I have neglected to balance my checkbook in about three months. So what I do is:
I download CSV data from my bank. I run it through one script that parses it, and guesses categories for various transactions when it can, based on various heuristics that I have accumulated, and leaves their categorization as a "?" when it can't.
So I just C-s search through the file for ? in emacs, puzzling over how I want to categorize each item. This is the work of maybe 10 minutes at most. Only one mysterious deposit remains, from about two and a half months ago. Where did that $181.29 come from? I run another perl script to give me a nice ASCII-art tree diagram of all "accounts" (in the double-entry accounting sense of the word "account" --- each one is just one category of expense or source of income or perhaps an actual bank account of mine or whatever) in the system and I see that I have a travel account for reimbursable travel to MITRE for a job interview way back last year with exactly $181.29 in it. Oh, right, they did finally send me another check after I stupidly lost the first one!
Problem solved, everything is filed away into neat little categories, svn commit everything because it's all lovely flat text files.
I sometimes feel really guilty about The Actual Thing That Is Money, in that I feel tremendously lucky to (a) have a job right now and (b) have a job that I enjoy and (c) have a job that pays me enough to live completely comfortably by any reasonable standard. Like, technically speaking, I "earn" this money, but I recognize that a certain undeniable amount of good fortune and unearned privilege was also involved.
That being said, the way money works and flows around and satisfies conservation laws sorta if you don't think too hard (i.e. macroeconomically) about it, divorced for a moment from the way that it makes and all too often breaks real human lives, is strangely compelling.
tl;dr: computers make my life easy even though I am really lazy and forgetful