#170 Apprenticeships, Sabbaticals & "Good Work" — Steve Schlafman & Matt Yao on slowing down, deprogramming, unlearning, learning from others, deciding to quit, going on a sabbatical, not being jealous anymore, competitiveness and enoughness, finding good work, ambition, the apprenticeship, Downshift, decelerator, marriage, family and reframing money

[00:59] Paul: Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life. Welcome to today's episode. We have two guests today, Steve Schlofman and Matt Yao. I'm excited to talk to them for multiple reasons, both of which their personal journeys are very interesting. Steve is a father ahead of me on that path and hopefully someone I'll continue to learn from, but also a former investor venture partner.

He thought that was his goal. And when he reached that, that and other life circumstances led him in a new direction. He's been in the process of reinventing his career. He's now a coach and launched something interesting recently. Which he is calling a decelerator. I love this frame, and his hypothesis is that many people need help in the transitions of life, something I've seen up close with the hundreds of people I've talked to, and love that he's working on this.

Also talking with Matt Yao today, originally connected with him, I think we had a phone call when he was thinking about taking a sabbatical He decided to take that sabbatical and has really been doing an interesting job of chronicling that journey, giving me a lot of insights into my own experience back in the day and helping so many other people. Highly recommend his writing. I'm going to link up to both their writing, which both of them are writers and very thoughtful. Uh, but Matt has recently started an apprenticeship. Thinking that coaching could be a path for him with Steve. And so we're going to be talking about that journey, both their journeys, how this apprenticeship fits in with that.

And I think we're going to have a fun conversation. Welcome to the podcast, guys.

[03:04] Matt Yao: Thanks, Paul.

[03:06] Paul: So I want to start with Steve. We're going to give both of them the question I always ask all my guests. Steve, what are the stories and scripts you grew up with? Around work? Yeah, it's interesting because I was raised by a single mother who worked two jobs. So her jobs were waiting tables on Sunday, Monday nights, and then her other job was literally hanging wallpaper and painting.

And she worked nonstop. And there was a very good reason why she worked nonstop, but That was a very important message that I received. Conversely, my dad who was in the picture, frankly didn't pay child support and he didn't work very hard in terms of fully realizing his potential. And so it's interesting because I almost got these like very mixed scripts and stories about work, But ultimately, the one that prevailed was that if you don't work hard, then you're going to run out of money and you're going to be poor and you're going to be living paycheck to paycheck, hand to mouth. And so that's the prevailing story that really drove me for the better part of 20 years is that work means security. And then over time, it became work means respect, wealth, power, prestige, and things like that.

Yeah. What about you, Matt?

[04:51] Matt Yao: Me, I grew up in the suburbs of Northern Virginia to two parents from— they were immigrated from China. And so in order for them to even come here, they basically had to be the number one in their town, number one in their village, so on and so forth. And they both came to the US to get PhDs in chemistry, but then ended up basically never using it in their entire career. So I think that definitely influenced me growing up. I would say I had the benefit of not having tiger parents. They very much encouraged me to try hard in school, but I never got rewarded or punished for report cards.

And so I felt like I was always naturally following my curiosity. Even if they were in the background kind of like steering me along the way. But in a similar way to Steve's, I never questioned work. It was always like work is just something that's— you have to do. It's something that you need to work hard at. And I didn't realize a lot of these lessons that I'm learning now with my sabbatical and things like that until 2 to 3 years after graduating and working in tech.

[05:56] Paul: Yeah, I think it's such a common thing. I— my parents didn't go to college and for them, like succeeding in school and the workplace was a way to get safety and security as well. And it's so common. I hear this with so many people. I think the hard thing is though, like once you've sort of figured out, oh, I could probably get enough money to like earn security and that safety, how do you shift to a new mode? And that seems to be a lot of what you're thinking about now, Steve, is that right?

Yeah, yeah, yeah, absolutely. It's interesting because I think back to my investing days where, you know, I would get these bonuses and they weren't like hedge fund or private equity or investment banking bonuses where, you know, 7 figures, but they were nice. And I remember always getting them and feeling like, wow, but nothing really has changed. Nothing fundamentally has changed. And that sort of that void eventually led me to be like, okay, well, if I keep on making more money and I'm not feeling any different and I'm just wanting more, like something's up. This doesn't really make a whole lot of sense to me.

And so the better part of the last 7 years has really been dedicated to finding my way back to myself and to home. And frankly, helping others do the same. And what I ultimately discovered through largely trial and error, that it really comes down to slowing down rather than speeding up because for so long I would just try to speed up through these moments and it would just perpetuate the same patterns and habits and behaviors. Yeah, and that was something you sort of figured out after, You took the leap, it seems. I mean, it's funny. We were having— for sure, for sure.

We were having an exchange. You used to have an email, which I had in my address book, High Output. And you've since moved on from that brand. But talk to me about that. I think when a lot of people take the leap, they— and there's probably this necessary stage of like having to really push and prove to yourself, okay, I can survive on my own. Even if you've done it in employment, you sort of have to prove it to yourself again on your own.

But talk to me about like, what was the thinking around high output and why are you not using that anymore? Well, the reality is, is that there wasn't a whole lot of thought that went into it. And I remember leaving primary venture partners where I was a venture partner, where I was investing in coaching. Simultaneously, and I had left and I'm laying on my bed and I look up on my bookshelf and I see High Output Management by Andy Grove. And I'm like, oh, High Output. That's a perfect name for a leadership development coaching firm.

And I went and to much to my wife's dismay, who encouraged me not to do that, I didn't listen to her and just forged ahead. And what I ultimately found out, and I've written about this, is that I ultimately took on that persona of high output. And even though I had transitioned, I was just driving harder and harder and harder to the point where it became very clear after a few years of that, like, this is not serving me and this is not who I am. And I actually wrote an essay about it that was titled, I Am Not High Output. And that was, I mean, really the beginning of this shift into downshifting my life to really figure out what it is that I wanted to spend my time on and really devote myself to. That's a scary shift for people.

I think I was writing about this recently and talking about how sort of a mediocre or like medium output Um, but on terms you actually enjoy doing things you like can sort of end up with way more stuff that you actually appreciate. Like, this has been my journey with writing. I don't really write that much, but I, I write most days. And so I've been able to produce like far more than I ever produced of importance to me than in my previous path where I was constantly on. You're just do, do, do, do over and over again. Is that something that was like, how did you feel about that?

Like, were you scared of losing your edge at the beginning? Oh, completely. What's so interesting is I, as I'm listening to you, Paul, like I can't help but think of this exchange that I had with a former coach of mine, Dr. Josh Claypau, who works with a bunch of really well-known investors. And he helped me ultimately break free. And there was a moment in our coaching relationship, and he's a former clinical psychologist, and he said to me, what if you just were a dad and you coached?

