Getting Things Done (Part 1) – Getting Concrete

Despite the many good things about a note card-based system of taking and organizing notes, there are occasional downsides. In this case, in going through my outline for this introductory series of posts, I skipped over the bridge between strategy and the more tactical issues we’ve begun discussing in Persuasion and will keep on with in Speaking Well and Writing Well. Specifically, in a busy life with many demands, how do you get the things done that actually matter? How do you take day to day steps to reach the strategic goals you’ve defined in accordance with your values? I don’t propose to give a comprehensive answer here, as I can tell you from prior experience that “productivity” as a field is its own immense rabbit hole you can fall down for quite a while (ironically enough, I suppose). Instead, having spent quite some time exploring those warrens, I’d like to share a handful of techniques that have stuck with me even as my main interests have shifted, especially those that are most effective at supporting the values-first, high-agency approach we aim to cultivate here.

The Weight of the Personal – Do What Works for You

First off, I want to touch on something that I see get lost in the productivity space far too often: people are actually very different, including when it comes to how they can get the most high-quality work done. Yes, most of the principles tend to be roughly the same between people, hence Stephen Covey’s Seven Habits of Highly Effective People, but what the actual day-to-day manifestation of those principles looks like can be very different. For example, there is a famous productivity system developed by David Allen called (wait for it) “Getting Things Done” or GTD. I read this at the height of my interest in productivity as a discipline, and at first I was like “yes, this is amazing, a complete, wholly worked-out system that will let me get on top of my life and do amazing things.” Well, I tried it for a bit, could never quite get the whole thing rolling as a system, and ended up dropping most of it, though keeping a few handy tools (like the rule of thumb that if you have an email you can “resolve” within two minutes, just do it right away, but if it’s going to take longer, save it for some dedicated time later). I now believe that the GTD system is perfect for David Allen, and likely very good for some number of people, merely okay for some of us, and might be actively unhelpful for some others.

All of which is to say, as we talk through ways of thinking about how to break our big picture goals into manageable work, and then how to do that work in the way that best helps us reach our goals and live our values, it’s helpful to remind ourselves that what works for me may not work for you, and it may take some time to figure that out, which is okay. Perhaps most importantly of all: if you have a way of doing things that works for you – you’re getting the results you want and you feel good about it, don’t let anyone tell you that you’re doing it wrong, or that you “should” do it some other way. On the other hand, if there are any areas of your life where you feel like you could be more “productive” or “effective” (though I am a bit reluctant to use the standard language of the productivity-as-self-help literature, as it gets uncomfortably close to the kind of systematizing, mechanizing approach to humans that this entire project is pushing against), then read on for a few ideas on what might work for you.

Breaking Down Big Goals into the Day to Day

We’ve already spent some time talking about taking our abstract values and turning them into more concrete goals, but so far these have been fairly big picture. It’s all well and good to have an idea for a business, a notion of whom your audience for it is, and the gist of what being successful in that endeavor might look like, but that still leaves you wondering “what do I do today, right now?” To get there, we have to roll up our sleeves and start thinking in a more grounded way. Sometimes, the immediate or intermediate steps you will need to take are obvious, or at least fairly so: I have a goal to increase the weight on my single rep max, so I need to spend more time lifting weights. Or I would like to become a better artist, so I’ll need to get some instruction and spend some time practicing. Or I’d like to publish a book, so I’m going to have to write it. These are all helpful (and true), but they lack a certain specificity. Especially when we pursue a new field of endeavor, or if not wholly new, one where we lack extensive experience, we run into obstacles at the granular, practical level. To take the weight-lifting example: how often should I go to the gym? How many sets of how many reps should I do? How important is my diet? What about other exercise not directly related to that goal? As you can see from just this handful of questions, when you try to take big, abstract ideas and turn them into the nitty-gritty of a daily routine, innumerable bumps, hurdles, and nuances present themselves.

