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Ep. 236: Hacking Remote Work


Chapters

0:0 Cal's intro
0:10 Opening chatter
11:8 Today's Deep Question
34:30 Cal talks about Better Help and ExpressVPN
39:33 How do I leverage a shift to remote work to gain a deeper life?
43:30 How can I work deeply in a remote job that requires me to be available?
53:57 How do I make time for my individual projects while working remotely?
55:45 How do I avoid being promoted out of a nice remote position into a miserable management role?
60:53 Case Study - Alternative Workflow Pitfalls
65:50 Cal talks about ZocDoc and Ladder Life
70:4 The five books Cal read in January, 2023

Transcript

That's today's deep question. The deep question we're gonna explore today, how can I significantly decrease the footprint of my remote job without anyone noticing? (upbeat music) I'm Cal Newport, and this is Deep Questions, the show about living and working deeply in an increasingly distracted world. I'm here at my Deep Work HQ, joined as always by my producer, Jesse.

Jesse, we're coming up to a milestone, a random milestone for the show, but one nonetheless. 10 million downloads. Really? Yeah. Wow. We'll be there in a month or so. That's a lot. Yeah, I mean, I don't know, these numbers are kind of arbitrary, but as someone who was on my publishing team, they needed updated numbers for internal whatever, 'cause my book, and I was sitting along the numbers, and they said, "That's a lot of zeros." So we're adding, we're about to add a new zero to our list of downloads.

Wow. Little known fact, podcasts monetize at about $10 per download, so we've made $100 million off of this show. That's how it works. Oh, well. Anyways, I saw something. I saw something in the newspaper recently that was doing what we could think of as a reality check on some predictions I've been making, and I think it's good for us to hold ourselves accountable, so I wanted to load this up real quick.

I saw this in my hometown paper, "The Washington Post," and this was, I don't know, a week or two ago that I saw this. I've loaded it on the screen, so if you're watching this at youtube.com/calnewportmedia, this is episode 236, you'll see this on the screen, but I'll narrate it for those who are listening.

It was a cover article, actually, in the paper version, the business section of the paper version of the paper, and the headline is, "America's offices are now half full. They may not get much fuller." It's based off new data about office occupancy, and then they talk to some experts about what they think this means and what's gonna come.

This is a good chance to hold myself accountable, so starting in May of 2020, I began making predictions about what I thought was gonna happen with remote work, and the trajectory of my predictions was twofold. Early in the pandemic, in May of 2020, I had one prediction that I then refined as time went on, and my refined prediction, which I talked about for about a year or a year and a half, was that as the acute phase of the pandemic wound down, remote work was gonna reduce significantly.

In the, I called it five to 10-year window, but probably not 10, maybe a five to seven-year window, we were gonna see returns aggressively towards pre-pandemic in-person work, and then I had a more speculative prediction that that was then gonna shift again, maybe seven to 10 years in the future, where we were gonna see a new breed of company that was native remote, using ideas that were spawned by companies that innovated during the pandemic, these were gonna start to rise and spread new methods of remote work, and we were gonna see a return back towards remote work, so it's gonna be a up the remote high, back down towards in-person, and then a sort of slow gradual shift towards a more advanced and sophisticated approach to remote work in the future.

So I had this whole theory about it, I wrote an article in "The New Yorker" about it a year or so ago, where I espoused this theory that was first proposed by an entrepreneur named Chris Hurd, H-E-R-D, this theory about tech companies that started during 2020 and 2021, were gonna figure out from scratch how to be remote really well, and it would take about five to 10 years for those ideas to spread to other industries and larger companies, and then we're gonna see really stable remote companies, but in the short term, my prediction was we're so bad at remote work because we let the hyperactive hive mind rule our collaboration strategy, and when you take a hyperactive hive mind controlled company and makes it remote, a lot of friction arises, and people work more, and they're in Zoom all day, and email goes out of control, that we were gonna end up having to stumble back to in-person work.

All right, so we can look at the data, how would we grade my prediction? Where are we now? About maybe a year to two years out, depending on what timeline we're going on for when I first started making these predictions, and according to this research here, the office occupancy has hit a post-pandemic milestone of 50%.

This, I guess this would have been in January. All right, so that is a non-trivial return towards in-person work, like I predicted. However, according to this article, experts say this could be the new normal. So in other words, the experts cited in this Washington Post article say, "But we're not gonna get higher than this." Got two points here.

One, if they are correct about that, I would give myself maybe a B. I don't know what you think is fair here, Jesse. We did for sure return significantly towards remote work. I think this number was down in the 30s at their nadir in the summer of 2020. And so we've gone back to more than half of them.

So we could say the majority of companies are now in person, but we're not 80%, we're not 90%, which is the numbers pre-pandemic were very high. There was not as much remote work going on. So I would maybe give myself a B if these numbers were accurate. My second point, I don't know that that prediction is accurate.

So I have a graph on the screen here from the article. It looks like, okay, I was wrong. The nadir was actually, looks here like 15% in person. And this would have been in 2020, the spring of 2020. It looks like it's been raising pretty steadily. And there's a pretty steady line raising this 50% higher than any other time before.

I think these experts might be a little bit too quick to say this may be the new normal. And I believe it's probably from bias. I think for certain sectors of our economy right now, especially those who are involved in sort of elite discourses, elite media discourses, or elite academic discourses, an idea took hold in the last year or so that remote work was a progressive labor policy and was in some sense, the only humane way to run knowledge work.

And the very idea that someone would want to run their office in the way that we've been running offices basically until yesterday. So for decades and decades of yesterday, the very idea that we'd want to do that again is itself contemptible. So there's this strain of thought that has now associated remote work with this is obviously the thing that we should be doing and is almost aghast, if not completely flabbergasted that anyone would not just let their employees be fully remote.

So I think from that mindset, which by the way, I'm not fully dismissing. I wrote this whole New Yorker piece that tried to understand where that came from. And I think there's deeper layers underneath supporting that, that are worth unpacking that we won't do that now. But if that is your mindset and that's what you're seeing on Twitter, and that's the conversation you see in the Washington Post every time you open it up or in the New York Times, if that is your mindset, I think it's hard to believe that the number would keep going up.

You're surprised it's even at 50. So you say, well, surely it would go no higher than this. And this is essentially what the expert quotes, at least by my ear, is what it sounds like in here. It's not like there is evidence for a significant slowdown and we're reaching a derivative of zero now on this graph.

If you look at what's going on here, the experts are just saying things like, it's unlikely to go much higher because flexible work is becoming entrenched. Some employees have resisted hard mandates. It's just sort of, hey, we're used to this now. I can't imagine it's gonna go higher. So I don't know, the reality I bet is probably higher than that, but still probably not as high as I predicted.

So we can put aside whether that's good or bad. I've tried to take a relatively value agnostic stance in my predictions. So when I'm trying to predict what I think is happening, I just wanna try to get it right. Whether it's good or bad, what's gonna happen, that's a separate strain of argument, which I have other thoughts on.

But I think we have a little bit more in person to go going forward. And again, my argument for why that is the case, and I'll just take this one piece of my argument and rearticulate it one more time. If you do not have good processes or systems for collaboration, if you rely on ad hoc unscheduling back and forth interactions to get things done, remote work makes work harder.

You get rid of the incredibly efficient impromptu let me grab you after a meeting or in a hallway type discussions. You lose transparency in the people's workload or evident exhaustion. You break down the boundaries much more severely between at work and not at work. You get rid of that commute time, psychological phase shift that helps you shift from work to at home, increasing burnout, increasing stress.

A lot of remote knowledge workers are not working less. If anything, they're working more, even though there's less physical surveillance and they don't have to spend time to commute. So there's a lot of issues with just taking bad collaborations styles and then moving them remote. And so my prediction is that friction was gonna bring people back because it just works a little bit better.

That doesn't mean remote work is not a good idea, but it has to be done with much more structure and strategy. And that's what I think is gonna arise five, six years in the future. That's being worked out now and this sort of remote work V2, that is gonna have it spread.