And I was like, well, I don't, I don't. And at first it was such a foreign idea. And the more that I sat with it, it became very clear to me that that's exactly what I needed. And there was literally a 14-month period from roughly like October of 2021, I want to say, to the beginning of 2023, where I said, I'm literally doing nothing but coaching and writing. That's it. And I got a studio in New York City for my office.

I called it the Cocoon. And that's all I did was coach and write and be a dad. And that was where I really began to unravel a lot of this old conditioning and deprogram myself and unlearn all these things that I had to unlearn. Is that inspired by Bill Plotkin by chance? At the time, I wasn't familiar with Plotkin's work. It just instinctively came to me as like, yeah, this is this is exactly what I need in this moment.

It is that place of stillness. And it wasn't like I was doing nothing, right? I was just doing the things that I really enjoy doing, which is creating and expressing myself and serving others. Yeah. But so for people that don't know, Bill Plotkin talks about this journey of soul descent and going into this cocoon stage where you're sort of protecting yourself and committing to the things that matter, but He also talks about it like that stage is very hard, right? Because one, you probably feel a bit silly and also people are probably judging you.

Like, I'm sure you had the voices in your head, if not explicit voices to you of like, I know my former venture people are probably thinking like I'm a loser, I'm out of the game or— Completely. I had this experience where when I told a very good friend of mine who's a very well-known influential investor, still friends with him today, that I was going to leave and put my fund aside. He said, dude, take a break, take a month off and don't do anything drastic. And of course I ended up making that decision. And on the other side of that decision, while I was in the cocoon, it's interesting because what I noticed are these tendencies to want to go and create structure because there is very little structure. And so what I found was almost like grasping for new projects.

Checks and like beyond the writing was great because I have always wanted to do that. But beyond the writing was like, oh, I have this idea, I have this idea. And I had to really get to know these behavior patterns. And, you know, I'm a big fan of internal family systems is really understand those parts and the way they're conditioned and understand them and see like, hey, there's a benefit to these and there's also a downfall. The other thing I noticed in this moment is that sort of fear of falling into obscurity, like, oh my God, have I peaked? Is this, is my best work behind me?

Like, am I just going to fade away? And so those feelings were definitely marked by this period. Matt, I'd love to dive in a bit to your story. So I have a quote in my first book, which is based on my own experience and just talking to many people, which is the longer you spend on a path that is not yours, the longer it takes to find one that that is. You seem to benefit, I think, from this emerging info space of people like me and Steve and others sharing our hard-won lessons of like our slow, dumb realizations. How did you think about taking a break?

Like how many years were you into your journey and like how were you thinking about it and looking for examples of like how to avoid some of the traps?

[15:16] Matt Yao: In the moment during the journey, I had none of that planned or that methodical approach. To rewind it, you know, I have to talk about my first job out of college, which was being an associate product manager at Uber. And, you know, it's not, it's really hard to compare to different stages of your career, but for me, like coming out of college, that was my dream job. That was basically the peak. for me to get like exactly what I wanted. And it was a great job, great program.

I'm still really good friends with a lot of people in that, in that cohort. But then I got laid off 10 months, because of COVID Uber laid off 25% of the workforce. And then I was basically in 3 months of a slump. I was, I was at home in the East Bay in the summer and it was so hot that I couldn't go outside until the evening, like until the sun had set. And I would wake up every morning super anxious looking for jobs. I would apply to every single job and it was just a scary world at the time.

There was no vaccines in sight and I was basically waking up every morning worrying about getting a job. The idea of not finding a job after being laid off was, yeah, it was, it was just job, just a hunt for a job. And it was just a really weird moment in life because I had severance and I was getting unemployment. So it wasn't even like I had scarcity of money, but in my head I was so scarce. And then the job that I got afterwards was a product manager at another tech company. I was fully remote and I basically just found myself skiing in the winters, living in Hawaii.

I was making good money. And so in Hawaii, like I would basically just buy anything I wanted without hesitating. I would go buy ahi tuna steaks. I would go eat sushi. Just no hesitation on like, is this worth it? And on February 17th, 2022, I double-checked my journal yesterday.

That was when I was like midway into The Pathless Path and I said, okay, I'm going to do it. I'm going to quit my job without another job lined up. But I didn't end up leaving my job until 10 months later. So When you talk about how it seems like I realized these things before you guys, I wasn't comparing myself to you guys at all. And I was comparing myself to what I thought it would look like, which was a very fast, intuitive decision. And so it was basically 10 months of tension.

One week I would say, you know, F this, I'm leaving. I'm putting in my notice on Monday. The next week I'd check my bank account and I was like 25, 26. So I didn't have a ton of savings and I would get super worried about having to get a job, running out of money. And so I basically flip-flopped on that decision for 10 months until ultimately it felt like there was no other choice. And I was, I was also at peace with it.

[18:12] Paul: Well, what's crazy as I listen to you, Matt, I think about my experience where I enrolled in my first coaching program in 2017, shortly after I resigned as a partner at RRE Ventures. And I didn't really fully step into coaching until like fall of 2021. There was almost like a 4-year period where I was like oscillating between these two identities, between the investor and the coach and the investor and the coach. And then eventually, like after 4 years of that, it became very clear with some support that it was like, okay, this is the identity that wants to prevail because it's more connected with what I value and who I really am at the core. Yeah, it's similar to me. I started doing experiments in 2013, 2014.

Yeah. And then I didn't quit my job until 2017, and then I didn't really figure out that writing was something I really wanted to commit to and like writing in conversations like this until 2019. So 10 months is pretty good.

[19:22] Matt Yao: Didn't feel like that in the moment. It felt like an eternity.

[19:27] Paul: Yeah, there's, there's also a lot. I'm curious how aware of this you were, especially with the pandemic. There was all this attention about people leaving their jobs and a lot more people doing it. Like, I, like when I quit in 2017, I felt so much shame. I did not know anyone doing what I was doing. So did you have like models you were looking to and people you were trying to emulate?

[19:58] Matt Yao: Definitely not as many people that I know of now, but every single time I came across someone, I would, I would reach out to them and you were one of them. You were the fir— you were one of the first and towards the end of it, like in November, December when I was really gearing up for it. I reached out to literally every single person that I knew that had taken a career break of some version, even if they had just taken 3 months off and gone back. And I wrote a piece, I think it was called Chronicles of the Career Breakers, and there was like a dozen people, and that was everyone I knew. And I would even ask friends of friends to introduce me anytime they mentioned, oh, I had a friend who quit their job. I was like, oh, can you please put me in touch?

Like, I would really love to just talk to them because I, I That was all I knew. I, it was just tho— that handful of people.

[20:44] Paul: Yeah, that's, that is one of the biggest recommendations I give people is like find people on the path ahead of you. For the most part, they're also happy to connect because they're sort of lonely on their journeys as well. So it's fun to see other people thinking in the, in the same direction. But also the thing that jumped out from both your stories is like I had to take this different path. And this is the thing that people don't understand, and they shouldn't try to like talk themselves into thinking they should do their own thing, which is that 95% of the people I talk to are talking to me because it's like, I know I need to take a different path than the default, and I am talking to you because I need recipes, I need stories, I need information, I need more input, I need more ideas, and I need friends. Along the way.

