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Paul Millerd (The Pathless Path)19 November 2023

Redefining success, money, and belonging

8Frameworks
15Insights

Episode overview

Paul Millerd explains the “pathless path” as a conscious move away from inherited scripts about continuous employment, status, and certainty. He and Lenny Rachitsky discuss sabbaticals, small experiments, energy tracking, financial runway, contracting, and conversations with people already following unconventional paths. Millerd argues that uncertainty and recurring fears may remain, but deliberate exploration can produce more satisfying work and fewer regrets.

Key ideas

  • The default path is the largely unexamined cultural script governing work, education, income, family, and adulthood.
  • The pathless path embraces uncertainty, experimentation, abundance, and continual reinvention instead of treating an unclear future as a problem.
  • A three-month sabbatical—or even three protected hours during a workday—can create enough distance to reconsider one's relationship with work.
  • Track which activities create or drain energy, then increase the energizing work while avoiding the creation of another unwanted job.
  • Reduce transition risk through savings, lower living costs, contract work, geographic flexibility, grants, loans, or a predefined exploration budget.
  • Use fear-setting to compare the risks of action with the costs of inaction; existential fears may need to be accepted rather than eliminated.
  • “Ship, quit, and learn” means launching bounded experiments, permitting yourself to stop, and using the result to choose the next step.
  • Success is framed as coming alive and finding work worth continuing, rather than maximizing prestige, achievement, or a single financial metric.

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

Frameworks in this episode

Mindset5 steps

Dancing With Your Fears

Price the cost of inaction, then stop trying to kill the fears that won't die — have a conversation with them.

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Strategy5 steps

Engineering Financial Space

Convert your job into a contract, cut the burn, and buy back time without a clean break.

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Entrepreneurship4 steps

Ship, Quit, and Learn

Design the smallest thing you can ship that is built to be quit — then let shipping it tell you what's next.

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Mindset4 steps

The 3-of-500 Months Sabbatical

Frame a sabbatical as 3 months out of a ~500-month working life, and budget 6-8 weeks just to unwind.

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Peak Performance4 steps

The Energy Audit

After every activity, log energised or drained — then do more of one and less of the other.

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Finance5 steps

The Life MBA Reframe

Set a runway budget, name it an investment in yourself, and give people a socially legible story for it.

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Influence5 steps

The Path Expert Conversation

Find someone a few years ahead on the path you're curious about, and offer them written questions.

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Self-Mastery4 steps

The Three-Hour Work Mindfulness Experiment

Steal three hours from a workday, do something purposeless, and study the guilt that shows up.

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People & resources mentioned

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

People · 7

  • Paul MillerdMentionsPaul is the author of The Pathless Path and describes his transition from consulting to independent writing, podcasting, courses, and community-building.

    “today my guest guest is Paul Millard Paul is the author of The pathless Path imagining a new story for work and life”

    ▶ Watch at ~1:00approx.
  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    “Paul thank you so much for being here welcome to the podcast”

    ▶ Watch at ~4:30approx.
  • David AutorMentionsIdentified as an MIT economist whose research addresses the decline of comfortable middle-class jobs.

    “they're shrinking davidor a economist from MIT has pretty good research on this”

    ▶ Watch at ~9:30approx.
  • Tim FerrissCoinedCited for his fear-setting framework and as an influence on Paul Millerd's five-episode podcast experiment.

    “a big source of inspiration around this is Tim Ferris is fear setting”

    ▶ Watch at ~40:30approx.
  • Tim FerrissMentionsCited for his fear-setting framework and as an influence on Paul Millerd's five-episode podcast experiment.

    “I stole this from Tim Ferris as well I'm going to do five episodes”

    ▶ Watch at ~46:00approx.
  • David DemingMentionsHis work is cited regarding growth in alternative work arrangements.

    “if you search David deming's work on this it's pretty compelling”

    ▶ Watch at ~52:00approx.
  • Luke BurgisCoinedNamed as the author of Wanting and described as having followed the startup path.

