When Productivity Theory Meets Practice

Applying productivity ideas in reality

0:00So on this show and in my books, I talk a lot about time management and attention management strategies. I do this because I think in an age where we have increasingly powerful digital distractions and diversions pulling at our brains, we need to bring our A game if we're going to maintain some sort of cognitive autonomy. But here's a thought that's been bothering me recently. I don't spend enough time actually following up on what happens when my abstract ideas get implemented in the real world. So this became a little bit of an obsession.

0:35I said, look, I need an episode where I follow up on the real complications that real people experience when they put my type of ideas in the practice. I was trying to figure out how to do this and I had this idea that maybe I'm going to recruit like a whole bunch of people and I'll give them all advice and I'll follow up with them on a regular basis and I'll take notes on when they're having problems and what works. And this just seemed like a huge amount of effort. So I kept procrastinating on this. Like I felt really stuck. I wanted to do this episode, but I didn't know how to do it. But then I had an epiphany. Oh yeah,

1:06I know of a company that's already doing this. It's a company that's called Done Daily and they offer productivity coaching where you actually work with a coach who helps you develop systems and rules and then you check in with that coach every day and they help you adapt and adjust and make your systems work for you. Now, here's what's key. They use a lot of my ideas. Now, this is no coincidence. That's on purpose. Actually, I know the founder of Done Daily. I used to interview him back in the early days of my Study Hacks blog. I've known him forever. And

1:38when he put together this company a few years ago, I worked with him. I talked with him about my ideas and sort of helped them develop the productivity philosophy that their coaches would teach their clients. And then I became an affiliate of the company. So I still get updates on a regular basis of, hey, how are things going with this company? And so I know a lot about it. I was like, oh, they're already doing this. They're already working with hundreds of people to help them implement my type of ideas and getting a lot of feedback about it. So I don't need to go out there

2:09and on my own follow up with people. They're already doing it. So this was what I'm going to do today. I've invited onto the show one of the Done Daily coaches. Her name is Haley Pulley. And I asked her to bring case studies based on real clients of real complications they had when trying to put my type of ideas into practice in their lives, and then to discuss how they overcame those complications. It's exactly what I was looking for. So if you think about my books or my time and attention

2:41management episodes on this podcast, like a undergraduate degree in productivity, today's episode is you're getting your doctorate. We're going to get nuanced and in the weeds, and we're going to get realistic about how you actually manage your time and attention in our current moment. I had a lot of fun with this episode, a lot of great insights. I think you're really going to learn a lot as well. So let's get right into it.

Meeting coach Haley Pulley

3:04All right, Haley, thank you for joining me on the show. Absolutely. I'm glad to be here, Cal. I've been excited about this one because it's a question I get a lot, or maybe I should say it's feedback I get a lot where people say, on paper, this idea you talked about for organizing my life or pushing back on the forces of digital distraction. Sure, that makes sense. But in my real situation, I have to deal with X, Y, and Z, how do I adapt for that? There's a reality check to

3:39theoretical advice that I think is often important when we're talking about how to organize your life or be more productive. And you over at Done Daily are surrounded by reality checks because you are working with real people every day who are actually trying to put the types of ideas people like me talk about into action in real diverse circumstances. So as I mentioned in our intro, we have a collection of different case studies. I want to go through these one by one. We'll start by hearing the problem, and then we will hear what solution you as a coach at Done Daily came up with for this person.

4:14And then I will give my take, my riff, my surprise, my shame. We'll see how this actually goes. I'm excited

Mark and time blocking stress

4:20for this. Can we start with the example of Mark? We absolutely can. So Mark gets a lot of stuff done, I just have to say. Like this guy, he's productive. And one thing that he was really regularly implementing, and I would imagine you hear a lot about, is time blocking. But we started to discover that time blocking was creating a lot of stress for Mark, which might not be surprising

4:52to people tuning in. But what was happening was Mark was time blocking every single moment in his day, which I think you recommend. Is that correct? Was he going, like to what level of granularity was he going? Nine to five. And then even beyond because he has little kids and there were, you know, personal responsibilities afterwards. So every moment of his day generally was time blocked. Okay. And these were full blocks. He was in the situation, I'm assuming, where you create the plan

5:24where you say to yourself, if I actually got through this plan, wow, that would be great. Look at all the things I would get done. And you kind of fall in love with the super tight blocked plan. You're like, wow, that would be awesome if I could get every one of these type of things done. And I'm assuming it all worked well. And he's it was happy. Is that what happened? Yeah, no, no. As you said, this was a real life human being with real life friction, which I think is probably what you're talking about when people write you and say, theoretically, this works. But then real life stepped in. And one of the

5:58goals for Mark when he came to done daily was to actually end his days feeling less stressed. And the time blocking became a point of real conflict for him because he would schedule everything very granularly. And inevitably, you know, meetings would run late, something would take longer than he anticipated, he would get stuck in traffic. I mean, he was factoring in, you know, commute times. And, and I, I saw this because I got to work with Mark every single day. And I said, Look, we've got to change up how

6:32you're time blocking. And so we work together to experiment with actually reducing how much time blocking he was doing every day. So his, his stress was coming in part from just the feeling of falling off of this schedule, like every time that schedule got violated, what what he was feeling like this was a failure, or that he was out of control, or that he was unproductive, what was going on with him? What was the thing that was really driving him to be upset? Yeah, it was, it was just that it was like, I've thought of everything in my day, I've put it all on this calendar, it didn't turn out that way.

