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Hi, I'm Jim O'Shaughnessy and welcome to Infinite Loops.
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Sometimes we get caught up in what feel like infinite loops when trying to figure things out.
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Markets go up and down, research is presented and then refuted, and we find ourselves right back where we started.
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The goal of this podcast is to learn how we can reset our thinking on issues that hopefully leaves us with a better understanding as to why we think the way we think and how we might be able to change that to avoid going in infinite loops of thought.
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We hope to offer our listeners a fresh perspective on a variety of issues and look at them through a multifaceted lens — including history, philosophy, art, science, linguistics, and yes, also through quantitative analysis.
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And through these discussions help you not only become a better investor, but also become a more nuanced thinker.
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With each episode we hope to bring you along with us as we learn together.
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Thanks for joining us, now please enjoy this episode of Infinite Loops.
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Disclaimer: Jim O'Shaughnessy is chairman and Co-Chief Investment Officer of O'Shaughnessy Asset Management, where Jamie Catherwood is an associate.
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All opinions expressed by Jim, Jamie and podcast guests are solely their own opinions and do not reflect the opinions of O'Shaughnessy Asset Management.
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This podcast is for informational purposes only, and should not be relied upon as a basis for investment decisions.
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Clients of O'Shaughnessy Asset Management may maintain positions in the securities discussed in this podcast.
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Jim O'Shaughnessy: Well, hello everybody.
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It's Jim O'Shaughnessy with yet another Infinite Loops.
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Today's guest is Paul Millerd, the author of the Pathless Path, which I love you should buy his book. It's great.
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He's a freelance writer, an online creator.
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He is a pioneer in what I think the world is going to look like in maybe 10 years for a lot of people basically moving out of the obvious career paths to one that follows the pathless path. Welcome.
2:50
Paul Millerd: Thanks, Jim. Excited to dive in.
2:50
I think you've been thinking about a lot of these things much longer than I have and carving your own path too.
2:59
So excited to hear your stories as well.
2:59
Jim O'Shaughnessy: So it's really funny.
3:02
I was talking to my primary producer, I guess you'd call him director.
3:11
His name is Vatsal and I basically hired him just by watching him on Twitter for nine months, setting up his zoom, listening to him and the passion he had about his ideas.
3:18
And, so he's worked out fantastic for Infinite Loops.
3:25
It's why it's such a better show now because I'm a disaster as those things go.
3:30
But I was like, "Somebody's going to have to put a clock on me because I'm going to, I could talk to Paul for six hours."
3:37
Because essentially we are so simpatico on what we're thinking about, what we see emerging.
3:44
And so I just got almost giddy and my wife goes, "Okay, you're going to be talking to somebody who's like, loves Jed McKenna and Robert Anton Wilson."
4:00
And I'm like, "Well, yeah, maybe.
4:00
I have a couple of quotes that I just love.
4:06
So I want to ask you about a quote that you had that I kind of loved and really was quite witty, from my point of view, talking about, leaving a traditional career and really being a freelancer and taking the pathless path that you say, "I don't earn as much money as I used to, but now I have fun paying bills."
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Okay, you're the first person that I've ever met who's had fun paying bills.
4:32
Explain it to me, please?
4:32
Paul Millerd: I think what I was trying to say there is, there was an under-explored relationship with money that existed when I was in a pay payroll job.
4:46
Steady paycheck kind of comes in.
4:46
It was growing as I was progressing in my career.
4:54
And as soon as I left my job, the money went to zero and I suddenly had to panic and try to make money.
5:01
But as I was doing that, I sort of had to come face to face with, "Oh wow, you actually do care more about money than you thought."
5:07
It was just less than your former colleagues.
5:12
And you have this insecurity of running out of money that is probably human that you need to stare in the face.
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And I think the upshot of that was that I started to figure out what do I actually value, so when money becomes constrained after it was expanding, you suddenly start having to price your tradeoffs.
5:38
So I think I started to figure out, "Okay, what do I actually value?"
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And I've really gotten to a point now where I'm not as much tied to my former way of relating to money as that's too much.
5:51
That's not what it should cost.
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Now it's like, "Okay, this is the price, I'm going to pay that. I claim to value this.
5:56
I'm going to pay it and move on."
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Rather than dwelling on "Oh, this is not supposed to cost this."
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, which may or may not be a good thing to have during an inflationary environment.
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But I don't want to be playing accountant with my time and finite resources of energy on this sort of path. Jim O'Shaughnessy: Yeah.
6:26
I think that is an excellent point.
6:30
Francis Bacon's maxim that, "Money is a horrible master, but an excellent servant."
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I've met so many people and obviously I'm in asset management, so I'm exposed to this and people's views on money.
6:46
And it almost seems to me like it's the last taboo people don't want to talk about money at all.
6:54
And when we were still dealing with the end client, right?
6:54
So wealthy individuals for the most part, man, I mean, I felt like I was doing psychiatric therapy.
7:11
And I think one of the reasons for that is we sort of went from the tribe, right?
7:16
And the tribe, which we owed our allegiance to what Robert Wilson calls fun coupons, which is money.
7:22
And I love that and has a very different effect I think on the psyche.
7:32
Another thing that you've written that I totally believe and I've written extensively about, and I go on and on when allowed to, is this idea of the invisible scripts that are constraining our lives.
7:44
So I've done a lot of threads on this.
7:44
I've read a lot about it.
7:44
My friend, Tom Morgan, who's been on the podcast a couple of times, he calls it a tyranny of the fitness landscape and what you've done by essentially you progressed in your traditional job.
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And Tom would say that you got to a, kind of a high place in your fitness landscape.
8:12
And I think he would argue that it takes real guts to jump off that place.
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What are your thoughts about this?
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Paul Millerd: Yeah, it's a crazy thing to do.
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I tell people about my path.
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I think a lot of people reach out to me contemplating, should I quit my job?
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And what I tell them at a high level is it might really suck, but it might also be worth it.
8:33
And I think it gets down to what people, a lot smarter than me, like Joseph Campbell have written about, which is basically that you might need to burn down everything to find where you're meant to go.
8:45
And throughout history and a lot of smart people, you probably have other good quotes you could pull in here, but finding the path that you're meant to be on is one of these fundamental things were drawn towards in life.
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And I think, I would say there are certain type of person, which it took me a while to realize, but now it seems obvious that sort of needs an unconventional path.
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And I was constrained in a default script and path of life kind of convincing myself, "Oh, I can kind of remix this around the edges."
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And eventually I sort of had to stop lying to myself and the dissonance between what I claimed to care about and what my path was incentivizing me to care about was too large.
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And I sort of had to run away.
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So I don't see it as a courageous thing.
9:43
I sort of felt it in the moment of, I didn't really have any options left.
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And then I actually met Tom after listening to your episode and we talked about it and I think he had a similar thing, whereas he wasn't making this courageous leap.
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It was more like, "I don't have any option left.
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I need to go off and find something else."
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And this idea of getting lost, wandering into the unknown and grappling with uncertainty seemed so much better to me because I had this possibility of potentially finding something out that might lead me in a new direction. Jim O'Shaughnessy: Yeah.
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I agree with that assessment.
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I do think though that it does require almost at least from the lens I'm looking through, it requires a fairly high degree of self-awareness.
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And especially when you get to the point, as you just said that, "Oh, I don't think it was courageous.
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I looked at it as I didn't have a choice." Right.
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And I find that really interesting too, because a lot of the literature I'm trying to wake up psychologically, spiritually, et cetera, follows that same kind of death, birth, rebirth.
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But it also, to your point, a lot of the literature is death rebirth, but you don't proceed your regrets. And so that's scary too.
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Wilson calls it chapel perilous, and he says, when you go into chapel perilous, "Hey, good job for you bully for you.
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You got in the door now, be afraid, be very afraid."
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Is that how you looked at it?
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Did you look at it from a place of fear or did you look at it from a place of, "Well, I guess I'm jumping and let's see how I land." ?
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Paul Millerd: So I had gone through a health crisis right after business school.
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So I had been in the strategy consulting world, went to a good business school, graduated, started my job and sort of went downhill through unexplained symptoms, eventually figured it out, but had to take a leave of absence of four to five months from work.
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I was more or less just resting and laying in bed and feeling miserable and sinking into depression and really having to grapple with this tension of, I was so desperate, I need to resume my life.
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I need to get back to that career.
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And I realized what I was doing is, I was just grasping onto that successful identity.
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This idea of myself is like, " I am Paul the successful student, the person that goes to good schools and is in good jobs."
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And in my toughest moments there, I sort of realized that, "Okay, who am I really?"
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I'm a son, I'm people's cousin, I'm people's friends and none of that is actually dependent on what I'm doing.
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At least my closest friends.
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And my worst case scenario was being surrounded by family.
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And that sort of gave me courage to go forward from there.
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And also in a funny way, that non-work period where I wasn't getting paid and my savings was shrinking sort of gave me this I can be fine not working for a bit.
