does deep work actually work?

Whenever you come across a productivity hack or a trick that 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 the hack does actually work initially. It's really exciting when it does.

But eventually things revert to the mean.

After a short period of time, you find that it no longer works. Somehow it no longer forces you to work, to do what you should be doing. We acclimitize. Maybe you get two weeks out of your hack. Or if you're in a very undisciplined time of your life, or especially directionless, then maybe it'll falter after just a few days. This sucks and is basically the part where Sisyphus loses grip on the boulder near the top. 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.

Short term hacks that do work

Rather than trying to should yourself into doing it. Instead, think clearly and rationally about it as a specific problem, that another employee is having, and come up with new changes, new things to try. Do not think of it as a personal failing of effort and motivation "I just need to try harder" or an identity problem "I am bad". Stop changing nothing and expecting yourself to become super productive and hardworking.

Suppose for a moment, that that approach did suddenly, miraculously work, after years of trying to no avail. I suspect it would feel a bit like an unearned victory, motivation delivered deus ex machina from up on high, where <insert motivation speaker> et al dwell. You are now productive without having brought it about by your own doing. Some people would take that win, but I'd feel robbed of the triumph of overcoming my own unproductive nature. Perhaps I should be more rational. The point is to cross the swamp, not fight all the alligators. In any case, that's not going to happen to you. You can safely assume you won't wake up tomorrow a different person for no reason. Expecting otherwise would be insanity, I'm told.

Better to earn your productivity by putting in the clear minded, rational thinking that is required to solve it as a problem. Fix the environment. Fix the incentives. Or decide it's not worth it and give up. Remove your distracting devices. Use pomodoros. Schedule time in.

Deep Work, for me, is a couple of hours of hard mental work requiring hard thought to make decisions. e.g. usually thinking deeply while writing some firmware, or deciding exactly what an app or website should be, do, look like, and corner cases it'll encounter.

If anyone and everyone can tell an LLM coding agent to "code me a productivity tool", then what separates "AI slopcoded mess" from "excellent product" is the depth of thought and decisions that went into it, informed by discussions from real world users. Basically, you need to do Deep Work.

Go and read 'Deep Work' by Cal Newport. Basically, I think Cal Newport was fundamentally right about everything. His predictions were frankly way early, and really correct.

For background, Cal Newport is a Computer Science researcher. And while he wasn't involved in the discovert of GPTs, he basically saw the general trend of AI / automation coming along and correctly predicted that everybody was about to be automated out of the low level jobs. The shallow work. And that, after that happens, the only durable long term competitive advantage that you can have 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. He made this preduction and wrote the book quite early in the piece, and then, actually, it turned out to be true.

Does Deep Work Actually Work?

Honestly, I chose the title of this article to be something that you will be looking for. I confess, 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 prize here, the real question underlying your question is actually, "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?"

To practically answer that in your real life, as in, right now, after you finish reading this article, we first need to dive into a necessary pre-requirement: do you even know how much deep work you're doing? I would say, step one, whehther you are doing deep work or if 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 record, measure or track, how much deep work are you doing. When. How often, and how consistently. And so, of course, enter Deep Timer.

Founders and extrinsic motivation

If you're an employee, don't worry about this, the deep work will probably get pulled out of you by your boss and your team, when it's needed.

If you're a founder with no boss, then it's only you who cares how much deep work you're doing.

Paradoxically, extrinsic motivation can force you to work hard on a task that you don't want to do, when it brings you no direct additional reward for completing it, and yet when you're workign on your own project, on a task that you really do want to do, intrinsic internal motivation can often evaporate and you can't force yourself to work.

You will fill in your crappy time sheet because your boss is asking you to

You will not consistently track your own time on your own beautiful spreadsheet that you made / time tracking software that you set up for yourself

If you have co-founders, they will naturally, by virtue of being human and observing you, force you to 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 10 hours. 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. Aside: To some extent, this is also true if you have employees around you, who are kind of on your level. But if they're way below you on the hierarchy / ability level, those guys will maybe not inspire fear and motivation into you as the boss. So choose accordingly, when doing that cold rational planning of what environmental change / extrinsic factor to try next, and set your expectations accordingly.

How much are you doing?

So let's say now you have applied some external accountability, and you're doing some amount of deep work. Now you need to know, are you doing busy work mostly, or deep work?

How do you track it?

A bad, frustrating process with high friction (e.g. manually filling in a spreadsheet laboriously) won't survive if it's just you trying to force yourself to do it.

That's why I created DeepTimer. The ideal tool would allow you to track deep work and shallow work, 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 deep thought or even a whole bunch of different things, it should just work. You are not always going to have the discipline, and mental bandwidth to carefully click "stop deep work" or "edit the end of that session to be 10 minutes ago" because the phone rang. You won'y always have the mental bandwidth to resist, when opening your laptop and seeing over nine thousand tabs and an urgent email that's just come in: before you know it an hour has passed. Or was it 30 minutes? Who knows. That's exactly my point. The days get frittered away with blocks like this and you have no real answer to "did I work hard today?".