7:07And I'm frustrated about it. And also, it would cut into things that he really needed to work on a lot of time. And those things were starting to pile up. So it was stress of not achieving that perfect day and the stress of things actually not happening, not getting done. Because if he doesn't achieve the perfect day, there's blocks that aren't happening. And the work that was in that block, now that's starting to pile up and he's starting to feel like he's falling behind. Correct. Okay, so what was the solution that worked for Mark? So the solution? Well, it was kind of a couple of steps. The first

7:42step was to get Mark open to the idea of time blocking less. So actually starting to leave space on his calendar that wasn't claimed. And that took us a couple of weeks to practice and kind of get comfortable with. So and then once we did that, it was like, Okay, let's not rush to fill that up. Because maybe we're starting to see we can build in more buffer time, which is what ultimately ended up helping him was certain things on his calendars lunches out for work, certain meetings, he did some walkthrough

8:17type things, even commuting, we built buffer time around that, which would give him kind of some breathing space. And we started to see that he was able to get more things that he really needed to get done, done. So that's how we approach that. All right. So are these these, there's two things you mentioned that sound related, but maybe they're a little separate. So just to clarify, there's the there's like the scheduling less. So so not, not trying to fill in, you know, having blank time in the calendar, and then there's adding buffers around things you're blocking. So maybe typically, in theory,

8:50your commute could happen in 30 minutes, but let's put an hour 45 minutes there so that you have buffer time. Were these two separate things? So is there a difference between it's okay to have, you know, some blank time in the afternoon, and we're going to add buffers, make each block bigger than you think it needs to be? Or was it just we schedule less and then just expand the length of each of those blocks to fill in the gaps, you just have more than enough time for each block? What's the right way to conceptualize that? No right way. I think it really is personal. For him, just having the open space was a little, it didn't quite work for him. So we needed to be a

9:26little more intentional with putting in specific buffer time that was allowed to be for a meeting that was running late or commute time that took longer than he expected, versus just this white calendar space, because we actually ended up doing something different with a white calendar space as well. So it really was tailoring this time blocking approach to Mark very specifically based on his personality, his character, and the things that he needed to make for a successful day. I want to take a quick break from my conversation with Haley to talk about some of the sponsors

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12:36This is interesting because it reminds me of a point I make shortly and it's hidden where most people aren't going to see it because it is in the introductory text of the actual time block planner I sell. But I think it's actually a very important point where I said, hey, based on what I had seen, which is exactly what you're describing with Mark, especially if you're new to time blocking, it's almost as if you have to make your initial plan, then take every block that's on there and add 50% more time. 50% more than you think it's actually going to take. Now, of course,

13:07this is going to knock things off of your plan, but what you end up with is actually much more likely to be reasonable. It's this, you probably see this all the time. I call it sometimes the fairy tale effect. We write ourselves a fairy tale about how we want the day to go and then we fall in love with that story because it's great. It really would be great if you got 20 different things done and everything perfectly stacked and then your mind is simulating being done with all of those things and it's giving you a reward right there as you're doing the

13:38simulation. You're like, well, that feels good. That's what I want to do. But in reality, your schedule has just become intractable. So I like this idea. People are afraid, oh, if I do that, I'm not going to get enough done. But there's also this reality check of the time is the time, right? You're not advising the Mark, like I want you just to spend two hours staring at the wall every day. I mean, you're basically saying this is how much you can actually get done. Just because you can imagine getting more done on a time block you came up with doesn't

14:09mean that somehow that's the right level of work. This is what can actually fit. So, okay. So that sounds good. So, okay. So by being more generous in his blocks, this sounds like it helped that he felt like he was not falling off the schedule as often. And I'm assuming he didn't immediately get fired. His boss didn't immediately come in and say, hey, it looks like you're getting 20% less done. I was measuring it. You're out of here or something. So it sounds like there's a pseudo happy ending here. Uh, absolutely. There was, and he was less stressed, less stressed and actually getting

14:45more done. All right. I love that. Um, all right. So let's move on. That was good. Let's

Chris and the streak mentality

14:50move on to, uh, Chris. So what was Chris up to? So Chris is what I would kind of in a cheeky way call a streaker. And it's not the kind you think cow clothes on clothes on. We were about to have a lot of our audio listeners jump over to the YouTube version and you just disappointed them. I'm so sorry. He loved a big old check Mark on the day, right? Like, and that every day kind of looked the same and was real, just, um, what's the word I'm looking for? Standardized.

15:23Okay. And he liked the, like the Jerry Seinfeld advice of like, don't break the chain style person where every day you check off on your calendar, you did the key thing and you, you don't want any days where you're missing it. That type of, I, I'm prone to that type of streaking as well, that there is something satisfying. Okay. So what happened with Chris? So we went into multi-scale planning, you know, for a big work project and in his mind, it needed to have space on his calendar every day. But like most people, every day doesn't look the same for Chris. And so we had to think of different ways for him to find consistency,

16:00which I would argue is different than a streak. Um, so that this idea of multi-scale planning did not consume him because it became a real point of, I can't do it every day. And then the whole thing would fall apart. All right. So let me, so let me, for the audience who doesn't know, multi-scale planning is the idea where you're looking at your, your activities on multiple time scales. So, you know, obviously every day you're making a plan, but in the type of multi-scale planning, I talk about, you're also every week making a plan for the week

16:30ahead. And then on a bigger time scale, like every quarter, every season, you're making a plan, uh, for that time scale as well. I'm assuming, so what you're talking about here is Chris had a major project he wanted to make progress on. Um, I mean, was it at the, the weekly scale where he was looking at his week ahead that he was saying, I want to make sure there's effort being put towards this project on every single day. Is that, that, that was the, okay. That's the one. Okay. But he's not the difference. Here's what people don't know about Jerry Seinfeld. They forget about Jerry Seinfeld at the time when he did

17:01this every day, I'm going to put a check mark on my calendar. That was when he was just a professional comedian before the TV show. He only had one thing to do. It was to work on writing jokes. Okay. So Chris, I'm assuming had more than one thing pulling on his time, which is probably, uh, you can continue the story here, but that's probably where he began to have trouble. It absolutely is. I mean, not only does he have a career, he had a career that required him to travel. Um, and that was a huge point of friction. He's also a family guy. So he had kids, he had a wife, you know, he had obligations outside of work. And like

17:37I said, every day was not the same. He had many hats he had to wear. Interesting. Now, was this a work project or a personal project he was trying to, um, interface in? No, it was work. It was a work project. And how much time, you know, for it to, in his mind, for it to count as I worked on this today, I want to keep the streak alive. He probably, what was his minimum, like an hour or something like that? Oh, he was starting with two hours a day. Oof. Okay. Yeah. All right. So that wasn't working. So despite his best effort, he would just

