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This Past Weekend w/ Theo Von

#621 - Andrew Santino

with Andrew Santino

Published October 30, 2025
Visit Podcast Website

About This Episode

Theo Von and comedian Andrew Santino catch up about touring, filming stand-up specials, and the intense pressure that comes with trying to "capture lightning in a bottle" on camera. They discuss Theo's turbulent Netflix taping, mental health struggles, paranoia after a government video used his clip, and the way online media distorted what happened. The conversation widens into technology and AI, Saudi and Qatari comedy festivals, hypocrisy in public outrage, aging, family, community, and what to do when having children may not be in the cards.

Topics Covered

Mental health Anxiety Online fame Relationships Travel and tourism Artificial intelligence Mixed martial arts Government corruption Workplace dynamics Personal development

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • Theo describes changing antidepressant medication, feeling emotionally flat on stage, and becoming deeply paranoid after a government immigration video used one of his jokes out of context, which fed into anxiety around his Netflix special taping.
  • Both comics explain how filming a special is fundamentally different from live stand-up, with cameras, resets, and too many decision-makers making it easy to overthink, lose confidence, and "drop the ball before the goal line."
  • Santino emphasizes the importance of having a supportive team-openers, friends, producers-who can restore a comedian's confidence when a taping feels shaky, and recalls how Zach Townsend helped him salvage crucial jokes in his Hulu special.
  • They discuss how media and social platforms amplified a distorted narrative about Theo's taping, repackaging old emotional clips as if they were new, and how choosing not to engage with the online storm protected his mental health.
  • Theo and Andrew use humor to explore serious topics like smart toilets, hacked cars, kinetic energy sidewalks, and AI-generated media, expressing concern that technology may soon control key life decisions for people.
  • Both men reflect on touring burnout, the grounding power of small daily rituals (like playing with a dog while drinking coffee), and the challenge of finding or maintaining community as friends marry and have children.
  • They debate whether people really want to know every detail about their health (full-body scans, toilet analytics) or whether accepting some ignorance can reduce anxiety about "impending doom."
  • Andrew defends performing in Saudi Arabia by focusing on young audiences' enthusiasm and Jimmy Carr's idea of judging countries by where they're going rather than only where they've been, while criticizing hypocrisy and infighting within the comedy community.
  • Santino talks openly about accepting that he and his wife likely won't have children and redirecting that parental energy toward mentees, coworkers, charity, and community, while Theo considers what a meaningful life without kids might look like.
  • They close by arguing that everyone is essentially a scared kid in an adult body, stressing empathy, avoiding online drama, and focusing on doing good in one's immediate world rather than policing others.

Podcast Notes

Introduction and catching up on touring and specials

Theo introduces Andrew Santino and his current projects

Theo says today's guest is comedian, actor, and podcaster Andrew Santino, known for "Whiskey Ginger" and "Bad Friends," with a new special "White Noise" on Hulu[1:15]
Andrew says he doesn't have to tour anymore for now and mentions they might have to retape his special[2:01]

Theo's Netflix taping experience and initial feelings

Theo explains that leaving the venue he thought the taping went "pretty good" but wasn't sure they fully got it due to hang-ups and stress[2:40]
He had switched off antidepressant medication before the taping to feel more emotion and have more of a storyline, because the meds were making it hard to access feelings[3:03]
• Theo describes antidepressants making emotions feel like they "stall out" and get stuck in the mud when he tries to feel something
The Department of Homeland Security immigration video using one of his jokes out of context scared him and contributed to paranoia before the special[3:21]
• He says they pulled his joke out of context and made it look like he was a spokesperson, which he never agreed to
Theo was receiving a lot of hate online related to that video and a recent Charlie Kirk issue, which made him paranoid at home and about people in his audience[3:55]
• Friends were texting him to "stay safe" after the Charlie Kirk situation, reinforcing the sense of threat

Pressure, anxiety, and the mechanics of filming a special

Overwhelm, too many cooks, and losing the thread on stage

Theo says there were too many cooks in the kitchen on the set, and during the taping he felt it was all too much to get the show off as well as he wanted[4:07]
He kept having trouble remembering where the next joke went and felt overwhelmed by details like stool placement matching between tapings[12:54]
• Theo mentions mentally "directing" during the performance, worrying about where the stool had been in the first show versus the second
He recalls needing to restart a couple of times during the tapings, adding to his stress[12:48]

