Dear Dave, 
I’ve been talking to my creditors, because I want to pay off my debt as soon as possible. In dealing with them, I’ve noticed sometimes they are reasonable and understanding, while other times they are pushy and even mean. Do you have any suggestions on dealing with creditors when you’re trying to make amends and correct financial mistakes of the past?  
Olivia

Dear Olivia, 
Let’s start with a few basics. When it comes to dealing with debt collectors, keep track of all calls and emails between you, and be 100 percent up to speed on all your accounts. Have records of all the payments you’ve made, and the dates on which they were made. Know what you owe, who you owe and exactly how much you owe them.

If a collector agrees to settle the debt, get all the specifics of that agreement in writing, and keep the document as proof—just in case they “forget” they made the offer. Knowing the facts, and having them close by, gives you the upper hand in any situation. Plus, all this will make it easier to report them, and begin building a case file, if they violate the federal Fair Debt Collection Practices Act.

Trust me, you’ll run into all sorts of collectors no matter what kind of debt you have. Occasionally, they’re friendly and reasonable. Others can be downright nasty. Whatever their approach, always remember one thing. Their endgame is to separate you from your money. Most debt collectors try to take advantage of a person’s lack of confidence and emotions. So, if you don’t know your rights, they can scare you by using bogus threats. Always calmly explain your situation, the reason you’re behind on the debt and how you plan to pay it off. Never let yourself get drawn into an argument, either. If they start yelling, calling you names or cursing at you, hang up immediately. Make a note of the call, and the name of the person you spoke with.

Any misbehavior aside, I want you to remember one thing. If you have debt, you have a legal and moral obligation to pay it. However, there’s nothing wrong with you calmly and confidently controlling these kinds of conversations. You may have made some financial mistakes in the past, Olivia. But that doesn’t mean you should allow someone to insult and abuse you.
— Dave

Dave Ramsey is a bestselling author, personal finance expert and host of The Ramsey Show.

Dear Dave,
I’ve made a lot of stupid money mistakes in the past. Even though I finally paid off six figures in debt a few years ago and am in control of my finances for the first time in my life, I’m having a hard time forgiving myself for all the dumb things I did. I have an emergency fund and other savings set aside, and I’m almost ready to buy a house. But it seems like there’s still a cloud hanging over my head from all my bad decisions. How do I stop obsessing over my past financial mistakes?
Brea

Dear Brea,
If you’ve had enough determination to pay off six figures worth of debt and to build savings on top of that in the last few years, you’re doing a phenomenal job! Most people would just make excuses or give up, but you educated yourself, put your head down and stomped out all that debt. I’m very proud of you, hon. What you’ve done speaks volumes about your character and self-discipline.

The late Maya Angelou once said, “Do the best you can until you know better. Then when you know better, do better.” That’s the key for you, I think. Doing dumb things doesn’t always mean you’re a dumb person. Sometimes, we just don’t have the knowledge or guidance we need to do things the right way. But once you learned a few things and saw there was a better way — a smarter way — you jumped in and made incredible things happen. You cleaned up your finances, and you changed your entire future for the better. I think that’s pretty cool. And you know what else? It makes you a pretty smart lady.

I think part of your struggle may be the fact that you’ve spent more time making the wrong decisions with money than you’ve spent making the right ones. That’s understandable. But time will help heal that struggle. It’ll distance you emotionally from the old you until you’re confident in the new you—not just in your actions, but in your heart and mind. I mean, think about it this way: If you violated trust with a friend, how would you rebuild it? First, it would take time. And second, it would take a series of trustworthy actions.

Let’s say someone had a drinking problem for a long time, but they’ve been dry for three months. After three months, their spouse still might not trust them with the checkbook. I totally get that. It’s a good start, but it’s not like they haven’t had a drink in three years. That’s where time comes into play. The more time they demonstrate a solid pattern of not going back to the bottle, the more evidence they create for why others should trust them.

I think you’ve developed a pretty good track record of being smart with your money, Brea. So cut yourself some slack. If God is willing to forgive us for the really bad things we say and do, you need to be able to extend a little grace to yourself for the dumb things in your financial past.
— Dave

Dave Ramsey is a bestselling author, personal finance expert and host of “The Ramsey Show,” the second-largest talk radio show in America.