When did you, Steve, start thinking more, less around like, okay, I'm going to reinvent myself on this solo path and more toward this metagame of thinking about, okay, how do I actually build a life and unconventional path? Well, I would say that started after my first child was born. And she was born in 2019. And so this was around the time, like, as I was literally leaving primary to step more fully into coaching full-time. And then what happened was, is I've always had, like, this desire to be a very engaged father, as I like to say, because I, you know, I want to be the father that, you know, that I always wanted. But never had.

And so that began to come into view of like, what's the role that I want to play in my child's life? And then the second child, which came in 2023, that summer was like a pretty big awakening for me in terms of bringing me down to the ground in terms of really helping me see that there's something way bigger than myself and that putting my career and my ambition front and center in the traditional sense isn't— wasn't going to work because it was at odds with being a very loving father. And fast forward, that cut down my work hours pretty dramatically where, you know, I was now working 30 to 40 hours a week. And then of course, we started thinking about where we wanted to live and ultimately moved upstate.

And so to me, I think about there's some really big threads in my, in sort of the tapestry of my life, which is family, service through my work of working with high performers in transition, creativity through writing, and then nature and health. And like, Ultimately, what I've figured out almost haphazardly is that when you start to see your life as a broader tapestry, that it starts to create more dimensionality, more meaning. And I've figured out one way or another that I can be happier, thriving, and feeling like I'm exactly where I'm meant to be in my skin. Without any reservations whatsoever. And so it's a really beautiful place to be. But that process took a while.

But I would say the kids were the thing that really catalyzed that. Yeah, it's interesting talking to so many parents these days, especially in our generation. I just had a daughter a year ago, and you sort of think like, oh, as soon as you have a kid, you're going to get like serious. About life and then like the goals, like you need to work a lot, right? And a lot of people have that script, right? And they use it to like double down on work and their careers and deliver this sort of security.

But I think I resonate deeply with the goal of like being present and being around. And the truth is that you basically leave money on the table. To do that. Yeah, completely. I think that's the thing people have the hardest time with is they want it all. And I'm not sure you can have it all, especially when your kids are very young.

Yeah, it's a challenge for sure. The way that I'm settling into this now, especially given that we've launched Downshift, the decelerator that's going to be the container for what I put forth into the world going forward, is that when you have young kids and you've chosen to live a life that's multidimensional, is that it requires a very long time horizon where it no longer becomes about speed. It becomes about commitment over a long period of time towards something that's ultimately bigger than yourself. And so for me, the way I look at where I am now is that I'm looking this over 5 to 10 years. So as long as I'm just moving it forward a little bit every single day, it's exactly where I'm meant to be and what I need to do. Where does that trust come from?

Well, the trust comes from, well, for me, I've done a lot around this idea of flow over control. Like it's kind of a mantra of mine right now. Because I have a lot of control tendencies of wanting things to be a certain way at certain times. And what I've begun to appreciate through the help of a coach by the name of Steve March is like, life is this unfolding path. And that when we actually see that we're just embedded in these complex systems that are always unfolding, like you can't help but start to like, trust this process. Like, there's like real intelligence.

And what I find is when I fought that process, that it would be very uncomfortable and disorienting. And the more that I relax into it, the more I just, it feels natural. The last, the other thing I'll say, it's the big difference between scarcity versus abundance. Like, it could be like, oh, well, if I'm not moving fast, then the opportunity I'm going to lose and my ideas aren't going to win out in the marketplace. And And that's just ego talking. And so for me, it's how do I begin to see that over this longer timeframe, there is a tremendous amount of abundance.

So that helps me trust and relax into it as well. Yeah, this is actually what I'm writing about now is what it feels like to find this good work and how do you lean into that? And you wrote something yesterday, which just like jumped out at the page. Me. There's an indescribable rush and a profound sense of aliveness when, after years of wandering, you finally find your niche in the world. All the longing, struggling, efforting, and questioning seem to fade away.

You know you're exactly where you're meant to be— home. And it's like I got chills reading this because it is exactly how I felt. Like, I had this feeling at the end of 2018 and the beginning of 2019 I'm making no money, I have no plan, but I have this connection and there's just this knowing that, yeah, it was this sense of home. And it was very bizarre because I was finding it when I was in Taiwan, which was also not my home. Beautiful. Yeah, I'm thinking about when the idea for Downshift came.

Early January, I'm doing dishes at 6:30 in the morning in my kitchen before my family's up. And the inquiry of why are there no— why are there only accelerators, no decelerators? Point that I'm getting at is as soon as I had that inquiry, it was like in that moment, I just knew. I'm like, this is it. And there was nothing that could, like no analysis, no case study, like no whiteboard sessions. It was just this deep inner knowing that this was going to be the thread that I was going to pull for the long term.

I knew. Matt, I'd love to hear sort of the phases of your sabbatical after taking the leap and how you thought about like what I call is like the search for good work, right? And I don't know if you were thinking of it in those terms, but from the outside it was like, Matt has sort of realized there is this deeper connection worth chasing. And I could sort of see like, oh, that is a person serious about the quest for like finding this positive lasting relationship with work. Does that resonate? And I'd love to just hear like how the different phases of your, one first year of sabbatical work.

[30:09] Matt Yao: The quest for good work, looking back resonates, but in the moment I had no idea what I was doing.

[30:14] Paul: Yeah.

[30:14] Matt Yao: I was just like flailing around like a, like a fish outta water.

[30:18] Paul: I think to reframe it a bit, would, would you say at the beginning it was a quest for avoiding bad work and sort of creating this space for other things to emerge?

[30:32] Matt Yao: Honestly, I think at the very beginning, I was just trying to stay busy with things that I felt were interesting, but not necessarily like the calling yet. I didn't really know. But I think it really starts before I actually left my job. Once I set the intention of taking this sabbatical, it was interesting. I had no idea what these products were going to be. And then once I had a more concrete timeline.

Things just started happening where I had this idea to start this climate newsletter. That wasn't something that I came up with before I knew I was going to take a sabbatical. But once I knew I was going to have this time, I was like, oh, I've always been interested in climate tech. And I feel like there's an opportunity to tell stories around companies that are helping to make the world a better place. And then a friend knew that I was planning to take a sabbatical. So he was the one that approached me about starting a podcast.

So it wasn't even my idea. So there's something about like once you set these things in motion, like things come to you, maybe because your attention is starting to go in different places. And so when I started my sabbatical January 2023, in my head, my projects were my blog, my climate newsletter, the podcast with my friend. And then actually in my Notion, like planning thing, I thought I was going to also make YouTube videos because I was like skiing a lot. I've always traveled, I've always loved flying my drone and carrying around a camera and just quickly realized I had no time for 4 projects, which I thought I had, which is interesting.