    “a second book I'd recommend I actually really like Luke burgess's book wanting”

    ▶ Watch at ~56:00approx.

Resources · 21

  • The Pathless Path: Imagining a New Story for Work and LifeCoinedbook · Paul Millerd

    “Paul is the author of The pathless Path imagining a new story for work and life”

    ▶ Watch at ~1:00approx.
  • SanityRecommendssoftware · Sanity

    “head over to sanity.io Lenny to get started for free”

    ▶ Watch at ~3:00approx.
  • Tim Ferriss ShowMentionspodcast · Tim Ferriss

    “after hearing their ad on the Tim Ferris podcast”

    ▶ Watch at ~3:30approx.
  • Maui Nui VenisonUsescompany

    “my wife and I made stew and steaks and all kinds of grilled goodies with the meat”

    ▶ Watch at ~4:00approx.
  • AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk

    “you were at Airbnb Airbnb every two years you were there was a different company”

    ▶ Watch at ~8:30approx.
  • PenguinMentionscompany

    “this is why it was very easy for me to say no to penguin”

    ▶ Watch at ~15:30approx.
  • IntelMentionscompany

    “I know Intel I have friends that have done the sabatical Intel you get like six weeks after seven years”

    ▶ Watch at ~23:00approx.
  • GPTsUsessoftware · OpenAI

    “I was playing with that today I'm like oh my gosh”

    ▶ Watch at ~25:30approx.
  • Wix StudioMentionssoftware · Wix

    “this episode is brought to you by Wix Studio”

    ▶ Watch at ~26:00approx.
  • Stanford Business SchoolMentionscompany

    “if somebody says I'm going to Stanford Business School generally you'll receive positive praise”

    ▶ Watch at ~31:30approx.
  • MediumUseswebsite · Medium

    “writing an article and posting it on medium in LinkedIn”

    ▶ Watch at ~37:00approx.
  • LinkedInUseswebsite · LinkedIn

    “writing an article and posting it on medium in LinkedIn”

    ▶ Watch at ~37:00approx.
  • Fear-settingCoinedother · Tim Ferriss

    “a big source of inspiration around this is Tim Ferris is fear setting”

    ▶ Watch at ~40:30approx.
  • StrategyUCoinedcourse · Paul Millerd

    “I started this business strategy U early on in my path because I wanted to productize my Consulting”

    ▶ Watch at ~48:30approx.
  • The Pathless Path: Imagining a New Story for Work and LifeRecommendsbook · Paul Millerd

    “oh read my book”

    ▶ Watch at ~54:00approx.
  • The Great Work of Your LifeRecommendsbook

    “one is called the great work of your life”

    ▶ Watch at ~55:30approx.
  • WantingRecommendsbook · Luke Burgis

    “a second book I'd recommend I actually really like Luke burgess's book wanting”

    ▶ Watch at ~56:00approx.
  • ChatGPTUsessoftware · OpenAI

    “chat GPT I just created my own GPT to do podcast show notes automatically for me today”

    ▶ Watch at ~58:30approx.
  • The New York TimesMentionscompany · The New York Times Company

    “I'm against like the New York Times says there's too many podcasts”

    ▶ Watch at ~1:01:00approx.
  • PathlessPath.comUseswebsite · Paul Millerd

    “I've been compiling a lot of my more recent stuff under pathless path.com”

    ▶ Watch at ~1:03:00approx.
  • LennyPodcast.comMentionswebsite · Lenny Rachitsky

    “you can find all past episodes or learn more about the show at Lenny podcast.com”

    ▶ Watch at ~1:04:30approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

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

Hot Take· 5

Hot Take08:30

Everyone Is Already on a Pathless Path

Paul's contrarian claim is that the smooth upward corporate trajectory is an illusion. Even at one company, every two years you're effectively at a different company. Constant disruption, relationship and health challenges, and external shocks mean everyone is already reinventing and reevaluating, whether they admit it or not.

