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Season 2 Episode 10
In this episode I sit down for a conversation with Paul Millerd, a writer, creator, and consultant. A few years ago Paul had everything he thought he wanted from his corporate job at the most prestigious consulting firm in the world. But after realising he was on the wrong path in life, he decided to walk away and figure out how to live a life that actually mattered to him. In the conversation we talk about his book The Pathless Path, the ultimate companion for people struggling to figure out what to do with their lives, which traces his journey from certainty and tradition to uncertainty and fulfilment. So if you’re thinking about leaving your job, taking off on a new adventure or simply wanting to approach work and life with a little more curiosity, this episode is for you. Enjoy 🙂
00:00 Intro
01:43 Your background
08:40 How do you tackle “I need money vs this job doesn’t bring me joy”
15:14 The 3 step framework for figuring out your path
20:41 Figuring out your passion
28:40 The cost of life fulfilment
34:59 The excitement of uncertainty
38:06 Figuring out what is enough
44:35 Following energy vs money
49:23 Slow productivity
51:55 Strategies for figuring out what you value
55:57 The attitude of experimentation
01:07:48 Long term thinking activities
01:10:24 On spending money
01:18:52 Your Book
🔗 CONNECT WITH PAUL
📕 The Pathless Path: Imagining A New Story For Work And Life –
🎥 YouTube Channel –
🐦 Twitter –
💌 Boundless Newsletter –
🎙 Podcast –
🔗 CONNECT WITH ALI
🎥 YouTube Channel –
🐦 Twitter –
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💻 Website –
👥 Linkedin –
📚 RESOURCES MENTIONED
David Whyte –
Rebecca Solnit –
What is enough? Article by Paul Jarvis –
Cal Newport On Slow Productivity and the Anti-Busyness Revolution –
Slow Productivity: The Antidote to the Epidemic of Busyness (Cal Newport on The Tim Ferriss Show) –
Tuesday’s With Morrie by Mitch Albom –
Tiago Forte On Deep Dive –
📄SHOW NOTES & TRANSCRIPT
Visit the website for the transcript and highlights from the conversation –
🎙 ABOUT THE PODCAST
Deep Dive is the podcast that delves into the minds of entrepreneurs, creators and other inspiring people to uncover the philosophies, strategies and tools that help us live happier, healthier and more productive lives.
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👋🏼 GET IN TOUCH
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PS: Some of the links in this description are affiliate links that I get a kickback from 😜
What would happen over and over again is People would tell me things and I'd be Like Have you shared this with anyone Well I've said like a little to my Spouse but like I can't talk about this With anyone so I was like oh wow what I'm writing about is like this hidden Knowledge that nobody feels they can Talk about publicly Paul has written a Fantastic book called the pathless puff Of which I have about 10 copies here in The office because I give copies to Anyone who is struggling to figure out What they want to do with their lives I Went out for a motorcycle ride the ideas Just came to me and I just broke down in Tears I realized it had like everything To do with my parents they didn't go to College they had to do the default path And I realized what they gave me was the Freedom to dream it matters to like Dream do Brave things I really think This matters and I think I can help People with this stuff and I'm just Gonna say it Paul has a super Interesting background he used to work In a traditional field in management Consulting but then he quit his job to Kind of wander this pathless path and he Writes a lot around how do we think of What a career means as soon as I left my Job I saw sort of dealt with this jolt Of reality of like this increased Freedom and space in my life and then in
2020 the whole world sort of like showed Up like asking these deep questions About work and my readership just like Exploded the old formulas of what led to Career and like life success and Fulfillment and stuff like you know just Get a job and work your way up at the Company and get the company car and all That kind of stuff that's not really the Formula that works anymore I think Paul's ways of thinking about this are Incredibly inspiring so if you've ever Thought you're not really sure what you Want to do with your life if you've ever Had a doubts about are you really in the Right sort of career I really hope You'll get a lot of value from this Conversation just a very quick thing Before we get started if you have not Yet subscribed to the podcast either on YouTube or in your favorite podcast app Of choice then please do it really helps Us out a lot so Paul welcome welcome to The show thank you so much for coming on How are you doing I am excited to be back talking with you I think we talked almost like two years Ago at this point the first time so Excited to dive in and catch up on both Our Journeys yeah that would be sick um So I've been every every time I have a Bit of a crisis in my life trying to Figure out what I want to do I always Think of you and I would think of your
Writing and your book and your uh your Newsletter Um so it's all just like I mean you're Sort of my Um I don't know my my life path pathless Path Guru um even though I'm sure you Don't intend to to be as such I would Love to get started with if you can just Uh how do essentially like how how did We get here um how did you and I ended Up and end up talking like this how did You end up developing this I guess Career that that you've landed into Yeah so so we'll have to dive into the What we're talking about when we say Words like career but Um my path grew up in a small town in Connecticut Um sort of uh always did good in school Stumbled into all these really Impressive career options in college Tried to break into them ended up Breaking into strategy Consulting for Like nine years loved my time working in That industry but sort of Ended up feeling more and more stuck the Longer I spent on that path and really Just desired to escape so I saved it It's not that large amount of money and Enough to kind of buy freedom for a year Wanted to run away from work and on that Journey which has been Five years at this point sort of
Discovered I didn't want to escape work I wanted to have a different Relationship with work I basically Wanted like things I could connect to Work that brought me alive things that Energized me Um but it was really a slow stumbling uh Awakening to that and a lot of my Writing was about that I think that was Some of the writing you connected with And increasingly in 2020 a lot of the World started paying attention to what I Was writing about Um before that I was kind of I didn't Really know if what I was writing about Was connecting with people but in 2020 Just so many people started showing up And reaching out and starting uh talking To me so that's a that's a pretty cool Journey of you know starting out with a Very very traditional career I guess and Then deciding to break away from it and And do your thing Um I cut so For for a podcast like this it's like There's I think this there's sort of two ways to Go about it one way is is where I Essentially act as an interviewer and Ask you your story because I know that Um I I imagine most people listening to This are not familiar with your story But I feel like because I'm already
Familiar with it that bit is less Interesting to me and I just want to Dive in I think that's a possibility Just like just sort of diving into Um the the things that I am currently Struggling with and I would just love to Get your take on it to be my personal Therapist for this uh how does that Sound let's do it I mean this is the Deep dive right so I love going deeper Anyway My story's out there people can find it They can get the the service level stuff And I think the more interesting thing Is that when we look at what other People do we tend to look at the surface Level stuff Um I was I was writing about this this Week and I sort of referenced you in a Post I was writing about which is like Just observing you you seem to have Found some sort of mode in which you're Able to show up in your life doing work You actually like doing and we can dive Into whether that is still true or not And to what degree Um but when people look at you they Probably look at like metrics right Metrics dollar amounts all these things But What I'm sort of talking about in a Relationship with work is like that Stuff is secondary And convincing people that is that is
Secondary is actually hard to do in Today's world because so much of the World is oriented around the idea that Like these metrics these sort of goals These titles are what matters if that's Secondary then then what is primary I Guess I think what I'm trying to say With work is that If we're just sort of showing up and Accepting what Society tells us I call This like the default path the default Path is what most people around us are Doing this is the story we grow up with In our culture that says you are Successful if you do these things get a Job go to school get good grades start a Family right And for most people that works pretty Well but increasingly large amounts of People one either can't make that work Or end up on that path and something is Just totally off Now I think part of the nature of work And it becoming abstracted we're not Using our hands we're not literally Connecting to what we're doing anymore People are just not as satisfied with Their work they're also taking these Ideas like meaningful work and trying to Fit it into a job container And they're not quite getting what they Want and so there's this sort of Confusion and people don't really know What to do with that feeling and I think
Those feelings are really human ones of Like wanting to matter Wanting to be useful wanting to feel Connected to the world to people around Us to ourselves And that those are the things I'm Arguing I think are worth finding Um But they're non-trivial to find and Might require blowing up your life and Doing things that don't look like Success on paper Yeah yeah I think that's that's why this Gets kind of tricky because You know just like just like you I've Had a very kind of traditional education Went into a job that was by all kind of External metrics and stuff like a Prestigious and useful and good for Society thing to do and in a way when I Decided to leave medicine to become a You know YouTuber for God's sake that You know there was a huge part of me That was like is this is this really Legit like yeah Um am I am I making the right decision Like will I essentially become a an Outcast or a pariah in society because I Have gone for this I've I've chosen to Leave something as Noble a profession as Medicine which saves lives for the sake Of making silly videos on the internet Um and so I think I think that's part of It it's like the what does what what
