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How to Find a Career You Genuinely Love

2026-06-11 · Podcast or interview · Ali, Paul Millerd · recording, 1 h 18 min · watch on YouTube

Topic: Work and career (also: Money and investing, Relationships and personal life) · mode: Conversation and interview · tags: Lesson from a book, His medical past, His own products discussed, Family, Sponsor segment present

Ali and Paul Millerd, author of The Pathless Path and Good Work, lay out a ten-step roadmap for leaving a prestigious default-path career without a perfect plan: notice the misalignment, face the shame, run the numbers, take the leap, hack a living, follow your energy, declare retirement from bad work, handle the people around you and keep playing the infinite game.

What is said

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

00:00:00 — A case study of quitting a job without a plan, recorded with Paul Millerd in Hong Kong

  • ★ When Paul Millerd visited Ali in Hong Kong, they sat down for a long conversation and broke quitting the default path into a ten-step roadmap. — 00:00:00 · Hong Kong

00:00:41 — Step 1: win the prestige game; Paul's McKinsey and MIT career and what he gave up

  • ★★ Paul Millerd says he got sucked into prestige because prestige and high salaries are a really useful outcome when you don't know what you want to do. — 00:01:09
  • ★★ Paul Millerd worked at McKinsey making only 50 grand a year, then spent two years in grad school doing an MBA and a master's in systems engineering at MIT. — 00:01:33
  • ★★ Ali could never take seriously books by professional vagabonds who left the default path early; Paul Millerd, who gave up fancy credentials, was relatable to him. — 00:02:38
  • ★★ Paul Millerd estimates that leaving his career cost him about a million dollars in income over eight and a half years, and says he feels nothing about it because he got back a life he wanted to live. (hedged) — 00:03:36
  • ★★ Ali's homework for anyone thinking of leaving the default path: write down which version of the prestige game you have played so far, and which one you still lean towards in deciding what to do with your life. — 00:04:11

00:04:39 — Step 2: spot the misalignment between your work and your own values

  • ★★ Paul Millerd was constantly restless in his career and never stayed in a job, leaving each one after between 12 months and two years. — 00:05:33
  • ★★ Paul Millerd: About nine years into his career, assessing himself against the goals he set in grad school, Paul Millerd found he was grumpy and felt in a battle with his boss. — 00:06:06
  • ★★★ Ali suggests identifying what you said mattered to you three or five years ago and asking whether your current work moves you towards the person you wanted to become or away from that person. — 00:06:46

00:07:27 — Step 3: face the shame; the bad egg, guilt versus shame, Ali's shame at leaving medicine

  • ★★ Paul Millerd: From conversations with people who secretly dislike their work, Paul Millerd says people feel an immense amount of shame about their relationship to work. — 00:08:41
  • ★★ Paul Millerd: In his first book Paul Millerd uses Ben Hunt's idea of the industrially necessary egg: jobs are standardised to fit the economy, and someone who leaves an industrially necessary job feels like a bad egg. — 00:09:50
  • ★★ For years after deciding to leave medicine, Ali felt shame about it and asked himself whether he was a bad person for leaving. — 00:10:18
  • ★★ Having spoken to many corporate lawyers, management consultants and bankers, Ali says they too feel shame about leaving that path. — 00:10:47
  • ★★ Paul Millerd separates guilt from shame: guilt is feeling bad for not doing something, carries responsibility and can be good; shame is feeling that you are a bad person. — 00:11:21
  • ★★ Paul Millerd: After quitting, Paul Millerd felt like a bad person; he was soaking up the insecurity of the people around him, and much of his writing was permission to himself to feel better about it. — 00:12:01

00:12:44 — Sponsor read for Wispr Flow

00:14:30 — Criticism from people who stay, and low-grade suffering at work

  • ★ Friends still in medicine tell Ali that perhaps half the people they speak to are fans of his and the other half really hate him. (hedged) — 00:14:44
  • ★★ Paul Millerd had not considered self-employment a viable path until about six months before he quit his job. — 00:15:09
  • ★★ Paul Millerd says people dismiss low-grade suffering at work, such as an aggressive boss who embarrasses them, because it is the default script. — 00:15:38
  • ★★ Ali says the story that keeps people in a job far longer than they should stay is that they should be grateful to have a job at all. — 00:16:03