And honestly, I spent the next, the first 3 months I was skiing in Tahoe, really grinding at these projects, sticking to a deadline every 2 weeks for each thing and just realizing that I was a bit lonely and that it was, I was grinding and grasping for things. And in hindsight, I wish I would've just taken like a month or two off. I didn't realize I was burnt out, but I was. And so that's usually my one piece of advice to people is don't just rush into like a full, don't be your manager. Like don't put a manager in your head and sort of police yourself and tell yourself these are things you gotta do. The next phase of my sabbatical, it was more experimentation, but in a more like proactive offensive mode where I kind of got out of that initial funk being in Tahoe and I was, found myself in Southeast Asia surfing in Indonesia.

This is where I just discovered the profound, very simple and obvious idea of just living one good day at a time. Yeah, I was living in this like, home stay where it was $18 a night and I was renting a scooter for like $4 a day and I was going to this like buffet that was $2 a meal. And so it was kind of like play money. You could just do whatever you wanted. And so that's where I was like, okay, and I'm also on a different time zone. So people aren't really like pinging me or asking me for my time.

I just discovered what I wanted to do every day, which was like sit down at a cafe, get some work done, write, read a book. Spend some time outside, do some yoga. And then I would say like the rest of the year was more exploration around these projects. I was still, for the most part, working on these like cadences and deadlines that I had set for myself. But also in the background, I had started to explore coaching. I was just not writing about it because I wasn't sure.

I wasn't an expert in it and I wasn't sure if that was the path for me. And it's interesting looking back now because I feel like the thing that I'm headed towards, coaching with this apprenticeship, it was like this thing that came to me naturally. I just found myself having conversations with coaches who are reaching out to me. And here I am, this, this guy in his 20s. I quit my job. I'm not making money.

And there are coaches who have the real title coach reaching out to me. And I thought it was mind-blowing to me. And I had to sit down and kind of reflect on why, why are they reaching out to me? And I realized it's because I think about the same things. I'm writing about a lot of the same topics. So I feel very grounded and at ease with this new path that I'm exploring.

I know that I'm not getting into it for the wrong reasons because I wasn't even aware of coaching. I just sort of stumbled into the thing that we both see and look at the same topics around identity. Spirituality, work, meaning, etc. And then for the rest of my sabbatical, I felt like I was still pursuing— I think the through line is that the more I spend, the more time I spend on this path, the more intuition I build on what I'm curious about and the more comfortable I am focusing on just a smaller and smaller number of things. Like the concept of jealousy has sort of evaporated from me because if you're doing something that you want to do, you don't feel jealous of someone doing something else because you don't want to be them. Like, I love rooting for friends that are just on different, doing different things, succeeding in their own ways.

And then here I am perfectly happy doing what I'm doing without much desire to do, to be in their shoes. So it's a good feeling and the journey continues.

[35:53] Paul: This, this is such an interesting point. It's, it's something I've mentioned to many people, which is that when you sort of soften into your path, you find your own way, you have a deeper self-awareness of what you want to do. The, like, amount of jealousy and envy you have of other people is almost zero. And I, what I've noticed is that often morphs into getting excited about other people's paths. Even more because it's like, ah, yes, they're discovering this secret I have too. And like, finally we can talk about it.

That's what I'm experiencing right now. The last 2 months has been that for me. And it's a, it's a wild feeling because there's like, it's a fundamental reorientation of how you see the world and engage in it. Yeah. And I mean, you used to be in the venture world, so it is inherently, it is like literally a competitive competitive world, right? You're competing for deals, you're competing for access, you're competing for information.

And yeah, like, not being competitive is not going to be super helpful. Yeah. Yeah. What— talk, talk to me a bit about that more. Like, what— maybe a couple of years ago, were you looking at other people doing independent things through a different lens? Yeah, I think for me, It is, this even is a relatively new shift for me.

I've spent a lot of time off social media for the past, I mean, past 2 years. I first took a 6-month break about 2 years ago. And then most recently I took about an 8-month sabbatical. And for me, if I'm being completely honest, I haven't shared this on Twitter, though I intend to, is that it was a very triggering place for me. Kind of just seeing like all this ambition and hustle and humble bragging and, and like deep at the core, I think there was a shame message that I'm not good enough, that, that, that I'm less than in, in certain ways. And I went through the Hoffman process in October, which was really transformative.

And on the other side of that in January was this like fundamental belief that like it doesn't really matter. What other people are doing. Like, my sense of enoughness is not predicated on achievements, um, and it's— and at the end of the day, I need to be comfortable in my own skin. And so as a result of that shift through Hoffman, coming out on social media now feels way more generative and fun, especially in the context of Downshift, because as you said like I found the thing that I'm going to pour my 30 to 40 hours a week into. And it's so aligned that I want to help other people and I want to celebrate other people. And it's a really unique opportunity to use influence and reach to do that.

Yeah, that's beautiful. It's interesting because I see a lot of people struggle with that on social media and That has not really been my experience. When I see other people like going super hard or super ambitious, I'm just like, whoa, that's an interesting human there. I don't have that. And now that's my framing. Like I look at any number of friends like Justin Welsh who lives down the street, like that guy just has a level of drive.

He's a hard worker, yeah. And it's crazy and it's impressive and it's that, that's not me. And I know that, it's just not me. Yeah, for sure. Matt, I'd love to hear more about some of the first moments you realized— I mean, you talked about this a little bit already— coaching. What are some of the first ways you— what are some of the first experiments you took to sort of experiment with that?

And how have you leveled that up over the time— over time to now you're doing this apprenticeship with Steve?

[39:59] Matt Yao: Yeah, I think it started out without me knowing. I was just, I was interested in, in what coaches had to say. So I was following some of them on Twitter and just consuming stuff. I mean, I followed, started following Steve, um, at least before 2019, because in 2019 I did the Ultimate Annual Review for the first year. So I was just passively consuming stuff from coaches. I liked what they had to say.

And then between May and July last year is when there were a few moments where I was asked to go on like a career podcast and talk about quitting my job. An executive coach interviewed me for her blog, and then another coach reached out to me to chat. And there's just all these moments where I was like, why is this happening? You know, what do I have to offer? And so it's like this mutual resonance that kept me to keep exploring. Later last year, I just started mentioning casually in conversations with friends that I was interested in coaching.

And some of them were like, oh, I'm— what is that? I mean, oh, I've heard of some founder friends who have coaches. And like, they asked me if I would coach them. And I would just do— I did it for free for a few people. And looking back, like, I was not coaching. There's just— there's just conversations where I was trying to be helpful.

And, but I really enjoyed it. And so I guess the point is like, I just got into it without thinking too much about it. And then I also just started reaching out to coaches to understand more and more about what they would— what their work was like, what their days were like. And quite a few of those conversations at some point would turn into a bit of them coaching me. And then I, that's when I started to feel the value and the impact of what coaching can actually bring. I went on a retreat put on by two coaches in Boulder last November, and that was my first real experience where I'm like on this retreat for two days, we're spending the whole day together.

