Study Hacks Blog

Deep Habits: Should You Track Hours or Milestones?

March 23rd, 2014 · 60 comments


Meaningful Metrics

Some of you have been requesting to hear more about my own struggles to live deeply in a distracted world. In this spirit, I want discuss strategies for completing important but non-urgent projects. In my experience, there are two useful things to track with respect to this type of work:

  1. Specific milestones: for example, the number of book chapters completed or mathematical results proved.
  2. Hours spent working deeply toward milestones: for example, you can keep a tally of the hours spent writing or working without distraction on an important proof.

In my own work life, I find myself oscillating between these two types of metrics somewhat erratically, and I’m not sure why.

A Hybrid Approach

Part of my confusion is that both approaches have pros and cons.

The advantage of tracking milestones, for example, is that the urge to achieve a clear outcome can inspire you to hustle; i.e., drop everything for a couple days and just hammer on the project until it gets where you need it to be. Sometimes my projects fall into a state of stasis where hustle of this type is needed to get unstuck.

The advantage of tracking hours, on the other hand, is that many of the important but non-urgent projects I pursue cannot be forced. I can commit, for example, to finishing a proof in a week, but this doesn’t mean I will succeed. Some proofs never come together;  some take months (or years); others fall quickly. It’s hard to predict. Tracking hours in this context ensures, at the very least, that these projects are getting a good share of my time, even if I can’t predict what will finish and when.

When it comes to productivity, I’m a big believer in simplicity. My oscillation between the different styles of methods described above strikes me as non-simple.

At the current moment, for example, I’m tracking deep hours on my key research projects (see the image above), but I also have a milestone plan for this work that seems to be almost completely useless. I think I maintain the latter because of an ill-defined sense that I need to add more hustle into the mix here.

When it comes to writing, I’m currently working on a big project (more on this later). I tried, but then quickly abandoned, an hour tracking approach to this work. Right now I’m having much more success hustling to hit carefully chosen milestones; probably because this work is more predictable.

I’m left, in other words, with a relatively confused jumble of approaches to keeping myself on track with big projects. I’m happy with the rate at which I’m producing, but I can’t help but wonder if: (1) I could be producing even more with my (well-defined and contained) working hours; or (2) if the scheduling and tracking of this production could be greatly simplified, and, in turn, simplify my life.

This is something I’m thinking a lot about recently. I’d be interested to know if you are too, and if so, what you’ve discovered works (or does not).

60 thoughts on “Deep Habits: Should You Track Hours or Milestones?

  1. Jeff says:

    So it kind of boils down to: track milestones until you’re having trouble delivering, then track hours. Or… track milestones until you’re having trouble delivering, and then adjust your milestones: perhaps the milestones can be broken up into pieces or different class of milestone.

    Often when I’m having trouble delivering, I need to think of the problem differently. “This proof is less of task and more of an exploration. What piece do I need to grok before I can explore more? That’s my next milestone. Or perhaps this is completely uncharted territory. I need to just say the next milestone is to figure out the next reasonable milestone.

  2. Corey says:

    I have experienced this before myself. I noticed when I was trying to make “Getting Things Done” to work that you could tell pretty quickly whether a task was “work” or “invention”. In that (long abandoned) process, I would either write “do this” or “brainstorm this”. I think the approach has to match the task, and I think we all can pretty quickly categorize these tasks.

    Anything that we have a lot of experience doing and which has few unknowns (like writing a research paper or taking data) responds to milestones and “deadlines”. We know writing a paper where the bulk of the discovery is already finished is something that will take a finite period of time and respond well to “get one section finished” or “get first raw draft typed”, etc.

    Anything that has a large number of unknowns responds best to “work hard for a few hours”. For me this is writing code, debugging, analyzing data, reading papers in my field, etc. If I set a deadline for something like this I procrastinate because I know I might never be done. I don’t want to start and risk being at the deadline with nothing done, feeling that nothing was even possible. Here is when I tell myself that I will definitely spend two hard hours on it, then I can stop. When I do so I accomplish much harder tasks more successfully.

    I believe just about anyone can write down which category a task is in, and that tells you which approach to take.

