Matt Yao: Embracing Uncertainty in Work and Life

I recently recorded my first podcast, featuring

Matt Yao

as my guest. Below, I am including the video, the podcast description (including timestamps), and a transcript. For those who want the audio, you can find it on Spotify here. I plan to record more of these in the future. Areas of interest include investing, pathless path/creators, entrepreneurs, etc. Let me know if there is anyone you think would be a good guest.

Matt's bio: "As a coach, I guide ambitious professionals to cultivate human agency and self-awareness. I also write ⁠More Human Possible⁠, my blog that explores the inner and outer worlds of being human."

Matt's coaching site: ⁠https://mattyao.co/⁠

Timestamps

0:00:00 Bryan discusses leaving his job and exploring different opportunities.

0:00:57 Bryan talks about his newsletter and content creation goals.

0:03:07 Matt shares his recent move to Palo Alto and looking for new opportunities.

0:05:14 Bryan asks Matt about balancing focus and diverse interests.

0:06:20 Matt offers advice for a first-time podcaster: enjoy the process.

0:07:51 Matt discusses the idea of a portfolio career and not being meant for one job.

0:10:48 Bryan expresses his fear of missing out by not going "all in" on one thing.

0:11:56 Matt suggests that focus and multiple interests can coexist by eliminating wasted time.

0:24:49 Bryan discusses navigating career opportunities while maintaining his passion for writing.

0:31:05 Matt mentions the attention economy and honoring the reader's attention.

0:45:47 Matt reveals his potential niche for coaching: people considering quitting their jobs.

0:57:37 Bryan asks Matt about his work with clients on tech addiction.

…

Bryan Wagman: Yeah, so basically, just to kind of jog your memory, I left my job back in March, and so my last day was March 19th. And I still don't really fully know what I want to do, but I'm looking at a consulting opportunity, so that'll be a month-to-month, independent contractor type setup. So, waiting to get approval for that from the guy's boss, basically. And hopefully, that'll pan out. And if so, it'll be, a fully remote opportunity, and just kinda take it one month at a time and see if it works for both of us. So, but there's been, a lot of exploring over the course of the last few months and trying to figure out what I want to do with my life. And I still haven't really figured that out. I looked a lot into entrepreneurship through acquisition and things like that, and potential, other jobs to go to, whether remote data analyst type stuff, things like that. And I'm trying to write a newsletter. That's kind of my main thing. I wanna write an investment Substack. And so I'll be working on that, trying to do two write-ups a month, though when I start this contracting thing that might shift to maybe, once a month. But just trying to, write that newsletter and try different mediums, like podcasting and things like that to see kind of what works the best for me in terms of just putting content out there that hopefully some people want to pay for someday.

Matt Yao: What's the, what do you mean by trying to write a Substack?

Bryan Wagman: Well, I mean, I guess I've been doing it. I've been doing it for probably about two months now or so. I think I've written three or four posts, shooting for a once every two weeks cadence.

Matt Yao: Okay. So you have stuff published. You are doing.

Bryan Wagman: Yeah.

Matt Yao: Yeah. Okay, cool.

Bryan Wagman: Yeah, I've got, I guess the trying part is trying to make a living off of it, 'cause I'm not charging for it or anything.

Matt Yao: Yeah, that's tough.

Bryan Wagman: Yeah, right now, I've got 400 something free subscribers.

Matt Yao: That's a lot. How'd you get so many?

Bryan Wagman: Well, again, those are all free. But I started publishing on there back in 2020, and so most of them are from kind of the early days where, Twitter wasn't nerfing the Substack links and stuff like that, and I got a lot of followers on Twitter, it's 10,000 now. I forget what it was back then, but it used to be, I'd publish whatever, and I get 20 or 30 subs every time, and now it's I'll publish a super in-depth write-up, and I'm lucky if I get a couple. So I don't know how much I want to, let the, let the market dictate what I write about, so to speak, versus just writing about stuff I like. So that's all part of the journey to be figured out over time. But just want to focus on making sure that I'm actually producing the writing and publishing every so often. That's, that's my main focus and priority right now.

Matt Yao: Sweet.

Bryan Wagman: Yeah. Boy. How about you? Palo Alto, right?

Matt Yao: Yeah. I moved to Palo Alto three weeks ago. Feel the big change has been starting to look for new opportunities. I'm still coaching. I'm still very happy coaching. And I also want to have a little bit more stability financially. And I also just have a lot of interest outside of coaching. It's, I'm certainly going deeper with my coaching practice. I'm in a therapy training. Spend a lot of time with that, this weekend it's gonna be Friday, Saturday, Sunday, six to seven hours of Zoom all three days. So, it's not I'm trying to. It's interesting, usually, you see, "Oh, I stop one thing, I go to the next," and it's usually an all-or-nothing type approach. I haven't seen too many people do this type of thing that I'm doing, which is kind of going back full circle, or I don't know what I'll end up being but integrating this sort of past, and then the new thing, trying to make a life where it's more of a portfolio. There's different elements of work. So that's definitely the main thing right now, and then also, just getting settled in, finding a new, establishing a new routine, creating a sense of community. It is. Yeah. I think I took it for granted when I was moving around a lot. But once you actually are in a new place, there's a lot of things to get used to, and I'm in an area that I don't know too many people yet, but I'm starting to, meet new people, starting to get introduced by mutual friends and stuff. So, things are in motion.

Bryan Wagman: Yeah, yeah, that's good, man. You mentioned the portfolio thing, that was actually something I wanted to ask you about. Because I'm curious, because I know, even back when you were doing your sabbatical, you had, a blog, and doing climate writing, and a sublet service, and then the podcast. So how do you think about the tradeoffs between, because I'm trying to figure this out, too, between, different mediums that I can spend time on, and spending time on Substack and, and looking for things to generate income and things like that. So I'm curious what, what you think about kind of the tradeoff between focus and 'cause sometimes I think, "Oh, well, if I go all in on, XYZ, whatever it is, I'll probably get more results from that." But there's so many different things I want to do.

Matt Yao: Yeah, are we starting? Now, this is the podcast part.

