This Was Supposed to be Easy Podcast

S1 Episode 18: We Thought Becoming Confident Was Supposed to Be Easy

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In this heart-to-heart episode of This Was Supposed to Be Easy, Amy and Cheryl open up about the winding, sometimes bumpy journey of confidence at different stages of life. From the myth that confidence simply comes with age to the surprising moments that can shake it, they explore where confidence shows up, where it wobbles, and how curiosity, courage, and micro-wins help us grow along the way. Whether you’re stepping into something new or cheering on someone else, this conversation offers gentle reminders (and some real-life stories) that encouraging someone else’s confidence isn’t pie — there’s plenty to go around.

This Conversation Touches On

  • The non-linear path of building confidence at every age
  • How trying new things (and not waiting for perfect) strengthens confidence
  • The power of micro-wins and small acts of bravery
  • Self-talk and why it matters
  • The contagious nature of confidence in community
  • Why asking questions shows strength, not weakness

    • Themes

     Curiosity as a pathway to growth

     Confidence as service, not selfishness
     Micro-wins and micro-steps that build resilience
     Letting go of perfection to embrace progress

    Episode Highlights

    • Amy reflects on how stepping into new roles (like going back to school or launching this podcast!) has both boosted and challenged her confidence.
    • Cheryl shares a personal story about advocating for herself — and how her daughter’s determination to intern in Manhattan reminds us not to close doors before we try.
    • The duo unpacks the idea that truly confident people don’t ask others to shrink — they create space where everyone can shine.
    • Practical strategies like affirmations, asking for feedback, and choosing “confidence boosters” (hello, power blazer or hot pink dress!)
    • The magic of reframing from “Why me?” to “Why not me?”

      • Listener’s Challenge

      Where in your life are you feeling extra confident these days? We also love to know where you might be stepping into something new that feels a little shaky? Share with us — we’d love to cheer you on!  Drop a comment on Spotify, message us on socials, or visit our website. Let’s build that contagious confidence together.

      Key Quotes

      📝 "Confidence doesn’t have to be loud. In fact, often the loudest ones in the room are some of the least confident people there." — Amy

      📝 "It’s not about one of us being the most confident. It’s about creating a space where we can all feel confident." — Cheryl

      📝 "Don’t shut the door before you ever actually turn the handle." — Cheryl

      📝 "Why not me? Why wouldn’t I go after the thing I want?" — Amy

      Listen Now

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      This Was Supposed to be Easy PodcastBy supposedtobeeasy