I’ve been keeping a checkbook on Quicken for years, and it’s great. The problem is with keeping a paper checkbook, which is necessary if you’re going to write checks when you’re away from the computer, synchronized with the Quicken checkbook. Once they get out of step, it can be very confusing to know what’s not in the other and why they don’t end up with the same balance. I’ve finally figured out how to do it.
If you can find a place where the balances match, you’re ready to start. Look at the next transaction in the paper checkbook. If it were the next transaction in the Quicken checkbook, you would be able to check that the balances after them match, or if not, make a correction. So, make that the next transaction in the Quicken checkbook by moving the things in between out of the way — by CHANGING THE DATES of the intermediate Quicken transactions to NEXT YEAR! Sure your Quicken register is now a lie, but it’s going to be easy to correct later. Keep doing that until you get to either the end of the paper checkbook entries or to an entry in the paper checkbook which is not in Quicken yet or to an entry in the paper checkbook which is now listed for next year in Quicken. If you’re at the end of the paper checkbook entries, you know that the balance in the paper checkbook is correct and all you have to do is add all the rest of the Quicken entries to the paper checkbook (and change the dates of each Quicken entry back to this year as you add it to the paper checkbook.) If you get to an entry which is not yet in Quicken, put it in. If you get to an entry which is listed for next year in Quicken, change its date to this year and check the balance as far as you’ve got. Keep it up until everything matches.
Suppose by some chance there’s a mistake. Of course you won’t have one, but I sometimes do. In that case, rather than scratching out all the numbers in the paper checkbook and having a big mess, figure out how much the mistake is and add a single correction at the end of the paper checkbook for it. In Quicken, because the point is to have all the numbers the same all the way through, add BOGUS ENTRY with the amount of the mistake at the point where you have a mistake in the paper checkbook. Sure, all the numbers in the Quicken register from there on are wrong, but they’re wrong the same way they’re wrong on paper, and you know exactly what you have to do to make them correct. When you work down through the paper checkbook to the place you’ve made the correction, go back and delete the Quicken BOGUS ENTRY. The Quicken numbers are correct again, and the balance should match the number on paper after the correction.