It's gonna be a little more gradual and we'll have a much more sophisticated approach to remote work than simply just do what you were doing, but now we're on Zoom a lot. So that was my thoughts on that. And I think I'm, according to this article, have a B, if trends continue the way I think they might, maybe I'll edge myself up to a B plus.

So we'll see. But I wanted to take advantage of this topic and say, putting aside what's gonna happen in the future, let's talk about what we can do with what we have right now. So if you were one of the 50% or more of knowledge workers who is working remote right now, let's take this reality out for a little bit of a spin.

I mean, what are we experts on here in this show? One of the things we're expert on is really understanding how work unfolds and then building very intentional or intelligent systems to allow us to take advantage of these realities, to take control of our work and our workloads and how things unfold.

Working remotely in theory massively increases your flexibility and autonomy if you're able to take advantage of that. And so I figured, let's look into that a little bit. Let's look into how we can hack a remote work job with the goal of significantly decreasing the amount of time you work.

So that's today's deep question. The deep question we're gonna explore today, how can I significantly decrease the footprint of my remote job without anyone noticing? So like always, we'll deep dive on that question. Then in the second segment of the show, we're gonna do five questions from you, my listeners, that all relate to this general topic of today's episode.

And then the third segment, we'll do something different. And today that's gonna be me reviewing the five books I read last month. All right, so that's our goal. You know, Jesse, I'm not the first to do this. This was at the key of Tim Ferriss' "4-Hour Workweek," 2007 bestseller.

"4-Hour Workweek" gets into how do you shift your job to remote? And then once you're remote, how do you best take advantage of the potential flexibility there to build something really cool? And I think what Tim was right about, and this is influencing what I'm talking about today, is that it's actually non-trivial to take advantage of that potential.

It's not just because my job is remote, suddenly I'll have more flexibility, autonomy, and things will be better. It's actually hard work to take advantage of the potential for the remoteness to make your job better. So in some sense, we're upgrading Tim's original thoughts from 2007 to the reality of 2023 knowledge work.

All right, so I have two points to make before we get into our tactics here. Point number one, what do I mean when I say significantly decrease the footprint of your remote job? Here's the definition I wanna use for the sake of today's discussion, that you've reduced the time you spend on your remote job enough that you could, in theory, fit a significant second endeavor into your standard work hours.

Right, so that's what we mean by significantly decrease. What are examples of the type of significant second endeavors that you could put in? Well, there's always what we've talked about on the show before, the phantom part-time job. This is where you're essentially working on something else at the same time that you have your normal job.

You have some side hustle that you're putting some time into. Now, we've gotten feedback on this before that in a lot of professions, there's some ethical issues around that. But for a just in case, or for instance, I think this is a good example of the magnitude of time we're talking about saving here, that significant, significant second endeavor could be a personal pursuit, something very important that you're doing in your own life that is non-professional.

So you are rich role style while he was still a lawyer and training to do his Iron Man endurance events, right? Or you're building a massive animatronic Halloween display that's going to move and walk down the street just bringing this up from a friend. That's definitely not my intention, but something that takes a lot of time.

I've seen some of these guys on YouTube. It could also be just, you want a lot of cushion because the pandemic was exhausting and you have young kids and you just wanna be able to like Ginny Odell, just sit outside in a garden for a couple hours on a semi-regular basis, because we don't have to be pushing it to the limit all the time that exhausts us as humans.

It could even be mastering a new skill that is relevant to your current job. What I'm gonna do is free up a lot of time, which I'm gonna use to master the skill that if I bring it to my current job, then I'm gonna be really killing it, right?

I am going to learn this advanced machine learning, modeling language and come back with the ability to completely overhaul the way our client recommendation systems work. So this is gonna take me months of study and it's gonna take a lot of time and I can do it because I freed up a significant amount of time.

So that's what I mean, that's the goal. That's how much time I wanna talk about freeing up here. Point two, this is not quiet quitting. Quiet quitting reduces the time and the amount of things you get done. It reduces the time you spend working by disengagement. It says, you know what?

I'm working too hard and so I'm gonna work less hard because I don't owe you work that's hard. I don't owe you that magnitude of hard work. So quiet quitting is you pulling back essentially what it is you're offering to your employer. As you'll see with the advice I wanna give, this is actually quite different.

We're gonna be squeezing out inefficiencies. We're gonna be squeezing out wasted time. Time waste that was injected into your life because of the negative externalities of remote work that when you reclaim that back, you're not actually reducing the amount of useful work you're able to do for your employee.

You're just reducing the amount of time that same good work requires. So this is not about you saying, wait a second, I'm giving you too much. I'm now gonna do less. You know, what are you gonna do about it? It is, we are doing this poorly. If I get rid of the wastage, I'm still getting the same work done, but I'm done at two.

So I'm gonna build a giant animatronic Halloween display outside of my house. All right, so those are my two points. All right, so given those two caveats, I have a collection of ideas here. Let me look at my notes, five ideas. If you're a remote worker, how to significantly decrease the footprint of your remote job without anyone noticing.

All right, idea number one, create synchrony traps. Now this is new terminology for an idea that you hear in different forms all the time in this show, but it is a critical idea nonetheless. Your number one enemy to significantly decreasing your time is the need to have to monitor back and forth communication throughout all your business hours.

So if the way your collaboration unfolds is through back and forth Slack and email, it is very difficult, for example, for you to stop work at two to go work on your giant animatronics because there's all of these ongoing conversations that you keep having to dip back into. In fact, you probably have to keep dipping back into those beyond normal work hours and into the weekend.

So we have to kill as much as possible the need to have these unscheduled back and forth conversations at the core of your collaboration. You need to defer these asynchronous conversations to easy to access synchrony. A few ideas I've mentioned before, number one, office hours. You know I'm a huge advocate of this.

Every day this hour, my phone is on, Zoom is on, I monitor this very specific Slack channel. It's like my name, office hours. And you just tell people as soon as an email or a conversation looks like it's about to instigate a long back and forth discussion that's just gonna happen asynchronously and haphazardly, you say, let's get into this.

Any one of my upcoming office hours, just swing by, shoot me a call, jump on Zoom, and we'll go back and forth and figure this out. You could probably defer 50% of what would otherwise be ongoing asynchronous conversations. 50% you could defer to these pre-scheduled office hours and dispatch with them.

And again, if we wanna clear up a lot of time, we have to concentrate when this interaction happens. Standing group meetings is also important. This is an idea that's adapted from agile methodologies where they have this standing meeting every single morning. You don't need that, but if you work in a team or a group, have twice a week, a standing meeting, one hour long, where you deal with all your group issues, and you should have a shared document where people write down as it occurs to them, things that need to be discussed, decisions that need to be made, questions that need to be answered.

They write it into the shared doc. And when you get to your next standing group meeting, you just go through that thing. All right, I wanna ask you about this, and what about this? And what are we doing about this? Can we check in on this? And I'm worried about that, and what happened to this report?

And who's working on this, and what do you need? And everything gets taken care of. That's like another 30% of your otherwise asynchronous haphazard back and forth email conversations. Another 30% are out of your inbox, out of your chat channels, if you have a standing group meeting twice a week.

Finally, ad hoc processes. This is the core idea in my book, "A World Without Email." Collaboration happens on a regular basis. You should have a process that everyone agrees on, and everyone will have a part in constructing that explains how information moves, and how you communicate, and prevents you from having to have unscheduled messages.

So if something happens a lot, you eventually have to bite the bullet, and figure out that system where there's a shared spreadsheet, and you update the cell when you've updated the file, and the file goes into Google Drive somewhere, and on Wednesdays is when the designer takes the file, and edits it, and whatever.

You figure out those processes that prevent you from having to wait until a message comes in, and then send a response. So synchrony traps, critical. All right, idea number two. Control your meeting availability. You are still, in most knowledge work jobs, even after you put in place sufficient quantity of synchrony traps, are gonna have one-off meetings.

