This App Will Continue to Humble and Teach You

I don't know if this is more of a rant/request for help/observation but either way I wanted to share my recent experience with YNAB.

We've been dutifully using YNAB for our finances since 2021 and it has always been steady for us to give us an idea of where our money is and how much we have to spend and what to put away towards goals.

This past weekend, though as I was about to pay my AMEX bill, I noticed the money in our checking account didn't match what YNAB said we had available. Before everyone comments, yes we don't reconcile as much as we nearly should, lesson learned. We will have to reconcile way more than what we used to (once a year maybe?) and do it weekly if not every other day. I reconciled all the accounts and it still didn't quite fix the difference.

We didn't do a Fresh Start because it doesn't solve the issue of available money since it just takes what is available and puts it back into Ready to Assign, which doesn't help the discrepancies. So we had to do sort of a "mini" Fresh Start and banish the discrepancy to a different category called "Oopsie" and then hide it. Not sure if this is the best way to do it, but it help reset what we had.

I guess I'm just pondering how this could have happened where there was such a large disparity (setting aside the obvious that we don't reconcile enough). We assign every dollar that comes in and spend within our means. We balance the budget at the end of every month to account for overdrawn categories. So is it really just the lapse in reconciling that caused the big discrepancy between what was in our accounts and what was available in our categories?