Ever find yourself trapped in a game of “Calendar Tetris,” where each meeting block interrupts the natural flow of your day, leaving you little room for meaningful work?
Today on Rework, host Kimberly Rhodes sits down with Jason Fried and David Heinemeier Hansson to discuss the pitfalls of modern scheduling tools and their impact on productivity from their book, It Doesn’t Have to Be Crazy at Work.
Listen in as they walk listeners through scheduling at 37signals, where they don’t share calendars, and everyone is in control of their own time.
Plus, tune in for a sneak peek of the upcoming HEY Calendar, with innovative features designed to empower you to regain control of your time.
Watch the full video episode.
- Learn the biggest problem with calendar Tetris and how these small, disjointed chunks hinder individual productivity and focus.
- Conversation over convenience - why actively asking for someone’s time through conversation helps to foster intentionality (and reduces unnecessary meetings).
- Explore how 37signals redefines scheduling to empower individuals with full control over their time.
- Learn how the strategic introduction of scheduling friction prevents a culture of excessive meetings, fostering a shift toward asynchronous work.
- Discover a work culture where meetings are optional, highlighting the significance of prioritizing tasks with personal meaning.
- HEY is introducing a calendar! Just as the 37signals team revolutionized email, they’ve now transformed calendaring for 2024.
Rework is a production of 37signals. You can find show notes and transcripts on our website. Full video episodes are available on YouTube and X (formerly known as Twitter).
If you have a question for Jason or David about a better way to work and run your business, leave us a voicemail at 708-628-7850 or email, and we might answer it on a future episode.
Links and Resources:
From David’s HEY World: Just let me do my job
From Jason’s LinkedIn: What my calendar looks like
It Doesn’t Have to Be Crazy at Work
Books by 37signals
Sign up for a 30-day free trial at Basecamp.com
HEY World | HEY
The REWORK podcast
The Rework Podcast on YouTube
The 37signals Dev Blog
37signals on YouTube
The Rework Podcast on YouTube
@37signals on X
37signals on LinkedIn
Kimberly (00:00): Welcome to Rework, a podcast by 37signals about the better way to work in run your business. I’m your host, Kimberly Rhodes. If you follow 37signals on Twitter or X, or you follow the co-founders of 37signals, Jason Fried or David Heinermeier Hansson, you may have heard that 37signals is working on a new calendar product for their product HEY. Now we’re not going to reveal any of those features today, but the founders of 37signals, Jason and David have a lot of strong thoughts about calendars and time in general. So the chapter of It Doesn’t Have to be Crazy at Work around Calendar Tetris starts with, “The shared work calendar is one of the most destructive inventions of modern times. So much orbits around it. So much hinges on it and so much is wrong because of it.” Guys, these are very strongest statements. Tell me your thoughts about this.
Jason (00:48): Yeah, well, one thing we don’t have at 37signals are shared calendars, so I can’t take time off of your calendar. Kimberly, you can’t take time off of my calendar. We can’t see each other’s calendars. This is a good thing. It’s a really good thing. If I need an hour of your time, I have to ask you for it. Like literally, Hey Kimberly, are you free today at three o’clock? And you can go, yeah or no, and you can go, no, I’m not, but how about tomorrow morning at 10? I go, yeah, sure that works. So it’s a conversation and some people go, that’s so inefficient and go, yeah, it is inefficient. It should be inefficient. It should be hard to take someone else’s time. And modern calendars have made it way too easy to take other people’s time because it’s just a block. We’re talking about Tetris, it’s just a little square or a rectangle and you forget what that means.
(01:35): That chunks their day. The minute you take something away, their day splits in a half or whatever remaining time they have splits in half. You’ve got a before and after. And there’s buffer time around that and it just starts to cut the time and cut the days into small and smaller bits. And the way I’ve always thought about calendars, especially business, shared calendars besides not liking them, is that when you add something to most people think you’re adding an event. I actually think you’re taking something away. You’re taking away free time. You’re taking away space, you’re taking away time to work, so you’re putting something on, no, actually you’re taking something away. And you got to think about all the things you’re taking away from somebody when you ask them for their time. So we wanted to make sure, I mean this is one of the reasons we don’t have a shared calendar and what we’re building is not a team shared calendar either at the moment. This is an individual calendar system right now, but I think this is actually at the root of many of the problems inside most companies, which is that you don’t own your time. You don’t really have control over your time, and it’s way too easy to take other people’s time and to treat it as if it’s just a square. It’s just a little graphic and it’s so much more than that.