00:17:07 — Interlude: are you actually wired for this; proof of energy

  • ★★ Ali says living on the pathless path is not for everyone: a certain kind of person, himself included, eventually has to carve their own path. — 00:17:07
  • ★★ Paul Millerd advises doing a pro bono freelance assignment before leaving a job; his own, for a small Boston startup, showed him there was much more to learn working on his own. — 00:17:56
  • ★★★ Paul Millerd advises trying things before quitting: see whether you can make money or do a project on your own, notice what you do with free time, network, and start and host things. — 00:18:56
  • ★★ Paul Millerd: Before quitting, Paul Millerd ran a coaching business and an online course on résumés, making a little money in several ways. — 00:19:41

  • ★★ Taking up Paul Millerd's phrase, Ali suggests looking for proof of energy rather than proof of success: evidence from your own life of experiments you have run over the years. — 00:20:03

    “proof of energy rather than necessarily proof of success”

  • ★★ Ali finds that the people who most want the pathless path, and who thrive on it, tend to be the ones who were a little weird when they were younger. — 00:20:42

00:21:20 — Step 4: run the numbers; living on 25% of your income

  • ★★ Paul Millerd has always known he needs little money and few possessions, which made quitting far less scary for him. — 00:21:30
  • ★★★ Paul Millerd's prompt for people in jobs: imagine you could quit and not work for a year while getting 25% of your current income; how do you feel? — 00:22:08
  • ★★ Paul Millerd: If living on 25% looks reasonable, Paul Millerd says, the question changes from how to replace your salary to how to hack a living on 25% of your income for the next year, going back to a job if you can't. — 00:22:34
  • ★★ If living on a quarter of your income feels doable, even a relief, Ali says that is a very strong sign that maybe the time is right to do your own thing. (hedged) — 00:23:12
  • ★★ Paul Millerd did not match his old salary until his sixth year of self-employment. — 00:23:42
  • ★★ Paul Millerd leads people through questions such as the lowest income over the next year they would count as success, and how many months they are comfortable earning nothing. — 00:24:25
  • ★★ Paul Millerd asks why anyone would be good at self-employment with no practice at it; eight and a half years in, he feels he is only getting his bearings. — 00:24:50
  • ★★★ Ali says aiming to replace your salary when you quit is a very high bar; if you can get by on 10 or 20 grand, or have a year's savings to dip into, the game becomes much easier. — 00:25:19
  • ★★ Replacing a six-figure law salary within six to twelve months is hard, Ali says: it takes time to train up for anything, as a neurosurgeon needs a decade of training. — 00:25:49
  • ★★ Paul Millerd: Asked how much savings you need before quitting, Paul Millerd reframes it as questions: how long will you go without making money before calling it a failure, and what amount would make you extend that from six months to 12 or 18? — 00:26:16
  • ★★ Paul Millerd advises running the numbers before quitting: he is shocked at how few people know what they spend. — 00:26:16
  • ★★ Paul Millerd: After quitting, Paul Millerd analysed his spending and found he could live on $3,500 a month, so his savings could fund a year. — 00:27:00
  • ★★ Ali calls Paul Millerd's advice practical: run the numbers on how much you actually need to live on, and lower the bar to buy yourself time to explore. — 00:27:00
  • ★★ Paul Millerd made around $800,000 in his eight and a half years on his own, about the same as in his eight employed years. (hedged) — 00:27:30

00:28:08 — Step 5: take the leap without a perfect plan; a sabbatical instead of a business

  • ★★ Paul Millerd: While employed, Paul Millerd devoured Tim Ferriss's podcasts and everything Derek Sivers said, but it never occurred to him that he could do anything other than his job. — 00:28:41 · Derek Sivers, Tim Ferriss
  • ★★★ Paul Millerd says the idea that you need a plan after taking a leap holds far too many people back; his own plan, freelance consulting, lasted about six months. — 00:29:09
  • ★★★ Paul Millerd thinks people should take a sabbatical rather than start a business: a three-month sabbatical once in an adult working life of about 500 months is a tiny share. — 00:30:41
  • ★★ Paul Millerd: The task of a three-month sabbatical, Paul Millerd says, is to get back in touch with yourself; he recommends taking it in your 30s, once you have some experience of work. — 00:31:06
  • ★★ Ali says probably 90% of Lifestyle Business Academy students are building a business alongside their day job, while about 10% have taken a break of two to four months from work to do it. (hedged) — 00:31:49 · Lifestyle Business Academy