I'm actively getting coached by two different coaches. There's other people getting coached. I'm observing. And now I would say I'm just very focused on the apprenticeship with Steve, but also trying to spin up my own, start my own coaching practice. But like I said about, you know, we talk about thinking long-term and patience and commitment. I don't really feel like I'm rushing into it at all.

It's just one step at a time. But actually just yesterday, I heard back from someone who wants to work with me. So hopefully that'll be my first paid client, which I'm really excited about. And yeah, I'm not sure. I'm just trying to take it one step at a day. It's been a really fun journey so far.

[42:47] Paul: That's awesome. How did, how did the, how did you guys first connect on the apprenticeship?

[42:53] Matt Yao: I think it starts, it goes all the way back to last January where I wrote a blog called I Quit My Job and Stayed saw it and featured it in his newsletter. And I mean, I was following Steve. He probably didn't know who I was, but at that moment I was like, whoa, this is crazy. Steve, if he features it in his blog, that means he read it. And if he read it, he must have liked it at least a little bit to feature it. And so that was a big moment for me.

But then we didn't even talk until May and it was over Zoom. I remember I was in Tahoe and we, our Wi-Fi went out, so I drove to Starbucks, but then the Starbucks had really loud music. So I was just sitting outside a Starbucks talking to Steve for the first time. I was a little embarrassed about that. And then, yeah, I would just kind of spend the next few months exploring coaching. And then there was a lot of resistance and hesitation to reaching out to Steve, and I didn't reach out to him until October, until I was like, really felt like, oh, this is the right path.

I mean, it's kind of similar to what I said about spending 10 months trying to quit my job. It took another few months to really feel into coaching as a new path. And honestly, I didn't even reach out. I was like searching for the right moment when it felt right. And Steve's birthday is a day after mine. So I was like, oh, I have an excuse.

I can wish him happy birthday and ask him to chat again.

[44:21] Paul: I didn't know that.

[44:22] Matt Yao: Yeah. So nice. That's a, that's a bit of the story. And then we, and then we ended up meeting up in New York last year and I think things started picking up from there.

[44:31] Paul: We, we had, we had a breakfast and that lasted about 90 minutes and then we took an hour walk after that and Matt expressed a deep desire to, to learn alongside me and immediately I was receptive to the idea. I wasn't quite sure what it would look like, how it would be structured, but I said, yeah, this is a super interesting idea. Let's reconnect in the new year. It was December. And so of course, like, I get an email from Matt within the first few weeks of the new year. And yeah, one thing led to another and now we're We're co-collaborators.

Yeah. And what is the, what's the structure of that look like? I think, I mean, as somebody that has been very independent for almost 7 years now, I sort of have this like, oh, it'd be nice to work with people, but it never really goes past that. So how are you thinking about this? I think, I mean, one of the challenges is a lot of people on independent paths and working as solopreneurs are not optimizing for money. And if you bring in other people, it sort of like puts more pressure on the system.

But yeah, I'd love to hear what, how you're thinking about that. Any of the money setups and things like that. Yeah. Well, I think to start, what's interesting is when we initially started talking about an apprenticeship downshift, the decelerator program was not in view. That did not exist yet. And so, at first we're like, okay, what does this look like?

And then once that became very clear, I said, hey, what does it look like for you to potentially support me on this project as you have time? And Matt would obviously, well, not obviously, but express a desire to help any way he can. And that in return, I will coach, mentor, teach you And that's ultimately what it is. And what we said is, hey, let's view this as an experiment. Let's plan to energetically commit for 3 months and let's just take it day by day, week by week. And at any time we can decide that this is not a fit.

And so at a minimum, we meet every week for an hour on Fridays. That said, what I'm noticing is that we're texting, I mean, multiple times a day. He's been helping me with Downshift. And it's just becoming this like fluid mentor-mentee relationship that includes learning resources, helping him think through his practice. I've opened up the kimono and given him my one-pager and templates. Soon, you know, if, you know, be able to plug into the infrastructure.

That I have, all for nothing other than, you know, because I'm a good guy. The other thing is Matt offered to do it for free. And I was like, at a certain point, I can't just like accept that because you're going to be contributing in different ways. And yes, I'm going to be investing a lot of my time in your development and giving you a lot in terms of resources and infrastructure. But like you need to get paid. And so the way that we structured it was, um, basically a $1,000 monthly stipend, um, for help.

And as Downshift launches, we're going to do some sort of a profit share, um, of that program so that he feels like he's being compensated for his efforts on that. That's great. Yeah. And sometimes free is too expensive, like it— one, you might just have to go make money. So like you're going to go work on something else. But yeah, I think involving money in these things is, is very important.

I, I think, Matt, you are so good at reaching out to people, asking for advice, but also being somebody that adds to what people need help with as well. How, how do you think about that? Because I get approached by a decent amount of people and a lot of people sort of want me to like create jobs for themselves. They'll be like, hey, do you have any work for me to do? Or, hey, I'm looking to do any— some projects. Do you have any ideas?

And it's like, I don't really have the bandwidth or the time, especially with a young daughter now, to think about these things. Um, but I, I sense you're really good at this, Matt. How, how do you think about time and sort of, uh, putting yourself in a place where it's easy to help you?

[49:33] Matt Yao: I don't know if I can answer, I don't, I don't know if I can help you in your situation with people asking to help you, but I can definitely answer the question. I didn't realize you could just, like, I started my sabbatical when I started to learn how to use the internet again. With like Twitter and stuff. And I didn't realize you could just reach out to people and ask for a conversation without trying to sell them on anything or ask them to mentor you until like people started hitting me up. It was like the other way around first. So people would hit me up to chat about sabbaticals and my experience, and I was always super eager and excited to chat with them.

I was, you know, I didn't have a job, I had free time. And in the beginning, like, these are just people that, you know, just might be a regular, a regular person just has a Twitter where they're a lurker or not posting. But I think there was a couple of times where people, there was a few cases where people reached out to me and I knew that I would have been excited to reach out to them to chat, but I just didn't know you could do that. I was like scared of reaching out to people. And so I think that's how I learned when it started happening the other way around. And since then, I think it's just been a matter of following my genuine curiosity, always going in to learn.

But I'm also very— I don't reach out to that many people. I just sort of like am patient and consume what they write and their ideas. And so that way, by the time I actually send them a message, I just— there's no like secondary ulterior motives. I'm just like genuinely curious to chat with them and Usually I've already like read a bunch of stuff. I come in with questions, I'm ready to go. I don't know about your situation.

I'm not sure how to help you there.