  • The idea of life as a smooth upward corporate ascent limits your possibilities
  • At a fast company, every two years is effectively a different company
  • Personal shocks (relationships, health, inflation) constantly change your reality
  • Comfortable, abundant middle-class jobs are shrinking, per MIT economist David Autor

“my hot take is that we're all on a pathless path”

Paul Millerd · 08:30
#career#hot-take#pathless-path#economy
Hot Take31:30

Your Unconventional Path Is a Better MBA Than Business School

Paul points out the double standard: say you're going to Stanford Business School and people praise you, even though you're really not working for two years and spending $150k–$200k. His first three years off broke even financially, yet people judged and insulted his path while celebrating business school. His reframe: treat the money as tuition you're paying into your own life.

  • Business school earns praise but means two years of no salary plus $150k-$200k
  • Paul's first three years off actually broke even financially
  • People still judged and insulted his path while celebrating the MBA route
  • Reframe the spend as investing in your own life

“if somebody says I'm going to Stanford Business School generally you'll receive positive praise oh that's awesome but what they're really doing is not working…”

Paul Millerd · 31:30
#money#hot-take#education#reframe
Hot Take39:30

You Need a "Boomer-Compatible" Story for What You're Doing

To defuse the insecurities your unconventional path triggers in others, Paul recommends a friendly cover story. Say you're just 'tinkering' — something about the word makes people find it delightful rather than threatening. For skeptical parents, give a 'boomer-compatible' label like entrepreneur or business owner that instantly resonates.

  • Your path triggers insecurities because you're doing what others weren't allowed to
  • Saying you're 'tinkering' makes the work sound delightful, not threatening
  • Parents may need a 'boomer-compatible' story to feel comfortable
  • Labels like 'entrepreneur' or 'business owner' instantly resonate

“just tell people you're tinkering when they ask you how what are you working on I'm just tinkering”

Paul Millerd · 39:30

“you need a boomer compatible story for what you're up to”

Paul Millerd · 40:00
#identity#communication#hot-take
Hot Take59:00

"Coming Alive Over Getting Ahead"

Paul's life motto is 'coming alive over getting ahead.' He's default-skeptical of chasing achievement and uses the phrase to remind himself that intrinsic energy beats extrinsic outcomes. He repeated it to himself right before rejecting a book deal, after the publishers talked down to him and told him he probably wouldn't succeed.

  • His motto is 'coming alive over getting ahead'
  • He's default-skeptical of chasing achievement and prestige
  • Extrinsic outcomes won't do much for him beyond enough money
  • He repeated the mantra before rejecting a book deal from publishers who talked down to him

“one coming alive over getting ahead that's something I keep coming back to”

Paul Millerd · 59:00
#philosophy#motto#hot-take
Hot Take1:00:30

Don't Start a Podcast to Make Money

Paul's advice for aspiring podcasters: if your goal is money, don't. Even with an audience it's rarely the best route, and podcasting is the ultimate long game that requires intrinsic love of the conversations. Still, he pushes back on 'there are too many podcasts' — outside the tech bubble almost nobody has one, and the medium is a free, permissionless creative gift.

  • If you want a podcast to make money, it's probably not worth getting into
  • Podcasting is the ultimate long game; you need intrinsic love of the format
  • Contrary to the NYT, Paul thinks there aren't too many podcasts
  • Podcasts and newsletters are free, permissionless creative innovations

“if you want a podcast to make money it's probably not something you should get into”

Paul Millerd · 1:00:30

“podcast is the ultimate long game”

Paul Millerd · 1:00:30
#podcasting#creativity#hot-take

Explainer· 1

Explainer05:00

What the "Default Path" Actually Is

Paul Millerd defines the default path as the culturally-inherited script for how a life should go, most powerful in your late teens and 20s. In the US it's college, good grades, good job, house, marriage, family, and continuous work for all of adulthood. Opting out is hard because the path lives in other people's heads too, so simply existing outside it triggers their insecurities.

