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For me, deadlines work best if more people than me have a stake in the thing I'm working on.
Same. As Douglas Adam’s said “I love deadlines. I love thé whooshing sound they make as they go by” but if a deadline involves other people those consequences get me to care.
I think one fundamental thing I've learnt about management is that different people need different things.

I am like the author, a deadline helps me immensely. Yet at a place I worked at recently, there were very lax deadlines, that's because others felt too stressed by a tight deadline.

A good manager can understand who needs what and can set up the appropriate incentives for each team member.

This is the best take, IMO.

Different strokes for different folks, but frankly managers don't care if a deadline greatly encourages or greatly stresses their ICs. Either way, it's a way to hold people accountable for a deliverable at a certain date, or at the very least an update why it was missed.

Not having deadlines requires much more nuance to ensure a team delivers work consistently, and unfortunately nuance in work management doesn't report well

If you are going to do this it's best to advertise that fact in your job ads. You want people who like to operate in that atmosphere in return for something - promotion, perk or vision. Otherwise you just get high churn rate and poor productivity.
Great piece. I'm also one of those people who reads lots of productivity books, and tries out lots of tools. But I've come to realise the key to productivity is fairly simple - make sure you're really enjoying what you do. Then you'll get up in the morning and want to do it. You'll be able to focus. You won't get distracted by Twitter or whatever. But giving yourself deadlines is a great way to combat perfectionism. You can be very focused, but if you're being too much of a perfectionist you're not being as productive as you could be.
This sounds like good advice -- but I am also trying to figure out why I still procrastinate hopelessly on projects that I do enjoy. Is it merely that I want/enjoy the "result" (feeling of accomplishment) more than the "process"? Namely I have just become lazy?. Or is some undiagnosed ADHD tripping me up at every step I take. I intend to meet a therapist soon and hope to find out. 40s is late but better than never I guess. Grew up in a country where mental health doesnt get any air time in daily life. Still figuring out whom to approach and how.
Ha well I'm 53 and I'm still trying to get better... There is a guy who presents on LinkedIn learning called Dave Crenshaw. He has a lot of good techniques and claims he developed them to conquer his ADHD.
Thanks. Luckily I have LinkedIn Learning through my employer subscription. Found his time management courses, bookmarked, and started one.
Words like "intend" and "soon" are your enemies. How about you do it right now? At least set a deadline in your calendar to do it. However, chances are it won't have the desired effect. One great method of dealing with a task is to delegate it to another person. Maybe ask someone to remind you that you need to see a therapist?
Thanks -- you have a good point.

Next time I look at my HN threads, I should have already set the first appointment.

One thing that helped me was to realise that procrastination is usually fear or apprehension.

Chunking tasks and reducing project start time helped.

Indeed.

Like many people say, starting something is half the battle.

For example I am currently postponing for days, a 5 minute phone call that I am supposed to make to a colleague. Not even big stakes -- just a new topic i am supposed to initiate work on. There is a negative outcome possible -- blame on me for slacking -- if I don't do this. Still I am struggling to make myself pickup the phone and make that call.

Rest of my duties as a professional and as a family member seem to be going one fine while this item keeps getting kicked down the road. 2 days and counting. I don't have any clue why.

That aside, Microsoft TODO which I think is based off wunderlist IIRC is fantastic. It has the features you need to manage a complex todo list but not an iota more and the iOS app is snappy. You can store your deadlines in there.

Having a todo with sub steps, deadline and planned date is great.

I agree but also I don't. Deadlines, and their close cousin goals, are but an excuse to stop working.

You either hit the deadline well in advance, in which case you can sit on your hands and still consider it a victory. Or you miss the deadline and you have failed and might as well give up. Or -- the worst case -- you can tell far in advance that you will miss so you don't even bother.

Compounding the problem is that we often aren't even in full control of what can make or break the deadline, so it becomes a lottery that, whatever the outcome, awards us with an excuse to stop working.

It's valuable to know the cost of time, though. There ought to be better technologies for this than deadlines.

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I've tried to think of ways to quantify this but not arrived at anything useful. The best method I know is to explain to an expert that "I didn't ship today because the product is still missing X which is necessary for the customer because Y", and then the expert can tell you off if you're wrong.

In fact, you might get far even when striking out the expert. An "I didn't ship today because" journal might be useful on its own.

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In contrast to other comments here, I don't think this is really about people needing different sorts of motivation, but more about excplicating the cost structure of the trade-off people make when they trade time (delay shipping) for... something else. This is a hidden cost which I believe frequently is larger than people think.

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And of course, time itself is an abstraction here for the benefits one get from shipping earlier, like faster feedback, less variability in release size, etc.

The alternative to deadlines is consistency. Do something every day, mark it off on the calendar, if you do it for 6 to 12 weeks, it's a permanent habit, move on to the next habit you want to form.
Isn't that just a recurring deadline at midnight? You still have that binary nature, except on a smaller scale.

I think you're onto something, though: in order to get an effect, we need to drill down to the daily, ongoing practises. We can't do it at a zoomed out, results-level view.

