Michael Ashcroft on Getting Lost and The Joys of Dad Life
- 0:00 – Introduction / Teaser
- 1:38 – Introduction and Missing Guest
- 2:28 – Podcast Plans and Initial Banter
- 2:49 – Reflecting on Past Conversations
- 3:37 – The Journey of Self-Employment
- 12:12 – Life Updates and Health Challenges
- 16:04 – Parenting Reflections and Future Plans
- 19:38 – Balancing Work and Family Life
- 23:58 – Navigating Challenges and Personal Growth
- 30:02 – The Role of Fathers and Emotional Resilience
- 33:35 – The Impact of Miscarriages and Moving Forward
- 36:46 – Reflecting on a Challenging Project
- 38:16 – Book Sales and Audience Insights
- 39:57 – Future Plans and Creative Inspiration
- 40:51 – The State of Online Creation
- 50:20 – AI and Its Impact on Creativity
- 1:00:04 – Balancing Work, Family, and Creativity
- 1:05:25 – Fun and Games: Dictator or Hustle Bro?
- 1:08:25 – Concluding Thoughts and Future Outlook
Transcript
I chat with Michael on parenting, getting lost, the pathless path, hustle culture, travel, and more. This is his 4th appearance on the show.
Read the full transcript
Paul: Who said this, Dictator or Hustle Bro? The goal of every struggle is victory. It's almost indistinguishable from how many people in the hustle world communicate these days. Like, you got to struggle in your 20s for payoff in your 30s and It's humans love this shit. You can ride this language to wealth or power, and I don't know how to defeat it, but it works. I am recording an end of year 2025 reflection with Michael Ashcroft and Johnny Miller, who has not showed up to the call.
And he's, he's the one without kids. So me and Michael are having a hard time with this. And so if he joins, we're going to be missing him. But the goal was— Johnny and Michael are two people— we've been in like a group chat for like 2 years now, and we've had many conversations over the years. I've gotten to know both of you really well. We're like kindred spirits on these journeys as like, um, inverse hustle bros.
And so like trying to be successful without aiming at success. And so Yeah, was planning on doing a roundup of life updates, work updates, path updates, reflections on the year, and then a fun game I was going to do. Who said it? Dictator or Hustle Bro? We'll see. We'll see if we get to that.
So I had you on the podcast. We had like a flurry of podcasts where we had a grand ambitious plan. And my plan was, okay, here's somebody who knows he's going to quit, having all this success and we'll do 6 months before, we'll record one on the— I think we recorded on the week you quit and then we did 6 months after.
Michael Ashcroft: Yeah.
Paul: And then we failed to ever record another episode. And so— I mean, 3 is not bad. Yeah, that was pretty good. But I always had it in the back of my head. I'm like, ah, we should do an update episode, kind of like check in. So that was what, 4 years ago?
5 years ago. When did you leave your job?
Michael Ashcroft: I left my job in January 2021, so it's been coming up on 5 years since the middle of the podcast, I would say.
Paul: And so I said to you during that time that you were skipping a step in being successful and you were already crushing it with your online course. And you were telling me before the podcast that I was telling you, you needed to, you can't skip the phase of wandering throughout the through the wilderness with and getting lost.
Michael Ashcroft: Exactly. I mean, cuz your whole story has been like, I quit to nothing and went traveling and did nothing for years and that was really, really important. And I came in going like, yeah, I've got this online course and it's doing well. I'm just gonna skip that step. And I distinctly remember you telling me something like, nah, man, I think it's my interpretation of this anyway, was that you've been, you're too successful too quickly. You're gonna have to.
Like something is up here. And I interpreted that as like, you have to get lost for a while. And I was not having it. And given how things unfolded, I think you were, you were right. Or at least my view of what you said was right, because I had to get lost. And the last few years kind of captured that.
Paul: What was I right about, I wonder? Like, what do you mean you had to get lost? What does that mean?
Michael Ashcroft: I think I was going from the work environment into self-employment with the same kind of mindset of working, if not grinding, but still working basically.
Paul: And it's consistent work.
Michael Ashcroft: It's like I, I gave myself a little break, but it was more like, oh, I'm building a business now, and that's what we're doing, and that's what the work is. And in the absence of the external work environment, the structures, the bosses, the deadlines, it just didn't work. I couldn't, I couldn't make myself work, and I think my, my system rebelled. So what ended up happening was we had a, like, a 9 months after I quit, and I bought some things, business kept going, it was great. Then we went traveling for a year, Mexico, Bali, all that kind of stuff, which was amazing. But it's not like I was working particularly hard.
It was, I was making enough money to pay all the bills and keep traveling, and that was great. And then I came back and that's when I said it seemed like I needed the, no, we're just gonna like do nothing for a while, enforced stuff along with health issues and other stuff. But like it was still a kind of very quiet, not particularly high achieving period of my life.
Paul: Yeah. What was the story around like having to build a business at the beginning?
Michael Ashcroft: I think the story was that the business let me escape the life I was living. And I kind of substituted, oh, I was doing that and now I, now I'm doing this. It's like the identity had to shift, um, from employee to business owner or something like that. Um, except it just wasn't sustainable. Um, I, I, I think that that's why the getting lost phase was important because the identity had to dissolve rather than just transfer to a new object. If that makes sense.
Paul: Yeah, it's really— I bet a lot of people who know about your path and work would be pretty surprised by this. I mean, you had been telling me, we had always had calls over the years, but you still were like selling courses. You were engaging in writing and engaging with people. And I think a lot of people see the product of work, especially when you're an online creator and doing things like this, it sort of seems like you were doing a lot, but I guess behind the scenes it sort of felt like maybe declining motivation. And one thing I always say on these paths is you go from— at a job you can do 5 out of 10 inspired work, like if you're 5 out of 10 of wanting to do it. Yeah, the emotional coercion of wanting to please your colleagues and just being a generally decent human, you're going to complete the work.
But that 5 out of 10 work or even 6 or 7 out of 10 work on your own starts to become so painful to do. Not like painful to do, but just like, man, you have to whip up so much energy, especially if you're like shifting between different kinds of work. Does that resonate?
