Paul Millerd01 December 2022

The Pathless Path: How To Recreate Your Life And Career In 2023 - Paul Millerd

5Frameworks

12Insights

Episode overview

Ali Abdaal talks with Paul Millerd about leaving prestigious default careers and developing a more personal relationship with work. They examine how sabbaticals, small experiments, and attention to energy can reveal what someone values before they accept the financial and social costs of an uncertain path. Paul also explains how years of writing and hundreds of conversations led him to write The Pathless Path, while both discuss defining “enough” and pursuing meaningful work over longer horizons.

Key ideas

The default path offers legibility and security, but it can obscure whether work is actually aligned with a person's values.
A one-to-three-month break from “worker mode” can create enough space to notice neglected interests, hidden benefits of employment, and genuine priorities.
Use small, deliberately limited experiments—Paul's “ship, quit, and learn” approach—to test possible careers and lifestyles without demanding a permanent commitment.
Pay attention to activities that generate energy and curiosity; premature focus on monetization can interrupt the exploration needed to find sustainable creative work.
An uncertain path carries financial and social costs, including variable income, identity loss, and less encouragement from close relationships.
Pairing uncertainty with wonder makes experimentation more tolerable by keeping possible upside and discovery visible alongside risk.
Define what “enough” means explicitly, because otherwise the default objective for careers and businesses becomes perpetual growth.
Long-term ambition can emphasize meaningful output over years rather than maximizing money, scale, or publishing frequency in the short term.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Finance4 steps

Defining Your Enough

Write an explicit definition of enough so 'more' stops running your life by default

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Peak Performance5 steps

Follow Energy, Not Money

Optimise for what energises you to find effortless, sustainable output over the long game

Read →

Productivity5 steps

Ship, Quit, Learn

Run tiny time-boxed experiments designed to quit to discover what energises you

Read →

Mindset5 steps

The Default Path vs The Pathless Path

Trade the inherited career script for work designed around meaning and energy

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Self-Mastery3 steps

The Value-Cost-Trade Decision

Decide any life change by pricing what you value against what it costs

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People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 21

Paul MillerdCoinedended up breaking into strategy Consulting for like nine years loved my time working in that industry
“Paul has written a fantastic book called the pathless puff”
▶ Watch at ~0:00approx.
Ali AbdaalMentionsthe ongoing podcast where every week I get the chance to sit down with inspiring authors, entrepreneurs, creators, and other inspiring people.
“Paul welcome welcome to the show thank you so much for coming on how are you doing”
▶ Watch at ~1:30approx.
Dan Murray-SerterCoinedthe founder Dan who we actually had on season one of the Deep dive podcast
“Dan marisota who is the founder of heights”
▶ Watch at ~11:30approx.
Tara SwartMentionsneuroscientist and psychiatrist Dr Tara swart who's the chief science officer of heights
“Dr Tara swart who is a neuroscientist and psychiatrist”
▶ Watch at ~11:30approx.
Lewis HowesMentionsa podcast called School of greatness by lisis hose
“it took Lewis hose on School of greatness podcaster prod me”
▶ Watch at ~17:00approx.
Tiago ForteCoineda new book by Thiago Forte
“building a second brain a new book by Thiago Forte”
▶ Watch at ~28:00approx.
Rebecca SolnitUsesmentioned
“this is when I start reading like people like David White and Rebecca solnit”
▶ Watch at ~32:30approx.
David WhyteUsesmentioned
“this is when I start reading like people like David White and Rebecca solnit”
▶ Watch at ~32:30approx.
Paul JarvisMentionsmentioned
“you linked me to this article uh by Paul Jarvis about finding your enough point”
▶ Watch at ~37:30approx.
Thomas FrankMentionsmentioned
“other teachers including people that I know people I'm friends with like Thomas Frank and Nathaniel Drew”
▶ Watch at ~44:00approx.
Nathaniel DrewMentionsmentioned
“other teachers including people that I know people I'm friends with like Thomas Frank and Nathaniel Drew”
▶ Watch at ~44:00approx.
Tim FerrissCoinedramit sethi or tim ferriss guy kawasaki a lot of these guys i just helped promote them and connect with them really early on
“Cal Newport chatting to Tim Ferriss on Tim ferriss's podcast”
▶ Watch at ~49:00approx.
Cal NewportMentionskind of like C newort around you know technology and addiction
“I was listening to a good um uh Cal Newport chatting to Tim Ferriss on Tim ferriss's podcast”
▶ Watch at ~49:00approx.
Ram DassCoinedmentioned
“ramdas talks about this idea of like the this space suit”
▶ Watch at ~59:30approx.
Noah KaganMentionshe started out as employee number 30 at facebook before getting fired by mark zuckerberg
“I was re-listing to an an interview I did with Noah Kagan”
▶ Watch at ~1:02:30approx.
Mitch AlbomCoinedthe writer Mitch album is at the peak of his work career
“the writer Mitch album is at the peak of his work career”
▶ Watch at ~1:08:00approx.
Morrie SchwartzMentionshe's in his late 70s he's dying of Lou Gehrig's Disease
“it talks about this guy Mori who's Fully Alive and engaged with life at the end of his life”
▶ Watch at ~1:08:30approx.
Seth GodinMentionshe's still connected energized like seems Fully Alive with like what he's doing
“I look up to people like Seth Godin”
▶ Watch at ~1:08:30approx.
Jim O'ShaughnessyMentionswho's like still injecting this playful curiosity
“I really admire people like Jim O'Shaughnessy who's like still injecting this playful curiosity”
▶ Watch at ~1:09:00approx.
Tiago ForteMentionsa new book by Thiago Forte
“Thiago Forte was running a boot camp with Billy Bros”
▶ Watch at ~1:20:30approx.
Billy BroasMentionsmentioned
“Thiago Forte was running a boot camp with Billy Bros”
▶ Watch at ~1:20:30approx.