A habit is something you’ve done so often that you don’t need to think about it. Your brain can shut down into zombie mode and it’ll still happen. This is different from a deadline at midnight which is about ramping up stress to get your brain into a hyper-aware mode, opposite of zombie mode!
Absolutely. The idea is to eliminate the effort entirely - you really want to start extremely tiny, with the smallest step, and build on that.
No, typically it's not at midnight, it's more situational - when I do X, I also do Y. For example, check the oven is empty before you turn it on, water the plants every time you refill the cat's water, do a stretch every time you walk to the fridge, unload the dishes while you make your coffee, etc.
So is it "every day" or not? If it is "every day" how do you decide that you have missed a day?
If I did X, but I did not successfully do Y. Every once in a while missing is not a huge deal, but if you see consistent issues with performance it's time to try something else or choose a smaller habit to start with and work your way up. It's often at a greater frequency than a day, I just think it's easier to track if at the end of the day you make one checkmark.
No, a "recurring deadline" means that on the classic project management tradeoff of scope-time-resources(+quality?) you consider that a fixed scope MUST be delivered by a fixed deadline, and any variation means that you may (have to) spend more effort or dump quality to achieve that; but a "recurring habit" is an approach that you devote a certain systematic amount of effort+quality by the deadline but expect some variation in how much results will be achieved that.
I worked that worked for me. Tried to form habits for years like the neurotypical I'm not
I don't see it this way at all. The PM sorts tasks based on prerequisites and availability of resources needed to complete them. Deadlines are the times a task has to be done by to not block other tasks that have it as a prerequisite. If you achieve it well in advance, you note to bring it up in a performance review and pick a new task. If it's behind, you don't give up, people are waiting on you now.
You have a far more nuanced view of deadlines than most people I've spoken to. It sounds like you think of deadlines as a cost function where the cost of something not being done is zero until a particular date, then rises more and more as more time passes beyond that date.

That's a much more useful perspective than "it doesn't matter if it's done and suddenly on this day it becomes super important" which is what a deadline implies to me. (For concrete examples of this binary type of deadline, think of releasing something at a conference, or handing in an essay in school.)

That's a fair point, I definitely think closer to the second paragraph in terms of presentations etc. Different analysis than project work for sure.
I couldn't disagree more:

> You either hit the deadline well in advance, in which case you can sit on your hands and still consider it a victory.

Why would you sit on your hands? You feel tremendously satisfied that something was easier than expected, and look forward to moving onto the next thing earlier than expected.

> Or you miss the deadline and you have failed and might as well give up.

No, it's not failure at all. A thousand times no. You just realize you were too optimistic with your deadline, and you set a new one based on your new knowledge. Why would you give up?

> Or -- the worst case -- you can tell far in advance that you will miss so you don't even bother.

Again, just set a new deadline! Except in this case it might be too far out and you already discovered you were bad at estimating it, so break the task into a few chunks and just set a deadline for the first one.

At the end of the day, deadlines as motivation do work for some people, because instead of a task feeling scarily too-big that you don't know when you'll ever finish it, it encourages you to break it down, and compare your progress each day with what you expected to get done, because you now have a measurement stick. It turns things from unmanageable/scary/anxious into manageable/"I can do this"/confident. And you can (and should) reset the deadline if/when you learn that the task is much larger than expected.

The point isn't to meet the deadline or else you're a human failure, a million times no. It's just a tool to set a realistic goal and measure progress against something.

And realistically, you'll probably only make 50-70% of your internal deadlines like these, and that's the sweet spot. If you're hitting 95% of deadlines, they're too lax/easy to really motivate you. While if you're hitting 5% of them, they're way too strict/optimistic. The point is to be a healthy challenge.

Also to be clear, the article (and my comments) are about internal deadlines for motivation, not external deadlines at work.

I we are arguing the meaning of the word deadline at this point.

According to my dictionary, it's not really a deadline if you can just move it as soon as it seems inconvenient or out of reach.

I think maybe Lucas Costa calls those things preemption points. It's a time decided in advance against which you check your progress and assumptions, but with no connotations that work must be complete by that point, which is strongly implied calling it a deadline.

>But before you do, set a deadline. That’s the one piece of “technology” that’ll really help you ship. It’s a wonderful constraint.

Self-imposed deadlines as a mental hack can work for some people.

For some others, it doesn't work because their brain knows it's an "artificial deadline" created by their own mind. It's like trying to tickle oneself. The self-imposed deadline just comes and goes.

That said, there's no harm in trying it to see if you're one the ones it does work for.

There's a related piece of advice that goes something like: "Make your goals public, this way you're accountable to others who've heard you make a commitment to yourself and will be interested to see whether you achieve it."

Of course you have to pick the right people. Just tweeting it (at least if you're me) is the equivalent of telling no one.

Hell, even work deadlines don't work for me because I know they're made up and irrelevant. The only thing missing it is going to do is throw off someone else's bonus. Meeting it probably means I worked for free at some point as a salaried employee.
I think this is what drives some of the motivation for Agile-ish scheduling strategies.

