Begin Again: When Life Doesn’t Go as Planned
September 1, 2026
How do you begin again when life doesn’t turn out the way you imagined?
In this episode of the Emotional Longevity Podcast, Dr. Elisha Goldstein sits down with artist, writer, and author Alessandra Olanow to explore what it means to start over, let go of old expectations, and find your way forward when life falls apart.
Alessandra shares the deeply personal story behind her book, Begin Again, and Again, and Again, including career uncertainty, divorce, grief, parenting, and the moment she realized that moving into a smaller life didn’t necessarily mean moving backward.
Together, they explore how to hold life more lightly, sit with difficult emotions, reclaim self-worth, and take small steps instead of becoming overwhelmed by the big picture.
How do you begin again when life doesn’t turn out the way you imagined?
In this episode of the Emotional Longevity Podcast, Dr. Elisha Goldstein sits down with artist, writer, and author Alessandra Olanow to explore what it means to start over, let go of old expectations, and find your way forward when life falls apart.
Alessandra shares the deeply personal story behind her book, Begin Again, and Again, and Again, including career uncertainty, divorce, grief, parenting, and the moment she realized that moving into a smaller life didn’t necessarily mean moving backward.
Together, they explore how to hold life more lightly, sit with difficult emotions, reclaim self-worth, and take small steps instead of becoming overwhelmed by the big picture.
🎧 In this episode, we cover:
✅ Why beginning again is something we may have to do again and again
✅ How painful experiences can change the way we appreciate life
✅ What it means to hold your knowing more gently
✅ Why quiet and stillness can help us reconnect with ourselves
✅ How sitting with difficult feelings can reveal what we need
✅ Reclaiming self-worth without waiting for someone else’s approval
✅ Giving yourself permission to create, change, and become
✅ Why protecting yourself can also close you off from connection
✅ The courage it takes to put your hand out and ask for support
✅ How small steps can make overwhelming situations more manageable
✅ Why perpetual renewal may be more realistic than permanent transformation
⏱ Chapters
00:00 – The Question of Beginning Again
02:21 – There Is More Than One Beginning
03:39 – What Experience Teaches Us
05:36 – Nothing Is Fixed
07:24 – The Story Behind the Book
08:13 – When Her Career Fell Apart
10:00 – Finding Stillness in Panic
11:13 – Solving One Thing at a Time
12:02 – Moving Forward Instead of Backward
13:10 – Finding Quiet in a Noisy World
14:51 – Does Life Choose Our New Beginnings?
16:19 – Sitting With Your Feelings
18:29 – Processing Pain and Grief
22:43 – Asking “Is That True?”
24:35 – Making Space to Sit Still
25:07 – Giving Yourself Permission to Be a Writer
27:51 – Letting Go of Who You’re Supposed to Be
29:32 – Protection vs. Connection
31:14 – Putting Your Hand Out
32:54 – Why Asking for Help Is So Hard
33:27 – Learning to Hold Life Lightly
35:32 – Taking One Small Step
37:11 – The Art of Perpetual Renewal
38:47 – Where to Find Alessandra
📕 Begin Again, and Again, and Again: Notes on the Art of Perpetual Renewal is available wherever books are sold.
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