Resources · 31

The Pathless PathRecommendsbook · Paul Millerd
“I give copies to anyone who is struggling to figure out what they want to do with their lives”
▶ Watch at ~0:00approx.
HeightsUsesproduct · Heights
“Heights is a brain care smart supplement that I've actually been taking for the last 12 months”
▶ Watch at ~11:30approx.
HeightsRecommendsproduct · Heights
“if you use the coupon code Ali 15 that's ali15 at checkout then you'll get 15 off”
▶ Watch at ~12:00approx.
The School of GreatnessMentionspodcast · Lewis Howes
“it took Lewis hose on School of greatness podcaster prod me”
▶ Watch at ~17:00approx.
SolidityMentionssoftware
“I'll program in web3 solidity or whatever the thing is”
▶ Watch at ~18:30approx.
The Pathless PathCoinedbook · Paul Millerd
“I wrote about this in my book”
▶ Watch at ~19:00approx.
eBayUseswebsite
“earning money on random things online selling things on eBay”
▶ Watch at ~19:00approx.
InstagramUsessoftware · Meta Platforms
“I scroll Instagram and occasionally I'll post a photo on Instagram”
▶ Watch at ~20:30approx.
NetflixUsescompany
“I go home and I watch Netflix and I scroll Instagram”
▶ Watch at ~20:30approx.
BostonMentionsplace
“I just sort of woke it up woke up I wandered around Boston I was like writing I launched my podcasts”
▶ Watch at ~23:00approx.
Building a Second BrainMentionsbook · Tiago Forte
“short form have recently released a summary of building a second brain a new book by Thiago Forte”
▶ Watch at ~28:00approx.
ShortformRecommendswebsite · Shortform
“head over to shortform.com forward slash Deep dive”
▶ Watch at ~28:00approx.
ShortformUseswebsite · Shortform
“the thing that I personally subscribe to”
▶ Watch at ~28:30approx.
YouTubeMentionswebsite · Google
“my YouTube channel is kind of going well or maybe it's not”
▶ Watch at ~34:00approx.
TwitterUseswebsite
“it's always nice when you post what you're thinking on Twitter”
▶ Watch at ~38:00approx.
KindleUsesproduct · Amazon
“bringing up my Kindle highlights from the book as well”
▶ Watch at ~40:30approx.
YouTube for BeginnersRecommendscourse · Ali Abdaal
“if you've ever thought about starting a YouTube channel this is the class for you”
▶ Watch at ~43:30approx.
SkillshareUseswebsite
“I have actually been teaching on skillshare since 2019”
▶ Watch at ~43:30approx.
SkillshareRecommendswebsite
“you can access all of them completely free of charge by going to skillshare.com forward slash Deep dive”
▶ Watch at ~43:30approx.
YouTube for BeginnersCoinedcourse · Ali Abdaal
“one class you might be interested in is my YouTube for beginners class”
▶ Watch at ~43:30approx.
YouTubeUseswebsite · Google
“the stuff I've done has almost never felt like uh chore”
▶ Watch at ~47:00approx.
The Tim Ferriss ShowMentionspodcast · Tim Ferriss
“Cal Newport chatting to Tim Ferriss on Tim ferriss's podcast”
▶ Watch at ~49:00approx.
Part-Time Creator AcademyCoinedcourse · Ali Abdaal
“we should totally start a whole new YouTube channel the part-time Creator Academy teaching people how to be creators”
▶ Watch at ~56:00approx.
WalesMentionsplace
