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Dear Sugars · WBUR

Repost: Change Is A Work In Progress

March 7, 2026·35 min·3 clips
The 17-year-old writes a new letter detailing his goal to become a therapist and help others, showing a shift from struggle to hope.
The episode opens in motion. Cheryl talks about taking her family through New Zealand, Nepal, Tanzania, Kenya, Qatar, and Portugal, a trip she had meant to take for a long time. Not a vacation, exactly. More like an intention finally kept. From there, the conversation moves into the new year, where reflection feels less like a neat ritual and more like a nudge to look at what has passed and what is still coming. Then the old letter comes back. Steve and Cheryl revisit the mother who wrote in 2015 as Bad Mom, saying she hated parenting and felt trapped by it. The pain is direct. What landed for many listeners was not the shock of that confession, but the relief of hearing someone say out loud what they had felt too. The advice was human, not polished. Cheryl, Steve, and Lois Nakame had told her she did not have to be a perfect mother. Forgiveness sits at the center here. They talk about yelling, regret, repair, and the way children learn from seeing adults come back and try again. Then they call Amber. She is surprised by how real they seem, like her daughter meeting Elsa and Anna at Disneyland. The call warms up fast. Steve jokes about an Elsa costume, and suddenly the letter writer is not a problem to solve. She is a person. That is what gives the episode its pull. The question is not whether the advice was flawless. It is whether advice can survive contact with the life that comes after it. By the end, Steve and Cheryl leave room for criticism, less defensiveness, and actual change where it is needed.

As heard by us

A tender look at parenting guilt, change, and the work of forgiving yourself.

Steve Allman and Cheryl Strayed treat change as something people move through, not something they simply announce. One voice circles intentions, a long family trip, and the odd way another person's wonder can be felt as bitterness.

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Why you'd press play

For a reflective look at parenting guilt, self-forgiveness, and making amends.

Read the full recommendation in PlayNext →
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