Bryan Wagman: Yeah, sure. I don't know. I'll probably, I'll probably edit some of it, some of it out, back and forth. But honestly, just with the podcast, I don't know. I don't know what I'm doing. I haven't done this before.

Matt Yao: First episode, right?

Bryan Wagman: First episode. I've never recorded either as a guest or as a host on any other one. So, I don't know if I'm gonna make this into a written interview thing, or, or just publish the audio, or the video, or, or all the above, so. And I'm open to suggestions, and, kind of ideas and advice. I don't know if you have any advice for a, for a first-time podcaster.

Matt Yao: Advice? Just try to enjoy it as much as possible. That will, that is what will keep you going, and if you stop, it'll be, it'll be because you stopped enjoying it.

Bryan Wagman: Hmm.

Matt Yao: But anyways, let me answer your question, 'cause I think it's a good question. So I actually had this, I'm constantly thinking of new ideas, or just thoughts come to me. And this thought came to me today of, sometimes I think in terms of blog titles, phrases will come to me, and I'll be, "Oh, that could be a blog title," and it's something the phrase, it was, "simple life, complex work." And it captures what I'm trying, how I'm trying to live my life, which is. And also, life and work are not two separate things. Life is the big thing. Work is nested within it. But I just mean, outside of work, I want my life to feel really simple. I want to have, a few close relationships, my partner, few close friends. I want it to be simple and there's a sense of routine. There's a sense of ritual. I'm not always moving around anymore. I eat a lot of the same meals that, I like that taste good, are healthy, et cetera. And there's, also I'm spending a lot of time not on screens, outside of work. Moving my body a lot, doing a lot of things that people did a hundred years ago.

Bryan Wagman: Hmm.

Matt Yao: Playing sports, working out, hiking, being in nature, all that thing, all that stuff. And then I think, when it comes to work, I am probably firmly in the camp of being okay with multiple things. The, I think the phrase portfolio career is the most popular or legible phrase of what we're talking about here. I like it, but I also have a different expression. I just called it elemental work or an elemental career, where you can think of, I got this inspiration when I was watching Avatar. So it was, earth, fire, water, air. Each of the elements kind of has a different thing, and there's not one that's better than the other. But anyways, I think it's just natural. We're not meant to do one job. We're not meant to have one interest. Many of us have multiple interests. And so, if you sort of relax your, if you sort of relax the rigidness on the definition of work, then to me it's just, work could be a set of things that you're intellectually curious about. It could also be things that make you money. But those don't have to be, it's not an and statement. It's not it has to be something you're curious about and make money. It could be one or the other, or some subset. So, I think for this question, it's really important to understand, where's the question coming from? Is it coming from, how can a person structure their work and their career for maximum fulfillment, curiosity, flow, et cetera? Or is it from a question of how to make a living and maximize income? And I think the answer can vary a lot. If you're, if you're trying to maximize your income, it's actually not always the case that you should focus on one thing, because the one thing that you're focusing on right now might not actually be the thing that you could do. It could just be the new, the, the new thing that you haven't tried yet might be the thing that is actually more lucrative for you. But in a, we don't think that way. We think logically, straightforwardly. We try to collapse uncertainty, understand what the future is gonna hold. So that's why a lot of people end up climbing the corporate ladder and staying in one industry. But I think what I'm more familiar with is just what to do, how to approach life in a way where you're able to pursue your curiosity, follow your interests, feel you're being creative. And in that way, in that sense, I think you, you have to structure your work for the sort of natural, unfolding, it would look more like a slime mold, or a bacteria growing into its environment, in all these different nooks and crannies, and all these shapes, rather than a perfectly planned city grid.

Bryan Wagman: Yeah. Yeah, I think for me intellectually, I kind of like the idea of being able to throw a bunch of stuff at the wall and see what sticks, and maybe get more focused over time. But at the same time, I think I have a little bit of FOMO, especially because, I don't know if this is kind of a meme, so to speak, or a hustle culture type thing. But when you, when you hear a lot about, what I would say, entrepreneurs, athletes, musicians, people that attribute their success to a lot of times. They talk about the level of focus, and the dedication to the game or the company. But I mean, and maybe that's different for, people who want to do that, who want to be, the very best in the world at activity XYZ. Maybe that demands more hours and more percentage of your time focused on it. But, but there's still kind of that, that pull for me of feeling if I don't go all out on something, what's, what's the point? It's kind of scared to let go.

Matt Yao: Yeah, I think doing multiple things and focus can actually coexist very beautifully. It just isn't intuitive. What I mean by that is, as a thought exercise, if you cut out all of the ways you're wasting out time, wasting time, that you know it's, it's you that is saying that this is. This is how I'm wasting my time, not, not me or someone else saying this, this is a waste of time. You'd probably be left with, a lot of extra time to do stuff. And so for me, even though I'm someone who has had multiple interests and still has multiple interests, I still waste time. I still watch YouTube videos. I still, go on social media, or sometimes it's a little bit more subtle. I'm just reading certain Substacks that I don't get value from anymore. So if you subtract all the ways you're wasting time, and then you pay attention to your, your state, your energy state, how alert are you? And you're working when, when you are actually able to get things done, and not trying to grind at midnight where your brain's not working anymore. You can get huge improvement just in that. But I also think around these stories, right? These stories of obsession and focus. The ones that, the ones that make it to, so popular, stories are the rare ones where it was, "Oh, from Tiger Woods, right? From age two, he was golfing, and then it was relentlessly obsessed." But there's this other example, this is from this book Range by David Epstein. What's the, who's the, the really famous tennis player?

Bryan Wagman: Nadal.

Matt Yao: The other one. No, it might have been Nadal. He didn't start playing tennis until 10 or 12 years old, and but he was really gifted in a lot of other sports, and his parents were supportive of him trying other sports. So it was a question of, "Well, okay, I think there was a mistake of, these people were the success stories, they focus, so I have to focus," 'cause you don't know if you're gonna be, you might be a success story from focusing, choosing to focus on, on something later. So you might have five different things right now, and it's only because you allowed yourself to explore five things at once, and naturally prune the ones that you're less excited about, that maybe one, three years from now you're, "Oh, this is the thing, and I'm gonna go all out at it." And then that's the thing that ends up being what you're known for.

