Which society exactly are you referring to? What crime are you claiming that every single member of this society is complicit in? How does feeling like a criminal itself absolve someone of complicity in this crime? You seem to be saying we should take on guilt for something precisely in order to free ourselves of this guilt. This seems like a paradoxical admonition. Could you please clarify?
Essentially, in modern society, if you do not feel like a criminal, it's because you are walking on eggshells around your government. Just about every modern government has laws on the books which are just plain ethically, morally, or constitutionally unjustified.
The DMCA, the PATRIOT act, the listing of cryptography under non-exportable munitions, the War on Drugs, the US foreign drone strike program, whistleblower laws, same-sex marriage laws or even death penalties, (soon to be) Article 13, social credit systems, mass surveillance, threat of ostracization/deplatformization if you fall outside of or in the middle of the now-split Overton window, the militarization of police in some developing countries coupled with a growing propaganda-driven movement to disarm citizens in order to increase the power gap, neoliberalist consumerist lifestyles propped up by military coups, dictatorships, and pollution sinks in developing countries.
I could keep going. But what it boils down to, is that if you don't find yourself at odds with the way things are being run in most parts of the developed world (not just the US) then you're either living under a rock, or complicit. If you're in the UK, it also means you like your sex without salt.
And, as ignorance is not an excuse in a society where you have plenty access to such information, you are still complicit.
I think a bit of guilt over the way our lifestyles impact the health of the earth and the lives of other people is certainly in order. I think some guilt over allowing our brand new rebel government to turn into the world's largest bully and largest perpetrator/denier of climate change, some guilt over not participating in activities which put you directly at odds against your government for the sake of knowledge or ethics, is entirely in order. Guilt gets things done.
I spent a lot of time in therapy, so I don't suffer a lot of existential guilt. I've generally walked the walk on things I believe in, so I don't have a lot of guilt of the type you are describing.
I'm not unaware of the fact that anyone can potentially find themselves tossed in jail over basically bullshit reasons. This happens at times to tourists who are doing nothing wrong according to the law of their country, but it's a serious offense in the country they are visiting.
My last boyfriend spent three years in prison in his youth for his political activism. He also was trying to talk me into illegal activities that would have benefitted him and not particularly endangered him. He tried to justify this with reasoning similar to yours.
So I've had plenty of opportunity to think about such things and my mental framework is likely not anything I can adequately explain in a single comment on HN.
But perhaps an anecdote will have a modicum of value.
I had food stamps for part of the time that I was homeless. Food stamps cannot be used for non food items and it is illegal to convert them to cash by, for example, offering to buy groceries for someone in exchange for cash for a portion of the value.
There is one loophole that I know of: food stamps cover the CRV, a charge on cans and bottles in California. You can then take the cans and bottles back for a cash refund after consuming the contents.
A lot of homeless people break the law regularly as a matter of course merely to survive or merely by existing. I no doubt was breaking the law every single night by sleeping someplace I wasn't supposed to be.
But I didn't use that as an excuse to justify doing any damn thing I wanted and to hell with the law. I did my best to find legal ways to get my needs met to the best of my ability.
While homeless, I was repeatedly offered money for sex in a state where prostitution is illegal. I have zero moral qualms about the idea, but was celibate for medical reasons, so wasn't tempted to take the money. I also had it hinted to me that I could potentially get scads of money from some guy I knew if I would launder some of his money. I ended our so called friendship.
Among other things, I run several blogs to put out useful info for homeless Americans. I do this in part to try to point them to practical legal solutions that have some hope of actually working.
I also do my best to put out good information on what we can do to actually improve things in a way that will help address the issue of homelessness. I'm aware that it is a genuinely hard problem. I have done a lot of research and I try to educate people while keeping the information accessible in a way that conceptually simplifies a complex issue without distorting it or watering it down.
I believe the solution to the issue you are wrapped around the axel about is twofold:
1. Educate people about what they can do to get their needs met that is legal.
2. Increase the availability of viable, legal solutions.
I do my best to walk the walk on that conceptualization of the problem space. I'm aware I'm only one person and there is only so much I can do, so either the road rises up to meet me or I'm doomed anyway.
I'm plenty frustrated at the fact that the road mostly does not appear to be rising up to meet me when it comes to certain things. But that's not on me. That's mostly on other people and their shit.
My websites don't get a lot of traffic, nor do they make much money. Other people mostly are not promoting nor supporting my work.
In fact, I get actively stonewalled. For example, I was thrown off of Metafilter, nominally for "promoting my websites." It's basically a cesspit of classist asshats, so my real crime is probably something more like "having the ridiculous expectation of being treated like a human being."
The world has hung plenty of it's baggage on me already, thank you. I have no plans to agree to accept more of it. That includes yours.
If you worked on your framing, you might find that we agree on a lot of things. Of course, you aren't obligated to do that. I am equally not obligated to agree with how you choose to frame it.