“right now I'm in Wales we're on this four day team Retreat”
▶ Watch at ~57:30approx.
BaliMentionsplace
“then I found myself in Bali this is the first year of self-employment”
▶ Watch at ~1:01:00approx.
Tuesdays with MorrieRecommendsbook · Mitch Albom
“a book that has really stuck with me is two sides with Mori”
▶ Watch at ~1:07:30approx.
New York CityMentionsplace
“I was living in New York spending like five thousand dollars a month”
▶ Watch at ~1:13:30approx.
TwitterUseswebsite
“sharing on Twitter a little more like writing a little more publicly”
▶ Watch at ~1:17:00approx.
TaiwanMentionsplace
“I'm in Taiwan for the year my cost of living is lower”
▶ Watch at ~1:21:00approx.
Think BoundlessCoinedwebsite · Paul Millerd
“or website think-boundless.com”
▶ Watch at ~1:31:00approx.
BoundlessCoinednewsletter · Paul Millerd
“my newsletter boundless.substack.com”
▶ Watch at ~1:31:00approx.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster58:30

Test the underlying thing, not the identity you imagine

People get into trouble trying to 'be something' rather than be themselves. Ali's dream of 'the digital nomad lifestyle' was really just the question 'would it be cool to work somewhere other than home?'. Millerd invokes Ram Dass's spacesuit metaphor: you perform roles but you aren't the spacesuit. Strip the script down to the real thing you're testing.

People test a whole identity instead of a simple underlying question.
'Digital nomad' really means 'work from a different location'.
Ram Dass's spacesuit: you play roles but aren't the role.
Reducing a dream to its core question makes it testable.

“you're starting with a script of like what a digital Nomad should be when what you're really trying to test is like would it be…”
Paul Millerd · 59:00

#identity#digital nomad#experiments

Hot Take· 2

Hot Take09:30

Who should NOT quit their job to go independent

Millerd's contrarian take: if financial security is your primary concern, freedom probably isn't, and that's a red flag against going solo. The people who thrive crave autonomy and come asking 'give me five tips to do this better', not 'should I quit?'. He warns against the meme of quitting to become a creator purely for money and status.

Fixating on money and mortgage is a red flag you're not built for the freedom path.
Thrivers value autonomy over predictable income.
They ask how to do it better, not whether to do it at all.
Quitting for money and status alone rarely sustains people.

“if like Financial Security is your primary concern like probably doing your own thing and having freedom is also not your primary concern”
Paul Millerd · 13:00

#quitting#freedom#self-employment

Hot Take1:27:00

Don't find a niche, find a mode of being

Millerd reframes the advice: don't find a niche, find a mode of being in which you can show up and do work you don't resent. Doing your own thing lets you lower the percentage of activities you resent, leaving more space for creativity and curiosity. Once you've found that mode, ambition is simply how fast you want to go and how much leverage to apply.

