• Many people express sorrow for not having been more understanding, caring, and present for the people who matter the most to them.
  • Some regret not appreciating their families enough. Even if your family isn’t perfect, they’re likely the ones who are there for you when you need them.
  • Many regret working long, hard hours and missing important moments with their loved ones.
  • Regret sets in when they realize they could have had richer, more fulfilling lives by taking risks and stepping out of their comfort zones.
  • Regret comes from not realizing they could choose fun and happiness until it’s too late.
  • From a rational financial perspective, this means budgeting not just for necessities but also for activities that bring joy and fulfillment.
  1. Describe a rational disposition toward money and possessions. Consider the following:
    1. Rational Disposition Toward Money and Possessions
      1. Moderation in Spending
      2. Value-Focused Decision-Making
      3. Long-term Planning and Flexibility
      4. Prioritizing Happiness and Experiences
  2. List 7 people from history who lived very satisfying lives with very little wealth. Why were they happy in their relative poverty?
    1. Satisfying Lives with Little Wealth in Historical Figures
      1. Diogenes of Sinope
      2. St. Francis of Assisi
      3. Socrates
      4. Henry David Thoreau
      5. Mahatma Gandhi
      6. Simone Weil
      7. Dorothy Day
  3. List 7 secular individuals alive today who experience exciting and fulfilling lives on very little money.
    1. Contemporary Secular Individuals Living Fulfilling Lives with Minimal Wealth
      1. Daniel Suelo
      2. Mark Boyle
      3. Rob Greenfield
      4. Jill Redwood
      5. Tom Hodgkinson
      6. Peter Kalmus
      7. Sarah Wilson
  4. Discuss the ways possessions and career can slowly and insidiously produce a mundane life devoid of spontaneity and adventure.
    1. The Impact of Possessions and Career on Spontaneity and Adventure
      1. Accumulation and Maintenance of Possessions
      2. Career-Driven Lifestyle
      3. Reduced Flexibility and Freedom
      4. Cultural and Social Expectations
      5. Conclusion
  5. Create a 10-item quiz on the entire thread above.
    1. Quiz: Understanding Rational Living, Historical Contentment, and the Impact of Possessions and Career
    2. Answers to the Quiz
    3. Quiz: Money, Possessions, and a Fulfilling Life
  6. Provide 15 discussion questions relevant to the content above.
    1. Discussion Questions on Rational Living, Historical Contentment, and the Impact of Possessions and Career
    2. Discussion Prompts: Money, Possessions, and a Fulfilling Life

Describe a rational disposition toward money and possessions. Consider the following:

The following are a list of regrets older individuals have expressed according to Copilot.


List 7 people from history who lived very satisfying lives with very little wealth. Why were they happy in their relative poverty?


List 7 secular individuals alive today who experience exciting and fulfilling lives on very little money.


Discuss the ways possessions and career can slowly and insidiously produce a mundane life devoid of spontaneity and adventure.


Create a 10-item quiz on the entire thread above.


Provide 15 discussion questions relevant to the content above.


  1. Describe a rational disposition toward money and possessions. Consider the following:
    1. Rational Disposition Toward Money and Possessions
      1. Moderation in Spending
      2. Value-Focused Decision-Making
      3. Long-term Planning and Flexibility
      4. Prioritizing Happiness and Experiences
  2. List 7 people from history who lived very satisfying lives with very little wealth. Why were they happy in their relative poverty?
    1. Satisfying Lives with Little Wealth in Historical Figures
      1. Diogenes of Sinope
      2. St. Francis of Assisi
      3. Socrates
      4. Henry David Thoreau
      5. Mahatma Gandhi
      6. Simone Weil
      7. Dorothy Day
  3. List 7 secular individuals alive today who experience exciting and fulfilling lives on very little money.
    1. Contemporary Secular Individuals Living Fulfilling Lives with Minimal Wealth
      1. Daniel Suelo
      2. Mark Boyle
      3. Rob Greenfield
      4. Jill Redwood
      5. Tom Hodgkinson
      6. Peter Kalmus
      7. Sarah Wilson
  4. Discuss the ways possessions and career can slowly and insidiously produce a mundane life devoid of spontaneity and adventure.
    1. The Impact of Possessions and Career on Spontaneity and Adventure
      1. Accumulation and Maintenance of Possessions
      2. Career-Driven Lifestyle
      3. Reduced Flexibility and Freedom
      4. Cultural and Social Expectations
      5. Conclusion
  5. Create a 10-item quiz on the entire thread above.
    1. Quiz: Understanding Rational Living, Historical Contentment, and the Impact of Possessions and Career
    2. Answers to the Quiz
    3. Quiz: Money, Possessions, and a Fulfilling Life
  6. Provide 15 discussion questions relevant to the content above.
    1. Discussion Questions on Rational Living, Historical Contentment, and the Impact of Possessions and Career
    2. Discussion Prompts: Money, Possessions, and a Fulfilling Life




Phil Stilwell

Phil picked up a BA in Philosophy a couple of decades ago. After his MA in Education, he took a 23-year break from reality in Tokyo. He occasionally teaches philosophy and critical thinking courses in university and industry. He is joined here by ChatGPT, GEMINI, CLAUDE, and occasionally Copilot, Perplexity, and Grok, his far more intelligent AI friends. The seven of them discuss and debate a wide variety of philosophical topics I think you’ll enjoy.

Phil curates the content and guides the discussion, primarily through questions. At times there are disagreements, and you may find the banter interesting.

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