  • The default path is a story in your head about what you should do, and it differs by culture
  • US version: college, good grades, good job, buy a house, get married, have a family
  • For work specifically it means get a job and work continuously for all of adulthood
  • Living outside the frame triggers insecurities in other people

“it's really the story in your head about what you should do and most of us have some sort of script that we're living out”

Paul Millerd · 05:00

“you'll (06:00) trigger insecurities in other people by just existing outside the frame of the default path”

Paul Millerd · 05:30
#career#work#default-path#culture

Story· 2

Story14:00

The Aha: You Can Design Your Life Around Liking Work

When Paul left his job he wanted to escape work entirely, and lowered his cost of living in Asia to about $1,000/month to do it. But he fell into writing and creating for their own sake and realized his hidden lifelong assumption — that work sucks and must be tolerated — was wrong. The breakthrough was discovering you can design a life around work you actually enjoy.

  • He initially wanted 'escape work' and to not work at all
  • He lowered his cost of living in Asia to about $1,000 per month
  • The hidden assumption for his first 32-33 years: work sucks and must be tolerated
  • The aha was that you can design around liking work

“the big aha for me was oh you can design around liking work”

Paul Millerd · 14:30

“the hidden assumption I had around work for the first 32 33 years of my life was work sucks you have to figure out how…”

Paul Millerd · 15:00
#work#meaning#story
Story27:30

The Real Income Arc: 50k, 30k, 24k, Then More Than Ever

Paul is candid that the pathless path meant a real income dip. He made $50k his first freelancing year, then about $30k, $24k, and $30k, not matching his old salary until year five. He optimized those early years for exploration and self-knowledge while dramatically lowering his cost of living. This year he'll make more than ever — and every day of it has been delightful.

  • First year freelancing: $50k, then roughly $30k, $24k, $30k
  • He didn't come close to his old salary until his fifth year
  • Early years were optimized for exploration and getting to know himself
  • This year he'll make more than he ever has, with abundant time for family

“it was not until my fifth year that I came close to the salary I left”

Paul Millerd · 27:30

“I made 50 Grand the first year because I was freelancing then I made like 30 Grand 24 Grand and then 30 grand”

Paul Millerd · 28:00
#money#freelancing#story

Tool· 1

Tool29:30

Turn Your Job Into a Contract to Buy Freedom

A concrete tactic Paul has seen work: convert your full-time role into a contract engagement. Employers are more open to it than people expect, and once you're a contractor they can't dictate where you work. The tradeoff is more risk — a contractor can be fired in a day — but for someone already known inside the company it can be a stable way to create space.

  • Ask to become a contractor, e.g. three days a week on defined work
  • Employers are more open to this than people assume
  • As a contractor they can't control where you physically work
  • The tradeoff: a contractor is easy to fire, so there's more risk

“a big move that a lot lot of people do is turn their current job into a contract job”

Paul Millerd · 29:30

“a contractor is very easy to fire you can fire a contractor in a day”

Paul Millerd · 30:00
#freelancing#tactics#work#money

Takeaway· 6

Takeaway07:00

When You Quit, Fire the Manager in Your Head

Paul argues most people who leave jobs keep enforcing an invisible contract: Monday to Friday, 8–10 hours, work required. They forget they're now allowed to take an afternoon off with their kids. The real question isn't whether you stay on the default path, but whether you're consciously opting into its costs and tradeoffs rather than just accepting them.

  • Quitters often keep obeying an internal manager they never fired
  • They don't realize they can take an afternoon off to spend with their kids
  • The implicit contract of a fixed 8-10 hour workweek may not actually serve you
  • The point is being conscious of the costs and tradeoffs, not rejecting the path

“a lot of times when people quit their jobs they forget to fire the manager in their head right they don't realize they can take…”

Paul Millerd · 07:00
#work#autonomy#mindset
Takeaway16:30

Three Months Out of a 500-Month Working Life

Paul reframes the sabbatical as trivially affordable in time terms: if you assume continuous adult work, that's roughly 500 months, so carving out three to reconnect with yourself is tiny. People routinely pull off much harder things, like saving for a dream home, when it's a genuine priority. For him, creating this space mattered more than owning a house or getting married.