Andrew's experience taping "White Noise"

Andrew says he changed about ten different things between the second-to-last and final show because he was freaking out that jokes weren't hitting like on tour[5:03]
Zach Townsend, his opener, helped him rewrite and tighten material and reassured him not to cut good jokes just because of one off show[5:09]
Andrew describes not committing fully to a few jokes during the first taping, likening it to NFL players dropping the ball before crossing the goal line[6:14]
• He admits doubting tags or punchline timing when cameras are on, which made him hesitate, unlike in live club shows where he feels free
On the last taping Zach reinstilled his confidence, telling him essentially to "cut it out" and commit to the material[6:38]

Differences between live comedy and taped specials

Andrew notes that in podcasts and live stand-up, people get jokes "straight from the tap," whereas taped specials have many more elements audiences don't see[4:55]
He quotes Dan Soder saying that podcasts are like drinking from the hose as a kid, while specials are heavily constructed[4:48]
Theo says there should almost be a visible meter that tells the audience how confident a comedian feels about a joke in that moment[6:07]
They agree that TV cameras change the brain and make comics overthink in ways that don't happen in regular live shows[6:30]

Emotional toll and physical anxiety during Theo's taping

Theo recalls walking onstage and his mouth immediately becoming extremely dry, which had never happened on tour and signaled to him that something was wrong[10:43]
• He felt he couldn't go back to the stool for water right away because the crowd was still clapping and it would look odd to take a break immediately
He told the audience at points that he was having a tough time, indicating his anxiety in real time[10:43]
After the show, he went out with friends to a country bar and felt they might have gotten it, but woke up to a storm of online criticism and articles[10:10]
• He says he deliberately avoided reading most of the online coverage and articles, learning not to feed that part of the internet

Specials as photo albums and Neil Brennan's advice

Theo shares that Neil Brennan told him before the show to remember this could be the last time he ever does that material and to enjoy it[12:13]
Theo now sees specials as "photo albums" for the time spent with that material and the connections it created with audiences[12:06]
He wonders if he tried to do too much by wanting more story and emotion about growing up and life within the special[11:54]

Security, paranoia, and behind-the-scenes chaos

Security guard, production chaos, and paranoia

Theo had just gotten a security guy, described as a very intense, tough ex-military or similar type, who was even stopping some of Theo's friends[13:40]
He jokes that there were about five extra production people who didn't need to be there, relaying radio messages to someone standing right next to them, making him feel like it was a prank[13:03]
The combination of security concerns, online threats, and production clutter heightened his paranoia going into the taping[15:58]

ROTC, cars, and humor about security archetypes

Andrew riffs that his ideal security guard would be a college ROTC guy with a wooden gun and a strong supplement regimen[14:06]
He tells a story of his college roommate getting kicked out of ROTC for not waking up or doing morning exercises, which he notes is hard to do because they "beg" for people[14:24]
They joke about ROTC guys buying Camaros or Mustangs, obsessing over quarter-mile times, and putting big engines into junk cars to compensate[14:54]

Coping, home life, and searching for space

Grounding routines and playing with the dog

Andrew says during times of public activity he focuses on drinking a whole pot of coffee in the morning and playing with his dog as a reset[18:08]
• He leaves his phone at home, walks, and plays with the dog in their small LA backyard with fake grass, which he prefers to maintaining real lawn

Theo's house-hunting dilemmas and future family considerations

Theo is looking for a place with more space but notes one option is too close to the interstate, making the yard loud enough that you'd have to yell at barbecues[19:12]
He debates whether to buy a house sized for a future family or just for himself and worries that choosing the latter might lock him into that life path[19:50]
Andrew asks if Theo has considered a compound with friends or family, but Theo worries about logistics and cleanliness[19:58]

Andrew's neatness and military family influence

Andrew describes himself as very neat, attributing it to his dad being the son of a military man where shoes couldn't be out of place[20:11]
He jokingly calls mislaid shoes his "Vietnam," saying he has flashbacks when he sees loose laces on the floor[20:39]