18:08have the day where you have to go to the kids event at the school and then it's back-to-back meetings and a dentist appointment and then baseball practice. And you're like, I didn't get it in. Um, what, what, what was the psychological impact on him at first? You know, what, what was happening? Was he frustrated? Was he worried? Was he down on himself? What was going on? Um, it was a real frustration. I think is probably, you know, the one, and he would get so frustrated with it, but it was almost like he just knew that's how it was going to turn out. So he would

18:40just kind of wash his hands of it. And we would get a whole bunch of days where he would do end up doing nothing. Interesting. And of course, exceedingly frustrated by it. Oh, so if he, I, this is an interesting observation. So if he lost one day, he would just stop working on it for a while. Like, well, this is just not working. Oh, interesting. Okay. So what worked here? What was the solution? So we talked about the difference between just streak mentality, which again, I think a lot of people fall into the trap of it has to look the same every day for it to count. Well, if you're Jerry Seinfeld working on writing jokes, write a joke a day. Great. It

19:14looks the same every day. I give myself a check mark. I move on. Um, Chris was, I need two hours of work a day on this project. Check mark. I move on. And when that wasn't happening, we were falling off. So we, we broke down streak mentality and I really encouraged him to start looking at it as consistency. I think a great analogy is imagine over the course of a three month multi-scale plan, it's about spending $2,000. Okay. Um, you don't have to break that down by 90 days and spend the

19:45same amount every single day. That analogy really helped him understand. It's not about exact same every single day. There are going to be days where you spend more of the money. There's going to be days when you spend less of the money. And for him, it really helped this idea of consistency. Something I taught him was touch it daily. And we talked about what touching it daily could look like. It might not look like creative work, but for him to sustain sort of his focus on it, say on a week where he had to travel. Okay. Pull out your notes, refresh yourself. What is it you're thinking

20:17through? You know, when you have the odd moment to think about it, where are you going to pick up next time? And this became a way for him to sustain his streak or put better consistency over the course of weeks where he couldn't spend as much time on it. Interesting. So it was a combination of, we're not going to completely deny your streak mentality. So why don't you make sure every day you like touch it or look at it, or even if it's just for five minutes, and then you increase the timescale in which you're looking for consistency. You need to be making a lot of progress over a

20:48bigger timescale as opposed to a little progress every day. Was there a measure? Like every week you should get at least as many hours or every month. Was there like a particular timescale or measure, or was it more when we look back? Because I know it's one of the things that done daily does, you look back over the week. Is it, we want to look back and say, you got a good amount done this week. Like, how did he think about what counted as you're making consistent progress once it was no longer every single day you're doing two hours? Well, when we look back on the two-hour

21:19failures, let's put it that way, we'd end up with zero a lot. So looking back was helpful for him to identify times he was able into factor, you know, touching the project, spending 15 minutes reviewing notes, or sometimes he even managed 30, which was surprising to him. And then by the end of the week, it was like, great, we have something here. We have a certain amount we can actually track that you did spend on the project versus the zero you would end up with when you, you know, planned for these fairytale

21:49days of work. Interesting. So this reminds me of a couple ideas. I mean, first of all, I think this is important, this idea. I mean, this is classic multi-scale planning. Making progress on things at multiple timescales is key. It's why you can't just live in the day. If it's everything has to happen every day, that quickly falls apart. There's two different ways I've also seen, you know, dealing with this. One I've tried and one that actually Jim Collins talked about, the sort of famed business author. When I was in grad school, I did a lot of deep work tallies and I didn't even have a goal,

22:22right? So it wasn't, I have to get this many hours of deep work on this timescale. I just had a piece of cardstock next to my desk with the tick marks per week of hours of deep work. And it was just a feedback loop. If that was really small, that's actually really good feedback. I was like, I need to find more time for deep work. And that was about the level I got to. The opposite extreme is this Jim Collins approach, which I came across again for the new book I'm working on. He kept a spreadsheet of essentially like deep work or creative. He had some word for it, but like his

22:53sort of most key work, his hard thinking work. And he kept a spreadsheet of how many hours he did every day. But the key thing he had in the spreadsheet is it would add up the last 365 days. And he would say that has to be past some huge number. It's a year's worth of deep work, but it's the past 365 days. So if he saw that number starting to get smaller, he'd be like, oh, getting closer to whatever his goal was. He would like work in some days with like a lot of the creative work to get

23:24that number back up again. And then you had a buffer. If you had a, you know, you're on vacation and that number went back down again. And so there's different timescales here. That's one extreme. I'm looking at the last year. It was some crazy number, like a thousand hours has to be how much I've done over the last 365 days. Or on the other extreme, I was just every day putting down some tick marks. Some days I put none, some more, and just making sure that seemed okay. So there's a lot of strategies here, but I like that idea of you can't solve your, you can't capture your whole

23:56goals for your life every single day. Like you have to work on other types of timescales. Um, okay. So excellent. So that worked well. I like the $2,000 analogy too. It's, it's a, you don't have to spend exactly this much every day, but over 30 days or 90 days, you want to spend $2,000. All right. Um, all right. Moving on, we have Sarah. What went on with Sarah here?

Sarah and overwhelming friction

24:20So this one is, um, not my favorite to share, but you know, the truth is it doesn't always work out great for all of our clients. Uh, Sarah, yeah, I know, I know, but you know, it's important to talk about Cal because the thing is, is, uh, you know, we worked a long time together. Um, we worked really hard. We broke things down. We tried to make friction disappear when we could. Um, and the truth is sometimes the overwhelm is so much that it kind of doesn't matter how many tools, how many tactics you

24:52try, um, at the end of the day, if you're not willing to do what boils down to the work, um, it's going to be hard to make any progress. So that's kind of what we're talking about with Sarah. Um, and, and what I witnessed with her a lot was that deep work with Sarah, the things that were really meaningful to her often just got completely washed out by the many other things she was juggling. We're talking email meetings, non-deep work required initiatives, that type of thing.

25:27Yes, absolutely. It was a lot of, you know, urgencies, fires, other people's priorities would just drown it all out. All right. So moving on, let's talk about Sarah.

