Learn From Our Mistakes
Jun 24, 2026 · 55 min · 11 segments
Send a message to the pod! We bounce from time blindness and everyday chaos into the surprisingly hard work of speaking up when money, family, and…
Send a message to the pod! We bounce from time blindness and everyday chaos into the surprisingly hard work of speaking up when money, family, and expectations collide. We share what we’re learning about confidence, boundaries, and how to advocate as a couple when a “gift” starts to feel like a bill. • running late dynamics, time blindness, and repairing the vibe • unexpected love for Panera breakfast sandwiches • studio mishaps, spiders, and a highlight reel of weird bites and stings • embarrassment versus avoidance, plus how we “project” confidence • the consulting lesson that nobody fully knows what’s going on • World Cup visitor content, U.S. scale shock, and why walking everywhere backfires • our passenger rail rant and the infrastructure trade-offs • parenting misstep of hyping plans too early, then managing heartbreak • word of the week: ultra crepidarian • Enneagram voicemail, why we like it, and why we refuse to be boxed in by it • horoscope skepticism, being open to woo-woo, and why tarot sparks better conversations • navigating in-laws when a wedding couch “gift” becomes a major expense • setting the precedent early and letting your partner handle their own family communication If you've got a thought to share or are looking for a bit of advice on something, leave us a voicemail at the link below! https://www.speakpipe.com/overthinkingpod If you'd like to message us you can use the email below or the text link at the top overthinking@theoverbys.com CONNECT: TikTok: @jojohnsonoverby / @matt.overby Instagram: @jojohnsonoverby / @matt.overby Website: https://jojohnsonoverby.com/
Send a message to the pod! We bounce from time blindness and everyday chaos into the surprisingly hard work of speaking up when money, family, and…
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