I've gotten much better over the last few years. I used to try to remember everything, and rely on reminders from others. Looking back, it's a wonder I got through college.
So here's The System as it currently exists:
I. Plan Your Work, then Work Your Plan
I use a Moleskine day planner with one page per day. Each day has two to-do lists: the work-related list, and the off-time list. I do my best to log everything I do each day. When an item is done, it gets a check next to it. If it doesn't get done, it gets an X, and gets re-entered one the day when I plan to do it.
I also log important calls, car repairs, bills paid, flight information, confirmation numbers, etc. In the book. Having a detailed record of my days has been invaluable.
And I've found that a simple, flexible system works better than something more structured.
II. Get it in Writing
Mistakes happen, and institutions do not care what their representatives tell you on the phone. They care only about what is on record. When banks, landlords, billing offices, credit cards, etc. screw up, having them admit fault on the record is the only way to keep the fallout from landing squarely on me.
So I make sure to get a letter from them stating what happened. It has to say what the mistake was, and that it was not caused by Chris Raser.
II a. Get a Receipt
Any institution's favorite way to say you're screwed is, "We have no record of that." So make sure there's a record. If you have to turn in a form, don't just drop off the form or put it in the mail. FAX or email it so that you can prove later not only that you did send it, but what you sent.
III. Automate the Payments
The single most effective measure I've taken to get my credit cards paid down and regain control of my finances has been to automate payments whenever possible. Every paycheck gets sliced up and distributed to my credit card companies, student loan servicing companies, and my savings account. And every Monday and Friday I get my allowance in cash. Bottom line: I can only spend what's in my wallet, and the rest takes care of itself.
Having done this, I also recognize that mistakes happen, and that my bank has been the culprit more than once. So I set up the automated payments, but I don't totally rely on them. Every payday, I check all my accounts to make sure they're up to date. That way, the automation usually catches me when I forget something, and I usually catch failures in the automation in time to fix them.
IV. The Only Winning Move is Not to Play
You cannot outsmart a credit card company. They have seen it all before. Put the card away, automate the payments, check it twice a month to make sure you're on schedule, and never, ever use it. Any other plan will not work.