Will Society think of me but I think Also like I've had a bunch of Conversations with people since since I Announced my decision to leave medicine And stuff people now stop emailing me Having career crises that are I'm in This job and the job pays well but it's Not the thing I really want to do how How do you think about it in terms of Like we'll we all need money to survive Right like so there is a baseline level Of money that we need to get in our jobs And the legible alternative careers of These days actually become a creator has Become a lot more legible than it used To be back in the day become a Creator Is one of the things where there's Basically zero guarantee of making any Money at all at least for the first for The first while especially if someone's A complete beginner to it so how do you How do you tackle that thing of I need Money to survive my job gives me money But it's not the thing that I really Want to do I think the thing to do is sort of Unpair the the stories the ship the Shoulds we all have these like shoulds I Should do this I should do that and like Really what I'm urging people to do is Like actually reconnect with what how They're feeling It sounds so easy but even with like the Creator path becoming more legible more
And more people are coming to me and Saying oh I think I want to quit my job And do my own thing But then they'll list out a bunch of Like concerns and issues they'll have And I'll have to be like no like based On the people I know who are thriving in This path you are not those people So what do you mean I think in the sense I think in the sense that like they Aren't like valuing the freedom Of being on your own high enough they Aren't valuing they'll come to me with Like oh what if I can't make money what If I don't have predictable income and It's like you're not yet valuing the Upsides of such a path Like whereas a lot of the people I talk To Um they're not coming to me for should I Quit or not or how do I manage all these Fears they're coming to me and saying Like Okay I'm definitely leaving Can you give me like five pieces of Information to like help me improve how I'm doing this right and that's a Certain personality type that is like Craves Freedom needs autonomy over the How they're working like really wants to Like go on an adventure and do their own Thing and those are the people that are Going to like Thrive and make it whereas There's this meme now of like
I want to quit my job and do my own Thing or become a Creator because people Are seeing you can make money and gain Status in it though the status is Probably questionable at the beginning Um and then they'll say well like oh I I Don't know if I'll be able to like pay My mortgage and like I'm really Concerned that like this isn't like a Wise thing to do it's like those aren't Actually things that like the people Like Desperately committed to this path that Our thinking or say Just a quick note from one of our Sponsors and we'll get right back to the Episode and very excitingly this episode Is brought to you by Heights Heights is A brain care smart supplement that I've Actually been taking for the last 12 Months ever since I became friends with Dan marisota who is the founder of Heights and who we had on the podcast in Season one and this season of the Podcast we're also featuring Dr Tara Swart who is a neuroscientist and Psychiatrist so what is Heights well It's a brain care smart supplement Basically it is a supplement you take Two of them every morning like I do it's Like these two little capsules which Have omega-3 oil in them and they've got A bunch of multi vitamins as well they Have all of the details on the website
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Where I mean surely that's not what you're Saying like it's it's it sounds like What you're saying is you need to have The sort of Personality that is Desperately committed to the path of Freedom and autonomy and doing your own Thing And if you have concerns about money and Mortgage and stuff then you're not the Right person to be pursuing this Or is there is there more Nuance there I Think there's just that should like Raise a red flag right okay and be like If those are your if like Financial Security is your primary sick like Concern Like probably doing your own thing and Having freedom is also not your primary Concern Right so it's really just checking in With like what you value now you may Still be somebody that wants to do their Own thing and go on that path But it's really figuring out like okay How can I just test this And that's where like the biggest thing I've realized is I don't think most People should quit their jobs what I Think most people should aspire to get In their life is like a one to three Month break from worker mode Okay so worker mode is kind of like when You're hyper scheduled you're doing
Stuff constantly you're moving towards Stuff you're working for other people or You're just kind of in like an over Scheduled reality right And getting that space in your life to Sort of sit back and say like okay what Am I doing with my life what am I Actually afraid of what do I really Value Um how does it feel to be out of worker Mode do I feel really terrible in this Mode okay maybe my job has some hidden Benefits And like upsides and things I do value That it wasn't visible to me before So I think like what is really happening Is like these default scripts are so Powerful in society today That even the people that are thriving On that path don't really understand Like why they're thriving on that path So what I want people to do really is Like reflect more And say like okay what what do I value What are the costs I'm paying and what Path makes sense given those things uh Okay that's nice okay so step one figure Out what you value step two figure out I Guess how much that costs in terms of Time money freedom Etc like all the Things that it costs and step three is At a price worth paying Um yeah so for you I mean we we talked I Think a year ago before you were leaving
Medicine And I mean you it sounded like your Mother cares that you were a doctor Right and that that is a big thing for a Lot of people like the number one Question I asked people is like will the People closest to you in your family Judge you for making this decision Um And if so like is that a cost you're Willing to pay Right And I imagine like you sort of ran that Calculus and said okay something matters To me on this YouTube path and I think like even at the beginning You're downplaying it a little I think You're inspiring a lot of people you're Creating jobs for people you're giving People permission to create and do Things Um that are new and interesting Um Are you I mean you're still dealing with The challenge of like leaving that path Uh no not really anymore I think when I Yeah when we last spoke I think it was On your podcast Um I was still like I'm I'm not really Sure about it I'm kind of half in half Out But when I made the decision that yep it Makes perfect sense to leave at that
Point it felt like I had a lot of Clarity and Realized it it was really I think what Was holding me back was Feeling like oh to be honest I could Always go to go back to medicine if I Want to And in a way it was always an option and In a way it kind of still is an option But it took Lewis hose on School of Greatness podcaster prod me to be like Are you saying that if you just if you Were desperate for money you would Actually go back and do medicine Twitch my response was no like I can try Better ways to earn money yeah there are Far easier and more for me more Interesting ways to earn money and for Me what I realized is that You know if I if I Trot my life back From the age of like 11 onwards the Thing that I was doing in my spare time The thing that I was doing for free was Sitting on a computer programming and Making websites and trying to build cool Stuff and that was the thing I was Thinking about in the shower that was The thing I was doing at University While supposedly doing a medical degree The the main path was never the thing That I that brought me genuine Joy other Than when I was teaching other medical Students And so if I you know in this
Hypothetical worst case scenario where I Lost absolutely everything and I Remember you saying when you were when When you were online and my brother's Podcast that hey you know if you lost Everything and you're broken homeless Come over stay in my place and I'll I'll Feed him clothe you for a few months and I'm just like that's in a in a way Hearing you say that we just sort of Pointed out to me the absurdity of the Thing that I was actually worried about That like I'm am I really worried about Being broken homeless and alone and no One will love me forever and it's like Until I'd confronted that idea And realize that that's that worst case Scenario is actually not is a not that Feasible and B I can recover from it Because of friends family Network and Stuff Then it was more okay to be like you Know what 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 my mind That yeah I'm fully out of this now yeah That really gave me the peace to be like You know what this is fine this is great YouTube channel dies in the next five Years great no worries I'll start a tech Startup I'll learn how to code again I'll program in web3 solidity or Whatever the thing is there I'll
Continue to write I'll continue to teach And I trust my skills in being able to Make money off of the back of those Things almost by default which means They don't rely it doesn't rely on Medicine to be the thing that I'm I'm Doing to make money Yeah I I wrote about this in my book It's it almost sounds like you had a Similar path to me I grew up playing on Computers building websites screwing Around doing like earning money on Random things online selling things on EBay participating in these online like Simulation NBA leagues and then when I Graduated college The tech economy was booing and I went And joined strategy Consulting and made PowerPoint slides And like in in my day job I was still Like reading tech tech blogs and like Still screwing around with websites and Writing online and I just wasn't paying Attention to it Um so I think it's a good thing that These paths are becoming more legible But for me it was like oh I sort of had this moment a couple years Into my journey Um I was like writing doing things Online it was like oh wait I'm doing Exactly what I was doing as a kid It just took me 15 years to remember This is the things that energized me and
I liked yeah Yeah Um do you ever okay so I often hear from People okay I'm just going to zoom out a Bit and yeah and so so we're talking Step one figure out what you value step Two figure out how much it costs and Step three make it happen and so right Now I guess we're talking about step one One way of figuring out what your value Is thinking about what are the things You were doing as a kid what were the Things that genuinely brought you Joy What are the things you do outside of The day job that you would do for free What are the things you're thinking About in the shower Um one I have I've spoken to a few people who Say that you know when when it comes to This idea of essentially follow your Passion and figure out what your passion Is that I don't know I don't really know what I'm passionate about I go home and I Watch Netflix and I scroll Instagram and Occasionally I'll post a photo on Instagram but like I don't really have Any clear passions beyond that like I Don't know how how can I figure out and And you know I've I've got my my day job As a Management Consultant for example Or a strategy consultant but beyond that I I get home from work at like midnight