[51:24] Paul: No, it's not about helping. I think it's about making visible how thoughtful you are in the approach. I think if somebody— I do the same thing. If somebody has tons of writing on the internet, just go read it. You can like, one, solve a lot of the questions you have. And then two, you have more context to sort of form a relationship based on that stuff anyway.

And yeah, you just stand out for somebody that actually does that versus I think a lot of people don't put in the time. Like I get messages, it's like, hey, Paul, would love to jump on a coffee chat sometime. Can you send me your availability? Right. And so you're actually spending hours reading stuff and then sending a very specific, thoughtful message about something you're struggling with. And to a writer, if you share something you're specifically struggling with and trying to work through, a writer is like, oh wow, this would be interesting.

I can like think through my own thinking and test my ideas. Yeah. So yeah, maybe, maybe you just didn't realize you were doing some of that stuff compared to other people. Yeah. And I'd love to hear follow up on something we were touching on earlier, Matt. Like, you're still— I think you're still in your 20s, right?

[52:45] Matt Yao: Yeah, I'm 27.

[52:47] Paul: How does it feel to be working on a decelerator versus like the messages of our culture are like capture as many gains as possible in your 20s. Like you should be crushing it. You should be like building your bank account, especially in the tech community where like software engineer and product salaries have skyrocketed so much.

[53:08] Matt Yao: Yeah. It's interesting. Steve mentioned that, you know, Downshift is, is his, you know, his brainchild. Frankly, I don't really know what the apprenticeship would be like if Downshift wasn't here. I don't know what, you know, I don't know if there'd be enough enough help or work. But I've been thinking a lot about my relationship to Downshift and how, you know, my friend Jake, who I met through Twitter, he said, if you like pick the right mentor, the tasks will naturally feel like aligned to you.

I think that's very true. Like an apprenticeship, the biggest difference with a normal job is like it's a very people-first orientation. So instead of like finding the company or the role or the compensation, that you want. You just find the right person that you want to spend time with and learn from. And then like, honestly, the work that I've been doing, it's varied a lot. Like sometimes it's website stuff, sometimes it's writing, editing.

So it keeps changing. And, I lost my train of thought. What was the original question?

[54:10] Paul: I mean, you can, you can keep going with that. It was basically around Um, yeah, I mean, just keep going with that. I'm curious.

[54:20] Matt Yao: Oh, oh, downshift, downshift. Um, in my 20s with downshift, I actually feel like it's, it's not an opposing force to ambition and wanting success and achievement. Like, yeah, I view myself as a very Type A ambitious person. Like, I want to be successful. I want to have a family one day, but I also see examples of where downshifting and prioritizing rest, stillness is actually required to be at the top of your game, to be an elite performer. Like, you just look at it in athletics right now, you see all of this recovery gear.

You see, you know, 20 years ago you would never see an NFL team doing yoga together, and now they do it like once a week. You see LeBron James with these like NormaTec leg sleeves, like none of that existed. And now you see it in professional athletics. They are prioritizing rest and recovery just as much as like the actual training and practices. And I kind of view it the same way where like knowledge workers, we're just sitting behind a desk, we're always on, like we, we need just as much of that perspective and prioritization. Of like downshifting in our lives.

And I'm also just inspired by athletics. Like, I ran a marathon last year. I'm recovering from a broken ankle. I'm like trying to be patient but very eager to just get back into it. I, you know, I very much have like very ambitious goals and I also value downshifting. I think the two can coexist.

[55:59] Paul: Yeah, that's beautiful. It's, it's so interesting. I mean, if you just take a huge step back, and look at the way we work, it's basically designed around running machines, right? And the best way to run machines is just to run them continuously, right? And but that is sort of crazy for creative work. If you look throughout history, like all these creative people had periods of ups and downs and all sorts of intense periods followed by slow periods.

And ambition has been such a journey. For me too. I, I would like really struggled with this after quitting my job. I sort of had this self-narrative of like, I'm just going to like become a bum now. Like, I'm not ambitious, ambitious. I'm not like those people.

But the truth was like I had been recovering from a health crisis for years and literally didn't have the energy to work at a consistent 5 days a week, 40 to 60 hours continuous work years. And it, it's much easier now for me to sort of like take a week off at a time if I need it, take a day off when I do need it. And I either am dealing with some ongoing health issues or things like that. And a couple years ago, somebody said to me, Paul, you're one of the most ambitious people I've met. And it like broke my brain. I was like, what are you talking about?

I like hardly work. But I had equated effort, like constant high-intense effort with ambition. And I know you've written about this as well. I love your post on ambition, Steve. Thanks. It sounds like you've gone through a similar journey there too, realizing, oh, maybe I can be ambitious on this slower path.

Yeah. Yeah. And I think back to this conversation that I wrote about in that specific piece with a very dear friend, Jonathan Basker, and he and I were sitting in Madison Square Park on literally a picturesque fall evening. And he said, I always thought I wasn't ambitious until I realized my ambition was to have a good life. And in that moment, it like hit me, but right between the eyes. And for me, that's the thing that, that's why we're all doing this is like we want to have a good life.

And what we can be ambitious about can vary. It just doesn't have to be about work. And it doesn't just have to be about always on, always going. That there's different ways to have a relationship with this word ambitious or ambition. And yeah, it's something that I think a lot about. And what I'm realizing through coming out on this multi-year journey into really discovering what I'm meant to do is like, I've never been more ambitious in my life.

And I believe that I'm, I'm going to have a significant impact. And I'm working no more than 40 hours a week because, you know, my ambition is to have a good life that's multidimensional where I can be there for my kids, provide for my family, take care of my body. And I know that if I try to effort too much and go to 60, 70 hours a week, I'm just going to break down. Like this human body isn't meant to just go into perpetuity forever. And the last thing I want to say, which I think piggybacks off of this idea of constant efforting and what Matt said about athletics is like, just look at nature. I think there's so much we can learn from nature is that we are embedded in cycles and There are moments where there is growth and there are moments when that growth gets cleared away for new moments of growth.

And so I think that there's a lot we can learn and there's a lot of intelligence just by observing the cyclicality of nature and life. We're not meant to just go forever. Yeah. I mean, I think that resonates so deeply and I think that's why we're all friends on this journey. But it's radical compared to what most of our peers and former peers think. The revealed preference of most people I see is that money and career success is more important than those things.

I'd love to hear about some of the explicit trade-offs you've had to make and what are the costs financially, status-wise? And I'm guessing based on my own journey that some of those became costs you were happy to pay. Yeah. Well, the reality is, is if I wanted to grind more, go faster, I could no question make more money. If I coach, there's a certain amount of hours in the day, there's a certain amount of rate that I charge. and I know that I would be unhappy.

I know that I wouldn't have time for writing and learning and creating these other things, and I'm unwilling to sacrifice that time for more money because as I learned when I was an investor, more money doesn't mean anything. Like every incremental dollar doesn't dramatically increase my happiness. It just doesn't. And I figured that out about 5 years ago. And so I can step into this life that I have now, knowing that it's just not fundamentally going to change my happiness and my fulfillment. And so I want to spend my time focused on the things that really do, that ground me, that provide meaning and fulfillment, time in nature, creating, being with my girls, spending time with my wife, cooking, cycling, coaching.

