The Point of Easy Progress

by silentbob7 min read28th Mar 20216 comments

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A lot of our productivity happens in the form of “projects”: spending a significant amount of time pursuing a certain desirable goal by consistently working towards it. My attitude towards projects, how to approach them, how to enjoy them and how to increase the odds of success, has changed a great deal over the past 15 years. With this post I want to make three points of varying obviousness that emerged from these past experiences:

  1. The Approach Matters: one’s personal experiences while working on a project are not set in stone but can vary tremendously based on one’s approach. 
  2. Harmful Short-Sightedness: acting on short-sighted impulses can be harmful in two ways. It can make us follow tempting trajectories that ultimately lead nowhere, and it can cause us to give up because a small obstacle seems larger than it is.
  3. Point of Easy Progress: For many projects it may be possible to design one’s approach such that a “point of easy progress” is reached early on. From that point on, hardly any willpower is required to make progress and working on the project generally is more attractive than not working on the project.

The Difficulty Landscape and Why the Approach Matters

A simple way to visualize a person progressing on a project is to interpret the scenario as a 2D landscape: the person starts on the left, the goal is somewhere far to the right, and there are height differences in between. Going downhill is easy (e.g. the tasks at that point in time are fun and not too difficult, the person is highly motivated), going uphill is hard (e.g. the tasks are extremely boring, complicated, dangerous or in any other way unattractive).

I like this visualization as it’s easy and intuitive and works well to illustrate the points, and thus will stick to it throughout this post. One drawback however is that the image of a landscape suggests a certain rigidity: it may be appealing to assume that for any given project the landscape is basically predetermined – we just have to put in the work and make our way to the finish line, up and over all the slopes and mountains we encounter. The layout of the landscape may depend on where the person pursuing the project is standing initially, and what the goal actually is, but other than that there’s not much to do. 

My first point here however is that the landscape is not set in stone. Terraforming is possible so to speak. There are a whole number of ways in which one’s approach to a project can change the landscape in both beneficial and detrimental ways. To name a few examples:

  • Changing the order of actions
  • Changing the focus put on different aspects of the project, e.g. certain aspects of it might be considered inessential and thus scaled up or down or left out entirely
  • Changing one’s perspective, e.g. by finding new/better reasons for why the project is worthwhile, or reframing challenges as growth opportunities
  • Further variations may be the tools that are used in the process or the people one asks for help

Putting all this together, pursuing the exact same project or goal may lead to some very different difficulty landscapes based on what decisions one makes early on.

Sometimes a project may turn out to be a persistent struggle. It’s always difficult, and a lot of willpower and persistence is required in order to keep going and ultimately reach the goal:

Other times a project starts with a few challenges to overcome initially, but then comes to a point where the tough stuff is out of the way and working on the project starts being consistently fun and exciting. Then gravity is on our side and allows us to easily build momentum. We get to a state where progress happens naturally and is practically easier than not making progress:

Note again that both these landscapes can represent the exact same project, where only the person’s approach and planning differs.

As a simple example of this, imagine a person writing a novel. In scenario 1 they approach it such that they simply expect themselves to write at least one high quality page every day. There will be constant pressure and perfectionism involved, and every day might be a struggle. Some days might be better than others, but in the end this approach relies a lot on stress and willpower.

In scenario 2 the person approaches writing the novel a bit differently, and spends the first two weeks coming up with an inspiring plot line, interesting characters, and a lot of boring yet necessary research. This is tough and not very entertaining. But after these two weeks, much of the cumbersome work is out of the way, the general direction of the story is clear, there’s this brilliant twist in the second arc which the author is really looking forward to getting on paper, and they just can’t wait to get this neat story they crafted written down and published.

It is not hard to see how the person will have a better time in scenario 2 than in scenario 1. On top of that the final product itself may turn out better, as the person’s experience while working on the project directly influences the quality of their work as well as the risk of giving up prematurely.

Clearly the approach to a project matters a lot. And I see no reason why we should just naturally pick the best possible approach, which is why it makes a lot of sense putting quite a bit of effort into trying to do things right and laying out projects in a way that maximizes enjoyment as well as expected quality of the outcome.