I have to wake up for work at 7am the Next day I don't you know I kind of want to play The guitar but like I've never picked up A Guitar because your work is just too Busy um do you ever get sort of Questions from from people like that how Would you go about I guess giving advice Or giving suggestions to people in that Position but I can I mean I can share my Story that was me The reason I did not leave my path Sooner is because I didn't have any Imagination for what other possible Paths or lives I could take I was mostly Surrounded by people like me doing Things exactly like I was Um who are also not cultivating an Imagination of different possible lives So I think what I would say like Basically what I say with to people now Is like different states are possible There's this state possible where you Can be so energized and like discovering Ideas And learning new things and reconnecting With that childhood Joy like that state Is possible I think it is possible for Most people now knowing that state is Possible How can you raise the urgency in your Life to like go find it now I don't Perfectly know how to find it but there Are a number of things that can help you
Find it like certain things like Health Crises will force you there yep Um I don't advise those right Um losses of people in your life can do That for you I think like the combo of a Health crisis and losing my grandfather Really like shook me and made me reflect On like What mattered but still it only Planted the seeds Um that I didn't fully explore even Until I left my job and I think a couple Things two two of the most powerful Experiences for me one was after seven Months of freelancing I decided I would Not look for any work and I would not do Any work Um that I wasn't like fully drawn to do And I just sort of woke it up woke up I Wandered around Boston I was like Writing I launched my podcasts at the Time I wasn't trying to make money Because like I didn't know how to make Money in the Creator economy at that Point it wasn't called to create our Economy Um and Like I just like it felt right Like I was just like something feels right I Don't know what this is but I need to Follow this and I have this sense that I Had to protect like the writing Um the things I was doing Um and like making money was like I'd
Figure out ways to do that but like I Had to protect that time and the Autonomy and freedom to do those things Um so that kind of committed me to the Uncertain path Um and then the second thing was really Just traveling And moving abroad to Asia I had started Freelancing again but moved to Asia and Like couldn't find remote freelancing Gigs like I just like was failing Um so I didn't have anything to do also Was a lower cost of living and I sort of Just Like showed up and did the same thing And again like I started writing again And like I started to slowly realize Writing is writing seems really Important and I reflected back and it's Like oh wow I've been writing like every Year of my life in some form Um so in 2018 I just decided like right I need to pay attention like if writing Disappears in my life something has gone Wrong So that is the state I need to come back To you need to protect that at all costs Now how I've made money has varied in so Many different ways over the past five Years but like the writing has never Disappeared Yeah so it sounds like part of the Figuring out of what you value is Finding the space to take a break away
From the I guess rat race of continuing To You know continuing to be in work mode And in a way figuring out like re or Almost realizing what you naturally want To spend your time doing yeah and maybe For you that sort of naturally just took Over your life like you're already doing Those things Like I think spending 10 years in the Corporate world sort of numbed my Creativity and Imagination In a way maybe if you start thinking About these things earlier and younger It doesn't affect you as much But a lot of the past five years have Just been a sort of unlearning of like Certain cynical modes being like I don't Know a little too passive a little too Powerless and like realizing oh I I can Show up and do things I want to do What do you mean So in the sense that I mean when you're In the corporate world even if you're Like in an impressive position you're Still constantly asking for permission And you're constantly being told no you Can't do things Hey this cool new tool we should try This you can't just like update a Website at a company Like I can do that now I can just like Update a website and come up with a new Service that I'm offering people and
Just do it in an hour Um that's like a sixth month to two year Process at a company sometimes So like going from that state of Possibility which is like very little Possibility you start just like giving Up Ideas of what's possible to like having To be on your own and self-employed and Starting to like okay how do I Regenerate that like creativity energy Like possibility for life Um And I think this is why I love following People like you I sort of just like I See people like you and other creators Come up with ideas like oh wow that's Really interesting I never thought of That I could do something like that in a Different way in my own unique way Just a quick little break before we get Right back to the episode and that's Today you know this episode is very Kindly brought to you by short form Short form is the world's best service For reading summaries of books but it's More than just book summaries what short Film does is it basically creates a sort Of study guide for tons and tons of Different non-fiction books from all Sorts of genres from self-help and Personal development to money and History and philosophy it's just got Loads of really interesting books and
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Shortform.com forward slash Deep dive And firstly that will give you a Completely free five-day trial where you Can try it out and see if you like it And it will also give you 20 off the Annual premium subscription which is the Thing that I personally subscribe to so Thank you so much short form for Sponsoring this episode yeah yeah I Think Often I find kind of through Conversations with people that Another thing that holds them back is so For example a you know a close friend of Mine is a highly paid strategy Consultant and she's been toying with The idea of quitting the job Um but one thing that's been holding her Back is the idea that oh currently in my High paying job as a strategy consultant I am making X amount of money which is like I don't Know High six figures or something like That or low six figures and therefore in Order for me to quit my job I need to Make sure I can make the same amount of Money doing something else and it's like Oh but I can't make the same amount of Money doing something else because it's Oh my how the hell do you make six Figures a year doing good right you know Doing your own thing therefore I Couldn't possibly quit my job because I Need that money to be able to 10 years
From now send kids to private school or Like you know I wanna I wanna save money I want to get on the property ladder and Therefore I kind of have to stay in this Job because of them because of the the Golden handcuffs in a way Um yeah how how do you how do you Approach that that's that's the cost Part I've never matched my salary when I Left five years ago Um this is the first year maybe I will Come close Um but I don't know and then it's Uncertain after that so like This is like what costs are you willing To pay for me I was willing to pay Enormous costs because I had sort of Discovered this path is not a winning Strategy for life for me I was so Certain After 10 years on that path that like if I spent five more years in that path I Would definitely become less of a person I was proud of And that was so incredibly costly to me That like replacing my salary was like This is Trivial like this is my life And I think I mean the thing that c did that for me Was five years before quitting my job Like a Health crisis I was out of work And I had sort of lost my identity I was Just sitting around and like I Desperately wanted my identity back and
I went through this reflection exercise Of like what would happen if I couldn't Work again it was like oh I'd be okay Like I'd have my family I'd have people To take me in that's why I make the Offer to you and the offer still stands I'll take you in if you uh go a few Months without salary Um but Yeah it's I was willing to give it up so Like this is why I share my income too Like my income the first five years like If I look after tax it was like 45 Because I was freelancing then like 30 Then 25 and then I think last year was Like 55. [Music] Consulting job is very low Yeah and I was making I think my final Year it was probably about 170 180 us a year and when I left I had About 50 Grand in savings Um so I sort of said okay I can live for A year on 50 Grand of savings I need a year just to like Figure out what I want to do with my Life like my service level plan was like I want to be a freelance consultant but I sort of discovered quickly like oh This is just recreating my previous life But like slightly less work Um but in that space the less work I was Able to get enough like breathing room That was like oh I wonder what would
Happen to my life What are the possibilities if I like Keep following this on certain Journey So like this is the equation I talk About in my book like it sort of flips Once you add this sense of wonder Possibility to an uncertain Discomfort uncertain discomfort is Terrifying yeah that's pretty scary but If you pair it with Wonder like ooh what Might also happen Then you can sort of in immunize Yourself for a certain period of time And I mean this is when I start reading Like people like David White and Rebecca Solnit and like people that are like Giving me courage to like follow these Uncertain Journeys and this is when you Need poetry and literature and like All these people that are like trust the Flow of the universe like you need that Stuff because like you have no idea what You're doing and then when you're doing It at the beginning you I also like People would ask me what are you doing And so like I would feel the need to be Like I know exactly what I'm doing Here's my is I had no idea what I was Doing and I was terrified now you like Every time somebody asked me it would Scare me Um so yeah you sort of have to have this Surface level story but at the same time Just this deep sense of like okay
There's a direction I'm gonna follow it But I I may also be wrong like that's The deepest humility in the world like I May be wrong And I think that's the best way to Follow any path Yeah no that's nice yeah I think I think It was when I added in the component of Wonder that I still suddenly started to Feel okay with the decision to leave Medicine and pursue this uncertain puff Because and with with medicine and with Most traditional careers there is a Level of certainty you get you know that Okay if I can if I stick at this for Long enough I will get the promotion I Will apply for specialty training in X Number of years then it will take eight Years to become a consultant and then And then I'll die Um but with the uncertain path it's like Uh right right now I mean I don't really Know what I'm doing my YouTube channel Is kind of going well or maybe it's not Maybe my podcast is doing well or maybe My side little software business is Doing well or maybe I have nothing at All I have no side hustles and I just Know I've got enough savings and enough Of a family and friends safety net to be Able to spend a year experimenting and Then I know that if that experiment Fails and I ended up end up needing to Go back to a job great I'll just get