David (02:43): I think the main issue here is how easy it is to slice up a day. You’re taking some time, but you’re also taking it in spots that don’t make sense necessarily from the person whose time is being stolen. You’re just putting, oh, there’s an open block here at one o’clock. Great. Well, that person might have something at 11:30 as well, and then they might have something at three, and then that loose space in between the blocks are simply rendered irrelevant or unproductive because you can’t take these little chunks that are left once the Tetris blocks have fallen onto the week and do something with that. This is one of the things we talk about so often, this sense that your calendar may very well be full of colorful Tetris blocks. You are collaborating, you’re having meetings about things, and then you get to Friday afternoon and think, wow, what a busy week.
(03:37): And also, what the hell did I get done? And perhaps nothing of significance. I didn’t move things forward. I didn’t move the things forward that I wanted to move forward. And I think this is at the root of that discontent that the modern corporation often puts into people, the sense of making them feel busy, actually making them busy, but leaving them with so little leftover, so little accomplishments, so little progress, so little pride in personal work that’s physical or bits and bites like the deliberations in a meeting. Do you know what the number of meetings I can recall over my 20 year career? There’s like five that stand out where I go like, holy smokes, that was a consequential meeting that set the company in a different direction. It set the product in a different direction. It did something. That is such a small number of overall achievements I look back upon in my career.
(04:37): I look way more about product launches or feature launches or sharing open source or writing something up or any of these other things that we do that should be the bulk of it. And for a lot of people, it’s not. The bulk of their time is being sucked away in these forgettable moments of meetings. This is why we’ve also talked repeatedly about why meetings are toxic and these two things are paired together. The blocks that fall down on your calendar, they’re meetings. That’s what they are. They’re different kinds of meetings and some of those meetings are status updates or introductions to things. We should talk about all sorts of stuff that in the quote of a song, could have been an email, could have been a post on Basecamp, could have been something else than someone reserving or as Jason would say, carving out your free time to work and reserving it for this nonsense of spending time in this way.
(05:27): So I think the fact that we’ve made it so difficult to take other people’s time is not just a feature in the one-on-one example that Jason gives, but it gets exponentially more valuable the more people’s time you’re trying to reserve. If you have a shared work calendar, it’s very easy to take 5, 7, 8, 20 people’s time for some bullshit meeting where at least half of the participants have no interest whatsoever in being there. They’re being there out of obligation. They’re being there because the manager called the meeting. They’re being there because they don’t want to piss off someone else. They’re being there out of social obligation. They’re not there because they want to be there, right? But the calendar system made it easy at 37signals, it’s a pain in the ass to try to rally five people. It is exponentially harder every single time you add another person to a proposed call, trying to figure that out by hand is trying to do sort of, I don’t know, finding a square root with 10 digits on a abacus or something.
(06:25): Hard. Computers do that very well. Computers are very efficient at lining up Tetris blocks on a calendar and we need the friction. We need the friction. The friction is the feature when it comes to this kind of pushback on meetings first culture, returning us to an asynchronous way of working or not even returning us. For some people it’s foray into that, and this is why remote really doesn’t work in this way. A lot of people who were deeply unsatisfied during the time that they were forced to be remote were because of the calendar Tetris, all the blocks that fell on the calendar and then that was just zoom meetings, zoom, fatigue, all this other bullshit. It doesn’t have to be like that. And this is why when I share my personal calendar or talk about my personal calendar without entrepreneurs, they often don’t believe me.
(07:12): No. What do you mean you have two appointments on for a whole week? That’s the first two hours of my morning. So many people, especially managers, especially entrepreneurs, have conditioned themselves to think this is normal. It’s totally normal that my entire calendar is full of all these colors from people or my assistant or whoever taking my time. It doesn’t have to be, my calendar very often has very little on it at all, and I cannot tell you how much of a bliss that is and how related it is to this sense where people ask me like, I dunno, how do you get so much done? And either me personally or us as a company, how do you guys produce so much? How do you write so much? How do you release so much software? How do you do so many features with so many? It’s that. It is is the long weeks that are not jam packed with calendar Tetris meeting games. That is why we can do the things. It’s not because we’re working the 80 hours a week. I often feel like, you know what? I’m not busy at all very frequently when I look at Friday afternoon. Go like, woo, what a week? What a week? That’s just not the normal operation. They’ll occasionally be those weeks and it’ll occasionally be that day, but the natural feeling of working here is not like, holy shit, my days is blasted with all these obligations and this is why we get so much stuff done.
