Here is an interesting exercise. Whenever, you have a 'should' statement, see if you can change it to a 'can' statement, and notice being more empowered. Examples:

Not, I should be grateful. Instead, I can be grateful! [To clarify, I mean that being grateful is something that will make you feel good. As an analogy, if you have tasty cookies lying around the house, you will say to yourself: "well, I can certainly get cookie."]

Not, I should leave a generous tip. Instead, I can leave a generous tip! [As in, you can leave a generous tip and feel good about it.]

Not, I should donate to charity. Instead, I can donate to charity!

Not, I should loosen-up sometimes. Instead, I can loosen-up sometimes!

Not, I should keep in touch with old friends. Instead, I can keep in touch with old friends!

Not, I should learn to program. Instead, I can learn to program!

Not, I should eat healthy. Instead, I can eat healthy!

The general pattern here is that, instead of making the activity a moral duty, you can make it something fulfilling which you choose to do because of its benefits. 

For 'should not' statements you can substitute: 'I choose not to.' One example (you can make up more):

Not, I should not eat refined sugar. Instead, I choose not to eat refined sugar.

I'm sure that this procedure doesn't always work and you can generate counterexamples. I have not done them here. Please share your examples (counterexamples).

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Other possible expansions of "I should X", which I find applicable at various times:

  • I could X
  • I might like the results of doing X
  • I think it might be a good idea to X
  • I wish I wanted to X
  • I think [bad thing] will happen if I don't X

This is fantastic!

I think I should've (it would've been better if I had) thought more carefully about the senses in which "should" is employed. I should also have identified more circumstances under which some substitutions might help and also where they won't. My single identification of one narrow circumstance with one particular potentially useful substitution was clearly underwhelming.

This mucking around with surface connotation has a feel-good quality that I find drastically unappealing and to be avoided like cancer.

[-]seez50

You should be precise with your language. You can tell little old ladies to walk faster. "Should" and "can" mean different things. How about we just enjoy our abilities and use our words correctly?

"I should do X" sometimes means something a lot closer to "I have an obligation to do X" rather than "I want to do X and am willing to pay the costs associated with doing so"...

[-]AndekN110

Exactly. I think almost every "should" statement includes an unspoken "...but I don't want to" in the end.

For some more than others.

One obvious avenue of power over others is convincing them that morality is obedience and obligation to some external authority, with either direct or indirect assumption of that authority. For some, this turns morality into a tie and a fetter to be resisted, instead of an avenue for satisfaction of some of their own preferences - their moral preferences.

But some others are looking for an external authority, and relieved and grateful when they find one.

Amusing scene from The Avengers:
Loki: [to crowd]

Kneel before me. I said… KNEEL! Is not this simpler? Is this not your natural state? It’s the unspoken truth of humanity that you crave subjugation.

Compare to George Bush, West Point Speech 2002

No people on earth yearn to be oppressed, aspire to servitude,...

My money is on Loki.

The real funny part is that in searching for this quote, I got it from a Christian blog:

Jesus doesn’t rule like that. His yoke is gentle. His ruling activity in our lives is like nothing else we’ve ever experienced. Being Jesus’ servant really is freedom
... We really were made to be ruled — but not by Loki. Not by men like him. We were created to be ruled by God — and his leadership is unlike any we’ve ever experienced on this earth. It’s a good thing. His leadership truly is freedom.

And I will bow to that!

Arbeit macht frei! Which apparently ties in quite nicely.

La Wik:

In "The Kingdom of Auschwitz", Otto Friedrich wrote regarding Höss [ed. Commandant of Auschwitz]:
He seems not to have intended it as a mockery, nor even to have intended it literally, as a false promise that those who worked to exhaustion would eventually be released, but rather as a kind of mystical declaration that self-sacrifice in the form of endless labour does in itself bring a kind of spiritual freedom.

Indeed, there is. I don't like this particular way of removing the word "should" since it seems to ignore the unspoken "negative" bit, but I've played around with a similar exercise of removing "should" from my vocabulary so that I would have to speak the unspoken bit.

Constantly doing things that you don't want to do isn't a fun way to go through life. It's not effective at making good decisions either. The "I "should"/"have to" do this thing that I don't want to" frame presupposes that the alternative is realistic enough to yearn for but you're not doing anything about it!. If it's realistic, do something about it. If it isn't, shut up and be content. Shit or get off the pot.

