Sidewalk Conversations

Parenting Isn’t Hard, It’s “My Son Thinks Teslas Fly” Hard with Jenn Orenstein


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We walk with Jenn through the decade-long journey of parenting a son in prison, the toll it took on her faith and marriage, and the gritty, practical work of preparing for his return home. Honest, tender, and useful, this conversation turns pain into a roadmap for others.

• borrowing faith from community during crisis
• marriage strain and choosing openness
• “get your house in order” as a guiding practice
• therapy, forgiveness and preparing a healed home
• reentry realities from tech shock to daily autonomy
• brothers, lost years and starting from here
• writing a practical guide for families
• launching Rise and Ascend to walk with others
• trust over understanding as a daily choice

To learn more about The Rise and Ascend Foundation and the Family Guide to Reintegration email Mike Orenstein at [email protected].

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Shoreline Church | Austin, TX
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Sidewalk ConversationsBy Piet Van Waarde