Some Short Thoughts on Friction

A brief aside that I thought I had covered in strategy, but see on double-checking that I have not. In On War, Carl Von Clausewitz states that in war, everything you must do is very simple, but everything you must do is very hard. Imagine you’re in command of a regiment and you’re ordered to march your soldiers 1 mile to the west and take up position on top of the hill there within the next half hour. Simple, right? It’s a walk through the countryside with ~1,000 of your closest friends. On the other hand, what if it’s been raining for a week straight and the connecting road is now knee-deep mud? What if your soldiers just force-marched 25 miles through the night to get here, and when they got here, the supplies hadn’t arrived, and they still haven’t had a good meal? What if the hill itself is rocky and wooded? What if the enemy is already on top of it and starts shooting at you as you approach? Your simple task has become very hard.

Clausewitz called these things that make doing simple things actually hard friction, and it is one of my favorite concepts because it pops up all over the place. You try to leave plenty of time to drive to work, but there’s an accident that causes a worse-than-usual traffic jam. You order a gift with what should be plenty of time to arrive before Christmas, only for a blizzard to ground all flights. You sit down at your desk to focus on an assignment, only to get called into meeting after meeting. All of these are instances of Friction, and when it comes to getting things done, friction is what we have to overcome. And as we started to discuss above, when we are new to doing something, our own lack of experience is a big source of friction.

Getting Concrete to Understand What You Need to Do

So, if we want to learn a new skill or build a new habit or start a new way of working, we want to get concrete – what do we actually do moment to moment, and what does doing it well look like? For this, one of our biggest tools is one that we discussed in the opening post: mimesis. These days, it is easier than ever to find someone who has not only done what you’re trying to do for just about everything, but to find someone who has pursued it to an obsessive degree. Thus, our first step might be to look for books, blog posts, or videos about the new task we’re hoping to pursue. This can be tricky, and takes some discernment, for there are as many views on the best way to build a new skill as there are folks who have gotten any good at it, and when you add in the pressures to get attention and money from sharing these views, it can be quite hard to figure out which path through the woods is the best to take, or if you’d be better off whipping out the machete and hacking your own.

To work this out, there is a long, slow way, and a handful of shortcuts. In the long run, you are likely to make use of both shortcuts and the slower methods, but it’s helpful to recognize what they are, especially when you’re first getting started. The chief challenge when entering a new field is determining the credibility of the folks you might seek to imitate or get guidance from. The catch-22 here is that the only way to really determine someone’s credibility is to become an expert yourself and then evaluate them – but that’s not so helpful when you’re trying to figure out “who do I learn from in the first place?” So, the long way is to dip your toe in here and there, seek out different perspectives, different approaches, and to give them a try. See what works for you and what doesn’t, and over time, you’ll develop your own opinions and judgments on the field and how to approach it, and you’ll start to notice which teachers/influencers/big names resonate with you and which don’t. The downside to this approach is that if you follow it too diligently and don’t start experimenting, you’ll be putting off actually doing the things you want to do. The plus side is that whether you consciously pursue it as a strategy or not, you’ll be getting the experience and developing the opinions anyway.

To get started, then, there are a few shortcuts that can be helpful. The gold standard is the “warm introduction.” If you have someone that you know and trust who knows something about the field, ask him to point you to useful resources. Here, you are using your own judgment of the credibility of your acquaintance as a shortcut to evaluate the credibility of the sources he directs you to. Obviously, the better you know the person and the more you trust him, the more effective this technique is. If you want to get stronger and have a gym rat friend, you’re in good shape. On the other hand, if you want to write and publish a book and you don’t know anyone personally who’s done that, you’ll be relying on more distant means of familiarity – authors whose books you’ve liked, classes that are highly rated, or what have you. Combining this with the longer way around, once you find a source that your own experience validates, mine it for references and inspirations relentlessly. If you find a channel with videos on weight-lifting that’s given you good advice, listen for whom he mentions as also getting it right, pay attention to the terminology he uses and see if it pops up in certain schools of thought, and seek out interactive media where he appears (like podcasts or interviews) and see whom he’s willing to talk to. These links won’t be a “slam dunk” the way a recommendation from a trusted friend is, but are much better than exploring totally blindly.