Furthermore I believe most projects can look much like scenario 2, or even better, but before we get to that, let’s first talk about short-sightedness.

Short-Sightedness

One challenge we face when dealing with the difficulty landscape is that we usually don’t see the complete terrain. We primarily experience the current level of difficulty, i.e. the slope of the landscape beneath our feet. We may see ahead a bit as we have an idea of what the next actions are as well as how these actions will affect our experience. Yet, extrapolating further into the future can be difficult, and our minds are lazy. Simply assuming the immediate trend we’re currently experiencing extends as a straight line into the future on the other hand is easy and happens often enough. This tendency leads to two typical problems in the course of working on projects.

The first problem is that of falsely assuming a downward slope will continue indefinitely, often causing us to jump at that beautiful opportunity of gradient descent with maximum motivation, only to find ourselves crashing into a mountain shortly after. The ensuing disappointment leads to a sharp drop in motivation, possibly even resulting in losing interest in the project altogether.

This was also the prevalent pattern in my teenage years, when my main hobby was programming: Every other week I’d come up with that perfect idea for a video game, or some exciting tool I could develop, and having that amazing vision filled me to the brim with excitement. I would jump into it head first, work on it for a day or a week or two, but almost inevitably come to that point where it was clear that this is difficult. It took me a few years to figure this out and be a bit more far-sighted rather than blindly following every little exciting downward slope I could find.

The second problem is the exact opposite: seeing an obstacle ahead, and assuming this is what things will be like forever. This can be bad for at least three reasons. Firstly, the bleak outlook can reduce our enjoyment of the project, as this is not anymore a fun or exciting endeavor but a difficult one, one that we need to force our way through in order to some day reach that goal we’re looking for. Secondly, it may lead to procrastination and thus delay our arrival at the goal. And thirdly, this may even cause us to abandon the project, as we might reason that the goal just isn’t worth that much projected effort.

In summary, another aspect apart from the general approach that’s important to improving both our enjoyment of working on a project and also its expected outcome, is being aware of our tendency to naively extrapolate, and doing our best not to base our decisions on such imperfect extrapolations.

The Point of Easy Progress

I argued that the approach to a project matters a lot. In the next few paragraphs I want to add to that the claim that for certain projects it may be possible to find an approach such that a “point of easy progress” is reached early on: once that point is reached, barely any willpower will be required to make progress. Working on the project will generally be a more attractive option than not doing so. In terms of the difficulty landscape, the gradient will be a friendly downward slope, meaning gravity and momentum will be on your side.

There are surely projects out there that don’t allow this, but generally speaking it seems to me that it is true surprisingly often, and it’s a good idea to actively look for a reachable point of easy progress in any project one takes on.

One example of such a point of easy progress was the author who starts by doing the necessary research and constructing a plotline so exciting that they can hardly wait to get it on paper. Generally speaking, if a point of easy progress can be identified, we may end up with a landscape somewhat like this:

 

There may even be projects that just have almost no negative aspects in the first place and are exciting from start to finish:

 

When looking for a point of easy progress in any particular project, the following steps may be helpful:

  • Making a list of all types of tasks involved in the project, rating them by how “positive” (i.e. fun, motivating, exciting) or ”negative” (boring, difficult, uncertain, risky) they are. What feelings arise when thinking of that type of task?
  • For the negative tasks:
    • Are they actually necessary?
    • Can they be reduced in scope, or delegated?
    • Can they be made more fun or bearable?
    • Can they be moved to a more suitable point in time?
    • Is it possible to reframe them, or find positive aspects to them that make them seem more beneficial or acceptable?
    • Do they look more daunting than they really are, and getting through them may turn out surprisingly easy?
  • For the positive tasks:
    • Can they be amplified so that they make up more of the overall time spent on the project?
    • How can they be reached as early on as possible?

It seems generally useful to be very aware of what excites you in a project, and how to get more of that. And on the other side, sometimes the more negative parts of a project may originate from a cached thought or an implicit impression of how such a project should be approached, rather than what would actually work best for you.

