#77: Why Real Connection Is So Rare (And How to Find It) - Ashlee Raymond episode artwork

EPISODE · Mar 3, 2026 · 2H 31M

#77: Why Real Connection Is So Rare (And How to Find It) - Ashlee Raymond

from Watson-Howland

Why does real connection feel so rare, and what does hiding from yourself actually cost you? Ashlee Raymond is a writer, PA student, and published poet at 25 who's amassed thousands of Substack readers in just six months by saying what nobody else will.She's lived through elite-level figure skating, her dad's brain cancer diagnosis, heartbreak, and a quarter-life crisis, and turned every bit of it into writing that makes strangers message her in paragraphs.Subscribe for weekly conversations on love, identity, and learning to live without a mask.You’ll learn:VALUE BULLETS–Why curiosity is a lost art, and how dating apps have completely destroyed the ability to truly know someone–The one shift that changes every relationship: "It is more intriguing to be interested in somebody than to be interesting"–How Ashlee grew thousands of Substack readers in 6 months by writing journal entries she was terrified to post–The hidden cost of hiding yourself just to be liked, and why it quite honestly makes you feel like sh*t–What 11 years of elite figure skating taught her about identity, obsession, and losing yourself in one thing–How her dad's brain cancer diagnosis changed her life's direction, and why it led her to medicine–The real reason we stay in relationships we know aren't right (it's not stupidity, it's neurochemistry)Ashlee’s Work:Substack: ⁠https://substack.com/@ashleewrites⁠ Instagram: ⁠https://www.instagram.com/ashrayray/⁠ Book - Deep Dive: ⁠https://www.amazon.com/deep-dive-Ashlee-Raymond/dp/B0DDGY36CM/ref=sr_1_1?dib=eyJ2IjoiMSJ9.RKaSvNBj6dBRYTEzi6OUA5S0mbYYBtG4He1wwuDt55U.AhBhjaH6ivHHCDO7NRPNhw1ULUWNv0rjIW5Z3O-GjeA&dib_tag=se&keywords=deep+dive+ashlee+raymond&qid=1772535379&sr=8-1⁠Jacob’s Work Website: ⁠https://www.jacobjwatsonhowland.com⁠

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#77: Why Real Connection Is So Rare (And How to Find It) - Ashlee Raymond

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