Coaching does provide a lot of meaning for me, but I'm unwilling to sacrifice anything else. The other thing I would say is I don't really think anymore about what other people think of me and my old colleagues. In fact, I like to say I think that there's a part of them that's envious that I was able to get out when I did because venture cycles are long, 10 to 15 year cycles. And if you have your own fund, you've raised money from, it's very hard to get out. And I realized that I could get out right at the right time. Yeah.

What, how do you and your wife think about this? Like what, it seems like she's been pretty supportive, but what are the conversations you're you're having with her about these trade-offs and how you both spend your time on work and family and all this? It's a constant balance. I'm married— for those in the audience, I'm married to an entrepreneur. She is the founder and CEO of a company called The Sill, and it's a constant balance. I mean, the reality is, is when Eliza and I got together, she made it very clear that she also wanted to have a career.

[01:03:48] Matt Yao: Career.

[01:03:48] Paul: And that was very important to me. She didn't want to be a stay-at-home mom and take care of the kids. And so from the very early days, including now, we've chosen to be 50-50 partners as much as that can possibly be with, with kids. And so, you know, neither one of us gets to put our career in front of the other person. And so As a result of that, we both have to make it work, right? So if our kids are sick and they can't go to school and we don't have childcare, it's not, oh, you watch the kids, I'm going to go work.

We're both, we're working together as a team to navigate these situations. And so as a result of that philosophy, inevitably, it comes from a place of support and wanting what's best. And so the question isn't, isn't how do we make this work? It's how do we do what's best for the family in the context of us being partners? And what, to my wife's credit, you know, she's like, we don't, we don't need, like, I remember like maybe 2 years ago, I was like, what if I built a coaching practice that could do $1 million a year? She's like, Steve, We don't need, like, no, like, and so it's great that she's at times can also be this like counterforce to my overt ambitious or ambition to be like, hey, like, that's not what really matters to us.

And so I'm lucky to have an amazing partner. And I should also say, like, when I was going through that transition of leaving venture, she was the one that was fully supportive of that move. And she said, afterwards, you're a different person. You haven't complained about work since you left investing. I used to complain about investing every single day. I don't complain about work anymore.

It just stopped happening. That's so beautiful. Yeah, I think the role of supportive partners is so important. Like, what gives me so much confidence is Angie's support of my journey. And she's always just sort of like noticing when my energy's off and is like, you don't have to do this. We can live a simpler life.

We'll figure it out. And I think that's the thing that a lot of people don't see behind the scenes of like sort of having someone on the same page, saying, playing the same game and And yeah, it's really cool to see when people have that alignment. It's beautiful that you shared that example with Angie. And Eliza says the same thing. And what I think about is that, you know, instinctively inside of me, I have this like provider mentality, I think largely stemming from observing my mother working two jobs and having to provide. But what Eliza always, even though I like emotionally and instinctually, I have this this tendency to like that provider tendency is she's again, like reminds me, Steve, we're in this together.

You don't have to shudder or carry that load all on your shoulders. And so having a partner to help and seeing it as a portfolio versus, you know, versus just one person having to carry the load. Yeah. How do you think about this stuff, Matt? I know you're not married yet, But you said before you want to have kids. How are you thinking about this path as sort of like setting you up to have a family in the future?

[01:07:40] Matt Yao: Yeah. Well, I'm 27 now. Hope to start a family next several years. So I have a few years. I think seeing guys like, like the two of you helps because I see how, you know, I finally took the advice or it's finally internalized the idea that like once you become a parent, you have a lot less time. And I think like at least 10 people told— Yeah, but I mean, the first 10 times I heard it, it just like went in one ear and out the other.

I didn't really understand it. I was like, what do you mean? Like the kid just sleeps all day. Like I'll be able to surf all day still and ski all day. And so I finally realized that. And so I'm kind of like viewing the next few years as when I really take advantage of not having a family and really dedicating a lot of time to my career.

I mean, I'm at the very beginning of it. And by that, by the time I'm ready to have a family, I hope to be in like similar position as the two of you where I'm able to like have flexibility around my days. Be there for the kids when they're young, all that. And right now I have a girlfriend, she's in medical school. And actually, I think it really, it's really interesting how we're both like kind of at the same part of the, of our respective paths where we're both broke, we're both like learning. She's kind of doing her own version of an apprenticeship where it's like in a much more defined and rigid way, but like, I think it certainly does help to have someone there that doesn't require me to make a certain amount of money and is perfectly fine and sees, has a similar view of like a long-term horizon.

And in medical, in the medical path, you're basically in school for like 10, 12 years before you actually are a real doctor. And so I think she, it's really, really brings me a sense of like groundedness when I, when I talk to her about these things and there's not like this other, other, there's not these other voices telling me that I need to go get a job or I need to start making money or, you know, you know, fancy things like that. It's been great.

[01:09:57] Paul: Yeah, I think you're in a good place. I think I've seen so many people on unconventional paths and The most important thing is are they interested in stuff and are they willing to try stuff? And like, if you have that, you will literally like not fail. And like, I think the way you're approaching it is beautiful because I worked for 10 years and the first 3 years of working on my own were so hard emotionally and personally. And I had to go so slow because I had to use time on myself. I had to get to know myself again.

I had to like actually build the actual confidence of doing things I cared about. And yeah, this is why, like, I wish I left my path earlier and poor because I would have been able to invest in like developing that energy. Right. And this is sort of a tangent, but I'd love to hear— you've written some really interesting stuff about money, Matt, and how you're thinking about money and how that reframed for you totally after taking your leap. So I'd love to hear a bit about that and then maybe some of Steve's relationship with money as well.

[01:11:19] Matt Yao: Yeah, I'll touch on my relationship with money in two examples. First example is skiing. Like, I love skiing. I broke my ankle skiing 5 weeks ago, so that threw a bit of a twist into this year. But I'm, I mean, I'm used to skiing like 60 days a season. I'm— the last 4 years I've like literally lived right by the ski resort.

And it's such a— if you, if anyone has skied, they know the difference between skiing on a weekday without any lines versus a weekend trip. Tahoe, where you're stuck in traffic on the highways, you're stuck in lift lines, but also the magical ability to configure your entire schedule around the weather. So when there's a fresh storm that brings in a bunch of powder, you can go ski that. And that was just the game changer that I first experienced during COVID And with money, it's like I've— skiing is pretty much a non-negotiable for me. Like, I— it's part of— it's part of who I am, and I've been able to make it work even though I've been living off of savings for over a year. And some of the changes I've made are basically like, I buy one season pass instead of getting all of them.