Redhead identity, extinction myths, and genetics

Ginger stereotypes and rare redhead combinations

Theo recalls a van full of redheads breaking down on his street as a kid and his dad reacting anxiously as more redheads emerged[20:53]
Andrew says when he meets another redhead he wants to see their "resume" first because he doesn't know if they're ally or enemy, emphasizing different "levels" of gingers[22:04]
They joke about black albino people with red hair and compare one image to Henry Rollins, blurring racial and ginger categories humorously[23:22]

Redhead extinction claim and genetics explanation

Theo brings up claims that redheads will be extinct by around 2060 and reacts anxiously to the timeline[24:17]
They read that the extinction claim has been debunked; red hair comes from recessive MC1R gene variants that can skip generations but won't disappear[24:44]
Andrew notes that redheads are technically "mutants" genetically and jokes that despite that he has never been booked in any Marvel project[24:58]

Touring, buses, Bobby Lee, and bodily functions

Andrew's touring plans and desire to reconnect with smaller venues

Andrew says his golf show season is ending and he wants to spend time working out a new hour in clubs and casinos instead of big tours[35:00]
He mentions specific clubs like Punch Line in San Francisco and Tempe Improv and says part of the goal is to visit friends while on the road[35:04]

Theo's fantasy of traveling with a future partner

Theo imagines that if he gets married he would like to travel the country with his wife in a camper before having kids, mixing shows with sightseeing[35:37]

Bus tour with Bobby Lee and breaking the no-poop rule

Andrew describes a bus tour he did with Bobby Lee where the number-one rule was no pooping on the bus, but Bobby broke the rule within the first week of a three-month tour[36:54]
He paints a picture of Bobby's small legs not reaching the floor on the toilet, requiring a squatty potty so he can feel grounded[37:28]
Andrew says sometimes he has to massage Bobby's back and sides like rolling out a tube of toothpaste to help him go to the bathroom[37:49]
He notes Bobby has lost significant weight on a GLP-1 medication, first trying one that made him very sick, then switching to another and losing around 30 pounds[38:17]

Dating apps, Bobby's habits, and Theo's brief experiment

Andrew says Bobby lives and dies by dating apps, talking to many women but often not committing or following through to real-life meetings[38:49]
Theo says he hasn't been on apps in about nine years and finds that world dark, noting his sensitivity to being left on read or rejected online[41:46]
He recounts once filling his profile pictures with Steven Avery and Brendan Dassey photos plus one Home Alone character, which got him in trouble with the service for using accused killers' images[39:56]

Theo's airplane flirtation misfire and self-critique

Interaction with a flight attendant and half an email

Theo tells a story about being on a plane with a tall, cute flight attendant who he felt a spark with and wanted to invite to a comedy show[26:31]
He hesitated to be too forward in the confined airplane environment and ended up offering his email instead of phone number, citing worries about professionalism and whether she might be married[27:43]
While trying to write his email on a napkin with a bad pen near the lavatory, an impatient woman kept banging on the bathroom door, creating pressure and a growing line of people[29:00]
• Theo says the pen barely worked on the textured wall, so only about four letters of his email were legible, and he finally gave up and sat down feeling like a loser
Andrew reassures him that at least he "kept swinging" and notes that if she really wanted to find him, Theo is a findable person[31:50]

Juggalos, poo dollars, and AI confusion

Gathering of the Juggalos survival tips

Andrew describes TikTok videos by a woman who gives tips for surviving the Gathering of the Juggalos, including warning about "poo dollars"-cash wrapped in feces that people pick up as a prank[1:03:39]
She explains people pass out for 12 hours there and others mess with their stuff or take wristbands while they're essentially "dead bodies" on cots[1:03:54]

Sora, deepfakes, and confusing reality

Andrew notes he is seeing many AI-generated videos, mentioning a system called Sora and an explosion of fake Kobe Bryant clips doing wild things like dunking on old women[1:05:26]
Theo and Andrew admit how often they are fooled by AI and say in the future people will increasingly not know what is real[1:05:08]