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One thing that surprised me though.
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And I think why my story has resonated is because I think I was sort of dumb about quitting my job.
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I honestly was just like, "I need to escape."
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And my surface level story was, "I'll just become a freelance consultant and I'll figure it out."
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What I quickly realized upon leaving my job was that the reality of being self-employed is totally different than just being out of work for a bit.
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And maybe the courage is deciding to stay on it that despite not feeling good in that first year.
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And in that first year, I was really grappling with, I wanted to escape work. I wanted to work less.
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I was really just trying to find more space in my life to figure things out.
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And it took me quite a while to realize that I didn't actually want to escape work.
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And this is sort of what the second half of my book is about is the real journey was finding work that matters, finding a path that matters, finding principles that really matter that I can stand up for test in the world and experiment with and continue going on those.
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But yeah, I didn't really know what I was doing and other people were like, "Aren't you worried about this, that?
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I was like, "No, I don't know. I'll be fine."
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I had this faith that I don't know, I'll figure it out.
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Worst case, I'll spend a year just wandering and I'll return to work.
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Jim O'Shaughnessy: Interesting.
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And, it's sort of, I have come to the conclusion, which is, I probably have to change as I learn and unlearn and relearn, but that once you kind of realize that we're all sort of confabulating hallucinators who are sort of hallucinating our life and what we want it to be like.
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And that leads to this idea, Jung said, "Until you understand you're unconscious events in your life will happen and you will call them fate."
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And I really loved that quote, which really got me thinking about, how do you get in touch with the unconscious, first there's your unconscious or subconscious, then there's the collective unconscious.
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I mean, which one, which one am I trying hook up with here?
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And I found that it's really interesting if you really do a lot of work around it and write about it a lot, trying to remove this duality between what we think of as Us, right, up here, at the prefrontal cortex, so to speak.
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And what we really are, which is that, these million apps running in the unconscious, and it also reminds me a little bit of what you were telling me about getting sick.
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There's a great book called The Body Keeps The Score.
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Paul Millerd: And yeah, I've read it.
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Jim O'Shaughnessy: Oh, have you. Okay.
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And then I'm also a huge fan of John Sarno who is an MD who really pioneered work in mind, body connections.
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And the first time you see it, you kind of, at least for me, it was kind of like, "That's bullshit, man."
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I read it and I threw it across the room and then I continued to read it.
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And by the seventh time I read it, I'm like, "I see myself out of a page of this."
16:52
So I sometimes wonder if those kind of events, right, it bleeds a little into be careful what you ask for, because if the universe is listening, it might make you the tool to attain that, but you might not like what it does to you. Right.
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So there's a great piece on Francis Ford Coppola and his near breakdown, trying to make Apocalypse Now, because it essentially, as, as Jed McKenna would say, the universe turned him into a tool that could make that movie.
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And I see that often in just far more quotidian events and people, and I think learning how to kind of align yourself with those messages, right.
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That are trying to come into the consciousness.
17:46
I think that that is time well served.
17:46
Is that something you worked on or thought about, or no?
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Paul Millerd: In business school, I wrote this leadership essay in my second year.
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And it was like, "Here are the principles I care about."
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It was like, "You should embrace humor in the workforce.
18:06
You should care about your junior colleagues.
18:12
You shouldn't put money above the things that mattered." All these principles.
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And I think the interesting thing is in business school, a lot of people are like this they're wired like this.
18:25
And I actually started, I pulled that out.
18:25
I kept coming back to that.
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I don't know why I came back to it, but eventually I created, I'm a former strategy consultant.
18:32
So I created a rubric and graded myself on a PowerPoint template.
18:37
And my numbers started going down and this was about six months before I left my job where it was just terrible scores.
18:48
And my whole background was studying organizational behavior.
18:59
And I kind of came to this aha, which was like, "Oh, of course my individual principles are not going to win out against certain organizational incentives."
19:12
And I was doing CEO succession planning at the time and was noticing that pretty much everyone, the system was creating the same type of people.
19:29
It didn't matter what their background was, but it was a very certain type of person.
19:29
And the system was selecting for those people.
19:37
You never actually arrive at a point where you start, oh, we'll flip on our principles.
19:46
Once we get to the leadership position, it doesn't really work that way.
19:51
Most of those people end up just leaving or self-selecting.
19:51
And I think the great thing now is we have an off-ramp now, which is really interesting, which is basically the internet.
20:03
You can come hang out with us first, right on Twitter discover, "Oh, wow, there's this whole playground of people exploring ideas."
20:10
And then you can sort of use that as your off ramp to find a more sustainable path. Jim O'Shaughnessy: Yeah.
20:20
I, again, very, very much, I think very much aligned with that.
20:20
And one of the things you touch on that I also sort of bang on is this idea of curiosity and like what you said earlier about the system selecting for certain traits.
20:39
You're absolutely right.
20:39
And I think one of the problems with education it's changing, thankfully, but the institutionalized education was essentially stripping you of any kind of rawness or edge that was sticking out and sort of making you into the person that they thought was going to be the success in the world.
21:06
And so sticking with curiosity for a minute, one of the things you've written also is, if you're going to be massively online, right.
21:23
Just at least try to not be 100% consumer right. Contribute something.
21:32
But I wonder when I kind look at the numbers, they seem to follow a Pareto Distribution pattern.
21:39
And so my question is, I know we're on a pathless path, but are there any sort of, my son wrote a great paper called Growth Without Goals.
21:54
Paul Millerd: Yeah, I like that one.
21:56
Jim O'Shaughnessy: Oh, thank you.
21:56
I'll tell him to listen to this, but if you were sitting with a young person and they were like, "I loved your book, I think it's fantastic.
22:08
I really want to pursue this curiosity." Right.
22:08
As Dorothy Parker said, "The cure for boredom is curiosity, and there is no cure for curiosity."
22:18
But how do you make, and this is something I've struggled with.
22:25
How do you make people who maybe are a little more conventionally minded, just that's their choice.
22:31
How do you stir up that curiosity so that you light the fire and the fire keeps burning?
22:40
Paul Millerd: Yeah, the first part is finding things that bring you alive, that excite you, that energize you. Right.
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I think for someone like you, that's probably a no brainer at this point. I think me too.
22:56
And then step two is using that as a guiding force.
22:56
So what I mean by that is if you're not drawn to do the things you know you care about something's wrong, right?
23:07
So then you need to just take a step back.
23:12
And that should be the analyze all options to reclaim that energy.
23:22
I think the more challenging thing is a large number of people don't have those things yet or at least have forgotten that state of mind of deep curiosity and energy, or just haven't explored that.
23:35
So one thing which has sort of been really cool to see is that I don't think people want my path.
23:45
I don't think people want to be fully, self-employed trying 15, 20 different kinds of work and trying to make it work month to month.
23:50
I love it, but it's not for everyone.
23:56
I think what most people do want though, is a one month break from worker mode.
24:01
They want a break from existing sort of like in the matrix. Right?
24:01
Of like, even if you're in a full-time job and you sort of like it, you're in this deep inertia routine, where it's hard to connect with yourself.
24:18
And over and over again, I've seen from people that take these one to three month breaks.
24:25
I was talking to a woman yesterday in New York.
24:30
And she used this phrase "forgotten hobbies".
24:30
And I see this so often it's, "Oh, I loved this as a kid.
24:42
I loved this as a teenager."
24:42
So personally, I've actually been trying to lean into this very purposely over the last year.
24:48
So, I've gotten really into yoyo again, learning how to yoyo.
24:48
I'm taking DJ lessons, because that was something I was dabbling with as a high schooler and colleger, and trying to really tap into that.
25:02
And when you find these things...
25:02
The thing I want to convey to people is this state is possible.
25:10
It's possible at all points in your lif. And it's worth finding.
25:19
So now, I know it exists, so I'm willing to fight to maintain this state.
25:19
And that doesn't mean I need to monetize all these things.
25:28
It means that this is an important part of my life and I need to figure out how to keep it going. Jim O'Shaughnessy: Yeah.
25:37
And you've written about DJing, which I thought was great, and how to write a book, and the various experiments that you're willing to take.
25:46
I started thinking about the DJ thing and I just... I always am seeking...
25:52
One half of myself is very empiricist oriented. Right?
25:52
So, I look for connections through everything.
26:02
One of the things I thought, when I thought about DJing...
26:06
And then, I started thinking about...
26:06
Are you familiar with the game Dungeons and Dragons?
26:13
Paul Millerd: Yeah, I haven't really played though. Jim O'Shaughnessy: Yeah. It's more about...
26:17
So, somebody my age, we played all the time in college, in the late seventies, early eighties.
26:24
But I started thinking about the fact that I was always the dungeon master.
26:29
And that's the person who creates the world.
26:29
And then, the other players play in it.
26:29
And so, one of the things I'm noticing as we're adding podcasts...