Seek a sustainable mode of being over a marketable niche.
Independence lets you cut the share of work you resent.
More space preserves creativity and curiosity.
Ambition becomes a question of speed and leverage, not direction.

“don't find a niche like find a mode of being in which you can show up”
Paul Millerd · 1:27:30

#career design#ambition#meaning

Explainer· 3

Explainer06:30

Why the old formulas for career success stopped working

Millerd explains that as work became abstracted (we no longer use our hands or connect to what we make), people grew less satisfied. In 2020 the whole world started asking deep questions about work and his readership exploded. The old script of getting a job, working up the company and getting the company car no longer reliably delivers fulfilment.

Abstracted, hands-off work leaves people less satisfied.
2020 triggered a mass re-examination of the meaning of work.
The 'get a job and climb' formula increasingly fails to deliver fulfilment.
Human needs to matter, be useful and feel connected go unmet.

“in 2020 the whole world sort of like showed up like asking these deep questions about work and my readership just like exploded”
Paul Millerd · 01:00

#work#meaning#great reckoning

Explainer32:00

Uncertain discomfort plus wonder equals courage

Millerd shares the equation from his book: uncertain discomfort alone is terrifying, but pair it with wonder ('ooh, what might also happen?') and you can immunise yourself against the fear for a stretch of time. He leaned on poets and writers like David Whyte and Rebecca Solnit for the courage to follow an uncertain path with deep humility.

Uncertain discomfort by itself is scary.
Adding wonder flips the experience into something bearable.
Poetry and literature supply courage when you have no plan.
Hold a direction while admitting you may be wrong: deepest humility.

“uncertain discomfort is terrifying... but if you pair it with Wonder like ooh what might also happen then you can sort of immunize yourself for…”
Paul Millerd · 32:30

#uncertainty#wonder#courage

Explainer11:00

The hidden cost of an unconventional path: less support, so find the others

Beyond money, Millerd warns the heaviest cost is others' judgment. On an uncertain path you crave affirmation more, yet receive less active encouragement, which feels like a lack of support. His antidote is to share your journey publicly to 'find the others', people who just get it, so you can coexist in shared uncertainty without having to justify yourself.

The social cost often outweighs the financial one.
You crave affirmation more precisely when others offer it less.
Writing in public helps you find like-minded people.
Being around people who understand you keeps you in the game.

“do not be surprised if you take an unconventional path that you will receive less support than you expect”
Paul Millerd · 10:30

#community#social cost#encouragement

Story· 3

Story17:30

Confronting the worst-case scenario that set Ali free

Ali describes how Lewis Howes and Paul's standing offer of a place to stay forced him to face his real fear: ending up broke, homeless and unloved. Once he saw that scenario was neither feasible nor unrecoverable, thanks to his skills and support network, he felt fully at peace leaving medicine, confident he'd never go back even in the worst case.

The real fear was being broke, homeless and alone forever.
A friend's offer of shelter exposed the fear's absurdity.
Skills and a support network make the worst case recoverable.
Facing it head-on delivered the final peace to commit.

“even if in the worst case scenario I lost everything I probably still wouldn't go back to Medicine and it was that that click in…”
Ali Abdaal · 18:30

#fear#risk#leaving medicine

Story1:16:00

The 'playing accountant' trap that short-circuits creativity

After quitting, Millerd slashed spending painlessly (cooking at home, dropping restaurants) and discovered he didn't miss things he thought made him happy. But he over-corrected into a minimised-spend mode, toiling over a $40 vs $100 webcam and 'playing accountant' instead of living. He now deliberately invests in himself, buying good equipment and committing fully rather than penny-pinching his ambition.

Cutting spending often costs little happiness.
The perceived money cost is bigger than the real one.
Over-minimising spend can short-circuit creativity and ambition.
After finding your footing, invest boldly in yourself.

