Feeling behind in life? You’re not alone—and you’re not broken. In this episode, Sierra and her mom Holly talk about the unspoken pressure women face to have it all “figured out” by a certain age. From career pivots to delayed milestones and self-imposed comparison traps, this episode is an honest exploration of what it means to let go of timelines and live life on your own terms. Tune in for practical wisdom, a few laughs, and the gentle nudge you didn’t know you needed to embrace where you are—right now.
Show Timestamps
00:00 – Intro + Emma Watson Quote Sierra opens the conversation with a stat and a powerful quote about feeling behind.
04:49 – Why Do We Feel So Pressured? Holly and Sierra explore the societal and social media-driven timelines women face in their 20s and 30s.
09:20 – Personal Stories: Our Timelines Didn’t Go as Planned Both share moments they felt “behind” and how they’ve reframed those experiences.
16:22 – Letting Go of the Checklist Life Sierra opens up about marriage, baby pressure, and redefining what “having it all” means.
25:11 – Ambition vs. Grace They reflect on hustle culture, burnout, and choosing to slow down intentionally.
34:14 – The Inner Dialogue Shift: Gratitude + Mindset Reframes Practical advice from Holly on how to rewire your thoughts when you feel behind.
48:34 – Final Reflection “What’s one thing you didn’t do on time that turned out to be exactly right?” (A question for listeners, too!)
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