What is philosophical coaching?

Although Aristotle said that philosophy begins with wonder, the kind of philosophical coaching and advising I do typically begins with something more urgent, such as a career challenge, a relationship issue, a major life change, or a desire for greater meaning and fulfillment.

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 me?
  • Where do I feel stuck?
  • What is out of balance?
  • What doesn’t feel right?
  • What is perplexing about the situation?
  • What is frustrating?
  • What concerns me most?
  • What am I wondering about?
  • What brought this to a head?
  • How did I get here?
  • What actions did I take leading to this?
  • Where was I headed when this happened?
  • What have I tried so far?
  • What obstacles have I 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 my actions?
  • What assumptions are at play here?
  • What are my thoughts?
  • What are my feelings?
  • Am I missing any information?
  • How can I account for this?
  • How would others account for this?
  • Are there worldviews in which this makes perfect sense?
  • Can I think of other explanations?
  • How might a neutral observer view the situation?
  • How might another person have handled this?
  • How important is this to me really?
  • What’s my 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 my assessment?
  • How might I seek harmony?
  • How might I balance this out?
  • Can I 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 my outlook?
  • Could I look at this from another viewpoint?
  • Is there more to explore?
  • What’s the best explanation?
  • What thoughts and values guided my commitments and practices?
  • Do they still make sense?
  • Do they harbor hidden contradictions?
  • Do they still fit with what I’ve learned and who I really am?

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 yourself now are:

  • What am I learning?
  • What resonates with me?
  • How can I get back in balance?
  • How does this fit with my values?
  • What is the big picture?
  • Can I put all this together?
  • Where do I go from here?
  • Can I see this as an opportunity?
  • What possibilities are opening up?
  • What are my goals now?
  • What am I envisioning?
  • What excites me about this vision?
  • What challenges do I foresee?
  • What would my best friend say?
  • What might my 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 I think of?
  • What’s the worst that could happen?
  • What’s the best that could happen?
  • What’s my hypothesis?
  • How would I test it?
  • What could I try?
  • What could I learn?
  • What feels most appropriate?
  • What feels most balanced?
  • What’s my plan?
  • What will I commit to?
  • What will I do?
  • When will I do it?
  • What do I envision will happen?
  • How will I prepare?
  • What support do I 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 I do?
  • What was the impact?
  • What was I aware of at the time?
  • How did it go?
  • Did I hit any obstacles?
  • What did I learn?
  • What might I do differently next time?
  • How did it feel?
  • What do I think now?
  • What new skills am I building?
  • Can I make this a regular practice?
  • Has taking action changed my 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!

Contact me at to schedule an initial conversation, in which we’ll talk about your goals and figure out if you might want to work with me. Please note that, as with Socrates of old, I do not expect payment for our conversations.