Michael Ashcroft: It, it really does. I mean, the, the kind of forcey energy where you just have to meet the client deadline, you have to not let your colleagues down, you have to whatever it— when you're working for yourself, you're just letting yourself down. And I think most of us, uh, find that much easier than letting down someone else. And I didn't wanna keep grinding or grinding's the wrong word, but it's almost like there was a part of me that knew that the shape of work I was creating from that place wasn't the right shape. And I didn't want to create from that place. I actually had this hilarious story where I pre-launched a course in 2021 called Playful Creativity because I was in a role and it's like, how to be creative.
I think I bought this. Yeah, I'm sure. And then I refunded you and the other 77 people who bought it because I found myself trying to make it sitting in this room in Oaxaca in this ethically grindy headspace. I'm like, I cannot in good conscience make Conscience make a product called Playful Creativity that I made through grinding. And that, that's like, uh, that encapsulates the entire like period where like I don't want to make from this place and I have the spaciousness and resources to wait a while. Let's just be a potato and see what happens, basically, with plenty of like shaming and, you know, judgment along with it.
But that's also part of the process.
Paul: I think you really should have just shipped a set of videos of you dancing in Oaxacan weddings for Like 30 days straight. Yeah.
Michael Ashcroft: That would be before the giant hats and—
Paul: Yeah, that would've been like playful creativity. Yeah, I totally understand that. I often talk about going slower or doing less and sort of have this joking refrain of, have you tried doing less on the problem?
Michael Ashcroft: Right.
Paul: And I think, I think it's getting to what you're talking about because you could have done the course, but you then would've created. Another thing you had to maintenance. It's not just passive income. And even if it was, you would feel like disappointed if you didn't keep updating it or creating it. And so you were making the decision of like, I don't want to embody this state for longer than I'm doing it now, even though by letting go, you then go through this cycle of like, I'm an idiot, I'm missing out on opportunities, all these things.
Michael Ashcroft: Yeah, it makes me feel that it's the, the threefold view of doing, not doing, and non-doing, almost. So if doing is grinding and non-doing is doing something with just the perfect amount of energy that doesn't feel effortful at all, the other option is not doing. So I didn't want to grind, I didn't have access to the, the elegant flow of non-doing, so the best option was not doing anything, I think, which is still a more wise outcome than grinding in, in the context I was in, I think.
Paul: Yeah, and so you, you moved back to London. I, I still just wonder what would have happened if you just stayed in a place longer than a couple months and didn't move back to London.
Michael Ashcroft: Well, it's because we came back, we actually had tickets onwards to Cape Town, um, but the, the container for the, the one year that we had was Cecile's, um, one-year sabbatical from her job. So she was on a formal sabbatical and had a job to go back to after a year. So we were like We got tickets to Cape Town because it just felt like a place we could go, but the option was her getting the job back, and we opted for the job. So she did that for a full year and then decided to quit, uh, for other reasons. But that's, that's what kind of prompted us coming back. Um, and I don't think that going on to Cape Town for 3 months and then doing 3 months in new places is the right fit for us.
Um, the best time we had was in Bali for 6 months because we had such a long time there, but we both realize that we're not really nomads, or if we are nomads, then we're like 2 or 3 years in one place, not like 6 months or 3 months in one place, like nomads. But yeah, London is expensive and hustly, and all the things that I enjoyed leaving are still here and still affect psychology.
Paul: Yeah, that, that makes a lot of sense. So what is going on this year?
Michael Ashcroft: This year coming up? 2025, like, ah, the review, of course. Well, I have a baby. That's the big news. I have a baby. Uh, it's great.
I love having a baby. Uh, he is coming up on 9 months old. Uh, so most of this year has been either baby or third trimester of pregnancy shaped, uh, getting ready for baby. So that's been incredible, and I'm really happy that it came out this way. And the other big thing is that, uh, I've had this lifelong knee issue, like, since I was 10, it first manifested. And I had an injury in August that made me basically afraid to walk, um, culminated quite badly and just being terrified of walking.
And that's one thing when you don't have a child, but when you have a baby, recognizing that unless you do something, it's dangerous to carry your child, um, and fast forwarding not being able to run around, play with him, lift him on my shoulders, that kind of thing was just, um, not acceptable anymore. So I finally managed to find a surgeon who could fix my pretty complex issue, um, and had a big surgery 10 weeks ago now, and I'll have another one on the other knee in February. So this year has really been family and health, uh, quite strongly.
Paul: Yeah, that is pretty intense.
Michael Ashcroft: Yeah.
Paul: What, um, yeah, that's gonna be huge for when your kid starts running. I have an almost 3-year-old now and man, they have so much energy.
Michael Ashcroft: Well, that was the idea to get this all done before he starts running around too much. Um, and ideally, like, he will never remember me having bad knees because by the time he remembers stuff, I'll be fine. That's the, that's the goal here.
Paul: Awesome. Uh, well, not awesome. It's pretty painful. I mean, you were, you were sending us the, the images of your, of your leg and the change and all the downtime is, and that's pretty intense. I mean, it also seems like this period has forced you into getting lost, even if you can't move and sort of like reflecting on what you want. Has it been helpful to like figure out what you want to do moving forward?
Michael Ashcroft: I think so. Um, but what it's really given me is it keeps surfacing the, like, latent grindy energy that is still there. So I had this story of like, okay, 2 or 3 weeks post-surgery, I will just be on the couch, but then I can start reading and writing, can't I? Surely. And then it took like 7 weeks until my brain worked and I wasn't exhausted. Um, so it just made me confront those parts of me again, going like, oh no, I'm still I still have that, like, I should be doing something energy, um, but I think the enforced rest has helped me to figure out what I'm teaching much more clearly, and I've been able to immerse much more in study and, and education.
So I'm definitely grateful. I'm, I'm glad that things didn't work out for me before because then I'd have gone a different path, and I think the path I'm about to embark on is much better.
Paul: Yeah. Do you wanna share the, the phrase you're using or do you wanna keep that quiet for now?
Michael Ashcroft: Uh, let's keep it quiet for now. I think it's something, something good for me. I like it.
Paul: I like it. It's gonna be great.
Michael Ashcroft: Thank you. Well, when I shared it with you and Johnny, you were just like, yes, that good. And I really appreciated that. So thank you.
Paul: Yeah. There are certain things that just sort of work. I think book titles work like this in the sense of it's either correct or it's like, ah, maybe, or it just flows into your brain and it works. I think you've landed on something like that.