The next shortcut is to weed out those sources likely to be unhelpful, to make your search-space smaller. Maybe you can’t figure out which of 10 potential gurus is great, but if you figure out that 6 of them are likely full of it, you’ll have a much easier time sorting through the remaining 4. Some red lights to look out for include overly an overly pushy/scammy approach (“to unlock extra gains, subscribe to the secret members channel!” “pay $99.99 for one weird trick to 10x your gains!”), “one-true-wayism,” by which I mean the insistence that his, and only his, preferred approach will work, and anything that promises quick, easy achievement of things that you know darn well take hard work and time.

What unifies the shortcuts with the longer way of evaluating credibility is the evergreen rule of thumb “by their fruits ye shall know them” (Matthew 7:16). When you encounter a prospective teacher, pay attention to whether he has actually achieved what he preaches. Look to the results his students get. Are these actually what you want and in line with your values? Maybe you find a weight-lifting coach who is super-jacked, with a gym full of hard-bodies, but going to the gym is all they do. Is that truly what you want? Or would you be happier finding someone less physically impressive who lives a more balanced life?

At the end of the day, searching out from whom or where to get a start in a field brings us back to questions of maximizing versus satisficing: is it really worth spending way more time to find the perfect course of study than it is to spend a bit making sure you’re not falling for a trap, and then just go for the “good enough?” That will vary depending on what it is, how important it is to you, and what the potential downsides of getting it wrong might be, but for most things we concern ourselves with when it comes to productivity, they’re far more on the satisficing side: good enough now is better than perfect tomorrow.

The Skeleton of a Plan: Backwards Planning

Once we have some idea of what kinds of things we might need to do in pursuit of achieving our goals, we need to know in what order to tackle them. One good way to get at least a first approximation of a plan is called “backwards planning.” It works pretty much like you might expect from the name: start at the end state you want, and then ask “what needs to happen before that to get there?” and repeat as needed. A simple example: I have a class to teach at 9:00 am, so I need to be there, ready to teach by that time. What needs to happen right before that? Well, I need to get to the class early to set it up, call it 8:50. What about before that? Well, I need to print off some materials, so call that 8:45. Parking and walking to my office, 8:40, driving to work at rush hour, 7:40, grab things to go out the door, 7:35, pack my bag, 7:30, get dressed, 7:20, shower, 7:10, quick morning workout, 6:55, brush teeth, 6:50, add another 10 minutes for random friction or being slow to get out of bed, and I know I need to be up no later than 6:40.

The first thing to note about this process is that when it comes to the time estimates, you have to have a lot of familiarity to make them accurately. I’ve been paying enough to attention to my whole showering, brushing hair, getting dressed, etc routine to know it takes me about 20 minutes usually. On the other hand, when I first started doing morning calisthenics, I had a much more optimistic idea of how quickly I could get it done and didn’t take into account getting off to a slow start, resting longer than strictly necessary between exercises, and so forth. A good rule of thumb if you’re trying to account for time in your backwards planning is to always err on the side of estimating more time than you think it will take, so if you think it will take 15 minutes, allow 20 or 25. Also, speaking of the accuracy of estimates, when it comes to anything that takes more than about an hour to do, we’re really, really bad at estimating how long it will actually take. Things we think will take an afternoon take a week, things we think will take a week get knocked out in two days, that kind of thing. So, while this technique can usefully be used to generate a timeline for longer term projects, take your first pass with a hefty dose of salt.