  3. I’m a big believer in tracking hours rather than milestones. That’s because I really want to avoid “hustling” whenever possible. The huge downside of hustling is that you may accomplish something worthwhile but you also risk burning yourself out. (After all, who can hustle every day or even every week/month?) If you put in the hours diligently enough, you will accomplish, eventually.

    As a writer, I want to train myself to be able to write every day, without drama. Recently, because of poor planning on my part, I had to hustle to finish a project. I wrote 9,000 words in four days for that one project while keeping up with all my other writing (at least 1,000 additional words per day.) It was HORRIBLE. I never want to go through that again.

    But everyone is different. Some people WANT that kind of drama in their lives. Not me. At least not anymore…

    1. Lila Stageberg, MD says:

      So very, very true! I have been in similar write-spin cycles doing course revisions and having to slam 3 days worth of work into one afternoon because the deadlines shift according to availability of the media people. I am deeply involved (and interested in) the lecture and lab courses in Anatomy and Physiology along with Pathophysiology that we run, and I find that my ideas, gleaned from extensive interaction with students, often lead to radical change in the design of the course but it takes me putting in a lot of time doing storyboards, etc. I have not tried the ‘tracking hours’ method because I am so very distractable. What do you do to allow yourself and structure the environment to allow the deep work on a task-directed focus that you describe?
      Loved your writing by the way!

    2. I find your comment very interesting, and telling. I think it was the specific reference of the milestone method as inviting drama.

      I, too, am a freelance writer and I work much better with milestones rather than hours. In fact, I may have been able to stay active in a corporate job if they had offered the option of milestone (or results) based work rather than being chained to a desk from 8am to 5:30 pm.

      I think the true key is that everyone needs to accept the type of flow and style that works best for them. And, in my case, working towards a milestone does not invite drama. In fact, my life since 2012 has been far less dramatic than my life before it where I worked tracking my hours in a corporate environment. There is no one right way to be successful.

  4. Dave Small says:

    Thanks for inviting us into the conversation Cal.

    Simplicity is not so much about finding one tool, but rather using the right tool for the task at hand (economy of effort). “Milestones” and “Hours spent” are tools — like a hammer or drill. The task at hand will dictate which one to use.

  5. Andrew says:

    I track hours because, like you said, research isn’t very well defined and you can spend a lot of time trying to answer an ill-posed question.

  6. Mark Miller says:

    It seems to me that the proper method of tracking depends the type of work. You gave examples of two types of work: mathematical proofs and writing a book. In writing a book, there is a relatively linear relationship between effort and production: three hours writing on a Sunday will be about as productive as three hours on a Wednesday. To me, tracking milestones is good for those types of tasks: the tangible, meaningful goal is easier to focus on than an arbitrary page or hour limit, and it gives a more meaningful measure of productivity.

    However, with tasks where output can vary wildly with effort, I find it’s best to measure in specific chunks, like hours spent on a proof. A day with little progress to show for does not necessarily mean you were distracted, lazy, or stupid, but that it was simply an unluckly day. And so the metric used accurately reflects that even though there is little to show for it, you made progress and did almost all you could toward the task.

  7. John W says:

    I avoid tracking hours. I find the task itself to be taxing, and it inevitably results in me being more focused on the time, and hours spent, than on fully understanding the material I am studying. I also believe time tracking can give people a false sense of security and satisfaction when they reflect on the hours spent.

    I would describe myself as utilizing a relaxed specific milestone strategy for important non-urgent projects.

  8. André F. says:

    Tracking milestones is much trickier and time consuming than just tracking hours. This is because:

    You have to spend time defining which milestones to accomplish, and during what period of time you’re supposed to complete, and what importance to give each of them (so that there is an order of preference).
    Then to define the period of time to complete a task in is reaaaaaly hard. It’s very unpredictable how much time one will use to complete a certain task, specially when talking about learning / studying, and to impose one either can make us rush to accomplish that deadline we set, or just relax too much. Of course you could, when adding a deadline specificy a tolerance 10th March +- 2 days, but it still makes it hard to manage your time. If you finish ahead of time, should you keep working on the next item? In my experience that doesn’t work great because you start feeling as if there’s no end to what you have to do each day.
    Also it’s very time consuming to make plans for each day, and for each week. Also unpredictable things happen weekly which change everything, and the daily / weekly plan has to be changed goes or worse to garbage and more time has to be spent on making a new one.

