When you're deep in the weeds working on something it's difficult to pull back and ask why.

Show Notes

Are you doing work that matters or are you just doing what you think you should be doing? Sinking too much time into something that you should have quit working on weeks ago is an easy trap to fall into. Avoid it by asking yourself some simple questions:
  • Why are you doing this?
  • What problem are you solving?
  • Is this actually useful?
  • Are you adding value?
  • Will this change behavior?
  • Is there an easier way?
  • What could you be doing instead?
  • Is it really worth it?
Show Notes

What is Rework?

A podcast by 37signals about the better way to work and run your business. In Season 2, we're going through Rework (the book) chapter by chapter and talking with authors, Jason Fried and David Heinemeier Hansson, about what's changed in the world of business over the last eleven years since the book was published.

Shaun Hildner (00:01):
Welcome to Rework the podcast by 37signals about the better way to work and run your business. I'm Shaun Hildner, and as always, I'm joined by 37signals co-founders and the authors of Rework. David Heinemeier Hansson. How are you?

David Heinemeier Hansson (00:13):
Good, Shaun.

Shaun Hildner (00:14):
How was the race?

David Heinemeier Hansson (00:15):
It was, and I was happy with my performance. Let me just end it there.

Shaun Hildner (00:20):
That's all you can ask for. And I'm also joined by Jason Fried. How are you, Jason?

Jason Fried (00:25):
Good, thanks. How are you?

Shaun Hildner (00:27):
Good. Well, this week we're talking about the essay titled Reasons to Quit, and it's all about making sure you're doing the work that matters, making sure you're doing good work, right? And the way you lay it out is this series of questions that you should be asking yourself while you're working on something. So, I just want to open up by asking, when you're building, how often are you checking in with yourself? How often are you're asking yourselves these questions?

David Heinemeier Hansson (00:52):
I think for me, the questions don't start until things are slightly off track.

Shaun Hildner (00:58):
Something goes wrong first.

David Heinemeier Hansson (01:00):
Well, it does not to go wrong. And like wrong is a big word. That sounds you're totally off into the weeds. But if you just start swerving a little bit, then you start asking, why are we doing this, right? We have all these questions, but I think the moment begins when things aren't quite right. And oftentimes it's just this slightly nagging feeling that you're not fully on the right track. You haven't cracked the nut fully things are maybe taking a little longer. They're a little harder. You keep hitting issues. Maybe sometimes you're even revisiting issues. You thought you'd clarified. That's when it's time to just go like, wait a minute, this isn't a set of questions. You need to gate everything behind where we have to do a five-wide root cost analysis on things that are going well. When things are just swimming along and going fine, you don't need to ask these questions.

David Heinemeier Hansson (01:51):
These questions are here to prevent you from chasing some cost. They're here to prevent you from just doubling down due to the inertia of moving forward. Well, we've already begun. Therefore, we must finish. Absolutely not. This is what we're talking about here. Just because you've begun does not mean you need to finish. In fact, in a lot of cases, the best course of action is to quit. Is to say like, you know what? We tried, we learned, and it wasn't it. And we've actually had a couple of those recently at Basecamp where we kick off on something and maybe the whole project then turns out to be, actually, once we start asking the questions, given the difficulties we've hit, it's not worth it anymore. And other times it's a way of carving off parts of the problem. You start asking, how important is this thing we talked about? We wanted as part of it because it's really dragging everything down. It's really adding a lot of drag to sort of the main path we're going on. Maybe we don't need it.

Jason Fried (02:53):
I think another way to look at it. I agree with all that. And then there's also reasons to quit part of what you said you were going to do. So, that's something we do a lot, which is here's this idea. We're building it. We get to this place where it's harder than we thought, or we didn't consider this, or we're running low on time. Can we quit part of this? Can we quit a piece of this? Can we do 80% of that? Can we leave something out? So, there's like micro-quits along the way too, which is what we call scope hammering, which we do. We also do occasionally quit the whole thing. But I think most of the time we micro-quit along the way basically. And I think that's the healthy thing. Otherwise, you set yourself up to essentially punish yourself to try to get things done that you can't or do not allow new information, to change your perspective or point of view as you go.