Hey, we need to talk about this new initiative. This client wants to have a conversation. Your boss needs to go over the new marketing request. I mean, these one-off meetings are, of course, unavoidable. If they can just metastasize all over your schedule, all over the place, that is the other major killer of the ability to reduce the footprint of your job.

You'll wanna leave at two to work on those animatronics, but there's always that stupid three o'clock meeting that shows up. So we have to control the meetings, but we have to do so in a way that does not make you seem like a time miser or a curmudgeon, because that just annoys people, and then they're gonna throw more meetings at you just because you're on their nerves.

So how do we do this? How do we control when our meetings happen without being annoying? You become overly helpful in setting up meetings. You have a scheduling system that's incredibly easy to use, and all of your availabilities are in it, and you just have to click a button, and you're good to go.

That meeting, you'll be there. That meeting is booked. And you act incredibly felicitous when people ask you, like, "Hey, can we do a meeting?" You're like, "Of course. In fact, I have all of my availabilities in this system." You just, any time that works for you, you just click on whenever it's gonna work best for you.

And if you need to coordinate with Bob, you guys just pick any of these things. I'm open all these times. I wanna, let's definitely meet. I've got the best system. I'm Mr. Bring me to a meeting. Here's the thing, though. You control, then, what those available times are from the outset.

So then you seed this meeting system to keep major swaths of your day protected from meetings. Now, what you have to do, and here's the stealthness, if you're too consistent, if it doesn't look sufficiently random, it will attract a red flag. So if you say, and this is a simple rule, meetings until one, no meetings after one, because I'm training for my marathon or building my Halloween animatronic, that's too noticeable of a pattern.

So now I'm your boss. I'm always suspicious people are trying to pull one over on me. And you say, "Oh yeah, please, I'd love to meet you. Pick a time." You say, "Wait a second. Every single afternoon has no times. I call shenanigans. I am in meetings in the afternoon.

You should be too, you know, what is this?" So what you do is you take two days and you flip it. So maybe Monday, Wednesday, Fridays, you only show availabilities in the morning. Tuesday, Thursdays, you show availabilities mainly in the afternoon. You throw a rogue meeting here and there.

Maybe on a morning where you're not scheduling meetings, you throw a rogue one kind of later in the morning. That looks sufficiently random that it's, "Hey, this guy's got a lot of availability and there's no particular pattern here." But you are absolutely controlling it. So by taking control of getting out in front of, "I wanna schedule this.

I love it. Let's meet. I love meetings, you know, and here's all my availability. I'll just show you for the next month." And you just choose all the times you want. It actually gives you, ironically, allows you to way reduce the impact of meetings if you make it easier to schedule one with you.

All right, idea number three, you really have to sell processes. So we mentioned this in the synchrony trap that any type of collaborative work you do regularly should have some sort of system or process in place. Well, idea three says you should really focus on selling this to the people you work with.

It is easier to just rock and roll on email and Slack. In the moment, that is always easier because if I just type this nonsense, ambiguous soup of email annoyance and hit send, this may be injecting, you know, a syringe full of headache into everyone else's life for the next week, but in the moment, it gets the thing off my plate.

It's out of my mind. You know, it's, "Uh, client bad meeting. No good thoughts, question mark, lol, emoticon, send." And like that thing is out of my head, even though I've just created a huge headache for everyone else. 'Cause like, I don't know what to do with this. I mean, are we gonna do a meeting?

When are we gonna do a meeting? What's the actual issue? And so it's always easier for everyone in the moment to just, let's just rock and roll on Slack, come on. So you have to sell processes as an alternative. You gotta get buy-in from people. Let's work on this together.

Here's what I think. If we use the shared doc and agree that Wednesday nights is when we review the documents, whatever. You gotta get buy-in from everyone involved. Make it seem like they were a part of that process. Do not just come in and say, "This is what we're doing now.

This would be better." Don't brandish my book and just say, you know, "Father Cowell says that we should use Trello." Get buy-in. That's part of selling processes. Two, offer escape valves. Psychology 101. People are worried about processes that move them away from the hyperactive hive mind because they will come up with scenarios.

Hey, we have this system now where we process client requests on Tuesdays and Thursdays. But what if a request comes in on a client on Monday that says, you know, "I'm being held hostage by a terrorist that has surrounded the local orphanage with a bomb and will explode it unless within the next hour we get responses to this doodle pool." And they're really worried about these scenarios.

And if we have to wait till Tuesday, the orphanage blows up and all the kids die. So what you do is you say, "Yeah, but we have an escape valve. Here's my number. It's my cell number. It's with me all the time." You just call that if there's something that we can't -- we have to get out of the process.

Something is urgent. We gotta get out of here. You just call that number and I'll answer it. You don't have to worry. We will save those kids. They will never call it. No one wants to call, like, "I'll just wait till the next meeting." But it gives psychological cover.

Even if something bad happens, this process won't force us into an unforced error. So escape valves are a great part of selling processes. So you don't just need alternatives to the hyperactive hive mind. You got to put in a lot of effort to sell them to the people around you, the people who are going to use them with you.

All right, idea four, trade accountability for accessibility. All right, so this is where you are essentially making a trade, and it's not a costless trade. There's some risk here. But you're making a trade with your employer where you say, "I'm going to work on this important thing. My success or failure on this effort is going to be easy to measure.

So if I fail, you know it, and we'll have a problem. But if I succeed, it'll be good. And so I will be accountable for this, but you're going to have to give up some accessibility. I'm going away to work on this big, important thing. And if I fail at it, then maybe I'm going to have some issues at this job.

But as long as I'm succeeding, you're going to let me go off and do this thing." So one of the nice things about the alternative of just being plugged into the hyperactive hive mind is you don't really have that accountability. You have the sense of stability. As long as you're willing to just, I'm in here, I'm jumping on Zoom, I'm doing doodle polls, I'm answering emails in Slack, and it just seems like, look, Cal is here, he's busy, he's always involved in things.

So I guess he's doing fine. Like your job feels secure. When you instead say, "I'm going to give that all up, but hold me accountable on actually producing something that sells," you're leaving the obfuscating comfort of the hyperactivity to make you and your activity very clear. And you're trading that.

You're trading the risk involved in that for less accessibility. So a couple advanced tips about how you trade accountability for accessibility. This is often a good parry of a potential promotion. So if you've been doing really well, maybe you've read my book, "So Good They Can't Ignore You," and you're deliberately practicing and building up career capital.

If you've been doing really well and like, "Look, we want to promote you. Like, you're killing it." That's a great time to parry into an accountability play. You say, "Actually, I don't want to move up to the next level and put up to three people working under you." That's an OfficeSpace reference for those who recognize the movie.

You don't want to move up and have more responsibility, but you do want to get some return off of this career capital that you've acquired. This is a great parry. No, I don't want to take that next management role. What I want to do instead is really focus my attention on this type of work that we do, and we'll set up a one-on-one relationship with one particular supervisor.

I'll check in every week, and here's how it's going to happen. And you've just freed yourself from the normal flow of seven different projects and all the different meetings and communication that comes with it. Another advanced tip ties extra salary to performance. So it's a way of saying, "If I do really well, I get paid better." That's a better way for your salary to go up in some circumstances than instead just, again, doing a generic promotion where you have to, I have to work up this ladder and have the salary increase with the hyperactivity of my life.

Instead, you say, "If I kill it, I'll kill it in my salary. And if I don't, I might have a tough year." People like that. They feel like skin's in the game. Somehow from the employer's perspective, risk seems mitigated. Advanced tip number three, you might even consider the management consultant schedule.

So the management consultant schedule is typically you're on site Monday to Thursday, and then you're back at the mothership office on Fridays. That's what if you work at McKinsey, for example, is what your schedule's often like. If you've made one of these plays, I want to trade accountability for accessibility, this could be part of what you offer.