    Tracking hours doesn’t have any of those incoveniences. You just make a daily schedule. When unpredictable things happen, you can either just keep following it as if nothing happen, or devote the hours lost, spread out throughout the next days. You don’t risk burning out, because you made a schedule to avoid that. Simple as that.
    I’m open to hear better ideas to make it easier and better to tracking milestones though, if there are any.

    1. Barry Liden says:

      I like your point. I think your approach has the benefit of avoiding the potential for more distraction. I could see myself using the definition of milestones as a way to procrastinate and distract myself.

  9. Anna says:

    Your analysis has brought you to the brink of the correct conclusion, but you’re still holding back from recognizing it: different situations; different methods. Take the plunge, man. Use discrimination, then act. And don’t use too many words.

  10. Blake says:

    Like Daphne and Andre, I track hours although I try not to be too rigid about hitting a certain hour target because I know that not all hours are created equal. For instance, a few months back, I would jump right into my writing time eager to hit my hour goal and then find my mind wandering after thirty minutes because I forgot to respond to an email I needed to take care of. Taking a few minutes before beginning focused work to make sure all little details are taken care of is well worth the focused time “lost.”

  11. Tjerk says:

    I divide my “deep time” into two subcategories: “exploration” and “delivery”. For exploration, I just plan and record the hours spent. For delivery, I have specific day-to-day and week-to-week goals, but after working on the task (and hopefully/normally checking off the goal) I add the hours spent (in a different color) to my total tally. As such, I can keep track of whether the balance between exploration and delivery is apt for my overall goals. (Before I recorded it in this way, I usually spent too much time on delivery and too less on exploration).

  12. Taylor says:

    I am currently studying for the MCAT and maintaining a regular writing routine. I’ve tried these two methods on both, and here’s what I’ve concluded.

    1. MCAT: By nature, abstract academic work is more about inputs than outputs – synthesizing disparate systems and ideas. This requires time for rumination (even subconsciously) over time. So, best served by hourly scheduling.
    2. WRITING: This, on the other hand, is more about output work: sheer volume, revision, re-writing, etc. Mass output is motivated by hard, looming deadlines, because it’s more in your control. So, best served by milestones.

    To put arbitrary numbers on how I prioritize these methods:
    – Abstract work – 75% hourly, 25% milestones.
    – Output work – 75% milestones, 25% hourly.

  13. Hi Cal,

    As an academic, I’m primarily a writer, but I teach and run a business as well (as you know), so I use a combination of these methods. When I’m writing, I mostly track hours (minutes, really), but when I’m drafting and it’s important to turn out a lot of words, I track words (which would be the equivalent of milestones) and sections (get through x sections today, etc.).

    My student support business allows the students to track both ways: they track minutes in “deep” and “shallow” work and they track specific tasks (did they try out a specific “positive learning strategy” on that particular day).

  14. Carl says:

    Let me put in a pitch for no tracking. Nothing kills my creativity like thinking about the clock. Time disappears when I’m in a true flow state.

    If I were to track anything for creative work, it would be the size of the pile of scribbles. This is a very right-brain sort of tracking. Take pictures if you want to record documentation.

    1. AS says:

      I also don’t track. I work when I have the will and rest when I don’t. Following natural rythyms let’s me jointly maximize my output and happiness.

      Sometimes I do have a specific goal in mind, such as “finish homework problem #9 today.” I will work until I either finish or run out of energy.

  15. Sam says:

    I have been doing project management for the past few years and I do like the hybrid approach in that Milestones are kind of like the vision. It keeps you focused on the end-goal and what you’re trying to achieve. The hours is how you’re going to get there and the steps between where you are and where you want to be.

    To put it into different terms, the milestone is the why, the hours are the how.

    1. Jean Vaux says:

      Or lag/why and lead/how.

  16. Bill says:

    I’ve been working on this idea for a couple of years now. I concur that it’s not a simple problem — but I stumbled across an analogy that seems to help me: the potter’s wheel.

