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This book made me quit my job

2023-04-13 · Long video (solo, talking head or whiteboard) · Ali · recording, 14:10 · watch on YouTube

Topic: Work and career (also: Mindset, motivation and happiness, Goals, purpose and life design, Productivity and time) · mode: List of tips or lessons · tags: Lesson from a book, His medical past, Sponsor segment present, Family

In a Book Club episode on Paul Millerd's The Pathless Path, Ali gives ten points from the book: the default path versus the pathless path, the certainty and prestige traps, work as a craft, the "ought to" self, fear-setting, sabbaticals, experiments in living, being a little underemployed, and meeting an uncertain path with curiosity and wonder.

What is said

The parts of the video and what is said in each (★ — how much it matters to the video).

00:00:00 — Two friends, John on the default path and Jane on the pathless path

00:00:58 — Book Club episode on The Pathless Path and why it mattered to Ali

  • ★★ This Book Club episode, in the ongoing series Ali has run for three years distilling highlights from his favourite books, is on Paul Millerd's The Pathless Path. — 00:00:58 · Book Club
  • ★★★ Ali calls The Pathless Path one of the most impactful books he read last year (2022): it gave him the terminology, a few mental models and almost permission to explore a non-traditional career path. — 00:01:12
  • ★★ Ali suggests The Pathless Path to anyone who has been feeling lost in their career or directionless in life and thinks that is a bad thing. — 00:01:27

00:01:41 — Point 1: default path versus pathless path; Ali's uncertainty after leaving medicine

  • ★★ The default path, Ali explains, is what we are told when young: go to a good school, get good grades and then go to a good college or university. — 00:01:41

  • ★★ Paul Millerd (quoted): Paul Millerd defines the pathless path as an alternative to the default path: an embrace of uncertainty and discomfort, a call to adventure in a world that tells us to conform. — 00:01:56

    “an embrace of uncertainty and discomfort it's a call to adventure in a world that tells us to conform”

  • ★★ When Ali took a break from the default path of medicine to become an internet entrepreneur and YouTuber, he was racked with uncertainty; when his mum asked about his plan, he said he honestly did not know. — 00:02:26 · Ali Abdaal's mother

  • ★ Every entrepreneur, creator and author Ali has spoken to, on his podcast or in real life, has related to the uncertainty of doing your own thing. — 00:02:47

00:03:17 — Point 2: the certainty trap

  • ★★ Ali describes the certainty trap: we often put up with not enjoying our jobs in exchange for some certainty, valuing certainty and security over following our dreams. — 00:03:17
  • ★★ With a family, a mortgage and bills you have to optimise for security to an extent, Ali says, but young people without financial dependents still tend to default to the default path. — 00:03:46
  • ★★ Paul Millerd (quoted): Paul Millerd writes that with so many career options it can be tempting to pick a path that offers certainty rather than do the harder work of figuring out what we really want. — 00:03:46

00:04:15 — Point 3: the prestige trap

  • ★★ Paul Graham (quoted): Paul Graham, founder of the startup incubator Y Combinator, says prestige is a powerful magnet that warps even your beliefs about what you enjoy. — 00:04:15
  • ★★ In a prestigious career, Ali says, you easily convince yourself you enjoy the work when what you actually enjoy is the social status, the accolades and the admiration. — 00:04:45
  • ★ Ali says he would struggle to explain what he does for a living: he used to be a doctor and disappointed his mum when he became a YouTuber. (playful) — 00:04:45 · Ali Abdaal's mother

  • ★★★ Ali's takeaway on the prestige trap: whenever he makes a decision that also happens to be in line with prestige, he needs to be very careful about his motives. — 00:05:14

    “the point is prestige is a trap.”