The second thing to know about this process, and this applies whether you’re including a timing component in it or not, is that it works best when you can clearly visualize what comes before a step you’ve already reached, either through familiarity or due to obvious causal factors. For example, on the familiarity side, I can picture myself spending 5 or 10 minutes for the last “wrap up” stuff on the way out the door, even though that might not be obviously “necessary,” because I’ve had enough days where I get to the car and realized I’ve left something, or I grab some last minute food to eat on the drive, or whatever. On the other hand, you can sometimes reason out what has to come “next” (going backwards), even if you haven’t done it. Like this: “Okay, so I want to see Mount Fuji. Which means I’d have to find a way to Mount Fuji, maybe a train? or a rental car? And I guess that would be coming from Tokyo, so I’d have to find a way to Tokyo, obviously flying. To fly to Tokyo I’d have to drive to the airport from my house, or take an Uber. And before that, I’d have to buy tickets and find a hotel.”

When it comes to translating longer term or intermediate goals into a plan of action, it will usually be some mix of the familiar and unfamiliar, the granular and the not-so granular. Rather than the strictly reverse-linear plan I did for Mount Fuji above, it’s far more likely that if that were a goal of mine, I’d first work out “okay, when do I have time off from work, and can I find a good deal on flights and a hotel” well before I start worrying about getting to and from airports or exactly how I’ll get from Tokyo to the mountain. The day of the visit, though, I might engage in the same very granular time planning I used for the first example to figure out when I need to get up and out the door of the hotel. The point of introducing backwards planning is that if you already have a goal, you already have some idea of where you want to end up, which might be more than you have for where to start. Sometimes your backwards plan will be something like “Book successfully published, so before that I need to find a publisher, and before that I need to write a book, annnnnd before that I need to, I dunno, figure out how to write a book?” At least it’s a start!

Following Processes vs Setting Goals

I should mark that so far, I’ve been assuming that we have a clear goal that we’re pursuing, since that’s been the overall thrust of our efforts here thus far, but there is another way of approaching productivity that works better for some people in some situations, which is to develop a process to follow, rather than setting a goal to meet. I believe I first encountered this way of looking at things in Scott Adams’s How to Fail at Almost Everything and Still Win Big. A goal is a set, definite end state that you achieve, and that’s it: run a marathon next year. Once the marathon is run, check the box, the goal is over and done with and no longer has any bearing on what you do. A process, on the other hand, is a way of doing things that can keep going indefinitely: run for at least 30 minutes three days a week. You pick a way of doing things and then just start doing things that way, and you can keep it up as long as you find it helpful. Some more contrasting examples: read 50 books in a year versus read for 20 minutes every day, lose 10 lbs versus only eat within an 8 hour window, reach $10,000 in revenue versus cold call five potential customers a day.

Both of these approaches have their pros and cons, of course. Maybe the most obvious is that goals often give you a deadline, whereas processes don’t. That touches on a less obvious implication, which is that some people find goals extremely motivating (along with those deadlines that often come with them), whereas other people don’t. Some people find goals stress-inducing, whereas processes introduce a soothing and achievable rhythm. Goals may be great while they last, but what about when you achieve them? Now you need a new goal. Processes may be theoretically viable for as long as you want, but that can lead to stagnation if what started as a great way to build a habit becomes a plateau you could push past with some effort.

For most folks, I recommend a hybrid approach. Set some goals, but also establish some processes. Set goals in those areas where you want to push yourself, whether in terms of achievement or timeline, or where certain outcomes are part of the point (if you’re trying to make enough money from your side-hustle to quit your job, it makes sense to identify how much money that would be and make it a goal, for example). Use processes for those things that you want to become core, automatic parts of your life, like how you eat and workout, your baseline work habits, and maintaining perishable skills. And of course, you can combine them in ways that make sense: I’m going to write a book by the end of the year, and so to do that I need to write for at least 20 minutes every day.