26:36
So, I think yours is going to be in the hundred and tens probably, when it gets released...
26:42
is I'm seeing this sort of emergence of a very strong theme.
26:49
Now, of course, I'm seeing that retrospectively, right?
26:49
And so, you always have to be careful about that.
26:56
But one of the rules, I think, of complex adaptive systems are top down solutions don't work in complex adaptive systems.
27:08
Bottom up is where emergence comes from. And I wondered like...
27:08
DJing, being the dungeon master, all of these things involve both creativity, but they also, in a way, involve world building. And it's my party. And here's your program. I hope you like it.
27:25
What do you think about that?
27:25
Do you think that there's an element of desire for...
27:30
not to control others, per se, but for self-control.
27:38
And then, also add on top of that, "Boy, I get a chance to entertain these people. I hope I'm good." Paul Millerd: Yeah.
27:49
It's I need to explore this.
27:49
I haven't made this connection.
27:54
And this is why I do these things, to try and uncover these connections, is...
27:58
I think one thing that's fascinating about DJing is my first lesson, I learned these fundamentals that basically opened up an entire new world and way of seeing music.
28:13
And it's this sort of portal to a different way of seeing the world. And it was so crazy.
28:13
I'd come back and I'm telling you what happened.
28:21
I'm like, "You have no idea.
28:21
There's these things called phrases in songs and like... oh wow."
28:24
And being able to take all these variables, I think, is something that is exciting to me.
28:33
I think what I'm doing with my writing and what I'm experimenting with my life is I'm sort of trying to uncover the fundamentals of carving a path, so that...
28:49
And I don't really prescribe a solution in my book.
28:49
It's more of "Here's a bunch of recipes I've tried.
28:57
And you can figure out where you fall on these." Right?
28:57
So, with money, there's a, never worry about it to completely worry about it.
29:04
But then, in the middle of that slider, there's all these interesting ways of reframing it.
29:10
And then, if you combine that with different ways of thinking about work, you can either have one full-time job or you can have 10 kinds of work, and be making all these small beds.
29:23
But there's ways along that.
29:23
And you start stacking all these different variables.
29:30
And you can basically create a one of one path for yourself.
29:36
And yeah, maybe there's an element there. I need to explore this.
29:44
I need to write about this to figure out what I really think though. Jim O'Shaughnessy: Yeah.
29:48
Well, that's another thing I do, and that I try to get people to understand.
29:51
I luckily got into that habit when I was 18.
29:57
And if you would see over here, there's just boxes and boxes of journals.
30:02
And one of the first things that I learned is that you really do need to write to see what you think. Paul Millerd: Yeah.
30:09
Jim O'Shaughnessy: Because I've had this happen to me so many times, right?
30:11
I know what I think about this. Pick up the pen. I got nothing.
30:19
And/or you write the thing down and you look at it, and you're like, "Well, that's bullshit. I don't believe that."
30:23
And I kind of think that it's the externalizing of that. Right?
30:23
And it's a bit like putting it into the world and putting it in writing has an effect on our nervous system and our brains.
30:42
And we interact with it differently than if we just let it stay as thoughts. So, one of the things...
30:50
You talk about true values, the true value of time and money. And I thought of...
30:58
I actually tweeted it while I was doing my homework for talking to you...
30:58
was the quote from John Dryden, which goes "Love and Time with reverence use, treat them as a parting friend, nor the golden gifts refuse, which in youth sincere they send.
31:16
For each year their price is more, and they less simple than before."
31:16
I like the sentiment about urging younger people because they have...
31:24
They're time billionaires. Right?
31:24
So, they have the most time, in terms of we're going to monetize it.
31:32
They can spend a lot on all of these things.
31:38
What I don't like about the quote though, is it seems to imply, "You know what?
31:43
If you miss out when you're young, each year they're less simple, each year their price is more." I kind of like...
31:50
I love the quote, but I really take issue with that last line.
31:56
I've seen a lot of people in their mid-seventies totally change.
32:02
Paul Millerd: I've talked to people like this too. Yeah. Jim O'Shaughnessy: Yeah.
32:05
And so, on the one hand, this is...
32:10
And as I thought about it, as I put it up, I sort of kind of think along your lines.
32:16
And I sort of think this is one of those invisible threats, right?
32:16
He didn't mean this to prescribe that, "Well, if you don't do it now, you're fucked.
32:24
When you're over 50, you're done." Paul Millerd: Right.
32:31
Jim O'Shaughnessy: And yet, we have so many of these messages.
32:37
And I don't think there's any kind of conspiracy here.
32:37
It's not like there are some dark Lords trying to manipulate the way that society turns out.
32:43
I think it happens because of human nature, because of the way we form society, because of all these things.
32:51
But I do think that this...
32:51
Well, retirement is another great example. Right?
33:00
You talk a lot about that.
33:00
And I think of the idea of retirement as a social construct. Right? Paul Millerd: Right.
33:11
Jim O'Shaughnessy: And one of the things that- Paul Millerd: A new one.
33:13
Jim O'Shaughnessy: A very new one, a very, very new one, much like...
33:14
And I want to get your...
33:14
I want to talk with you later a bit about where I see the world going.
33:20
From reading you, I think you...
33:20
Well, you're living it, so I know you think the world is going this way.
33:26
But going from the Bayesian distribution pattern, where everyone is focused on that 68, that meaty 68% in the middle of the bell curve, to a Mandelbrot distribution, which is like chaotic normal with really long tails and a really peaky middle.
33:45
But the idea of retirement, you're absolutely right, very brand new idea.
33:50
So, we kind of think of it as this thing that has been around forever. No, it hasn't. It's relatively rare.
33:58
But what I see then is this sort of chunking, right?
34:05
And then, it becomes a label.
34:05
And I'm generally opposed to label thinking of all kinds, because you miss the good stuff, in my opinion, of the tales. But it also...
34:19
It's kind of like retirement equals the end equals death.
34:19
And so, my grandfather never retired. He died when he was 88.
34:26
I'm never going to retire much to Patrick's conservation.
34:26
And so, tell me about that.
34:34
Tell me about how you think about these ideas of retirement and what lens you look at it through. Paul Millerd: Yeah.
34:43
So, I think, tying back to your previous point...
34:43
I think there's something people get wrong about what I'm saying.
34:50
And I think what they're doing is projecting.
34:50
I think I'm actually incredibly optimistic about how the world works.
34:55
These full-time jobs we have and the types of jobs and the amount of money people can make basically globally now, this is an incredible innovation, and leads to a certain amount of stability in the world, which is sort of unprecedented, not to mention the prosperity.
35:17
I think, however, I'm going to quote you, it was an anomaly that this could work indefinitely.
35:24
We sort of had this great boom after world war II where things were growing four to 5% a year, based on real organic growth.
35:32
That doesn't really exist anymore.
35:32
So, I think what's happening is that we have these scripts that sort of worked, which are how you're supposed to set up your life, but they don't actually map as much or as well to our current reality.
35:58
So, a lot of people are sort of doubling down on that same path because there isn't really a legible path or alternative.
36:07
My book is sort of a bold attempt at trying to come up with a story for not having the default path story.
36:16
But really, I want a hundred people to write books like mine.
36:23
And I think people like you have lived a story that is an alternative.
36:23
And it's incredible that people like you are sharing your wisdom and trying to guide along young people as well, because it's another like, "Oh, I see that.
36:34
I could try to follow something like that." Jim O'Shaughnessy: Yeah. Thank you.
36:45
My friend, Matt Clifford...
36:45
And I'm actually an investor in his company.
36:45
I had him on and he had this wonderful way of putting it.
36:51
He was like, "So, for most of history," he uses Napoleon as the example.
36:59
He was like, "Europe went through the Napoleonic wars and they're like fuck that.
36:59
We've got to give ambitious people a path. Right? Paul Millerd: Yeah. Right.
37:10
Jim O'Shaughnessy: And we have to...
37:10
Institutions were formed to dampen variance. Right?
37:10
And so, if you were a smart guy like you, you went to a certain business school, you downloaded certain principles, and you went into a certain prestigious organization, or if you were a consultant, or if you're going to be a banker, et cetera.
37:30
And now, we are living in a world, which I absolutely agree with your earlier statement.
37:35
We're living in a world where we have the largest variance amplifier in human history, the internet. Right?
37:39
But I couldn't agree with you more that like...
37:48
COVID sped this up, but a billion people suddenly came online, in terms of their ability to do, explore, to do all of these things.
37:56
And my staff and colleagues at Infinite Loops are a great example.
38:02
I've only met one of them in real life.
38:02
And yet, I know these people extraordinarily well. And I do.
38:10
I still do believe that you...
38:10
And when it's possible, I will do this.
38:15
But I believe that getting to know the other person in real life is very important because there are a lot of social cues, a lot of physical cues, et cetera, that we miss, even through screen.
38:31
But I mean, to me, that's really a smaller part.