On Fridays, I'll be around at the office. Any type of meetings that need to happen that might be tangentially relevant, like we can do them on Fridays, you can come chat with me in my office. I'll be there on Fridays. But Monday through Thursdays, don't really expect much. I'm working on whatever, building out the new marketing engine for our Halloween animatronics.

Leave me alone, but I'll be here on Friday. So you might even suggest a very specific schedule of accessibility, make that all really plain. All right, now idea number five for significantly decreasing the footprint of your remote work job, crush one thing per month. Systematic, deliberate, relentless, deep work day after day, maybe just one or two hours a day on something really valuable.

So on a regular basis, you're actually producing something great. Why is this important for gaining more time? Because you get so much breathing room. They give you so much rope to work with when you're crushing it. When you're producing really great stuff, you gain much more autonomy over how your job unfolds.

If you're, by contrast, unreliable, if things fall through the cracks when they hand them to you, if you haven't really done anything of note in the last two or three years, you're under suspicion, and the leash is gonna be tightened. And every time you're late answering an email, every time you go an afternoon without them hearing from you, they get more and more worried and suspicious.

And what is this guy doing? Is he building animatronics? What's happening here? But if you're crushing it every month, they're like, this is great, Cal's on it. So ironically, by working harder, at least on one project a month and giving intense attention, you can actually reduce the total amount of time you have to work.

My friend Adam Grant, the Wharton professor and business author, calls these idiosyncrasy credits. If you do things really well, you gain the ability to be more idiosyncratic about how you work. If you're not doing things really well, you lose those credits. And so if I'm super valuable, and I wanna focus on just one area and only come in on Fridays and have these weird processes for the few other things we do, if I'm killing it, like whatever.

If I'm not, you say, yeah, right. So you kinda earn your way, you'll work your way into working less. Now, I think the issue people often have here is they do the first part, they work really hard and do the really good things, but instead of using that as leverage to take control of their career and shape it towards what resonates for their full life, they just say, great, now I'll work even harder.

Well, this will give me the next promotion and now I'll have to do even more hard work. And they just ratchet up, ratchet up until they're completely burned out. So you can't forget that second part. Once you do something really good, become so good you can't be ignored, you gotta take that out for a spin and say, what do I want?

Not just what more will this earn me? How much more money can I make? How much more prestige can I gain in just being promoted? You need a much broader view, not when things are going bad, but when things are going well. I think that's something that people often miss.

I suggest to you, those are my five ideas. I'll say all five names again. Create synchrony traps, control your meeting availability, really sell your processes, trade accountability for accessibility and crush one thing per month. You do those things, if you're one of the 50% who has a remote job right now and you can, if you want, significantly decrease the number of hours during the standard workday that you're spending actually dedicated to that job.

- That's really solid advice. Well, I got a lot. - It's interesting, Tim's book, what he focused on, and I talked to him about this when I interviewed him for his show. So I interviewed him and then we aired that on his show. One of the things we talked about is that section of his book got really out of date for a good reason.

Most of the advice is how in the world are you gonna convince someone to let you work remotely? That was like the challenge in 2007. How in the world am I gonna convince someone to let me not be in the office? Today, that's not the problem at all. That's, if it's not a default, it is obviously now a very well understood mode of work because two years ago, according to that graph, 85% of people were working remote in the knowledge sector.

So that whole challenge of how do I convince people that remote work is even feasible, that whole challenge has been solved. And so now we can actually put all that planning and hacking energy into, so what do I do with the remote job? So we're making progress. - And then establishing the front end with the definitions was helpful.

- Yeah. - To grasp it all. - Yeah, like what are you actually trying to do? - Yeah. - Yeah, yeah. What are the, what do we mean by this? What do we, yeah, so there we go. I don't always do hack stuff, but I feel like we haven't done some hacks in a little bit.

And I figured let's get in there, hack the job. All right, so what we're gonna do in the second segment of the show is I have questions from you, my listeners, all about this, all about figuring out how to maneuver remote work to be more towards your advantage. So we can see real life examples of this advice and similar issues at play.

First, however, I wanna briefly talk about one of the sponsors that makes this show possible, and that is BetterHelp. So this show is sponsored by BetterHelp. Now we talk about often on the podcast about the five areas of your life, what we call the deep life buckets. You have these five areas.

You need to concentrate on all five to have a fully deep life. I sometimes feel like there should be a sixth, cognitive hygiene. If you aren't building, we could think of it as an amicable functional relationship with your own brain, your efforts in the other five buckets of the deep life are gonna go for naught.

If you're wracked by anxiety, if that anxiety has developed into depression disorder, if there's other types of issues or compulsive thinking, it makes it very difficult for you to enjoy other parts of life or make progress on shaping other parts of life to be truer to your values. So cognitive hygiene really should be also one of the buckets that you care about in forming a deep life.

A therapist is like a highly trained physical trainer for your mind. It is an expert that can help you figure out how do I actually live with this wondrous, catastrophic, wonderful, terrifying thing that I call my brain. Therapist is like your trainer, your expert to help you build that relationship with yourself.

This is where better help enters the scene. If you've always thought about this, like maybe I should talk to someone, but again, it seems daunting. I mean, where do I find this person? I've heard that it's very hard to find therapists right now because after the pandemic, they're highly in demand.

Better help is your way into this world. So if you're thinking of giving therapy a try, better help is a great option. It is convenient, flexible, affordable, which is no small thing. And here's their big thing, entirely online. You just fill out a brief questionnaire to get matched with a licensed therapist.

You can even switch therapists anytime you like for no additional charge. So if you wanna live a more empowered life and get that cognitive hygiene, deep life bucket into shape, therapy can get you there. Visit betterhelp.com/, what's our slash here, Jesse, deep questions? - Yep. - Deep questions. To get 10% off your first month, that's betterhelp, H-E-L-P.com/deepquestions.

Don't forget the slash deep questions so they know you came from me. One of the sponsors I wanna briefly talk about is ExpressVPN. As I've explained before on a show, a VPN is a critical tool for anyone who uses the internet. It is a tool that allows you to interact with the internet with privacy and with security.

How this works is instead of just going to the service or the website directly that you wanna talk to, you instead establish a encrypted secure connection with a VPN server. You tell that VPN server through this encrypted secure connection, this is the website I really wanna talk to. This is the service I'm really using.

And then the server goes and talks to that site and service on your behalf and passes the response back to you through your protected connection. Why does this matter? So people can't see what you're doing. So let's say you're on a wireless access point at a coffee shop somewhere.

People who are sniffing your packets out of the air, all they know is Cal is talking on an encrypted connection to a VPN server. They have no idea where you're going. More importantly, your phone carrier or your internet service provider are allowed to and probably are keeping track of what sites and services you're using, potentially even selling that information to advertisers.

If you're using a VPN, they're out of luck. All they learn about you is he was talking through an encrypted connection to a VPN server. I have no idea who that VPN server was talking to. So as a computer scientist, I can tell you, you should use a VPN.

And if you're gonna use a VPN, use the one I use, which is ExpressVPN. They've got the great server coverage. They've got the great bandwidth available and they have the really easy to use app, which means you just click a button and boom, it's on. You don't even realize you're going through a VPN anymore.

So use ExpressVPN if you're gonna use a VPN. To find out more, go to expressvpn.com/deep to get the same VPN I use. So take back your online privacy today and use my link to get three extra months free. That's E-X-P-R-E-S-S-VPN.com/deep, expressvpn.com/deep. All right, I am excited. We get a lot of questions about remote work, Jesse.

So I am excited to get our hands dirty with some real life remote work situation and see if we can help make people take advantage of that situation and make their work life a little better. What's our first question today? - All right, first question's from Ian, a 35 year old engineer from San Francisco.

My family has the opportunity to make a cross country move next year that has a potential to radically realign our lives closer to our values. More time with children, each other, out in nature. I'll be shifting to a full-time remote work in my engineering role. Any advice on how to navigate this change with reverting back to our old, busier ways?