25:40Yes, Sarah. Well, Cal, Sarah wasn't quite the happy story we'd all love to hear because the truth is sometimes, um, overwhelm is just too big for us to move forward. And that's really what it came down to with her. We worked a lot on trying to break steps down. We did some multi-scale planning. We attempted time blocking. We broke those time blocks down into smaller time blocks. Um,

26:10and, and what was really suffering was Sarah had a lot of deep work projects that were stacking up on her list. We kept a lot of lists and, you know, at the end of the day, all the tools and tactics just weren't cutting it. So she was, it sounds like she was busy. She was doing lots of things, but not that list of deep work projects just wasn't getting smaller. Correct. Yeah. The urgencies, the little fires, the shallow work, those were kind of the thing that we couldn't get around her

26:45doing most of the time. It was really a struggle. Now was she, was she on board with this as a problem or was there a part of her that was thinking, look, I'm getting positive feedback in the moment by handling these fires, by being accessible or what have you. Like what was, how did she feel about the state of her work, uh, during the period when you were working with her? Not good. It was a problem and it was, um, you know, self-reported problem. I'm getting all of

27:16these little things done. I cannot seem to get myself to do the bigger, harder stuff. So what would happen? Like she would have a plan, you would work with her. I mean, there's a time block plan. Here's your deep work time is protected. What would end up happening on those days? Uh, a lot of times nothing we wouldn't get anywhere. Uh, and to be clear, we worked through it a lot. We really, we spent a long time working together. We tried a lot of different things. One thing that we did sometimes find success with, and I think this is a really

27:47great approach for anybody who is struggling with getting to the work that's hard to do. If it lives on your list for a certain amount of time, we did this with Sarah. Um, say if I saw it on the, on a list for longer than a week or depending on the size of the project and the consequence of not completing it, it would fall off the list. So we really tried a lot of different levers to compel her into that harder work. Now, how much do you think her work environment was

28:17making the deep work impossible and how much was it, uh, just something about, uh, you know, the way she was, the way she was processing the, the, the, the responsibility she felt towards the urgent. Like, how do we, how would you sort of balance out the, there's too much shallow on your plate because people are putting it there versus the mindset of you're just having a hard time understanding that this stuff will be important. Even if, you know, other people might be disappointed, other people might be upset. You don't get back to them, but you have to do this. Like, how do we separate the organization from the person here? So there's, there's two ways to do

28:52that. Um, I think one as a coach, as her coach, I really tried to help her manage the amount of incoming communication. She was fortunate. She got to work from home. Um, and so we looked at how we could leverage tech to help with that. And also we had to watch how much tech was involved because that in and of itself could create some very easy distractions from getting to the deeper work that needed doing. Um, but then on the other side, I mean, like most people who are struggling with

29:23these issues, she cared a lot about the work she was producing and what others thought or would think of it. And I would venture to say sometimes she cared so much that would get in the way of even starting it, working on it, definitely completing it. And this sounds like the, maybe an example partially of what I sometimes think about as the jerk paradox, which was, this was an issue that actually came out of a talk I went to give at a, uh, big law firm here in DC. And it was actually,

29:55there was a, um, a club and it was a woman's book club, um, within the, there's a lot of affinity clubs within the big law firm. They had me come to talk and they were explaining this issue, which is they say the, the, the personality trait that actually was leading to advancement was essentially being a little bit misanthropic. If you're a bit of, you're not very social, you're a bit of a jerk. You didn't care so much about like, I don't care that you need this. I'm going to work on this thing I want to do. This is what's important. And that the effect of that is that people who are a little off or a little bit, you wouldn't want to like to hang out with them

30:29or we're advancing much quicker up the partner track because they would do more deep work, which would ultimately move the numbers and bring in more money because, um, they didn't care that they weren't answering your email. They would prioritize them themselves. And they were saying this is a problem because people who are actually more conscientious and like reasonable human beings are now falling behind. But the, but those are probably actually the people you'd want in the partnership because it's also, you know, a, a, a people business. So I wonder if something like that was kind of going on here is that it can be very difficult. I mean, this is the result of the

30:59digital is that you have an inbox full of messages. We can also think of that as like a line of people who need you. And then every moment you're making the decision of, do I turn my back on that line or do I want to be empathetic and help people who need me? And that's a very strong impulse. Uh, it's a, we set this up in modern work to have our natural empathetic human social impulses weighed against this much more artificial thing of doing sustained cognitive symbolic reasoning in a sort of isolation, which is a very non-natural sort of thing. That's an impossible or a very

31:32difficult trade-off to try to force our brains to make. And so, uh, it sounds like some of that was going on here is that like, Hey, these, this is important stuff. People need me. I don't want to ignore people. I don't want to be slow to respond. I don't want to be there and jump on the collar of the meeting when someone asked me to do it. And she was being almost too, too reasonable of a human being. Uh, am I pushing that too far? Is there something like that going on here? No, there's definitely that going on. And you're right. Like it's a really fine balance. And if you've lived, you know, frankly, your whole life on the empathetic side of things, it's a really hard,

32:06you know, 90 degree turn to become that jerk, right? Like you just, that's something we practice, you know, with the coaching sometimes is like, let's practice being a little different than we are. It doesn't always work out. It doesn't always fit. And sometimes the hill is just too big to climb. So in this case, uh, Sarah, you ended up parting ways, essentially. She, it became kind of intractable and she saw this, I I'm not going to be able to fix this. And then, uh, she went her separate way.