“I was playing accountant rather than like living my life”
Paul Millerd · 1:17:00

#money#spending#investing in yourself

Story1:19:00

How Paul wrote The Pathless Path from 383 conversations

Millerd's book emerged from writing since he quit and from 383 free 'curiosity conversations' about people's relationship with work. He kept hearing hidden knowledge people felt they couldn't share publicly. Choosing to write over doubling down on a lucrative course, he spent 13 months on it; the emotional introduction only came during a tearful motorcycle ride, when he connected it all to his parents giving him the freedom to dream.

The book grew from consistent writing plus 383 curiosity conversations.
People shared 'hidden knowledge' they felt unable to say publicly.
He chose writing over a more lucrative course path.
The core insight surfaced emotionally, connecting to his parents' sacrifice.

“what I'm writing about is like this hidden knowledge that nobody feels they can talk about publicly”
Paul Millerd · 1:20:00

#writing#book#creative process

Takeaway· 3

Takeaway13:30

Take a 1-3 month break from 'worker mode' instead of quitting

Millerd doesn't think most people should quit; instead they should aim for a one-to-three-month break from 'worker mode', the hyper-scheduled state of constantly moving toward things for others. That space lets you ask what you're doing with your life, what you actually value, and whether your job has hidden benefits you couldn't see before.

Worker mode is being hyper-scheduled and always in motion for others.
A 1-3 month break reveals what you value and fear.
The break may show your job has hidden upsides worth keeping.
Most people should aspire to space, not necessarily quitting.

“what I think most people should aspire to get in their life is like a one to three month break from worker mode”
Paul Millerd · 14:00

#sabbatical#reflection#worker mode

Takeaway37:00

Break big existential fears into small daily ones

An uncertain path forces constant grappling with questions no one asks on a conventional track. Millerd learned to take massive ambiguous fears (of death, of not belonging, of going broke) and break them into many small daily existential crises he can greet mindfully: 'I see you, money insecurity, been here before.' The fear never fully disappears but becomes manageable.

Conventional paths never make you ask why you're doing them.
Uncertainty forces daily confrontation with fear.
Big fears become manageable when broken into small daily ones.
Naming a recurring fear mindfully takes away its grip.

“you sort of are able to take these massive ambiguous fear of death fear of being loved fear of not belonging and break it down…”
Paul Millerd · 37:00

#fear#mindfulness#uncertainty

Takeaway1:08:00

Choose role models for who's fully alive at the end, not the retirement number

Millerd thinks about role models by how they show up late in life. He admires Morrie (from Tuesdays with Morrie), Seth Godin and Jim O'Shaughnessy for staying energised, connected and playfully curious with age. What made it easy to walk away from consulting was realising he wasn't on a path toward that state, but toward the cynical, disconnected men around him.

Judge role models by how alive they are late in life.
Millerd admires Morrie, Seth Godin and Jim O'Shaughnessy.
A target retirement number isn't the route to that vitality.
He left consulting partly to avoid becoming the disillusioned men around him.

“I wasn't on a path to get there I was on a path to show up like a lot of the men I was surrounded…”
Paul Millerd · 1:09:30

#role models#aging#vitality

Key ideas

Frameworks in this episode

Defining Your Enough

Follow Energy, Not Money

Ship, Quit, Learn

The Default Path vs The Pathless Path

The Value-Cost-Trade Decision

People & resources mentioned

People · 21

Resources · 31

Insights & moments

⚡Myth Buster· 1

Test the underlying thing, not the identity you imagine

◆Hot Take· 2

Who should NOT quit their job to go independent

Don't find a niche, find a mode of being

✶Explainer· 3

Why the old formulas for career success stopped working

Uncertain discomfort plus wonder equals courage

The hidden cost of an unconventional path: less support, so find the others

❝Story· 3

Confronting the worst-case scenario that set Ali free

The 'playing accountant' trap that short-circuits creativity

How Paul wrote The Pathless Path from 383 conversations

▲Takeaway· 3

Take a 1-3 month break from 'worker mode' instead of quitting

Break big existential fears into small daily ones

Choose role models for who's fully alive at the end, not the retirement number

Myth Buster· 1

Hot Take· 2

Explainer· 3

Story· 3

Takeaway· 3