38:31
The bigger part is that the people, my colleagues at Infinite Loops, got their positions because they had proof of work.
38:47
I didn't care what their C...
38:47
I didn't ask them for a CV. Right? Paul Millerd: Right. Yeah.
38:51
Nobody's asked for my resume in like three or four years.
38:53
Jim O'Shaughnessy: I don't have one.
38:56
But what I love now is that this is a much more common thing that people don't need to worry about CVs.
39:06
The gatekeepers are dying.
39:06
And why do you think they're all having these histrionic fits?
39:13
I mean, you don't have to be a genius to figure it out that they know they're dying and they're [inaudible].
39:19
Paul Millerd: Return to the office.
39:20
Jim O'Shaughnessy: Exactly, exactly.
39:22
And in my less kind moments, I'm saying, "You do know who wants to return to the office, don't you?"
39:30
And I always think of office space.
39:30
So, what would you say you do here?
39:41
Paul Millerd: Well, I think... Yeah.
39:41
I mean, organizations were great for dampening warlike urges and turning them into the desire to work on PowerPoint spreadsheets. Right?
39:52
However, in that dampening, there was a cost of inspiration and creativity.
40:03
And as organization scaled...
40:03
I'm sort of working on this idea.
40:03
I'm calling it too big to think. Jim O'Shaughnessy: Ooh. I love that. That is so true.
40:12
Paul Millerd: So, I'll test it out a little here.
40:12
So, you know Tom Peters, right? Jim O'Shaughnessy: Yeah.
40:18
Paul Millerd: So, Tom Peters, he was at McKinsey when it was like 500 people.
40:25
And he self describes himself as like a weirdo, just roaming around doing random stuff.
40:25
And he would be fired so quickly today by a company like McKinsey.
40:35
And McKinsey business schools, business journalism, or companies used to generate interesting ideas.
40:43
That is no longer the case, which means the cost of creativity is so high, except we have these off ramps like the internet, the problem being resumes actually work pretty good for signaling experience and credentials.
40:58
On the internet, you sort of have to create your own credibility from scratch, which is really hard, and actually incredibly hard, even for the McKinsey consultant. I've seen it.
41:12
I've seen my former colleagues try to dabble on the internet.
41:19
And they're like, "What do I do?
41:19
Why aren't people paying attention to my...
41:23
Why aren't people paying attention to all my nice credentials in my bio?
41:31
It's like, because no one cares about that. You need to show up. You need to do the work.
41:31
And you need to consistently show up, which is pretty hard and is going to lead to different types of behaviors of how people think about work.
41:42
But there's also enormous opportunity because these organizations are stifling us.
41:48
Ten percent of people would be way better off like me.
41:55
And this is the crazy thing I've experienced.
41:55
I was exploring complex adaptive systems and trying to push all these ideas.
42:00
And the organizations were like, "Ah, we do top down changes and these sell $10 million projects, so why would we introduce these principles?"
42:11
But then, I can just leave and write about that.
42:11
And the interested founders of companies are like, "Oh yes, this is cool.
42:17
Please talk to me right now." I was like, "Oh".
42:26
I was at BCG when, in 2015, I wrote this...
42:31
I basically wrote this report on transformation.
42:31
And at the end, I didn't even get my name on it. I wrote 80% of it.
42:38
They put five old male partners on the report. And I just...
42:38
I felt like, "What am I doing?
42:49
Why am I producing content for other people?"
42:49
And I think that sort of drove me to start writing online and wanting to just share my ideas directly.
42:58
And I'm just so grateful this environment and world exists.
43:04
And it's far better than my previous path for me.
43:12
Jim O'Shaughnessy: You know? Again, this is...
43:18
We got to find something we really disagree on because I totally, totally...
43:18
That resonates 100% with me.
43:25
I used to quip that the founders of America's greatest companies could never get a job there.
43:32
Paul Millerd: It's so true. Yeah. They're too radical.
43:37
Jim O'Shaughnessy: Way too radical.
43:40
Paul Millerd: Another cool story from consulting.
43:41
BCG, Bruce Henderson, five years into founding the company, decides...
43:48
He read this book about basically chaos theory.
43:48
And he's like, "All right.
43:48
We're going to divide our team into three different teams and we're all going to compete against each other. Craziest ideas win."
43:57
So, Bill Bain's working at the company at that time, re invents a whole new model of the business, and does a better version of a consulting firm.
44:08
And he's suddenly at war with Bruce Henderson. He is like, "All right. Screw you.
44:08
I'm leaving and starting my own firm."
44:14
None of these people are employable anymore, in today's world.
44:22
And I don't want us to go back to the 1960s or seventies because, for every like Bill Bain or Tom Peters, there were 10 other people that had no chance at all to express their creativity, which is why I think our current state is better.
44:35
We just need to wake up to the actual possibilities that exist.
44:39
Jim O'Shaughnessy: Totally agree.
44:42
And it's always been a fun exercise for me to think about those things because...
44:52
We're doing a series called The Great Reshuffle, all of these things that are kind of happening same time and got compressed because of COVID.
44:56
For example, geography exploding and no longer meaning anything, right?
45:03
That might have taken longer.
45:03
The work from anywhere... Now, let me be clear.
45:03
If your work is mental work or symbolic, whatever...
45:14
I'm not saying that people who are plumbers can work from home. Obviously, they can't.
45:22
However, I think that the options for people who are plumbers, who are electricians, who are landscapers are going to explode in the next year or the next 10 years, because there's so many people who are like, "Oh, I can do this over here on the internet."
45:39
And so, the idea that this is only going to benefit one class or type of person, I think, is erroneous. And I think that the...
45:49
I love the idea of being unemployable.
45:49
I often joke online that I am totally unemployable.
45:57
Paul Millerd: I'm getting there. Jim O'Shaughnessy: Yeah.
46:01
And it's a great place to be.
46:01
Because if you are totally unemployable, it means that- Paul Millerd: Burn the bridges.
46:09
Jim O'Shaughnessy: Yeah, exactly, exactly.
46:12
And that was kind of my strategy when I founded my first company, when I was 47. I was like...
46:17
My wife is saying, "So, what's plan B?"
46:17
And I'm like, "There is no plan B."
46:21
And I said, "You know what the conquistadors did, right."
46:21
And she's like, "Enlighten me, remind me."
46:27
And I said, "They got here and they burned their ships." Nope, Nope. Sorry guys. Your way home is done.
46:33
And so, a lot of people that I talk to though, they get that.
46:41
They understand, especially young people who are digital natives. Right?
46:47
And they're kind of like fish in the water, right? What's water?
46:47
These skills are just inherently downloaded into their human OS.
46:54
But there's also still this social thing that leads to fear of taking chances, that leads to fear that they're going to be shunned. Right?
47:09
And again, if you want to be evolutionist about it, well, of course there is. Right?
47:14
If we look at all the time that homo sapiens have been on this planet, most of it was we needed to fit into a tribe.
47:21
So, we had to be able to get along before standing up.
47:30
And now, that is still true to a certain extent.
47:30
But with the internet, with this variance amplifier, people don't necessarily have to either earn their living that way or be creative in the traditional way.
47:45
I just think of those profound philosophers that we call Pink Floyd.
47:51
And they were on this, how many? 30 years ago? With The Wall? And it's a brilliant...
47:59
One of my little quirks is, I think if you think about groups like Pink Floyd, certain songwriters, rappers, for example, a hundred years ago, they would've been poets or philosophy instructors at Oxbridge.
48:13
And so- Paul Millerd: Definitely.
48:17
Jim O'Shaughnessy: And so, we just moved it. Paul Millerd: Yes. I love that. Jim O'Shaughnessy: Yeah.
48:21
We just moved away from that.
48:21
And now, they're kind of doing their thing. And that's great.
48:25
I want to get back to this idea because I get asked this a lot.
48:25
And I think I love your thoughts on this.
48:31
So, this idea of enough, if you have enough, what you really have, that equals freedom. Right?
48:40
And if you don't, if you don't seek goals that are quantitative...
48:48
I need to have X amount of money and then I can retire.
48:48
I think that's a horrible sense.
48:53
I think that's a horrible way to think.
48:53
If you think though about, "Hey, freedom, love, family, integrity, creative ability to do what I like-" That's going to lead to a much better outcome. It's like happiness.
49:08
I've always thought of happiness as a byproduct.
49:08
Happiness isn't something that, "Oh, there's happiness.
49:13
I'm going to climb that mountain and at the top, I'm going to find happiness."
49:18
No, if you find happiness, guess where you're going to find it?
49:23
In the climb, in the doing, right?
49:23
But expand on this idea of enough equals freedom, because again, we're word thinkers for the most part, which is, I think often to our detriment, because words and phrases, at least in my experience, they can confine more than they can expand.
49:46
So, talk a little bit about how you got there. Paul Millerd: Yeah.