- So Ian, what I think is critical here is you are recognizing just the fact that your new job is remote does not mean that automatically it is gonna be a lot of flexibility and autonomy and you're gonna be able to spend a lot more time on the other things you care about.

Remote work gives you that potential. Harvesting that potential is your job and it's hard work. So go back, for example, to the five ideas we talked about during today's deep dive and give those serious consideration that is the type of concentrated effort you'll need to shape this new role into what you want it actually to be.

Two other things I wanna mention beyond that deep dive, two, you might consider this change of job as a good opportunity to renegotiate your role. So we talked about during the deep dive that a promotion, for example, was a good time to renegotiate towards an accountability versus accessibility type shift.

So gaining more accountability to lose the need to be so accessible. I'll be more remote now. I'm away from the office, so I'm gonna be harder to reach, but you really are gonna hold me accountable for the big projects I'm working on. A move to a new remote position is a great time to make that type of shift as well.

The second point I wanna make here goes a little bit off book because I'm drawing from the full version of your question. And in the full version of your question, you mentioned that your spouse is a professor at an R1 research institution. So this move is actually being driven by your spouse going to a new academic job.

So that's an in-person job. So you shifted remote so you could follow them to that job. They're at an R1 university. If your interest is, and I'm reading this here, to spend more time with your children and with each other and out in nature. The other thing I would suggest as soon as you're making this shift, and this is a little bit of insider baseball for non-academics, but I think it's important, is set your cost of living such that your spouse does not have to take summer salary out of grants.

I made this shift three or four years ago, and it was phenomenal. And you guys, I want you to try the same thing. So what this means for people who are not academics is most research positions at an R1 research university, if you're a professor, they'll pay your salary for 10 months.

The other two months of the year, typically June or July or July and August, that's your summer months. Now you can either not get paid during those months, or you can get research grants where part of the money in your budget for that research grant is to pay your salary in those two months.

If you do not do that, if you do not ask for summer salary in your research months, you basically have that time to yourself. No one is paying you, and so they cannot expect much of you. And you'll see this, universities are pretty good about actually following this. There's not meetings and committees and things happening in the summer because that's your time.

So that's my other suggestion. If you are following my advice, Ian, and gaining a lot of flexibility and autonomy and significantly decreasing the footprint of your remote job on your life, if your spouse can do this with his or her summers, you combine those two things, and it's gonna unlock all sorts of cool adventures or way more time together with your values during those summer months.

So that's an extra bespoke hack that I wanna add onto your shift that you're doing here. All right, let's keep rolling. - All right, next question is from Catherine, a 33-year-old office manager. I'm the office manager at a small remote company. As the office manager, a lot of my work is reactionary, involves being available for people most of the day.

For instance, my boss is pinging me anytime something comes to mind. How can I practice deep work at my job? - All right, well, Catherine, first of all, I don't know if deep work is the right thing to be talking about here in the sense of an office manager position might not require regular extended periods of unbroken concentration.

It's not really in the job description. That doesn't mean, however, that you should be forced to sacrifice yourself to the travails of the unbridled hyperactive hive mind. So in my book, "A World Without Email," I talked about this specifically. I broke knowledge work jobs up into multiple different categories.

And this was one of the categories I talked about. I called it support, but mainly what I meant by this is the major part of your job description is reacting to requests to come in and trying to satisfy them. And what I said in email, the goal there is not to get very long periods of time where no one bothers you.

The goal there is to achieve a workflow in which you can execute one thing at a time without interruption. So I'm doing this thing someone asked me to do fully until it's done. And now I can expose myself to, okay, what else is going on? What am I gonna do next?

And then I'm doing this thing until I'm done. And then I shift on to the next. The alternative to this is what most people in these type of positions do, which is a constant background hum of tending to the back and forth conversations about the things going on or they're about to do while they're actually trying to do the work themselves.

And it puts you into this terribly cognitive fatiguing cycle where you're trying to actually execute the tasks that are coming to as the office manager while context shifting like a madman while you're executing the task because you're keeping up with these conversations about other things going on, your brain gets completely fried because it can't shoot back and forth like that.

And the job becomes exhausting and you burn out. So we don't need four hours every day for you to work on your novel, but we need you to have the ability to work 40 minutes on getting this report together before you look at any inbox, before you look at any Slack.

So one thing at a time, completing it before moving on to the next. That's how our mind is wired. That is what I want to achieve for you. So Catherine, I'm gonna get super tactical here 'cause it's kind of the mood we're in, I think for today's episode. And I'm gonna, took some notes here.

I'm gonna walk through how you can essentially simulate without any extra visible technology, how you can simulate something like an informal ticketing system that help keep track of all of this incoming in a way that allows you to actually be sequential in how you exercise. All right, so here's, I'm gonna walk you through this.

Set up a task board using a program like Trello. This is gonna be the base of your informal ticketing system. Here are the five columns I want you to add to that task board. To process, ready to execute, scheduled to execute, waiting to hear back and done. Now, here's how you're gonna go forward.

You will check inboxes, be them email, voicemail, if people still use that or Slack, in between tasks, but never during a task. And if a task is very long, well, then you need to break it up into reasonable size. Like I'm gonna break it up into a chunk that'll take about 30 to 45 minutes.

And that's one task, okay? So you're never too far from checking in, but you're not switching away from what you're doing, checking and switching back. So you're only checking in between reasonably sized tasks. Things that come into your inboxes, you are going to immediately get them out of there.

Your email inbox is not a knowledge management system. It is not a task management system. It is a literal mailbox. You gotta take the mail out of there and put it somewhere else. So for you, what that's gonna mean is when you do these checks, you're gonna move everything out of there to a card on your to process column in Trello.

And you can even just copy the text of the email and paste it on the back of the Trello card. So all the information is there, quick summary of what's going on on the front. You don't have to make sense of it. You don't have to make a plan for it.

It's in your system. It's no longer in your inbox, all right? So you're constantly grabbing things in between tasks, adding to your to process column. They're gonna play the role of a ticket here in our informal ticketing system. All right, now what you need is regular sessions throughout each day.

I would say maybe two, one mid morning, one mid afternoon for working through those process columns. I would schedule this time on my calendar, give yourself about 45 minutes for each of these sessions and schedule on your calendar and protect it. Maybe at 10 and three. As you go through everything that's built up in the to process column, you have a few options for each item.

If it's a very quick thing, someone has a question you can easily answer or you have to just go on their behalf and whatever, add their requests to buy paperclips to the list you keep of what to buy in your next order, just do it, move that card to done.

If you need more information from the person who sent you the request, which is often the case and part of what makes the support roles really annoying is that the people you work for, the managers are often, me need pewter good and just send, you're like, I don't know what this means.

They're just trying to get it off of their head using you as like a reminder system, very frustrating, but it happens all the time. So you need more information from the respondent. You can request that they clarify maybe by calling you during office hours. Remember office hours, I always come back to that.

If you run, if you're an office manager, you should have probably twice a day office hours. You say, yeah, just call me, blah, blah, blah, at any of these days, and we'll figure out in more detail what I can do for you. It's all about how I can help you.

You gotta play that, you gotta play that game. Or if you need to send a request to someone else to answer their question, they're asking you me want computer good. So you have to talk to the IT department about the computer replacement cycle. So if you have to request something else on behalf of them, you're gonna move that card to the waiting to hear back column.

And you just write right there on the card under the description of what it is, who you're waiting to hear back from. I asked Jesse to stop by office hours at some point and clarify the question. I sent this request over to IT on Monday, waiting to hear back.

So you have it, lost it. It's not in your inbox, it's not in your head. It is right there. The other thing that you might be doing as you're going, the other options you're going through this to process column is clarifying specifically what needs to be done. So again, you're translating from the informally type thing into here's what really has to happen.

A request has to go over here and then we have to file this form, wait to hear back. You're clarifying, okay, this is specifically the work that needs to be done here. And so for complex tasks that are in the two process column, this is what you're doing with them.

