Brutally Anna — "Everybody's Dying: Here's How It Taught Me To Live"
Host: Anna Kai
Date: September 26, 2025
Podcast Theme: Unflinching honesty about the messiness of being human
Episode Overview
In this introspective episode, Anna Kai returns from a two-month hiatus to discuss her personal journey through grief, the value of living authentically, and why losing loved ones this year profoundly changed her approach to life and content creation. Anna reflects on the pressure to “perform” for others, shares the wisdom gleaned from funerals, and candidly addresses her evolving relationship with success, mental health, and her online persona.
Key Discussion Points & Insights
Anna’s Hiatus and Return to Podcasting
- Anna opens up about her break from podcasting, citing burnout, underwhelming podcast success, and the need for a creative shakeup ([00:43]).
- Admits struggles with confidence after initial podcast launch.
- Created a Substack during the break for deeper, written reflection.
- Returns for an eight-episode arc at the encouragement of her supportive podcast network.
- Expresses ambivalence about the future of the show but relishes the authenticity of podcasting in its simplest form—just her and the mic.
- “Maybe the only part of podcasting that I really didn’t like was the production aspect because... I was editing all of my own video... I really have a new admiration for video editors because that to me is like such mind numbing work.” (Anna, [04:20])
Death, Grief, and the Meaning of Life
- Main theme: The impact of attending multiple funerals this year and how confronting mortality has forced Anna to reevaluate her priorities ([07:00]).
- "I've watched so many extended family members just completely pass at untimely ages this year that it has really crystallized for me how none of us are guaranteed any time on this earth. And that's such bullshit..." (Anna, [07:35])
- Anna wrestles with the “unfairness” of losing good people too soon and how it illuminated the emptiness of living to impress others.
Rejecting Performative Living & Embracing Authenticity
- Contrasts her current, low-key approach to birthdays and personal milestones to the pressure for elaborate, performative celebrations in her 20s ([09:40]).
- “I don't want to feel pressure to perform or put on a great birthday for anyone else. I also don't want to pressure anyone else to make it a great birthday for me.” (Anna, [11:05])
- Revels in small, private moments with close family rather than public-facing celebrations.
Influencer Culture: Living vs. Showing
- Reflects candidly on her career as a public-facing creator:
- Values privacy, rarely involves family in online content.
- Cites a fellow influencer’s frank confession: prioritizing “showing my life over living my life,” which Anna rejects as a sacrifice she’s not willing to make ([13:40]).
- “I am an influencer that despises capturing my life for social media. That’s why the majority of my content is very controlled.” (Anna, [13:10])
- Anna would “regret not chucking my phone into the abyss” rather than not sharing more of her personal life online if her time ended suddenly.
Redefining Success, Productivity, and Happiness
- Shares her journey off Zoloft and newfound emotional equilibrium ([17:48]).
- Emphasizes being intentional with work: prioritizing writing and manageable content rather than chasing constant, unsustainable growth.
- Quotes her mother’s surprising advice: “Anna, I think you need to just enjoy your life. And the way that you’re going to enjoy your life is by lowering your expectations for what the future is going to bring you.” ([19:47])
- Anna admits this “was exactly what I needed to hear in the moment.”
- Mentions the “hamster wheel of capitalism” and encourages listeners to evaluate whether their continued striving is necessary, or if they’re manufacturing struggle out of habit ([21:25]).
The Beauty of Ordinary Moments
- Expresses deep gratitude for simple, unglamorous family time in her Pennsylvania hometown—no makeup, eating Chinese food, just being together ([21:03]).
- “Those are the things I’m gonna miss the most one day. Because nothing is forever. So those are the things I prioritize doing in my life right now. Even though they don't make for good Instagrams…” (Anna, [21:10])
- Urges listeners to appreciate the present instead of always focusing on the next achievement.
Notable Quotes & Memorable Moments
- “I have this thing in my head where I feel like I’m not good at podcasting... it’s because my podcast did not perform nearly as well as I had hoped... that was a huge blow to my confidence.” ([04:05])
- “I am in a very public facing business... but it’s almost ironic, like the more I do this, the more I realize like I just want to keep my personal life and the things that truly fill up my cup very private.” ([12:30])
- “The sacrifice I’ve made in building this career is that I have prioritized showing my life versus living my life... that’s not a sacrifice I’m willing to make.” ([13:40])
- “We think success equates joy. And what I’ve realized... is I haven’t taken a step back, but what I’ve really done is become more intentional with what I lean into in my work.” ([16:50])
- “If I were to die next week... I would not regret not showing more of my life to you guys online. I would regret not chucking my phone into the abyss and spending a Friday night doing absolutely nothing with my family.” ([15:27])
- “You cannot enjoy the present if you're always looking ahead.” ([18:35])
- “What truly makes me happy is spending time with my family and friends and doing typically very unglamorous things... But those are the things I’m gonna miss the most one day.” ([21:10])
- “The biggest problem was that we refused to see how much a gift the present was.” ([22:10])
Important Timestamps
- 00:43 — Anna addresses her hiatus and self-doubt about podcasting
- 04:20 — On podcasting production burnout and new appreciation for video editors
- 07:00 — Introduction to the main topic: Death and what it has taught Anna
- 09:40 — Reflection on birthdays, performative friendship, and social pressure
- 13:10 — Anna’s discomfort with influencer culture and privacy boundaries
- 15:27 — What Anna would truly regret if her time ended unexpectedly
- 16:50 — Letting go of hustle mindset, redefining creative work
- 17:48 — Update on weaning off Zoloft and mental health
- 19:47 — Mother's advice about lowering expectations and enjoying life
- 21:03 — The beauty and value of simple family routines
- 22:10 — Final reflection: the present as a gift
Episode Tone & Style
True to the podcast’s premise, Anna is frank, funny, a bit self-deprecating, and deeply relatable. She eschews superficial advice for raw, lived experience, often pausing to rephrase, add context, or admit discomfort—anchoring her reflections with specific, real-life examples. Listeners are encouraged to embrace self-honesty, question societal scripts, and savor the fleeting, imperfect joys of daily life.
Best for:
Listeners navigating grief, questioning their relationship to success and social performance, or simply craving honest, down-to-earth dialogue about the messy reality of living—and trying to truly enjoy it.