32:38Yeah. Well, it wasn't, I'm not going to be able to fix this. Um, unfortunately there was something else that got put on her plate that was really overwhelming and it just, you know, also trying to factor in the coaching and the, and, and frankly, the work of working with a coach, the work of trying to do things differently, just lost out. There just wasn't any capacity for it at the time. And this is a paradox of this type of advice is that it's, it's, uh, when you're in the situation where you most need it is often the situation where you have no time to give towards it. This is

33:11part of my explanation for, of all my books, actually, the, the, the book that performed the worst was a world without email, which actually has very big ideas and practical advice for taming complete overload. But that book came out during the pandemic. And part of the problem I believed is that everyone was so overwhelmed by the problem that I was talking about in the book, because all that got amplified once we went remote and we had to move more, uh, high density synchronous interaction to be all asynchronous, all email or Slack. It just exploded the amount of

33:45context, digital context, such as we had to do. People were too busy to even think about the solutions to the things that was causing the busyness. So it's, it's really the, it's the irony of, of, I mean, I guess we see this in physical fitness too, I suppose, right? Is that it's when you're in the worst health, that it's the hardest to do the exercising that ultimately will help you, you know, um, be in better health. But I do have a couple, so I have a couple ideas that come to mind. The, the, the two ideas that come to mind when I think about these type of cases, which

34:16they just happen. I remember early in my career, when I was blogging about student advice, I had a web series where I was advising undergraduates in the Boston area to use my student advice. Uh, and one of the students who I called Lena in the series, we had that exact same issue. I, I, I was, I was looking at her schedule. I was like, this is intractable. We have to make these major changes. And she, she couldn't do it or wasn't willing to do it. She had all the pressure of her hometown on her. She was at MIT. She's like, I can't, I, I can't do less. Like everyone's counting on me.

34:51And it, and it just didn't work. And she ended up having to go home for a semester on mental health leave. It just completely, uh, completely burnt her out. But the two things that came to mind is one, paradoxically, uh, if you keep adding big deep work projects to your plate, eventually you get a log jam where you can't make progress on any deep work project. And I wonder if something like that was going on here. I write about this in my last book, Slow Productivity, that the problem is, is that each major project that has a deep work core brings with it its own administrative overhead, the sort of the meetings, the emails, the back and forth interactions needed for that project to move

35:23forward. That's a fixed cost. Each project is this much of this goes into your schedule and it has to be done because you've agreed to this project and that's how it's going to move forward. If you add too many of these projects to your plate, the fixed overhead costs add up to a point where there's no more time left to do the projects. And it's this tipping point you can go past where it's terrible because it's, I've never had more important things to get done. And it's never been harder for me to make even a little bit progress on any of them. And, and I bet something like this was

35:56going on here as well, because we don't track workload in the knowledge work context in any sort of systematic way. We just assume it's better to have more on your plate than less because then you'll have no downtime. You can just choose what you work on. And we don't factor the fact that once you say yes to a big project, you're saying yes to a thousand emails. You're saying yes to 25 meetings. You're saying yes to 16 conversations per week in the hallway. You are actually allocating a lot of time outside of the deep work itself. And that time, that time is limited. So that comes to mind

36:26as well. This might've been a, a workload log jam as well. And some of that's company culture. Like, Hey, don't say no. We'll notice if you say no. Um, no one knows how much stuff you're working on, but you better say yes to the thing I'm saying here. Yes, absolutely. The log jam, 100%.

36:43I'm a, you see, you got me preaching here now. It's okay. I appreciate it because you're backing us up, right? Like it, I think everybody ends up in that spot at some point and it can be really hard to, to know how to unravel it. It feels like a house of cards, right? Like what happens if you start saying no? Yeah. And usually that is the answer. I mean, with that student Lena, I said, look, you, you have too many activities and your, your course loads too hard. And I did the math. We sat down and filled out a sample calendar and I

37:16said, it doesn't fit. I can't fit onto your time in a week, all the activities and studying you have to do. So to me, it's self-evident that you got to reduce. You couldn't because the cultural expectation, you know, that's how she had gotten into MIT was I do lots of things. It's what I'm known for. That would be a failure if I, if I, you know, pulled back. And I think this happens in the work context too. I can't reduce what's on my plate. Say no would be a disaster. Say no would mark me as a, as not a team player. Like it's a difficult situation, even though you really

37:47probably have to cut your workload in half would probably double the amount of useful work you're doing for the company. But that's a very hard equation to make this doing less is going to make you produce more is very paradoxical for people. It absolutely is. And that's something I've been concerned about. Um, as a coach with done daily is, are we selling the very thing we're trying to keep people from doing, you know, it's, it's, I, I don't know that we actually want to make people more productive in the sort of general sense of do more, you know, it's just do more of

38:24what matters most and do less all around so you can live well. If you don't have, yeah, I don't like the, this is the problem with the word productivity. Sometimes it's more about, do you have control over your time and attention or not? And if you do, now you have a lot of options. Now you can, you can aim it to the right places. You can, you can customize your workload. You have a lot of levers you can now pull. If you don't have control over your time and attention, it's just haphazard and stuff is just going to pile and you're going to fall behind. Uh, it's not, I often have to argue

38:57this to people. The trade-off is not, if I use organizational productivity advice, uh, I'm going to be super busy and like doing a lot. And, and, and if I don't, I'm going to be, uh, on the park bench, you know, reading a novel at lunch and life is going to be that, that somehow it is the, the tools create the stress. And if you don't have the tools, you don't have to be in stress. The reality is it's, it's, you're being bombarded. And if you have no systems for controlling your time or attention, it doesn't stop the bombardment. It just means you have no protection. You get hit a

39:29lot more. And if you do, now you have a fighting chance of maybe, you know, getting a shield up or finding some cover and figuring out something that's sustainable. It doesn't mean that you necessarily will, I guess that's the point of Sarah, but at least you have a chance. It's about, do you want, you want some leverage over your time and attention, some control and intention, or do you want to just have your day unfold? But the busyness, I mean, this is, I get in this argument sometimes with, with my friend, Oliver Berkman, the busyness doesn't come from having the organizational tools. The busyness comes from the stuff that you say yes to,

40:00or is being pushed at you. And that's going to happen whether or not you have a planner or not. That's, it's sort of unrelated. It's what you do with the work that this advice starts to, starts to matter. I want to take another quick break to hear from some of the sponsors that makes this show possible. Do you know what's scarier than the elaborate animated Halloween displays I've been working on this month? It's customers getting ghosted by your own business. See what I did there, Jesse? Ghosted? I'm talking about customers who call, but receive no answer and no callback,

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42:53masterclass.com slash cal. Head to masterclass.com slash cal to see the latest offer. All right, let's get back to our conversation with Haley. All right, what about Jennifer? We'll get a positive case here.

