Episode 1: Permission to Build Your Way

I mean, I think if we're being honest, that's when things aren't working well, we almost never really know why. When things aren't working well or working well, we don't really know why. So when it's fine and then it's not fine, we're stuck. And surely we all feel that way. You just worry. You don't know whether you know what to do next. You have a to-do list of things you could try. You have no idea if any of those are right. You don't know if the best thing to do isn't even on the list. No one can tell you the answer, including my book, right? Like I got a whole bunch of things that tend to work or whatever, but like nobody knows. Maybe nothing could work. Even in retrospect, you're not going to know. Like even if it turned out to work or even if it turned out not to work, can you know even in retrospect that there was something you could do or you should have done something else? No, you'll never know, especially not ahead of time. That's a pretty helpless feeling. And yet I think, you know, when you start a company, the idea is I'm going to do this. I'm going to make the product. People are going to love me. They're going to give me money. That's how much they like it. And yet almost nothing's in your control and you know almost nothing and you know that. So sometimes you feel it too.

Just identification. I didn't want to make the reader feel differently than they feel. If the reader feels that way, I want the reader to realize I understand. Like I can't write this way unless I get it.

So that means I understand. But that may give me some credibility in saying, 'Hey, but sometimes these various things work. I've obviously felt the way you felt.' I mean, I say that too, but hopefully it's obvious just by the way it's written. And so if some of these things sometimes work in things that you and I have experienced, then that could work. That could be helpful. Let's do that.

Yeah. I mean, you could take a negative view of that and say I'm just hedging constantly. Like if I say, but it might be wrong, then that way if it is wrong, you don't lose any, I don't have to feel bad about that, you know. So you could say that it's bad hedging, but again I think it's true that nobody knows. Even if I were closer to the business, I also still wouldn't know. So what we can do is I think as outsiders, we can hold up a mirror so that people can see themselves and their own actions and choices and what consequences those are having for themselves or for other people. But to hold up a mirror, they have to believe that you have the credibility to understand generally what they're going through and that you're telling the truth. So I mean, to me it's like there's no great tennis player that doesn't have a coach.

Why the coach isn't better at tennis than that person and the coach isn't having to play that game right then. So what's the point of this coach? And you know the point isn't that the coach is better at tennis. So the point is that the coach can see things and the coach knows enough about tennis. They're an expert in tennis, right? They're just not a top 10 player in the world, but they're an expert in tennis and they can observe things and they can see things and they hopefully understand that other person better. And they can reflect back to them things. I've seen this, that you might try this. I've read this other thing. I've seen this other thing work. I know you and blah blah blah. And so everyone needs that. An author needs an editor because you can't see your own problems. If you wait a year and look at your own writing, then you can see a bunch of problems. So if you want to wait a year, go ahead. But you don't have that kind of time. So you need an editor. Not because you're dumb and you don't know how to do it. Not because the editor is better at writing than you, but because you're too close to it to see. So whether it's like that and you're just too close to it temporally or whether it's like a tennis player and their coach, that's what a coach can do. And of course, there's many other things. Do they have empathy? Can they communicate? Can they teach? Can they do it in the right way? There's many, many things, right? But just why can't you do that for yourself? That's why whether it's the author thing with writing or whether it's the other thing, you need someone else to be an intelligent, credible, honest mirror because you can't see it when you're inside of it. And so if I were in the company with them, I probably also still couldn't see it. I have to not be in the company in order to have that outside view. On the other hand, of course, the coach isn't in the arena. So ultimately, that is also true. So while you could say it's a hedge, okay, it's also true that you're not in the arena. It's good to acknowledge that.