With deep timer, you can just reach over, push the red button for deep work, or push the blue button for busy work. Done. Tracked. Because there's no screen on it, you can continue your flow uninterrupted.

So that's what we're going for here. Deep Timer is well suited if you're a solo founder or a freelancer or remote worker who's given high autonomy and freedom over their own time. It's for when you're 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, so that you do it consistently.

Does it work?

Returning to the question. "How can you force yourself to do more deep work?"

I found that historically, all these little productivity hacks, like using a Pomodoro timer, making your router block the Internet for an hour, or turning your phone off or putting it in another room on charge, or any of these kind of little tricks, they all work for a short period of time. Which is great. And you should do them, and also maybe set a deadline on each of them so that you can get the maximum value out of it before it wears out. e.g. decide to use a Pomodoro for just next week, and at the end of the week, you're free. This way it's easier to commit to holding your breath, so to speak, for just that one week rather than mentally committing to it "forever."

Outside from little hacks like that, the single most long term, consistently effective hack that I found is to have accountability plus financial consequences. That is to say, you have to make a bet with your friend that you will hit six hours of deep work tomorrow, for example. Or that you will be physically in the office before 10 AM, otherwise you owe your friend $20. Or a hundred dollars.

Some tips: Make sure it's reciprocal, or close enough to balanced. Make sure you include a mechanism that you have to acknowledge the failure, not just hand them the money next time you see them. 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 approximately equally as often on the thousand dollar case as the twenty dollar case.

Why does it work? Why does it work so consistently? The magical effect here is, that when you say to yourself or to your friend, "ohhhh yeah, I will definitely do 8 hours deep work and will start at 8AM", it's really easy to over-commit and then not do it. Do this as an excercise now, think of a specific goal of doing more deep work. Commit to it.

But now, obvserve your own reaction and fear when you suddenly introduce external consequences (Losing a $20 bet) and reality confronts you. Suddenly, when you risk the prospect of losing money AND committing to embarrassing failure, then it forces you to readjust your estimate of what you're willing to commit to. Like magic. And so you have a much greater level of success, and that psychologically makes you more likely to keep the chain going the next day too, rather than just constantly falling off. I think that's the secret to this trick, it keeps working is because the consequences continue and it forces you to pick more realistic commitments and goals, whick self-reinforce.

I highly recommend getting another buddy of yours (ideally doing their own project / company / startup). It should be someone that you know and respect, rather than just a rando on the Internet. Talk with them about it first, rather than just hitting them with the unsolicited "I will do 4 hours of deep work tomorrow or I owe you $20" text message. Chat with them and then make sure you both commit to something approximately the same size and shape of task, e.g. that you'll both start your deep work before 10AM, say. Don't get too legalese about it, but you can add some conditions like "there are no excuses unless you give 24 hours notice". Don't obsess over the details, simpler is better. That has worked for me the best, with a few friends that I look up to and respect, over the years. You'll also notice that this is a hack to allow you to get some of the benefits of having a co-founder without actually having one. Maybe even a major chunk of the benefits of having a shitty cofounder. So that's the hack that I found to be most consistent over years of effort.

Remember that it's totally possible to pass every bet and not acheive your larger goals. Results are the only thing that counts in the end. Here are two common failure modes.

Are you even doing deep work?

If you're not showing up every day, and not really working hard, then make a plan to change your environment and extrinsic motivations, and fix that right away.

You can show up at 10am every day without fail, while you to still underperform by not doing enough hours.

Make the bet and solve that right now. And start tracking your work hours, so you know if you are even putting in full time effort or way way less.

Tip: often you subjectively feel that you're working way harder than you are. If I don't look at my total hours for the week, my subjective estimate (no peeking) often is wildly off from the actual number.

This one is easy to diagnose. Start tracking your overall work hours from tomorrow.

Are you doing the right thing?

Much more commonly, you're doing plenty of hours, but you get nowhere, because you're not doing the right things, the hard things, the deep work, or the shallow work.

e.g. you endlessly code but avoid distribution and marketing.

Now that you've made a bet to show up to the coworking spaceat ten AM every day, has avoided the first faillure mode above, but it won't get you to the insane sort of progress and productive output that you need to succeed at a startup or lifestyle business.

In order to avoid working on the wrong things, and not enoughu on the right things, you actually do need to track it. It's a pain, I know. But it doesn't matter if you use a spreadsheet or a piece of paper, or you use an app. Just make sure that you consistently track it, and that you trust it when you refer back to it at the end of the day and week. If you can't reflect on it, there's little point.

Certainly, there are automatic time tracking tools for your computer 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. Does a phonecall count? What about switching from desktop to laptop? Do I have to fix the times up after? Do I remember? Bah. I can't shake the feeling that the system will just get it wrong. Maybe I'm just behaving like a luddite and that I should trust them, or maybe I'm right.

In any case, I found that having to physically, manually hitting the button on deep timer gives me a very fine level of reliable manual tracking so that I fully trust the numbers.

There's an advantage to having a physical hardware time tracker. Psychologically, once I press that button, there's a huge mental advantage to knowing that I'm locked in for the next hour long session, say.

After a few days of using it, I also noticed another secondary advantage: once I've pressed a button for 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.