Although Socrates and Aristotle said that philosophy begins with wonder, philosophical coaching typically begins with something more urgent, such as a career challenge, a relationship issue, money troubles, a midlife crisis, or even a general feeling of meaninglessness.

Following the ancient Greeks, I call such an experience an impasse (ἀπορία). My preferred approach to addressing an impasse is dialectic, which Aristotle developed to work through intellectual impasses and which I have adapted to work through personal impasses. (Aristotelian dialectic steers a middle way between the two most common approaches to philosophical practice: pure Socratic dialogue and the correction of critical thinking errors.)

In my adaptation to action-oriented reflection, dialectic encompasses six phases, which guide you to full understanding and resolution through appropriate questions at each phase.

Phase 1: Impasse

In the impasse phase you take stock of where you are, how you got here, and the blockages you’re experiencing on the way to fulfillment and the achievement of your goals. The subtleties of your emotions are important clues at this time: how exactly you might feel frustrated, perplexed, surprised, thwarted, off balance, denied, derailed, brought up short. Here are some of the questions you might ask yourself:

  • What is blocking you?
  • Where do you feel stuck?
  • What is out of balance?
  • What doesn’t feel right?
  • What is perplexing about the situation?
  • What is frustrating to you?
  • What concerns you most?
  • What are you wondering about?
  • What brought this to a head?
  • What have you tried so far?
  • How did you get here?
  • What actions did you take?
  • Where were you headed?
  • What obstacles have you hit?

Phase 2: Perspective

The perspective phase is a time to gather more information and reflect on assumptions underlying your experience. It’s also a great opportunity to consider insights from a wide variety of wisdom thinkers and traditions (e.g., what does Aristotle say about friendship or what does Thoreau say about simplicity?). We might also consider the results of scientific research in fields like evolutionary psychology and personality theory. Questions in this phase might include the following:

  • What commitments and practices shaped your actions?
  • What assumptions are at play here?
  • What are your thoughts?
  • What are your feelings?
  • Are you missing any information?
  • How can you account for this?
  • How would others account for this?
  • Are there worldviews in which this makes perfect sense?
  • Can you think of other explanations?
  • How might a neutral observer view the situation?
  • How might another person have handled this?
  • How important is this to you really?
  • What’s your perspective?

Phase 3: Analysis

During the analysis phase, you start to make sense of your experience by winnowing out perspectives that don’t fit with your values and goals, eliminating contradictions, and finding deeper harmonies on the way to a greater synthesis. Here are some relevant questions to help further your analysis:

  • What’s your assessment?
  • How might you seek harmony?
  • How might you balance this out?
  • Can you make sense of this from another angle?
  • What doesn’t fit?
  • What isn’t clear?
  • Where will this lead?
  • What might happen if something doesn’t change?
  • What are some possible scenarios?
  • What’s the most likely scenario?
  • Does this conflict with your outlook?
  • Could you take another view?
  • Is there more to explore?
  • What’s the best explanation?
  • What thoughts and values guided your commitments and practices?
  • Do they still make sense to you?
  • Do they harbor hidden contradictions?
  • Do they still fit with what you’ve learned and who you really are?

Phase 4: Synthesis

In the synthesis phase you begin to put it all together, modifying your worldview if needed to account for your impasse experience and to incorporate insights from the intellectual and emotional analysis you’ve completed so far. The objective here is a forward-looking vision for where you can go next in life, clearing the roadblocks for the next stage of personal growth. Some questions to ask now are:

  • What are you learning?
  • What resonates with you?
  • How can you get back in balance?
  • How does this fit with your values?
  • What is the big picture?
  • Can you put all this together?
  • Where do you go from here?
  • Can you see this as an opportunity?
  • What possibilities are opening up?
  • What is your goal now?
  • What are you envisioning?
  • What excites you about this vision?
  • What challenges do you foresee?
  • What would your best friend say?
  • What might your future self think?

Phase 5: Commitment

A clearer vision generates a wider field of action. This is a time to plan your next steps and make commitments consistent with your updated worldview, balancing the excitement of new possibilities against the risks of future obstacles to personal fulfillment. Now your questions turn from the philosophical to the practical as you prepare to take action:

  • What is the next step?
  • What options can you think of?
  • What’s the worst that could happen?
  • What’s the best that could happen?
  • What’s your hypothesis?
  • How would you test it?
  • What could you try?
  • What could you learn?
  • What feels most appropriate?
  • What feels most balanced?
  • What’s your plan?
  • What’s your commitment?
  • What will you do?
  • When will you do it?
  • What do you envision will happen?
  • How will you prepare?
  • What support do you need?

Phase 6: Action

Taking action might seem purely practical, but it too has its philosophical aspects. Most importantly, you need to maintain awareness of your newfound vision and commitments so you can keep from going astray. Furthermore, action is not a one-time event, but a series of actions that over time will form new habits and practices. Each time you take action is an occasion for reflection, in which the questions you ask yourself lead to further self-development:

  • What was the situation?
  • What did you do?
  • What was the impact?
  • What were you aware of at the time?
  • How did it go?
  • Did you hit any obstacles?
  • What did you learn?
  • What would you do differently next time?
  • How did it feel?
  • What do you think now?
  • What new skills are you building?
  • Can you make this a regular practice?
  • Has taking action changed your outlook?

As you continue to take action, you can make subtle adjustments to your course, applying the same method on a smaller scale. And if you ever hit another major impasse, this method will work for you yet again, without needing a coach to guide you. Congratulations, you’re on the road to becoming your own philosopher!