Not enough planning tends to make us overspend. When we have absolutely no cash on hand or don't budget for extra meals out during a late soccer game and don't bring food with us, we just spend and guilt follows.
I haven't been looking forward a month and planning for that month's expenses very well. I programmed Quicken to automatically populate our register with items that occur on a monthly basis. Unfortunately, that type of planning is only good for the "perfect" budget from heaven scenario and doesn't take into account the extra things needed for certain months.
My goal this month is to look ahead and plan the extra meals and excursions we will be doing and make sure the money is set aside ahead of time. That way I will enjoy the time spent with family and not be nickel and diming everything because I didn't plan.