49:50
The default script most people grow up with in the world is, put your head down, study hard, get a good job.
49:57
And then question mark, but we're assuming that that produces a good life.
50:04
And it does work remarkably well for some people, but increasing numbers are saying they're unhappy with it.
50:14
Like you were saying, before retirement, there's a survey showing of US retired people that happiness or satisfaction with retirement has been declining for 20 years. Right?
50:27
So, people are not getting what they're expecting I am just taking this information and saying, "Okay, that doesn't seem like the best bet.
50:44
It just seems very risky to me.
50:44
Why not just try to aim at happiness directly?"
50:44
And by that, I don't mean aim at happiness directly, I mean, aim at trying to search for a state where I can like my life.
50:58
So, this ties back to thinking I wanted to escape work.
51:02
I don't think I wanted that.
51:02
I wanted to find work that mattered to me, that helped me connect with others, connect with myself, connect with the world.
51:08
And by doing that, I've stumbled into this principle I call, design for liking work, but really it's design for liking your life.
51:20
So, it's really a constant tinkering of saying, "Okay, did I like how I spent my week, my month, my year?
51:26
What should I remix around that?"
51:26
And we've anchored around a work day for thinking about our life.
51:34
People say, "What is your ideal work day?" That's crazy.
51:39
Jim O'Shaughnessy: I agree.
51:41
Paul Millerd: You should think about, what's your ideal work year, or what's your ideal life year or work month?
51:51
And it starts showing to you different habits.
51:51
I think we're more of these, like we might have a creative season and then we might need a season of rest.
52:02
And that's not compatible for most people with a traditional work life in today's world, especially the knowledge worker class, which is the hours of the work week have just been steadily going up while the rest of the economy has been going down.
52:24
Yeah, I think I went off on a tangent, but I think this is a tangent-friendly podcast, right?
52:35
Jim O'Shaughnessy: It's a very tangent-friendly podcast and I do weekly calls with Vatsal and he remarked at the end of one, he goes, "I actually write down notes, because you take such a circuitous path," and he goes, "but you always come back to the point."
52:56
Paul Millerd: Well, I can connect us to one previously.
53:02
So, I think we didn't actually answer the retirement question, but I think we're getting there.
53:06
Retirement, like you said, you don't want to retire, and that totally resonates with me now, but wouldn't resonate with so many people in today's world.
53:18
We have this idea that the retirement is the payoff for a hard work, a suffering.
53:24
We suffer and then we get the payoff and we get to rest in Florida.
53:31
One, I have kind of tested that.
53:31
I don't want to live in the beach, especially in Florida.
53:37
No offense to my parents who might listen to this, but I want to find the variables that I want to keep doing.
53:43
Now, may I ease back a little? Probably. Right?
53:50
My energy is definitely going to decline as I get older, but I want to find stuff I want to continue doing.
53:54
And that's my idea of retirement, which is basically just a continuation of what I'm doing now. So, why do I write?
54:01
Because I think I'll want to write the rest of my life.
54:07
Why do I help people and talk to a lot of people about their relationship with work?
54:11
Because mentoring's important to me, I think I want to continue that.
54:16
There's no age I want to turn that off. That's just who I am.
54:16
And by leaning into those, I can actually cultivate, what does it feel like and is it possible that I can do these things?
54:28
Instead of saying, "Okay, now I'm retired.
54:28
Now I need to figure out how I can get into the local university."
54:33
It's like, I don't know, that sounds like a lot of hard work.
54:40
Jim O'Shaughnessy: I love that distinction, because I would really trigger people that I was working with or mentoring, less so now than years ago, but I would often and do maintain that hard work does not equal success. Right?
54:53
That's a holdover from our days where physical labor was what you did. And guess what?
55:01
Yeah, the harder you worked, the better you did, the faster you built that house or shoed that horse or whatever.
55:16
But this idea and this kind of mythology, I think of as brutally toxic, like, life is pain, life is sorrow.
55:27
You've got to keep your nose to the grindstone. Are you kidding me?
55:36
Who wants to live in that world?
55:36
And then it's like, okay, you're going to suffer, suffer, suffer, suffer, and then maybe you'll get your five years as a reward. That's insane to me.
55:49
I mean, literally insane.
55:49
Paul Millerd: Well, I think at some point it was somewhat necessary, right?
55:53
It was like a cope for reality.
55:58
So, my parents didn't go to college.
55:58
My dad started working at Pratt & Whitney when he was 19 and worked on the factory floor.
56:04
So, hard work looked at working extra shifts and getting overtime.
56:11
For him, that was a no-brainer, because he could then create the conditions where I could thrive.
56:16
That was hard work, totally worth it.
56:23
I appreciated so much that, that sort of hard work happened.
56:28
We've shifted into a phase in which a vast majority of work are not that anymore. It's like creative work.
56:35
It's like moving information around, where we actually need more creativity and we need more ...
56:39
I mean, Naval writes about this as like, it's going to look more like athletes working working.
56:47
So, I think a lot of what I'd like to write about is exposing that, oh, these scripts exist. You grew up with them.
56:53
It was so reinforced in school and even in my first internship.
57:00
In school they tell you, "Hey, what do you think, you're just going to be able to go through life not doing stuff you don't want to do?"
57:11
Well, for the last five years of my life actually, I've sort of made it work.
57:15
I'm not becoming rich, but I have pulled it off.
57:20
My first internship, they're just making work for me.
57:20
And the older men were just so cynical and I didn't know any other possibilities, so I just eventually adapted to this mindset too, which is like, "What do you think, you're just going to get a job and not have to do stuff that's stupid or doesn't make sense?"
57:48
It's like, why are you saying this? Why?
57:48
So, I've always had this in me.
57:55
And I think it just took a long time for me to be like, okay, I've always felt this. It matters now.
58:05
The biggest transformation that's happened for me, and it happened through writing my book is, I'm just not ashamed to say that it matters to care about things anymore and it matters to find work that matters to you.
58:16
And it matters to aim at trying to find states that can put you in a better place for living your life.
58:23
Jim O'Shaughnessy: Again, we're going to be an echo chamber here, which I usually don't like, but you're so right.
58:33
I think about this a lot, I'm a quant, so I'm an empiricist.
58:33
I like to find formulas that work over a variety of environments and I can test what the worst case scenario is.
58:54
And I'm not going to look at a result, any single result and say, "Ooh, I did great.
58:54
My strategy was awesome." No, sorry.
59:04
You could have a horrible strategy with a great single result.
59:10
And if you think that way, you're going to go bankrupt, because what you need is to aggregate all results into base rates and then you say, "Well, yeah. Okay."
59:16
So, I've always thought that way.
59:21
And so, I've been trying to figure out, is it partially genetic?
59:30
Is it partially the way we're socialized as young people?
59:30
Tim Leary, who of course, poster child for psychedelics, but people forget that he was a tenured psychology professor at Harvard.
59:43
This was not a stupid doc.
59:43
Paul Millerd: Yeah, Ram Dass too.
59:46
Jim O'Shaughnessy: Yeah, exactly.
59:47
We're not talking about stupid people here.
59:47
And his whole thing was a bit depressing when you read about his theory about imprinting, right?
59:54
Because essentially what he says is, before you're three years old, the most fundamental and important imprints have happened, right?
1:00:06
So, you're either imprinted as a bottom dog or a top dog and you're either imprinted with a winner script or a loser script.
1:00:13
Now, obviously he wrote this a long time ago.
1:00:18
And one of the reasons why he was interested in psychedelic was, he thought that that was going to allow a form of meta reprogramming of these scripts, which I don't think is wrong necessarily.
1:00:29
I think we need to do a lot more research and see if it's true.
1:00:29
But I wondered, because whenever I see people react like this, when I say something like, hard work does not equal results anymore, what you need is smart work.
1:00:43
You need work that you need to work intelligently.
1:00:49
You need to be doing something that you really like and avoiding this hedonic treadmill.
1:00:56
You wrote about the whole social comparison and I've been on this hobby horse for a long time.
1:01:01
It's like, I went looking for hierarchies outside ...
1:01:01
So, first I started with all of human societies, right? There's got to be one.
1:01:07
I read that those hunter gatherer tribes in the Amazon, they don't have hierarchies.
1:01:13
Bullshit, they have incredible hierarchies.
1:01:13
Then I go down to the apes and then you go to ants and bees.
1:01:19
And you just keep scrolling down and you keep finding hierarchy.
1:01:25
And it's built into it, seemingly, any social creature's system.
1:01:25
I had no idea, and I'd read about this in a book, that we get the term, the pecking order, from chicken hierarchies.
1:01:39
Paul Millerd: Makes sense.
1:01:41
Jim O'Shaughnessy: A guy, a creative, right?
1:01:41
A creative was sitting on his dad's chicken farm in the '30s and looking and saying, "I wonder if there's a hierarchy in chickens?"