You're clarifying what really needs to be done. If it is something that needs to happen on a specific day, put it on your calendar, move the card to the schedule to execute column. If it's something that's big enough that it doesn't have to happen on a particular day, but if you don't put aside time for it, it's not gonna get done.

Go schedule that on your calendar. This morning, this afternoon, I'm working on this big request that came in and move the card to schedule to execute. Otherwise move the card to ready to execute, which is just things, do them next time you get a chance. You know, you clarified what it is and it's do them next time you get a chance.

In all cases, this is what really simulates a ticketing system. Whenever something moves from one column to another, send the note to the original source of that task, keeping people up to speed. So that means when you first add something to two process, it's Jesse, I got your note.

It's in my queue, I'm gonna get to it. I'll keep you posted. So they know that you saw it. When you realize you have to ask IT something and you move it over to the waiting to hear back, hey, Jesse, just to let you know, I put in a request to IT, we're gonna figure this out.

I'll keep you posted and I'll let you know when I hear back. They know what's going on. If you move it over to, you know, schedule to execute, you can say, hey, I got your request. It's on my calendar. I'm tackling it on this day. I'll let you know when I'm done, right?

So you're always keeping people up to speed with what is going on. So that's the system. And then in all of your other time during the day, when you're not doing any of these things I just talked about, you're just pulling something off that ready to execute list and just doing it, send in an update.

You put all that together and you have something like an informal ticketing system. People are up to speed on what you're doing and what the status is. So they won't demand this minute to minute accessibility. Like, I don't even know if you got this. You better answer me right away.

You've gained yourself the breathing room you need to actually work on things until they're done before moving on to the next thing. This all might sound like a huge headache, a lot of overhead, but I'm telling you, Catherine, if you're able to work on one thing at a time with no interruption, if you're able to have captured everything that needs to be done and all the relevant information in one place, where you're not at all stressed about open loops or things you're forgetting, the cognitive drain of your job will be significantly reduced.

In fact, you might even actually rediscover some joy for, hey, I like this company. I play a key role in this thing operating. I'm valued by people. And I feel good about what I'm doing. You can get back to that if you achieve those properties. Now you don't have to use this particular system.

I just came up with these particular details. But my point is, this is what high-end elite knowledge work management systems look like. These are the type of things that you probably need in place if you have a high churn job. If you have a job where things are coming at you really quick and you don't wanna just completely burn out, this is what these systems look like.

There's not just one tool that's gonna solve this for you. You gotta engineer information flow and task flow and time flow. It's non-trivial, but this effort is worth it. These type of things make a huge difference once you get them right. It's like my old days, Jesse. The systems and hacking.

- Yeah. - That's like an old pitch you don't lose. It's like a knuckle curve. You asked me to build a system around information or task flows. - I'll do it. I love it. - Yeah. All right, let's keep rolling here. - All right, next question. Jason from Louisiana.

I've recently accepted a job as an editor at a major Christian publishing house. It's a remote position with autonomy and flexibility. I'm wondering what advice you have on how to balance this job while maintaining my own research and writing projects. - Schedule first reasonable time for your individual research and writing projects in a way that's not gonna grossly infringe on your normal jobs.

Don't say, well, from 10 to two, Monday through Friday, I work on my book. In the morning, the afternoon, you put it in reasonable time and build some good rituals around that. Where do I go and what do I do? Right before I start working. Then consider that time off limits and work around it for the rest of your job.

There's a little fixed schedule productivity. I write these mornings and it's one afternoon. Now I gotta figure out how to make the rest of my job work. And just use all the different types of ideas I've talked about. The same enemies that we talked about in the beginning, this shows your enemies here.

The more that all your work unfolds with informal back and forth, the harder it is to ever be away from it. The more that meetings can happen at any time at any place, the harder it is to get away from that. So you can put those type of ideas into the hopper, but just work backwards from, this is time I'm writing.

And so let me work around it. You would be surprised. This approach, which I call fixed schedule productivity, you would be surprised about how innovative it makes you. It's like my rule that I try not to work outside of a standard roughly nine to five or nine to five 30 work hours, even though I have nine jobs.

The power of just knowing this is my constraints and I make my work fit in those constraints has generated untold productivity innovation. So the simplest ideas can generate the most complicated responses. So just schedule that time, Jason, be reasonable about it, work around it. All right, what do we got?

- Next question is from Courtney, a 40 year old from the Bay Area. My remote software job has a lot of things I like, autonomy, flexible schedule, and pretty good pay. Now that I'm more senior, however, I don't feel like I have much room to grow. The only option would be going to management, which is a hundred percent hyperactive high mind and miserable.

Should I go back to the drawing board with a new career? - Well, Courtney, here's my follow-up. Why do you need room to grow? And I don't mean that to be dismissive or facetious. I actually think this is a common assumption that we should examine. So what I can tell from your question and the more elaborated version that you sent me is there's this baseline assumption that I need to be continually growing in my job, meaning salary, prestige, responsibility has to keep going up, much in the same way that economic growth has to continue or we're not gonna be able to pay back the loans that we just took out and the whole economy will collapse.

And so we often have this growth mindset around our careers. Now, this is a good mindset, especially early on. You know, when you're in a knowledge work job and you're 22, it's not a very good knowledge work job, right? And if you just said, why do I need to grow?

I'm perfectly happy in this entry-level knowledge work job. I'm very good at getting the coffee to my boss and Xeroxing or whatever. It's probably low salary, low autonomy. You don't have a lot of career capital. That's not so great. But when you've got to a point and in your 40s, you can get there, no problem.

When you get to the point where you have a lot of career capital, meaning you have a lot of leverage in your job and your essay and how that job unfolds, you can craft something that fits really well with your vision for the other bucket of money and buckets of your deep life.

Now we have to be careful about growth for the sake of growth. Now we're thinking about how does my work fit into my bigger vision of my life? And that might mean I need to get here. I'm here, but if I could get here, it unlocks all these other visions I have for these other parts of my life.

And then, yeah, then that's what we're doing. We're getting after that, figuring it out. But it might be with, this is great. I like my job. I'm good at it. It's flexible. It's autonomous. I like where we live. The other buckets, constitution, community, contemplation are all, I'm developing those.

I'm giving more time into those. Maybe my parents are aging and we live near them and I want to spend more time around them or have young kids or something. It's completely fine. I say, this job is great. I love it and it pays well and they like me.

And I don't want to go into management and I don't want to start over. Most employers are happy if you're like, look, I just want to kill it at this for a while. I have other things going on in my life and this is really good for me and let's just do that.

So I want you to consider that, Courtney. The good enough job, which is actually the name of a book that's not out yet, I don't think, but I blurbed it and I liked it. I read it and I blurbed it. It's called "The Good Enough Job", great title. Is sometimes the best option, at least for a while.

So I don't know if that's your situation, Courtney, but I'm using your question as an excuse to talk about this idea more generally. That the goal is not continual growth. The goal is building a deep life in which each of the buckets is humming close to whatever your vision is for it.

And so, especially for these sort of high-powered Bay Area engineering type jobs, people get there. They can get there by their late 30s, early 40s and have a lot of flexibility. So consider that, Courtney. Maybe that's just what you do for a while. I think your bosses would probably be ecstatic about it.

And I think you're right to not want to go into a management role at a job where that means 100% hyperactive hive mind. To me, that's the equivalent of it's a game show where someone says, "Look, we are gonna give you "it's Fear Factor. "We're gonna give you this bag with a 50% salary increase, "but we're also gonna kick you in the groin every hour." I'm not gonna enjoy the 50% salary increase if Fear Factor host Joe Rogan, who used to be a national kickboxing champion is kicking me in the groin every hour.

I think I'd rather just not have the 50% salary increase and keep my groin less kicked. This is a very important metaphor, Courtney, very precise. So sometimes getting a promotion can be Joe Rogan kicking you in the groin. That's what I'm trying to say here. That's what everyone has been trying to say.