    I had occasion to watch a group of potters at work for an extended period of time. It became obvious that a good potter is seamlessly and constantly shifting mental gears. They slide back and forth between deep and shallow work, while simultaneously oscillating between specific objectives (like the lip of the pot) and a “let’s see where this goes” approach to the artistry. Watch their faces and hands, and you’ll see these two sets of behaviors are like totally independent waveforms, as if managed by two different people (or two different parts of the brain). It’s very hard to describe in a linear way.

    After watching for a long time, I started to visit other artist friends who work in different media, and noticed the same thing: A behavior pattern that looked like a complex waveform, with the phase of each component wave being controlled by the evolving work. It’s easier to notice with potters and glassblowers, I discovered, because both arts have some inherent urgency built into the process.

    Then I tried this with a furniture maker and a custom brick-mason, and noticed something funny. Craftsmen tend to linearize the waveforms: shallow, milestone-driven work first, until everything but the more artistic pieces are done; then a sudden conversion to deeper and more speculative work; then back to shallow *but* non-milestone-driven work to cap off the piece.

    So far, all I’ve been able to realize is that there’s a serious nuance that separates the craftsman mindset from the *artisan* mindset, and it has to do with the (learned or instinctive?) ability to float seamlessly back and forth between combinations of deep/shallow and milestone/speculative work. No theory yet. Hope this is relevant to what you’re doing.

    1. Lila Stageberg, MD says:

      What a gorgeously put concept! I totally loved the idea you put forth and it was beautifully explained! I am an art quilter in my spare time and I find that it is exactly as you say – a constant shifting from creativity and sort of flow work back to ‘Oops, the needle is stuck or the bobbin ran out of thread!” and I have to snap back to Technician to deal with that. My son was watching me quilt one day and he said ‘you know, most of what you are doing is dealing with errors. Things that would stop someone else just let you show how you know how to fix any obstacle you run into.’ I was impressed with his grasp of the work.
      I also find that I yearn to get to my sewing machine when I have spent a lot of time on my ‘day job’ of teaching Anatomy and Physiology online. The linear tasks I accomplish make me feel sort of restricted and stuck, and I get wanting to go do something where I make ALL the decisions and can control the project with my heart.

    2. jean an says:

      Thank you Bill, for the insightful metaphor of the potter’s wheel. This is a reference point I can relate to as I recollect my observations of the glass-blower at Corning Museum of Glass and the snuff bottle painter in Beijing.

      Alas, some projects, especially those done with company, won’t delineate our time as apparently as that of the artisan and craftsman unless we force ourselves to keep track. Like you, I’ve no theory yet as for how the seamless float is so, seamless.

      Perhaps time will tell. Thankfully, in any profession there’re hacks to switch between the artisan and craftsman. A writer can choose to put a ‘#’ after a phrase that he isn’t exactly satisfied with, and return to it later (learnt from Daphne Grey-Grant). This allows flow yet permits tweaks.

      From my experience, I found that keeping track of ‘time accrued’ per task helps me plan time allocated for future tasks of a similar vein. After reading this post, I would add an additional ‘skills used’ or ‘tabs benchmarked’ so as to better predict output.

      Thank you Cal for creating this environment for sharing our hacks.

  17. Michael Weber says:

    What works for me is to plan out my week with hours I hope to devote to projects that matter and with particular milestones I hope to achieve in that week. I weigh the value of these milestones using a somewhat arbitrary point system and also assign points to the hours worked. As long as I am somewhat consistent in my methodology, I have a fairly reliable record of my relative output from week to week. I have been using this system for several years now and have refined it to a point where it is useful to me to analyze my results and thereby spot reasons for favorable and unfavorable variances in my own productivity.

  18. Claudio Gomez says:

    (you analyzed the advantages only, not the disadvantages of each method)

    Hustle downsides: (i) when you are too obsessive about sth, it is easier for you to wrongly prioritize and leave important things behind; (ii) you may get burned out; and (iii) your daily routine may easily lose balance, taking some time afterwards for one to recover and catch up.

    Hours downsides: (i) this approach may be insufficient when you have something really big, and the other activities in your daily routine may end up jeopardizing your project (leading to less motivation, or a potential need to hustle if it becomes urgent at some point in time); and (ii) you may lose track of your goal and the activity becomes and end in itself (which may be fine for meditation or daily exercises, but not for writing a book, for example).

