Whether pain fuels great writing, and Grant's view that pain is a beginning, not an end.
Where it comes up 9
Within this theme 58
Concepts 12
- Sincerity vs Seriousness
From Alan Watts' jester: meet life's obstacles sincerely, with respect, but don't take them so seriously that they drown you.
- Stoicism
Discussed via Ryan Holiday and Seneca as a daily practice that prevents the hell we create on earth by lacking tools to handle loss and volatility.
- Fatalism Without Desire
Grant's distinction: a hopeless protagonist who still wants something (Dostoevsky's Underground Man, Fallada's drinker) is compelling; one who has given up all desire (Dazai) is not.
- Life Without a Cheat Code
The lesson Tamir draws from Recursion: no amount of rewinding and rebuilding timelines keeps things from going wrong. Existence can't be engineered or optimized to avoid pain, and beauty…
- Pain as Contrast
Ian's view that good days feel good because of recent bad ones. If everything were good, it would become the new baseline and stop feeling good.
- Sad Clown
The trope, and real pattern, of the person who is always 'on' and lights up every room while suffering privately. It comes up through Dazai's clowning and the death of Robin Williams.
- Familiar Pain
The tendency to keep choosing a known source of stress and unhappiness every day rather than step into the unknown, because we are creatures of habit and the unknown feels scarier.
- Pain as Beginning
Grant's answer to whether pain fuels great writing: pain is not the end but the beginning; what matters is what you do with it, ideally rising above it with humor.
- Existential Angst
The self-centered 'I hate the world' brooding Grant associates with young readers and with No Longer Human and The Catcher in the Rye.
- Pain plus resistance equals suffering
Ian's formula: suffering comes not from pain or desire itself but from resisting what is; he uses it to disagree with the idea that desire causes suffering.
- Buddhism
Raised via the teaching that life is suffering and that suffering comes from desire; Ian partly disagrees, locating suffering in resistance.
- Trough of sorrow
Startup-world term for the slump after launch excitement meets reality; Tamir's mentor laughed at him for thinking there was only one.
Books 9
- Recursion
Sci-fi novel Tamir had just finished. Researcher Helena builds a chair that records memories, and a billionaire funds it. Combined with a deprivation tank that briefly kills the user and…
- Man's Search for Meaning
Raised as a non-fiction touchstone on choosing your response to circumstance. Tyler read it in university; for him, as a closeted teen who felt locked into a bad fate, it taught that…
- No Longer Human
Dazai's quasi-memoir about a man who clowns, drinks and ends in a double suicide. Tamir likes it; Grant finds it too self-indulgent and without desire.
- Dhammapada
Buddhist scripture Tamir cites (paraphrasing its opening) as saying you suffer because you desire; Ian counters that resistance, not desire, creates suffering.
- The Flowers of Buffoonery
Dazai's novella about a man recovering in a sanatorium after a failed double suicide. Tamir notes it was written before No Longer Human yet works as its sequel and has a more hopeful tone.
- Notes from Underground
Grant compares it to No Longer Human: an equally negative narrator who still aspires, absurdly, to be part of a barroom brawl so his life won't feel futile.
- Catch-22
Heller's war novel about the horror of war, told with irony and sarcasm. Grant's model for laughing at pain in order to stay human.
- The Drinker
A very depressing novel about a man who takes one drink and becomes an alcoholic. For Grant it still has desire, unlike Dazai.
- The Grapes of Wrath
Cited by Grant as great literature that treats pain as a beginning, not an end.
People 9
- Seneca
Cited as a Stoic whose life was riddled with tragedy (killed by Nero, family deaths) and who wrote consolation letters, including one to his mother from exile.
- Blake Crouch
American science-fiction novelist, author of Recursion, which Tamir had just finished reading. Its lesson that life can't be engineered to avoid pain anchors the second half of the…
- Osamu Dazai
Japanese novelist of No Longer Human and The Flowers of Buffoonery. For Grant he is the example of dwelling on pain until there is no desire left; Tamir defends the book's purposeful…
- Viktor Frankl
Author of Man's Search for Meaning. Brought up as a non-fiction source on controlling only your response to circumstance; for Tyler, Frankl taught the same lesson as dark fiction: finding…
- Ryan Holiday
Tamir saw him speak in Vancouver a few weeks earlier, where Holiday told the story of a philosopher asking the Oracle of Delphi about wisdom and being told to converse with the dead…
- Robin Williams
Logan's real-life example of the sad clown: always high-energy around people, a 'well-spring of joy', but a fairly sad man behind closed doors, which is why his death shocked people.