Kimberly (08:38): Okay, I will just jump in and say as an employee, I think this one thing contributes so much to the feeling of calm, the feeling of calmness because you have time to actually get your work done. And having worked in other organizations where people are just putting things on your calendar and you work an entire day maybe working through lunch at the end of the day it’s like five o’clock, 5 30, 6, and you’re like, okay, now I actually do the work that all of these meetings and interruptions created.
Jason (09:04): Yeah, I mean imagine just working, looking at your calendar in the morning and then doing some stuff and looking at again two hours later and it’s, your afternoon’s full. You didn’t make it full. Someone else made it full. That’s crazy. And that is the fundamental, it doesn’t have to be crazy at work? That is crazy at work if other people can take your time, fill up your day and they’re not removing things from your plate either, so they’re just adding stuff. You’ve got your own things you need to do and now you’ve got to also be with them and do these other things and you really look, yes, you can click decline on a meeting, but no one’s going to do that most of the time. There’s societal, not societal, social norms in an organization. You’re not going to decline people left and and also the word just decline.
(09:50): This is the other thing I don’t like about calendars is the language calendars tend to use. You’re not going to decline somebody. That’s just a very negative thing to do, so why would you press that versus can’t make it? Or I’m working on something else or there’s all these other types of languages and if we eventually go in this direction with our calendar, I’d like to go in that direction with language as well, like giving people ways to respond to the request. It’s not just decline. It’s like, oh, well I can’t do this or I can’t do that, or I’m doing something else or I’m going to skip this one. That’s how people would say it in person, but digital calendars are so rigid and they’re so presumptive and they give you just one option basically, and I think that’s one of the reasons why people are afraid to press it, frankly.
David (10:41): I think the decline is probably one of the least pressed buttons in all of UI design. I think if it was a physical object, it would just be covered in cobwebs and dust and so on because no one would’ve touched that button for years on end. I think Kimberly, this also attaches to, Jason had this viral Ted talk a number of years ago, why work doesn’t happen at work. This sense that the main time when we talk about work, it’s actually not available for work. The time that’s available for work is after work or before work, which is just such a screwed up notion that you cannot get work done either at work that was about the physical place, but it’s just as much as you can’t get work done during work hours because work hours fill up with all this other gunk that steals your productive capacity and not just even time.
(11:37): I think time is part of it. Jason, you have this wonderful contrast that there’s time and then there’s attention. And for me, if I can, two meetings on a day, the attention of the day is gone. I cannot that day for the kind of peak, high shelf, deep dive, whatever you want to call it, move the ball forward, creative work because the attention has been diluted and it just took two one hour sessions. There’s eight hours in a day. What you should have six hours left over. Yeah, I have six hours on a stopwatch. I don’t have six hours worth of attention left anymore. That has been disrupted, stolen, taken away. Which is also why this connects to the notion that the most powerful tool any entrepreneur has in particular entrepreneurs because there’s so many things coming at them at the same time is no. No, I don’t have time for that coffee meeting. No, I’m not going to jump on a Zoom call with you. No, I don’t want to hear a presentation about your product. No, no, no, no, no. That’s the only way to keep sanity and forward momentum having.
Kimberly (12:46): Okay, so we’ve talked about the, we don’t have a shared calendar. No one’s just putting time on your calendar. Jason, you mentioned, I mean even individually, if someone wants to schedule time, you reach out and kind of negotiate it. How does it work at 37signals for department meetings or even a company-wide, every six weeks we do a company-wide standup. How do those kind of scheduling things work at the company?
Jason (13:06): Yeah, I mean, different teams handle this differently. For example, the design team has sort of a standing optional meeting on Thursday mornings. Actually now it’s not even Thursday mornings. I forget which morning it’s, it’s been moved because we’re doing the HEY thing now, but there’s kind of a standing thing and it’s totally optional. And basically at every call, 25% of the people don’t make it. They’re like, yeah, I’m busy. I’m working on something. In fact, the answer typically is like, you know what? I’m heads down on something that’s more important, frankly. And nobody’s offended and nobody feels bad about it. It’s like, okay, they can’t make it. They’re working on something. And most people are like, yeah, me too, or I’ll jump in for a little bit. It’s like this more this social hour kind of thing than it is anything about business or work.