Another job but if the experiment Succeeds I guess kind of the upside of That is that I have figured out a way to Live my life Um that is more in line with the person That I want to be And for me it was in there was a lot of A lot of fear around this uncertainty But when I added the component of yeah You know it would be interesting it'll Be kind of interesting to see I'm sure I'll be able to figure something out and Even if not worst case scenario I've got Family that I can only I can lean on to Kind of help help prop Me Up that made It feel much more okay and even now even With like all of the traditional metrics Of success on the YouTube channel and The business and everything I still feel The sense of like five years from now I Have absolutely no idea what I'm gonna Be doing oh yeah but it's like a sort of Embracing that with a sense of uh Excitement curiosity Adventure which I Managed to do about half the time the Other half of the time it still feels Really scary and I think oh my God I Don't know what I'm going to be doing Five years from now Well yeah and I think that's the part A Lot of people don't talk about on these Paths and I think people probably miss When they look at people they deem Successful right they're mapping their
Idea of success onto you now like I see Some of the success you're doing but I Also know for sure you're in the same Point as me of like you have no idea we Have no idea what's going to be Happening in five years Yeah as opposed to being in a more Traditional career path Um But I think one of the benefits of an Uncertain path is it forces a constant Grappling with the uncertainty like one Of the things I didn't realize in my Previous path Was that no one ever asks you why are You doing this Oh like no no one deeply asked me why Why are you working as a strategy Consultant why would you pursue this Path it was so obvious right because Like Everyone thinks it's impressive and like Everyone knows you make like good money Um then as soon as I quit people like What are you doing how could you give up This job what's your plan don't you want A family don't you want a house don't You worry about this and like you start To realize everyone has these fears and Then you realize oh crap I have them too And now I have to face them So like I think what I've learned to do Over the the journey over the last five Years is you sort of are able to take
These massive ambiguous like fear of Death fear of being loved fear of not Belonging and like break it down into Like many daily existential crises So now like I can kind of like in a Mindful way like I see the like fear of Uncertainty coming up and I'm like I see you I see you all right money Insecurity fear going broke been here Before all right we can deal with you Gotten through this before going through Stretches of not making money for a Couple months we'll be fine Um but it's still there I don't know if It ever goes away I was tweeting the other day about like You know what it feels like to hit 3 Million subscribers and kind of How It's A sort of metrics or a double-edged Sword and you linked me to this article Uh by Paul Jarvis about finding your Enough point And that like that was that was a good That was a good article I I was like There's uh It's always nice when you post what You're thinking on Twitter and someone Responds with the absolute perfect Advice that you need to hear Um This this idea of Figuring out what is enough is something That I continue to Grapple with In the sense that
You know I'm in a very privileged Position now where it's like oh the Business is growing and growing and Growing and it's like now I need to Decide how much do I want to continue to Stress out in terms of you know numbers Going up but another part of me is also Like I need I need to make sure the Numbers continue going up because I need To have a safety net safety net of 10 Million in stocks and shares and crypto And real estate and crypto is a bit Volatile anyway so I need to make sure That I have at least enough money to be Able to four percent return make at Least 100K a year off of just the Investment returns and it's like the Point of enough I haven't really figured It out figured out what it is but it Keep it's a very high number right now And it keeps on getting bigger and Bigger as the business grows and I know That that kind of thinking left Unchecked or like not examined it's just Like generally very unhelpful and not a Way to live a live a happy life um I Wonder if you can share your perspective On how do you figure out what is enough For you and at what point you can stop Pursuing more in the sense of money and Fame and numbers and and ambition and Promotions and all of those traditional Metrics of success Yeah so I think this goes with another
Default script the default like Drive in our world is more It's always going to be more so unless You're explicitly defining An alternative to more it is more right And I think that is good to sort of Acknowledge because I mean you have Employees now So like unless you're telling them we're Not trying to make as much money as Possible that is the Assumption in like A business and a job things right Um so you could probably do interesting Things I mean like Paul Jarvis to find Okay I'm not hiring employees ever that Is a constraint he created that doesn't Limit the amount of income he can earn But it does limit it to a certain degree Um yeah and then I think what you can do Is like just I attempted to write my own Definition I can read mine I wrote it in The book yeah what is yours Foreign Defined it in the book so I basically Just decided like Jarvis is like I Should just Define what enough is and Like write out my definition So Let's see bringing up my Kindle Highlights from the book as well Yeah you get the Branding so Um enough is knowing that no amount of Money in my bank account will ever
Satisfy my deepest fears it's knowing That I have enough friends that would Gladly open their door and share a meal If I was ever in need it's the feeling That I've been able to spend my time Over an extended stretch of time working On projects that are meaningful to me Helping people with a spirit of Generosity and having enough space and Time in my life to stay energized to Keep doing this over the long term Enough is seeing a clear opportunity That will increase my earnings in the Short term but knowing that saying no Might open me up to things that could be Even more valuable in ways that are hard To understand enough is knowing that the Clothes fancy meal or latest gadget will Not make me happier but also that buying Such things won't mean that I'm going to End up broke enough is having meaningful Conversations with people that inspire Me people that I love or people that Support me nice How how often do you return to that Definition like how is it does it help You in kind of day-to-day life Yeah I I think by writing these things I Think by doing a lot of my writing it's A sort of ongoing reminder to myself That I'm trying to live a sort of Principled life And I think by writing about these things
I'm a lot of what I'm trying to do is Just hold myself accountable like I'm Saying these things matter like putting Generosity over making my own money okay How do I actually do that Um am I bullshitting on that like how am I actually doing that and then also not Being too stuck to these stories I tell About myself And like trying to do things just to Like virtue signal like I want to do Things that are really aligned with like How I'm wired I love helping people I Love like connecting with people I love Helping random people on the internet And like navigate their paths I love These things and like that's why I've Kept doing them Um but I don't want to be like Unnecessarily tied to like oh I have to Do these things because I'm writing About it um so it's just constant Reflection and trying to be honest with What I really care about Just a quick note from one of our Sponsors and we'll get right back to the Episode and this episode is very kindly Brought to you by skillshare if you Haven't heard by now skillshare is one Of the world's leading platforms for Online classes for online education They've got thousands and thousands of Classes on all sorts of topics from Business entrepreneurship lifestyle
Design cooking interior design loads of Stuff and very excitingly I have Actually been teaching on skillshare Since 2019 and I've got 13 classes on Skillshare yes 13 classes and you can Access all of them completely free of Charge by going to skillshare.com Forward slash Deep dive and that link Will give you a free one month trial to Skillshare during which you can watch Any and all of my classes one class you Might be interested in is my YouTube for Beginners class if you've ever thought About starting a YouTube channel this is The class for you I'll take you step by Step across like three four hours Something like that through all of the Steps you need to take to make your First two videos on YouTube how to do The channel art how to think of a name All of that fun stuff and loads of People have taken that class and said That that class was so good that they Would have literally paid hundreds of Dollars for it but you get it completely For free on skillshare by going to Skillshare.com forward slash deep dive After your trial's over you can choose To continue the subscription if you like And you can access the thousands of Classes skillshare house from other Teachers including people that I know People I'm friends with like Thomas Frank and Nathaniel Drew but yeah the
Main reason to check out skillshare of Course is that you want to check out my Classes if you want to learn about Productivity and video editing and Youtubing and even cooking so head over To skillshare.com forward slash Deep Dive and thank you so much skillshare For sponsoring this episode uh one thing I wanted to ask you about is kind of This idea of following energy versus Following money and I wonder if you can Elaborate on on what you mean by that There's a lot of people that are very Hyper analytical we grew up in a world That clearly values money and it's very Easy to understand Like things that turn into money I think the mistake is over indexing on That and just not paying attention to Like what the actual energy of like what You're doing is And Like I think people can get trapped in Like local minimum Where they're optimizing around like Something that produces money Um and possibly even miss out on sort of Those unknown opportunities that can Emerge From just giving yourself time to Explore other things or saying no to Those things Right Yeah I imagine early on in doing YouTube
