does deep work actually work?

You've probably noticed that whenever you come across a productivity hack or a trick that, you know, helps you to knuckle down and focus on actually do the work that you're supposed to be doing instead of endlessly doom scrolling. You may notice that productivity hack does actually work initially, and it's really exciting. But things revert to the mean. And after a short period of time, maybe two weeks, or if you're unlucky, just a few days, you'll find that it no longer works and no longer forces you to work, which is a pretty human failing, I think. And so we have to ask the question, does deep work actually work, in the long term? And that's what I'm going to chat about here.

So in my experience, deep work is the most productive kind of work that you can do as defined by Cal Newport. And, basically, I think Cal Newport was fundamentally right about everything. His predictions were frankly way early and really, really correct. So for background, Cal Newport is a computing science researcher. And while he wasn't involved in this garvey of GPT and the underlying computer science, he basically saw the general trend of AI coming along and automation coming along and predicted that everybody was about to be automated out of the low level jobs. And that after that happens, the only durable long term competitive advantage that you can have these days is going to be your ability to focus and do really difficult work that requires concentration that very few other people are able to do for a long period of time, which is essentially what deep work is. And so, you know, he wrote this quite early in the piece (to do lookup date later). And then, actually, it turned out to be true. And so, yeah, let's talk about does deep work actually work?

Honestly, the title of this article is chosen to be highly SEO optimized and something that people will be looking for. And so I won't directly be answering the question, does deep work work? Of course, it does. If you do the work, then you've done the work. But the real underlying motivational question that you're probably much more interested in is, how can I get myself to do deep productive work even when I have a history of being extremely undisciplined about sitting down and doing long periods of valuable work. So the answer to that question is, really, how can we get you to do more deep work? And that's definitely difficult.

But before that, we actually have to dive into a necessary requirement, is that do you even know if you're doing deep work? I would say if you are or you are not, you're gonna really struggle to feel either satisfied or unsatisfied with your level of progress unless you actually track how much deep work you're actually doing. If you have no means to track it, then you don't even know if you're doing well or poorly. And so, of course, the first step is to track, you know, how much deep work are you doing, how often, and how consistently. And so, of course, enter Deep Timer.

And so if you have cofounders, or to some extent, you have employees around you, they will sort of naturally, by virtue of being human and observing you, will force you to sort of, you know, knuckle down and do some deep work. It's sort of difficult to come into the office every day with your teammates and just faff around for eight hours or more. And so in my experience, that's been the single biggest lever that you can possibly pull to force yourself to do both busy and deep work.

So if you have those cocoas around you, that's good, but you still need to know, are you doing busy work mostly or deep work? And so that tricky question is how do you track it? If you have a boss in a nine to five job, then you are forced to record your time using time sheets so that you can get paid. You really don't wanna use the time sheets, and there are really bad annoying sort of process to go through. But because it's being forced upon you, you don't really have a choice, and you will do it consistently week after week. However, if you're the founder or you're a freelancer, there is no boss making you fill in the time sheets, and it's not so that you can get paid. And so the default is that you simply will not actually track the amount of work you're doing, let alone how much deep and shallow work you're doing.

So we need to introduce a tool that will allow you to do that even when there is very little motivation for you to do so. So that was the genesis of Deep Timer as a hardware product. The goal is to make it as simple and low friction and low distraction as possible so that even in the most distracted, busy circumstances when you're working on a whole bunch of different things and you just don't have the mental bandwidth to resist opening your laptop and seeing over nine thousand tabs and then getting immediately stuck and lost into a whole bunch of different email threads, you can still, you know, just reach over, push the red button or push the blue button for busy or shallow work. And because there's no screen on it and no real confirmation, you just sort of forget about it and trust that the time was tracked.

So that's what we're going for here. So this product is well suited if you're a solo founder or a cofounder who's given high autonomy and freedom over their own time. And it's not so much that you're reporting to someone else, but that you yourself are personally deeply invested in whether you're doing lots of busy work or deep work. You just want the minimum amount of friction to track that.