Michael Ashcroft: Cool. How's your year been, Paul?
Paul: Yeah, yeah. I realize I turned into like podcaster bro and I started just interrogating you. My year's been interesting. I think we ended the year in Austin and it was a really intense year. Of, I don't even know. Yeah, I launched my book, second book, Good Work, after 7, 8 months of pretty like focused, disciplined writing, which was very different than my previous style of write when it feels right, like follow the flow.
And so I was writing with child. I finished the book. I did a couple events. And then I went into lead dad mode as Angie started her book. So Angie took over using the majority of the workdays for her, and I was just basically filling in all the gaps, doing a lot of the mornings, a lot of the nights. And, uh, I was then working like 2 days a week, kind of.
Um, and so I love the period of dad mode. And I think I've been playing with this idea of quantity over quality. And it was just the day in, day out trips to the park with Michelle, like wandering around with her doing just— I mean, we didn't accomplish anything of impressiveness, but just going on bike rides dozens of times over and over again, going on walks, playing in the house. I think it really, like, I really became a dad this year. Like, being a guy with a wife who's pregnant is really weird. At least it was for me.
Like, nothing is happening to you. Meanwhile, your spouse is going through this transformative experience. Like, truly magical. Growing a baby inside of them and you're just like there. And then I think I really loved the early stages, but looking back, I think it was much more just about like absolutely loving the, the physical contact, the connection, the cuddling, the like reactions they have, all the small things. And it was kind of like me opening up and like softening into myself, like loosening up.
But then I think like from year 1 or about what you're about to embark on now until 2 years, I spent so much time with her and developed this really cool connection with her. I was like, she never really had like a mommy phase. Like it was always a She often had a daddy phase even, and always just liked both of us. And so it was just so cool. And I think through the quantity of just so many days, so many hours, I think I sort of like, there's no blur between my different identities anymore, if that makes sense. I'm just like a dad now and then doing stuff around that.
And it's given me a lot more confidence to really prioritize my wife and daughter and think about that a lot more seriously. And so that's been cool. But then we moved to Asia at the beginning of this year, and we've been getting a lot of help from Angie's dad in particular and her mom as well. And I did not know how much I had lost track of like my own identity, my relationship to Angie, and my connection to work. And so I had really sort of lost all of that and I found it again. And now it's really cool that like, I honestly feel like it took me like 3 whole years to like play with all the pieces, spend the intensive time, get time away, and like now see like, okay, now I see how this can all fit together.
And yeah, we're trying to have another kid, so like, that's just gonna like reset the clock, but hopefully some of the learnings carry over.
Michael Ashcroft: That's amazing. I'm, I'm really happy you've had such an enjoyable journey, and I'm curious now how things will start to change. The second baby will of course affect this, but like, how are the entities going forwards, do you think? Are you, are you finding work yourself again? Or is it like his dad firmly entrenched now?
Paul: I think the cool thing was, like we were saying at the beginning, I went through 5 years of wandering in the wilderness and really pressure testing what I actually cared about with reality, which was writing being a core activity. And then, I mean, all the success I've had with The Pathless Path is I just feel so lucky that that's coincided in the last 3 years, has really taken the pressure off. To worry about money in the short term. And so the hardest thing for me was actually reconnecting with the more playful side of work. I think in writing Good Work, I love the writing, but I sort of burned out myself through working in that way because I was not doing enough of the like random tweeting, exploring rabbit holes, going vibe code, like learning how to vibe code for a few weeks. And I think all of those random things are actually an essential part of my journey.
So over this past year, I've really been trying to lean into those things. We were also in Oaxaca for a month at the beginning of the year, and I decided I would just learn how to vibe code and play with that and have fun. And that was so great in terms of unlocking all this energy. I wrote a bunch of interesting stuff around that, so I started to see the relationship of those things. But it's still hard, I think. We're trying to figure out the balance of what makes sense of me to work, Angie to work.
Angie just finished her book. I mean, she's wrapping it up now and she's really come to terms with she does not like working with other people or in institutions, right? Given the choice of being in mom mode. And so she's really grown into the role of being a mother. And I think leveling up her nervous system to being able to thrive, or at least lean more into that. So I think she's thinking of leaning more into that.
And also it's just like the practical tradeoffs of, okay, Paul does seem more interested than Angie in making money, which is not hard because she's like a 1 out of 100 interested. So even, even if I'm like 20 out of 100 interested, I'm 20 times more excited to like potentially make money than that. And so yeah, we're still trying to figure that out. I think the right amount of work when you're a parent is not zero and the right amount of work is not 100, but I'm using work very loosely. Like work could be personal growth or fitness. It could be like martial arts, dancing.
All sorts of things. And it's more about like, how do we connect with ourself? How do we connect with our work? How do we connect in the relationship and how do we connect to our daughter and balancing all those things? I don't think it's meant to be easy. I was joking with somebody who was a bit lost with work today, and I was just reflecting that— don't— I mean, I do feel lost at times with work, but I don't really have like any sort of meaning issues.
I, I just have a child and like that provides plenty of material.
Michael Ashcroft: Yeah, I've had the same experience honestly, that I'm so grateful that I get to be around so much for the first, well, potentially years of his life. Um, I hear stories of dads who have short paternity leave, which in the UK is like 2 months is pretty short, um, but 2 weeks, um, some cases long for the US. Yeah. And, and it's just, I, I'm just grateful that I don't have to do the whole like commute, work, come home, do bath time. And that's the extent that I get with my child for 5 days a week. And I, I'm sacrificing a huge amount of income right now by being self-employed and, you know, doing it this way.
But I'm not gonna get these years again and he's not going to be like this again. And I'm really, really loving the fact that I can make the trade of nervous system and his attachment and health and all that stuff in exchange for a couple of years of reduced income. Uh, fine, completely fine. No, no hang-ups about that at all. I will have to make more money because I want to provide a great family life for him and give him opportunity to do some of the stuff that money brings. But right now this is the optimal solution, I think, for my situation.
Paul: What's your mental accounting on that? Mine is sort of like, okay, if I break even with making enough money to cover my cost of living, that is success. And even still, since I made so much in 2023, I can even lose a bit, which I did last year. I spent more than I made. So that, that's fine cuz I'm sort of like mentally carrying over some of the excess profit, but I do find people do need some sort of story. What do you have something like that or what are your discussions like around it?
