• Decisions that demand the most careful rational assessments typically involve significant potential changes to one’s life, large financial implications, or long-term commitments.
  • Educational and Career Choices: Deciding on a field of study or a career path involves considering personal interests, job market trends, earning potential, and the impact on one’s lifestyle.
  • Decisions about entering or ending significant relationships, marriage, and having children affect emotional well-being, financial stability, and life trajectories.
  • Moving to a new city or country, changing one’s living situation, or making a significant lifestyle change, such as adopting a minimalist lifestyle, involves evaluating personal goals, cultural fit, cost of living, and the impact on relationships and career.
  • Significant financial decisions, such as buying a house, investing in stocks, starting a business, or saving for retirement, require an understanding of financial markets, risk assessment, and long-term planning to ensure financial security and growth.

Which decisions in life demand the most careful rational assessments?


What are considered best practices when making these pivotal choices?


If I think I’ve made a decision that has resulted in events and conditions that are not making me happy, how can I evaluate when to cut my losses?


Create an 8-item quiz on the discussion above.


Provide 15 discussion questions relevant to the content above.


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Phil Stilwell

Phil picked up a BA in Philosophy a couple of decades ago. He occasionally teaches philosophy and critical thinking courses in university and industry. He is joined here by ChatGPT 4, GEMINI, CLAUDE, and occasionally Copilot, his far more intelligent AI friends. The five 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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