    It seems clear that the bad outcomes of tracking milestones show up earlier in the timeline compared to the downsides of tracking hours. When you try tracking hours first, it may be far too late and regrettable when you discover that you should had tracked milestones instead.

    Though tracking milestones may be somehow taxing, you will find out earlier that it does not work and than change to tracking hours.

    So, I agree with the others that these are different tools for different situations. But if I am doubtful about which one to use, I would certainly always prioritize tracking milestones over hours. One would rapidly figure out that it does not work and then change to tracking hours (and I would probably keep reviewing it from time to time, to see if I am able to get back to tracking milestones in the near future).

  19. NewWorldOrder says:

    I think the notion of tracking milestones vs. time is a false dichotomy. I don’t see an issue with tracking both simultaneously. That said, I do think there’s a danger in looking only at time tracking. Just because you went to the gym for an hour doesn’t mean you had a good workout. I think focusing on time causes people to figure out ways to be less efficient. If you have to stay in the office 8 hours a day no matter what, you’re probably not going to be that motivated to find ways to make efficient use your time.

    1. Richard Huynh says:

      Definitely. I think one way time tracking could be used is in the initial formation of a new habit. With the example of working out, I might focus on getting from zero physical exercise to hitting the gym for at least 15 minutes daily for a week as the first goal. I could then start making exercise milestones once the issue of actually showing up becomes less of a struggle.

      1. Rob Duncan says:

        Richard, I think you hit upon a really cool idea! when creating a new habit, first track hours until the habit becomes automatic, then start tracking milestones.

  20. ko says:

    I find hours to be misleading and not a true representation of the work achieved. For example the classes I take state you should be doing a ration of 1 part class/2 parts own study and , others prescribe an idela number of hrs per week for their class.

    My experiences is I when I try to work for said number of hours, sometimes I could have done with more , or sometimes less. Which all brings it back to around to the issue of hard/deep work (well for me anyway). when I achieve the tasks I set out to do then my work is done.

    Which makes me want to ask, Cal, how do you determine if you have spent sufficient time on something if you are not basing your effort on time put in ?

  21. Cal, like you, I see pros and cons to both approaches. Yet I find myself coming back to milestones. If I’m not seeing results, there’s something wrong.

  22. Interesting analysis, and interesting comments above…

    I’m not in the business of doing mathematical proofs and my approach might not work for those (they could be a special edge case) but for all other tasks I find that tracking milestones is much more effective. And also more satisfying! Knowing that I’ve worked another 3 hours on project X is way less fulfilling than knowing I’ve enabled HTTPS.

    For some research projects or open ended tasks (learn a foreign language, teach my son to swim) milestones can be hard to come by. In my experience this doesn’t mean milestones are the wrong approach though, it just means I haven’t thought about them fully enough or in the right way.

    E.g. learning a foreign language – I can set a goal like “have a 5 minute conversation using Verbling” or “write my journal in Mandarin at least once a week for two months”. These milestones are artificial, but they help encourage me to put the time in that I need to and they are also concretely achievable. Plus they provide a real barometer of progress and motivate me to achieve more.

    In the same way, a big part of teaching my son to swim is not just spending time with him but helping him really enjoy it. By setting milestones – “go swimming somewhere new and different this week”, “find a new way of making swimming seem fun and interesting” – I make sure that I do spend the time (which is important) and also make the somewhat amorphous and imprecise goal of teaching him to swim more tangible. Because finding a new way of making swimming seem fun and interesting is just as amorphous, but it is also more achievable because it is smaller. That sort of disaggregation of big tasks which “need” hours tracking seems key to me. Maybe it could also be used for proofs?

  23. John says:


    You MUST SEE this TED talk. In this talk, Harvard Professor, Daniel Gilbert, talks about a experiment where subjects where asked to put 6 pictures of paintings in the order from which they like the most to the one they like the least. So that the paintings where ranked #1, #2 and so forth. After that the subjects were told that the scientist had an extra copy of the paintings they rated as #3 and #4. They asked the subjects which painting they wanted. As you might have expected they picked #3.