They just haven't been able to articulate it as well. So keep that in mind. Do you need growth? Maybe just chill for a little bit. There's other parts of life that are cool as well. All right, we've got one last thing here. It's actually, it's a case study, not a question.

So occasionally someone will send in a question that I think is more, the question itself is actually just an interesting case study of the modern world of work and issues we care about. So I'm gonna read this one here. This is from Peter, a 35 year old software engineer.

So here's what Peter wrote. "I worked for a remote only tech company "where everything about the way they worked "was very intentional. "They embraced almost exclusively asynchronous deep work "from the CEO down with a particular emphasis "on only work on one thing at a time, "only have one top priority at a time.

"In many ways, it was great. "However, everything centered around "the company-wide project tracker "that served as a knowledge base, "a documentation layer, and a status tracker. "I could go read the latest draft "of the marketing company's upcoming blog post "or look at how the backend team "was tackling a new challenge.

"I tried to prune my intake, "but it became clear that the people that excelled there "were the ones that involved themselves "in many things at once. "These people were subscribed to many different initiatives "across the company and could inhale mass amounts "of constant project updates, "remember many of the little details "about where everything was.

"In short, hooking into the hive mind "was seemingly at odds with the one top priority mantra. "I used to think I was good at this sort of thing, "but somewhere between COVID and the birth of my second kid, "I seemed to have lost the ability "to keep tons of statuses in my head.

"I wanted to excel, but I quickly learned "that I couldn't keep up and ended up burning out. "This was all with a virtually free calendar "and lots of autonomy in my day-to-day work. "Should I have done something differently? "Should this company have structured "or encouraged something else?" So I wanted to use this as a case study instead of a question because it pointed out something critical about even an intentional remote work environment.

So we talked about how to make remote work work, get away from the hyperactive hive mind of things happening with unscheduled back and forth messaging. Tons of emails, tons of Slack, tons of meetings. This company that Peter's talking about actually had accomplished that. I think it's inaccurate. He referred to this behavior of inhaling information from the project management system as quote, "hooking into the hive mind." This is actually different than that, I think, Peter.

The hive mind to me is very specific about collaboration unfolding with these unscheduled back and forth messaging. So you have to constantly be keeping track of these things. This was a little bit different. This was making the ability to follow and be a part of many different projects low friction.

This is what was going on there. And this points out even an intentionally designed remote work company can fall into traps beyond the hyperactive hive mind. So the trap that is being illustrated here that I wanna just quickly highlight is controlling workload per project, but not the number of projects.

So you have a philosophy, and this I think is common, especially in tech oriented remote first companies. You have a mantra of one thing at a time, it's scrum boards. Like this is your task. And when you're done, you can pull another one in. That's all great, but then they don't restrict how many different projects you're involved in.

And it's up to you. And like, well, I could subscribe to this one. It's right here in the system. And this one, I could be involved in this one and that one. And no single project maybe has you doing more than one thing at a time, but you have seven projects.

And it's the same as having one project giving you seven different things to do, and you end up burned out. And if there is no systematic way to control your overall workload, then you're just thrown into a situation where it says, hey, it's up to you, but you know, if you're doing more projects, we're gonna look at you a little bit more positively.

And then what happens? The young ones with all their energy start to climb the ranks, and the rest of us, like Peter, who were exhausted by COVID and have kids at home, we fall behind. And then you begin to just create the split. And then all the young people, they get promoted much faster, and they start saying things like fire and cap and base, and they shift all of the operations to TikTok and everyone dies.

That's not great. So you have, this is a common mistake where you feel like you're a smart remote work company, but you're not. You control workload for project, but not project workloads. The other issue, this was not in Peter's message, but I'll just mention it 'cause I've heard about it a lot, is you get too obsessive about the details.

I think this plagued a lot of people who adopted agile methodologies like Scrum with their common task boards and standing meetings, is that because engineers like me are sometimes on the nerdier end of the social spectrum, let's say, we get obsessive. And then it's, what matters is as the third degree Scrum master on an alternative Wednesday, I have to roll 2D12 to see if we're able to advance the pull methodology one more layer towards the dungeon of despair.

It just becomes obsessing about the rules for the sake of obsessing about the rules. And then that's terrible too. So those are two traps that you can get away from the hive mind, but still be in a dangerous territory. So you have to control the overall workload, not just per project, and be worried about obsessing over the details of your systems.

They're just a guide to help you get away from constant back and forth. It's not the Talmud. We do not have to pour over the Scrum master guide to make sure that we're using the right terminology. All right, Jesse, so that's basically what I have to say about remote work and hacking remote work.

So again, if you're one of the people who is still remote, keep those ideas in mind. I like to end every episode with a something interesting segment. We do something different today. I'll report on the books I read last month. First, I wanna briefly mention another sponsor that makes this show possible.

That's our friends at ZocDoc.com. So this is pretty common. Let's say you have a health issue. You don't have an established relationship with a doctor for that type of health issue. Your foot hurts. You don't know a podiatrist. You don't have a primary care physician. How do you find a doctor?

A lot of people, especially people my age or a little younger, get stuck. Like, I don't know. I asked my friend. I walk down the street and look for one of those two snakes, Hippocratic snakes biting each other, and just say, "That must be a doctor's office." Like, we don't know what to do.

So we get stuck, and we invent annoying words like adulting to explain why we're not actually making progress. What's really happening is it's difficult. This is where ZocDoc comes in. It is a free app, in fact, the only free app that lets you find and book doctors who are patient-reviewed, take your insurance, and available when you need them, and treat almost every condition under the sun.

You look up doctors. Here's nearby doctors. Here's reviews from real patients. Do they take my insurance? Yes. Let me just book a meeting with this doctor all through the same app. This is the right way to do healthcare. You should be using ZocDoc. This is true, Jesse. It says in my ad notes here, it says in my ad notes that younger people are using TikTok to try to figure out medical care decisions.

- Yeah. - That's a problem. That's a problem. You need ZocDoc. If you're using TikTok to figure out your medical conditions, you're gonna be giving yourself a prescription of a fire dance, and you just start dancing. And about halfway through the dance, your friend is like, "Yeah, but you still got "that six-inch rebar going through your spine." And you're like, "Yeah, you're right.

"I probably should use ZocDoc.com." So you need ZocDoc, the only free app that lets you find and book doctors. Now, we do have a little bit of a contest. I should mention this. We do have a little bit of a contest. We like ZocDoc.com because there's a lot of ox in it.

So we have a kind of informal contest of what could be an even cooler ox-centric URL. And you remember this, Jesse, 'cause I sent it to you. Someone sent us the idea of, what was it, like, what if the Dwayne Johnson, was this right? Dwayne, or was this mine?

Dwayne Johnson has a website where he helps you make model-size docs for like model train displays. And his website was rockmockdoc.com. That was a good one. Now it's got zocdoc.com, but rockmockdoc.com. I like that. So anyways, go to zocdoc.com/deep and download the ZocDoc app for free. Then find a book at top-rated doctor today, many available within 24 hours.

For God's sake, stop using TikTok to diagnose yourself. That's zocdoc.com/deep, zocdoc.com/deep. I also want to mention our friends at Ladder. So we're talking about things you should be doing, but you're not because you don't know how to get started. Life insurance is the other big one. If there is anyone who depends on you, a spouse, a partner, kids, you need life insurance.

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These are all policies that are insured by insurers rated A or A+ by AMBEST, they're high quality. So you just go to the website, ladderlife.com/deep, type, type, type, done. It's off your to-do list. This thing that you have no idea, you know you're supposed to do it, you have no idea how to do it, it's off your to-do list.

You should do this right now. So go to ladderlife.com/deep today to see within minutes if you're instantly approved. That's L-A-D-D-E-R life.com/deep. Ladderlife.com/deep. All right, Jessie, we like to talk about each month, the books I read the last month. Long-time listeners know, my goal is to read five books per month.

So we're in February now, so we will talk about the five books I read in January, 2023. The first one was called "Sitting by the Mini Bay, My Life in Building Model Docs" by Dwayne Johnson. So that was a surprising twist, surprising turn by him. It has over 50 pages of photos.

