Sometimes, it feels like a lot of personal finance information is focused on stuff that you should have done differently - in the past. You know, "start saving for retirement early," and, "don't take out a lot of student loans." That's all well and good, but we can't change the past. Don't feel guilty about past financial behavior, it's not going to accomplish anything. What we all need to do is look critically at how we've behaved in the past, figure out what we did right and what we did wrong, and use that information as a tool to determine our future behavior.
There are a couple of different ways to look at this. First, we can look at the big picture to figure out where we need to focus. Didn't start saving for retirement early? Then you probably need to make this a high priority for the future. Does your past behavior show that you are great at savings? Good - don't change that behavior! Are you erratic with credit cards, going years without carrying a balance and then racking up $10,000 in debt? Think of a way to avert that pattern.
The other way is to look at little things. Where are the little leaks in your budget, or where are areas that you could easily save a little bit here and there? Yes, little expenses are little, but they all add up. If you could save $50 a month in five different categories, that's a lot of money!
For example, I know that I have an expensive snacking/lunch habit. Mid-day often finds me out of the house, ferrying my daughter to doctor's appointments, grocery shopping, meeting with clients, or general errand running. Mid-day also finds me hungry. It's so easy to drop $10 on a sandwich and a drink, $20 if I have a child with me. Do that twice a week and you've easily wasted $100 a month.
Without actually cutting back, there are still ways to cut costs. For example, we drink a fairly significant amount of wine, generally picked up in a rush from my favorite wine seller. As much as I love to support my neighborhood, locally-owned store, the neighborhood, locally-owned store a mile down the highway offers a 10% military discount on Mondays. If we planned ahead, and made one wine stop on Mondays, we could probably save at least $5 every week, plus about an hour of "we're out of wine, can you stop" trips.
Sometimes, looking at the past can be uncomfortable. I particularly hate considering how much money I wasted as a teen - I had an amazing job and if I had saved every 1/4 of that money, it would have been a lot. Then I consider the fifty million ways that money might have been spent in the last 20-some years, and realize that it may not have made any difference at all. Try to look at your financial past in a way that doesn't make you unhappy but rather pushes you to be smart in the future.