    A week later, the scientist brought the subjects back to the lab and asked again to put the pictures in the order of how much they like them. Here is the BIG surprise. The second time around, the people moved the #3 picture they previously picked a week ago to #2 spot.

    The scientist concluded that the more whatever we chose, we become invested in it, and invariability will GROW TO LIKE IT.

    This is in alignment with you “So Good They Can’t Ignore It” thesis that in essence says that passion has to GROWN, by developing a skill and doing the other things you outline in your book. This study shows that people CAN GROW to like what they pick and become INVESTED IN.

    Cal, I hope you will find this valuable. Here is the link if you are interested.

    It has over 8 million views 🙂

  24. A.I. says:


    this is the first time I comment on your blog – and I’ve stumbled over it only very recently.

    I can very much relate to your problem, and I’d go so far to claim that I’m facing identical problems.

    I think one must divide areas of action. There is no “one size fits all”.

    People judge you on the results you deliver – so one must take care of that.

    I’m implementing the following strategy. I have two kinds of time blocks, the results time blocks and the deep work time blocks. I always try to allocate the deep work time blocks to the periods when I’m cognitively fittest, which is between 9a.m. – 1.p.m, with variations. (Sometimes I’m not yet fit at 9, so it’s 10-1, and sometimes it’s 9-12).

    For results time blocks, I use a milestone approach. For the deep work time blocks, I use tracking hours. I’ve tried milestoning for the latter, but for me it simply doesn’t work at all, precisely for the reason you describe in your post: It’s simply impossible to know how long it’s going to take you when you’re venturing into unknown intellectual territory.

    Let’s say you are hiking (or jogging) into a forest and are curious about a new path you discovered. Not knowing where it leads to, you take it because you’re curious. You meander through the forest until you find a way back home. I did that a number of times, it’s fun (but only during summer, when it’s warm and there is more daylight available 🙂 )

    How are you going to plan when you’re going to be back home, or how long the hike will take you? It’s impossible.

    You mentioned yourself the example of musicians or chess players who devote a substantial time to deliberate practice. How would a piano player set a milestone, how would he define it?

    I’ve always been into sports and when I started playing tennis, I realized very quickly that playing doesn’t make you better, but systematically practicing shots of increasing difficulty does. So I tried to get as many practice hours as possible. Hence deliberate practice is a very natural concept for me. Even though I certainly didn’t become a new Roger Federer, I was soon able to beat players who have been playing tennis at a recreational level for much longer than me.

    If the work to be done is of a kind that the path to its completion is clear, then this is clearly a result oriented work and needs to be milestoned.

    I agree completely with you that a time management system needs to be as simple as humanly possible.

    But as my childhood hero Einstein has said: “A theory needs to be as simple as possible, but as complicated as necessary.” (Feynman became my adolescence hero 🙂 )

    I think Einstein was right on target there, and sometimes we need to take the complexities of our lives into account.

  25. A big break through for me is to identify all feelings as what I call “symptoms” For example, in the past, if I constantly got distracted when working on a big project, I would count it as weakness, laziness, lack of focus(this last one was true, the first two were judgments)
    and I would try harder and harder to force myself to stay on task. Sometimes I was able to push past it, and other times I just caused myself considerable turmoil without much successful production. Now, I pause, and evaluate the “lack of focus” – is it a symptom of something that I should be paying attention to? There could be a good reason why I am “stuck” – it could be physical, emotional, or relational. I don’t “judge” as much now- I pause, evaluate, and sometimes easily see what is causing the block. Other times I don’t see a solution to the impasse right away, but I stay more relaxed in the midst of the stress. Does that make sense? Anyway, I feel a lot better, and I accomplish more!