Bonus question. How can you force yourself to do more deep work? So I found that historically, all these little productivity hacks, like using a Pomodoro timer or, you know, making your DNS block the Internet or turning your phone off or putting it in the fridge, or any of these sort of little tricks, they all work for a short period of time, which is great, and you should do them, maybe set a deadline on them so that you can get the maximum value out of it before it wears out and you give up. So, for example, decide to use Pomodoro for, you know, just one week, and at the end of the week, you're free. And so it's easier to hold your breath, so to speak, for just that one week rather than mentally committing to it, you know, "forever."

And so aside from little hacks like that, the single most long term consistently effective hack that I found is to have accountability and consequences. That is to say, you have to make a bet with your friend that you will hit six hours of deep work today, for example, or that you will, you know, start work before ten AM and... or you owe your friend, you know, twenty dollars or a hundred dollars. And it doesn't have to be a lot of money. In fact, I've done this with a bet of a thousand dollars, and I would say that I probably failed equally as often on the thousand dollar case as the twenty dollar case. It's really what the magical effect here is, that when you say to yourself or to your friend, oh, yeah, I will definitely start at ten AM, it's really easy to over commit and say nine AM or eight AM. But then suddenly, when you introduce external consequences and reality confronts you, suddenly, you know, when you risk the prospect of losing money or committing to embarrassing failure, then suddenly it forces you to readjust your estimate of what you're willing to commit to. And so you have a much greater level of success, and that psychologically makes you more likely to stay on the train rather than just constantly falling off. And so I think that's the secret to this trick, why it keeps working is because the consequences continue and it forces you to pick more realistic commitments and goals.

So I highly recommend getting another cofounder buddy of yours, someone that you know and respect, ideally rather than just a rand dough on the Internet, and, yeah, commit to them to say that you'll both start your deep work before ten AM, say, and there are no excuses unless you, you know, message twenty four hours beforehand to say that you're sick or traveling or, you know, whatever. And that has worked for me the best, and this is a trick to sort of get some of the benefits of having a cofounder, maybe a major chunk of the benefits of having a cofounder, without actually having to have a cofounder involved in your business. So that's the trick that I found most consistent over years of effort. Do with that what you will.

But remember that in order for this to work, it's totally possible for you to still underperform by not doing enough hours. And so it's certainly, if you're not really working very hard at all or not working every day, then making it bet to show up at ten AM every day will really improve that, but it won't get you to the insane sort of work ethic that you need to succeed at a startup or indie hacker business. And so in order to do that, you actually do need to track it. And it doesn't matter if you use a spreadsheet or a piece of paper, or you just, you know, very roughly estimate the amount of time that you worked by defining working as you walked in the door at the office versus you walked out, and anytime mucking around in the office is just counted as productive time. It's not a bad solution. It could be improved.

And, certainly, I found that deep time are toggling on and off deep and busy work, having very fine level of reliable manual tracking so that I fully trust the numbers really, really helped. And, certainly, there are automatic time tracking tools out there that automatically look at your screen and decide what you're working on and trying to categorize it for you, but I just can't take them seriously, and I don't trust the result because I didn't enter it myself. I sort of inherently think that the system will get it wrong. And maybe that's partially correct, or maybe I'm just behaving like a boomer and that I should trust them.

But either way, psychologically, once I press that button, there's a huge advantage to knowing that I'm locked in for the next hour long. And I also noticed the secondary advantage is that once I've pressed a button of deep work, or once I pressed a button of shallow work, and I'm deep into that shallow work, and I get the urge to just start coding or doing some deep work, I said if there's a little bump in my mind, there's a little mental bit of resistance that prevents me from just rapidly flapping backwards and forwards between different types of work, it sort of helps me to stay on track or at least on task. And vice versa, if you're in the middle of deep work and you wanna just quickly check your email, you know, and you reach your hand, reaches for the... blue button to say shallow work. You know, you sort of physically are reminded, oh, wait. You know? Maybe I don't wanna switch to shallow work right now. Maybe I just wanna continue on for another hour or until this one bit is done. And so, yeah, I find that's also advantageous.