Bryan Wagman: Yeah. But for me, over the, over the course of these past few months, I think I can definitely relate to the reading a lot of Substacks, things sometimes I'll, I'll sit down, specifically to try to spend an hour or half hour, or whatever, catching up on all my email and stuff. And then there'll be these Substacks, and I'm, I kind of want to read that, but not really. And then I end up spending, 15 minutes reading it, or whatever, and, and that throws off the whole point of, I sat down to get through my email. And, and now I'm not doing it. And so I'm trying to do a better job of kind of just capturing and dispositioning stuff appropriately, but it can be tough to, to let that stuff go. And it's weird, because, in some ways I feel it's, it's similar emotionally for me to the feeling I get when I really want to check my phone or something. I want to, compulsively check my email or my social media to see if anyone's liked my tweets or anything. It's, "What if there's something good in this Substack that, that I don't wanna miss?" But at the same time, it's, even if I were to boil down my life to, try to say five really big projects or big ideas, big things that I'm working on, 90% of the stuff I spend time consuming does not relate to any of them. And so, I'm still sort of interested in, in small business acquisition. And I wanna kinda keep tabs on how things are developing in that space, whether it's, from a legal perspective or just different people to follow and connect with, but one that I've kind of ditched recently is, I was gonna try to do some e-commerce stuff, sell, maybe either yoga mats or, or pickleball paddles with Bible verses on them, or Christian art, or something. And so I kind of ran some ads on Pinterest to test some different designs. But then I kind of narrowed it down. And I was, "Oh, well, I need to really focus on, on this newsletter. So I'm just going to drop that." But it keeps kind of, it's still there in the back of my head, as something I want to try, and I feel maybe I was, cutting it unnecessarily, just again. Kind of this fear of, "Oh, well, if I don't focus on, if I divide my attention between these two things, neither one of them will work, will work out." But that's kind of, not, I don't know how to explain or articulate it, but I don't feel that's actually necessarily the truth in terms of, especially given how early on I, I am in both of them. But I found that, yeah, difficult.

Matt Yao: Yeah. My sense is that you're maybe looking for the feedback loop. The, the measurement on your feedback loop is, is something that is not perfectly calibrated to your own intrinsic. Your own intrinsic judgment of, "Oh, I just like doing this." Maybe you're looking for, people that are interested in buying it, right? So I think it's important to separate, what's for money and what's for just for the sake of it. And it's okay if those blend later on. But at this, at the start, at the starting point, at the trailhead, being really clear, "Oh, am I trying to do this e-commerce thing because I need to make money, or am I just really interested in e-commerce and Christian pickleball paddles?" And what was I gonna say? Oh, the other thing I was gonna say is, this, this topic of FOMO, and, "What if? What if..." I find for myself that it, I hear that chatter a lot less when I'm finding a lot of satisfaction in the other things I'm choosing to do. So, what I mean by is, it's all tradeoffs. Right? So, "Oh, I choose to, I, I chose to stop doing a podcast with a friend. I chose to stop writing my climate newsletter, chose to stop doing this subletting newsletter." And it's not always, "Oh, I feel great now that I did it," but it's always. What always helps is, what I'm choosing to focus my time on instead feels good. And when I am feeling of feeling torn, sort of pulled away from my present experience, there's, it's usually a sign, there's some emotion here that's causing the stuckness. And then another more tactical thing that happens is, it just means I need to focus on the actual things that I'm, that I'm choosing to do. So, for example, I found when I took a six-week break from writing my blog recently, from mid-May to early July, "Oh, I had all these thoughts of, I'm getting kind of spirally." And, and then I just sat down and wrote, and then, now I'm back in the flow.

Bryan Wagman: Hmm.

Matt Yao: And I'm from, I'm trying to write. Well, I'm, I have all these topics to write about. I'm really focusing on it. I'm making sure I feel good about it before I publish it. And I'm, I'm being very focused on that. I'm being very focused on the present.

Bryan Wagman: Yeah. Yeah, the, the money thing is, is interesting. I feel the e-commerce thing is probably more about money for me at this point, because I think that's potentially a faster path to being able to get to a sustainable livable level of income versus writing a newsletter. And I may come to enjoy it more over time. I don't think I've done it enough to know for sure, but one of the things that you've written about along these lines is just kind of your recent transition with coaching, and how you're kind of starting to look for other forms of income right now. And you wrote something to the extent where it was, I think, I think you said something you kind of flip back and forth between not, on the one hand, wanting to just have blind hope that something's gonna show up, and, and on the other it's, grind, grind, grind, and really lock in and focus. And I'm, I'm curious, what would your life look like if you chose the latter? And if, and if you were, "I'm gonna go all in on this coaching stuff," what, what would you do? Differently, specifically, both with respect to your, your business and your life.