Michael Ashcroft: Yeah, so I think I'm more in the red than you are because expensive place and big surgeries and that kind of thing. So I am, I am dipping into savings more than I want to be. Um, my mental accounting of this though is almost seeing as a kind of investment in, in our collective future. So on the one hand, having knees where I'm not afraid to fall over will pay dividends, uh, for the rest of my life. It's just enormous. And it's not every single step I take might, you know, won't result in the most pain I've ever felt in my life by random chance.
Like, that's how it has been since I was 10. That's huge. I'll invest in that. That's great. And then, like I said, being around my, my son when he's like 1, 2, 3 years old, I can't conceive of the benefits of that, but I think they're enormous. Like, I, I wonder if, you know, 10 years from now, if someone said, hey, there are these issues, how much would you pay to go away?
I suspect that number will be way, way, way more, um, than the amount I'm losing now. And I think many of those issues are being removed by being so present and well-regulated and giving him a great environment. Now, that's just a guess. It's a hunch. I have no studies to back this up, but it just feels right, and that's the way I want to be doing.
Paul: I think it's even the selfish gains in the moment. I've just become so much more playful and silly and loose and able to laugh at myself and It's like you just wait. One-year-olds, as soon as they start walking and talking, they start making fun of you. They want to dance everywhere. And so I've just decided if my daughter wants to dance, I'm dancing. And this is not something people do in Taiwan right now.
So I'm often putting myself in uncomfortable situations, but it's just so fun. And yeah, I think, I don't think you need the story of like, I'm doing it for the kid because I think there can be a trap in that. I don't think you are putting the burden on him, but I think I see a lot of parents doing things like, oh, I need to do this, or they have this story, I need to do this otherwise there'll be so much suffering. And I know kids are so resilient. They're just so much tougher than us. Like, they really flow and adjust and adapt and survive.
And it's— I'm always trying to pair giving the most I can, but also just thinking, okay, if I had 4 kids, I'd probably be a little more chill, right? And the kid probably would be fine.
Michael Ashcroft: Absolutely. And I, I agree with you that this is as much for me. Like, I love being able to do a couple of hours work right now in our bedroom because small place in London, and then like go out into the living area and he smiles and sees me, we play for 20 minutes, and then like, it's so great. And I guess you're right, I— it's not just that it's for him and his future, but I don't want to miss this. I don't want to—
Paul: it's very fun.
Michael Ashcroft: It's so quick as well, like seeing, seeing the changes in his development, like, over the course of days, you suddenly realize there's a new baby, and you could blink and miss a phase. And I love that I witnessed the entire unfoldment of his— of who he is, and I know all his temperaments and his tastes and what he's like. And there's no— like, Cecilia isn't telling me, oh, he did this today, and oh, this is what he likes. I know what he likes. I know what he did. I was there.
It's great. Um, so maybe, yeah, selfishness is the way, but I'm, I'm taking the selfish path if that's what it is.
Paul: Yeah. It's such a, I mean, you don't need all the spiritual retreats or modalities either. Like having a kid is enough triggering and challenges to grow too. It's, I feel like somebody just needs to, yeah, some, you should just create an online course where it's like the path to enlightenment and like step one is like have a baby.
Michael Ashcroft: Right. Yeah, it's also a shame we haven't got the nervous system expert here, but I'm sure that there's so much nervous system value in like needing to be regulated for the baby. It's like, you are crying, I'm the one you're getting the regulation from, I have to like calm myself very quickly and not mention about me and how difficult my life is because you're the one crying and you're the one who needs me right now. And it's very grounding to have that responsibility at the same time. Like it makes it easier to look after myself.
Paul: It's like a video game though, because it gets a lot harder and more challenging. At this age, my daughter knows how to use crying to get what she wants.
Michael Ashcroft: Ah, okay.
Paul: And she knows how to, she started negotiating. And if we reacted to every cry with just seeking to soothe her, I don't think she would sleep. I don't think she would ever eat anything except chocolate.
Michael Ashcroft: Good taste.
Paul: And so, I mean, there are schools of thought to just let it rip and do that, but I don't see— it feels pretty natural to like be creating boundaries and be a guide and You can sort of tell like when they're in the middle of the night, if she's screaming, I know the kind of cry I need to go dress versus the one where she'll cry for like 30 seconds and then just roll over and go back to sleep. It's, yeah. And those are the things you learn in just spending so much time. You've heard all the range of cries and types of cries and yeah, just get, man, it's wild. Our daughter's so— yeah, she has so many, um, ideas and preferences and negotiate.
Michael Ashcroft: And yeah, I'm quite looking forward to getting to do more fathering because up till now it's been like mothering slash parenting. Um, with the older he gets, the more that I feel the father role becomes available and useful, um, as opposed to just like general parenting roles or mothering roles. Um, it's starting to happen, uh, and I can see it being quite fun, I think. And that's why I think the boundary setting and the exploration and all that kind of stuff, it gets more, uh, risk-taking gets more relevant, I think.
Paul: Yeah, I think for us it took Angie's nervous system longer to adapt to the crying and the needs and her freaking out. This could just be our baseline settings, whereas like I think I was able to adjust and adapt earlier. So I was— I became like the, the relief support. If things got too intense, I could like step in and relieve things and sort of absorb the stress of mom and baby at the same time. And so I think, um, yeah, I think, I think there is this role for the father of like shock absorber sometimes. And the failure mode of that is becoming a permanent shock absorber and never feeling what you're feeling.
But yeah, that's— I mean, that's been a big challenge. I, I, we had a really tough stretch over the last, I think, year. And yeah, about a year ago, Angie had her first miscarriage. She's talked about this. Uh, and then 5 months later she had a second miscarriage. And all through that we were moving out of Austin and she was getting citizenship.
Our appointment was getting canceled. We didn't have a place to live. It was very intense. And that period was really intense on me. I had some people I could talk to, but I probably didn't do a good enough job of really feeling what was going on. But in that moment, it, that period, it was just like, okay, I need to be like the stability here for our daughter, for Angie.
And yeah, it's, it's very intense, but it definitely made us stronger too. I think it's been a lot easier to make decisions about what we're doing, why we're doing it, thinking about our roles and things like that moving forward.
