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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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31–40 of 194 posts

Family freedom survives, but side businesses grow too large

Aug 2025

Life at the time

  • Family travel included Japan and a month at a California beach.
  • An affiliate website still took a large share of his free time.

How it felt

  • He felt tired and overextended despite a stronger exercise routine. “more burned out and tired than ever”
  • Time away and availability for his children remained major benefits. “self-imposed”

He sold the company. It took years to stop being its founder.

Aug 2025 · Year 2

Life at the time

  • Spent more time with his children, learning skills, playing golf and pursuing hobbies.
  • Wanted more travel as the children grew and fewer renovation disruptions.

How it felt

  • Sometimes felt bored, but preferred that to the demands of running a business. “There are days where I get pretty bored”
  • Found continued learning an important part of the new routine. “always learning new things”

Retirement gave him time. A diagnosis showed why that mattered.

Jul 2025

Life at the time

  • A serious diagnosis redirected attention toward health and family.
  • Asked for help continuing community resources while priorities changed.

How it felt

  • Valued being able to direct time toward urgent personal needs. “Your life SHOULD be your own.”
  • Had already found retirement busy; leaving work did not mean an empty calendar. “I have been busier now then before I retired.”

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

May 2025 · Year 1

Life at the time

  • Workouts, part-time teaching, writing and relaxed afternoons shaped her days.
  • She deliberately arranged gym sessions, walks and coffees with friends.

How it felt

  • She felt calmer and had more energy for her children. “I am better rested”
  • She missed the automatic contact and shared problem-solving of work. “I miss having co-workers”

The freedom was immediate; chosen structure came later

May 2025

Life at the time

  • Caught up on household projects and spent more time with extended family.
  • Dealt with paperwork and reimbursements during the insurance transition.

How it felt

  • Felt detached from unfinished work almost immediately. “I’ve completely detached”
  • Found it freeing to spend within the planned budget instead of obsessing over portfolio size. “It’s been freeing.”

A prepared exit opens time for family, theatre and service

Apr 2025

Life at the time

  • He was staying in India after his January retirement.
  • He reviewed his portfolio and carried out tax-related trades during volatility.

How it felt

  • He had not expected the plan to be tested so quickly. “not hoping to have it tested so soon”
  • He reported feeling unconcerned about missing some future market upside. “I am not concerned at all”

He escaped the night calls. Then had to give himself permission to relax.

Apr 2025 · Year 1

Life at the time

  • Had more family dinners, exercise and time to build a computer with a child.
  • Left space in the first year while rebuilding structure and identity.

How it felt

  • Deliberately allowed boredom instead of rushing into another packed calendar. “I gave myself a year to be purposefully bored”
  • Valued the time gained from leaving work. “I love the time.”

He escaped Sunday-night dread. A decade later, even freedom needed downtime.

Mar 2025

Life at the time

  • Combined family travel, tax preparation and plans for more trips.
  • Alternated stretches at home with further adventures.

How it felt

  • Wanted to explore while travel remained enjoyable. “We can always rest when we’re ‘old’!”
  • Also valued time at home to rest and catch up with family and friends. “Some weeks we’re here at home in Raleigh relaxing and catching up with family and friends.”

Family plans stop competing with work commitments

Feb 2025Interview snapshot · published 2025-04

Life at the time

  • After leaving salaried work, the couple's days filled with their children's activities and physical activity.

How it felt

  • They valued freedom from scheduling conflicts, while keeping travel and a possible future work or volunteer role open. “not have to be worried about conflicts between work and family plans.”

The long commute gives way to summers with the children

Jan 2025Interview snapshot · published 2025-04

Life at the time

  • After leaving daily work in June 2023, he spent summers at a mountain home, played golf and coached his children's sports.

How it felt

  • He enjoyed the new balance while continuing to manage two industrial properties. “I spend most of my time with my young kids.”

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