Well, I don't need to make any money on my advice in any way, courses or talks or I guess now I have a book, but like it's priced to not make a lot of money. It's a book. You don't make money off of books anyways. What you're supposed to do is make money off of what comes after the book, like consulting and stuff, but I don't do that. I don't do any of those things. So I don't care. I just want to put these ideas out there and hopefully they help some people. And of course, there's the ego of people saying, 'Oh, I love that.' Or whatever. I like that. That's something I get. That's better than money. So I have the advantage that having, like you say, being successful on the business side, I don't ever have to make money on quote-unquote content. So I don't write content. I write things that I think are good. I write long-form articles. I write books. I don't write content. To me, that's the throwaway stuff you do to fill an algorithm. I just won't do it because I don't have to. It's a gift to not have to. So I'm not going to play into a game that you have to play to get attention since I don't need that. I don't have to. I can just do whatever is my best work, whatever that is. And some people like that.

And it's nice. It's nice when it is. The internet on its best day is when people are actually being people and authentic and interacting. That's the good part. So I try to do a little bit of that.

Yeah.

Yeah. Yeah, but I'll give you an example because when you have a so-called weakness that is enabling something else that is unusual. For example, if I say, so like Etsy, you could say that they're handmade products and they're expensive quote-unquote versus what you can buy mass-produced from China. So you could say a weakness is they're expensive for what it is. Well, if you define what it is as just the function of the thing, right? And sometimes they're not made perfectly. They have little threads coming out or weird little seams and stuff. You could say that's a weakness. That quality is low and price is high. What a bad combo. That's clearly a weakness. Now, we all know, yes, there are times where that is a weakness. If I need high quality at a low price, then indeed that is a weakness and I shouldn't buy things that are handmade off of Etsy for that. If that's what I need, then it's a weakness. But suppose I just like it. Like I like little pouches and bags and things. So I buy stuff off of Etsy that people made. And then when I see an errant thread, I just clip it off. And that reminds me that a human being made this and I paid too much. What do you mean? I'm helping somebody with their craft or artistry. I think that's awesome. I would pay more, you know, like I think it's a good thing. So for me and many people who buy, millions of people who buy things off of Etsy, when you're supporting a person and getting a handmade thing, those quote-unquote weaknesses of the errant thread or the weird seam or the high price is not only not a weakness, it's evidence of the thing that I actually love about it, which is that it's handmade and craft. It's good that it has those because it's almost proof of the thing I actually wanted, which was to support a person in a craft and have a unique or at least handmade thing. So that's a specific example of what I mean by the people that really love you for you either don't care about your weaknesses, right? Either they just don't care that that's common, that's more common, or it's evidence of the thing that they are here for that they love. And so in that sense, I don't know if it's a strength, but it's actually a good thing.

It's not a platitude. That's how it works when you found your people.

Oh, I still try. I just know it's a stupid idea and I try to put all my energy into the group that does and I try not to listen to the other stuff. I just try. I mean, none of us are perfect here. In fact, it's funny. I often say the reason I'm writing it on Twitter, on a poster, in a book is to remind me. I need to remember this too. You know, it's not like I have this nailed down. I know this is the right way to think and act. I know that. So the more I can say it, the more I can remember.

I mean, it still feels bad, but it's a little more easy to ignore when someone's a real hater, obviously.

Yeah. What's actually hard I find is when the person is not a hater. They just have a different point of view and they wish you would do something else. And so the number of times I've been told like, 'Oh, you should hire so-and-so and they could make these kinds of Twitter posts for you. You should have 10 times the audience. Like here's these other people who have 10 times the audience and they don't have better ideas. They have good ideas but not better than you, but they have 10 times the audience because they do this and they do that and you should.' So that's not a hater. That's a very well-intentioned person, but they want me to do something that's not like me and that whoever likes me doesn't want me to do those things either, right? So that's hard to remember because you're like, 'Ooh, 10 times the followers. Who doesn't want that?' Right? So it's hard to remember.

No, no, no, no, no. I'd rather have fewer followers that actually love it. That's better.

And I know it is better. And it does feel better, but even I have to remind myself of that. You know, of course, my ego wants to see the number with another zero. Why not? So I have to remember.