The Role of the Will in Getting Things Done

We gave a whole post to the Will in the context of Strategy, and of course it comes up again when we’re thinking about the day-to-day. As we discussed in that post, the Will is not the same thing as motivation, though the two things can, and usually are, very closely linked, though they can be diametrically opposed at times. To use a perhaps overly-dramatic example, an alcoholic who has stayed sober for years has no doubt faced many times when he was motivated to drink, but his Will has restrained him from doing so. Most of the time when folks talk about “motivation” in the self-help world, they tend to only count the “good” kinds of motivation – feeling energized about getting work done, looking forward to how good you’ll feel after your workout, that kind of thing. But subjectively, and as far as I know biologically, that kind of “good” motivation is the same thing as the “bad” motivations to sleep all day, eat whatever tastes good, and drink all night.

Our Will, then, is what allows us to cultivate and make appropriate use of good motivation, and to hold back and eventually reduce bad motivations. There’s all kinds of works out there on cultivating the good sort of motivation (I found The Power of Full Engagement by Jim Loehr and Tony Schwartz pretty good), so I won’t go into it in too much detail, I’ll just give two helpful tricks, one for cultivating good motivation, and one for dealing with bad motivation.

First, for things you want to feel more motivated to do, find every way you possibly can to focus on the positive of it and remind yourself of that, up to and including creating positive associations that aren’t intrinsic to it. Say you’re trying to build up a habit of jogging, and it’s not your favorite thing (or maybe you absolutely hate it like I do – in which case, maybe consider finding another way to get your cardio). So, first off, you might remind yourself of how good you feel after you’ve cooled down, drank some water, and began to notice how much more energy you have. Or you might remind yourself of how since you’ve been more active, it’s been easier to stick with your eating plan and you’ve started losing weight, and you like how your clothes fit better. Okay, so much for focusing on the positive, now for adding some positives. Maybe you make jogging the only time you get to listen to podcasts (or certain music, or audiobooks, or whatever you like). Or you join a running group with people you like seeing. Or, and careful with this one, maybe you give yourself some kind of “treat” every time you go for a jog. I say be careful, because many people “treat themselves” after workouts with wildly unhealthy things and undo much of the health benefit that session might have had, especially if weight loss is one of your goals, since food “treats” tend to be of the high calorie variety. But this “overly compensatory” treat isn’t just about food. Say you study hard for an hour and then “reward yourself” with three hours of video games – a bit counter-productive, right? On the other hand, if after a jog you treat yourself to steak and eggs, or you go to a coffee shop instead of making coffee at home, or you get to take a longer, hotter shower than on other days, those might work just fine. Likewise, with the studying, maybe the treat is to go refill your coffee, have a healthy snack, read something of your own choice for a few minutes, or what have you.

From the above, you might think that the answer to “bad” motivation is punish yourself for following it, but it turns out that’s usually not super effective, not least because most of us are either too unwilling to actually punish ourselves, or far too willing to do so and go way overboard. So, instead, what I recommend as more likely to be a healthy and balanced approach is to analyze what you’re getting out of the things you feel motivated to do but would rather not do, and then try to come up with ways to address those wants or needs in ways you feel better about, by replacing the “bad” habit/motivation with a better one.

Let’s go with a fairly simple, light-hearted example here rather than trying to wrestle with things like addiction and compulsive behavior and what have you. Though, it’s about coffee, so maybe it’s a bit about addiction. Okay, so let’s say you’re a fairly typical office worker and drink lots of coffee. Less typically, though, you really appreciate good coffee, maybe you’re even a bit of a coffee snob. You’ve noticed, though, that toward the end of the day, you get a bit jittery, and at night, it takes you forever to fall asleep, even though you don’t drink any coffee after dinner and don’t feel “buzzed” on caffeine anytime near bedtime. You do some research and come to suspect that you might metabolize caffeine more slowly than other people, and that means that if you want to fall asleep quickly, you might need to cut off caffeine around 2:00 pm or something. This sounds awful, since your afternoon cup of coffee (or three) is what pulls you through the hardest hours of the day, but you decide to give it a try. After a week of holding strong, you cave and have some coffee in the afternoon, then you stick to the new habit a few more days, but it sucks, and so on, until you’re right back to your afternoon coffees and trouble falling asleep.

