disliked losing control of the departure date. “wasn’t happy”
  • Leaving an unfulfilling job opened a more enjoyable direction. “something now I enjoy”
WorkFamilyPartners
ESI Retiree 51
Read original postesimoney.com

Making time for family after a consuming career

Feb 2019Interview snapshot · published 2019

“I spend a lot of time with my wife and kids now and enjoy it immensely.”

ESI Millionaire 116Read original post (opens in a new tab)

Life at the time

  • Outside executive employment, he spent more time with his wife and children while pursuing angel investments, walks, runs and yoga.

How it felt

  • He regretted earlier absences and described family and community involvement as part of his personal growth. “enjoy it immensely”
FamilyPurposePartners
ESI Millionaire 116
Read original postesimoney.com

A pilot retires as his wife considers more work

Jan 2019Interview snapshot · published 2019

“Since I retired, I wear a straw hat and Hawaiian shirts.”

ESI Millionaire 109Read original post (opens in a new tab)

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.”
PartnersChangeFreedom
ESI Millionaire 109
Read original postesimoney.com

Sharing retirement meant renegotiating the house, the chores and the conversation.

2019Recalled in 2023

“Pure joy, gratitude, and freedom.”

ESI Retiree 45Read original post (opens in a new tab)

Life at the time

  • The second departure put both partners at home full time.
  • Separate offices replaced one shared workspace.

How it felt

  • They welcomed the freedom from employer schedules. “Pure joy, gratitude, and freedom”
  • Dividing chores and space required negotiation. “re-negotiate”
PartnersFamilyFreedom
ESI Retiree 45
Read original postesimoney.com

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