- Fyodor Dostoevsky
Russian novelist; Grant contrasts the absurd but aspirational narrator of Notes from Underground with Dazai's hopeless protagonist.
- Joseph Heller
Author of Catch-22, whose ironic humor about war is Grant's model for laughing at pain.
- John Steinbeck
Author of The Grapes of Wrath, cited by Grant as great literature that does something with pain.
Quotes 10
People would rather choose familiar pain than step into that unknown.
Life with a cheat code isn't life. Our existence isn't something to be engineered or optimized for the avoidance of pain.
All I'm doing is creating suffering. Pain plus resistance equals suffering.
The Stoics realized that their daily practice is preventing the hell which exists on earth.
It taught me to kind of laugh while my feet are on fire.
Pain can be bodily also. Pain can be fantasy. Pain can be imagination. For me, pain is nothing to brag about. You have it. You, with your own intelligence and understanding, you go through it.
A lot of times as humans we get to a point where we must shed a skin or we will continue to suffer.
Stop trying to make the bad days good and stop living too much in the good days, and just allow yourself to be with the full experience of life.
I think pain is not the end. I think pain is more like the beginning. There is pain, and there is what you do with it.
Choose your struggle or you'll be assigned one.
Insights 8
- Resistance, not desire, creates suffering
Ian disagrees that desire causes suffering: you can hold massive desire as long as you're not dependent on reaching it; the suffering comes from resisting what is.
- Dark stories hold the profound lessons
Most songs are about love, heartbreak or sex, but great books are drawn to darkness, and inside the darkness, if you look, is black humor that teaches you how to survive.
- Fake it long enough and you pay
Clowning yourself for others from a place of pain, rather than natural humor, eventually reaches a precipice where something gives. Dazai's novella and the sad-clown pattern show the bill…
- Futile aspiration beats no desire
A protagonist who still wants something, however absurd, is more compelling than one who has given up wanting anything.
- Good days need bad days
The beauty and the pain are each meaningless without the other. Older people tend to have absorbed this, while younger people still try to avoid all pain and do life 'by the book'.
- Pain is a starting point, not a muse
Dwelling on pain until it becomes an obsession leads to Dazai's dead end. Pain is fuel for becoming something, and humor lets you stand above it.
- Pain turned into art
Kafka never resolved his pain, but turning it into art was his 'special species of happiness'; even unresolved suffering can leave something beautiful.
- Closing off the lows closes off the highs
The highs feel good because the lows feel low; mask and distract from the losses and you also lose the capacity to experience the wins, and refusing to play at all is dying at 30.
Practices 3
- Moment-by-moment yoga
Treat everyday frustration as the mat: when resistance arises, close your eyes and say aloud 'I'm in resistance, I'm wanting things to be different than they are, I'm being impatient', then…
- Laugh at your pain
Rather than squeezing pain for all it's worth, look at it and try to laugh at it, to rise above it.
- Reframe pain mid-effort
When a run (or a day) feels terrible, remind yourself that this is what will make the good ones feel good. Stop trying to make bad days good, don't cling to good ones, and allow the full…
Stories 6
- Mentor laughs at 'one trough of sorrow'
In his early twenties, after surviving a gut disease, a hospital stay, and a breakup, Tamir told a business mentor in his 50s he'd come through the trough of sorrow. The mentor laughed…
- Seeing Ryan Holiday in Vancouver
The week before, Tamir saw Ryan Holiday speak in Vancouver, contrasting religion's focus on avoiding hell after death with the Stoics' daily practice for avoiding the hell created on earth.
- Seneca's consolations amid tragedy
Tamir recounts that Seneca lost family members, was exiled and eventually killed by Nero, yet made consolation his role, writing to the bereaved and telling his mother from exile not to…
- Mishima dismissed Dazai
Tamir describes Dazai and Mishima as UFC-like rivals; Grant recalls reading that Mishima was dismissive of Dazai as a person, saying there was nothing to get from him. Both admit they may…
- Resistance while cooking dinner
The day before, frustrated in his kitchen that his content wasn't reaching enough people, Ian recognized it as his 'mat': he closed his eyes and said aloud that he was in resistance and…
- The painful run after leg day
The day after heavy squats, Ian dreaded his run, and his calves and legs felt horrible. Mid-run he reminded himself that the days he flies only feel great because of runs like this one. If…
Films, music and art 1
- Eli
Colin's award-winning short film, based on a Holocaust survivor he met. As a boy in Hungary in the summer of 1944 the man was separated from his mother and little brother at Mengele's…