00:32:33 — Step 6: hack a living; buying years, financial confidence, savings as a gift from your former self

  • ★★ Paul Millerd says everyone prices in the visible costs of the pathless path, such as unpredictable income, uncertainty and fear, but cannot see its hidden benefits. — 00:32:47
  • ★★ Paul Millerd's hidden benefit of going it alone: once he had made $100 on his own he knew he could make a thousand, then ten thousand, and felt excitement, ownership, autonomy and belief in himself. — 00:33:09
  • ★★ Paul Millerd: In his first year after quitting, Paul Millerd's nine months of freelancing funded his lower cost of living for a year without touching his savings, so he kept buying years. — 00:33:38
  • ★★★ Ali says quitting is about running one experiment after another: try three months, review the money you made and how you feel, then try another three months or six. — 00:35:03 · experimental mindset
  • ★★ When Ali decided to leave medicine, in 2021 as he dates it, he thought of it as a one-year break, a kind of sabbatical from medicine, after which he would see how it went. — 00:35:32
  • ★★ Ali says that in the grand scheme of things no one really cares about a gap in your résumé, though people worry about it a lot and it holds many back. — 00:35:32
  • ★★ Paul Millerd's main source of income has changed five or six times: freelance consulting at first, then an online course teaching consulting skills, and two years ago, for the only time, book sales. — 00:36:08
  • ★★ Paul Millerd says your first $1,000 earned on your own warps your mind, and jokes that it beats a $200,000 salary: it shows you that you can just do stuff. — 00:37:02
  • ★★ Paul Millerd has generated over a million dollars in revenue in eight years; he would have made more on his previous path, but the confidence of earning it himself is profound. — 00:37:24
  • ★★ Paul Millerd now has some passive income sources, his own basic income that funds his experiments and his continued betting on himself. — 00:37:53 · passive income

  • ★★★ Ali takes from his friend Dickie Bush the idea of thinking about financial confidence instead of financial security. — 00:37:53

    “instead of thinking about financial security, instead think about financial confidence”

  • ★★ Reframing your aim from financial security to financial confidence, confidence in your own ability to figure it out and make money, lets you take leaps without huge savings, Ali says. — 00:38:34

  • ★★★ Ali says dabbling with entrepreneurship is about learning the skills of independent income generation, which an employee never learns. — 00:39:03
  • ★★ Ali says the hardest part of building a business is winning the work, getting paying clients, which is a series of skills; doing the work is easy to figure out, especially with AI. — 00:39:33
  • ★★ Last year (2025) Ali's team ran the 1K Challenge, a six-week live programme over the summer to help people make their first $1,000 online, and a number of participants made $1,000 or more. — 00:39:33
  • ★★ Ali's student Kelsey, who had worked fancy tech jobs, made her first $1,000 in the 1K Challenge, joined the Lifestyle Business Academy and has made $40,000 in the last few months without quitting her day job. — 00:40:02 · Lifestyle Business Academy
  • ★ A friend of Ali's with about $80,000 in savings and a $200-a-month mortgage is so terrified of dipping into her savings that for five years she has not done her own thing. — 00:40:56
  • ★★ Paul Millerd says money on a spreadsheet does not solve emotional problems. — 00:40:56
  • ★★ Paul Millerd describes the paycheck reality: you count as a good person, a worker contributing to society, while you earn a paycheck, and as a bad person if you don't. — 00:41:40

  • ★★★ Paul Millerd passes on a friend's reframe: consider your savings a gift from your former self, who built you a war chest; he had $50,000 in savings when he quit. — 00:41:40

    “consider your savings a gift from your former self”

  • ★★ Paul Millerd suggests time-framing the experiment as a freelance year, an experimental year or a life MBA; he paid $100,000 in tuition for his MBA and master's. — 00:42:28

