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Deep Habits: Process Trumps Results for Daily Planning


The Planning Pitfall

Daily plans are tricky.

As I’ve long maintained, if you don’t give your time a job, it will dissipate in a fog of distracted tinkering. Simply having a to-do list isn’t enough: you need to provide the executive center of your brain a more detailed target to lock onto.

There is, however, a pitfall with this productivity strategy that I stumble into time and again: it’s easy to start associating “success” for your day with accomplishing your plan exactly as first envisioned, and to label any other outcome as a “failure” — a belief that triggers near constant frustration for most jobs.

The reality of daily scale productivity is that plans are not meant to be preserved. They’re instead meant as a device for ensuring that you tackle your day with deliberation.

Of course your carefully partitioned time blocks will be disrupted (how can you possibly predict the many ways in which your schedule might fall apart in the Age of E-mail?).

After such disruptions, you simply need to form a new plan for the time that remains — preserving your deliberative mindset. But it’s easy to cling to the idea that your original plan was somehow the best possible way for your day to unfold.

When I catch myself falling into this trap and despairing how far I’ve veered from some pristine but ultimately impossible ideal for my day, I’ve found it helpful to remember a simple heuristic: judge your day on how well your executed your productivity process, not the details of what you actually produced.

48 thoughts on “Deep Habits: Process Trumps Results for Daily Planning”

  1. Cal,

    I think the problem with daily plans is that you may lose the long-term view. I would say that the best strategy for producing the best out of your time, will be to do week plans with specific goals for each week and then adjust your days to fit that goals.
    What are your thoughts about this?

  2. Cal,

    Nice post! I’m a little confused about the last sentence: “{J}udge your day on how well your executed your productivity process, not the details of what you actually produced” – does this mean that I should be judging my day by whether I actually accomplish my goals for that day regardless of how I apportioned my time and blocked it off at the start of the day? Or is “productivity process” referring to something else other than my goals for the day?

    I apologize if this is a stupid question.

    • “process” to me here means that you were in control of your time, were able to go deep for deep work and act efficiently with shallow work, to not allow things to slip away into unplanned diversions, etc. If this is true, then it’s a good day, regardless of whether or not some things took much longer than you originally guessed, or if you were interrupted, etc.

  3. I also find myself frustrated when I get off my plan just in the middle of the day! That’s a great idea to replan your day when it gets disrupted, and don’t feel bad about it!
    Focus on your goals and the productivity process more than just following a plan that will surely change!

  4. Wait a minute….’judge your day on how well your executed your productivity process, not the details of what you actually produced.’ You’ve lost me: isn’t the goal to work toward the outcome? Why wouldn’t I judge based on outcome because the outcome gives feedback on the effectiveness of the process? Ultimate feedback loop, surely?

    • Outcome is important at the larger scale. But when you’re looking at a single day, you shouldn’t judge it as a failure if something took longer than you guessed, or if you were interrupted by something out of your control. What’s important is that you are executing productively, going deep when tackling deep work, acting efficiently with shallow, not allow unnecessary diversion, etc.

      • Cal –

        I’d still like you to elaborate more on this idea — “What’s important is that you are executing productively, going deep when tackling deep work, acting efficiently with shallow, not allow unnecessary diversion, etc.”

        How do you 1. measure and 2. take note “that you are executing productively, going deep when tackling deep work, acting efficiently with shallow, not allow unnecessary diversion, etc.” ?

        It seems like a powerful idea, but how to actually act on it?


  5. Cal,

    You articulate so well what many of us knowledge-workers feel on a daily basis but lack the clarity to express.

    This post is sooo true….especially for those of us with OCD about following our plan.

    You could write a book around this idea – judge yourself on how you followed your process – including the process of what you do when interruptions (or a sudden onset of lack of motivation/energy) strike – which usually happens every day at least a few times (for me anyways).

    How many life-changing posts can you have in a month?….geez.

  6. Very interesting post (along with your previous post on this topic). Years ago I found to-do lists massively helpful, so if you’re experience has been that this is far more useful, that’s very tempting.

    I’ll give this a try! Thanks!

    • Minor pedantry: Eisenhower attributes the quote to an old saying in the armed forces; the quote is typically attributed to him.

  7. Cal, I know you have covered the topic of your day planning before. But I am still intrigued by your relatively short work day. Being forced myself to work shorter days (= being a parent) I would be glad to hear you reflect some more on the relation between deep work and time spent working.