David Heinemeier Hansson (03:48):
And I think that's really the essence of this. It's a pushback against the heroism or perseverance that, oh, whenever the going gets tough, you just got to keep going. That is often total bullshit. When the going gets tough, oftentimes you got to quit. You got to go the other way. And this is... I think a trap that a lot of entrepreneurs in particular fall into because there are a lot of things that genuinely are hard and sometimes you do have to push through. But then there are a lot of times when things are hard and they're hard because you're making them hard. I'd actually go as far as to say that more than half the time, when you think things are hard, it's because you are making it hard. You are choosing a path that's difficult and there's another path right next to it. That leads to the same, goddamn destination that's completely clear.

David Heinemeier Hansson (04:41):
And you could just walls down with no effort, no heroism, no perseverance, just a change in perspective. And I think this is really what gets me going is this sense that like, "You know what? This doesn't feel right" We have all these sayings for the basecamp, are we cutting with the grain is one way we usually frame it, right? When you cut with the grain, the cut goes easy. If you're cutting against the grain, it just keeps being difficult. It keeps having tension and opposition.

David Heinemeier Hansson (05:13):
So, one of the questions here and we can go through all of them, but for me, the one I usually reach for is there an easier way the key to, is there an easier way is not just, is there an easier way to get to exactly the same destination but is there an easier way to get to roughly the same destination? Because that's often how you get locked in. If you get settled very squarely on one way of doing it needs to be precisely like this. Yeah. There usually is only one path to that. But if you could be a little fuzzy or a little loose on the exact destination, there's a million paths to get there.

Shaun Hildner (05:48):
Yeah. We don't solve hard problems. We reframe the problem. So, it's not as hard to solve.

David Heinemeier Hansson (05:54):

Jason Fried (05:54):
And the hard thing about these points, of course, is that if I'm listening to what David just said, I would go, "How do you know when?" And the answer is like, "You kind of don't exactly know when it's an experience thing." You know when through experience. And so, you've got to do this a lot of times to really find your groove in it. I think it's become fairly natural for us. Not super easy, but fairly natural for us to sort of see the seams in the rock and know where we can cut basically or where we can tap to break something off. But it's not that obvious when you're first getting started. And I think also there's a degree of fear of we're not doing enough or we're not doing it well enough, or we're cutting corners.

Jason Fried (06:38):
Yeah, you are cutting corners. You may have to ship something slightly round instead of something perfectly square that's okay. But it's hard to know exactly when and exactly where, and there's no science behind it. It really is more of an art to figure out what makes sense. It's also based on resources. It's based on time, it's based on who's going on vacation for two weeks next month and you just don't have them available. There's a lot of these variables that are involved and it is very hard to figure it out, but you do figure it out over time with a feeling, I think.

Shaun Hildner (07:08):
And this is not a formalized process three weeks in, you're not sitting down and asking yourself this list of questions, right?

Jason Fried (07:14):
I mean, there's a point where you sort of must do it, but yeah, I don't think it's a formalized moment because things fall differently, work falls differently. I think it's always in mind, it's kind of in the back of your mind early and then it moves to the front of your mind, like migrates towards the front of your mind. The further along you're getting.

David Heinemeier Hansson (07:33):
I think one of the key points here too is having a thin skin is an advantage in this regard that you are sensitive to when things are not feeling quite right. If you have a very thick skin and you can just push through whatever you don't stop to ask whether we're going in the right direction early enough. And then by the time, you'll ask it's way too fucking late. It's just way too late. You're like, "Oh, we're supposed to ship two weeks ago and it's still hurting and we're still barely there." That's when you know you haven't asked these questions soon enough. I think that's a big part of it is when to stop, when to know and developing a thin skin is actually part of this.

David Heinemeier Hansson (08:17):
The other part of it is this is just easier to do the smaller you are. This is one of the things I think we've learned or discovered as we've grown the further, the distance between frankly Jason and I and the individuals making the decisions, the hard it is for those individuals to just go, well, I'm going to quit because we have a whole culture of like, well, you're not a quitter, right?