  26. Amund says:

    I have been planning and tracking my urgent and non-urgent tasks in three categories for some time: Idea work, production and administration. I find myself in different mental modes in each of them.
    Idea work includes sketching (I work as a graphic designer), reading, research etc., and I only set time goals here. This has a double benefit: it relieves the pressure of having to produce something specific – sometimes I will go home without a “result” and that’s OK. It also makes me focus on something and not procrastinate: if I get stuck I know I only will work on this for one more hour, then I’m done. What I find is that when working in this context a specific outcome goal will often emerge: a good idea has to be developed to a certain point, for instance, and I just work until I’m there.
    Production is measured by completed tasks. This means taking an idea to an outcome I can show to a customer, for instance. It is useful for actually reaching deadlines and working with a clear goal in mind. Sometimes this goes back to more open ended idea work before I get there, but it helps to have a clear goal in mind so I actually deliver – also on non-urgent but important projects.
    Administration is accounting, writing proposals, contracts etc. I set aside a day every now and then to get it out of the way. This means a combination of time and task: during one day, I will get all of these boring things done so I don’t have to think about them anymore.
    And thank you Cal! I have been reading your blog for a long time, and even though I don’t reply to your posts I find a whole lot of inspiration and insight in them.

  27. RQ says:


    I read your work with great interest. I’m curious whether you’ve been able to maintain your well-defined and contained work schedule as you’ve moved into a faculty position. I followed that approach as a graduate student but it has been increasingly less feasible as I’ve moved through the academic ranks.

  28. Nick says:

    I have started tracking both. I set milestones, and I keep an excel spreadsheet where I track both how much time I spend on it and whether I accomplished the milestone for the day.

    Somebody told me that this way, there is the added benefit that you get a feel for how much work you can do per unit time–and then you can push to increase that quantity.

    If it looks like you are spending lots of time and failing to meet milestones, you can adjust and set easier milestones. And if you are spending little time and meeting lots of milestones, clearly you need to push yourself more.

  29. Matt says:

    Part of the determining factor may be if you are a left brain (analytical) thinker i
    or right brain(creative type) thinker.
    Left brainers may tend towards the tracking hours approach. Time is measurable and tangible and goals can be reached with quantifiable criteria,
    Right brain types may use milestones based on their perception of when a milestone is completed.

  30. Yan Tang says:


    I would suggest to track hours as a daily routine and track milestones during weekly/monthly/yearly review. In my opinion, tracking milestones involves two steps: track how time is spent which is simple and track how time spent towards the milestones which involves thinking and organizing. The first step, tracking hours, is more like data collection while the second step could be viewed as data analysis. From this point of view, tracking milestones should be done as post process.

    I always use bubbletimer to track my time. During my periodic review, I then evaluate how my time contributes to milestones.

    That’s my two cents.

  31. Sachmo says:

    I use a kanban board to track major milestones. I leave it up in my room, and when I walk by it, it grounds me in the big picture (see Personal Kanban by Benson).

    I use sprint planning with points to estimate tasks to track time spent on stuff (See Getting Results the Agile Way – JD Meier, or any other Agile book actually).

    The sprint planning stuff helps me balance my week with the right amount of work I can actually get done. It forces me to think about all of the little stuff – like buying groceries, sending out that piece of mail, etc. – and tie them into my schedule. Items in the Kanban board will also be covered in my sprints and assigned points just like anything else. The Kanban board reminds me if I’m not hammering on the big projects the needle won’t move.

    It’s not perfect, but it works better than anything else I’ve tried so far.

    Blocking time does not work for me. Though if I really need to get things done in a crunch I’ll start counting pomodoros (See Pomodoro Technique).

  32. Study Hacks says:

    I’m processing all of these comments as well as some ideas that were sent to me via e-mail. I think I’m close to some conclusions. I might right a new post about what makes sense to me out of this discussion…

  33. FTIR says:

    Reading through this, it seems that you want to track the hours it takes to create a plan/milestone for a project.

    However, I always end up with the problem of procrastination that Cal wrote about years ago. I can’t do either until my brain accepts that the idea can go somewhere.

  34. Seems similar to the discussion betwern fixed-time and fixed-scope in Agile software development. The community has given up on defining both beforehand (No Estimates movement), once you fix one the other is a dependent variable.

  35. Bill H says:

    Here’s my approach which fuses or marries up several aspects of both time and milestone traffic.

    Have a work list of end results and a personal list of end results, so you don’t let bleed or diffusion occur across the two spaces.

    Here is a partial day’s list of items, for Work. I explain side notation beneath the list

    Build draft IP charts for talk. 2 BC
    Generate prioritized list of features for instrumentation work. 1 A
    Process email 1 D
    Lunch 2 K
    Review and comment on workflow diagrams sent by Kim 2 EF
    Break G
    Generate deeper comparison of Q1 vs Q2 results in web hits 3 HIJ

    So I don’t worry about the order or priority of the list when I write it down. Just get the list down on paper.