Technology, AI, smart infrastructure, and bodily surveillance

Shohei Ohtani, lab-made jokes, and family background

Andrew jokes that Shohei Ohtani looks like he was made in a lab to be the greatest baseball player, citing his size and skill as rare for a Japanese player[1:06:17]
They read a summary that Ohtani was born in Japan, his mother played badminton, and his father played amateur baseball and worked in a factory, and that lab-creation rumors are satirical[1:07:58]

Mike Rowe collaboration and American-made products

Theo says they are doing a project with Mike Rowe focused on small American "mom and pop" companies making Christmas gifts in the U.S.[1:09:59]
He frames it as an alternative to buying from large platforms, so buying a gift also supports the small maker as a second gift[1:09:56]
They note how difficult it is to find things made in America now, especially electronics, and mention a few exceptions like a meat company sourcing only U.S. product and a clothing company that makes textiles domestically[1:15:01]
Andrew observes that "Made in USA" goods tend to cost much more, making them hard to support despite good intentions[1:14:47]

Advanced Japanese sidewalks and hypothetical judging streets

Andrew describes Japanese sidewalks with kinetic tiles that store energy as people walk, contrasting it with a pothole near his house that has gone unfixed for nine years[1:11:02]
They imagine a future sidewalk that can tell if someone is gay or not and jokes about taking your son for a walk on that street to "see what happens"[1:12:02]

Smart toilets, health tracking, and fear of knowledge

Theo mentions a new toilet that uses a tiny camera to analyze stool, detect blood, and assess gut health and hydration, with a subscription fee for ongoing analysis[1:15:05]
Andrew says he doesn't want a camera in his toilet or his bathroom activities uploaded anywhere, joking about his father accidentally posting such clips[1:15:05]
They discuss full-body medical scans, with Andrew recounting friends who got scanned; one found a benign issue, and Andrew is unsure whether he wants that level of foreknowledge about potential health problems[1:15:42]
• Andrew compares it to preferring not to know a comment is coming at you; he'd rather live freely until it hits than live in constant anticipation of doom

Smart beds, hacked cars, and runaway tech dependency

AWS outage and overheated smart beds

Theo brings up an AWS outage that caused expensive smart mattress covers to overheat and get stuck upright, with no offline mode for users to adjust them[1:18:46]
Andrew imagines his dad yelling at his mom for sweating in bed, not realizing it's a tech issue rather than her fault, highlighting people's lack of control over tech glitches[1:18:36]

Smart cars and loss of control over movement

Theo says Craig Newmark warned about hijacking of connected products, such as all cars suddenly driving off a bridge under remote control[1:12:58]
Andrew notes his car updates maps without asking and speculates about future updates where cars force you to go to the doctor or dentist, removing choice[1:14:25]
He envisions a life where daily tasks and health obligations pop up automatically on bathroom mirrors and cars, gradually making self-directed decisions abnormal[1:14:43]

Isolation fantasies versus social nature and hunting

Sue from Life Below Zero as the extreme off-grid example

Andrew mentions Sue from "Life Below Zero" living alone in northern Alaska, refueling planes and living totally off the land as an example of true disconnection from tech and society[1:19:58]
He notes that until TV cameras arrive, she lives off clothes she makes or are given, self-generated power, and self-made food[1:19:28]

Cleaning animals and respect for people who do it

Andrew recalls his grandmother in North Carolina killing, cleaning, and cooking chickens herself, and says he doesn't think he could do that regularly[1:19:18]
He has been around deer being cut up after hunts and found it daunting, saying he's thankful for farmers and people who handle that part of the food chain[1:19:38]
Theo describes his brother in Utah posting that if people had nuisance squirrels, raccoons, or doves he would come remove them, leading to trapping and cooking raccoons and squirrels even in town settings[1:18:40]

Moderate drinking and social context

Andrew says he takes chunks of time off drinking but notices he almost never drinks alone at home; drinking for him is tied to being with friends and family at dinners or social events[1:20:24]
He and his wife don't do the common "glass of wine with home-cooked dinner" routine; it's more about communal socializing than daily habit[1:20:28]

