I use a number of different tactics.
The BF gets paid every 2 weeks (which I hate) and I get paid the 1st and 15th of the month (which I love). Since the BF's pay schedule is not consistent for the dates, it means that some months he gets paid as far back as the 19th of the month, and that money has to make it to the 1st when we pay the rent. Sometimes the check comes a lot closer to the actual due date of the bill.
I set up a spreadsheet with the dates of his pay checks, and what bills fall within that 2 week period and the total amount that we would owe. It gives us a picture of where there will be extra breathing room, and which weeks will be tight. In the weeks that are tight, it is pretty easy to pay something early on the previous check rather than end up being late into the following check.
The second thing I did was set up a pretty fancy spreadsheet for tracking our spending. I actually used the exact same sheet as a budget projection sheet, just slightly different.
In the left column I have two sections - income and expenses. Each section has categories broken down. Under income I have the BF's job income, my job income, a second part time job income, and gift income, as well as interest earned on the accounts. Under expenses we have a list of categories. These can be customized for you personally but our list generally looks like this: Rent, Utilities, Health Insurance (I pay for mine out of pocket), Groceries, Gas, Eating Out, Eating at work (separate category because the BF tends to spend too much on lunches), Vehicle Maintenance, Health/Wellness, Personal, Miscellaneous, etc etc etc. You can make as many categories as you like, but the more you have the more complicated it is.
Across the top of the page are the months of the year, so each month the total from that category is transferred onto the annual total sheet.
On separate pages I have line item entry list, plus a section where all the categories total up. Its a bit on the fancy side, but I found all the information for the formulas I used online by googling what I wanted the spreasheet to do (i.e. "How to get a total from one page of a spreadsheet onto another page").
The other key for me keeping track of things was that I found I could print transaction records from both my bank accounts and my credit cards by month. I can go in and export the information into a spreasheet, and then print it out easily so that I can use that to apply to my spreadsheet. Plus it gives me a printed record that I can easily keep with my receipts and things for tracking.
I'm sure this all sounds very complicated, but once it is set up and running, it works pretty well for us. I update at the end of each month once all the transactions are completed and then I have a picture of what we did for the month (and I can easily see where we over spent! Yikes!). If you don't track where you came from, you have no idea how to organize to move forward. Knowing what you are currently spending is the only way you can appropriately set achievable goals.
If you like how this sounds, feel free to let me know and I can attempt to send you a blank version of the spreadsheet that I designed. I found that it was easy to use and transferred the data for me, which reduced the risk for fat finger errors.
Best of luck
