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The Envy League

The Envy League

By: Matthew Doherty
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About this listen

Have you ever been so obsessed with something, it made you wish you thought of it first? Welcome to The Envy League, the show that turns jealousy into creatives ideas of your own.

Each week, join me, Matthew Doherty—your creative partner and resident envy expert—plus a rotating cast of guests as we obsess over everything in pop culture that makes us ask, “Why didn’t I think of that?!” We unpack why certain things make us feel something, riff out loud, and show you how to turn envy into big ideas of your own.

Whether you’re in a rut, questioning if you’re creative enough, or just chasing your next creative high, this is your secret society where envy becomes your creative superpower.


Admissions are open. Class is always in session. Follow or subscribe on Spotify, Apple, or wherever you get your podcasts.


New episodes drop every other Tuesday.

© 2025 The Envy League
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Episodes
  • How to Turn Daydreaming Into Your Most Unexpected Idea Yet (with Caroline Sweet)
    Nov 4 2025

    When’s the last time you really let yourself daydream? When you just let your weird little brain wander wherever it wanted to go.

    Most of us forgot how. But your best ideas didn’t.

    In this episode of The Envy League, we’re finally giving daydreaming the credit it deserves as one of the most underrated creative tools you forgot you had.

    And we’re not doing it alone!

    Meet our very first guest: the brilliantly talented and beautifully unhinged (in the best way possible) Caroline Sweet — actor, writer, improviser, director and your imagination’s permission slip. Together, we explore how to tap back into the secret, wonderfully chaotic space of your mind and what you find when you let yourself go.

    Today we're breaking down:

    - Why daydreaming is where the real ideas hide
    - How to unstick your brain with a set of daydreaming creative tools
    - Tiered daydreaming and how to find your dominant style
    - The magic of 30-minute daydreams (and why you should never self-edit them)
    - Why your most original ideas don’t come from thinking harder, they come from letting go

    If you’ve been over-editing your work, stuck in performance mode, or just forgot how to make things fun again, this episode is your permission to stop overthinking and start dreaming during the day like you used to as a kid.

    Because your next idea? It’s already in you.

    You just haven’t daydreamed it out yet.

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    38 mins
  • Secondhand Obsession: Why We Fear the Real Feeling
    Oct 22 2025

    You ever obsess over something you’re too scared to actually do?

    In the spirit of spooky season, I’m diving headfirst (but not too far) into the weirdly thrilling world of secondhand obsession — when you become obsessed with an experience you never actually live. That place where you almost watch the horror movie, almost ride the roller coaster, almost press play… but instead, you binge the reviews, reaction videos, plot summaries, and watch someone else survive it first.

    In this special Halloween episode of The Envy League, we explore why we crave the adrenaline of horror films without wanting to experience them. Why secondhand obsession isn’t cowardice — it’s emotional rehearsal. We talk scary movies, identity, fandom, borrowed bravery, and what it really means to envy the people who can fully feel the thing you’re still hovering around.

    Because at some point, the trailer won’t be enough.
    And envy? That’s the moment you stop outsourcing the feeling and start living it.

    Show More Show Less
    15 mins
  • Why We Grieve the Stories We Can’t Let Go
    Oct 8 2025

    You know that feeling when your favorite show finally ends and you’re left wrecked and grieving?

    In this episode of The Envy League, we’re talking about the strange, beautiful heartbreak that hits when a story you love finally comes to an end — and why that feeling is actually a sign of something great.

    We’ll break down:
    – Why creative grief is real (and underrated)
    – The Five Stages of Post-Finale Grief
    – How fandom helps us process what we lost
    – And why grief might be the clearest way to know if something is envy-worthy

    This one’s for anyone who’s ever mourned the end of a show, clung to the last page of a book, or chased that same feeling again trying to find something new to watch or binge.

    🎧 Hit play and let’s feel this one out together.


    Show More Show Less
    21 mins
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