So, how might we apply the technique I talked about here? Well, first, ask “besides the caffeine, which we’re trying to get rid of as the point, what do you get out of the afternoon coffees?” Maybe it’s an excuse to go downstairs to the coffee shop, or over to the break room and chat a bit. Or maybe it’s a way to mark an accomplishment – “I went and got my coffee when I finished up that thing my boss needed.” Or maybe it’s the flavor, or the warmth of the drink, or pride in selecting/making an excellent cup of coffee, or the ritual of preparing it, or all of these things. So, one obvious answer would be try switching to decaf. That works great if it’s the warmth, the taste (sorta), the excuse to take a break and interact with other people, and so forth. But it’s less great if you really, truly do enjoy being a connoisseur. So, could you become a connoisseur of herbal teas? Are there ultra-fancy, high-end decaf blends that don’t suck? The point is, you try to find something that satisfies at least some of the habit you’re trying to change, but crucially lets you adjust on whatever points are most important to you, even if it’s not literally “wow, this is better” or “wow, I can’t tell the difference!” (for example, there are times where I would like a beer, but I think it would be better not to have one, and so I have a near-beer. It’s close enough to mostly scratch the itch, but it’s not the same, obviously).

Habit as a Tool to Strengthen the Will

If we’ve defined the Will as that part of us that chooses what to do, then it might strike you as paradoxical that I’m about to propose that habits are one of our best ways of strengthening it. After all, aren’t habits doing things without consciously choosing, but rather just automatically? The way I look at it is that habits, good or bad, are the accumulation of decisions, and so are something like credit and debit accounts of the will. “Good” habits are those where you have (or would like to) make deposits in the form of deciding to follow the habit, and the more you do it, the easier it becomes, I suppose like getting interest on those deposits (it’s not a perfect analogy, but I think you get the drift). “Bad” habits, on the other hand, are denominated in the exact same currency, decisions, but here, they become a drain on your ability to decide otherwise, to build up deposits in other habits, and so they’re more like debt.

So, it’s not that following a habit is negating the Will, it’s that habits interact with our Will throughout time. Trying to build up a good habit is exerting your Will, sometimes with some effort, now, so that your future Will will be strengthened in that direction. Fighting a bad habit now is pitting your current Will against your past Will. Following a good habit is aligning your current Will with all the weight of your past Will that’s been put into it already.

All of this means that forming “good” habits (by which I mean you consciously would like for them to be habits because they’re things you believe align with your values and/or help you reach your goals) is actually the main way you strengthen your Will. For one, it takes the effort out of doing some things, which leaves that effort available in other places if its needed. Also, the strength of all of the accumulated decisions in the past is very quickly going to exceed even maximum effort on the part of today’s Will. Perhaps a better analogy than the accounts earlier might be to imagine that you’re digging a mine for gold or gems. No matter how furiously you dig today, you’re not going to get as deep as someone who has been digging for days, or weeks, or years. But if you keep digging every day, you can get very deep indeed, and whenever you come back to the mine, you walk through the already excavated shaft and reach depths that someone just starting out on the surface would find hard to even imagine.

(I’m still not thrilled with this analogy, but hopefully we all get the idea).

Wrapping Up

We still have plenty more to talk about when it comes to getting things done effectively, but this post is already growing quite large, so I’m going to wrap it up here for now. Next time, we’ll cover some ways of thinking about prioritization, because it is often just as important to consider what not to do if we want to be truly effective. After that, we’ll dive into a grab bag of some of my favorite tips and tricks pulled out of the world of productivity and my own experience applying them, focusing on those that have the best “bang for their buck” – relatively easy to try out, but likely to show some results without some very involved system. Thanks for sticking with me for this, and if it spurred any thoughts or questions, or even better, if you’ve found any of the above helpful, do please let all of us know in the comments.