I'm not trying to take a ski trip to Japan or Europe, even though that's something that's on my bucket list. And I don't, I never spend any money at the ski resort. Like I bought the season pass up front. I drive there, I ski, I ski until I'm, I'm ready to go. I go home. I'm not spending like $25 on chicken fingers.

You know, I keep it down to the essence. The essence of skiing is just skiing. It's not like any of the après-ski, any of the drinking outside after. It's just like the pure skiing. So that's one story. The second story is I basically— I'm home right now and I'm eating my mom's cooking, which is great.

But when I'm living in New York or skiing, I basically just eat the same thing every day for lunch, which is a big bowl of oatmeal. It's got like 12 ingredients and I put protein powder in it. It's like super healthy and really cheap. And I think I came to that because of this like forced frugality, but I've come to like view it as an amazing thing where I don't have to think about it. I know it's really good for me, tastes great, and it's like, I think you can find those like win-wins in, in your life when it comes to money where I don't really feel like I'm suffering at all. Even though I'm living off savings.

And I, I eat this delicious bowl of oatmeal every day and it keeps me healthy, keeps me fueled up. So yeah, those are just two examples of my relationship with money, skiing and oatmeal.

[01:13:48] Paul: Yeah. And that second one is such a stark contrast to what you were describing at the beginning of the episode, which was this like very cynical, like buy whatever, like never think about money in Hawaii. It sounds like it's just a completely different energy.

[01:14:04] Matt Yao: Yeah, I, before I left my, my job, I went on a work trip to Australia and I was, I mean, I guess you can buy groceries when you're on a, on a business trip, you can still expense it, but I was just, it's just harder to cook in a hotel room and all that stuff. I was just expensing every single meal. I would Google best restaurants in Sydney, best restaurants in Melbourne. I would go to them. The first few meals were amazing. I was taking photos, sending it to friends.

you know, these are like on the top whatever list for, for restaurants. But like the second half of the trip, I was just kind of sick of it. And like, yeah, if I had that oatmeal on that second half of the trip, I probably would've been a happier person.

[01:14:44] Paul: That's beautiful. Yeah. How has your relationship with money changed, Steve? I mean, you were explicitly trying to make as much money as possible. That's sort of the implied assumption of venture. Yeah.

Yeah. And I think there's an implied assumption or story I tell myself is there's an applied assumption externally that I had made all my money and retired to become a coach. And that is further from the truth. Couldn't be further from the truth. I walked away before I had made my real money. And that's what made the decision very challenging.

But what I ultimately decided, and my wife reminds me this all the time, 'Cause I didn't grow up with a whole lot of money, right? And my mother, you know, living, my mother always said, we're living paycheck to paycheck. But my wife reminds me, she said, well, how was your childhood? And I said, on the whole, like pretty awesome, right? And so I always have to remind myself that what I have right now is pretty amazing. And I don't need all the extras, like, you know, like super fancy hotel, like all the incremental things that more money would give me.

It just doesn't increase my satisfaction and fulfillment and happiness. And so for me, my relationship with money has changed where like, I like nice things, but I don't need a whole lot of them. And like, like at the end of the day, like the things that really matter to me is like time with my girls, time in nature, helping, creativity, like things that like are free, like that you don't actually need to spend money on. And so for me, that's just how I've chosen to reorient my life. Now that said, like, because I don't have FU money, because I didn't walk out of venture with like a, you know, a vault full of cash. Like, you know, I have to budget, I have to save, like I have to do all these things that are just, I think, wise choices.

But like, yeah, I think life is about making trade-offs. And the thing that I'm unwilling to sacrifice is that happiness, is that freedom, is that flexibility that I have. Like, I'm just not going to go there because I know it just doesn't really change a whole lot. That's beautiful. Can either of you share a bit more about the decelerator and what that entails, the timelines? This episode should come out next week, so the 18th of March.

I think you're launching in April, but I would love to hear a bit more. Yeah. So think of Downshift as an 8-week Decelerator program. It's a journey whereby you and 12 others are going to go through this experience that sort of covers what I would say is 4 main phases. The first phase is what we call downshifting, which is really learning the art of downshift in the context of your conditioning and your patterning. The second is what we call descending, which is going inward to look at all the stories and scripts that you've been handed down related to achievement, money, work, and really start to understand that.

And then the third phase is what we call renewal, where it's really about stepping into your values, understand how to go and run measured experiments, a bunch of other things. And then finally, there's the integration phase of how do you integrate this all back into your life as, as a philosophy. And so across those 4 phases, that will be 8 weeks plus a 4-week integration process on the back end. And it's going to be a combination of an in-person retreat that we're going to kick off in the Hudson Valley. That's going to bring us all together, create a container. And then over the course of those 8 weeks following that will be a mix of lectures and group discussions on Tuesdays.

Thursdays, we'll have expert guest lecturers, some amazing folks like Jonny Miller, Andy Johns, Holly Whitaker, Benita Roy, and some others. And then there'll be a personalized coaching plan. So, Everyone will have an opportunity to work with me 4 times throughout the program where we're going to be looking at downshifting in the context of your life. And there's going to be a bunch of other great surprises. So that's an overview of it. Applications are open right now.

The response has been phenomenal. What else? Applications are due on Monday, April 1st. Admissions are rolling, though we plan to have the class finalized by Friday, April 5th, and the retreat kicks off in the Hudson Valley of New York on Wednesday, April 17th. And then the program goes to about mid-June. That's beautiful.

Yeah, I love the combo of in-person and virtual. I feel like that is such a promising space. Like, I'd love to do something in the future, but Count me in. My revealed preference is that I just wake up, sit at a computer, and either have conversations like this or write. So one day I will find the right time for that. But yeah.

And beautiful. Yeah. And as just as a quick aside, like as I've said to a lot of people, so the total experience is $6,000. We offer scholarships. And a lot of people have been coming to me and saying, oh, you've totally underpriced it. And I think this is sort of a meta theme across what we're trying to accomplish, where if we're taking a very long-term view on this, we're not here to optimize and to make every last dollar.

Like our objective here is to learn, experiment, have fun and be of service. And that's what we're trying to do here. And yeah, we're super excited about it. Fantastic. Where can people learn more about your stuff, Matt?

[01:21:37] Matt Yao: Wow. I've never been asked that question. Twitter. I don't have the best handle. It's @Matt_Yao. And oh, my blog, Game of One.

Substack.com. Oh, actually it's blog, blog.mattyao.co. I recently bought the domain, so you can check me out there.

[01:21:58] Paul: Very cool. Anywhere else you want to point people, Steve? Uh, you can, yeah, yeah. It's schlaaf.co, S-C-H-L-A-F.co. And you can learn more about Downshift at downshift.me. Fantastic.

Well, thank you both for the beautiful conversation today. I am excited to learn from your apprenticeship and hopefully your continued writing. The both of you, really appreciate you guys and thank you so much. Thanks, Matt. You've been a big inspiration, so really appreciate having this conversation.

[01:22:37] Matt Yao: Great.