There are probably as many ways to 'fail at life' as there are opinions on the matter, including yours.
Many of these opinions will contradict. Some will be informed, articulate, insightful; others trite, naive, crude.
Where does this leave you? To say that yours is the only metric which matters is tempting, but this might not actually be the case, as our lives are typically impacted by others, including by others who hold values in opposition to our own; it is normal for us - as a species who relies on cooperation - to deem the opinions and responses of others as crucial.
Maybe you're not governed by your own ideals. Maybe you seek to satisfy others more than yourself. What does this mean? Well... perhaps the first step is to identify what success and failure mean to you, and why. Then - if you are able to figure that out - you might have an answer to your question.
Once thing seems clear:
Given you have asked this question, and providing it is a sincere question, you can identify the fact that the notion of failure is important to you. You say you suspect you have failed at life. What does that failure look like? Why do you suspect it constitutes failure? Is that failure surmountable? Could it even have been avoided? What control have you had/might you have over it? Can your failures go on to inform successes, given how intimate you have become with the lack of success? In other words, can you identify something you might change?
You have identified the 'finest feeling' as catharsis:
"the process of releasing, and thereby providing relief from, strong or repressed emotions".
It might be worth asking yourself why you felt mentioning this was relevant. It suggests you - at least sometimes - experience strong or repressed emotions that you need relief from. Can you identify any of these emotions? Is there anything linking them? Do they have common source(s)? Are they emotions you would deem healthy or pathological in others? Are they impacting your life in negative ways? Might you benefit from experienced, professional help?
"The problem is that all I seem to engender is a headlong and deliberate rush to covert and inauthentic "rule-breaking" disguised as self-ownership and sovereignty".
There is a great risk here of misinterpreting your comments, so please read this with great skepticism, but it seems you have achieved a significant insight here; that you see you are acting in ways which conflict with your ideals; a position many of find ourselves in at times and which brings many of us a great deal of heartache. This is to some a key realisation; for it empowers us with a direction for change, ie. to find a way of living more aligned with the way we truly like to be.
A word of warning: if your values are sociopathic or dangerous in some ways, you must proceed carefully, for reckless abandon - if that is perhaps your true urge - is likely not in your or anyone's best interests.
I'll stop now, because this is transgressing into a realm better suited to a professional, more immediately interactive context. I don't mean to sound condescending here at all - I suspect you are far more intelligent than I am, and you are clearly possessed of valuable self-insight - but to employ a cliche, you have in clearly identifying "the problem" taken the most important step to solving it, whether or not that solution requires outside assistance or not. If you have not done so already, you might take a look at Socratic Questioning, which is a way of using your own intellect and insight to find solutions to your problems, in concert with/in lieu of external help.