Michael Ashcroft: Yeah. And I think you're absolutely right about the, uh, shock absorber being a really important role as well. Um, as long as you don't get stuck there. So if the life context is just such that you need lots of shock absorbing, then you're gonna have to do it, uh, as long as you can come out of it afterwards. Maybe— I mean, I, I talk a lot about feeling your feelings, but sometimes if you gotta get something done in the short term, maybe it's best that you don't for that couple of days, and then you can deal with it afterwards if that means you can get the thing done. Just don't get stuck there, like you say.
Paul: Yeah, it's been really weird. I mean, most of what I do is not directly tied to earning any money. Now, I mean, I sell books when I share ideas and people become aware of them, but for a lot of it, things are spreading in itself. And so for the last few years, I mean, this has been my whole journey. When I'm working, I'm not directly generating income. So every time I'm deciding to work, it's been a lot of overhead, I think, just to always just be managing these trade-offs.
When should I go home early? Should I keep working and doing these things? I think what has helped me is just committing to a schedule on a seasonal basis and saying, especially now since I launched this premium hardcover, saying, okay, by the way, and everyone should get one.
Michael Ashcroft: It's a very good product. I love it. I'm so happy you made it. It's the best thing on my bookshelf. Get the book.
Paul: Thank you. Yeah, that means a lot. You and Johnny were so helpful when I was panic texting in the weeks and months leading up to the launch and reassuring me because I shared it with several people, sort of when I was testing the pre-launch and got a lot of feedback like, oh, I would never pay $100 for a book. And I'm just like, oh my God, what have I done? I'm pretty sure I texted you guys like, I think I'm gonna sell like 15, maybe 50. Like, it's okay.
I'll just like write it off in my head. It's a branding exercise. But it was so great. Like, even if that did happen, it was really great to have the encouragement of people like you and Johnny saying like, no, this actually is just great. In and of itself, and it's awesome that it exists. So I really appreciated that because, yeah, that was a really challenging, uh, that was challenging few weeks for me.
I think that was the most intense feelings of failure I was feeling, and I really had to work through a lot of money emotions, scripts I had about what I should be doing. Because I changed my entire approach to my path for this project. Before, it was spend as little as possible, test before you launch, make everything profitable from the beginning. This one was do it secretly, uh, do it over 12 months, invest $80,000, bet on a completely new way of launching a product, ship it, physically around the world from a single warehouse and somebody you're just starting to work with, and then still commit to your launch strategy of just doing like posts and tweets and sharing it with people and gifting generously. And oh my God, man, I— but I'm working on a book about money and man, so much good material.
Michael Ashcroft: Yeah, I mean, it's good to surface your own scripts, right, to see any lingering ideas you still have around money. But like, how is, how is the hardcover doing? Like, what's the, what's the on the, on sales and stuff.
Paul: It's doing far better than even my best case scenario.
Michael Ashcroft: Of course it is, Paul. Of course it is. It's so good.
Paul: It's, it's very cool. It, I've sold, I think, 250 of the early bird bundles and that includes a bunch where you could buy 2 books or support at a higher tier. And so the. Average price is above $100, which is amazing. And yeah, it feels cool. I still have this voice in my head that's like, you're only 40% to break even.
But after that first week of launch, I think I probably had 50 sales. I had 35 sales come in in one day and The majority of them were people I never knew, didn't, had never heard from, didn't know were following me. And one thing I realized was it was a completely different audience to a lot of the people that either joined the Pathless Path community or are figuring it out on Pathless Paths. It was a lot of people who love books, a lot of people who just thought it was a cool thing to support. And so learning a bit about that. But yeah, it's been really fun and now I'm starting to see, oh, there's all these possibilities to keep going with the physical products and, uh, figure out a lot of fun things I can do in the future.
Mm-hmm.
Michael Ashcroft: I'm honestly, I'm really inspired by your like constant innovation with little projects like this. Uh, it's really cool to see that the, the primary thing that you seem to be orienting on is still play and fun. Like it seemed like you'd enjoy doing this and it like a good challenge, but You weren't caring that much about making your money back. Uh, and it's just amazing to watch.
Paul: Yeah, I think now I'm okay if I didn't earn the money back. I think it's just been so fun to launch it and it's definitely a bit nerve-wracking. I do ask, I do wonder like, should I have just not spent the money and like taken a sabbatical with, with the excess money I earned from The Pathless Path, but I think the point of this path, and I keep writing it in everything I do, is do work that matters to me. And I think this is something I put on our agenda to talk about, like the state of online creation. The state of online creation is one that is awash with cynicism and nihilism. And to me, these are like my personal enemies.
I want to avoid cynicism and nihilism because they're the path to the person I don't want to be. And so there's so many pressures and incentives and opportunities and peer pressure that say, oh, just take the money, do this, do that. Oh, just cash in, do all these things. And I think it just matters to me to lean in the opposite direction. Which is incredibly hard because leaning in the opposite direction is not like people want it to be. It's not like, oh, doubling down on your passion and you make even more money because you're passionate.
It often looks like this book project, which is like very unsettling, very vulnerable, made a lot of artistic choices that were not ROI-focused. And so it's Yeah, it, in the moment it feels crazy and hard and lonely, I think creatively, but also it does seem like there's no other choice.
Michael Ashcroft: I love that. That's really cool. So what does this mean for next year then for you? I don't know.
Paul: I have no idea. Cool.
Michael Ashcroft: Awesome.
Paul: You probably experienced this with your course and I've experienced it with other things I'm doing is The hardcover's been selling. There's probably been sales. I'm probably selling, I don't know, probably sold 30 over the last 7 days. But there's stretches of like 2 days when there's no sales and I'm just thinking, oh, it's over. And in my head I'm like, all right, I can gift all these away. I can put them on Amazon for a reduced rate.
Good experiment. Time to pack up my bag and move on. And I am trying to lean— I'm trying to just feel all that because I sense the— I feel like I've been in a 2-year transition of becoming a dad and also just unfolding. I feel like I'm in my own chapter being lost of letting myself unfold to the next chapter. It feels like it's taking forever. And I don't know what it is.
I think I'm somebody that, like, the obvious path eventually emerges, but I keep trying stuff. I put out, like, feelers. I'll put out, like, I'll often, like, toss out ideas in my newsletter or in tweets and see what energy comes back. Nothing seems obvious at this point other than just write another book. But even that, I'm not sure I'm writing the exact books I'm supposed to be writing. And so yeah, I'm even contemplating just taking a sabbatical because we're doing this traveling village thing at the beginning of the year with 20 families going to 3 different countries.