    Then I create a time allocation value for each task in terms of “units of UNINTERRUPTED 2O minutes” (could be any amount, perhaps increasing as you get better at pushing off distractions). That’s what the numbers mean next to each time…..that is the time I can should spend on that “desired outcome” today.

    Then here comes the sequencing and prioritizing. I then alphabetize the work items, beginning with A and then allocations Letters equivalent to the amount of time I can spend on each deliverable. If 40 minutes….then that item gets 2 letters.

    I force myself to do the distasteful tasks firsts…the ones I’d rather not do. I do this as a way of pushing my emotions to the “back seat” and putting my will and intellect in the front seat.

  36. Bill H says:

    Connection dropped first attempt. Could be a dupe.

    Here’s my approach which fuses or marries up several aspects of both time and milestone traffic.

    Have a work list of end results and a personal list of end results, so you don’t let bleed or diffusion occur across the two spaces.

    Here is a partial day’s list of items, for Work. I explain side notation beneath the list

    Build draft IP charts for talk. 2 BC
    Generate prioritized list of features for instrumentation work. 1 A
    Process email 1 D
    Lunch 2 K
    Review and comment on workflow diagrams sent by Kim 2 EF
    Break G
    Generate deeper comparison of Q1 vs Q2 results in web hits 3 HIJ

    So I don’t worry about the order or priority of the list when I write it down. Just get the list down on paper.

    Then I create a time allocation value for each task in terms of “units of UNINTERRUPTED 2O minutes” (could be any amount, perhaps increasing as you get better at pushing off distractions). That’s what the numbers mean next to each time…..that is the time I can should spend on that “desired outcome” today.

    Then here comes the sequencing and prioritizing. I then alphabetize the work items, beginning with A and then allocations Letters equivalent to the amount of time I can spend on each deliverable. If 40 minutes….then that item gets 2 letters.

    I force myself to do the distasteful tasks firsts…the ones I’d rather not do. I do this as a way of pushing my emotions to the “back seat” and putting my will and intellect in the front seat.

  37. Andrea says:

    Hey Cal,

    This sounds similar to the 2 approaches to working out – do you count reps or time?
    Do you run 5k or run for 30 min?

    The answer depends on what you want to achieve I think. If you’re training to complete a distance race, then you better dock in the miles. If you want to get fit then maybe you should clock in time. In reality, if you do the miles it will take time, and if you do the time then you’ll be covering some distance…

    The sports metaphor makes it more obvious that the two overlap, which may not solve your oscillation dilemma, but hopefully explains it from a different perspective. I’d say it’s fair to toggle between the two, and any more simplicity might strip you of the flexibility to adapt to different situations – as you say, use the pros and cons of each method as appropriate.

  38. That picture is different than I expected from the description on page 140 in Deep Work. Thanks for including this link in the book notes!

    I plan on employing this strategy during my sabbatical, neat idea.

  39. tushar says:

    hi, thank you for this post I agree with you that advantage of tracking hours, on the other hand, is that many of the important but non-urgent projects I pursue cannot be forced. very useful information

  40. Cassie says:

    I am about halfway through your book. As for this post, I think it depends on what you’re tracking. If, for a student or academic, tracking milestones is better, especially in making sure your daily homework is done. For fitness, tracking the hours you use to work out is better than a milestone (although, you could even do both, if you are also trying to lose weight or lift a certain amount of weight). Back to reading!

  41. Piero says:

    Hi Cal
    I believe we don’t have to pick one system or the other.
    Milestones are the output, hours are the input.
    We should track both when possible so that we can measure productivity and possibly use the results to forecast similar project duration.
    When the output is difficult to breakdown in milestones just focus on the input (hours)

  42. Simon says:

    I have been using an App to record my hours for one and half years. It’s very helpful. But I am sometimes confusing as well and asking myself: shall I stop it?

  43. shaushima says:

    OMG I got here via one of your book named Deep work

    Sir, your book is very useful for me and I’m proud to read a book from a great man like you

    Thank you for your time sir

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