Coaching practices for The Obstacle is the Way in Practice for My Teenager

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Does this sound like the set of challenges you might be facing?

  • Something blew up my plans and I’ve just been stewing in how unfair it is
  • I always blame the lack of time or the circumstances, but honestly something in me keeps stopping me
  • Something has blocked the path I was set on and my whole reaction is frustration and trying to force my original plan through it
  • The moment something goes wrong my head goes straight to "this is a disaster, it’s ruined"
  • I’ve thought this problem to death from every angle and I’m still frozen, waiting for the perfect plan before I move

Practices that may help

  1. The Obstacle Is the Way, in Practice
    Ryan Holiday repackages Stoicism into a three-part discipline for turning obstacles into advantage: control your perception of the problem, take deliberate action on it, and use your will to endure what you can’t change. The practices are modern framings of ancient Stoic moves, so their strongest support is the same — the lineage into cognitive reappraisal and the studied benefits of reframing and action.
  2. Find the advantage inside the obstacle
    Ask what this obstacle makes possible that nothing else would — the way through is often in it.
    The Obstacle Is the Way, in Practice
  3. Obstacle — find the inner obstacle in your way
    Identify the personal, internal block that actually stops you — a habit, feeling, or thought.
    WOOP: Wish, Outcome, Obstacle, Plan
  4. Treat each obstacle as an opportunity for the discipline of action
    When something blocks your intended action, ask what virtuous response the obstacle itself calls for.
    The Stoic Discipline of Action
  5. Control your perception of the obstacle
    The obstacle isn’t the problem — your interpretation of it is the first thing you can change.
    The Obstacle Is the Way, in Practice
  6. Take deliberate, persistent action
    Perception sets you up; action moves you through — start where you are, with what you have.
    The Obstacle Is the Way, in Practice
  7. Identify the main internal obstacle that stands between you and the wish
    Ask honestly: what is the primary thing in me — not outside me — that is most likely to block this wish?
    Mental Contrasting and WOOP
  8. Map the obstacles: WOOP your life-crafting goals
    For each goal, identify the most likely internal obstacle and plan your response before you need it.
    The Life Crafting Intervention: Scripting Your Future Self
  9. Reframe the obstacle as the material you work with
    Ask not "why did this happen to me?" but "what does this make possible or necessary?"
    Amor Fati: Loving What Happens
  10. Plan — make an if-then plan for the obstacle
    Pre-decide your response: "If [obstacle], then I will [effective action]."
    WOOP: Wish, Outcome, Obstacle, Plan

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