Mere Mortals Conversations Living With Ragrets | Feedback To Our Younger Selves
Oct 26, 2025
01:12:12
If you wish you could have let yourself been happier, then why didn't you?
In Episode #498 of 'Musings', Juan & discuss: advice we’d give to our 20-something selves after a decade of lessons, cringeworthy moments that come closest to genuine regret, why regret often intensifies closer to life’s end, the feedback loop of could-have-beens, when remorse is useful versus when it’s self-punishment, being more selfish about building skills and character, obsessively detailed on what you truly care about, applying first-principles/engineering thinking beyond work, investigating emotions two or three layers deeper, being strict on yourself and kinder to others, how to nurture confidence without creating monsters and why striving to be “uncommon” is easier to dial back than trying to switch it on later.
Huge shoutout to Magnolia Mayhem for the support, thank you so much!
Stan Link: https://stan.store/meremortals
Timeline:
(00:00:00) Intro
(00:01:26) Context setting & Petar's note
(00:05:36) Defining regret by cringe
(00:09:41) Deathbed regrets and when advice isnt enough
(00:12:57) Framing the advice: not just information
(00:21:07) Advice 1 (Juan): Be more selfish about skills and character
(00:27:02) Counterpoint (Kyrin): More selflessness and meaningful connection
(00:33:58) Boostagram Lounge: value-for-value support and listener message
(00:38:56) Advice 2 (Kyrin): Effort solves problems with thoughtfulness
(00:42:09) Advice 3 (Juan): Get obsessive about what you truly care about
(00:45:34) Emotional investigations: tracing feelings to root causes
(00:50:12) Think like an engineer: first principles beyond the lab and gym
(00:55:18) Working on virtues: honesty, courage, discipline
(00:57:03) Be strict with yourself, kinder to others
(01:00:54) Confidence and the hype man effect
(01:03:06) Become uncommon & cultivating the monster wisely
(01:11:04) Wrap-up & V4V
In Episode #498 of 'Musings', Juan & discuss: advice we’d give to our 20-something selves after a decade of lessons, cringeworthy moments that come closest to genuine regret, why regret often intensifies closer to life’s end, the feedback loop of could-have-beens, when remorse is useful versus when it’s self-punishment, being more selfish about building skills and character, obsessively detailed on what you truly care about, applying first-principles/engineering thinking beyond work, investigating emotions two or three layers deeper, being strict on yourself and kinder to others, how to nurture confidence without creating monsters and why striving to be “uncommon” is easier to dial back than trying to switch it on later.
Huge shoutout to Magnolia Mayhem for the support, thank you so much!
Stan Link: https://stan.store/meremortals
Timeline:
(00:00:00) Intro
(00:01:26) Context setting & Petar's note
(00:05:36) Defining regret by cringe
(00:09:41) Deathbed regrets and when advice isnt enough
(00:12:57) Framing the advice: not just information
(00:21:07) Advice 1 (Juan): Be more selfish about skills and character
(00:27:02) Counterpoint (Kyrin): More selflessness and meaningful connection
(00:33:58) Boostagram Lounge: value-for-value support and listener message
(00:38:56) Advice 2 (Kyrin): Effort solves problems with thoughtfulness
(00:42:09) Advice 3 (Juan): Get obsessive about what you truly care about
(00:45:34) Emotional investigations: tracing feelings to root causes
(00:50:12) Think like an engineer: first principles beyond the lab and gym
(00:55:18) Working on virtues: honesty, courage, discipline
(00:57:03) Be strict with yourself, kinder to others
(01:00:54) Confidence and the hype man effect
(01:03:06) Become uncommon & cultivating the monster wisely
(01:11:04) Wrap-up & V4V
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