Community, aging, and difficulty maintaining friendships

Losing time with friends as they marry and have children

Theo says most of his friends are married with kids, making it harder to see them, so he sometimes hangs with younger people because they're the ones still available[1:21:46]
He enjoys hanging around the Vanderbilt football team, eating in the players' cafeteria and "clowning" with them for an hour because of the high energy and camaraderie[1:22:02]

Andrew's older friend group and trips back home

Andrew notes that many of his current close friends are in their late 50s because their kids are grown, while his peers with young kids are too busy to hang out often[1:23:00]
He has started going home to Chicago about once a month to see his parents and childhood friends, feeling the importance as his parents age[1:24:27]
He acknowledges it's hard when life and responsibilities interfere with spending time with people you love, but he now deliberately builds trips home into his schedule[1:24:08]

Saudi Arabia, Riyadh comedy festival, and hypocrisy debates

Andrew's experience in Riyadh and reaction to backlash

Andrew says the Riyadh comedy festival was wild and the online backlash, particularly from within the comedy community, was even more intense[1:29:36]
He quotes Jimmy Carr saying he judges countries more on where they're going than where they've been, hoping Riyadh is moving toward progress and growth[1:30:14]
Andrew admits his own ignorant expectation that people there would be riding camels and fully covered, but he found mostly 27-28-year-olds in jeans and t-shirts excited to see them[1:30:40]
He found meeting fans afterward powerful and hasn't spent time arguing online about the festival, noting that everyone is a walking contradiction and hypocrisy abounds[1:29:46]

Theo's view on traveling to Muslim countries for shows

Theo says he has been asked to go to Qatar again and had a great time before, meeting locals who went to American universities and shouting "Go Ducks" about Oregon[1:33:42]
He points out that Muslim countries have their rules and doctrines and he doesn't feel it's his place to insist they be just like America, especially given his country's own government actions[1:40:13]
They joke about wearing local garments at hosts' invitation and about people claiming "they're all terrorists," countering that millions of residents can't all be that label[1:34:06]

Comedy community infighting, Marc Maron reference, and doing good

Attacks within comedy and differing responsibilities

Andrew dislikes comics attacking each other over performing in places like Saudi Arabia, calling it strange and a detriment to comedy[1:31:34]
He says his responsibility is to spread love and comedy, entertain people, and live his life, recognizing that the public's idea of his responsibility differs from his own[1:32:12]

Marc Maron's joke about Theo and boundaries in specials

Theo mentions a Marc Maron special where Maron joked that Theo would interview Hitler, and notes this was framed in media as part of larger drama[1:36:57]
Andrew, who knows Maron from the Comedy Store, says Marc likes to start drama and talk shit, but questions the necessity of including a colleague by name in a special[1:37:25]
He suggests a more respectful approach would have been to run the joke by Theo first or at least give a heads-up[1:39:35]

Ho Ho Homers charity and focus on positive impact

Andrew describes a fundraiser he is doing called "Ho Ho Homers" at LA City Valley College to benefit Southern California Special Olympics, where fans can hit home runs off celebrities[1:38:33]
He says doing good, feeling good, and uplifting others and the comedy community matters more to him than internet drama and opinions[1:38:45]

Hypocrisy, tech, UFC at the White House, and government

Everyday hypocrisy and impossible purity

Andrew points out that critics likely tweet from phones made with mined lithium and wear clothes made under questionable conditions, saying unless you live like Sue in Alaska, you don't have completely clean hands[1:43:01]
He argues that because we are all implicated in global systems, people should be cautious about throwing stones at others for perceived moral compromises[1:43:11]

UFC growth, WWE merger, and event at the White House

They discuss a planned UFC event on the South Lawn of the White House to mark the 250th anniversary of the U.S., noting it shows how government spaces are becoming performance venues[1:44:51]
Nick, Theo's producer, notes UFC and WWE merged into TKO with a major agency, illustrating large entertainment conglomerates[1:47:03]
They credit UFC's big growth during the pandemic to Dana White's decision to keep hosting fights when other sports shut down, with reported massive increases in social following and pay-per-view sales[1:48:10]
Andrew recalls an ESPN clip where Joe Rogan debated a boxing promoter by arguing that MMA represents actual full fighting, whereas boxing is a limited, "silly agreement" using only hands[1:48:27]