00:05:21 — Point 4: our modern relationship with work; work as a craft

  • ★★ Andrew Taggart (quoted): The philosopher Andrew Taggart says meaning and fulfilment come from treating our work like a craft, an end in itself and a form of creative expression. — 00:05:43
  • ★★★ If you value your work for its own sake rather than striving extrinsically for some reward, Ali says, you are way more likely to find meaning and fulfilment in it. — 00:05:43

00:06:05 — Sponsor read for Surfshark VPN

00:07:21 — Point 5: overcoming the "ought to" self

  • ★★ The inner "should" or "ought to" voice, Ali says, helps us follow through on our commitments but can stop us from making important changes to our lives. — 00:07:40
  • ★★ We need not eliminate every "should", Ali says, but should recognise their power: if a risk such as starting a business does not work out, the "should" self will help get you out of the mess. — 00:08:09
  • ★★ Ali presents Tim Ferriss's fear-setting exercise from The 4-Hour Workweek, which Paul Millerd discusses: seven simple journaling prompts that take only a few minutes, not hours. — 00:08:09 · Tim Ferriss, The 4-Hour Workweek

00:08:16 — Point 6: the fear-setting exercise

  • ★★★ Whenever he is at a crossroads in life, Ali looks up Tim Ferriss's fear-setting post and journals through it for about half an hour; usually his fears turn out overblown and the worst case not that bad. — 00:08:38 · Tim Ferriss

00:09:08 — Point 7: the power of sabbaticals

  • ★ Ali breaks off filming to go to date night with his girlfriend and resumes the video the next day. — 00:09:08
  • ★★★ Ali says quitting your job to do your own thing is probably out of reach for most people, but taking a sabbatical, a planned break from work, is within reach for many. (hedged) — 00:09:08
  • ★★ Paul Millerd (quoted): Paul Millerd says that on a sabbatical people first become aware of their own suffering. — 00:09:08
  • ★★ On a sabbatical curiosity re-emerges, Ali says: friends of his on sabbaticals played video games for the first few weeks, then wanted to dive into projects of their own. — 00:09:39
  • ★★ After a sabbatical people usually do not go straight back to work, Ali says; for him too, reflection led to asking how he really wants to spend his life and what his core values are. — 00:10:08
  • ★★ Ali's test for a job: after a holiday from work of a week or two, do you return excited to get back to it, or with a sense of dread? — 00:10:37

00:10:52 — Plug for the Sunday Snippets email

  • ★★ John Stuart Mill (quoted): In On Liberty (1859), John Stuart Mill writes that the worth of different modes of life should be proved practically, arguing that societies need people to conduct experiments in living. — 00:11:07

00:11:17 — Point 8: experiments in living

  • ★★★ Ali's rule: if he has even a vague curiosity about living in a certain way, it is worth running the experiment for a few days, a week or a month to see whether his hypothesis holds. — 00:12:05

  • ★★ Amos Tversky (quoted): Amos Tversky said the secret to doing good research is to always be a little underemployed: you waste years by not being able to waste hours. — 00:12:05

    “the secret to doing good research is to always be a little underemployed.”

00:12:20 — Point 9: the underemployment edge

  • ★★ Ali says he does not follow Tversky's advice and knows that is suboptimal: he should have more empty space in his calendar to think more creatively. — 00:12:34
  • ★★★ Ali's main takeaway from The Pathless Path: instead of fearing that your path is uncertain and not knowing where you will be in five or ten years, approach it with curiosity and wonder. — 00:13:03

00:13:10 — Point 10: curiosity and wonder; sign-off

  • ★★ As long as he operates from curiosity and wonder rather than fear, Ali trusts that the financial side will take care of itself or that something interesting will come about. — 00:13:34

Threads in this video

Where the stories that moved here went next

Mentioned

Central: default path · Paul Millerd · The Pathless Path

Also: People: Ali Abdaal's mother · Amos Tversky · Andrew Taggart · John Stuart Mill · Paul Graham · Tim Ferriss

Projects: Book Club

Works: On Liberty · The 4-Hour Workweek

Organizations: Y Combinator

Concepts: core values · digital nomad · experiments in living · fear-setting

Also centred on The Pathless Path: 15 Incredible Books to Read in 2026 · How to figure out what to do with your life #shorts

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