David Heinemeier Hansson (08:41):
And you want to present as I'm not a quitter at work and maybe I'll look bad in front of my boss who will then look bad in front of their boss. That's when it becomes really hard to quit when there are all these status angles in on it, which is why I think it's one of those areas. Another of those areas where this is just easier. It's self-evident when you're tiny when you're five people and one person isn't able to get there on the path that they're going, they're just all right, this isn't working. Sorry, I'm going to go the other way. Now, if you have two levels of reporting, it becomes a thing. And I think this is something we're still struggling with. Still trying to figure out how do we actually take this value that when we wrote it in Rework and it was even based on an idea prior to Rework, we were 12 people, 14 people we're favorite is in different struggles at 70 than we were at 14 with this, which is one of the reasons to talk about it.

David Heinemeier Hansson (09:42):
And also, to put up the example, we just had an example recently where we had a feature, we'd actually announced that we were going to ship. Jason had previewed it on Twitter or something. And once we started running through these questions, because it was overdue for a variety of reasons, the answer was just, no, we're not going to continue to pour more into it. And then, in fact, funny thing, we doubled down on our mistake, and we tried once more to pour another two weeks into it. Oh no. And that in the end turned out that the first instinct was right. We should have listened to our thin skin that said, you know what? This just isn't going to make it. And then go like, do you know what? That's a thing that happened sometimes and you should look at it and why did it happen? Learn from it.

David Heinemeier Hansson (10:24):
But the fact that in and of itself, something doesn't ship because you can't answer these questions in a satisfying way can actually be a victory, right? You demonstrate to the organization, we are willing to give up. So, next time, when you face these concerns and you have this, "Ah, do you know what? We're off on a tangent here." You don't just push through you. Don't just bet on your thick skin, you go like, you know what? Giving up is an option needs to be on the table next to restating the problem next to doubling down, doing whatever it takes. And it needs to be as valid an option as the other two.

Shaun Hildner (11:00):
Another tool in your toolbox. Yeah. Well, let's do this really quick. Let's go through the questions. Y'all layout that you should be asking yourself when things do start to go a little right. I'd like to get some sort of comment on the importance of asking yourself the individual questions. So, we're going to start with, why are you doing this in the first place?

Jason Fried (11:20):
This is kind of the fundamental one around like, why did we choose to do this work? What's the point of this feature? Who's this for? And the answer could be it's for us. The answer could be, we just think it needs to happen. It's not like there's a right or wrong answer, but you better know the answer. Otherwise, your sort of aimlessly just wandering around. And I think we get to this sometimes when we don't fully explain the reasons behind a choice, we're actually running into this right now with some pricing stuff we're exploring as sort of assumed someone knew something. This is not quite the same thing, but it's similar.

Jason Fried (11:54):
I assume someone knew something because I'd said it to about 15 people so far. And it just turned out that one person wasn't one of the 15, I just assumed he knew it's a feature, but there's a reason behind it. And I think that when he saw... We started talking about it and he goes, I don't really understand why we're doing this. I hadn't made it clear. The reason why it's part of the thing. Now we may not end up doing I'm being very vague here, but we may not end up doing that piece, but I could see how he was like, why are we even doing that? It just wasn't clear why we were doing that. And so that happens sometimes.

David Heinemeier Hansson (12:26):
When you have that at your fingertips, the why. The context for cutting becomes much clearer when you don't know why you're doing something and you just like, this is the thing I'm doing. You don't know what's really the epicenter of it. What's really the crux of it. What's the crucial point of that idea? The more broadly you can distribute that context, the more you enable everyone working on the problem to come up with a novel solution that fits the why, that fits within. Yeah. Okay. If you take that bit out, it's no longer the thing. You've taken the ever epicenter out of the feature. It's no longer the feature itself. So that why provides that foundation for making the harder calls. So, it's almost like it sets up these other questions we then ask afterwards.

Shaun Hildner (13:13):
So, the next question you should probably be asking yourself is what problem are you solving?

Jason Fried (13:18):
Yeah, this one's kind of, I think, related to the first one, in a sense.

Shaun Hildner (13:23):
They're all kind of related.

