The posts so far have been less about confronting guilt, and more about different tools for shifting it. This is a valuable skill to generalize.
The posts in this series have developed three such tools for shifting guilt. In this post, I'll recast those three tools as members of the same family, so that you can start to see the pattern, and develop similar tools from the same family as you need them.
The tools that I have described so far shift guilt to one particular place: guilt about being unable to act as you desire. This is intentional — that is the one place that I know how to confront guilt head-on.
The first tool for shifting guilt is the tool of refinement. This tool is used on listless guilts in need of pointing.
Imagine finding yourself feeling vaguely guilty the morning after a party, having slept in longer than you intended, your head aching from a slight hangover. Imagine a vague guilt making your body feel heavier. Perhaps it whispers that the night was senseless. Perhaps it murmurs that you're wasting your life away. This is the sort of guilt that's amenable to refinement: ask the guilt what, precisely, it would have had you do instead of what you did. (It is important, when refining, to also possess the virtue of concreteness: do not settle for "I should have been studying." Demand a specific action: Which book? Which chapter?)
Sometimes, when asking the guilt what you could have done instead, you will remember that none of the alternatives were compelling. Maybe the party was for an old friend who you only see once every few years, and fulfilling the social obligation was better than the alternative. Maybe you were exhausted from a day of studying, low on human contact, and needed the party to reinvigorate you. When using the tool of refinement, the guilt sometimes simply disappears.
But often, the guilt gets more pointed. Perhaps you conclude you should have been working overtime so you could donate the money to a worthy cause. Perhaps you conclude that you had the opportunity and the stamina, but simply not the willpower. This is good! This is a success! The refinement has succeeded, and the guilt has come into more focus.
But more often than not, when you succeed at refining guilt, you find yourself left with an obligation ("I should have drank less" or "I should have studied" or "I should have worked overtime.") This has not yet shifted enough to be confronted. For obligations, you need the second tool.
The second tool for shifting guilt is the tool of internalization. This tool is used on guilts that stem from neglected obligations.
I strongly recommend that you staunchly refuse to bow to any guilt forced on you from the outside. You say you "should have" studied more, instead of going to the party? Says who? Cash out the should. Again, it is critically important have virtue of concreteness when cashing out a should: do not say "it would have been better for me to study more;" for this has not removed the should, it has simply hidden it inside the word "better." The way to cash out a should (and, thus, the way to use the tool of internalization) is to ask yourself whether or not it would be OK to drop the obligation entirely.
What would happen if you decide to never study that textbook again? Is it a relief? If so, then drop the obligation, and relinquish the guilt. You probably just accidentally confused someone's quality line with your preference curve. Sometimes, when attempting internalization, the guilt simply disappears. (Other times, part of the guilt disappears, and your find yourself again facing a vague, unfocused guilt. This is fine, and indeed quite normal — just apply the tool of refinement again, and repeat.)
But more often than not, when you threaten to drop an obligation entirely, some part of you protests. Imagine you're feeling terrible for failing to work overtime and donate money. If you ask yourself "what if I just never donate money to those worse off ever again?," then most likely, some part of you will protest "but that would be bad!"
This is good. It means you have your own reasons for wanting to donate, which means you can drop the external obligation and do it because you want to.
Why would it be bad to stop donating? Don't settle for answers like "because then I would be a bad person" — that's replacing one obligation with another. If you get an answer like that, ask yourself, "why would it be bad for me to be a bad person?" Remember that concreteness is a virtue. Don't settle for an externalized answer (such as "because then people wouldn't like me"); push on until you get an internalized answer ("because I prefer worlds where ______").
Keep in mind that there may be many different parts to the answer: if you use the tool of internalization and get an answer that feels uncompelling, such as "because I prefer worlds where my friends think that I am generous," then ask yourself something like "OK, let's say that my friends were guaranteed to think that I am generous regardless of how much I donate to people worse off than me, then is it OK for me to never donate to people worse off than me ever again?" — You can keep doing this until you uncover all the reasons behind your desires.
This is how the tool of internalization shifts guilt: it forces the guilt to either resolve itself, or reveal itself to you in terms of your own desires. It shifts the guilt to a place where the thing the guilt demands are things you want for yourself, rather than things you want because you think you should.
So perhaps now you feel guilty for not working overtime to earn money to give to those less well-off than yourself (which is something you desire due to a deep dissatisfaction with the unfairnesses of the modern world). This, again, is progress: the guilt is now focused and internalized. This is exactly the sort of guilt that the third tool addresses.
The third tool for shifting guilt is the filter of realism. Look at your guilt, and ask it whether its demands are realistic.
Ask whether you really could have worked harder and done something else, while remembering that you are in fact mortal. You are no more able to work 20 hour days at peak capacity than you are able to cure Alzheimer's disease with a snap of your fingers. Look not to whether you were moving as fast as you physically could. Instead, look to the streams you need to move through in order to achieve your goals while remembering that two of the most important streams are maintaining health and motivation.
Do not ask, "could I have skipped the party and worked more?" Ask, instead, "am I traversing the work streams at the fastest sustainable pace?" Check whether the task the guilt demands is realistic. Remember that working yourself ragged is not a virtue. When keeping the filter of realism in mind, many guilt simply fail to materialize in the first place.
But some guilts do pass the filter of realism, and leave you lamenting a flaw in your process, an inability to do what you think is best. Perhaps you will notice that you attend parties far more often than you prefer, due to peer pressure. Perhaps you will notice that you actually find parties draining, and that you were only attending this one in hopes of finding a date, which you could have done in a less costly manner if you were really trying. Perhaps you will realize that you've been adrift, that you've lost focus, and you'll feel guilty for failing to maintain your drive.
And this is right where we want the guilt. If you must feel guilty, I recommend feeling guilty not about what you did or didn't do, but about the pattern of behavior that corresponds to acting against your will. Don't feel guilty for going to this party, feel guilty for the general pattern of giving into peer pressure, or misjudging how much fun you'll have, or overindulging. Because this is the sort of guilt that I know how to address head-on.
The three tools of refinement, internalization, and realism, are, in my case, effectively universal: I can use them to shift any hint of guilt up to specific, internalized guilt about a realistic concern at the process level. I am sure, though, that for many of you, there will be other forms of guilt that these three tools do not cover.
This is why I make the tools explicit here: so that you can see how they work and see what they share, and then construct your own variants that work on whatever other guilts you tend to encounter.
As you hone those tools, I recommend you seek a similar endpoint: shift the guilt away from the misstep and onto the systemic flaw in your footwork. Shift guilt from the instance to the pattern. Bring your guilt to this battleground, and I will show you how to defeat it.