"Should" considered harmful

My last few posts have been aimed at addressing what I call the "listless guilt," the vague sense of guilt that stems from not doing anything in particular. I said:

The listless guilt is a guilt about not doing anything. To remove it, we must first turn it into a guilt about not doing something in particular.

If you didn't have a listless guilt, or if you did and the last few posts worked for you, then you may now find yourself wrestling with a very pointed sort of guilt that stems from not doing particular things. These next few posts will address the pointed guilts.


One of the most common sources of pointed guilt that I encounter stems from neglected obligations. Imagine someone who thinks they should stop watching Netflix (because they care about something important, and watching Netflix isn't helping), but who can't seem to stop. Or imagine someone who thinks they should be spending more time working on their thesis, but can't make themselves do it. Or imagine someone who thinks they should be smarter, and that their homework shouldn't be taking them this long, and who feels worse and worse as they work. In each case, the pattern is the same: the subject thinks there's something they should be doing (or some way they should be), and they're not doing it (or aren't being it), and so they feel really guilty.

I claim that the word "should" is causing damage here.

In fact, as far as I can tell, the way that most people use the word "should," most of the time, is harmful. People seem to use it to put themselves in direct and unnecessary conflict with themselves.

For example, imagine the person who wakes up feeling a bit sick. They may well say to themselves, "ugh, I should go to the pharmacy and pick up medication before work." Now picking up meds feels like an obligation: if they don't get meds, then that's a little bit of evidence that they're incompetent, or akrasiatic, or bad. Now they must go get meds, if they want to be a competent person. In the lingo of CFAR, this "should" is the exact opposite of an urge-propagation: it disconnects the reason from the task, it abolishes the "why". The person feeling sick now feels like they have an obligation to pick up medication, and so if they do it, they do it grudgingly, resenting the situation. (And if they don't, then they've failed, and they're at risk of failing with abandon.)

Now imagine they say this, instead: "ugh, if I went to the pharmacy to pick up medication, I'd feel better at work today." Notice the difference? Now the reason remains attached to the task. Now neither option makes them "bad," and both options are tradeoffs.

I see lots of guilt-motivated people use "shoulds" as ultimatums: "either I get the meds, or I am a bad person." They leave themselves only two choices: go out of their way on the way to work and suffer through awkward human interaction at the pharmacy, or be bad. Either way, they lose: the should has set them up for failure.

But the actual options aren't "suffer" or "be bad." The actual options are "incur the social/time costs of buying meds" or "incur the physical/mental costs of feeling ill." It's just a choice: you weigh the branches, and then you pick. Neither branch makes you "bad." It's ok to decide that the social/time costs outweigh the physical/mental costs. It's ok to decide the opposite. Neither side is a "should." Both sides are an option.

Don't say "I really should finish this paper." Say "if I don't finish this paper, I'll get a worse grade than I was planning to, and my teacher will frown at me, and my parents will frown at me." Then weigh your options. Then choose.

This is not necessarily easy! Breaking a "should" into its component goals, tasks, and desires may be particularly difficult for people who are still confusing the quality line with the preference curve and forgetting that it's possible for their preferences to diverge from the expectations of others. I've often seen people confuse "an authority figure expects me to try hard to do X" or "my friends expect me to do X" with "I should do X," and many people find it very hard to tease these apart. (Future posts will touch on this a little.)

Unpacking a "should" can also be very difficult for a reason that's a little harder to articulate. Have you ever seen a person who can't even imagine the thought of failure start to fail? They start to panic, their actions get rushed, their hands start to shake (which is particularly fatal if their task is one requiring dexterity), they put on blinders to the fact that they're about to fail as they frantically repeat an action they wish would succeed over and over.

The ironic thing is, especially in timed, dexterity-based tasks, if the person didn't panic, they would have a better chance of succeeding. It seems to me that, more often than not, it's the fact that they can't even consider their failure that is harming them most. If only they had come to terms with failure beforehand, then they could keep a level head as failure looms, and this would buy them one or two more shots at success.

This is related to leaving yourself a line of retreat: If you find yourself unable to think about a certain outcome, it can be very useful to think all the way through the painful outcome — not to convince yourself that everything would actually be fine, but just so that you can actually think about it. It's the thoughts you can't think that really screw you.

Similarly, it's the options you can't weigh that really cost you. People often seem to use the word "should" to assign a value of "negative infinity" to all alternative actions. They should do X, so if they don't do X, they're bad, end of story. Some people have trouble unpacking a should for the same reason they have trouble staring at a failure: they have a mental geas against seriously considering alternatives, against weighing them on the scales. One common symptom of this behavior is a tendency to do a fake unpacking of the should, e.g. by translating "I should finish this paper" to "I need to finish this paper": notice how this trades one negative-infinity analysis for another, without ever reconnecting the task to the goal or acknowledging the alternatives.

I'm not saying that the alternatives are always good: perhaps the should unpacks into "I want to finish this paper, because if I don't, then I will very likely fail my course, lose my scholarship, get kicked out of college, disappoint my parents, and destroy my job prospects." The alternative options might be really bad. Yet, I claim that there is power in laying them all out, no matter how bad they are. Make the values finite, so you can actually weigh them on your scales. When you should yourself without looking at the alternatives, you run a high risk of making yourself feel obligated and resentful. When you lay out all the options you can think of and choose the best, then it's much easier to work with yourself rather than against yourself — sometimes you have to settle for the best of a bad lot, but this is much easier once you've actually looked at the whole lot.


If you often suffer from guilt, then I strongly suggest cashing out your shoulds. Get a tally counter and start training yourself to notice when you say the word "should," and then once you're noticing it, start training yourself to unpack the sentence. "I should call my father this week" might cash out to "if I don't call my father this week, he'll feel disappointed and lonely." "I shouldn't play that video game" might cash out to "if I play that video game, I'll lose lots of time that I was planning to use for studying." "I should work on my homework right now" might cash out to "I want to have my paper finished by tomorrow, and I also want to go socialize right now, and these goals are mutually exclusive."

You can almost always re-state a should-sentence without the should. It may seem like a trivial transformation on sentences, but it might also really help remove the burden of an obligation.

Of course, cashing out your shoulds isn't all it takes to stop feeling guilty — not by a long shot. Once you've cashed out a should, you're often left with conflicting interests (remember that it's quite possible to disagree with yourself! I've seen people should themselves simply because they refuse to acknowledge that they might be under internal conflict). Frequently, after unpacking a should you're still left with a really hard choice. Furthermore, it's also quite common to cash a should out, weigh both options, decide that one option is better, and then still find yourself doing the worse thing. (This last problem is a doozy, and I'll discuss it more in future posts.) I'm not handing you a silver bullet, here.

But it's still a bullet. Don't use shoulds as an ultimatum! Your options are not divided up into "choices which make you good" and "choices which make you bad": your options are stratified by how much they move you towards the goal. So pick your shoulds apart into their component tasks and desires, and keep the tasks connected to the goal: don't say "I should get meds," say "I need to get meds if I want to feel good."

I've found it very helpful to treat almost all shoulds as a toxic attempt to blind me to the alternatives. Be careful: the thoughts you can't think do you harm, and the options you can't weigh cost you dearly.

So cash out your shoulds, and weigh all your options on the scales — and then choose what is best, free of obligation.