Jason Fried (13:24):
Yeah. Well, they are all kind of related. I think this is again, getting back to why are we doing this? And if we didn't do it, what would happen? I think this is another question to ask. We got back to quit or not quit. Like the earlier part of this conversation is like, what if we just didn't do this at all? This, this feature that David was talking about before was this thing called my side, which is this idea of moving a bunch of things to a sidebar that we actually already had somewhere else on the app, or it's sort of moving it to a different place. And it's like, we want this, but what if we didn't have it? Well, if we didn't have it's all still possible right now. It's just a little bit frustrating to get to, but it's there. So, it doesn't feel as much of a loss, not to do something then to do something, you can't do it all and then get so close to it and then say, we're not going to give it to anybody because we didn't get it done.

Shaun Hildner (14:10):
So, what was the problem my side was supposed to be solving?

Jason Fried (14:12):
It was supposed to put things that you would want to see more regularly at your side. So, you didn't have to go somewhere else to see them and leave where you were. If I need a list of things that I need to do, I want to have that by my side. Like you might put a notepad by the side of your laptop to see like, have a list of things that you can refer back to, without having to leave your place each time. And there's some other things as well, but we can live with what we have. It's just not as good. It would've been a different thing if we didn't have any of those features at all before, and then we didn't get to them at all. I think there's just a different degree of penalty to quitting there. When we already had some of this stuff to begin with, we felt we would live with it, even though we wanted the other thing more.

David Heinemeier Hansson (14:53):
I think another reason to ask that question is when you're solving someone else's problem, that's when it's really important to ask, have we actually understood the problem? What is the actual hurt? Because this is something that often happens with feature requests. A user will bring something like, could you put this feature in there? And maybe you just go yeah, sure. We should have that in there. And you start working on it and maybe you're cutting some bits, but that was a request for feature. It wasn't a presentation of a problem. What are you trying to do that you can't do or when you're doing it hurts? Oftentimes you'll find that there's not a straight connection there between what the problem is when someone is proposed. And if you just accept their proposal for what the software should do, you're essentially putting them in the seat of the designer.

David Heinemeier Hansson (15:40):
And if a designer is supposed to do anything it's to solve actual problems, not just make pretty corners on solutions delivered by customers. Not that customers can't occasionally come up with a good solution, but this is why we employ good designers at Basecamp. To take problems and then come up with novel solutions to it. But to do that, you have to know what is exactly the problem here. As we ask in the essay, is it that you're confused? Is it that there's something you can't do? Is it a sort of a smoother path you want it attached? You do all the time that you want more easily done if that's, so maybe it's an entirely different feature you want, you don't want just to pave the road a little better on this one. There's you could also just fly there, right? There's a bunch of different ways to do this.

Shaun Hildner (16:27):
What about, is this actually useful?

Jason Fried (16:30):
Yeah. I guess they're all kind of the same question.

Shaun Hildner (16:32):
This book is mostly padding anyway, right? Jason, is that what you're saying?

Jason Fried (16:36):
The thing is they are subtle. There's subtleties between them and they're really just slightly different lenses on the same question.

David Heinemeier Hansson (16:42):
I think the one to pull out for is it actually useful is confusing enthusiasm with usefulness. I think maybe it was in getting real or something. We had that is that oftentimes you just, this is on the deck. You're doing this because in the moment you were really enthusiastic about it. And now six weeks away from that decision you're like, yeah, I don't know. I could take it or leave it.

Shaun Hildner (17:05):
Are you adding value?

Jason Fried (17:07):
I don't like that one anyway.

Shaun Hildner (17:08):

Jason Fried (17:09):
I don't actually like that phrase.

David Heinemeier Hansson (17:11):
No, I hate it. I hate the word value actually.

Shaun Hildner (17:15):
Why is that? This is a fun thing to dive into. Why is that?

David Heinemeier Hansson (17:18):
It's so cookie-cutter. It's so abstract. It's calling what we are doing right now, content. Oh, we're just sitting here producing content. Are we sitting here producing value. It sounds like you're saying something, but you're not saying anything. Value is such a feel good. Everyone wants to create value. When you're at that level of abstraction, there's usually bullshit going on. I would actually. And you were saying, what's the filler here? That one is the filler.