1 week or 2 week sprint creates a deadline. Then you see if you planned too much or too little, and can adjust for the next sprint. And focuses you on just what you should be working on.

Even stand ups are little mini-deadlines. You kind of want to feel like you have something to report the following morning, based on what you said you were going to work on that day.

I find those things help me organize my thoughts and stay focused. And creates shared goals and expectations, and a little bit of social pressure (in a good way).

I understand others don't necessarily find them helpful.

I think this is a common but ultimately incorrect interpretation of scrum, which leads to unnecessary pressure, stress, and corner-cutting. Standup is for coordination and sprints are to avoid committing too much time before validating.

But if thinking of it as deadlines helps you, all the more power to you!

Low stakes deadlines, in my mind.
it depends on the your personality and your job.

For me, personally, deadlines never worked.

Probably it has something to do that I am somewhat like a rebel, and I oppose firmly any authoritarian order, even if it is my own.

Maybe it is because I have always done innovative work that never repeats itself. We program machines so they are the ones that repeat the work after it is done once. So I can not do what most people do: They know how much time something will take as they have done it a million times before.

Basically the best technology I use for me and my team is habits and knowledge about psychology(thing like anxiety and procrastination). Nothing beats that.

Surely the author meant TECHNIQUE, not "technology"?

Sticking to the actual topic, I'm not sure if it's really as good as the author wants to make it sound. Deadlines work great for some people, and for some they're just terrible, sometimes even counterproductive. To me artificial deadlines come off as a not particularly efficient tool.

Proscatination is the real issue, not deadlines.

People without procastination (or the ones who knows how to resolve procastination) won't need deadlines.

It's not an issue that you have no deadlines but you still do it. It's fine.

But if you delaying action you wanna do, you're missing many chances to fail.

Procrastination happens when people are not excited about completing a task. A deadline is a way of introducing excitement. Procrastination can be defined as “delaying working on a task until the impeding doom of the deadline grows too large.”
Procrastination may happen for dozens of reasons, emotions are are just part of it. Many people are excited about their projects and goals, yet they procrastinate on them (I'm one of those people).
Deadlines are a tool to increase stress. Some people respond to that stress by focusing on the work so deadlines are a very important tool for them. For everyone though, constant and persistent stress in not healthy long-term. Use it carefully, responsibly and in moderation!
I think the main problem I've faced is NOT KNOWING how much time to allocate for different tasks.

Sure, you can learn from past experience (e.g., "last time I needed to write a report like this, it took me a week"). But that means your brain must keep a memory of events+ellapsed_time, which is something my lazy brain avoids at all costs.

"Deadlines are huge, but really what are deadlines? They’re opportunities to fail. That’s all they are. They’re actually opportunities to learn, to fail. Hopefully not fail catastrophically, but it’s an incredible data gathering moment."

Brilliant. Will use this argument with my team. I'm not even joking :)

the thing that frustrates me about deadlines in many software organizations is that management seems intent on letting them slide by without comment. thus throwing away any opportunity think or talk about how well we are functioning as an organization, or even how well we are doing at setting schedules.
He writes about all these productivity tools and that he stopped using them. For me the same, but the one I still use and helps me is org mode. It excels at customizability and simplicity. How I use it: I write down my plan for the day, and I clock in and clock out, keep track on how much time I spend on actual work and doing useless stuff (like browsing the internet). When I saw how much time of the day you are actually doing nothing during time you have decided for your self to be productive, well that was a shock.
is it same Paul Ford as in this piece?

www.bloomberg.com/graphics/2015-paul-ford-what-is-code/

Deadlines always annoyed me. I suspect a large part of it is "what does it mean to miss a deadline?"

Oxford Languages: the latest time or date by which something _should_ be completed.

Meriam Webster: a date or time before which something must be done

Those have vastly different implications: If something _must_ be done it implies "missing this has negative consequences" whereas if something _should_ be done: it's possible there are no consequences.

Given that distinction: The author appears to share Oxford's definition. I'd rather differentiate these two definitions with different words "target date" vs "deadline". Missed deadlines are bad. Missed target require re-estimation of new target-dates.

managing emotions is at the crux of all of this. those productivity apps try to remove the emotion from certain decisions and give you some organizational help so you can act procedurally throughout your day. giving yourself a deadline is another approach coming that tries to focus the emotions you already feel into a productive force. a deadline will provide clarity because your subconscious will try to prioritize it over the small details that those productivity apps will have you continuously document, which can be a pain and sometimes create more friction when you're stuck with zero momentum.

if your life is already moving fast and you are managing a ton of different things, I think those productivity apps will provide a great resource to remind you of other things that need to get done and remove the friction that comes with context switching.

I disagree. There are some tools that really help by taking friction out of the way. A well-tuned text editor and a few good bash aliases can keep you focused on your task. Good tools are digital mise en place [1].

The problem is that these productivity tools can become tools for procrastination. You get to feel productive without actually doing anything. An out-of-control todo list or backlog becomes a wishlist.

1. https://nicolasbouliane.com/blog/mise-en-place

There are two kinds of deadlines: yours, and someone else's.

The two could not be more different.