That's a toughy because each time you say I should work on it, you can't work on that many things, at least not at once. So that can't be the answer. And yet you also have this feeling of if I just say all these weaknesses or all these failings or all these things I don't like about myself, let's just say they're all fine. That just doesn't sound right. You know, like that can't be right. Surely the right attitude somehow is to accept what I am now and also strive. Both. This is good enough and also I want to be better. That has to be the mindset always.

Right. So your question was, okay, so within that though, how do you pick of your many things you could work on? What do you do? So I have a few ideas there. One is when you know what your goals are, like I'm trying to get this company to do this or I'm trying to build this out or I'm trying to make this product or trying to do this with my career. I want to have this kind of relationship with my spouse or kids. Then if you know here's the one, maybe two, but not like five goals that I have right now that I'm really trying to do. And if this weakness is actively harming and holding you back from what you said is your number one thing, that's something that you should fix. Not because I think so or society thinks so, but because you yourself said that you want to do this more, that this is the most important thing and it's stopping you from doing that. Okay. Well, then because of your own decisions, just to be self-consistent with your own decisions, you would say, 'Ah, but there's 10 other things I wish I could also have as goals.' And I would say, 'Oh, I know.' And you're not even wrong, but you've got to order them a bit because you can't work on them all. And so when you say here's the number one thing and this is holding me back from that, then that is one you should, again, because of your own, just being self-consistent with your own goals, strategy, etc. That's just what it means to be really working on that goal all the way. So that's one. Another one that's similar is values that you have. So this is separate from a goal because a goal is something more like I want to achieve this, have this come about in the future, something like this. Some future state that's different from here that I'm trying to achieve. That to me is a goal.

To me, values are more like, you know, integrity or I believe in treating other people this way. Even company values when they're not stupid trite things like, you know, like we love our customers, like okay, like as opposed to what? That's not a value. Like what are you going to do differently as a result of this? Right? When you have ones that are specific and legitimate, then one of the rules is you don't violate those no matter what. Even if it costs you money, costs you reputation, a talent leaves the company, customers leave the company. That's what it means is that you will adhere to it even when it's hard and there's consequences. Okay. So weaknesses is another one of those. If one of your weaknesses goes against one of these things you say is an inviolable value or philosophy or thing, then you're like, 'Ah, okay. Well, then you're saying that you're not living up to your own values, your own philosophy.' This is similar to a goal, but goals aren't the same kind of thing. And goals change and values change but often less quickly, right? Or maybe because you realized something as opposed to a goal where you're making decisions. And so it's similar, but it's another one of these like, well, if you put a stake in the ground and you yourself aren't living up to your own stake in the ground, there you go. So in that sense, it's a similar pattern. Another one like if we switch to way more tactical, it could be something like many, many founders are bad at working with the people in their company. Like one of the reasons they started a company is because they're bad at working with people. They're like, screw this, I'm doing it myself, right? Well, you didn't suddenly become good at working with people. Like if anything, probably worse because now you have some positive reinforcement that your ideas are the best, right? Because things are kind of working. So that's bad. So another piece of evidence that again maybe you need some outside-in view to see maybe is something like your team is having to work around you, tread lightly, pre-chew food for you in terms of information, how they approach you on things, they strategize about that and just imagine how much time and energy is being wasted managing you. And if that's the case, then this weakness of people management, hopefully we could be more specific for a specific person than that, right? But that would be some evidence that there's this weakness that's causing all this turmoil in your team or your family or okay, it could be something else, but you know, I'm just using company as an example. That's what I write about, right? I'm not an expert about families, but that would be evidence of like, oh, that's a weakness that's causing all these problems and so that needs to be addressed. Now when I say address, like I don't mean suddenly you're or maybe not even suddenly that you have to become the best people manager ever and you won't be probably because it's not in your bones, but you could shave off the really bad stuff and get to neutral and that's important because if it hits one of these things I'm saying it needs to get shaved down at least blunted.