Videos You sort of noticed oh I like this Like in some ways like you can't Actually make it To where you are now without actually Being energized by what you were doing Yeah absolutely especially at the early Stage yeah So I think this advice is like super Important at the early stage where like People think the issue especially like If they want to follow a Creator path It's like I need to make money as soon As possible I think a lot of times that will Short-circuit this exploratory mode and Like sort of finding paths where you can Ride that energy wave Um Such that like people can't actually Make it to that second phase where they Can commit to that path So there's a lot of different ways you Can do this right you can do like all Right I'm gonna do a 30 day challenge Where where like I call it ship quit and Learn Um Ship 30 posts 30 videos 30 something Even do like seven do it small enough That you know you can do it Design it to quit But like in the process of doing it
Notice oh do I like this do I want to do More do I find myself trying to learn More things if you're like resenting Doing the post on like the fourth day Like you need to pay attention to that You'll never make it to a hundred I love that that's sick writing the Energy wave yeah this is like basically The concept of my whole book uh it's About like how the secret to effortless And sustainable productivity is to Figure out what energizes you and Go towards that and if you're having to Do stuff like your day job that doesn't Energize you then there is a way that You can approach it to an extent that Makes it more of an energy source and Less of an energy drain And I think that's why for me like Making YouTube videos doing these Podcasts the the stuff I've done has Almost never felt like uh chore there Are still you know there are times when It does where it's like oh let me Sponsor deadline we should probably get That video tomorrow Um but those are very very few and Broadly I feel enormously energized by Doing Videos and stuff and that's great and It's just such a competitive Advantage As well in the sense that if someone Else is trying to be a YouTuber because They want to make money but I'm doing it
Because I genuinely enjoy it and it Energizes me it's like you'll win I am Way more likely to keep going than the Other person that is not going to see Any kind of momentum on the money front For a while yeah like I mean I see a lot Of people start newsletters and stuff And I sort of know I'll probably make it To like a thousand issues of my Newsletter Like I've I've tapped into something and So I can play a a slower and stupider Game in some ways like I don't need to Worry about monetizing or scaling or Growing it or being super successful Because that's sort of taking care of Itself and like as long as I protect the Energy that like is naturally going There anyway I'm gonna keep doing it So then in some ways ambition And how much money or like how Successful you want to be is really a Question of like speed and time So it's like and I think I've started to Like rethink ambition over the past Couple of years as I've like gotten more Of a footing on my path it's like okay I Can be ambition ambitious just over like A longer stretch of time Like I don't need to crush it in three Months but like I can sort of have a a Sensible plan to like take the three to Five year plan and like because doing it At that speed will be a little more fun
For me yeah You know I was listening to a good um uh Cal Newport chatting to Tim Ferriss on Tim ferriss's podcast Yeah yeah slow productivity or low Productivity yeah where it's like you're You're optimizing for creating Meaningful output across a 10-year time Horizon rather than a 10-day time Horizon or a 10 week time Horizon and That just means that you know if I was Thinking about can I make cool stuff in The world in a way that I enjoy and that Help is helpful to other people that Energizes me but I'm doing it over the Next five to ten years then it means That I probably spend more time deep Working on my book for example rather Than feeling the need to every single Week bang out another two YouTube videos Because that's all very sort of Short-term productivity whereas the more Longer term tends to be the thing that's Uh but potentially the thing that is Tends to be a little bit more needle Moving but also I guess it just depends On what what you enjoy there are some People that love the high octaneness of Putting out content every week or even Every day or even multiple times a day And there are others of us that would Rather kind of take it a bit slow and as Long as We're doing the things that we enjoy
We're being we're feeling energized by Them and I guess they're useful to other People in some way then that's a that's A reasonable path as well I think in the Last year I've sort of realized I'm on a path that's really aligned with What I value So I I don't pay much of a cost for like Worrying that other people see my path As low status I'm like huh whatever Um I also am not too worried about like Not making tons of money I just like Don't have much material aspirations nor Does my wife Um So And I highly value the like creative Connection and that creative mode like It's so valuable to me it gives my life So much energy and Um Like just keeps me going like at such a Deep level so I can sort of look around and like see People panicking about money like Starting in this path is like I'll Probably still be doing this in like 20 Years yeah and the way the internet's Going like you can sort of just bet on Like okay you'll probably be okay Because like this is just an expanding Space and like you'll figure out some Stuff you'll slowly get better maybe
That's slower rate than other people but You'll be fine Yeah Yeah no like that okay so so coming back To our sort of anchoring three three Part framework of like step one figure Out what you value step two figure out How much it costs and step three Figure out if you're willing to make That trade so we then figure out what You value we talked about like the Shower test or the free time test what Do you find yourself drawn to in your in Your free time Um I love this idea of yours of like um Ship learn quit organic ship learn quit Try something else ah chip quit learn That's one so try try something out you Know thinking like oh maybe I want to be Some kind of YouTuber okay cool try Making videos for four weeks once a week And and see and see how you feel uh Learn from that and the more of these Experiments you run on yourself the more Of a barometer you get for what are the Things that I value and one way of doing That is to figure out did this thing Give me energy did I feel almost Effortlessly incentivized to continue Or did it feel like a chore And I guess if I'm if I think of people I know who say that they don't really Have any hobbies and they don't really Know what they value they tend to have
Done very few experiments of this kind They'll have ideas in their head of like Oh maybe it would be cool to do XYZ but Then they won't they won't try it out Because and you know this is I guess the kind of the way we're taught Is that like The festival perfect yeah it has to be Perfect and it has to be long term it Has to be sustainable it's like oh maybe I want to be a YouTuber but I can't Imagine what that looks like for the Next 10 years it's like don't worry About the next 10 years I should get I Should take this advice myself don't Worry about the next 10 years just try It for now try it for a little bit and See if energizes you and if it does then That gives you a decent data point then That is something that you potentially Value so other than what do you what do You find yourself doing in your spare Time and run experiments and see what Vibes with you do you have any other Strategies for helping helping people Figure out what they actually value in Life I guess that's a big question yeah I mean what what you value I think Reflecting asking the hard questions we All know the hard questions we need to Ask Um it's just really sitting down and Like grappling with our answers Sometimes we don't like our own answers
We hide from them I think in terms of like finding things You actually want to do What I've found is that if you give People enough free time and this is why I think like finding a way to take a one Month sabbatical in your life is so Vital to like reclaiming the energy in Your life Like people will just start doing stuff In like 99 of cases of people I talk to There they start to oh wow I literally Forgot I liked playing this instrument As a kid and I just started doing it And like you hear these stories over and Over again Um oh I started volunteering at a local Garden I was just like walking around my Neighborhood and I like remembered I Like engaging in my local community So it's like we all have this like I Don't think this is a hard thing to do I Think the thing that's hard is we often Have things that out compete or zap our Energy Um and the thing that's worth noting is Like this is why it's so important just To like get reps of experiments like This is why I love helping people to Like just start stuff Do a hundred tweets do five posts do Five YouTube videos like even just do One Um just to realize you can do stuff in
The world we don't need permission Anymore we have more freedom to do more Things than like at any time before it's Such an amazing time to be alive Um and then these things compound like I See even you like I feel like you're Launching and trying new things like all The time And that's that makes so much sense Because you realize like the more Experiments you do like you constantly Want to like keep learning and like keep Finding those new spaces those new ideas Those new avenues those new energy slip Streams Yeah yeah and I guess as we as we run The experiments like if it whether it's In my personal life or as a team in the Business where we're getting really Useful data points from them like we you Know we run an experiment thinking oh we Should totally start a whole new YouTube Channel the part-time Creator Academy Teaching people how to be creators then We tried it you know planned it out did The whole thing Um bashed out you know we had like set Like seven videos filmed and ready to go And it would you know just the feeling Of the project was so energy draining Like oh this is such a heavy lift we Don't have the capacity to do this if we Wanted to do this thing it would require Us to hire an extra probably five people
Or cut some other projects and In the end we decided you know what Let's take the loss on this uh it was an Experiment we tried it out it didn't Work the idea is still good someone Someone could totally take that idea and Run with it but it's not something we Want to do right now and then we pivoted From that into thinking what if we just Did it as a newsletter and a Twitter Account instead it's like oh all of a Sudden it's like that feels like that Feels like all of the weight has been Lifted off because now that's a thing That you know other people in the team Can write and can take ownership of Rather than me having to be on camera at All times so that was great so now we've Built this thing and we're like okay Cool let's connect it to the course and Now that's sparked the opportunity to Potentially collab with other creators And create courses for them because That's fun and we're all about sharing Ideas and it's like doing an experiment And just sort of doing it quickly and Realizing okay what is the data what is The learning we've gotten from this Experiment and even if lots of time and Money has gone into it you know that's Some cost fallacy it's way better to Quit a thing early or could a thing when You know it's not right than it is to Worry oh but we spent like six months