Matt Yao: Yeah, I mean, it's hard to say what would have happened. But I think, I'll probably tactically, what I would have done is just spent a lot more time on marketing, the coaching, reaching out. And, what's interesting is, I made this choice to start exploring new opportunities, and I don't know what it is gonna be that I land on yet. And as I do this, I actually am, in many ways doing all the things I'm about to say, right? I'm writing, writing a blog. One of the blog posts I'm gonna write about is very coaching related that might lead to more people hearing about my practice. I'm telling more people about my coaching practice. I, I just had a call today with someone who's starting her own coaching practice. So it's funny that, I took the, I intentionally didn't choose the grind-all-in path. And yet I'm still doing all the things that I would have done if I went all in. And I think maybe what I'm trying to say is, all in depends on, is it all in time? Yeah, I'm not doing all in time, but I am all in energetically on my coaching. I'm even if I get a full-time job, I'm still gonna coach. I had an interview last week for a founding PM role, and the founder was, "You can't. You can't have side, also, you can't coach if you." And then I was, on the spot, "I don't think this is a good fit, then." And so it's about being really clear about, what is we have? What is that? What am I moving towards? And it's a world where I'm still coaching. And what I tell myself is, actually taking off the financial pressure completely from coaching might actually, over the long run, end up helping me and being a more effective coach, because then I'm just, I'm just being there for the client, and I don't actually, if they need, if, if what's right for them is they've reached a milestone. And coaching isn't actually the thing for them anymore. It's I can break that off cleanly. And so I think that's really important to distinguish. It's, I still feel very much all in on coaching. I mean. Practically, I do have limits on time. But it's, a really good forcing function. I think what I'm experiencing right now is probably what parents of young kids go through. I, I hear all, I sort of see these tweets from time to time. People are, "Becoming a parent, I thought I was gonna lose my productivity." And instead, and they became more productive because I just cut out all the bullshit. And I think that's, I'm probably going through that just in a probably less intense way, because I think I don't think I'm not trying to say my life right now is as intense as being a parent of a one-year-old. The other big thing, not just in terms of, would it actually work, is sort of this, the theme of integrity. Do I want to be putting myself in a position where I have to go out and get all these, more clients, right? Am I trying to coach people that I'm not the best fit for, or people that? Am I kind of coercing them into coaching? Maybe there's, not in this season of life, where coaching is the thing for them. Maybe they're good for, they're better suited for therapy, or instead of conversations, right? Which is what coaching and therapy is. Maybe what they need is, to go spend a ton of time out in nature and move their body, right? Different people are, have different, different things going on. So, I think. There was a time, maybe a month ago, where I was going super hard on the job search. And I stopped writing, and I was also traveling and moving. So it's a lot of things in life. And what I took away from that was, I'm gonna do this search and explore things. And it's gonna just take its own time. I've got plenty of time. I'm not gonna run out of money anytime soon, and I'm also still gonna do all the things that I would have done if I went all in on coaching. And also, if, assuming I already had this job, I would still be writing my blog. I would still be coaching. That's how I'm invited.

Bryan Wagman: Yeah, I really like what, what you said about the interview and, and how, you realize where your priorities were and are, and are committed to maintaining the coaching thing. And if, if a certain, role doesn't, doesn't allow for that, or doesn't fit with that, then it, then it's not a fit for you. I think that's, pretty cool, and, and I've struggled with that a little bit, too, just in some of the conversations I've been having. Especially with how tough it is in, in the financial industry, because, there's all sorts of rules around compliance and marketing and things like that. But I've been, so far, I think at least pretty good about trying to be, straightforward about, "I really want to write this Substack. This is really what I want to do over time. I want to be able to continue to grow that while I do whatever else I do." And so, it's, it's tough, though, because, there's definitely been a tension for me in those conversations. There's, there's part of me that's, thinking to myself, "What are you talking about? You're at 450 free subscribers right now. And this opportunity you're looking at could actually, potentially pay the bills." But, but that's not what it's about. And I'm sure you understand that.

Matt Yao: Yeah. And there are also cases where you can. You don't have to choose between either one.

Bryan Wagman: Yeah, I'm, I'm looking for more of those. Some people have, have been, more open to it than others. But I guess it's just. It's part of that whole broader thing. I'm kind of grappling with the, with the uncertainty of, having left the job and kind of pursuing the pathless path, if you will. It just contributes to it, passing up certain job opportunities that I'd take otherwise, because it still kind of requires that same trust in taking the next step forward, regardless and trusting that it'll, it'll still work out. And it'll still, be fine, basically. But...

Matt Yao: Yeah, and also trusting that there might be a time in the future where you change your mind.

Bryan Wagman: Yeah.

Matt Yao: It doesn't have to be kind of what I said at the blind hope thing, right? You could be not ready for a full-time job, or whatever it is, right now.

Bryan Wagman: Hmm.

Matt Yao: And, if you maintain a level of self-awareness, fast forward a few months, or a year, or whatever it might be, a very different situation. I think I sort of in the beginning had to grapple with, "Oh, am I being a hypocrite by writing about quitting my job? Now, I'm trying to potentially. Go back." And I think, I asked my close friend. I was, "Dude. Do you feel I'm being a hypocrite?" He was, "Yeah, kind of." And then when I heard him say that, I was, "Oh, actually, I'm not a hypocrite." It's funny. It was he was telling me, "Oh, I think you're kind of a hypocrite." And then I was certainly asking him to sort of see what other people think. But when I heard him actually confirm, I guess what my fear would be, I actually was, "I don't feel I'm a hypocrite," because all I did was change my mind. If you, if you ask some 16-year-old dude, he's gonna be, "Oh, what do you want?" He's gonna be, "Oh, I want to have ten girlfriends," or whatever. And then you ask, a 30-year-old dude. He's gonna be, "Oh, I want a wife and kids, and I don't want to party," right? So people change their minds. It's just kind of, people don't change their minds that often, I think. And they don't. They also don't do it very publicly. So, it's a bit of a tangent.

Bryan Wagman: I've, no, I've, I've dealt with that same exact thing because I've been kind of documenting this journey on Twitter and Substack. And back in, March or April, I was, "I really want to be an entrepreneur. I just want to start my own business, whatever." And that's still the case. But, I just, first of all, just for financial reasons. I don't know if I'll be able to make that happen in the near term. And so, I've been kind of having to, I guess, come to grips with the fact and, and accept the fact that it's okay, to go do something else for a couple of years if I have to, and, or if I want to, even though, that may have not been what I was expressing publicly a couple of months ago. But I view it similarly to, I think great investors, Stan Druckenmiller or something, is famous for, he'll go on CNBC and talk up, whatever company XYZ that he's buying, and then, turn around and sell it a few days later, because, it's a strong opinions, weekly held, and when, when how I'm thinking about something changes. My actions should change accordingly. So I've been, I've been kinda, kind of wrestling with that, and just the, the public perception of it can be tough, I guess.