1:01:49
So, he went to the neighbor, got a hen, which who was a foreign hen and tossed that hen in with the other ones. A blood fest. Paul Millerd: Wow.
1:02:03
Jim O'Shaughnessy: Thus, the pecking order, right?
1:02:05
They had to reestablish where they were in terms.
1:02:05
And the hen that sat at the top, she was pecked the fewest times.
1:02:11
The poor hen that sat at the bottom sometimes died when you introduced this new character.
1:02:18
So, I always try to think, well, how do I put myself in flow with the way things are? I may not like that.
1:02:26
I might not like that we act like this, but if I can position myself in the flow of, I guess, we call it the universe, [inaudible] that kind of thing, I'm going to get better outcomes.
1:02:39
But I think it leads me to another thing with you, you seem to be a natural tinkerer, right? Paul Millerd: Yeah.
1:02:47
Jim O'Shaughnessy: And you seem to be quite happy with like, "I'm fine if I tinker with this and it doesn't work, I'll learn something." Paul Millerd: Yeah.
1:02:55
Jim O'Shaughnessy: Again, I struggle, because I'm usually devoted towards, how can I make this outcome better for people or this person I'm working with? Or whatever.
1:03:03
And I know I can anticipate your answer, but I want to hear you say it, is there some kind of underlying set of mindsets or mental models that if a person could truly download them, that would lead to their willingness to be more of a tinkerer, more of an experimenter, more of a person who's like, "You know what?
1:03:36
It might not work, but I'm going to learn something from it anyway." Or no?
1:03:43
Paul Millerd: So, I think yes, based on ...
1:03:43
So, I do these Curiosity Conversations every Wednesday.
1:03:48
I've probably talked to three to 400 people from 40-plus countries, all sorts of backgrounds, socioeconomic status.
1:03:55
So, there's a couple things.
1:04:04
I think, yes, based on what I've heard from people taking breaks from worker mode.
1:04:04
So, there's this default worker mode, which you don't actually have to be in work, you just have to be in the flow of the current economic paradigm you're in.
1:04:16
So, that could be a work week or anything like that.
1:04:22
So, if you're able to create some space from that, often people are just pulled towards stuff in natural ways.
1:04:27
And when you're pulled towards something, you don't even think of it as tinkering.
1:04:31
Like my wife has found she's so pulled to art and she was saying the other day, "It feels like I have to paint and experiment and do these things."
1:04:47
And she's trying to figure out, how do I design more of her life around that? Right?
1:04:47
Because it's so easy for her.
1:04:52
And it looks like hard work to other people, but it's actually easy.
1:04:59
And then the other thing is, what I've realized through these conversations is that one, on my previous path, I was around a very narrow type of human, which is this hyper-analytical, systemic thinking, Western mind.
1:05:12
From my Curiosity Conversations, it's blown open my, "Oh wow, humans..."
1:05:20
And this is so obvious, right? Humans are so diverse. And personality types.
1:05:30
And I start seeing all the different settings on the bars, like financial insecurity, basically, I don't think it has any correlation to how much money you have.
1:05:39
I'm talking to somebody who has like 100 grand in college debt, and he's 22 and he's like, "I'm not going to work in a traditional job. I'll be fine.
1:05:47
Just tell me how to carve my own path." Right?
1:05:53
And then I talk to the Google employee who has $3 million in the bank, he tells me, and he's like, "What if I can't get a job after six months?"
1:06:00
I was like, "Well, you can live forever pretty much anywhere."
1:06:06
But he doesn't experience that.
1:06:06
So, I think there's two things, right?
1:06:06
It's like, one is, you got to figure out what your actual traits are. How are you wired?
1:06:15
For me, this current path is great for me.
1:06:23
The uncertainty of not knowing how I'll be making money six months from now is super exciting to me.
1:06:29
It's like, "Oh, what will I come up with?"
1:06:39
At first, it was really hard because I hadn't experienced it, but I really enjoy it. It cracks me up.
1:06:46
But I can't give you that natural tendency towards that.
1:06:46
But I've lost that tinkering spirit. I had to rediscover it.
1:06:58
And I wasn't this hyper-curious kid, reading books on my own and stuff.
1:07:04
I had to reawaken this child-like identity.
1:07:04
Like the DJing, even when you learn something like DJing, you feel so stupid, because learning is feeling stupid.
1:07:14
Real learning is feeling stupid.
1:07:24
I started learning Chinese, and if you want to feel stupid, that is the best language to learn. Jim O'Shaughnessy: Yeah.
1:07:32
Paul Millerd: But you have to start to see wisdom in that.
1:07:34
And you actually can, by practicing this tinkering mode.
1:07:34
But I don't know, I think there are people that are drawn, they just want to keep the trains on time.
1:07:44
And that it's great that those people exist, but we live in an age where the upsides to tinkering are higher than ever.
1:07:49
So, it's at least worth trying to experiment with.
1:07:54
Jim O'Shaughnessy: Again. Yes, absolutely. Totally agree.
1:07:59
And I love that last line, because that is what I'm so excited about.
1:08:10
I said to my wife last night, "Damn it, I wish I was born in 1980 instead of 1960." She's like, "Why?"
1:08:16
I went, "The cool stuff that-" Paul Millerd: I know exactly what you mean. Jim O'Shaughnessy: Yeah.
1:08:20
"The cool stuff that is coming online now, it's just going to go exponential.
1:08:20
I just want to be here and watch it just because it's so cool."
1:08:26
Paul Millerd: Well question for you.
1:08:30
You've probably talked about that.
1:08:30
I've listened to a bunch of your podcasts, but not all of them.
1:08:34
This is why I admire you, how did you deal with being a weirdo without Twitter and the online friends and all this?
1:08:50
That must have been so hard.
1:08:50
Jim O'Shaughnessy: Actually, it's interesting.
1:08:52
No, it really wasn't, because again, I think that I, like my son Patrick says, "I ruin every sample I'm included in."
1:09:01
And like, "You're such a weirdo, dad."
1:09:10
But the fact is, I was like that when I was a kid.
1:09:10
So, I naturally go toward ...
1:09:10
People just get so tired of me, because I just keep saying, "Why, why, why?
1:09:21
Well, why do you think that?"
1:09:27
But I think that I lucked out, honestly, I was very lucky. And I was helpful.
1:09:36
And then also, people wanted to know things, they came to me, because I figured stuff out.
1:09:45
And people think I'm joking on Twitter when I say I'm lazy. It's very true. I'm incredibly lazy.
1:09:52
I love to figure things out and I like to figure out the easiest way to do something.
1:09:52
And so, I was like that as a kid, too.
1:09:59
So again, useful, because kids would come to me and they'd say, "Well, how do you do these perfect Latin translations?"
1:10:06
I went, "I don't do them.
1:10:06
I go down to the James J.
1:10:11
Hill Library where they have all of these books translated."
1:10:11
And they're like, "Fucking O'Shaughnessy, man."
1:10:16
Paul Millerd: Well, this is interesting.
1:10:18
I think I'm pretty lazy too, but I'm always looking for the efficient way to do things, because I didn't like doing things that I didn't want to do.
1:10:32
So, someone was asking me about suffering, and I think the kind of suffering that destroys people is when you're spending 50-plus percent of your time doing things you absolutely don't want to be doing.
1:10:45
So, always in my jobs, I was always trying to lower that amount.
1:10:45
And on my current path, I'm able to get that close to zero because I'm able to define control all the variables, but that's what makes people resent their path.
1:11:00
Or what they're doing is, doing these large buckets of time they don't want to do, like writing my book on the outside looking in, looks like, oh my gosh, that looks so painful or hard. I really liked it.
1:11:20
There was always a part which like, wow, this is so hard, but so good.
1:11:30
And I worked very long hours on it, but at no point did I ever want to run away or escape it.
1:11:41
And I think that's what I always keep coming back to is, if you can't stand doing work you don't want to be doing, the path forward is to embrace that laziness as you might call it and find the work that matters to you, that will get done no matter what.
1:12:01
And maybe this podcast is this for you.
1:12:01
Like, if you stop doing it might be more painful than if you kept going.
1:12:08
Jim O'Shaughnessy: Yeah, I mean, potentially that's an interesting insight.
1:12:10
I've never looked at it that way.
1:12:14
So thank you, I'm going to consider that for a bit because the funny thing is, I got talked into doing this podcast by Jamie Catherwood, Right?
1:12:21
So, Jamie was like there's just no beating the guy who never quits. Right?
1:12:27
And so Jamie wanted to work for us and he originally contacted Patrick and just send him an email, not telling Patrick that Jamie was in Washington DC.
1:12:42
And he shot Patrick an email several years ago and he is like, "Hey, I'd love to get lunch with you if that's ever a possibility" and Patrick was feeling benevolent, I guess, or feeling exploratory.
1:12:56
And he saw this email and he like, "Oh, that's interesting. I know this kid.
1:13:02
I don't remember where I know, oh, he might be an analyst on one of our phones".