  • ★★ Ali treats savings as an investment from a former version of you, like raising money from a VC without giving away equity: decide how much runway you want, three months, six or a year. — 00:43:21

00:43:42 — Interlude: work doesn't have to suck; good work and bad work

  • ★★ Ali says almost none of the many people he knows on the pathless path, many of them very rich, see work as always sunshine and rainbows. — 00:44:12
  • ★★ The opening line of Paul Millerd's Good Work, "Could it be this simple? Just do things you like", struck Ali, who was asking himself in his journal every morning whether he could just do things he likes. — 00:44:40
  • ★★★ Paul Millerd says the default story in most cultures is that work must suck and be painful; he points to his own experience that it need not, and says many people in many kinds of jobs find joy in their work. — 00:45:21
  • ★★ Paul Millerd will not sell the idea, as some influencers do, that a job can be purely your passion: he does not think it possible. — 00:45:50
  • ★★★ Paul Millerd: What is possible, Paul Millerd says, is slowly moving a larger and larger part of the job-shaped container towards things you enjoy. — 00:46:18
  • ★★ Ali often tells people that everything feels like work after a while. — 00:46:18
  • ★★ Every job and every self-employed path, Ali says, mixes bad work, good-enough work and good work, in Paul Millerd's terms; once you have been at it a while, the game becomes rebalancing that portfolio. — 00:47:31
  • ★★★ Ali asks himself what he would do with his time with a hundred million in the bank, then looks at what he actually does and identifies what he does only for the money. — 00:47:31
  • ★★ Ali says starting out involves some grind, but over time small pivots leave you with a calendar of almost only things you want to be doing. — 00:48:07
  • ★★ Paul Millerd found he did not much like freelance consulting, though he was good at it and it paid well; in his first year he decided to do work he wanted to do for its own sake. — 00:48:36

00:48:37 — Step 7: follow your energy; a mode instead of a niche, Ali's academies, dropping labels

  • ★★ Paul Millerd: Before taking consulting gigs, Paul Millerd spent a month writing a long essay on the history of work, Crisis at Work, hiring an editor and an illustrator; he loved it but did not believe writing could make money. — 00:49:15
  • ★★★ From an essay by Paul Graham, Ali takes the question of what you think about in the shower as a guide to the work you would enjoy; he never once thought about medicine there, always the app or software platform he and his brother were building, or being a YouTuber. — 00:49:42 · Taimur Abdaal
  • ★★★ Paul Millerd advises finding a mode, not a niche: Ali has found a mode in which he shows up as himself while his interests change every six months, and most humans are not wired for one niche throughout adulthood. — 00:50:31
  • ★★★ Ali describes his own mode of operation: work out what he is interested in, teach about it, and see whether he can sell something based on that teaching. — 00:51:00
  • ★★★ Last year (2025) Ali told Dan he wanted to start his own online business school, the Lifestyle Business Academy, because teaching YouTube no longer energised him for 40 hours a week, while teaching people to build a business to financial freedom did. — 00:51:31 · Lifestyle Business Academy, Part-Time YouTuber Academy
  • ★★ Dan pushed back on Ali's plan with a business principle: it is much easier to do more of what works than something completely new, such as YouTube for businesses built on the Part-Time YouTuber Academy. — 00:52:01 · Part-Time YouTuber Academy
  • ★★★ Ali admits it is probably not the optimal strategy for making the most money, but his business follows whatever he is energised about at the moment. — 00:52:27
  • ★★ The Part-Time YouTuber Academy keeps running: Ali's team runs it and keeps the course and its AI tools updated, while Ali spends all his time on the Lifestyle Business Academy. — 00:53:00 · Part-Time YouTuber Academy, Lifestyle Business Academy
  • ★★ Paul Millerd attaches no story to what he does: he is not an author, creator, YouTuber or podcaster, just someone doing a set of activities he likes. — 00:53:39
  • ★★★ Ali has recently started dropping his internal label of YouTuber, which kept a subroutine running in his mind about the next video and the analytics. — 00:53:39
  • ★★ YouTube is now confined to Tuesday, Ali's filming day, the only day he thinks about YouTube videos; other slots go to the apps his team is building and the Lifestyle Business Academy. — 00:54:21 · Lifestyle Business Academy
  • ★★ Paul Millerd says many people go all in on labels such as creator, reinventing the default path off the default path; many burn out and quit, some shutting down everything even though it makes money. — 00:55:08