When optimizing for such a point of easy progress, it may happen that projects start out with a “hill”. Work first, pleasure later. This is a feature, not a bug: knowing the peak awaits, climbing it may turn out much more enjoyable than it would without that positive expectation. This is why avoiding short-sightedness is especially beneficial in such easy progress scenarios. You don’t need to wait for the end of the project at some distant point in time, instead you only wait to reach that point of easy progress, as this can be seen as the project’s “event horizon”: once there, there’s no stopping, the project will be self-sustaining and almost inevitably lead to success.

Conclusion

This post is admittedly not the epitome of epistemics. The model and examples are simplistic, things are never that clean cut, easy or coherent in the real world, and you can find tons of exceptions to the rules proposed here, if they can even be considered rules in the first place.

The idea behind this post however is not to make a strong empirical claim, but rather to provide a model that may be useful to some; the idea of a point of easy progress being a possible state to reach in principle in any project seems to me like a useful framing. It entails putting motivation and enjoyment in a more visual context, helping by focusing on the meta level at a moment of high leverage (namely the very beginning of a project when making a lot of strategic decisions about it).

For me, the insights that ultimately led to this post made all the difference in a number of personal projects. One programming project in particular was lying dormant for years, until I recently realized that by reprioritizing things in a certain way I was only days away from a point of easy progress. Consequently, even these few days that I had considered to be an uphill battle turned out to fly by, as the prospect of finally reaching that point was so enticing that the more negative parts of the initial work faded far into the background.

If you have the impression that the concepts covered in this post can in any way be of use to you, I suggest picking any of your current projects or project ideas and going through the list from the previous section. If it leads you to any new insights, I dare you to share them in a comment.

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I really liked this. I thought the little graphics were a nice touch. And the idea is one of those ones that seems almost obvious in retrospect, but wasn't obvious at all before reading the post. Looking back I can see hints of it in thoughts I've had before, but that's not the same as having had the idea. And the handle ("point of easy progress") is memorable, and probably makes the concept more actionable (it's much easier to plan a project if you can have thoughts like "can I structure this in such a way that there is a point of easy progress, and that I will hit it within a short enough amount of time that it's motivating?").

This is novel, practical productivity advice--thanks! I'll try it out and see how it goes.

I think this post would be even better if you had some examples of applying the advice (the list of steps in particular) to a real-world project.

Thank you for sharing, glad to hear this framework helped you through some projects. I have a few remarks/questions: 

Could it be that the idea of "The point of easy progress" may become a case of short-sightedness? I have trouble keeping those two apart. I think the illustrations you provided help to make my point. This notion of "from now on, it's easy and smooth downhill" looks similar to the problem you illustrated in the first picture in the short-sightedness paragraph. Because you risk thinking "ah, I'm at this sweetspot point where there's only flow and success" and then you stumble against the unpredictable problems that reality has to offer. I see it more as a human desire than an actual possible state. Or to word it differently, the idea of “point of easy progress” may become an imperfect extrapolation in itself. So the key question here: how do you differentiate the point of easy progress with the false assumption of a neverending downhill to succes? 

Also, I'm not sure if our 'willpower' is sustained by the point of easy progress as a kind of path of least resistance. I tend to agree with Mihaly Csikszentmihalyi and his concept of ‘flow’ that we tend to seek challenge in order to enjoy what we do, especially when it becomes too easy. On the contrary, too much of a challenge indeed demotivates. But it seems to be more about the interplay between too easy and too hard than the notion of easy progress. If tasks become to easy without sufficient challenge, we tend to get bored. However, I assume your point of easy progress doesn't necessary mean that there's no challenges ahead, but it might seem so with the depiction of 'cool, relax, it's now the forces of gravity and momentum that take it over, lay back and enjoy the ride'. 

Of course, a lot depends on how you define certain concepts. Success, and motivation/willpower to do certain behaviour don't imply each other (you can be motivated to do ‘unsuccessful things’). Or you might be successful in a (what now appears to be) an easy task but won't make much more progress. For instance, you can learn to be very good at simple maths up to a point where your success rate is 100 % (full marks on math test with simple additions and subtractions), but you need to encounter this uphill part where things become disorienting, frustrating and difficult to solve more complex problems in order to progress in your knowledge. 

