You’re Not Behind: Releasing the Timeline
From Winsome Black by Kyla
December 30, 2025 · 8 min · Season 1 · Episode 1
About this episode
This episode discusses the grief of letting go of imagined life milestones and redefining success in your mid-20s.
In this episode of Winsome Black , we open up about the quiet grief that comes with releasing the life you once imagined — the milestones you thought you’d hit by a certain age, the version of yourself you planned to be by now, and the pressure to keep up with everyone else’s timeline. From mourning old dreams to questioning where our expectations really come from, this conversation explores what it means to grow, change your mind, and redefine success in your mid-20s. Let's Connect: YouTube: https://www.youtube.com/@winsomeblack Instagram:https://www.instagram.com/winsomeblack_/
Topics covered
- grief
- expectations
- success
- personal growth
- milestones
Keywords
- life timeline
- mid-20s
- dreams
- pressure
Mentioned in this episode
Books & works: Winsome Black
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