  • A working adult life is about 500 months
  • Finding just three of those months to explore is highly attainable
  • People accomplish harder goals like saving for a home when it's a true priority
  • Creating this space was more important to Paul than a house or marriage

“if you're assuming you're going to work continuously in adulthood that's about 500 months try to find three months of that where you can create…”

Paul Millerd · 16:30
#sabbatical#priorities#career
Takeaway18:30

Can't Take a Sabbatical? Take an Afternoon

For people who insist a sabbatical is impossible, Paul offers a low-cost version: block off three hours during a workday, sneak out, and go for a walk with no destination or do something from childhood like play an instrument or paint. Then practice a kind of 'work mindfulness' — notice what emerges, and interrogate any guilt about sneaking out for what it reveals about your definition of work.

  • Block off three hours during a workday and sneak out
  • Go for a walk without a destination, or revisit a childhood activity
  • Pay attention to what emerges — a form of work mindfulness
  • Interrogate the guilt: where does the bad feeling about sneaking out come from?

“take an afternoon take 3 hours during a workday day has to be during a work day block”

Paul Millerd · 18:30

“go for a walk without a destination or do something from your childhood that you used to do all the time”

Paul Millerd · 19:00
#exploration#mindfulness#work
Takeaway30:30

Set a Runway Budget and Give Yourself Permission to Burn It

Lenny shares the trick that made time off feel safe: pre-decide a runway budget for the exploration period, then consciously commit to burning through it as a bet that it'll lead to something interesting. Naming that money as an investment in your life — Paul calls it a kind of self-directed MBA — let both Lenny and his wife accept the likely loss in exchange for the upside.

  • Decide up front how much runway the exploration period will cost
  • Commit to burning through it as a bet it leads to something great
  • Naming the money as an investment makes the loss psychologically acceptable
  • Six months of runway became a full year as the search continued

“I set a budget of here's the runway that I'm G to give myself”

Lenny Rachitsky · 30:30

“I'm just going to burn through this money just with the bet that it'll lead to something interesting”

Lenny Rachitsky · 31:00
#money#risk#planning
Takeaway37:30

Audit What Energizes You vs. What Drains You

The single most effective piece of advice in both their journeys: after every activity, notice whether it energized or drained you, then do more of the former and less of the latter. Lenny expected to enjoy advising and starting a company but both drained him, while writing consistently energized him despite being hard. Simple, but hard to follow because the pull toward prestigious moves is strong.

  • After each call, hobby, or task, notice if you feel energized or drained
  • Do more of what energizes you and less of what saps you
  • Lenny found advising and company-building drained him; writing energized him
  • It's simple advice but hard because prestigious paths exert a strong pull

“my whole strategy was just do more of the things that energize me and do less of the things that de energize me”

Lenny Rachitsky · 38:30

“I want to chase that I want to go after that”

Paul Millerd · 37:30
#energy#self-knowledge#work
Takeaway42:30

Dance With Your Fears Instead of Solving Them Away

Paul says existential fears about money, health, and importance never fully disappear on this path — they periodically punch you in the face. Rather than escaping them by getting a job, he has a literal conversation with his fear: acknowledge the money worry, admit he can't solve it, and note that six and a half years in, it's still working. The comfort comes from the fact that what has lasted this long will probably last longer.

  • Existential fears about money and health don't go away, they resurface as small daily worries
  • Getting a job to make the fear disappear is off the table, so you must live with it
  • Paul literally talks to his fear: 'okay I see you, that's real'
  • Reassurance: something tends to last about as long as it already has

“oh we're worrying about money today okay I see you yeah that that's real yeah I don't know if we can solve that”

Paul Millerd · 43:00

“it's very important to like dance with your fears and really like get in with them”

Paul Millerd · 44:00
#fear#money#mindset