Shaun Hildner (17:48):
Cut that one. Okay.

David Heinemeier Hansson (17:49):
In the next edition of Rework, we will have cut. Are you adding value paragraph six from this essay?

Shaun Hildner (17:56):
I think this one's pretty interesting. Will this change behavior?

Jason Fried (18:00):
I'm trying to remember if this is probably related to numbers and counts. If you were to put the number six next to something, does it matter? Do you need that information? There's a tendency to like, want to surround bits of content. Oh, God. Bits of stuff with metadata and stats. And there's just all this stuff. And it's like, does it matter? What's interesting is with HEY, we decided against counts basically everywhere, except in the screener, because these are emails you haven't seen and you can't see them until you go behind some, you click a button to see them. So, it gives you a sense. There's something, one more. There's two more that I haven't seen. I need to do something here. And we just last week added account to threads that have multiple replies to them.

Jason Fried (18:50):
Which is actually something that I'd personally been missing. This indication that this is a thread with replies that there's more people involved here. It's not just a one off. Became hard to identify certain threads without some degree of that. It's not even the count that matters quite as much, but it was sort of the best way to have some sort of indication that didn't maybe mean something else. So, we brought that back, but that's it. And so, I think what we could have surrounded HEY, with tons and tons of counts and we decided not to do it. Because we didn't think it would really change behavior much or it would change behavior negatively.

David Heinemeier Hansson (19:23):
The kicker here is impact. Does it change how someone uses the product? And I think this is particularly one for us with Basecamp because Basecamp has been around for a long time. Even this version of Basecamp been for quite a while. You can absolutely make a product worse. As Jason said, by adding a bunch of count to the UI, right? You make things busier because you keep adding to it. What you should be asking yourself is this going to have an impact on the changes how people use this product. Obviously, in a positive way, is it adding value?

Shaun Hildner (19:56):
We already discussed this one a little bit. David, I think you said this was your favorite. Is there an easier way?

David Heinemeier Hansson (20:01):
Yeah. That's just basically the stand in also for this thing we call judo. We're trying to do something that's hard. Can we use that energy and turn it into a throw somehow? That's my favorite. That's my go to actually of all the questions. Because as we said at the beginning, we started asking these questions when there's a nagging feeling that maybe we're not going to sail right through. I always go to like, is there an easier way? And it's not necessarily, is there an ultimate easier way? In fact, Jason and I just had a thing this morning on a thread in Basecamp about the pricing thing where Jason presents a problem, we talk back and forth. And my first instinct, this just like, you know what I accept that problem as stated is true, but could we start somewhere easier?

David Heinemeier Hansson (20:42):
If we start somewhere easier, then at least we will be going, we'll have some momentum we're rolling. We can always add that thing on later. Or at least you realize later, do you really want it? And if you get there and you really want it, great, fine. Just do it. It will cost you nothing. But you might very well have saved a trip because, by the time you get there, you realize, well, maybe that thing or the other thing you didn't really want it anyway.

Jason Fried (21:03):
That would be a fun discussion to have to debate as a podcast bonus to debate that point. Because I agree with David, but I also think to me, there's some magic that we're losing, but the alternative is we're not going to get any magic at all. If we can't build even the simpler versions, but the thing that's always difficult about those decisions is that it's rare that we go back and do something again and revisit things again, because there's always more to do. And so, I'm always nervous about losing the magic in the initial version because you rarely come back and paint the magic in later. It's just harder to get back up and do that again when there's so many other things pulling for your attention. But yeah, that's a great example. And again, we're being abstract here, but...

David Heinemeier Hansson (21:47):
The point with all these questions is not, yes, no. Is to explore the tension that they reveal. Explore the tension. Is there an easier way? And then Jason going, yeah. There's an easier way, but that's going to lose the magic and then you explore that tension. You discuss it from those two points.

Shaun Hildner (22:04):
Like the act of asking yourself the questions is the benefit.

David Heinemeier Hansson (22:07):
Right. And then under the umbrella is this is about the art of the possible. Well, you can have all the magic you want, if it doesn't have to ship.