Jennifer and attention residue

43:07What happened with Jennifer? Yes. Okay, so Jennifer, wow. Now, here's somebody who does fit a lot into her day. I have to admit. It's like one of those people you look at, and you're like, I don't know how she does it. And she does it really well. Very calm, very cool, very collected. But this is somebody who continues to improve how she does things and somehow gets cooler and calmer as she goes. Everybody wants to admire this person. But one thing that we worked on with her, because she

43:40found, you know, because she gets so much done in a day, she is doing so much. She's wearing so many hats, shifting roles. Attention residue was a real problem. She'd kind of time block her day full out. She'd, you know, run errands during the day or pick up her kid or have meetings. But when it came to those moments where she really had to like sit down and do some creative, deep thinking, deep work, she was really struggling to kind of turn off the rest of the day. And so we started out by just

44:14factoring in what we called transitions, specifically before her deep work blocks, because that seemed to be where it was impacting her the most. She would spend, you know, 30 minutes kind of calming herself down, maybe, you know, messing with her phone or looking through a magazine or something like that. And she just had to kind of wrangle the distraction for a certain amount of time. And then she'd look and she'd only have like 30 minutes to work on her deep work at that point. So we started to build in a very specific transition, or at least an intentional transition

44:47way of thinking. Sometimes it would be walking between locations before she'd sit down and do her deep work. But that was tagged as transition so that we could address attention residue before she dropped into her deep work block. I'm such a fan of that advice, right? We really underestimate that how difficult it is to actually change your cognitive context from one thing to another, especially if that other thing is deep work. So, okay, so would she get 30 minutes and she would mark something like that? Would you

45:18actually, she would actually think of it as transition time? Would she have a specific ritual or activity? Like what would happen? What worked best for her during these transition periods? I think for her, she kind of had this visual. Like let's say she was transitioning out of like a mom block, if you will, like taking her kids somewhere. And then she was going home to do some deep work for her job. I remember having a conversation with her where she told me like, I am thinking about taking off the mom hat and putting on, you know, my work hat. So for her, and she would do this on the

45:55walk, right? She didn't sit down anywhere and like specifically do this transition. She took advantage of a period of time that she had to spend commuting from one place to the next, but she intentionally visualized shifting gears so that by the time she got to the deep work, she was ready to go. I love that. Okay. So you have a walk or commute or something you can do to reset your mind. I remember during the pandemic saying something like this to remote workers where I would say, you need a

46:25commute. I know you don't literally have a commute, but go simulate a commute by walking a mile through your neighborhood to start your day, then take a lunch break and then go for a walk. So we actually kind of need these liminal spaces sometimes. But I think you nailed the neurological reason is because attention residue takes time. That takes time to clear out. The other place I like to think about, so I love that advice. Everyone should take that. I also think the other place this is really important is on the tail end of meetings that don't underestimate all of the open loops that

47:00are generated by sitting for an hour in a meeting, all of these tasks and decisions and notes and ideas. And if you jump straight from that meeting into the next thing, your mind is going to say to you, whoa, whoa, whoa, whoa, whoa, that we just made a lot of commitments. There's a lot we have to do. When are we going to deal with this? Right? Like that. And then you will have that stress and attention residue. It's almost hard to shake. So I also like adding 15 to 30 minutes on the end of meetings. If you want an hour meeting, I'm going to put an hour and a half or hour 15 on my calendar and have a period where all I'm doing is like taking notes and the emails, getting things

47:33on my task list. You can clearly shut down that meeting and get the attention residue off. I mean, this goes back to our first example is sometimes just having, you need more buffer that, you know, we're not Silicon Valley doesn't get this because they're used to dealing with computer chips. They don't need buffers. Give me a command, execute. Give me a completely different command, execute. I don't care. It's electrons through the same depth circuits every time, but humans are so messy. Like our brains, it takes time to switch from this into this. And we just

48:05don't think about that. You know, we don't, I don't think management thinks about this. The only psychology that management typically thinks about is motivational psychology. How do I make sure that my sales team is motivated to sell or whatever? But we never think about what you're finding time and again with your clients is the human brain is powerful. It's also slow to change. It can be messy and you need to build your workday around the reality of the main capital resource this knowledge work organization has are these brains. And we really need to understand how they

48:37work to get the most out of them. They can't just shift, shift, shift, shift, shift, shift, shift. They're not a computer processor. So that to me, that's sort of emerging as a theme and some of the advice you've been giving. Ah, very cool. I'm glad to see that. Yeah. And I, you know, it's funny because once, once we started practicing these shifts, these transitions, she started trying it in different places. It wasn't just before deep work, another really meaningful spot for her. And it's kind of has to do with like shutting down the meeting idea, um, was anytime she went to spend time with her

49:08family or her kid, uh, she found if she didn't kind of make that transition happen, she showed up there chewing on work and that's not really what we want. We want to be as present as possible where our feet are. I've had the same issue. If I'm working at my home office, like one of my kids gets home and they immediately want to get into dad, I got to tell you like 17 details about whatever. It's hard because your brain is still in one spot. And I've learned like, actually, if I'm going to be working sort of right up until like the kids getting home, it's better to actually

49:39go relocate to my office down the street so that I can have that transition of walking home and clearing my head. I'll be ready to be in dad mode. Whereas if I'm in the home office and I haven't had that 10 minutes to transition, it's difficult. Human brains are messy. I wish they were simpler, but they're messy. All right. All right. Let's talk about, uh, Lisa. What, what did Lisa figure

Lisa and moving shutdown routines

50:02out? So shutdown ritual, right? We're sort of talking about a little version of that without closing out like the meeting or the work block. Um, one thing we bumped into with Lisa was she was getting a little bit frustrated that that shutdown ritual wasn't happening right at the end of her work day. Uh, you know, and there's a couple of different ways to look at this. Well, there's a real reason to shut down at the end of the work day, but we had to work within the confines of her life. Right. And what often happened was she'd work right up to the point. She had to run out the door

50:36to go start taxing kids. Um, and so often we weren't seeing that shutdown ritual take place. And for a while it wasn't happening at all. I wasn't hearing from her, which is a, we often loop communication with a coach with a shutdown ritual. We're trying to, to get a couple of things in there. And I just wasn't hearing from her and I check in with her the next day. I know I didn't do my shutdown ritual. I'm going to try for it again today. Well, we just kept running into the same issue. She was just working right up to the point where she had to leave the office and deal with the

51:08second half of her day. And so one thing we did was move the shutdown ritual and we didn't try to cram it in between taxi rides for her kids. We didn't try to cram it in before dinner. I got with her and I said, look, realistically, where could you take at most 15 minutes to close loops, take a moment, recognize what you accomplished today, talk about what needs doing tomorrow and, you know, really think through and reflect what was frustrating. What do we need to look at?

