Ep. 166: When Your Life Doesn't Follow the Expected Script episode artwork

EPISODE · Feb 25, 2026 · 17 MIN

Ep. 166: When Your Life Doesn't Follow the Expected Script

from Maybe I Can® with Debbie Weiss · host Debbie Weiss

Send us Fan MailIn this episode of the Maybe I Can Podcast, I talk about what happens when your life doesn’t follow the expected script.After hearing someone younger than me share that she plans to retire at 63 — the same age I’m about to turn — I noticed how quickly my mind shifted into self-judgment. I started replaying financial decisions, questioning myself, and telling myself I should be further along.That reaction made me realize how often we measure our lives against someone else’s timeline — without knowing their full story.In this episode, I share: • Why comparison ignores context • How life chapters like infertility, caregiving, loss, and reinvention shift our timelines • The emotional cost of measuring ourselves against others • Why different does not mean delayedThere is no universal life schedule. There is no single script we’re all supposed to follow.If you’ve ever felt behind, late, or like you missed something, this conversation is for you.You are exactly where you need to be — based on the life you’ve actually lived.Maybe we can put down the measuring stick together.Support the show🌸✨ WELCOME — START HERE ✨🌸 (Consider this your gentle nudge toward something new.)💖 NEW! The Sprinkle Effect™ Card Deck 52 small mindset shifts to help you reconnect, refocus, and rediscover joy — one sprinkle at a time. 👉 https://bit.ly/4pUvreV📘 NEW! The Sprinkle Effect™ Book Small sprinkles. Big change. This is where the magic begins. 👉 https://www.debbierweiss.com/thesprinkleeffect🌱 FREE GIFT FOR YOU Kickstart Your New Life A simple, life-changing workbook for women ready to turn the page and begin again — gently. ✨ Download here: https://www.debbierweiss.com/kickstart🌸 READY TO GO DEEPER? 🌸 Maybe I Can: Begin to Change Your Life Course A six-module journey designed to help you move through life transitions with clarity, courage, and confidence — at your own pace, with lifetime access. 👉 https://www.debbierweiss.com/beginchange🤍 WORK WITH ME From speaking and workshops to coaching and collaborations — explore all the ways we can sprinkle forward together. 👉 https://www.debbierweiss.com/workwithdebbie...

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Send us Fan Mail In this episode of the Maybe I Can Podcast, I talk about what happens when your life doesn’t follow the expected script. After hearing someone younger than me share that she plans to retire at 63 — the same age I’m about to turn — I noticed how quickly my mind shifted into self-judgment. I started replaying financial decisions, questioning myself, and telling myself I should be further along. That reaction made me realize how often we measure our lives against someone else’s ...

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Ep. 166: When Your Life Doesn't Follow the Expected Script

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This episode was published on February 25, 2026.

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