Matt Yao: Yeah, yeah, I'm just thinking if there's anything else I have to add. It's not just about changing your mind. It's also it's, it's not just about changing your mind. It's also just, there are certain things that I think we're living in a world that's gonna become increasingly more complex and chaotic. And there's gonna be more change across all levels. Economy, culturally, at a level of work, geopolitically, everything. And so we're gonna start seeing more examples that break the mental mold of, "Oh, it has to be black or white." And now we're just gonna be seeing a shit ton of gray things that sort of just don't fit what we expect to see out there. Whether it's doing a job just because you love it, even though it doesn't pay well. And then, trying to figure out a way to scrap together the rest of the money you need, or if it's quitting your job. Or there's all these examples, even just the fact that, people make millions of dollars creating content. That's already an example that I think has become more accepted by society is, "Oh, this is just the way it works." But five years ago or yeah, five years ago, that wasn't, that was kind of mind-boggling.

Bryan Wagman: Yeah, yeah, for sure. One of the things. So there was an interview I read that you did, I think you were six months into your sabbatical, and you talked about the process of decoupling uncertainty from negativity, and just getting more, more comfortable with, dealing with, I guess, those feelings that come up when you're going on kind of that pathless path type, type life. Where, where do you feel you've? How do you feel you've progressed over the course of the past couple of years with that decoupling? Where do you feel you stand today?

Matt Yao: Certainly it's not a straight line.

Bryan Wagman: True.

Matt Yao: It's ups and downs, constantly have to remind myself. It's a lot of reminders. And remembering that, that it's yeah, what, what you said, uncertainty and negative things are not the same thing. A lot of times we think they are the same thing. I had. I was just talking about this recently with someone of, "Oh, I should keep a list of every time something happens that I didn't expect." And it could be, maybe one of two ways. First being, I did something that was different than how I thought future would go. And then, here's an example. I just moved to Palo Alto three weeks ago. I spent six years living nomadically, not in Palo Alto. I never lived here. Asking myself, "Where do I want to live someday?" I lived in Hawaii. I lived out in Tahoe. I lived in Salt Lake City. I lived in New York City. All these great places. Some of them are great for, surfing, some are great for skiing. Some of them are just great cities. Full-time, I'm trying to figure out where to live. And then in the end, my girlfriend is in the medical field. And so where we ended up living is not even in our. It's not my control. It's not even in her control. And that's an example of, I would probably add that to the list. But there's also situations that happen where something else happens in your, somewhat, some other people or your environment. There's some event that triggers something in your life changes. And obviously, it's, it's unexpected. And, and so it's in this realm of uncertainty. And if you make a list of all these things that happen that are surprises to you, and you could roughly market as positive or negative. You might find that there's plenty of things you couldn't have anticipated that are actually not that shitty. And the other thing is, the whole point is that this is what makes life, meaningful, enjoyable, right? The reason why we watch movies or we play video games is because we don't know what's gonna happen. Video games are fun because you press some buttons. The thing on, the, the person on the screen changes, there's other people, other characters in the game. And then you have to respond. If it was not that, and you knew what was gonna happen, then you'd just be watching something happen. It wouldn't be entertaining. So, the element of uncertainty is not something that should be trying, you should not try to force that into zero. It's more about finding the level of uncertainty that you can tolerate, and then working with yourself to be able to tolerate it more and more until you find sort of an equilibrium. And that level can change over time. I used to be really comfortable with moving every month. And then now, in, at least in this theme of where I live, I want basically no uncertainty. When it comes to food, I want no uncertainty, meaning, my fridge is full. And I eat the same thing every day. I eat the same oatmeal for lunch every day. But when it comes to, the people I'm spending time with, or what I'm doing for work, what I'm learning about, it's, I'm totally okay with that being very open-ended.

Bryan Wagman: Yeah. I forget where I heard this phrase, there's, there's someone it could probably be attributed to. But I, I what comes to mind is the phrase increasing the surface area of serendipity. And that's, that's, that's one of the things that kind of fuels my interest in writing both the Substack, but also just, I've been trying to be more active on LinkedIn and more active on Twitter as well. And so because I think just I don't know what's gonna come out of those things. Ultimately, every job that I've had so far, and internship, has come either directly or indirectly out of writing online. Because I wrote for, Seeking Alpha back when I was in high school and college. And so I just think it opens up opportunities for things that I couldn't even predict. And so, yeah, the main thing that I think about when I think about writing the Substack is, hopefully, I can make a living off of this someday, but I think there's also a lot of room for positive surprise in terms of what else could come out of that between now and then? What could I learn? Who could I meet? What relationships could come out of that? Could other work opportunities come out of it? So in, in having to, trade that the way I have in, in the past, jobs that I've had is just something that I've decided is, is not worth the tradeoff anymore.

Matt Yao: Yeah. Have you talked to any of your subscribers? Have any of them reached out?

Bryan Wagman: I've, I've had some conversations, because a lot of the subscribers are just, people I know. And so obviously, I've, I've talked to them varying degrees. Maybe we already had kinda, a relationship of talking stocks now and then, and then they sign up for the, for the newsletter. And so there's been stuff, some stuff that. And I would say, not, not that much, though, and I haven't reached out to that, many of them either. It was interesting. A couple of weeks ago I published a write-up on just some small, smaller micro-cap software company. And someone who runs a fund that owns, is a large shareholder of, of one of the companies that I, follow closely, and have been invested in the past, signed up for the newsletter, and so, I don't know. I haven't reached out to him yet, but I might end up doing that at some point. So it's just that. That's the other thing, too, that kinda even though the progress on the actual subscriber count and, how am I gonna make this paid has been, has been slow. When I see someone that sign up, it's, it's fuel and motivation. It's, "All right, I'm, I'm on the right track here." If I just...

Matt Yao: Yeah.

Bryan Wagman: Be consistent and keep putting content out over time. I think something good is gonna happen.

Matt Yao: Yeah. The reason why I asked is, it sounds you're writing mostly about stocks. Even just one example of, you could spread your, you could increase your surface area by publishing more often, writing better, right? So it's spread more. You could also increase your surface area by writing about other topics, not, not in a forced way. Things that you're interested in, or, and or, incorporating more of yourself into it. I think that's, I've done. I've, I'm really bad at a lot of things when it comes to the Substack and growing it. I have less than a thousand subscribers writing for a few years. There's people that grow much faster, but I think what I have done well is, I'm very real. I'm very, it's very much me.