00:55:55 — Step 8: declare retirement from bad work; the skip test

  • ★★ Paul Millerd: For his first few years on his own Paul Millerd made an average of 30 to 40 grand a year and felt pretty bad about it. — 00:56:23
  • ★★★ Paul Millerd: Four years in, Paul Millerd ran the numbers and found that his untouched retirement funds and investments had doubled his net worth in a stock-market run, while he felt financially reckless. — 00:56:49
  • ★★ Paul Millerd: In an article written in 2021, before he made more money from his book, Paul Millerd declared himself retired. — 00:57:33

  • ★★ Paul Millerd credits Ali with the skip test: would you skip this task if you could just get to the end result? (hedged) — 00:57:33

    “Would you skip this task if you could just get to the end result?”

  • ★★★ Paul Millerd: Having spent four years mostly on things he would not skip, Paul Millerd considers himself retired from bad work, the work that drains his energy and that he resists. — 00:58:02

  • ★★ Ali likes a definition of retirement he thinks comes from Naval: no longer doing things for instrumental reasons, only because you intrinsically want to. — 00:58:02 · Naval Ravikant

00:59:00 — Step 9: handle the people around you; spouses, peers and family

  • ★ Paul Millerd: Before Paul Millerd had a child, people told him it would be different with one; now he has a child and the strategy is the same. — 00:59:08
  • ★★★ Paul Millerd: For this path, Paul Millerd advises marrying someone wired similarly who embraces uncertainty; he met his wife after blowing up his life. — 00:59:35 · Izzy Sealey
  • ★★ Paul Millerd: In the first month Paul Millerd knew his wife Angie, she was quitting her job, and they fell in love quickly. — 01:00:09
  • ★★ Paul Millerd calls having his wife alongside him a cheat code for the pathless path, because it can get lonely. — 01:00:38 · Izzy Sealey
  • ★★ Paul Millerd and his wife have lived in seven countries with their daughter over her first two and a half years. — 01:01:08 · Izzy Sealey
  • ★★ Ali sees his own old money fears in his wife Izzy, who has not had his years of wealth building: he will fly business class while she weighs up premium economy. — 01:01:08 · Izzy Sealey
  • ★★ It took Ali about three years to take a more abundant approach to money, which came from financial confidence, an inner certainty that he will be able to figure it out. (hedged) — 01:01:45
  • ★★ Paul Millerd: Chapter 4 of Paul Millerd's latest book is devoted to his wife Angie's journey to find good work, a few years behind his own. — 01:02:35
  • ★★ When Izzy lamented a sponsorship deadline, Ali, who has learned over time to keep his opinion to himself, simply agreed that it sucked. — 01:03:26 · Izzy Sealey
  • ★★ Paul Millerd says he is probably one of the poorest of his business school class, almost certainly in its bottom 1%. (hedged) — 01:03:55
  • ★★ Paul Millerd: Asked by a classmate on LinkedIn whether he feels he is not using his potential, Paul Millerd knows it is the classmate's insecurity, but still felt a little something. — 01:04:42
  • ★★★ Paul Millerd: When he wonders whether he should have taken other paths, Paul Millerd comes back to the present: without his path he might not have met his wife, lived in different countries or had so many days he didn't want to skip. — 01:05:08 · Izzy Sealey
  • ★★★ Ali suggests a thought experiment: at a reunion ten years from now you find you have earned less than your classmates in prestige jobs; how do you feel about scoring lower on the scoreboard of status and money? — 01:05:58
  • ★★ A friend of Ali's who left a hedge fund for the pathless path finds the gap with his former colleagues' wealth hard at times, but spends his days as he wants, saw his kids grow up and surfs every day. — 01:06:27
  • ★★★ Paul Millerd says almost everyone who has done something unconventional or experimental has had at least one family member say something extremely painful to them. — 01:07:35