Preparing for this already And so I think that attitude of Experimentation applied to life in General you know like I've been saying For the last couple of years I really Want to travel the world and do the Digital Nomad thing the appropriate Response there and the advice I would Give to someone else is well just try it Out for two weeks see what happens and So right now I'm in Wales we're on this Four day team Retreat we're still making The podcast happen the internet's a bit Sketch it's cut out a couple of times But oh well it's working the setup looks Good No One's Gonna explain about Quality issues because the camera's sick Um this is great I'm currently looking On over over these like ridiculous Fields that like some cows and sheep and Stuff and this is so nice and so what I Should do is probably experiment with Okay my hypothesis is that I think I Would enjoy the digital Nomad lifestyle Great let's experiment let's try it out For two weeks let's see what happens Cool I enjoyed that all right that's That's good data points let's now try it Out for a month let's now try it out for Three whereas I think the thing that's Holding me back on that front is Thinking that oh in order for me to Experience the digital Nomad lifestyle I Need to wait for the conditions to be
Perfect I need to have a whole year Right where I have nothing to do and no Responsibilities and then I can take Away get a one-way ticket to Bali or Something like that and that's just such A dumb way of looking at it and I it's Only now saying this out loud that I Realized that that's subconsciously how I've been approaching it because I Haven't been consciously thinking about What is the smallest unit of Experimentation that I could apply to Get to gather data about this hypothesis That maybe I would enjoy this kind of Lifestyle Yeah and I think this is a key point Which is like you're starting with like A story of like a script of like what a Digital Nomad should be When like what you're really trying to Test is like would it be cool to work in A different location than my home base Yeah that's it yeah right Um and I think where people get into a Lot of trouble on traditional paths or Other things is like when they're trying To be something Rather than like literally just be Themselves Be something rather than be themselves Okay like trying to imagine to be a Creator Yeah like ramdas talks about this idea Of like the this space suit like you go
On Earth and you wear this space suit of Like this person that's you And you're sort of Performing all these Roles and like Really The Human Experience is Remembering that like you aren't that Spacesuit You're just like This human body And like you're just living in the Present moment Um So what how how does that apply to like Work right we're like people don't want To leave their jobs because like I am a Consultant that makes this amount of Money and like I need to be that kind of Person that makes this amount of money Right when it's like the real question To ask is like are you feeling this fire In your soul that is telling you there Is possibility and wonder to be found in The world and like how long are you Going to not listen to that voice In service of like continuing to Maintain this beingness of that role and Identity yeah Yeah no absolutely Like even the the digital Nomad stuff I Sort of stumbled upon it by accident I Took a one month trip to Asia And I landed a freelance project right Before I left because Somebody reached out and I said like not
Available they're like we like your Background though can you please help us So I was like all right I'll do it 10 Hours a week from Asia for like double What I normally charge and they're like Fine I'm like oh wow so I like fully Funded my trip and then I found myself In Bali this is the first year of Self-employment Um I was staying at a 20 a night Surfer Hostel oh overlooking like Surfers with My friend and like I walked down the Rock Ledge to a cafe and I'm like Overlooking the ocean doing work paying Like way more than twenty dollars an Hour And I'm just like oh wow I never even Thought about the possibility of doing This yeah And I sort of had this like what else Like haven't I imagined and that sort of Just expanded my imagination and on that Trip I decided I'm gonna move back to Asia And like figure it out but yeah and I Really didn't have a plan and like I Really was almost like crippled by the Questions that summer from my family Like that people were asking what's your Plan like you don't have any money like You're gonna run out of money what are You gonna do for Health Care are you Gonna move there forever and like There's just a experiment I was gonna do
It for three months like I didn't have a Plan I didn't know if I would like not Have work Um but a month into my trip like it Started to change my life and met my now Wife Um and That sort of changed everything Um yeah yeah this is definitely Something I need to be I I I I want to Be and and will be more mindful obvious This attitude of experimentation like I Was I was good at it though Yeah no I think I'm good at it I think I'm good at it at work I think I'm less Good at it in my personal life Um I was re-listing to an an interview I Did with Noah Kagan on like back back in The day when I was doing live streams on The YouTube channel um because we Released that as an episode on the Deep Dive as like an in-betweener sword and One thing he said he was like hey you Know I've always been interested in the Idea of living in a van so I just rented A van and I'm gonna live in it for three Weeks And I was just I I was listening to that Like now two years later after the Interview thinking damn that's such a Good attitude it's like I've also kind Of been watching the van life videos on YouTube and thinking huh I wonder what It would be like to live in a van and
I'm just not taking that step to be like I could just rent a van for a week and See what happens And I've just been caught up in the Default script of oh I guess I'm living In London now I'm I guess I have a Studio in an office therefore I guess Every day I have to go to work and like On the weekends I guess I go home and See my family But I could do all that from move out And just to see what it's like living an Event like why why not and I was kind of Like thinking thinking to myself like That that exact thought process that you Had is like damn what other things have I just thought of that oh it would be Cool to do X and just not done the extra Step of all right how do I try this out For a few days or for a week or for a Couple of weeks or just like how do I Turn this into an experiment and let's See what happens I do wonder if in certain cities like I Was living in Boston in New York For a long time and in London if there's Just this sort of like gravitational Pull that Like Narrows out that imagination like I Think moving to Asia for me sort of gave Me this distance from my default culture That new ideas started seeping in in Interesting ways So I and maybe Wales can do that for you
Yeah maybe because like thinking looking At the hills and thinking you know what Yeah you're looking out at like a Vastness right yeah I'll turn the camera Around so the people in the post office Can see it if you're listening to this On the thing it's like it's just insane I'm currently sitting on a snooker table And there's this like enormous I mean I Don't think it's going to focus because The lighting's all off but it's just This enormous like vast expansive Hills And trees and stuff And it's just really cool it's a good Good place to yeah to be here for a Little reset and the other thing is that Even then it doesn't I think it's it's Easy to get too precious about this Stuff that oh yeah I need to go out into Nature so that I can think about my life But like for me if I had just spent a Set of five minute timer and just be Like for the next five minutes I'm just Gonna brainstorm cool that I can do For a week at a time I I would have come Up with living in about an hour I'll Just be cool and it's just I've never Had the thought that I'll let me just Spend five minutes thinking about this And then of course yeah I can do all This cool stuff and five minutes is not That much time but I guess it's so easy To get into again this default thing of Life going on where you just don't
Genuinely don't stop to think huh let me Just ask myself a question you know what Am I procrastinating from what's Something cool I could do what's Something that I would be glad I did 10 Years from now like these sorts of Prompts I think are really helpful in Just ex forcing yourself to just get Outside of the mode of like the mode of Life where you're following the script That you've always followed and just Actually thinking a little bit it Outside the box to use that to use that Phrase I think it's very hard I think Even on my path I sort of gotten a Routine of like living this sort of Simpler existence and doing the same Things over and over again And like I'm constantly amazed that like I'm Like oh I should have thought of this Idea earlier like recently I've decided To lean back into my podcast And I sort of came up with the idea of Like oh what if I like sought out a Sponsor and like I just put that in my Newsletter and then somebody reached out And said we'll sponsor you And I was like oh I could have like came Up with this two years ago oh yeah I was Thinking of sponsoring you as well I was I saw your page I was like oh we should Totally sponsor that podcast
Yeah and it's uh yeah it's just constant Challenge and I I think this is Something if you are going to be on an Uncertain path like This is a challenge and something you Need to have a plan for like how do I Continue to experiment how do I continue To come up with new ideas and like if You don't like doing those things like You probably shouldn't follow an Unconventional path one of the benefits Of like having a job in a more stable Career is like a lot of that thinking is Sort of just baked into the path for you Yeah now I would still advise you to Like figure out like if you really value Some of the benefits you're getting Um but you there's just less to worry About and sort of like constantly Refreshing your life and injecting new Things and into your path Have you gotten any mileage out of those Sorts of long-termy thinking type Exercises of like imagine yourself in Your deathbed and like what would people Say at your funeral that kind of stuff Do you ever think about that I think so a book that has really stuck With me is two sides with Mori it talks About this guy at the end of his life Um I quoted towards the end of my book Too Um he's sort of he's in his late 70s He's dying of Lou Gehrig's Disease and