    (I have become much less stressed over this since I started to think of my long days, when I don’t leave for kindergarten at 15:00, as bonus time… “Hurray, I can work until 17:00!”)

  8. I’ve been trying to figure out how to do both short-term and long-term planning. I have to have things visible, not in a folder in my computer. I’ve been using whiteboards at home and at work recently, and I’m starting to get comfortable with it. I like how easy it is to erase and add/subtract. I’m thinking of keeping my medium/long term items in a list and then breaking them down into daily tasks and tagging them with a time to work on them, and then adjusting as needed. For example:

    On left side: Sepsis Dashboard – 8/21
    On right side: build variables into dashboard: 9 AM – 11 AM
    Design layout of dashboard: 11 AM – 12:30 PM

    etc etc

    Otherwise I get daunted by how to start on my big projects, and if it’s all little things I lose track of my trajectory/deadlines. It may not be a perfect system, but so far it clicks with me.

    • I’ve read the advice of some business coaches (take big pinch of salt now) who teach that most long-term goals/plans beyond 3-months are a waste of time to make and think about. Obviously there are exceptions (i.e. committing to a 4-year college degree, committing to a marriage, etc.).

      I like the concept of rarely trying to make goals/plans more than 3-months out – it is less stressful/more realistic.

  9. I am so glad that you talk about this. There’s a very thin line between being someone who is rigid and obsessed about a made-up rule and somebody who is flexible and sees these plans as guidelines. Utilizing our own wisdom and understanding of a particular context helps in not going overboard with this.

    Having said that, I think a lot of self-help writing about organization, planning etc has a certain way of phrasing their advice such that a normal human being’s only (worthwhile) goal in life is productivity. While in real life, we juggle different goals (and roles), and being productive is only one part of a host of strategies that we must continually adapt.

    At the risk of making this longer- I argue that an equally worthwhile goal might be the management of emotions- especially the kind that want to realize these ‘pristine’ ideal plans. That, alongwith a healthy dose of realistic expectations will result in a lot less self-flagellation.

  10. This reminds of Frog and Toad Together and the story entitled A List. Toad is intent on his list throughout the day so much it can paralyze him. Frog doesn’t have a list and goes chasing after the needs of the moment. We do better with a balance of both.

  11. Well I agree to some extent- but being productive at work is not a goal in and of itself. At work, we can also get satisfaction from other things-helping others for instance, or talking to a colleague. Nobody wants to waste time doing such things for long stretches, or *all* the time. But work is not this lone struggle between you and a task list either–it is ultimately a sum of how you handle it all-deep work, shallow work and the people with whom you work.

  12. Great post Cal.

    Focus and flexibility can work together effectively. And in some work those two things have to work in tandem. One thing I find helpful to ensure flexibility doesn’t become distraction is to stay mindful of my core work and core values. The day may go “off-script” but I’m still making progress in the work and/or quality of life.

  13. Hi Cal, many thanks for the posted insight. In fact I truly agree on your daily planning and replanning concept in which I managed to practice it extensively only recently after getting an iPad app named Calendars from Readdle. I feel now more in control of my day as I could intentionally dedicate my time for some tasks by creating an event entry in the app. Then as the dedicated time for the particular event has been spent on other things instead, I could just replan my day by dragging the task time slot to some other time. I would even say that the Calendars weekly view realises Stephen Covey’s weekly plan in electronics and interactive way and thus gives us a comprehensive view of our week planning.

    Additionally the task feature in the app (available as in-app purchases) which is based on Google Task is also very useful as it can appear together in the week view by setting its deadline. That way we can also incorporate the Most Important Things (MIT) concept into the calendar app.

    There are other apps that could possibly do the same or the other way to help us achieve better productivity but for me this Calendars app in my iPad has improved my productivity significantly in the way not found in other apps. 

    Anyway I’ve just started to blog about my discovery on IT tools for PhD research at While the content is still pretty not that much, I’d be soon adding more posts in the future and I’d welcome your visits and comments for the blog. Thank you.

  14. Cal – Great post. It made me think of the following blog post I read, which focuses on the importance of process in baseball. I think these principles apply broadly.
    From former big league catcher Brent Mayne’s blog from a few years ago:

    “Ubaldo Jimenez recently accomplished an amazing feat by throwing a no-hitter. While impressive, I find what happened the next day to be just as important and something all athletes might learn from.