Bryan Wagman: Hmm.

Matt Yao: And sometimes it's my judgment, right? But when someone reaches out, they just, they, they're sort of self-selecting. They are just, the fact that they reach out to me, I already am, "Okay, we're probably gonna have a good conversation," because if this person has read enough about me, and they don't resonate with it. They're just not gonna reach out. And yeah, I, I do think there's something about putting out feelers for other people. Paul Miller, right? He, you mentioned. He also has this phrase, "find the others," and I think it's finding the others. But it's also allowing the others to find you. And I think, it's, it's, it's both. It's not what it's not just about it being this, relentless search, looking for random people on the internet that you look up to, because that can feel a little bit one-sided, and it can feel a little bit you're being desperate at times, or I'm just talking about the, the fears that people have or, "Oh, it's, it's pointless." Or, "When is this gonna lead to something?" But if you just, put yourself in a position where you can be discovered, then it feels a little bit more symbiotic, or it feels a little bit less of a power dynamic and more, "We're all just peers. We'll just, peers floating in this space called the internet."

Bryan Wagman: Yeah. Yeah. And, and I've experienced some, some fear about sort of that idea of, posting more, posting about different stuff, because when you talk to, I talked to several people who have started investment newsletters over the course of the past couple of months, and a lot of them will say, "Oh, you gotta be consistent with when you publish, and if you publish stuff that people aren't interested in. They might unsubscribe." And it's, it's definitely been a consideration that's kind of in the back of my head even when I think about, is, I mentioned earlier, I, I don't know if this is gonna be a podcast or, or a video, or written form, or, or whatever. But if I do, do a text form, I'm trying to think, "Okay, well, I'm doing an idea write-up, about stocks every two weeks, and maybe someone signed up for the newsletter because of that. But what are they gonna think if I, release an interview that has nothing to do with stocks on a Wednesday," or something that. And it's just I feel my intuition is that it's not something I should be worrying about. But it's, it's been. It's been slow to put that into practice. Kind of similar experience for me with posting more on LinkedIn. I posted something today about a conversation between Steve Nash and LeBron James. And I was, this feels...

Matt Yao: One of the game.

Bryan Wagman: Yeah, yeah, exactly.

Matt Yao: Yeah, so if you didn't bring that up just now. But maybe something in your head was, "Oh, should I bring this up? Oh, I don't know if Matt likes basketball."

Bryan Wagman: Yeah, yeah, and you...

Matt Yao: We wouldn't. We wouldn't know that. I sometimes watch that podcast, too. And, and so that's just an example. So there is that, yeah, this is again, theme of uncertainty. And there's also tactical ways. So, I've seen podcasts where they have the video, or they have the audio and the text. People have different preferences. Even for me, sometimes I read these text-based interviews. If I just happen to be at my desk in the morning, and it's something. It's a different type of content. There's different types of knowledge that I want to read. And then there's things that it's I want to listen to, because I can go for a walk, and it's more enjoyable, or I'm driving. But I also think, the other thing that's important to mention is, we live in this, you know this phrase, the attention economy, right? Attention is the, it used to be data is the new oil. Now people are, "Oh, it's attention is the most scarce thing." And so I think it's really important to honor the reader's attention, but also not forget, they are subscribed for a reason. They want to hear from you. And so the way I think about this for me is, well, also, you have to consider, it's only gonna be good if you care about it. So, if you're writing about a stock that you don't give a shit about. It's not going to be good. But if you're writing about something that you're obsessed with, and you really enjoy learning about, it's gonna, it's gonna be apparent. So the way I think about it for me is I try to select a topic to write about that I'm interested in. Usually it's about my life. So it's not as hard. And then I try to get to a point where, before I start editing, I feel complete. I feel I've discovered new things. I've learned more about myself. I feel I've covered, most of the territory of the train. And then when I edit, I try to be really aggressive in trimming out the fat. Just the way I write is, I just ramble. There's lots of filler words. And so I use Chat GPT to help me edit and just point out all the areas that I can make more concise. Then that way. I'm honoring the reader's attention by, not subjecting them to read all this extra fluff, but I'm still being very, I'm taking it very seriously on what I choose to write about, and making sure it comes from an authentic place that I'm curious about.

Bryan Wagman: Yeah, no, totally. Yeah. I, I agree with that. That's something I, I try to be 'cause there, there are some times where again. It's that the tradeoff can sometimes be right about something that's popular, right about something that I'm interested in. And that was I, I definitely thought about that over, over the course of figuring out what I want my newsletter to be, and I'm still not sure what, what direction I'm gonna go with that. But another piece of advice I received from some people is to, find a niche and write about that. And so, but at the same time I'm, I don't know. I, I really, respect the work that the guys at Semi Analysis do about semiconductors. But I don't know if I'd want to be looking at only semiconductor companies and never anything else.

Matt Yao: I think, having, having a, having a niche is really good for, it makes a lot of sense for business, and actually something that I'm sitting with right now is I, I'm pretty sure I have my niche identified in coaching, but I haven't taken the action yet. But I think having a niche is actually really bad for finding other people, and being in sort of the, in this, in this, in the flow of the internet, and connecting with ideas. I think this podcaster Dwarkesh called it, the marketplace of ideas. So you could think of it, you're putting something out, and it's getting matched to other people that are interested in it. And if you, if you sort of prematurely restrict yourself, then you are prematurely shutting yourself off to serendipity.

Bryan Wagman: Yeah, what's the niche that you're thinking about for coaching?

Matt Yao: I think it's gonna be something around people who are considering quitting their jobs.

Bryan Wagman: Interesting. Which is.

Matt Yao: It's, it's, it's, I spent a year kind of running around purposely, not having niche, but, at, it was a point where I was, "Oh, what's my niche?" "Let me go look super far out there to find it. Let me go research other coaches. Let me go think about whether it makes sense on paper. Let me do some analysis." And then, it just came to me when I was talking to someone else who's about to start coaching. Yeah, I'm happy to get into it, but it just makes a lot of sense.

