The MY House Podcast Ep.68: "Toward a Meaningful Life" with Rabbi Simon JacobsonThe MY House Podcast Ep.68: "Toward a Meaningful Life" with Rabbi Simon Jacobson
The MY House Podcast Network
Michelle Overstreet, Rabbi Mendy Greenberg, and Rabbi Simon Jacobson talk through themes from *Toward a Meaningful Life*, including grief, purpose, and spiritual homelessness. The conversation links Jewish wisdom to the work of MY House and highlights how community, service, and faith can support people facing loss, depression, or instability.
24:16•22 May 2026
Toward a Meaningful Life: Faith, Grief and Purpose at MY House
Episode Overview
- Feeding the soul and spirit is as essential as meeting material needs if you want genuine happiness.
- When struggling with depression or pain, seeking ways to help others and engage with community can shift your perspective.
- Grief can be handed over to God or a higher power, allowing strength to return in place of being stuck in despair.
- True homelessness can be spiritual as well as physical; having many houses does not guarantee feeling at home in life.
- Education and child‑rearing work best when parents, teachers, and the wider community share responsibility and values.
“You can have a home and also be homeless… if you don’t feed your soul as much as you feed your body, you will never be really happy.”
What can we learn from those who have battled addiction, homelessness, or deep loss about living a meaningful life? This conversation between Michelle Overstreet, Rabbi Mendy Greenberg, and author Rabbi Simon Jacobson gives a heartfelt answer rooted in age‑old Jewish wisdom and very modern struggles. Centred around Jacobson’s book *Toward a Meaningful Life*, the chat looks at how the teachings of the Lubavitcher Rebbe, Menachem Mendel Schneerson, speak to everyday issues: grief, depression, relationships, community and purpose.
Jacobson explains how he spent years memorising the Rebbe’s talks on Shabbat and holidays, then later “distill[ing] these thousands and thousands of pages… into a book… geared toward a wider audience, Jews and Non‑Jews,” touching every aspect of life. Listeners who are dealing with loss or emotional pain may be especially drawn to the sections on death and grief.
Michelle shares how those chapters helped her after the death of her husband, while Jacobson recalls a South African CEO who said the book’s grief chapter helped him “give my grief to God and get strength in return” after losing his son. The episode also connects these ideas directly to the MY House mission: supporting homeless and at‑risk youth.
Jacobson notes that “you can have a home and also be homeless” if you lack purpose and spiritual nourishment, a point that lands strongly in a setting working daily with young people searching for belonging. Expect a warm, story‑rich conversation rather than heavy theology. Themes of community engagement, helping others when you feel low, and “feeding your soul as much as you feed your body” run throughout, with plenty of practical angles for parents, helpers, and anyone feeling spiritually hungry.
If you’ve ever wondered how faith, purpose, and community can steady you through grief, addiction, or just modern life’s chaos, this talk might be the gentle nudge you need to rethink what truly makes life meaningful.
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