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My system
I use to have the same problem--how could I balance a checkbook if most of transactions hadn't been recorded. What's the point of balancing if you're in that situation! Getting my husband to remember to give me his receipts was the biggest hurdle, then I had to designate a place to collect them. Now, I have a pretty good system for handling our finances. Another issue I had was remembering to record the receipts and pay the bills. I don't have a designated time to enter receipts. I try to do it at least once a week. If you're having problems being overdrawn on your checking account, try to set up a buffer--deduct an amount from your check register (what you're using to record your transactions--paper, ledger, computer program), whatever your finances allow/need...$100, $500, $1000. Your accounts will still balance because you're using the starting/ending balance and transactions from your statement, not the current balances of the accounts. If you use Money, the 'withdrawl' you made will show up every month, but don't mark it cleared or you'll be off by that amount when balancing. Just remember to use your balance, the one from your register/system, to see how much money you have in the bank. Try to forget the buffer; it's not for spending!
To remember to pay bills I set up reminders on the MSN Calendar--it sends reminders via emails and alerts that appear on your 'My MSN' page.
This is the system I've developed over the years (well, the partial system--now that I'm trying to describe it, it sounds elaborate):
Have a desk or designated area where you'll process finances
Use a 5-shelf ' paper/file thing (don't know what else to call it)
Top--for receipts; when I'm shopping I try to put the receipts IN my wallet, but sometimes they just get
shoved into some part of my purse. Also, with the inbox thing on my desk, my husband knows where to put his
receipts. I also keep two envelopes. One for the checking accout receipts, the other for credit card receipts.
Once I register the receipt into MS Money I write Rec. (for recorded) on it and put it an envelope until it's time to
balance the accounts. After I balance (and I balance all out accounts...including credit cards/savings) I shred the
receipts I don't need.
In my filing cabinet I keep a folder for receipts I need to keep for warranty/returns/etc. On top of those receipts I
write 'KEEP!!" and the item/reason I'm keeping it.
Bottom shelf--where I put all the bills to be paid. Bills I pay online I try to record to Money immediately after I pay
it and also write the payment info on the bill itself--date paid, account paid from, date, confirm number and
write 'Rec' after it's recorded into Money.
When it comes time to balance, Money makes it an easy process. I compare bank statement with my records. I check them off on the statement as I go along. If an entry is missing from my records I put a large arrow beside it. Once I'm done, if I have arrows, then I look for husband (he can be bad about receipts too!), check my files, look for receipt on shelf or in envelope. Most months it takes very little time/effort to balance.
BTW, as odd as it seems, I have ADHD and am considering becoming an accountant. Even for me, I just don't see how those two things can exsist happily together--numbers, details and ADHD? However, I'm taking accounting classes to meet the requirements for the CPA exam. For some odd reason, finances/financial systems are the one productive thing I can hyperfocus on. In fact, I had to wrench myself out of writing about my 'system' because I realized was in that zone and it's very likely most of my 'audience' will have moved on or fallen asleep before reading this sentence.
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