    It had to be a really quick night after all the hoopla of pitching the Colorado Rockies first ever no-no … dealing with the media, answering emails, etc. And on top of that, the Rockies had a day game following that night game in Atlanta.

    But here’s where things get interesting. What does Ubaldo do on the morning after such a lofty accomplishment? He wakes up at 6:30 am and runs 6 miles through the streets of Atlanta. If ever a guy deserved to sleep in a little. This tells me Jimenez (like all the greats) is committed to “the process.”

    It’s been said many times before, baseball is a game of failure. It’s built into the game. If you base your enjoyment and self-worth on how well you do, you’re in for one hell of a roller coaster ride. And just like a roller coaster, it’s fun once, but riding one over and over again will make you flat out sick.

    Good players recognize and avoid this trap for the most part. They learn that lasting success and longevity come from trust in a process. In other words, they evaluate a day on how well they focused, did they get their work done, was their routine crisp. Not did they throw a no-hitter or get 4 hits. Results come and go but a good process lasts.

    Trust me, when it’s all said and done, I’m all about whether you got it done or not. It’s just that I recognize results are a by-product of a quality routine … not the other way around. Obviously, Jimenez (and Halladay, and Lincecum, and Mauer, and every other great player) recognize the same thing.

    Jimenez runs 6 miles the day after a start. Period. It’s part of his process. He doesn’t just do it after a win. He does it all the time. Then he probably plays long toss and lifts the next day, then a bullpen the next day, then something else the next day. And that leads him into his next start. So it’s all one big thing, it’s a week long or season long routine, not just a win or loss. And it’s not driven by results.”

    • Jeff –

      You quoted a blog — “Good players recognize and avoid this trap for the most part. They learn that lasting success and longevity come from trust in a process. In other words, they evaluate a day on how well they focused, did they get their work done, was their routine crisp.”

      I’d like you to say a bit more on how they measure these things and take note of them.

      How does one measure and take note of “how well I focused” or “was my routine crisp”?

      From experience, I’d say that in some things, for some time, one focused well, or that one’s routine was crisp, in some others, not so much, or not at all. But in any given work day, one probably goes through the whole spectrum of these anyway.

    • I’ll be sharing this article on my blog post about my productivity system. Any ideas on how to calculate productivity accurately? My current system certainly helps but I know it has it’s flaws.

  15. I love, love, love this!

    I am constantly having to coach people on the whole idea that weekly and daily plans are intentions, not ultimatums. This frees you from discouragement when things don’t go exactly as planned and encourages the proper level of forethought.

    I have an article with Harvard Business Review coming out soon where I framed success this way:

    “A perfect score should be defined as having confidence that you made the right decisions about how you invested your time based on the data you had in advance on potential tasks, your overall priorities, and the circumstances that arose throughout the day. The best way to evaluate the day is to ask yourself: Did I make the best choices in how I invested my time today? Instead of: Did I do everything as planned?”

    To your brilliance!
    Elizabeth Grace Saunders

  16. Elizabeth Grace –

    You said, “The best way to evaluate the day is to ask yourself: Did I make the best choices in how I invested my time today? ”

    So how does one do that?
    How does one measure whether one has made the best choices in how one has invested one’s time?
    And how does one take note of that?

    What you suggest seems like a powerful idea, but also one that easily turns into an ego trip, as one, in an effort to preserve a positive self-image, more or less subconsciously invents justifications for having used one’s time well. Eventually, this can spin out into, “I’m a wonderful person, everything I do is wonderful, I always make good use of my time.”

    IOW, without proper measuring methods and notation, evaluation can spin out of control and into plain old egomania.


    • Hi Sophia!

      Here’s an elaboration on the metrics used to determine if you made the best choices:

      1. Data you had in advance on potential tasks: This is where traditional planning comes in, meaning having a complete capture of potential tasks and firm commitments and making the best choices in light of that knowledge before starting the day.

      2. Your overall priorities: It’s important to also have a clear sense of your higher level work and life priorities. For example, you may know that a certain project is your highest priority at work so even if it takes longer than planned to complete a task for it, you invest the extra time and cut back on other work activities.

      3. Circumstances that arose throughout the day: These are the unpredictable, unexpected issues that come up, computer problems, personnel issues, etc. You don’t always need to change your plans for them but at times it can be legitimate to do so to make the highest use of the day.