1:13:06
And so Patrick just kind of immediately responded, "Yeah, sure. How about tomorrow?"
1:13:10
And Jamie was like, "Tomorrow's great".
1:13:10
So Jamie woke up at 5:00 AM, drove to Connecticut and have lunch.
1:13:17
And so that continued, right?
1:13:17
Because we didn't hire him right away. We wanted to watch him.
1:13:24
And so Jamie was the other one who basically got his job through Twitter because I watched him and I watched the way he thought, and I thought it was good.
1:13:29
So anyway, he immediately starts bugging me.
1:13:35
He's like, "You got to do a podcast now, you've got to do a podcast".
1:13:39
I'm like, "I don't even listen to podcast Jamie, why would I? No, I'm not doing.
1:13:44
And also cause that's Patrick's stuff".
1:13:44
And he goes, "Yeah, his podcasts are awesome, but yours could be just about whatever you want them to be about".
1:13:55
And so I put all of the workload on Jamie.
1:13:55
I'm like, "Okay, I'll do it.
1:14:01
But here's what you got to do beforehand".
1:14:01
But I love that thought because I think you're probably right.
1:14:07
This is an indulgence for me. I'm very lucky.
1:14:07
I'm very, very lucky to be able to get really super interesting people like you, to have conversations with me.
1:14:21
And it's like, I love it because I get to learn all sorts of different things and get different perspectives.
1:14:26
Like now, I'm going to spend probably the rest of the day thinking about, "I wonder if Paul's right.
1:14:31
I wonder if this is like...
1:14:31
If I stop the podcast, whether that would be more painful", but I love that way of looking at it because people can look at other things that way too. Right?
1:14:42
If you look at it and you've written a lot about inversion too, and that's Charlie Munger.
1:14:47
And so I was going to ask you about it and it's kind of like, ah, everybody talks about it, invert, always invert and I'm like, okay.
1:15:01
Because I agree, I think it's a great mental model, but even the term mental model, I [inaudible] heard that now. Paul Millerd: Yeah.
1:15:08
Jim O'Shaughnessy: Cause everybody's using it.
1:15:08
And so I think foundational thinking, latticework of things that to hang ideas on and everything else, but when it gets overdone, it's just like, yeah, been there, done that, don't want to talk about it.
1:15:26
But again, I have, which I think you can really appreciate because you do too.
1:15:33
I have the luxury of doing what I want to do. Paul Millerd: Yeah.
1:15:38
Jim O'Shaughnessy: And other people, like I can almost always tell when, where somebody's at in their frame of mind, like, "Well, of course it's easy for you to say it, [inaudible]" And I really want to sometimes shake that person, say, "Well, how the fuck do you think I got here?
1:15:58
It wasn't because I was just always spitting in people's eyes.
1:15:58
It was because I was useful too."
1:16:03
Paul Millerd: So it's so true, yeah.
1:16:03
I mean, you could just use me as the example, like I've made an average of 30 to 50 grand for the last five years and I would describe my life as thriving. Jim O'Shaughnessy: Yep.
1:16:20
Paul Millerd: I don't have a path to...
1:16:20
But people still say this to me, they're like, "Oh, you can do what you're doing because you have this degree or something". And it's like, maybe.
1:16:30
Like some of the skills I learned in those environments, super valuable, yes.
1:16:37
But it was actually harder starting from those worlds because I had so much unlearning and relearning, I had to do.
1:16:44
Like learning how to write on the internet and share my ideas.
1:16:50
I'm still not all that great, I have so much opportunity to continue to grow.
1:16:59
But the thing is, from talking to people is like, anyone actually curious about taking an unconventional path doesn't care what your background is.
1:17:04
All they want to do is...
1:17:10
All I care about is how can I download wisdom from Jim? Because...
1:17:14
And I think this is why it's so amazing that you did start a podcast, is like knowing that people like you exist is so inspiring.
1:17:21
Like for me, there are so many cynical, older men and there are almost like all that exists in the corporate world.
1:17:28
And the biggest thing that's driving me is, I didn't want to be that, I didn't want to wind up this cynical, dunking on everything, shitting on everything, being negative about, "Oh, wait till you're my age". It's like...
1:17:48
And Seth Godin was a huge inspiration for me because he was an older man that still felt alive.
1:17:54
And it was like, just knowing these people exist.
1:17:54
It's like, "Wow, it's great".
1:17:54
And then listen to your podcast is like you're so excited about ideas.
1:17:59
And it's like, "Yes, I can be that at that age too". Right?
1:18:06
You're like in your early fifties or something. Right?
1:18:10
Jim O'Shaughnessy: Well, thank you.
1:18:10
Early sixties, I appreciate the decade not there.
1:18:14
Paul Millerd: But yeah, I think this is also what I'm trying to show too, is like I sort of went on this shift from cynicism to optimism and what I...
1:18:23
I've said this already, I think is this state of being engaged with your life is possible.
1:18:32
Many people have reached it throughout history.
1:18:39
They're all screaming from the rooftops once they've reached it, that it's possible.
1:18:44
And your starting conditions, like you need a certain amount of security and a good starting position for sure and there's a lot of opportunity to improve that.
1:18:57
But more people than ever before in the world have this within their reach, like we're talking billions of people.
1:19:05
Jim O'Shaughnessy: 100% and that's what makes me so excited.
1:19:07
I'm so excited by where the world is unfolding too.
1:19:07
And always people say, "Well, are you just going to be paint glossy about the whole thing?"
1:19:17
I'm like, "Absolutely not".
1:19:21
I think what we're going to create is better and better problems.
1:19:21
We're going to create a lot of problems. Paul Millerd: Oh yeah.
1:19:28
Jim O'Shaughnessy: And that's what error correction is for. Right?
1:19:28
And this idea of cynicism and pessimism, people think it makes them sound smart.
1:19:35
I don't think that at all, I think it makes you sound conventional and dumb and you got to break through to be willing to reframe things as to "Wow, that really sucked.
1:19:50
But I learned this from that". Paul Millerd: Yeah.
1:19:53
Jim O'Shaughnessy: And that's what I always aimed for, was this continual growth. Right?
1:19:54
And if you're going to grow continually, you've got to unlearn a bunch of shit.
1:20:01
You've got to unlearn things that used to work and no longer work for a variety of reasons.
1:20:07
Some of them good, some of them bad. Right?
1:20:07
And into these kind of chaotic environments, these exponential changes, these abundance mindsets as opposed to negative-sum games, play positive-sum games because you can now. Right?
1:20:25
And it wasn't possible if...
1:20:25
I always do these alternate histories and I'm dead in all of them, like if I would've been a horrible peasant in France, in the 14th century, because- Paul Millerd: Me too, right?
1:20:36
I would've been thrown out with you.
1:20:39
Jim O'Shaughnessy: Me too.
1:20:41
It's like, probably I would've been out on the drive.
1:20:41
It's like, no, you're gone, which of course means you're dead.
1:20:46
And so like this, I'm just so passionate about finding people and helping people see that this is possible in the world.
1:20:54
And it's just so cool and where we are...
1:21:05
Another thing that I just... Ameri...
1:21:05
I was born in 1960, when I was born, basically it was illegal for a person of color to marry a white person in half the states.
1:21:13
My oldest sister married a black in 1971.
1:21:19
Their marriage was illegal in half of the states in the United States. Paul Millerd: Crazy.
1:21:29
Jim O'Shaughnessy: How crazy is that? How crazy?
1:21:29
Paul Millerd: I think marrying...
1:21:32
Like my wife's Taiwanese, I think that was illegal in several states.
1:21:32
I was looking at this 50 years ago.
1:21:39
It was like, we wouldn't have been able to get married in the states.
1:21:42
Jim O'Shaughnessy: Crazy.
1:21:44
And all of these old social models, which frankly I mean, from our perspective, from where we sit now, they sucked.
1:21:52
Like in 1971, when I was 11, a woman couldn't get a credit card unless her card has a note from her husband.
1:21:59
And so when people talk to me about, "Oh, we're so regressive and so backwards".
1:22:06
I'm like, "Are you crazy?"
1:22:14
No other country has made the strides that America has made because mostly open society, rule of law, willingness to be able to listen to the critics, error correction.
1:22:27
You can't have error correction if people are silenced, you can only have error correction, when there's a whole heap of people saying this is wrong. Right?
1:22:32
And you think of Martin Luther king Jr, you think of the heroes of the civil rights movement. They were brave.
1:22:39
They took great risks, but it actually works now, does that mean that all of those problems are gone?
1:22:44
Of course not, but it means that we get to start from a higher place to start to improve more. Right?
1:22:51
Will my great, great grandchildren look back and say, "Oh my God, my great, great grandfather was such a monster. He ate actual animals"? Maybe. Paul Millerd: Yeah.
1:23:07
Jim O'Shaughnessy: I mean, honestly.