Shaun Hildner (22:15):
Right. I could promise anything.

David Heinemeier Hansson (22:17):

Shaun Hildner (22:18):
Jason, I know you've talked about this, especially in the last episode quite a bit. What else could you be doing?

Jason Fried (22:24):
Yeah. This is just about opportunity costs and trade-offs. The thing is whenever you say yes to something, you say no to everything else. I mean, like literally everything. And so that's why choosing what you do who's, you should choose carefully and thoughtfully part of this though too, is the benefit of sort of the way we work, which has its downsides as well. And it's not perfect. But is that when you say yes to something, you're only saying yes to it for a maximum of about six weeks. What's scary is that when you say yes to something and it's going to take eight months to do, that's a huge commitment to say no to so many things for so long, we can say no to a lot of things but revisit all the options again in a month and a half. So, it just takes some of the sting off the scary moment of saying yes.

Shaun Hildner (23:12):
And then finally, is it really worth it? And this might be the most abstract, how far down this line of questioning do you have to go before you're like, oh, I mean, is the whole thing worth, just giving up right now?

Jason Fried (23:24):
Part of it is you never really know. Because there's counter-narratives and counterfactual, unless you do both, unless you do it and don't do it and have two parallel universes, it's actually pretty hard to know. You can look back and run the stats and do all the stuff to me it's really about, was it enjoyable? Do we enjoy doing the work? Do we think it improved the product from our point of view? Would we do it again? It's that kind of stuff versus like proving that it was worth doing, it's kind of hard to prove it.

Shaun Hildner (23:51):
This drove 40% more signups or something like that.

Jason Fried (23:54):
And then that can happen. And there situations where that certainly is more measurable than others, but ultimately over the long term, you have to enjoy the work. So even if it drives the 40% signups and you fucking hated the project and every project you work on, you hate, but it's good for the product. It's just, not worth it.

David Heinemeier Hansson (24:12):
I think that's why it's the ultimate question of all these questions. Yeah, because this is really the one, we sit with at the end when we're making the determination to stop or not stop, is this worth it, are we so far into the weeds here that we're just like, I don't want to be here then bail and don't dread bailing celebrate bailing. In fact, if you don't have a culture and a company that can accept bailing on a project, you have a problem and it's not healthy. It is absolutely healthy. You just almost do it as a ritual, which is why to some extent, we savor the opportunity to bail when it finally comes up, because we ship the vast majority of everything we work on. So, when they're finally an opportunity to go. Do you know what? This just isn't worth it.

Shaun Hildner (24:58):
Yeah. It's almost celebrated.

David Heinemeier Hansson (25:00):
Exactly. It's like, hallelujah. That's a thing that needs to happen occasionally for us to revisit how we work and why we work such that we can wake up at the end of a cycling and go like, do you know what this was pretty good. Yeah. I like what we got going here because we bailed when it wasn't worth it.

Shaun Hildner (25:16):
Well, perfect. We're going a little over long here. So, I think we're going to skip listener questions this week. I do have a ton sitting in my inbox, but if anyone would like to ask a question of Jason or David, leave a voicemail at 708-628-7850 or better yet, record a voice memo on your phone and email it to Next week, we're talking about interruptions as the enemy of productivity. And just a sneak preview the week after that is the famous meetings are toxic chapter. So, I hope you guys will both join me next week. I want to say thank you to Jason Fried.

Jason Fried (25:55):
Thanks, Shaun.

Shaun Hildner (25:56):
And thank you, David Heinemeier Hansson.

David Heinemeier Hansson (25:58):
Thanks, man.

Shaun Hildner (25:59):
All right, we'll see you next time. Adios.

Shaun Hildner (26:10):
Rework is a production of 37signals. Our theme music is by Clipart. We are on the web at, where you can find show notes and transcripts for this, and every episode of Rework. We're also on Twitter at Rework podcast. If you're following along in the book, next time we'll be discussing the chapter. Interruption is the Enemy of Productivity. And if you like the show, I would really appreciate it. You would leave us a review on Apple podcast, Spotify, Overcast, or wherever you're listening to this.