I can make any choice available to me. My actions have consequences though, and I can't fulfill all of my desires. Of my choices, which do I want? Of course I can eat healthy, but that means I can't eat junk food. If I have to consciously force myself to be excited about eating healthy, maybe it's because I like junk food and I'm not thrilled about giving it up.

Once I can verbalize that unspoken wish to eat junk food and eat healthy, then I can make my choice and feel like I'm doing what I want to do (without "will power" or nagging thoughts).

So that's why/how I try to minimize my use of "should". Of course, it takes a bit of time and so for trivial matters I just shrug it off and say "opportunity cost"

The etymology of "should" includes variations on owe/guilt/debt - obligations.

Sometimes you would do the same thing anyway if it weren't an obligation. If that is the case, it's much more useful to focus on the fact that you want to do that, because obligations carry a negative connotation. In fact, I think focusing on the 'should' may sometimes create the '... but I don't want to' AndekN mentions above, or at least reinforces it.

Should => Obligation
Can => Power and Opportunity

"Have to" and "get to" have a similar dynamic.

Having spent periods of my life unsuccessfully looking for work, I remind myself during my commute that I don't "have to" go to work, I "get to". A job is a privilege and opportunity.

[-]eurg20

Depending on personal specifics, such stuff is also used in psychotherapy; overburdening oneself is not an uncommon problem. For me this helped even though such substitutions were all but universal, I don't know about how important it is in general, though.

Isn't "ought implies can" a standard principle of ethics? (That is, if something is actually impossible, in the "building a perpetual motion machine is impossible" sense, you can't be morally obligated to do it.)

I agree that feeling guilty due to the feeling that you should be doing something is harmful rather than helpful. Feeling guilt over procrastinating has only ever made it worse for me. I agree that such implicit beliefs about what you ought to be feeling are best gotten rid of as quickly as possible.

However, I am not so sure about replacing it with can. "I can do my thesis" does not make me feel anything. Rather, I like to ask myself what it is I truly want to do, and then the answer I give myself is "I want to do something with my life, and right now that means I want to finish my thesis". Want seems much stronger to me than can.

I'd write more but I should stop procrastinating on Less Wrong and go back to doing my thesis. I mean want.

There are two senses of should. One is "If you want A, then you should do B", meaning that B makes A more likely. The other sense is that of duty, of having a moral debt that one is obligated to pay.

When morality is treated as a duty, what one "should" do, it is an imposed burden, and some people don't like to be imposed on. Moreover, these people will look for ways to evade that burden.

When, instead, they say "I can act according to my moral preferences", they are picturing the satisfaction of acting according to their own preferences, similar to "I can eat according to my taste preferences".

It's the alienation of values into the imposed will of external and sacred authorities that causes the problem for some. Some people don't wish to be slaves. They're probably in the minority. For those who like being subject to an authority to whom they owe obedience, alienation of values to an external authority probably helps them achieve the values imposed by the authority.

The other piece is that your sense of duty isn't an infallible guide to living well any more than your immediate impulses are.

I think the two senses are really the same: if you accept consequentialist ethics, then the moral debt meaning can be translated as "If you want utility for person/group X, you should do B".

Whenever people use this word "should" in a sneaky way in a debate, I always find myself reminding them that it only has meaning with respect to someone or some group's preferences, and by glossing over exactly who's preferences we're talking about, people can get away with making bad arguments.

I think that's over generalizing consequentialist ethics.

"I want to fix my car."
"You should talk to Joe - he knows a lot about cars."

The latter is perfectly ordinary usage, but generally not considered a moral or ethical statement.

I'm not saying that ordinary usages of the word "should" are statements of morality, rather the opposite: statements of morality can be translated into ordinary usage, and if they can't they probably aren't coherent statements.

"I am morally obliged to treat this person's injury" "Why?" "Because it would stop their suffering"

Perhaps we prefer to call it a moral statement when it's about other people's utility functions, rather than our own. Then again, we usually don't feel morally obliged to cater to others' preferences except to the extent that we have a preference of our own for their preferences to be satisfied, which, thankfully, most people do.

While I can see the appeal of this, on the other hand I'm a bit leery about expending mental effort to suppress one's emotions. The central question is whether diverting your attention from a particular feeling trains your mind to actually not have that feeling, or whether it just reduces self-awareness and prevents one from dealing with that feeling. Getting the wrong answer to that question can result in rather bad outcomes.

(This is misleading for risky/complicated tasks.)