AI in entertainment, Back to the Future pizza, and designer humans

Future of AI-generated media and live performance

Andrew says a golf simulator company told him future tech will simulate entire courses with matching temperature, smell, and social presence, making it feel like you are truly there[1:51:09]
He believes live entertainment will still matter because people will want real human interaction, even as AI creates on-demand movies tailored to specific prompts like odd action plots[1:51:13]

Back to the Future hydrator pizza and artificial food

Andrew references the tiny dehydrated pizza in Back to the Future II that becomes a full-size pizza in a "hydrator," saying that kind of tech is likely coming[1:53:17]
He predicts future pizzas will taste like real pizza but not actually be pizza, paralleling modern plant-based meat substitutes that mimic meat without being meat[1:54:53]

Animal cannibalism and human eugenics parallels

They read that female praying mantises often eat males during or after mating and that male raccoons sometimes kill and eat young so females return to heat sooner[1:56:33]
Andrew analogizes this to speculative human futures where people might engineer children to exact specs and discard imperfect ones, like a dark sci-fi scenario[1:57:51]

Government shutdown confusion and privatization

Theo's confusion about a government shutdown

Theo admits he doesn't fully understand what it means when people say the government is shut down and wonders if "all of it" shuts down[1:42:56]

Privatization of public services and post office decay

Andrew jokes that everything is privatized now, recounting visiting a post office where birds were fighting over a box and an employee was spraying them with Lysol[1:43:36]
He calls the post office a halfway house or recovery center for mail and argues that public institutions are increasingly shells for private companies[1:43:36]

Kids, legacy, doing good, and coin pusher metaphor

Accepting a life without biological children

Theo asks Andrew if he and his wife are done trying to have a child; Andrew says yes, given their age and their sense of acceptance[2:01:56]
Andrew says his "children" have become his community: younger comics he mentors, producers, editors, and people he helps through charity and support[2:02:34]
Theo reflects that if he doesn't have kids he could focus more on serving his existing family and making up for closeness they lacked when he was young[2:03:00]

Coin pusher game as metaphor for unseen payoff

Andrew describes the arcade game where you drop coins onto a sliding pile hoping to push a jackpot off the edge, noting most players never get the big flush[2:04:00]
He likens life to loading up coins for someone else to eventually benefit, suggesting that doing good may reward future people rather than yourself, which he finds meaningful[2:04:15]

Everyone as scared kids, empathy, and change

Little kids in big shells and universal insecurity

Andrew says he has learned that everyone is essentially a little kid in a big adult shell pretending to know what they're doing, regardless of status or intelligence[2:00:08]
He argues that remembering this makes it easier to see that no one is truly above others and can encourage empathy instead of judgment[1:59:19]

Change, politics, and letting people live freely

Andrew says he is socially progressive and wants people to live their ultimate freedoms as long as they are not harming others, regardless of identity or orientation[1:56:45]
He argues that infighting and hatred are pushing society into a negative spiral and that education, conversation, and empathy are better paths to growth[1:56:09]
Theo mentions thinking about all the grace God has shown him in close calls and support, which shapes how he views others' struggles and his own mistakes[1:58:18]

Media distortion of Theo's older clips

Theo says after the special controversy, some outlets resurfaced old emotional podcast clips as if they were new, misleading viewers and flooding his inbox[1:59:48]
He found it odd that even positive groups were posting outdated clips without dates, contributing to a confusing public narrative about him[1:59:36]

Closing plugs and future creative projects

Andrew's shows, special, and animated series concept

Theo lists Andrew's shows "No Bad Lies," "Whiskey Ginger," and "Bad Friends" and his special "White Noise" as things listeners should check out[2:05:54]
Andrew says "White Noise" is on Hulu in the U.S. and on Disney+ internationally under the same corporate umbrella[2:06:08]
He describes an animated show they sold to Hulu set in high school where all young people are bugs and adults are humans, with Bobby as a roly-poly and Andrew as a lightning bug, based on stories from their youth[2:07:02]
He directs people to andrewsantino.com for tour dates and invites Theo back on "Bad Friends" anytime[2:07:06]

Final encouragement and rest

Andrew tells Theo to take time for himself, center, rest, and get away from the bullshit for a while after the intense period he has gone through[2:05:40]
Theo acknowledges he needs to keep rest and self-care as a focal point and thanks Andrew for checking in and caring about how he is doing[2:05:46]

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

High-pressure performances are rarely just about the moment on stage; they are shaped by mental health, external stressors, and invisible production details, so you must plan for your psychological state as carefully as your material.