51:39And we decided it was at the end of the whole day, right? So the shutdown ritual got moved. It's not ideal to kind of carry some closed or open loops from work through to the end, but that's just what we ended up with. And I have to tell you, she was far more successful and shutting down when we moved it. Interesting. So she was doing her work shutdown routine, not right after work, but still that same day. And so she was still getting most of those benefits of, you know, for the rest of the night, but also probably confidence of, I know there's open loops as I

52:12run out the door. I am going to shut these down later today. So it isn't, this won't be forgotten. Just being able to tell your brain probably helped. Even if we can't deal with this right now, we are at seven and probably even that helped from just the anxiety reduction standpoint. If you trust the shutdown is going to happen, you're still going to get a lot of the benefits that you wouldn't have if you weren't going to shut down at all. This happened to me last night, by the way, same situation. I had things right up until I had to run from my office at Georgetown to coach

52:44baseball, which takes a long time. So I wasn't really getting home till seven. And at that, and I had to eat, I was starving, eight. Then I took 10 or 15 minutes, did the shutdown. Then my wife went for a walk to sort of shut down the other sorts of things and get a sense of the day coming up. That was all happening between, you know, seven, 15 and eight, but it was still a shutdown routine. And I think it makes a huge difference. So that's interesting that it's okay. If you can't get the shutdown routine in right away, you can still get a shutdown routine in. Yes, absolutely.

53:17It's I, yeah, I think you got to talk to yourself. Don't listen to yourself. Cause she was definitely saying, well, I'm failing at this. And then she was dragging open loops through her nights, you know? So, yeah. I mean, I, I used to tell people just schedule something on your calendar for the end of the day to do it. But the problem is that sometimes works, but also that end of the day block is sometimes when the meetings happen, right? Like that, that's, that's the issue with like, it makes sense. It'd be like, I will protect that time, but you can't always for whatever reason. And there's good reasons for it. Sometimes like that is the time that

53:50people need to grab. Like, no, the four to five is like a good meeting time because that's often open still on people's calendars. And so it's, it's, it's unavoidable that you're going to get into those situations in a lot of jobs. All right, we're making progress now. We're getting, so we got two more here. I want to get to, let's talk quickly about Rachel. Yes. So common occurrence with people who are high achievers, they obsess over quality, which I know you're a big proponent of, um, for Rachel, it was becoming a real point of conflict

54:23because we weren't getting anything done because of the obsession over quality. So we had to work on the other end. We actually had to practice choosing good enough, which was not easy.

54:38So like what type of thing, what does that mean? Like practically speaking in her job, how is obsessing over quality turning into an obstruction? Well, you know, and I don't want to turn this into like AI bashing, but one thing, I know it's your favorite. It's your favorite. Um, one thing I would see is she would take something as simple as an email, professional email and run it through several AI before she would even consider sending it. And even then sometimes it would not be sent.

55:12So that's the kind of stuff we were up against. And it was a, to be clear, this wasn't like, obviously she cared, she cared greatly how she was coming across, but that, that pursuit of top quality, you know, deliverables, it just kept her in pursuit. She never could arrive sometimes at a point of this is good enough. It's time to put it out there. Um, and we saw that reflected in some of her bigger work projects. Um, and it would definitely push deadlines. It would kind of create some backup and conflict on her working teams. And so those are the kinds of things that

55:46we were having to, to work through. And, and really it, it was just, we have to practice choosing good enough. What does good enough like, what does done look like? That was a great question for her. Uh, so does that, so what helped that help, uh, in like in advance, figuring out a definition of done before you started working on a project or what was the most effective thing ultimately? That did, once we kind of got that question in place and we'd put it in our time block, right. When she was working on a certain project, remember, just ask yourself, what does done look like? And then the next question we ended up adding in and folding into our everyday kind of

56:21communication and practice was, um, could I say good enough and how it, it kind of became, again, we're really personalizing things. So she kind of had to develop this kind of scale of good enough for herself. Like, all right, if I'm in the five, six range, it's good enough. Let's go. Right. And just kind of let go and see what happens. And so we kind of had to expose her to good enough over a period of time where she got comfortable accepting that like, we didn't have to chase perfection in this case, this high quality, um, output that she deemed never good enough actually

56:55was almost always just fine. I mean, I think it's a, it's a, it's a point I underestimated, you know, you mentioned, I talk about obsessive over quality. It was one of the principles in slow productivity. It was the third principle. And I think it was my editor who came back and said, I think you're underestimating the role of perfectionism as an obstacle when you give this type of advice. And so I ended up having to add, um, a very large discussion about, uh, sidestepping perfectionism while you care about quality to that chapter because of more common than I, I realized I didn't have a perfectionism problem. There's another way I've been thinking

57:27about it recently. I'll just throw out there for the listener, which sounds similar to what, uh, Rachel's solution look like. But one of the ways I often think about it is, uh, when you obsess over quality, you, you want your skill level to be rising. So the, the, uh, your max quality you can deliver should be going up. But when it comes to any deliverable, be comfortable living within, you know, 80% of your max good enough. Right. And what you're really looking at is like, okay, so it's, it, you're, you're doing good enough. You're at 80% of like your, your max quality,

58:00but that max quality is going up over time because you care about doing things well and getting better. That means the quality of what you produce is going up over time. Right. And so whether at each step you're at a hundred percent versus 80 matters much less than are you moving up? Right. Because if you keep getting better at something, your 80% of quality is going to be way better than your a hundred percent quality when you weren't as good. Uh, but the difference to the individual is really massive because delivering good enough. I I'm 80% of my max on the quality here is way, way, way more

