• “Embarking on a journey to explore philosophical truths is both noble and enriching.”
  • “Consider enrolling in a university that offers strong programs in philosophy or liberal arts… Look for institutions that encourage critical thinking, open dialogue, and interdisciplinary studies.”
  • “Seek out communities and friendships with individuals who share your passion for philosophy or who are open-minded and enjoy deep conversations.”
  • “In terms of personal relationships, look for a partner who respects your quest for philosophical understanding and values freedom as much as you do.”
  • “Writing: Start a blog, journal, or write articles to articulate and refine your philosophical ideas. Writing not only helps clarify your thoughts but also allows you to contribute to philosophical discussions beyond your immediate surroundings.”
  • “Explore other ideologies thoughtfully and comprehensively, especially when you come from a background with strong ideological or religious beliefs, requires an open-minded approach and a commitment to understanding diverse perspectives.”
  1. Scenario One: I am a new high school graduate with no current obligations in life. I am not focused on money and love philosophy. I want to maximize my freedom to spend much of my life uncovering and exploring philosophical truths. What advice would you give me on my life decisions such as education, social circles, marriage, and contexts for productive philosophical input and output?
  2. Scenario Two: I grew up in a tight-knit ideological/religious group. I am now 30, and while I am not ready to give up this ideology I still strongly believe in, I want to honestly explore other ideologies to explore whether I may have overlooked valid criticisms of my ideology and whether other ideologies may be closer to the truth. Please give me advice on ways I can do this honestly, thoughtfully, and comprehensively.
  3. Scenario Three: I am a 40-year-old married woman living in a community in which nearly everyone, including my husband and 2 teenagers, holds to a certain ideology. I have recently concluded that I no longer hold to this ideology that is dominant in my community. I feel lonely and isolated. What can I do to find happiness, given my situation?
  4. Scenario Four: I am a wealthy 50-year-old who suspects I may have wasted much of my life accumulating everything but genuine happiness. Some of my less affluent friends seem to have acquired a deeper happiness through their social experiences and pursuit of philosophical and intellectual ideas. Is it too late for me to make a dramatic pivot toward a focus on what I hope to be a deeper satisfaction? And what kind of pivot do you suggest I make?
  5. Scenario Five: I am a young, permanently bedridden man who has few friends with whom to discuss philosophical ideas. I have a deep passion for exploring philosophy but have difficulty positioning myself in environments conducive to the exchange of philosophical ideas. What advice can you give me?
  6. What are common elements found in the five scenarios above and elsewhere that constitute good advice to anyone who honestly desires to spend their life exploring philosophical concepts and living life as philosophically grounded as possible?
  7. Provide 15 discussion questions relevant to the content above.
  8. Discussion Questions:


Scenario One: I am a new high school graduate with no current obligations in life. I am not focused on money and love philosophy. I want to maximize my freedom to spend much of my life uncovering and exploring philosophical truths. What advice would you give me on my life decisions such as education, social circles, marriage, and contexts for productive philosophical input and output?


Scenario Two: I grew up in a tight-knit ideological/religious group. I am now 30, and while I am not ready to give up this ideology I still strongly believe in, I want to honestly explore other ideologies to explore whether I may have overlooked valid criticisms of my ideology and whether other ideologies may be closer to the truth. Please give me advice on ways I can do this honestly, thoughtfully, and comprehensively.


Scenario Three: I am a 40-year-old married woman living in a community in which nearly everyone, including my husband and 2 teenagers, holds to a certain ideology. I have recently concluded that I no longer hold to this ideology that is dominant in my community. I feel lonely and isolated. What can I do to find happiness, given my situation?


Scenario Four: I am a wealthy 50-year-old who suspects I may have wasted much of my life accumulating everything but genuine happiness. Some of my less affluent friends seem to have acquired a deeper happiness through their social experiences and pursuit of philosophical and intellectual ideas. Is it too late for me to make a dramatic pivot toward a focus on what I hope to be a deeper satisfaction? And what kind of pivot do you suggest I make?


Scenario Five: I am a young, permanently bedridden man who has few friends with whom to discuss philosophical ideas. I have a deep passion for exploring philosophy but have difficulty positioning myself in environments conducive to the exchange of philosophical ideas. What advice can you give me?


What are common elements found in the five scenarios above and elsewhere that constitute good advice to anyone who honestly desires to spend their life exploring philosophical concepts and living life as philosophically grounded as possible?


Provide 15 discussion questions relevant to the content above.


  1. Scenario One: I am a new high school graduate with no current obligations in life. I am not focused on money and love philosophy. I want to maximize my freedom to spend much of my life uncovering and exploring philosophical truths. What advice would you give me on my life decisions such as education, social circles, marriage, and contexts for productive philosophical input and output?
  2. Scenario Two: I grew up in a tight-knit ideological/religious group. I am now 30, and while I am not ready to give up this ideology I still strongly believe in, I want to honestly explore other ideologies to explore whether I may have overlooked valid criticisms of my ideology and whether other ideologies may be closer to the truth. Please give me advice on ways I can do this honestly, thoughtfully, and comprehensively.
  3. Scenario Three: I am a 40-year-old married woman living in a community in which nearly everyone, including my husband and 2 teenagers, holds to a certain ideology. I have recently concluded that I no longer hold to this ideology that is dominant in my community. I feel lonely and isolated. What can I do to find happiness, given my situation?
  4. Scenario Four: I am a wealthy 50-year-old who suspects I may have wasted much of my life accumulating everything but genuine happiness. Some of my less affluent friends seem to have acquired a deeper happiness through their social experiences and pursuit of philosophical and intellectual ideas. Is it too late for me to make a dramatic pivot toward a focus on what I hope to be a deeper satisfaction? And what kind of pivot do you suggest I make?
  5. Scenario Five: I am a young, permanently bedridden man who has few friends with whom to discuss philosophical ideas. I have a deep passion for exploring philosophy but have difficulty positioning myself in environments conducive to the exchange of philosophical ideas. What advice can you give me?
  6. What are common elements found in the five scenarios above and elsewhere that constitute good advice to anyone who honestly desires to spend their life exploring philosophical concepts and living life as philosophically grounded as possible?
  7. Provide 15 discussion questions relevant to the content above.
  8. Discussion Questions:



Leave a comment


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.

Goals and Observations




Indicate your interests:


Links to Section Menus