1:23:08
Paul Millerd: We probably won't be able to predict what the thing is.
1:23:13
Jim O'Shaughnessy: Right, exactly. And so rather than...
1:23:13
We live in a probabilistic world and we've got to get comfortable with that but you can also reflect on what we were just talking about.
1:23:27
We have made such progress from, on so many fronts, in terms of color, in terms of sexuality, in terms of what is now acceptable in polite society, that term itself sounds an antiquated to me.
1:23:45
Paul Millerd: I think one of the other things I've learned is that the biggest benefits of these shifts are mostly non-Americans and non-Western countries.
1:23:55
Jim O'Shaughnessy: Very [inaudible].
1:23:58
Paul Millerd: The high wage full-time jobs are actually sort of a trap.
1:24:05
I'd say the majority of people I've talked to, in my curiosity conversations have been like X, United States, and then about half of those have been like X, Western, like X industrialized, Western countries.
1:24:17
And I talked to these people and they're so excited about the future.
1:24:22
I have a Indonesian friend in Taiwan and he basically went from a job paying like 5,000 a year to like 60,000 a year through basically his optimism, tapping into the internet and learning how to engage with ideas and just reaching out to a remote company.
1:24:46
It's like, he's made himself rich, 60 grand living in Taiwan is like you've got it made.
1:24:56
Jim O'Shaughnessy: Which I think and honestly, this is my mindset, obviously it's going to create blind spots for me, I realize that, but I love hearing those stories. Paul Millerd: Yeah.
1:25:09
Jim O'Shaughnessy: We invested in...
1:25:10
I don't know whether you'd know Dan McMurtrie, SuperMugatu on Twitter.
1:25:10
So I got to know him before really getting to know him on Twitter because we both were in New York and really interesting guy, really thoughtful.
1:25:21
And so when he approached me to invest in this venture fund that he was setting up in Bangladesh, it's called Anchorless Bangladesh, I was so intrigued because I'm confirming your insights of dealing with the other people, the people that I talk to and listen to are so ridiculously optimistic because their world is finally opening up.
1:25:42
And I've never seen a group of people more committed to...
1:25:53
Like, are you kidding me?
1:26:00
Usually five years ago, this was impossible.
1:26:00
If you wanted, you had to go one of the 12 dominant families of Bangladesh and they expected a huge dividend in the first quarter. Right? Paul Millerd: Right.
1:26:12
Jim O'Shaughnessy: And so I completely agree with you.
1:26:12
And so, one of the reasons why I'm a huge fan of travel, I've been on every continent except Antarctica and the more you travel, the more you interact with people who don't share your cultural background, the more open your eyes become too, there are a lot of different ways to look at the world.
1:26:36
Some of them are better than others, yeah but to echo your theme, the other thing that I've found is you've got to find what resonates for you.
1:26:43
You got to find what's right for you.
1:26:43
My way might be totally wrong for you.
1:26:49
Your way might be totally wrong for other people.
1:26:54
But if you're lighting that match and you're getting them to get curious, to get inspired, to start looking, I mean, to me, right there, that's a well looked because if you...
1:27:03
Because to me, I'm going back now to my concept of usefulness. Right?
1:27:10
That's useful, in my opinion.
1:27:10
And that's why I loved your book.
1:27:18
That's why I wanted to have you on for a conversation.
1:27:18
And Jamie again, my school mom, I only glance at the time and I see that, I'm like, "Okay, you got to wrap up here".
1:27:32
So before I ask you the final question, like what's next?
1:27:32
What right now, are you enjoying or doing that a year ago you would've been, if you told you yourself of a year ago " Oh, by the way, nearing May 1st, 2022, you're going to be really in deep love with X", you would've said no way, anything that's really different?
1:27:59
Paul Millerd: So the what's next question is really weird.
1:28:02
I sort of associate that question with my previous path of what's the next step?
1:28:09
Jim O'Shaughnessy: Ah, I hate that term, but okay, that's fair.
1:28:12
Paul Millerd: So I sort of just want to stay in the slipstream I've been in, I really like it.
1:28:15
And I'm trying to look for clues that I'm out of that slipstream and continue staying in it, which will lead me to do interesting things I think.
1:28:29
I think a year ago, I was really nervous about moving back to the US.
1:28:29
Me and my wife were living in Taiwan for all of 2021.
1:28:36
And she just got her green card and we moved back in October.
1:28:44
And about a year ago, I was telling her, like really nervous about where are we live?
1:28:52
I feel like the US is still pretty cynical.
1:28:52
I was scared of losing some of my gains, I think.
1:29:03
And through the book, I sort of...
1:29:03
The second half of the book is really like a personal transfer, like throughout the book, as I wrote it, I basically became happier and found peace with my path, which is a really weird experience.
1:29:18
But I think the optimism would've surprised me, I think too, I mean, Austin, like I didn't know I'd be in Austin, but I'm really loving it here.
1:29:31
There's a lot of people that...
1:29:31
The best way I'd describe it is like, there's a majority of people here who are just like what they're doing or really excited about what they're doing, which is really energizing to be around for both me and my wife, who are both exploring the things that bring us alive.
1:29:49
My book's done way better than I expected.
1:29:57
And I'm really just trying to enjoy the day to day.
1:29:57
So I don't know what's next, I just feel so grateful and happy and blessed with what I have right now and just want to continue to keep it going.
1:30:15
Jim O'Shaughnessy: So amen to that. That is such a... I have found in...
1:30:16
I have the pleasure and honor of meeting lots of really interesting people in the world.
1:30:24
And that is one of the underlying outlooks that shines through.
1:30:32
So many of the people that are just like...
1:30:32
I'll give you an example.
1:30:32
The photographer, Joel Meyerowitz is a friend, he's considered the greatest living street photographer in the world. And he's what? 83 now.
1:30:44
We went to Berlin for his 80th birthday.
1:30:44
Joel has the face of a young teenager.
1:30:53
He's got all the wrinkles and everything, but the light in his eyes...
1:30:59
Paul Millerd: I love that. Jim O'Shaughnessy: ...
1:30:59
It's just that thing that I love.
1:30:59
I love interacting with him because everything is, "Have you seen this, Jim?
1:31:02
Look at how cool this is. Look at this image".
1:31:08
And it's just being around people like that, just supercharges your energy. And so it's kind of...
1:31:14
The way I kind of look at it is, it's a selfish act on my part, honestly, to surround myself with people like that because it makes me feel so good and that's okay, call me selfish, I want to feel good.
1:31:27
And one of the ways that I feel good is surrounded by people like Joel and people like you and having the ability to talk and interact with them.
1:31:33
So I couldn't agree more on that. Who knows what's next? We'll see.
1:31:39
So that leads me to our final question and- Paul Millerd: I did not prepare for this, but I know it's coming.
1:31:49
Jim O'Shaughnessy: What's really funny is very few people do, which I really love.
1:31:51
And that really, I love that.
1:31:51
So I ask at the end of all of these, we're going to wave a wand and make you the emperor of the world.
1:32:04
You can't be the anti-authoritarian that I am, you can't imprison anyone, you can't execute anyone.
1:32:11
But what you can do is incept them.
1:32:11
You can whisper into a magical microphone, two things, and everybody in the entire world is going to wake up the next day thinking it's their idea, and they're going to go, "Huh? I love that.
1:32:24
I'm going to start doing that".
1:32:31
Now, what two things are you going to say?
1:32:31
Paul Millerd: I think one of them would be that there's this state of non-doing and there's something worth finding out in that state.
1:32:51
Jim O'Shaughnessy: Will we not doing [inaudible] activity? I love it.
1:32:55
Paul Millerd: And I think the second one would be, this is sort of Eric Fromm's idea, is that love is a practice.
1:33:09
And I think his book art of loving is so powerful because he sort of offers an antidote to cynicism, which he says that there's many ways to engage, find love in the world, ones through creative activity, ones through practicing true generosity.
1:33:22
But it all comes back to like this is a practice, this is not something you can actually have.
1:33:28
Jim O'Shaughnessy: Yeah, I love that notion, that's great.
1:33:31
Wow, those are two good ones.
1:33:31
Those are two excellent ones.
1:33:38
Well, listen, this has been absolutely delightful and I think we'll probably do it again.
1:33:46
I'm delighted that your book is doing better and you certainly have my endorsement. You sent me a copy.
1:33:52
It's a great book, I read it.
1:33:52
I had fun going back to my notes.
1:33:58
I recommend everyone out there, who's...
1:33:58
You might even be happy with your career, even if you are, read this book, because what it'll do is just start asking questions maybe and Paul did it and guess what?
1:34:09
He got happier and happier with it.
1:34:09
And I highly recommend that reading it makes you happy too.
1:34:17
So Paul, thank you so much for being on, enjoyed it.
1:34:17
And it seems like you are definitely in the slipstream of the flow of the universe and I love it.
1:34:31
Paul Millerd: Thanks, Jim.