Cool. But yeah, I don't know. What do you think I should be doing?
Michael Ashcroft: I decline to answer. I have zero idea what you should be doing. If I gave you a list of shoulds, I think you'd either rebel against them or I don't know. It just doesn't, doesn't seem like I could have any clue.
Paul: I think we've actually talked about this. I think one of the interesting paths is doing something around publishing other people's books, either coaching, investing in them. I like the idea of creating new funding models and investing models for authors. I really am excited about this idea of continuing to push reality in my favor. I think that this is where I most resonate with like crazy founders. I just have a feeling of this future in this new reality that will exist with writing and publishing and books.
And I feel like no one can see it. It seems obvious to me. And so I want to keep chipping away in that direction, but I'm not sure the right step. I think one of the things would be, uh, the Michael Ashcroft book?
Michael Ashcroft: Well, it turns out that one of the, the services that I need is regular poking to say, hey Michael, write the book, I want to read a book from you. Um, and I didn't think that would be a needed service, but like since you've been talking about publishing your friends' books and like going on that journey as a, you know, coach, editor, publisher, whatever, it's made me more likely to write a book. Honestly, I don't know why, but the idea of either self-publishing completely on my own or trying to get a book deal neither of which seem particularly compelling or motivating, but doing it in partnership with someone like you, that seems like a path I want to take all of a sudden.
Paul: I love it. The Rebel Alliance is forming. I also love that I don't even need to do anything. I just mention the idea enough times and keep asking you about it that you just start doing it. This is like ideal for me because I actually get so much satisfaction over inspiring other people to do things they want to do. So if I could somehow just build a life around doing that and not having to work for money, that would be my ideal end state.
Michael Ashcroft: Yeah. And I think that's worth, that's worth like aiming for. But that's also why, you know, you said it's not like shoulds, but it feels like you have an inner guidance mechanism that's helping you get towards that. And even if it gets a bit caught up sometimes in old patterns and habits, it's still working pretty well from what I can see. So I would just say do whatever you want to do. That's what you should do, whatever you want to do.
Paul: Yeah, I think the biggest thing is just the time available. I think if I was— I made a big mistake early in 2024. '04 and part of this year where I just kept saying yes to a lot of half-baked things. And that worked before I had a kid. I could sort of dabble, work on something for a little bit, try it. And after having a kid, doing that, that energy was just too distracting.
I'd have like 5 or 6 things I'm committed to but not really committed to. So I've just been more discerning about what I take and don't take. But Yeah, it's, it's been hard. I think one of the things I'm really wrestling with is should I even be spending any time online? I think it's very clear by writing my newsletter and posting online, it does help with book sales and I enjoy both of those, so I'll probably keep doing them, but I just feel like something is off with the state of online creation. I don't know how you feel about this right now.
Michael Ashcroft: I honestly, I, I haven't really wanted to create anything for public consumption in a while. I'm happy to make, um, behind-a-wall content, whether it's a paywall or just a subscription thing. But, um, I don't currently enjoy being on Twitter, so I'm barely there. I find Substack currently really aversive, so I don't really want to be there. And I don't know, I'm just I have lost the interest in, in making currently. It's coming back, but not in the models I used to work in, I think.
Paul: Yeah. What, what are you feeling with Substack? Because I'm feeling something's just off with that for me too.
Michael Ashcroft: I don't know if I might have to have like some settings somewhere, but I get like a digest of emails now and I never open it. Um, I haven't read anything in Substack in months. I never open the app. Um, I'm confronted with DMs and notifications and and just the vibes are off. I know it's a trite thing to say, but I just don't want to be there. And my Substack is lingering, not particularly used.
I'm wondering how I want to change that, whether it's going back to something like a normal email newsletter, um, or just, hey guys, here's my RSS feed. I think I want the days of RSS back, uh, rather than whatever Substack is trying to do.
Paul: Every elder millennial just wants Google Reader.
Michael Ashcroft: We yearn for the days, honestly.
Paul: Yeah, I think I'm feeling that on the writer side of Substack. I'm getting almost no email replies. I will get more comments than I did a few years ago. I get comments, likes on Substack, but I just get so few email replies. I'm actually getting more replies unprompted from people reading my book, finding my email, and emailing me than I will get from a direct reply from a newsletter. And that's very different than 2, 3 years ago where I would get 15 responses to the kind of writing I do in my newsletter.
So yeah, I just don't know what's next. Maybe we should build a new newsletter app.
Michael Ashcroft: The world needs another Substack. Absolutely. I don't know.
Paul: I think— Create Substack 2019. And launch that.
Michael Ashcroft: I mean, let's just do Twitter 2019. That's when it was the golden age. At least my— the recent one. But I don't know, I wonder, I wonder if the rise of AI has— if I had to know this as well, because it feels like so much more of the content on my feeds is sloppy in that way. And like, the moment I realize something is AI written, I just tune out. I just stop reading.
And I wonder if there's something about the— about that that's making it different?
Paul: Yeah, I don't know if it's AI written because I still read Venkatesh Rao and he's using AI in really interesting ways. He's basically asking the most gigabrain prompts and generating stuff I want to read. I think that's a really interesting use case, but I think what you're sensing is it's, it's almost like AI-assisted creation. So people are creating more than they would normally create at a normal creative rhythm or something like that. And then I think there's just a, uh, energy on Substack and writing online of people sort of circling a lot of the same things. And it could just be a quantity thing.
I mean, I just remember discovering people in 2018 and it was like, oh my gosh, I'm gonna read their whole website and go down a rabbit hole. But now I don't even find myself at websites ever, or discovering stuff that feels new and fresh. So I suspect AI writing is going to be some of the most interesting writing in the coming years, but most people are not doing it in interesting ways yet.
Michael Ashcroft: Interesting. Um, and certainly I, I have the shared experience of rarely having someone blog post, catch my interest, and then read the entire website. And I guess with Substack, it's because I guess they all look the same. Uh, it was just, there's no differentiation in aesthetic or style or anything. It's just, it feels Substacky somehow. It's the affordances of Substack make it feel like Substack writing, and that puts me off as well.
Paul: All right, so now we're doing the round, round robin questions.