Bryan Wagman: Yeah, no, I, I think that's a really good and interesting idea, because, one of, one of the things that, one of the ideas. I had kind of bounced around in terms of trying a podcast was for people who had, quit their jobs with nothing lined up, or were going through some other kind of transition period. Because I think, I really think, and you put it so well that, decoupling of the negativity and the uncertainty. That is something that I think probably, in, in different words. Paul writes about it, too, in The Pathless Path, but I think anyone who's, quit their job, and, and not been sure of what's next, has experienced that, and I feel I had. I did not, I would not have been able to articulate or quite understand it as well when I was still at my job. But talking to other people about that is super interesting to me, or hearing what other people have to say who have actually experienced that feeling, too, would, would be super interesting to me. So I think that's, that's a cool area. Yeah.

Matt Yao: Yeah.

Bryan Wagman: I wanted to ask about the subletting stuff, actually, because there's a part of me that just wants to. I feel the first step might be. Getting getting rid of all my stuff, so that I have less reason to stay put, because I've, I've never, moved around. I mean, I guess I've, I've moved some since I graduate, since I graduated in 2018. I've lived in a few different places, but I've never done an extended period of a month-to-month. Type thing. Which I feel could be really interesting. So I guess if, if you could start just tactically. I'm very curious to hear how you go about finding these awesome, whether it's sublet opportunities or Airbnbs, or whatever it may be.

Matt Yao: Yeah, let's start with this. Where are you now? And where? Where? Where are the places that you, you would consider trying out?

Bryan Wagman: Yeah. So I'm in Chandler, Arizona right now. Right outside Phoenix, and the main two places that I'm thinking of. Well, I guess kind of depending on how you break it down. There might be a couple. One is just somewhere else in Phoenix, so staying in the same metro area, but just trying different neighborhoods and things that. And then the other two, kind of one is basically Austin. But there's also I got a friend who I grew up with that lives in Point Venture, which is a small town about an hour outside Austin, right on Lake Travis. So those are kind of the different areas of interest to me right now.

Matt Yao: Yeah, the first one's interesting. It reminds me of this. I think it was a Substack that this, this girl Ava wrote about. It's this idea that the neighborhood that you live in plays a bigger role in your experience in the city that you live in.

Bryan Wagman: Hmm.

Matt Yao: And I think that's very spot on. You just end up settling into a routine. You're more likely to walk than you are to drive, or you're more. You're more excited to do that, I should say. And so... Even if you just move 45 minutes diagonally to the other side of the city, it could actually change things up a lot. I coach. I coach a client right now who recently moved to a different part of his city. And it's slightly more expensive, nicer place. It led him to changing gyms. He's at a, he's at a gym that he's much happier at. He's met more people, more like-minded people, and then also signed up for a coworking space. And then that, that went, or you, he's a solopreneur. So, sort of before. That was more isolating, you know. Default work from home. Try to co-work with people, but it's sort of ad hoc, sort of stitch together. And then now he goes to his new coworking space, and then he's even trying to form his own office with other solopreneurs, sort of find, outside of WeWork or whatever it is. And then this idea of you just working with your friends. And that was all. Just because he moved neighborhoods in the same city. But yeah, in terms of subletting, I think it's this super interesting thing, 'cause it's, it's just so, it's so not deep on the surface. It's just, "Oh, you don't have a lease, and you just move around all the time." And there's a lot of, I feel there's a lot of depth and, and philosophy in this, in this sort of even just in, in thinking about wanting to do it. And then, obviously, there's the once you're actually doing it. But in terms of tactically, the first step is yeah, your stuff. And I think, even as you get rid of stuff that will probably be a fun, a fun learning experience, of learning how little you need, and you might...

Bryan Wagman: Was there a point where you got rid of a bunch of stuff?

Matt Yao: Yeah. So I was living in SF for a year after college. And I guess it was a good thing that all of, a lot of my stuff was just from college. I went to Berkeley, moved to SF, so just rented a U-Haul. And a lot. Even the furniture I had in college was used IKEA furniture. So it's the cheapest brand, and it was used. And then I'm bringing it as, as a person that makes good money now, as a new grad. And so when I moved out, I just, one of my roommates was staying in the city, and, and actually just moving up one floor in the building. So certain things I just let him have. Wasn't worth trying to sell my roommate stuff. And then for the bigger pieces I, I remember I think I listed my bed for 150 bucks. No one was buying. I just made it free in the last week, and then some Berkeley student came and picked it up, and I felt good about, "Oh, I helped, someone from my Alma mater." So I got rid of all this stuff. And then, fortunately, my mom lives in this area, and I can just basically store all my stuff. So I have. All my camping, backpacking gear, I've got all my ski gear, and then, obviously, different clothes for different seasons. And then, yeah, then you just, you just go off and, and do it. And then, in terms of finding the sublets. It is a skill. And in the beginning you just, you just sort of, learning, right? You just don't really know where to look. So when I found the first sublet in Hawaii. I just went on these Hawaii, Sublet, Facebook groups. There was some real estate agent. He had a basically a, a hotel room that was not serviced by the hotel. So it was privately owned. And so it's, worst of all those situations, right? No kitchen, maids don't come and clean up after it, after me. And so I just eating weird food. I was eating oatmeal every day, and then I was making chicken salad, Costco chicken, shredding it up, and then eating with spring mix. Very simple stuff.

Bryan Wagman: Yeah.

Matt Yao: But then I was in Hawaii, for the first time, and I was doing all these things didn't even matter that I didn't have this stuff, and I paid this real estate agent, probably 500 dollars extra as a premium, just because you know that they have to make money, and then over time I got better at it, and then I was able to make friends, and then I could just ask them instead, and then pay their friends' rent, which is much cheaper.

Bryan Wagman: And yeah, I've been thinking about it a lot lately, and one thing that I kinda recall is, when I moved here to Phoenix. I moved here from Reno, and I drove down here and beat the moving truck here. So for the first week or so, basically, all I had was, I mean, I was sleeping on an air mattress on the floor, and I had, a couple of suitcases of clothes. And I really like the simplicity of that. And basically it was, I needed stuff to cook with, which I could have just gone out and bought, but, honestly, it's, it's, it's crazy to think about it. But I could have just been, "I don't even want the rest of the stuff in the truck." Just leave it. I could have definitely, lived with what I had if I just went out and bought some, pots and pans and stuff.