He's shirtless in most of them, interesting. He builds his mock docs shirtless. So there you go. Now, what did I read? All right, let's go through this quickly. Book number one, "A Thousand Brains" by Jeff Hawkins. So this is a new theory about how the cortex helps create human consciousness and intelligence.

Jeff Hopkins is a former tech executive who put all of his fortune into trying to figure out how the brain works and then build intelligent machines using this research. This is his latest book with his latest findings. If ever there's like Reese Terminator-style character who comes back from the future to prevent Skynet from going online, he's probably gonna be looking for Jeff Hawkins, let's be honest about that.

All right, I also read "The 90s" by Chuck Klosterman. So Klosterman writes these books where, I don't know if you've ever seen a Klosterman book, but he's been doing these more recently. Like the 90s is just looking at the 90s and it's just all these different smart cultural critiques about different aspects of the 90s, which is when you and I were kids.

It was good. Yeah. I've heard it was really good on tape. I read the physical version. I enjoyed it. I mean, it helps that I grew up then, but actually I might lend it to you. I think you would like it. Any examples? I mean, I think the music stuff is interesting.

Yeah. Like he gets really deep on really what was happening behind the scenes with grunge and these musicians and the whole selling out culture that Gen X had created and how that clashed against the commercial imperatives of music. I actually learned a lot about, like Kurt Cobain, for example.

Interesting. It doesn't make me think of, I don't look back after I read this book and say, "Man, I wish I could go back to the 90s." It's an interesting time. And it's interesting to think about, but it doesn't make me want to go back. But you know what I found out?

You remember the 70s show? So when we were growing up in the 90s, there's a show called the 70s show, which was a sitcom about life in the 70s. Yeah. Well, now we're 30 years, 20 or 30 years out of the 90s. They're doing a new show called the 90s show.

Yeah. Because when we were growing up in the 90s, the 70s was as far from us as the 90s are far from people who are kids today. So our childhood is now going to be the target of the nostalgic retrospective show. It was a good time to be a New York Yankee fan if you were.

Yeah, late 90s. Yeah. All right. Then I read a quite a good thriller actually. Robin Cook's very first thriller, "Coma" from the 1970s, straight up, one of the first medical thrillers. So him and Crichton were both working on this, but Cook was, I believe he got to the punch first.

And it's, you know, it's creepy as hell. Like in the end there's coma patients. They're being put into comas surreptitiously so they could harvest their organs, not the spoiler alert. Really well-written. The interesting thing about it, unlike some modern thrillers is it's, I don't know, the last third before you get to any actual, I am being chased.

Like any, I mean, the first two thirds of the book is really this new resident sort of starting to unravel the conspiracy and doing investigations. And the main stakes are, you know, her supervisors at the hospital are mad at her or that if she's not at round, she might get in trouble.

So it's such, and yet it still works. Nowadays, a modern thriller, it's, you know, the second page, the shark is being shot at you from the cannon and you have to kill it with a laser sword. You know, it gets right into it. So different time, but great book.

- When you read thrillers, do you breeze through them? - I'm not a fast reader. My wife is a fast reader. When she reads novels, she's like, I'm just, because I read a lot of nonfiction and write a lot of nonfiction, it's hard for me to speed up. So I'm the guy reading that's thinking, okay, well, interesting.

They referenced the computer mainframe in chapter two and they noted that it was using hexadecimal. And now we're in chapter four and I'm wondering, you know, I'm reading these thrillers like I'm studying Proust, which is probably not the fastest way to do it. - When you say you're not fast, are you really fast?

- I don't read these books very fast. I'm not a speed reader or not. I'm not even like a fast reader. I go too slow because my mind always wants to understand everything and fit everything into, I'm gonna, what Jeff Hawkins at a thousand brains would call reference frames.

My brain, that book helped me understand my own brain. I have like an overactive reference frame system. Everything I encounter has to be fit into these frames and I'm incredibly unhappy until it is. So I can't read things fast. I can't have loose ends. I need to, okay, here's this person, here's the building, here's the rooms in the building.

Like it's very useful when it comes time to solve math proofs or write things, but I can't, I'm just physically uncomfortable. If it doesn't bother my wife at all. If she's like, oh, I don't remember if like, oh, who is this guy? Was he dead? Or, you know, I'm like, no, no, I need to know like exactly his, like who did he connect to?

How is this house laid out? So I can't read fast. I mean, you're right, maybe it's fast compared to, depends on the relative. - One more quick question about this. When you read a 10 page New York article, how long does it usually take you? - A while. If I read like a standard, because you know, I always try to read at least one article from the magazine each week when it comes out.

- Half an hour? - Yeah. Like I'll read it in the morning sometimes for the kids get up and it will take the whole time. And sometimes I'll have to come back to it. Yeah, because I'm like every, because, but I'll come away and be able to tell you everything that happened in that New Yorker article, some of the stylistic choices of the author, you know, and I pulled out like two second order theories that we could potentially talk about on the show.

So it's like a very cognitively involved process for me when I'm reading. I'm a machine for turning text into connected, internally consistent theories and ideas. Like that's what I am. I've been like bred in a lab to do that. All right, next, this is not really a book. Neither of these are really books, but I just read them back to back because one influenced the other.

I read this over Martin Luther King weekend was Thoreau's on civil disobedience. And then Martin Luther King's letter from a Birmingham jail, the latter of course, inspired by him pulling from the former. So I thought it'd be interesting to read those, read those back to back. MLK's I think is much better than Thoreau's.

I mean, I get Thoreau's at the time, I mean, obviously it was an innovative thought. Gandhi pulled from an MLK pulled from it, but it doesn't age as well. And in part because he created a world that's been more normalized. So it doesn't seem as retroactive, but it's, you know, I'm not gonna pay my tax until my friend comes like three hours later and pays for me to get out of my small jail in the town where I'm related to everybody.

It just feels very different. I'm an MLK as a rhetorician is so good. Just his ability to make an argument and to inject a sort of a humanity into it. Yet it's still just rock solid. This clicks to this, this sort of inevitable logic with emotion. I mean, just absolute once in a century type ability.

So you read these back to back and Thoreau, I mean, I love Thoreau. Thoreau's very influential to me, but you see the person who's really throwing the 105 mile per hour fastballs MLK there. Yeah, not Thoreau. And then the last was, well, I don't know how many people are gonna follow me up on this recommendation.

The Feynman lectures on computation. There's a book form collection of a series of lectures that Richard Feynman gave at Caltech about computation. And I've pulled from it before for various classes I taught, but I read that right at the beginning of January because I didn't teach last semester. I was on leave.

And then before that was summer. So I hadn't been in the classroom since May, 2020. And I wanted to get back in the mood. So I was like, all right, I'm gonna read Feynman's lectures on computation. Just to get back in the computer science, he pedagogical, Feynman's a physicist, not a computer scientist.

And he just, so he comes at these things like with really originality and new takes. I just thought it would put me back in the mood of, you know, hey, let's explain things to people in useful ways. It was pretty good. I would say like 50% of the stuff I really loved reading about, 20% I'd know it so well.

I teach it and the fields advanced since Feynman wrote it. I'm like, this is like a worst version of it. And then the other, whatever percent is left was really just physics stuff I didn't care about. The stupid reversible circuit stuff. It's like, I don't need to hear any more about reversible circuits, but like his information theory and coding theory chapter is fantastic.

So there you go. I don't know how many people will take me up on that last recommendation, but the Feynman lectures on computation doesn't move as fast as coma by Robin Cook. It's not the similar genre, but I enjoyed it. All right, I got to run. Thank you everyone for listening.

If you want to submit your own questions or case studies, there is a link in the show notes. If you want to watch what you just heard today, it's episode 236. Go to youtube.com/calendarportmedia. I'll be back next week. And until then, as always stay deep. (upbeat music) (upbeat music) (upbeat music) (upbeat music) (upbeat music)