Well, I'm probably not good enough at analyzing all that. What I found works pretty well for me is kind of like a daily note type of thing where I just say at the top of the day, and now I use Obsidian daily note literally for that. But before I just had another note that I would just go to every day and sometimes update and it would just have things like this is the number one thing at the top, just be there. And I would just look at it every day like, you know, and if there's a couple important things coming up that need to be done or something like that, they would just be literally bullets. And then often there were something I was working on, often related to people or organization management things like that because at WP Engine we grew to over 1,200 people and I'm one of those people who intellectually can tell you a whole lot about managing people and teams and also it's a weakness of mine. I'm not good at it and I don't like it. So I constantly was working on stuff and had things to work on. And so I would look at those early in the day, remind myself, you know, like, oh yeah, you know, so one example of that just to make that concrete, for a long time I had these bullets that said, 'Does this need to be said?' And then on the next line, 'By me?'

And then on the next line, 'Right now?'

Right. And it's like, and with the idea...

Yeah. Now, I did not invent that. I wish I did. And I unfortunately have forgotten right now where I heard that. So I'm sorry to whoever invented that, but anyway, I needed it, right? And maybe, like you say, maybe we all do. Maybe many of us do. But anyways, because what do I do? I jump out in the conversation and I have an opinion and I cut people off and I talk first. All these things that are a bad idea, you know? So this was my way because by the time you get to the end, the answer is almost always no, right? But also what I liked about it too is it suggests what you could do. It's not like I should never voice my opinion ever is not the answer. It's is now the time and the place and the this and the that. Right? So it could just be that the time is at the end of the meeting, not the beginning or the middle of the meeting perhaps. Or once everyone has had something to say and then me, even though it's 15 minutes in, or if that's not happening, I could facilitate that. I could say something like, hey, so I have some thoughts too, but we haven't heard from so-and-so yet. Like I'm just saying I have an opinion. I'm going to have an opinion. I can't not have an opinion. That's also just not doing my job. But I can do it in a certain way. And this is just the simple, simple, simple way to remember, you know. And then by me, it could be that, oh, I could pass this along to so-and-so's manager instead of telling directly is the really obvious one.

And then right now maybe, oh, that's a really good point, but I'll interrupt the flow and anyway I'll call someone out. I don't want to do that. So I'm just going to make a note in my next one-on-one with them. I'll talk about it or I'll send an email afterwards or whatever, right? Just such an easy reminder. Does it need to be said now? Like it's the simplest question. It's like, oh yeah, if no, there's like a million ways to do it. And then occasionally the answer is yes, but okay, I've thought it through and I'm going to have to shut up like 90% of the time. That's pretty good, you know? So that's an example of the kind of things I would have in this. Simple, simple, simple. If it's a bunch of stuff and lots of fields and you're clicking around and it doesn't work unless you're on the internet, then you're not going to do it. So I feel like simple matters. Having said all that, I think personal productivity and these kinds of things are so personal. I just, I really don't think, and here I am hedging. Okay, fine. I'm hedging. So you can call me out for this hedging. But it's so personal how this works. I mean, one person will swear by, I do OKRs and this other thing, and someone else will say, and in fact I do. You should write it down in the morning on a little pad with paper that you like and a pen that sparks so much joy because it's made out of titanium and it clicks and it has these little ridges so it feels good.

Exactly. Affiliate links in the wherever you put things. Yeah, exactly. And so that's what I do. And so I just feel like it's so personal. What do you do that makes it something that you enjoy and you do every day because you like it, because it's convenient and right there, or because in material things maybe it sparks some joy to do it and so you do it. Like it's just so personal what that's going to be. But I do think probably to not hedge, simplicity is important. If it's complicated, I sort of, I just doubt you're going to stick with it. But then you're going to show me someone who is like that and that's fine. Okay.

Yeah.