      Hope that helps to clarify. Also, here’s a link to my latest post for Harvard Business Review that explains more:

      To your brilliance!
      Elizabeth Grace Saunders

  17. The daily planing is very important for our life and health both, but the problem part is that we don’t have any control over our mind and soul for some times. And the challenge is to overcome those challenge and try to do our daily practice in a proper way.

  18. As I was catching up on this blog, which I regularly follow, I couldn’t help but notice the outstanding question or two from Sophia. I obviously can’t speak on behalf of the esteemed writer, Elizabeth (Grace Saunders), whose writings I closely follow as well, in addition of course to Cal’s. But I’ll share my response, based on my understanding in particular of Elizabeth’s fine book entitled The 3 Secrets to Effective Time Investment: Achieve More Success with Less Stress.

    There’s a memorable passage in that book that I’ll now quote, and which I hope will in some way answer those questions. That passage leads off the following section in The 3 Secrets to Effective Time Investment:


    “Before we move on, let’s take a moment to quickly address a mental battle that many people face: They believe that if they don’t feel like doing something, that means that they don’t want to do something and therefore can’t do it.”

    “But that’s simply not the case.”

    “What you feel like is what you long to do based on physical sensations (e.g., fatigue, panic attack, or muscle tension) or emotions (e.g., sadness, love, fear, or anger). What you want to do is what not only will fulfill you in the moment but also will serve your highest priorities. You can develop routines that help you to do what you really want to do even if you don’t always feel like making the best choices in the moment.”

    I hope that helps…

    And this is for all readers: As I mentioned above, I’ve been closely following the writings of both Cal and Elizabeth over the years—it just so happens that I put together, during this past weekend, a set of vignettes of top thought leaders as a tribute to their overwhelmingly positive impact on the lives of readers like myself.

    Feel free to check it out @ Top Thought Leaders to Follow.

  19. I agree with your points,
    Its often hard to follow up with daily to-do lists especially when you’ve not mastered the act of goal setting.

    But i also believe that it will be easier to achieve your goals is you make them simple and easy enough.

    Also, having a weekly goals is important and once you set this, you just have to set up your daily goals in a way that will make achieving your weekly goals much easier.

  20. As a college student, I definitely value the idea of keeping a schedule and trying to stick to it. Having a set schedule is great, but it must be flexible. You never know when a professor may change the date of an assignment or a meeting gets moved to a different time. I try to plan out my days at the start of every week; however, my plan typically gets altered numerous times. By keeping that flexibility, you will not stress as much when the schedule gets changed. It is imperative to make sure that even though your schedule may change, you stay productive during your free time. In college, time is very valuable and needs to be utilized to the best of its ability. Overall, I think a schedule is important but flexibility needs to be maintained in order to have a successful college career.

  21. Thought followers of Study Hacks might be interested in the following from Seth Godin

    Seth’s Blog 31 August 2015

    Day traders rarely make history

    The short-term stuff is pretty easy to do well. Respond to incoming. Check it off your list. Next!

    The long-term stuff, on the other hand, is so easy to postpone, because tomorrow always sounds promising. And so we might hesitate to define the next project, or look for a new job, or visualize something that breaks what we’re already used to.

    Two thoughts:

    a. Keep them separate. The best way to avoid long-term work is to be exposed to juicy short-term urgencies.

    b. Hesitate before spending your most alert and dedicated work time on the short-term tasks.

    Day trading might be fun, but we can do better.

  22. Of course it is always good to have long-term goal/s. However, it is always a struggle on a daily basis to keep it at bay. There are by far many external forces that drag or push you. I believe that in order to achieve your goals, you need to know yourself and what you are capable of doing. Set short-term goals that match your personality. What works for you will work only for you. So don’t go looking for a generic system that seems to work for most people.

  23. Cal~

    I have often found myself basing my success or failure based off of how many check marks I am able to make on my to-do list at the end of the day. I truly enjoyed reading your article about how it is important to “judge your day on how well your executed your productivity process, not the details of what you actually produced.” Time is precious and it passes by whether you want it to or not. Being able to not only manage your time but to adjust it as it goes by. You can’t always take into account the curve balls life will throw you but you can me flexible and able to execute it after it has been thrown. Continue to focus on the process and results will come. When we get distracted by the results the focus isn’t on the process and that is when we become frustrated!


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