hiya hibb, i've had that all my life with the debts thing...not gambling or anything, rather ignoring bills and forgetting due-payments. you end up paying out so much more because of late fees, lawyer involvements and the rest.
dealing with finances is pretty much near the last thing you wanna think about: it requires concentration, discipline and organisation.
in a less money-orientated society we wouldn't be under such constant pressure but alas we are and somehow have to deal with it. i never really got on top of it except to plough on working so enough money comes in to eventually get my head above water...not always easy, i know.
tho' what's really helps recently is a method of keeping track via a spreadsheet: all my balances/ins/outs i've been accurately listing for about a year now and since then i feel more in control, which in turn makes me worry about it less. and if i wanna spend money on a luxury i check the spreadsheet to see if it's doable...it pretty much makes the decision for me so functions well as a 'support' method for controlling finances.
every couple of months there'll be an unexpected bill or carefree splash so i have to right away note it in the sheet then stoically plan the next weeks around it.
stoicism...i don't know how but the finances-spreadsheet helps me be this way...it's like a zen tool, the managing of numbers is quite soothing too.
if only i had similar results with 'to-do' lists!
all the best, mate