58:36sustainable than trying to be perfect. And so it's, that's, that's what I've come back to is it's all arbitrary, right? Like if, if you want to be delivering stuff, this good, just get your skill level to the place where that's like at 80% of what you can do. Right. So there's a difference between growing your max quality that you could produce versus insisting on always hitting your max quality in the moment. So I, in my mind, because I'm a nerd, I imagine these graphs and there, there's a gap between them,

59:06but both of the curves are, both of the curves are going up. Uh, but I have learned my lesson that this is actually a very important topic because, uh, a lot of people, this is an issue. It is. Well, I mean, perfectionism is a way to avoid ever being judged, right? Um, it is very hard for a lot of us to accept feedback, but to your point about improving over time, how can you become a better version of yourself if you live in a vacuum? Yeah. So with Rachel, it really became a practice of

59:41exposing herself to that so that she could improve, right? She needed feedback from her colleagues in order to know if what she was building was working, if there were ways to do it better. Right. And she gained skill and knowledge from exposing herself, but we had to kind of find the right dosage of that because for a perfectionist, it can be really hard to open yourself up to. All right. So I think we have time for one more here. Um, let's hear about David who's,

David and entrepreneur inbox overload

1:00:08who I think is an entrepreneur, right? So this is a good twist to have someone who, who effectively works for himself. Yes. And with David, it was a really, really common, it's a common thing we see amongst entrepreneurs. They end up doing all the work, right? Until you can grow your company to a size that allows you to hire on people, you end up doing all the creative work, all the administrative work. And I'll be honest, we see it all the time. The administrative stuff, the emailing, the customer service, um, all those little urgencies, they will consume you. And that's

1:00:43what he was drowning in. He had some, um, software development that he needed to do and he wasn't getting to it because he was spending his whole day in his inbox and it is common. We see it all the time. So there was, there was never a shortage of emails to be answered. So you could, if you chose constantly be in there answering emails. So that's what, so he was just basically, he was an inbox warrior, which is a problem if you're also the sole source of creating the value things that keeps your company alive because no one, as I always say, no one pays you for answering emails. And so I could

1:01:18see why this was a problem. Okay. So how did he, how did he get out of this? Well, so we, we had to try a couple of different things and I'm all about kind of experimental periods of time. So I work in, I generally work in like two week blocks with my clients to try new things. And one thing we tried doing was putting constraints on his shallow work times, his email times. And to be honest, he needed to answer these, a lot of these emails because it was customer service, right? And he didn't have anybody just yet to manage those things. It felt very productive and in a way it was,

1:01:49but he was frankly pretty good at it, pretty quick at it, but he would kind of spend his whole day kind of sitting around waiting for these emails to come across his inbox. There wasn't really big, large expanses of time for him to do the deep work that he needed to do. So we started by putting constraints on his shallow work. And we did see that that kind of sharpened his work in those times because if he only had limited time, then he had to kind of knock out more than if he was just sitting back casually working through his inbox all day long. So that was the first thing that we did and

1:02:21it did help. Okay. So he was still getting everything done because you're saying when you're focused on a single context with some constraints, you just are, you get more done in the, in the same amount of time. So it's not like he was, I have to sacrifice customer responsibility or I have to sacrifice, you know, these client leads and give up on business in order to have time for deep work. Actually just having clear demarcations, it still got done, but it freed up time for the other types of efforts. It absolutely did. It turned,

1:02:52and he was kind of surprised. He was like, okay, I actually have a lot more time in my day than I thought. That is, that is an inspiring note to end on because a lot of people feel like that's not possible. All right. Well, I think that is a great optimistic, practical note on which to end this discussion. I learned a lot hearing about how real people both struggled and then ultimately adapted the type of ideas we talked about here on the show to their real lives. So Haley, I want to thank you for coming in and sharing these examples. We'll have to have you back again later with a new

1:03:25collection of real world tales from real world productivity woes, because I found this really useful. So, so thank you. Thank you for joining us. Well, thank you so much for having me, Cal. I will look forward to the next time. And of course, if you're interested in what is going on over there at Dundaylee, Dundaylee.com. Do I have that right? You do. All right. There we go. Thank you, Haley. Thanks, Cal. See you soon. All right. So there we have it. That was my conversation with Haley Pulley from Dundaylee. Haley, thanks for coming on and sharing all of these insights. I felt like

1:04:00I learned a lot, even though the ideas were mine. Hearing about these complications that real people had added a whole new layer of nuance to understanding how this type of advice should actually be applied. Here's my meta observation, my sort of high level observation. You got to iterate. That seems to be the thread that weaves together all of the examples we just heard. You start with a good idea for how you're going to manage your time and attention, and then you test it. And then after you test it, you come back and say, what do I need to adjust?

1:04:33You test it some more, and then you adjust it some more. And when you do this, you'll discover what works for you is going to be very different than what works for another person, which will be very different than what works for me. Maybe the underlying principles are the same. Maybe even the core strategies are the same, but they have been customized to your particular situation. So I'm beginning to realize that perhaps the biggest danger when it comes in time and attention management is not necessarily people refusing to have any types of systems. It's instead insisting on being rigid in the systems you implement. And when those fail, you just give up altogether.

1:05:07So maybe that's going to be our meta mindset is that everyone's life is different. If a particular idea for time and attention management isn't quite working for you, adjust. It's okay. Make a tweak, make a move, add something, take something out. It's all about figuring out what works in your own life. So thanks again to Dunn Daily for giving us that information. I think I'm going to have to have them back. We should have them back again with a new collection of case studies. This is really useful to get real feedback. And we should find other

1:05:38topics actually. I'm going to tell Jesse this. We should find other topics I talk about where we can get more real world feedback. I thought that was really useful. But anyways, thanks Dunn Daily. Thanks for listening. That's it for today. Hope you enjoyed today's episode. And until next time, as always, stay deep. Hey, if you've made it this far, you must be ready to join my fight for depth in a distracted world. Now, the best way to do this is to join over 125,000 people who receive my email newsletter each Monday.

1:06:09You can sign up at calnewport.com slash ideas. And when you do, I will send you a free guide to my seven best ideas about cultivating a deep life. Sign up today, calnewport.com slash ideas. And when you're in a podcast, you can sign up today. And if you're in a podcast, you can sign up today. Bye.