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Jackassery: The Surprising Power of Honest Whining

Jackassery: The Surprising Power of Honest Whining

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Ever felt like a total jackass—frustrated with yourself, misunderstood, maybe even yelling at your own thoughts? In this episode, we dive into the raw and absurdly honest Angel Approach “Jackassery” memos—a surreal journey featuring talking donkeys, mercenaries, and even a brain that argues back.


What begins as a wandering rider’s rant turns into a profound exploration of why we blame, resist, and self-sabotage—and how those very flaws might be the doorway to transformation. Along the way, we uncover blockers that keep us from loving like Christ, wrestle with the ugly truths we avoid, and discover why our messy brokenness may actually be the key to redemption.


Part whimsical fable, part spiritual deep dive, this conversation will leave you laughing, unsettled, and—just maybe—seeing your own “jackassery” as the surprising place where God meets you.

Across the memos, the narrator identifies twelve key “blockers” that prevent Christ-like love:

  1. Self-reliance and blame – Deflecting responsibility onto the donkey, others, or even God .
  2. Blindness to self-deception – Our broken minds actively lie to us, leading us in circles .
  3. Idolatry of self-preservation – Prioritizing safety above God’s call, turning survival into an idol .
  4. Lack of empathy for internal struggles – Failure to show compassion toward our own inner brokenness .
  5. Self-perceived incompetence – Believing oneself too flawed or inadequate to lead or love .
  6. Misplaced value – Overvaluing intellect, strategy, or strength above heart and compassion .
  7. Fear of the ugly truth – Avoiding hard realities out of cynicism or fear of discomfort .
  8. Mistrust of the divine process – Holding back from surrender because we fear God’s path .
  9. Holding back our hearts – Believing love means protecting the heart, instead of giving it away .
  10. Fear of seeing God and ourselves – Hiding from exposure, judgment, and divine truth .
  11. Resentment and self-pity – Even in grace, clinging to “why me?” or “it should’ve been easier” .
  12. Narrow view of mission – Expecting only one form of reward or role, missing the wider calling .
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