It's doubly interesting because the Writer Mitch album is at the peak of his Work career and he sort of realizes that Oh this is my professor he's dying I Lost touch with him for 15 years because I got carried away in my career how am I Going to reorient My Life Um so it's a really powerful book Because It talks about this guy Mori who's Fully Alive and engaged with life at the end Of his life so I think a lot about role Models in terms of like how they're Showing up in their life So I really admire like older creative Men Like people like Mori his story Um I look up to people like Seth Godin I Think he's like in his 60s now he Probably doesn't want us like saying That but Um he's still connected energized like Seems Fully Alive with like what he's Doing Um I really admire people like Jim O'Shaughnessy who's like still injecting This playful curiosity Um at his age and like that's kind of Like my aim in terms of a state I want To arrive at later in life So yeah I don't think the way to get there is to Like play the like okay I need to play The retirement game of like maxing out
Of like aiming at a Target retirement Number Like can that help sure like I don't Want to be broke when I'm older But it's like I need to sort of like Have an intuition that I'm like headed Towards that state Um and this is what made it so easy to Walk away from my previous path I just 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 by who are like cynical Overweight slightly disillusioned good Bank accounts but like I don't know some Of them had been like divorced Disconnected from their kids like I Don't want any of that okay so we spent A bunch of time figuring out this whole Values question like what are the step One of the kind of Breaking away from the default path step Two we talked about uh what is the Figuring figuring the cost of this and We touched a little a little on the Money on the money side of things but I Wonder if you can elaborate on this like How do we genuinely figure out what it Costs to to have a to to take one of These non-traditional more Um uncertain paths yeah so the financial Costs are obvious right you're trading Like certain income for uncertain income And most people worry enough about money That they are hyper focused on this cost
The other costs you need to be aware of Are what other people think of you I and this is a really important one Especially the people close in your life Do not be surprised if you take an Unconventional path that you will Receive less support than you expect Because you will be feeling more Uncertain About your path which means you will Crave Like affirmation and appreciation from Others more and you will notice that the Lack of active encouragement from others Feels like you're not being supported And that can be really hard For people early on a path And figuring out like how you're going To deal with that and this is why I Think one of the most important things And a real reason to share Ideas in public and write about your Journey is to like find the others Like finding other people you can Literally just be around and you don't Have to have the conversation of like Why are you doing this don't you worry About X it's like no we can just sort of Like both exist in our uncertainty for Like not knowing what we're doing and Like Connect on that vulnerability It's a big reason why I'm in Austin like There's just a lot of people doing these
Weird internet online Creator paths and Like people in your audience or my Audience might look at us and say wow Impressive people But like We're kind of low status in the Normie World still Like if if I try to talk about what I do And like fancier circles people like What are you what are you talking about Why would you do any of this yeah Um so you sort of need Those connections of like people who do Understand you and and want to actively Encourage you this is why like I've Really tried to lean into like actively Encouraging and supporting people across All different levels doing these past Because like I want to keep people in The game because like I need friends Yeah Can we yeah like can we zoom in zoom Into the money point a little bit Because I think yeah there's there's Something there around the fear of uh oh The perceived cost in terms of money Being different to the actual cost in Terms of money Yeah I my relationship with money Changed dramatically From being employed to being Self-employed I went from making High income that was increasing
Throughout my career pretty steadily to Making no income for the first three Months after quitting my job And I sort of like had this bold hunch like I could figure it out but like I totally Underestimated how terrible it would Feel to not make money especially I was Living in New York spending like five Thousand dollars a month It felt so painful To like start to see my savings go down I felt terrible I felt like an idiot and I sort of realized like oh this was There the entire time It was just like I never had to stare it In the face When I quit my job so like I drastically Took action in both directions one was To like lower my cost of living and I Quickly like started dropping things out Of my life and almost bearing like no Cost like I just stopped going out to Restaurants I started cooking at home I Started eating much cheaper and I'm like What was I doing for the last several Years like I'm not less Happy by giving Up any of that but that was like a Decent amount of money I was spending And like Even I thought like I like kind of Needed those things right that was like Part of what made me happy and like Totally not true I didn't value it
Um and then lowered my call and then the The other side of that is like I think One thing people underestimate when they Go without income is like how motivated They will be I was ready to like do any kind of work For any kind of money at the beginning Of my journey like I like I held signs in New York like Walking around like trying to find People for a survey like I got hired for A gig to like do research for this um Private Equity Firm and I was just like Walking around like holding up this sign Trying to find people with wearing a Certain type of shoe and it was like I Don't care I'll do I'll do anything to Make money at this point make the pain Go away but like leaning into that to Like Realize oh you can ride this wave of Energy at the beginning I think that eventually like Mellows out A little so like what I say at the Beginning is like lean into your money Insecurity and like just go hard and try To earn money in a number of different Ways in your first six months but like Eventually you do need to shift into a Mode where like you're making money in a Way that's connected with yourself and That's where this like deeper stuff Comes in But then I sort of got stuck in this
Like minimized spend mode especially After moving to Asia I was like tracking Expenses like minimizing spend And I was short-circuiting my creativity I created a course at one point and I Remember going into a store looking at These webcams And like I it's like there's like 100 Camera and there was like a 40 camera And I just like toiled I ended up buying The 40 camera And like looking back this is so silly I Should have just bought like the 100 Camera it would have like raised my Ambitions a little And like I was just like short Circuiting my energy by like worrying Too much about money Um so I was playing accountant and I Read this book like I was playing Accountant Rather than like living my life so I Sort of just decided like I don't want To be spending my day tracking my Spending and counting my dollars like I Was using a spending app got my spending To under a thousand dollars a month like I was still pretty happy but like I was Playing accountant I wasn't actually Like living my life and that was when I Started like leaning back into like the Creating stuff like sharing on Twitter a Little more like writing a little more Publicly and like being a little Bolder
Um and digging out of that like even the Other day like I was thinking about Relaunching my podcast and doing an In-person one and I was like you know What like I'm wasting zero time on Buying the best equipment I bought like A 260 cam link I bought a share mic and I was like you know I'm not playing Accountant I'm just like gonna commit go All in and like I think this is a better Bet Um so I'm I'm still learning to like Play with money Um And investing in myself has been really Hard for me to do because I went into it With like I need to break even I can't Like spend more than I make I don't want To see my savings go down Whereas like now I'm five years in and I'm like I'm giving myself these pep Talks I'm like Paul you've sort of found Your footing you wrote a book about like Being confident on your path Like okay you can be a little Bolder You're not gonna turn into this hustle Bro like I don't think there's any Chance I'm gonna turn into a like hustle Pro productivity bro Um I'm not gonna start like money maxing Like I'm gonna be okay I can like be a 30 Bolder and like still Be myself yeah um Yeah
Um can we talk about the book a little Bit so how how did you how did you just Write a book yeah we gotta talk about Your journey too oh yeah we could do That but like yeah let's do yours first Yeah how did how did you just write a Book So mine was very emergent uh like I said At the beginning Um I was writing about this stuff from As soon as I left my job I sort of dealt With this jolt of reality of like this Increased freedom in space in my life And like what does this all mean like Why why was it so hard to leave my path Why was it so weird feeling when I Became self-employed so writing about That and then just consistently Committing to that after moving to Asia And then in 2020 the whole world sort of Like showed up Like asking these deep questions about Work and my readership just like Exploded and I started just having more And more conversations with people I had These weekly curiosity conversations and I actually just like recently paused Them but I had 383 of these over the Last five years about people's Relationship with work And what would happen over and over Again is people would tell me things and I'd be like Have you shared this with Anyone it's like well I've said like a
Little to my spouse but like I can't Talk about this with anyone So I was like oh wow what I'm writing About is like this hidden knowledge that Nobody feels like they can talk about Publicly Like I'm just gonna like lean into this Right more And then at the end of the year like I Had like three or four people that said To me Paul you have this like Broad range of ideas like where do I Start like can you just write a book Um and I had an interesting trade-off at the Time Thiago Forte was running a boot Camp with Billy Bros around like okay How to take your course to the next Level and I had this Consulting skills Course that was like really crushing it In 2020 Um because of remote work And I had a clear path like it was like Okay if I double down on that and go all In on this this year I could probably make a lot more money And I asked myself like what would I do If I made more money it was like oh I Would use that to get more free time to Write it was like oh why don't I just Write I'm in Taiwan for the year my cost Of living is lower Um I'm really drawn to like write about This stuff and I just committed to write