Matt Yao: Yeah, have you watched the movie Fight Club?

Bryan Wagman: Not in a very long time.

Matt Yao: Okay, but you've seen it.

Bryan Wagman: Yeah, but I don't. I don't hardly remember it.

Matt Yao: Okay. I watched it for the first time, a week ago. And it's, there's a lot of themes in the movie, multiple themes. But there's this theme around anti-consumerism, anti-materialism. And it sort of portrays this in a very violent and intense way. But I think there's a lot of truth to it. It's, think about how much time we think, spend thinking about, "Oh, my life would be marginally better if I updated my desk." Right now, I'm using a white foldable table that I've had in my family. It's, I don't know, ten years or something. I, I mean, I'm, I'm probably gonna get a standing desk, to be honest, eventually. But there's nothing, there's, there's not actually, it's not that bad. And think about how much time we think about, think about how many people get money for working their jobs and then go and spend on something that's not that important. And what I've been doing here. We've moved three weeks ago. It's, there's something actually, really interesting about, I get a new piece of furniture or something, and then I, and then there's a few days where it's a new apartment. There's something that was added. And then, maybe a few days later I, I changed the orientation. We moved where our couch was to the opposite wall. And then I sort of let it linger, and I really sit around. And then I'm, "Okay, actually, I do think this would be worth it." "I have 50 books on the floor. I should get a bookshelf." Or, "Oh, we should get a rug." And it's actually letting myself linger in this mild, very, very mild discomfort, and then choosing to buy the thing that makes me feel good about the purchase that I'm making, and it still feels a pretty simple place.

Bryan Wagman: Yeah, yeah, I like that. I think that's the way to do it. I, I'll probably start by. I don't know. I don't even watch TV anymore. I might try to get or not try, get rid of my TV, my TV stand. The bed is...

Matt Yao: We just picked up a TV. It's so funny. We park our car two car spots away from the, the trash for this apartment complex. And someone just left the TV. And I kind of came home at night. And I, put my phone flashlight all around this TV. I was, "Where's the crack?" There's gotta be something busted, really, nothing wrong with it. And it's also, not in the trash. It's on the floor. It's on the, the asphalt. And we just, have a TV. There's no cord. So we have to buy the power cord. And then, probably HDMI cord. I'm, "Yeah, I guess we just have a free TV now."

Bryan Wagman: Yeah, I'm thinking about doing the same thing, just dropping it out there.

Matt Yao: Yeah, I mean, there, the, it's not even another man's trash. It's not really trash to you. And it's just, but someone else will get a value from it.

Bryan Wagman: Yeah, yeah, you, you write and talk a lot about tech addiction. Is that something that you've worked on a lot in your coaching?

Matt Yao: Yes, it comes up often, but it's not a focus, and I think it makes sense given. If you just think about, let me try and break down what coaching actually entails. Maybe that will help. I think most of it is the central pillar is one's relationship with themselves. This is things around self-confidence, self-awareness. Feeling stuck, feeling confused, feeling frustrated, right? A lot of stuff around, yeah. Just, what do you want in life? Who are you becoming? These sorts of big questions. Another huge part of it is relationships. And it's sort of complementary, right? You can't just be in an echo chamber with yourself. Life is. We're meant to live with other people. And so so much of the work that I do with people is how to have healthy relationships and moving towards healthy relationships actually often involves conflict and not let anything stifle and have it breed resentment. So there's a lot of, "Oh, how can you give feedback to this person? Or how can you, express what you want to this person, or create a boundary," or stuff that. So that's why I think, the topic of relationship with technology is a smaller segment, but it actually, surprisingly comes up with pretty much every client at some point. And the way I structure the sessions is, I'm not saying to this week, "We're gonna do this," or there's no syllabus, right? So it's all about this set today, the client reflected. Sent me notes that say later today, when we meet, they want to talk about this, because for the past two weeks this has been the most important thing in their life.

Bryan Wagman: Hmm.

Matt Yao: And but then sometimes we just end up in a session. And then the common, entry point into this theme of technology is overwhelm, overworking, lack of feeling energized when they wake up in the morning, feeling overstimulated, feeling anxious about things outside of their control. Israel and Palestine, right? The, from watching the news, stuff that. And it makes sense, right? Because we all use smartphones. We all pretty much are knowledge workers for the most part with who I work with. And all of these devices have been designed to maximize engagement. So all these, a lot of these companies, if you think about news, social media, the more time we spend on them, the more money they make from us. And they spend billions of dollars on talent to design these devices to be as addictive as possible, so to counter, to move in a counterbalancing motion. It's gonna require some intentionality. It's not just, if you just let it drift without intention. You're gonna end up doomscrolling, which is what a lot of people are doing.

Bryan Wagman: Yeah. Yeah.

Bryan Wagman: I guess we'll probably start wrapping things up. I wanted to give you an opportunity to just kind of talk, about, where can people find you? And if you want to talk about, your coaching at all, or what sorts of opportunities you're looking for in terms of work.

Matt Yao: Hmm, yeah, I appreciate it. For coaching, my website is mattyao.co, so MATT YAO dot CO. My blog is morehumanpossible.com. And in terms of what I'm looking for, I've been spending most of my time looking for product roles. Product management was my past life. But now I'm actually giving a pretty open, pretty open-ended. I would like to work with either a team or actually an individual who we just have the same values. So I don't know if someone's listening to this, they probably have a decent sense of who I am by the end. I've just been talking about myself, and we didn't have a fixed topic. So I'm just talking about what my beliefs are. So, they could reach out, my website has, a way to get hold of me. Blog can also definitely find a way to get a hold of me. And also, who knows who's gonna listen to this. But if you're, if you're listening to this and you want to chat, just reach out to me.

Bryan Wagman: Awesome. Well, thanks, Matt. I appreciate it. Thanks for your time, man.

Matt Yao: Yeah. Thanks.