  • ★★★ Paul Millerd tells people that leaving might suck but might also be worth it; Sasha Chapin calls this loving the moat of low status, since most people won't pay that tax. — 01:08:32

    “love the moat of low status”

  • ★ Ali loves the title of a new Chris Williamson episode: what you want is on the other side of cringe. — 01:09:06

  • ★★ Paul Millerd describes the stages of putting your work online: you fear attack, nobody pays attention, you seek attention, critics come with a readership, and you learn to deal with it and find it worth it. — 01:09:29

01:09:44 — Step 10: keep playing the infinite game; objections, regret, getting to know yourself, Ali's takeaway

  • ★★★ Paul Millerd: Against the survivorship-bias objection, Paul Millerd says people ruined by quitting are hard to find: most such decisions are reversible, and getting a job again is easier than people think. — 01:10:07
  • ★★ Paul Millerd points to Tim Ferriss's fear-setting: ask what steps you could take to get back to where you are now. — 01:10:07 · Tim Ferriss
  • ★★★ Paul Millerd cites survey data, which he has written about in his newsletters, that the regret rate for quitting a job to do something new is very low: people regret the decisions they didn't make. — 01:10:36
  • ★★ Ali cites a line from Oliver Burkeman: just because a path is unfeasible for the underprivileged does not mean it is unfeasible for you. — 01:10:36
  • ★★ Paul Millerd: Asked what would happen if everyone took the pathless path, Paul Millerd replies that most people hate the idea and are triggered by it; he writes mostly for people who are already deeply curious. — 01:11:09
  • ★★ Paul Millerd has paid for US healthcare out of pocket and never more than five to seven thousand a year: it is just a price to put in your spreadsheet with your other costs. — 01:11:57
  • ★★ Paul Millerd: Once you quit, Paul Millerd says, you have 40 extra hours of action a week in which to figure things out. — 01:12:47
  • ★★★ Paul Millerd: To anyone still feeling resistance, Paul Millerd says it comes down to getting to know yourself: he often assigns people a wander, an afternoon walk with no destination. — 01:13:13
  • ★★ Paul Millerd suggests small experiments: host an event, call someone on a path you are curious about, write something online, go to a meetup for a new interest. — 01:13:38
  • ★★ Paul Millerd: If your prime motive is not to waste time, Paul Millerd says, this path probably isn't for you: he has wasted tons of time experimenting. (hedged) — 01:14:07
  • ★★★ Ali's takeaway from Paul Millerd: you can quit your job, but it will be messy, hard and confusing, with nights you cry yourself to sleep not knowing where the money will come from. — 01:15:36
  • ★★★ What Ali misses most about a real job in medicine is its yellow brick road: the profound psychological safety of the illusion of a path you can follow for the rest of your life. — 01:16:02
  • ★★ Ali says the latest intake of junior doctors in the UK had more graduates than places, leaving some unemployed or sent to jobs far from home, such as Aberdeen. — 01:16:02
  • ★★ Ali argues that the corporate world of guaranteed jobs is becoming much less secure and safe than it once was. — 01:17:03

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Mentioned

Central: default path · financial confidence · Good Work · Lifestyle Business Academy · Paul Millerd · The Pathless Path

Also: People: Ben Hunt · Chris Williamson · Derek Sivers · Dickie Bush · Izzy Sealey · Naval Ravikant · Oliver Burkeman · Paul Graham · Sasha Chapin · Taimur Abdaal · Tim Ferriss

Projects: 1K Challenge · Part-Time YouTuber Academy

Organizations: Boston Consulting Group · GE · Massachusetts Institute of Technology · McKinsey

Concepts: experimental mindset · fear-setting · infinite game · passive income · reversible and irreversible decisions · runway · skip test · winning the work

Places: Aberdeen · Hong Kong

Also centred on default path: This book made me quit my job

Also centred on Good Work: 19 Books to Transform Your 2026

Also centred on Paul Millerd: This book made me quit my job

Also centred on The Pathless Path: 15 Incredible Books to Read in 2026 · How to figure out what to do with your life #shorts · This book made me quit my job · If you’re overwhelmed, read this

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