The book Early on I thought it would be just like I'll package some essays uh from my Newsletter and just ship it Um and then in the first three months I Really realized wow this is this is a Deeper like Um just self-reflection exercise of like Figuring out what this is all meant to Me And I knew there was something deeper to Say and I just sort of committed to The book and it I sort of had this sense Of like I know I can end up somewhere And I'll know when I'm heading towards That now and I know I can get there Um so I spent 13 months writing it and That was kind of the main priority for The entire year and Yeah it was a magical experience Actually Um The introduction when I read about like Why this stuff matters to me didn't come To me until like my final weeks in Taiwan And I was feeling so frustrated I went Out for a motorcycle ride And Like the ideas just came to me and I Just broke down in tears and I realized It had like everything to do with my Parents and like they didn't go to College they had to do the default path
And they felt like they sacrificed so Much so that like I could succeed And I realized like what they gave me Was like the freedom to dream And I for the first time this was like October so seven eight months ago Like finally felt like I can say this as a human like it Matters to like dream To like do Brave things to like Create And Yeah and I I think these things are Important and before that I didn't have the courage to say that Stuff I always couched my stuff or like Qualified it I was like you know what like I I really Think this matters and I think I can Help people with this stuff And I'm just gonna say it And so it was a really powerful Experience for me and I imagine you're going through something Similar like it's been really cool to Watch your journey too because I feel Like It's allowed you to understand your own Journey better too Hmm Yeah yeah the Journey of writing a book Is Jen is is interesting Um a lot of like
Windy turns along the way But I'm very happy with the direction That it's currently going and the plan Is today tomorrow and the day after bang Out a first draft of one of the chapters Each day Um nice so we'll we'll see what happens There Um yeah I was just kind of thinking as You were saying that that like your path Is almost Like it's it's weird when it comes to The Creator economy and kind of making a Living doing what you love on the side And all that all that stuff That a lot of people's paths seem to Follow the same general trajectory of I started making stuff That I liked in your case I started Writing about this job stuff and this Career stuff and I did that a bunch of Times and I realized I liked doing it And that it energized me so I kept on Continuing to do it and then along the Way people started to find out about it And then what you did was you had your Calendar link where for free anyone Could just book a call with you and you Would just talk to them completely for Free on the internet for like 383 times So through that you're speaking to People about this thing that you really Care about this thing that energizes you And then the next step is you're like
All right cool this is interesting let's Write a book about it and then you would Go and write a book about it and Self-publish the book and it's like Now your newsletter you know if you Wanted to get more and more lucrative Sponsors on it you could probably easily Do that like there's all these options That you now have for making money out Of this thing because you've now done it To the point where You were just following your curiosity You've been you know built an audience Now and and it's just like You know when people ask oh how do I Quit my job to become a Creator that's Literally the method it's like step one Yeah experiment with lots of things Figure out the one that energizes you do That repeatedly at some point you can Quit your job if you've got enough of a Financial safety net et cetera Etc And then just keep on doing that Repeatedly more people will find you and Then you will just figure out Opportunities along the way whether it's A book whether it's a course whether It's sponsorships whether it's Consulting gigs whether it's corporate Speaking for 100 grand for an hour of Speaking like there will there will be Stuff that comes up by virtue of the Fact that you are showing up there in The world and providing value I guess in
Inverted commas but in a way that Energizes you in a way that feels Somewhat effortless for you like even if You weren't making money you would Probably continue doing the writing Thing and so it's about finding finding Finding that thing like what is that Thing for for people listening if They're interested in for example Quitting their job or like doing the Creator thing or doing the business Thing And like I think it's it's the same with Startup Founders like the startup Founders that exit what do they do they They tend to take a few months off and Then they just start another company Because they just love it in theory uh Or maybe they're just chasing more and More but like you know mostly the people I've spoken to genuinely just enjoy Building companies and like oh great now I can start a new app And I think what we're all trying to do Is just get to that state where we can Be showing up and doing the things that Genuinely intrinsically motivate us Which as a side effect happen to make Enough money to sustain our our Lifestyle I think that's spot on I think the Opportunity and upshot of doing your own Thing is that you can lower the Percentage of things you're doing that
You sort of resent or like you feel like You're sacrificing Right in a job you may just have like Too many things And this was my case like it was just Doing too many things that I thought Were Silly pointless or just like Grueling to power through like I still Do some of those things it's just less So it means there's more space for that Creativity and curiosity to stay alive And that is really important to me And if it's important to you it's it's Possible and I think this is kind of What I was trying to get at and don't Find a niche Like find a mode of being in which you Can show up And like if you can find that I think like Ambition is really just like how fast You want to go at that point or like how Much like Leverage you want to implement Into your life I tend to like to go slower Um I find like super scale or super Large ambition pretty scary Um and maybe that will change over time But I have the mode so I have this like Deep faith that like I'm gonna be okay And I also just like my life And But to someone looking at my life on a Spreadsheet and trying to like
Do the math of like how life should be Live they'd be like how's this going to Work how are we going to afford a house Like I can't afford a house right now Is fine though because like that's not What I'm valuing right now and I feel Really good about my life and I don't Feel like I'm failing Do you feel like If and when you have kids that your Attitude towards this sort of stuff will Change I think So we want to have kids Um soon And I assume my perspective on a lot of Things will change in ways I can't Predict it Um However I think it will just Force me to be more like committed To like the things I'm doing I think I've like we've already started to think And talk about kids so like I do want to Be a parent and like a lot of what I've Been doing on this path has been Preparing myself to be a parent because I want to be a present engaged and a Live parent And that is just really important for me So like this kind of life gives me the Highest odds of doing that yeah But this is also why I've been like
Leaning into like okay maybe I should Like try to like monetize some of the Things I'm doing Because I also realize like when I do Have kids I am going to feel more Responsible and that's just gonna make Me braver at this point probably and Also people are going to want to root For me to succeed too So like there's going to be benefits too People sort of look at these things like What about kids like what they're doing Is like mapping their fears onto me Um I already have those fears I have all The fears on an uncertain path you Grapple with the fears every day But I can make choices and I feel really Good about having ownership of the Degrees of freedom I have And after five years I do see paths to Make money So like if that was my Prime aim and I Have confidence I probably could do it At this point Or I'll just apply for a job on your Team Yeah absolutely yeah welcome anytime Um Paul this has been absolutely Fantastic thank you so much for for Coming on the podcast uh where can People learn more about you And you're welcome uh so my newsletter Boundless.substack.com or website Think-boundless.com
Um a lot of the ideas we talked about Are better put in my book uh the pathos Path uh check it out Um pretty active on Twitter too Um love hearing from people's stories so Uh definitely reach out Amazing and yeah just wanted to say a Massive thank you to you as well for Like all of the stuff that you've Written uh in the book and in the Newsletter that's and and on Twitter as Well and in podcasts that has continued To inspire me over the last couple of Years as I've gone on to more of this uh Non-traditional more uncertain path than The very traditional one that I was on And yeah anyone listening to this if you Are considering breaking away from say Breaking away uh from a traditional path And you would like some advice on how to Pursue an uncertain one yeah check out All the pool stuff I was just looking Through my Kindle highlights on your Book and it's absolutely enormous and Yeah at some point I've been thinking I Need to get around to actually turning Turning a book into a book club video For my channel but it's just the Incredible like copious amount of Highlights I have for him just like damn It's okay this is going to be like a Whole like week-long project to just try And parse all the stuff figure out what Are the bits that most resonated with me
Because I find that when I'm when I'm Reading a book and I'm just enjoying all Of it highlight and then I'm like oh Damn highlighted like 80 of this book Damn that's kind of annoying I need to Go back through and progressively Summarize the highlights as some people Would recommend Awesome both continue to be inspired by Your journey too keep keep going man Thanks very much Um everyone Thanks for tuning in and We'll catch you later bye-bye alright so That's it for this week's episode of Deep dive thank you so much for watching Or listening all the links and resources That we mentioned in the podcast are Going to be linked down in the video Description or in the show notes Depending on where you're watching or Listening to this if you're listening to This on a podcast platform then do Please leave us a review on the iTunes Store it really helps other people Discover the podcast or if you're Watching this in full HD or 4k on YouTube then you can leave a comment Down below and ask any questions or any Insights or any thoughts about the Episode that would be awesome and if you Enjoyed this episode you might like to Check out this episode here as well Which links in with some of the stuff That we talked about in the episode so
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