Michael Ashcroft: Okay.
Paul: I was gonna, I was gonna ask what your favorite AI tool of the year is, if you have one.
Michael Ashcroft: Oh my, um, quite honestly, I have not been using AI very much. I'm gonna be honest.
Paul: That's, that's what I was suspecting from your reaction.
Michael Ashcroft: Yeah. Yeah. I don't know. The only thing I use, the normal LLMs, I use like ChatGPT and Claude and, and NovaFiller and that kind of stuff. But I haven't gone down the rabbit hole of like, oh, look, a, a website or, oh, look, a vibe codey app thing. Currently doesn't interest me, and that's probably a me-shaped issue rather than anything inherent about the technology.
But the more that AI is doing its thing, the more I find myself retreating into what makes me human. And that's just a real preferences thing. That's just what I'm doing, not even by choice. I'm just like going more analog and more like outside than AI and AI. It's interesting.
Paul: Yeah, I've found when it enables me to do things I couldn't do before, I really enjoy it. But when it's just doing things I already enjoy doing, I don't like that feeling or relationship to it. So for example, writing a book, using it for developmental editing, that is something that is very hard to pay for on your own as a self-publisher that everyone with a traditional publishing deal gets this entire suite of high-paid editors helping them craft the book. I can't access that. So using AI for that high-context-level window and getting the feedback on it is so valuable for me because it's so— instead of sending a draft to someone and getting this written feedback 3 weeks later, you can get it in an hour and get it from multiple sources. And I get so many ideas from that.
It's sort of like unstucking. And then I've been having like the nano banana images. I had a lot of fun with them in the past, uh, few weeks. But I do find that sort of fades over time. I think the cool thing will be once you can edit the images, because then you can combine your own creativity with like really quick prompts or things you couldn't easily do on your own or wouldn't do on your own. But yeah, it's weird times.
I think there is sort of an evaporating effect to AI of work motivation that people are experiencing that hasn't really been priced into how people think about work. So thinking about it from that angle, but I don't really have good predictions how any of this is going to play out.
Michael Ashcroft: I'm really curious to see what happens. As the companies that have stopped hiring and training juniors in favor of AI, how that will unfold in like 5 years' time when there are far fewer juniors doing— have been through the mines, if you like, and whether the AI promise actually paid off to be able to replace them. That's going to be a really interesting question for me to be with.
Paul: I suspect companies doing that right now are not the sharpest, most competitive companies. I think if I was— I think I would expect good companies to be hiring more junior people because they know how to use these tools and build in different ways. And so you still need the future talent force that is like flexible and adaptable. But yeah, it's going to create this weird two worlds of sort of companies that are coasting. And I mean, Could just create like pathless companies that aren't growing anymore and are just cashing, enjoying pathless paths as companies.
Michael Ashcroft: Interesting. Pathless company.
Paul: All right. Favorite book of the year or thing you read this year?
Michael Ashcroft: I mean, The Pathless Path hardcover by Paul Millerd is sensational.
Paul: You're quoted in it.
Michael Ashcroft: I am quoted.
Paul: And you don't like your quote. You got angry at your quote when I sent it to you. You're like, I don't feel wonder anymore.
Michael Ashcroft: That's not what happened. It's just, it's funny being, being confronted by, um, by my own past self. Yeah, exactly. Immortalized in delicious hardcover forever. Um, in terms of— okay, I, I actually went on a reading spree before Etienne was born, which I really enjoyed because I knew I couldn't do it for a while. And I read 3 Ursula K.
Le Guin books. I read The Dispossessed, Left, uh, Lathe of Darkness and Left Hand of Darkness. Oh Jesus, Left Hand of— oh, I'm tired, man. It was The Left Hand of Darkness and The Lathe of Heaven and this disaster. And they are just such wonderful books, and I just deeply enjoyed falling into those worlds. As someone who doesn't read enough fiction, uh, and always defaults to some kind of like, what can I take notes from non-fiction, um, That was just wonderful.
Uh, I'm looking forward to getting back into reading that kind of thing again. But, uh, it's difficult with a child, I think, to justify that kind of spacious reading, but it'll happen.
Paul: Yeah. There's often time, especially the first year, but I think just the focus is the hardest thing. Yeah. Yeah, exactly. It's like, yeah, for me, I had a few, I'm looking, I really enjoyed Things Become Other Things. This was Craig Mudd's walking memoir of walking around Japan, and he is from eastern Connecticut, I think pretty close to where I grew up, and then ended up in East Asia on his own pathless journey.
And so I think I found a lot of resonance to that. It was just a really well-done book. I think it— I almost by default don't expect many nonfiction books to deliver these days. And this one was just fantastic. I think the others were, um, Nat Eliason's book Husk. I really enjoyed that.
That was a fun read. And, uh, let's see, what else did I read? I read a bunch of stuff. And then Scott Britton's book has been really interesting to read recently, Conscious Accomplishment. I feel like no one has ever captured all the phases we're going through on these journeys and sort of like this personal growth-ish. He's going down deep into the spiritual rabbit holes, but I think anyone who's gone down like a self-development-ish path on their own, he just captures the detail of all these phases, these ups and downs, this phase called inner purgatory.
It was just really cool to read. He also started the book 2 years ago and I read his first draft and basically challenged him to go all out with the personal story and he crushed it. Like, it's so good and I'm just so happy that, um, someone took that advice because I've given that feedback to many people and most ignore it. They just run the playbook.
Michael Ashcroft: It sounds like that's your role though, is helping books come into existence in the best way they—
Paul: Maybe that's it.
Michael Ashcroft: I don't know. Maybe that's it.
Paul: Books are just, yeah, I don't know. We'll see. I'm just gonna receive that and see where it takes me. All right. What other things did I have? Question for 2026.
Do you have a question you're thinking about or asking for 2026?
Michael Ashcroft: So if this year and a good chunk of next year is parenting and health, health. Um, I do need to make money and I want to make money and kind of grow into that. The question I'm in is something like, how can I re-engage with that professional making money, being a business owner energy such that I can provide abundantly for my family while still being a present father and able to not lose myself in it? Um, it's that integration phase basically that I'm looking, looking into next year.
Paul: If you figure out the answer, you tell me too.