(13:47): So most of the things that when people get together in mass here, it’s a social thing, which means it’s optional. Social things are always going to be optional here. The all hands, every six to eight weeks or so, we tend to do it during the cool down between cycles. I mean if you don’t show up, I don’t really care. It doesn’t matter. Most people show up, but it’s an hour. We share some things that have been going on, people have questions, and if it ends early, it ends early. It’s not a big deal, it doesn’t go long, that sort of thing. We make sure it doesn’t go long, but there’s not three of these a day. There might be one of these a week that you’re part of or this call, we do two of these every week. We record two podcasts. This takes about an hour-ish, and that’s a standing thing, but we’re producing something, so that feels like this is not a meeting, this is a production. So yeah, I think different teams, I think support sometimes has a few more things that, or different people get together, but every team’s on their own on this. And the key thing is that it really should be optional. And everyone understands if you can’t make it, it’s not because you don’t like anyone in the meeting. It’s like you’re doing something else that’s more important and we have to default or defer, I should say sorry, defer to what individuals think is important to them in their given day. And that’s that. That’s how it works.
David (15:04): I think it is also fair to say that as much as we talk against meetings with quite the fever, we do it against a backdrop that is most people’s days being filled with meetings. Most people’s weeks, months, years are just jam packed with all this stuff. It’s not that reaching zero always for eternity is the ultimate outcome here. Just like we really enjoy meeting in person twice a year to recharge. I also do think it is important to occasionally have that connection, even if it’s just over a video call with someone else on your team and just where you can, you know what? I’m not just working here alone in a vacuum, in an orbit, but it should be coming as a pull from you. And this is why that optionality is so important that I am going to this meeting or social hangout or whatever we have a week because I would like some of that.
(15:58): This is very different if you ask most people about their feelings on meetings in general, there’s way too many. There are the views that didn’t need to be there, all this other stuff. That’s not a typical reaction someone at 37signals will have, they will be like, I will opt into this. I will enjoy going to this because I could just vote with my feet and sort of walk out or not come if it’s there. Which is also what’s sort of interesting. We put all these standing gatherings in Basecamp. They don’t actually go straight to your calendar necessarily. You can then choose to go like, alright, add this one to my calendar. And if you don’t, totally fine too. There’s no decline button. There’s an opt-in. I would like to have this on my personal calendar because I want to show up. There’s not a, oh shit, if I push the client to the six week, Jason’s going to see this. We can’t even tell. We use Zoom and there’s like three pages of Zoom. So whether you’re there, you’re not there.
Kimberly (16:57): Yeah, and I mean, that’s exactly how it’s posted. Here’s the calendar. If you want this to appear on your own personal calendar, add yourself to it. And that’s the end of the conversation.
David (17:06): Yes.
Kimberly (17:07): Okay. Question, Jason, for you before we wrap up about this calendar product that we’re working on. Have these ideas around your own time and focus time affected how you’re developing this product? Are there other things that have kind of given you ideas about how you want this calendar product to develop?
Jason (17:25): Definitely. They have, and I’ll give you one small example. Something we show on the calendar is uninterrupted blocks of time. So most calendars of course just show the events and when they happen and the duration of individual events, we’re actually showing the duration of non-events. We’re showing how much, there’s four hours between this and there’s two hours between this. I want you to always know how long the blocks are between things and if they get too small, you’ll know that too. Now you can of course see it visually, but it’s nice to also have those counts. So this is a small little thing. There’s many more things around this, but that’s a small little thing that we have on the day view. For example, it shows you how much time you have between things, how much free time you have between things. And initially the idea was, and this still could be the idea although we don’t have this fully flushed out, is that your day begins with what we call basically, let’s call it 24 hours of free time, and you have to carve out time out of your free time to add an event.
(18:25): It’s not that the day is blank, your day is actually full. Your day begins full of your time, and every time you put something on there, you carve something out of your free time. So we’re trying to figure out how to, we had a design for that and it turns out that it wasn’t quite delivering on exactly how we wanted it to work, but conceptually, that’s the idea we’re approaching here, which is you have your time and you’re losing pieces of your time when you give it up to something else.
Kimberly (18:52): That’s exactly what I was looking for, were some spoilers on the HEY calendar. So thank you for that. Cool. With that, we’re going to wrap it up. Rework is a production of 37signals. You can find show notes and transcripts on our website at 37signals.com/podcasts. You can also watch full video episodes on YouTube and Twitter, and if you have a question for Jason or David about a better way to work and run your business, send us a text or leave us a voicemail at 708-628-7850. You can also send us an email to email@example.com. Make sure you’re following along on Twitter @37signals, Jason and David, because we’ll be talking a little bit more about the calendar as time goes on.