The end of the month is the true test of how well your budgeting is going. If, at the end of the month, you feel strapped for cash and that you hate life, then something is seriously wrong. As long as you are splitting out the major budgets (like groceries and shopping) by week, then the last week in the month isn't much different than the first week. On the other hand, if you spent most of it in the first three weeks, then the last week could be rough.
After you have made it through your first month on a written, well-planned, and executed budget, you should start noticing some things. First, you should start to notice that you know where your money is going. That is really the goal behind budgeting. The goal is not to cut back expenses, but rather to dictate exactly how your money is being spent. It should get you to your financial goals faster, whatever they are. If one of your financial goals is to buy a boat, then budgeting can help you do that. If you were running a large corporation, would you want to know how the money in that company is spent? Of course you would! Then why should your personal finances be any different. You spend a lot of time away from your family and home to earn the money you have. You might as well be a wise steward of it.
After a monthly budget ends, the next month begins. Both Mint and every dollar will automagically carry over your budget settings from the previous month when you start budgeting for the next month. But one thing that bugs me about Mint is that you can't budget in advance! You can only set the budget for June once June 1st hits. That part is really annoying, as it doesn't allow you to plan ahead very easily. Every dollar handles that well, but again, makes you pay for the automatic transaction tracking that Mint gives you for free. That's why we end up using a combination of both. Maybe I'll write my own one day that implements the best features from both.
What tips and tricks have you learned from your budgeting experiences? Please share them. I would love to learn what has or hasn't worked for you.