Michael Ashcroft: I'll let you know. I'll write a book about it, um, once I've, once I've figured it out. But it just, it's one of those things that needs to get done. I need to make money and that can't be put off forever. And since it needs to happen, what's the best way that it can happen, I guess, is the question.
Paul: Yeah, a question I always try to ask is, what's the most generous way to do this? And then what's the, what's the more fun way to do this that I am not currently imagining? That usually leads to interesting approaches. But yeah, these are good questions. I guess my question for 2026 would be, what does it look like for a pathless family to build a family-first life and also thrive, explore, adventure, and do the work that matters to us. And man, I feel like I'm going to learn so much going on this traveling village experiment, but I don't have good answers yet.
Michael Ashcroft: Yeah, I'm looking forward to seeing what version of you comes out the other side of that experience of the traveling village because it sounds really fun.
Paul: I think it will be more interesting to see what happens with Angie. I think it will be great for Angie to have a lot of, uh, female role models that are different than what she's been exposed to, because I think a lot of, um, the people we know are just doing like the full-time work thing, and that's been hard, I think, for Angie because a lot of her creative friends either don't have kids or work full-time, right?
Michael Ashcroft: And this is the perennial question that we're in, I guess, is that all of us— how do you reconcile all of this stuff while having very few role models and examples of what is even possible and what can be done around parenting and work and lifestyle? So uncommon that we don't have many stories.
Paul: Yeah, it's very, it's very weird. I think, um, I don't have I had people, I have a few people I look to, but those people tend to be like a lot richer than I was, and that's why they stepped off the path. So money adjusted, it's hard to follow that. But yeah, it's very interesting. I also think there is a, there's this default male archetype you can always default into. And so I could easily just sort of channel my fears and say, you know what, I have to work full-time.
Uh, we have to just figure out what we need to do. Daycare, you taking care of, uh, our daughter. And this is what we need to do for the next couple of years. I also know that's not totally true financially and that we have a few years of buffer. To experiment and play. And so a lot of the next phases of our journey is me releasing to, I think, um, the path that Angie's stepping into.
Like, I think for many years we oriented a lot around my journey because I was either making the money or, um, I was just ahead of her on the work journey. Now that she's like finished this book and stepped into that, I think She may not pursue work, but I think she'll— she's going to find a different version of herself as this book is completing. So just being open to like how that evolves and emerges. We just recorded a podcast ourselves today too. So this will be either before that or after it.
Michael Ashcroft: Will there be an English version of this book that I can look forward to reading?
Paul: I am going to translate it with Angie. Cool. Yeah. So 2026, it should be out and I'm going to pump this book so hard.
Michael Ashcroft: She should use every unfair advantage she has. And you're definitely one of those.
Paul: So I get very skittish around. I mean, I promote my books plenty, but I still get nervous around like asking for support and I have a lot of issues around asking for help. But for some reason with her, I'm just like, I'll reach out to anyone. This is easy. So once we have that English edition, I think it's really, yeah, it's definitely going to take off in Taiwan, but I think the English edition will be really interesting too.
Michael Ashcroft: Cool. I look forward to reading it.
Paul: Awesome. Any other things we should cover?
Michael Ashcroft: Didn't you have a little game at the end that if we have time?
Paul: Who said this? All right, so I'm going to ask you. I need to turn this into like an Instagram reel, I think. Who said this? Dictator or hustle bro? The goal of every struggle is victory.
Michael Ashcroft: Oh no, I want to say dictator. Surely Stalin.
Paul: Okay. Okay. What is work? Work is struggle.
Michael Ashcroft: That also sounds dictator to me.
Paul: That's Mao.
Michael Ashcroft: Okay, good. That's reassuring.
Paul: Okay, it is better to live one day as a lion than 100 years as a sheep.
Michael Ashcroft: Uh, Hustle Bro?
Paul: That's Mussolini. Okay, um, okay, let's see, next one. Unity, self-reliance, and hard work are the pillars of a strong and prosperous nation.
Michael Ashcroft: That's definitely dictator.
Paul: Kim Il-sung. Okay, but it could be like a right-wing influencer.
Michael Ashcroft: It could easily be. Yeah, I can imagine that any Twitter account kind of saying that.
Paul: Only struggle discloses to it the magnitude of its own power, widens its horizon, enhances its abilities, clarifies its minds, forges its will.
Michael Ashcroft: Oh Lord, that sounds like some Roman emperor.
Paul: That's Mao again.
Michael Ashcroft: Mao again. Okay.
Paul: So they're all world leaders, all leaning on the socialist struggle. I think one interesting thing— I didn't want to call out any Hustle Bros. I don't want any unnecessary beefs right now. But one thing I started noticing is that people like Lenin and Stalin are always talking about like the never-ending struggle. We must struggle now. We must sacrifice.
For the revolution. And it's almost indistinguishable from how many people in the hustle world communicate these days. Like, you got to struggle in your 20s for payoff in your 30s. And it's— humans love this shit. You can ride this language to wealth or power, and I don't know how to defeat it, but it works.
Michael Ashcroft: It feels like it all stems from a place of being dissatisfied with where you are. Right now is not good enough. It's unacceptable. We have to get over there and then we'll be happy. Then we'll be strong and powerful.
Paul: And yeah, it's the same pathology, but the satisfied person is going to meet this person on their rise or on their hacking of audience and be like, eh, it's not worth really competing with them.
Michael Ashcroft: Yeah, but then they don't get amplified. They don't like say, well, here's my view, because there's no point. Let's just go play.
Paul: Yeah. Uh, and then their ruler becomes a hustle bro. Great.
Michael Ashcroft: Is there a way out of this trap, or are we doomed? I don't know. This is like a hustle.
Paul: This is the question I'm gonna close this podcast with. I think that is the question for the decade. Can we transcend hustle culture? I don't know.
Michael Ashcroft: I want to believe that we can. I hope that we can, but it remains to be seen.
Paul: We can't even get Johnny to show up for, uh, a podcast after a rough night's sleep. He is not— he doesn't even have children hard enough.
Michael Ashcroft: No, more grinding, less not grinding, Johnny.
Paul: Honestly, how, how are we ever going to achieve anything if we But this was fun regardless. Shout out to Johnny Miller. Hopefully you can join us in 2026 with a baby. Yeah, I think the baby's going to help him. It's going to lock him in.
Michael Ashcroft: Yeah. All right.