Please correct me if I misunderstood certain concepts. I’m curious to what you think about the above. 

Edit: some grammar and spelling mistakes 

Thanks a lot for your comment! I think you're absolutely right with most points and I didn't do the best possible job of covering these things in the post, partially due to wanting to keeping things somewhat simplistic and partially due to lack of full awareness of these issues. The conflict between the point of easy progress and short-sightedness is most likely quite real and it seems indeed unlikely that once such a point is reached there will be no setbacks whatsoever. And having such an optimistic expectation would certainly be detrimental. In the end the point of easy progress is an ideal to strive for when planning, but not an anspiration to fully maintain at all times.

Regarding willpower I agree that challenge is an important factor, and my idea was not so much that tasks themselves should become trivially easy, but that working on them becomes easy in the way that they excite you. Again that's something I could have more clear in the text.

but you need to encounter this uphill part where things become disorienting, frustrating and difficult to solve more complex problems in order to progress in your knowledge

I'm not so sure about this. I like to think there must be ways to learn things, even maths, that entail a vast majority of positive experiences for the person learning it. This might certainly involve a degree of confusion, but maybe in the form of surprise and curiosity and not necessarily frustration. That being said, 1) I might be wrong in my assumption that such a thing is realistically possible and 2) this is not at all the experience most people are actually having when expanding their skills, so it is certainly important to be able to deal well with frustration and disorientation. Still, it makes a lot of sense to me to reduce these negative experiences wherever possible, unless you think that such negative experiences themselves have some inherent value and can't be replaced.

Thanks for your humbleness in return.

I think it remains valuable from an idealistic point of view. And as with many idealistic views, the problems mainly arise when things become a little bit too absolute, not letting enough room for changing context. Nevertheless, this idealism can still have a value. 

Take for instance the first remark I made about the idea of “point of easy progress” becoming a case of “short-sightedness”. I find value in the idea of recognizing certain points in your progress and using them as a drive to continue and motivate yourself. As a matter of fact, this appeared to help you through some projects, and in the end, isn’t that what’s more important? I also have the impression that this is mostly the core of your message. The element that made me question was the idea of the “event horizon: once there, there’s no stopping” as an absolute statement that would be difficult to defend in practice. Lastly, there’s also the choice to approach this descriptively as how progress goes, or normative, as how progress should go. 

Regarding the need for frustration, challenge and so on, I also use a lot of assumptions stemming from my background in Psychology and existentialism. I hold the idea that positive experience appears to be relative instead of absolute, and positivity loses its valance without any negativity as a context. In this sense, some kind of suffering (how dramatic it may sound) is essential. It appears to me that it’s natural for people to hedonically maximize pleasure, and avoid suffering, which I believe is a good thing, a verry Human thing to do. However, we sometimes struggle with this kind of neurosis by overemphasizing this chase for the good and pleasure in a world where suffering is inevitable. 

The good academic in me would elaborate on this perspective and provide further evidence to this idea, however, it isn’t my intention for this comment to persuade anyone. Instead of me philosophizing about it, it might be more meaningful to have people trying out this ideal and reporting their good and bad experiences to update the model. 

Thank you for sharing this perspective! Couple thoughts:

  1. I was implicitly using similar approach by front-loading planning and creative work. Once that's done one can just execute the tasks without switching back into 'planning' mode.
  2. For the (repetitive) negative tasks, I would add considering automating them or minimizing your effort. It might also make sense to understand what exactly you don't like about them - sometimes this is something trivial and easy fixable (like some inefficiency). 
  3. 'Replacing guilt' series ("How we will be measured" post in particular) gave me a new perspective for getting rid of negative tasks (and tasks in general). Basically some of them might have nothing to do with the actual success of the project and instead just be traditions or rudiments. So instead of asking 'is this actually necessary', I suggest to ask 'is this important for the project and why'.