Reflection Questions:

  • • What external stressors or mental health factors tend to affect your performance or decision-making the most, and how could you address them before big moments?
  • • How might your preparation change if you treated your next important presentation or event as something that needs emotional readiness, not just technical readiness?
  • • What specific routine could you create in the 48 hours before a high-stakes situation to put yourself in a calmer, more focused headspace?
2

Online narratives are often distorted, decontextualized, and driven by attention rather than truth, so choosing what you engage with (and what you ignore) is a critical part of protecting your sanity and focus.

Reflection Questions:

  • • Which types of online content reliably make you feel anxious, defensive, or distracted, and how often are you voluntarily exposing yourself to them?
  • • How could you redesign your media diet so that it supports your goals and values instead of constantly pulling you into drama or outrage cycles?
  • • What is one concrete boundary you could set this week (for example, time limits, muting certain topics, or avoiding comment sections) to reduce harmful online noise in your life?
3

Community and friendship require intentional effort as life circumstances change; you cannot rely on proximity or convenience once people have careers, marriages, and kids, so you have to deliberately build in time and rituals.

Reflection Questions:

  • • Which important relationships in your life have quietly drifted because you assumed there would always be more time to reconnect?
  • • How might your calendar look different if you treated time with family and close friends as non-negotiable commitments rather than "optional" extras?
  • • What recurring ritual (monthly visits, weekly calls, shared hobbies) could you start in the next month to keep at least one key relationship strong despite busy schedules?
4

Technology that promises convenience can quietly erode autonomy and resilience if you let it make all your decisions, so it's important to stay conscious of where you still want to retain friction, choice, and analog skills.

Reflection Questions:

  • • In what areas of your life are you most tempted to let apps, algorithms, or smart devices decide for you instead of making your own deliberate choices?
  • • How would your habits change if you assumed that every new layer of automation required a clear justification about what you might be giving up in return?
  • • What is one domain-navigation, scheduling, health, or something else-where you could intentionally rely a bit less on tech this month to keep your own capabilities sharp?
5

You may not get the exact life path you imagined (such as having biological children), but you can still live a deeply meaningful life by redirecting that energy into mentoring, community, and long-term contributions that outlast you.

Reflection Questions:

  • • Where are you holding onto a rigid picture of how your life "should" look, and how might that be blocking you from seeing other valuable ways to matter?
  • • Who in your orbit-coworkers, younger friends, neighbors, relatives-could benefit if you treated them with the same care and intentionality you'd give to a child or mentee?
  • • What is one contribution you could start or join this year (a project, cause, or relationship) that will likely benefit people long after you're gone?
6

Everyone is essentially a scared, imperfect kid in an adult shell trying to figure it out, so leading with empathy instead of instant judgment is usually the wiser and more accurate stance.

Reflection Questions:

  • • Think of someone whose behavior frustrates you-what might they be afraid of or insecure about that you're not seeing on the surface?
  • • How could reminding yourself that "no one fully knows what they're doing" change the way you respond to mistakes, both your own and other people's?
  • • What is one conflict or grudge you're holding that might soften if you consciously reframed the other person as a confused human rather than a villain?
7

Hypocrisy is baked into modern life because almost all of us benefit from flawed systems, so moral certainty and public shaming are often less honest than humble self-scrutiny and trying to do a bit more good where you actually stand.

Reflection Questions:

  • • In which issues are you most tempted to judge others harshly without fully acknowledging your own complicity in related systems or conveniences?
  • • How might your tone or tactics change if you approached disagreements with the assumption that you and the other person are both compromised in different ways?
  • • What is one small, concrete way you could reduce your own hypocrisy this month-through a purchasing decision, time commitment, or personal habit-rather than focusing on what others should do?

Episode Summary - Notes by Spencer

#621 - Andrew Santino
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