Many of my friends during my college and early post-college years were swimming in debt, some of them to the point of being scared to open the mail. Whenever I would suggest talking to their parents or guardians about it, their faces would freeze with an additional layer of fear, as though it was the last thing on earth they wanted to do. They feared lectures, the feared they feared letting down their parents.

Since I’ve entered adulthood, I’ve had several long talks with my parents about various issues. My parents have always been quite easy to talk to, and when I had my own child, I asked them for advice on how they made topics that were so troubling so easy to talk about. Here’s what they told me, in so many words.

Don’t push. Adult children are often trying very hard to spread their wings and fly, but they will know better than you will when the time is right to ask for advice. Don’t pressure them into a conversation unless there is a strict need for it.

Admit your own mistakes. As children enter adulthood, the relationship between you and your children has to change; you need to move from being the superhero protector into being a respected and trusted advisor and friend. Admit where you’ve messed up in the past, too. No one on earth has been financially perfect, so dredge up a few of those mistakes and add to your own humanity. This will pave the road to a great deal of openness.

If you fear there are problems, let them know that it’s okay to talk about them. Tell them this directly, and bookend it with your own admissions and flaws.

Don’t be judgemental. The world of a college student today is substantially different than the world when you were that age. The culture almost coerces you to get into at least some debt trouble by making credit access so simple without explaining the drawbacks, and also making expensive consumer goods highly desirable. Student loans are also enormous, and they also have huge expectations of a great job after graduation that aren’t always feasible because a degree today isn’t worth what it was twenty years ago. Using your own experience as an indictment on theirs is completely unfair.

Ask questions and listen. When I had “money talks” with my parents, they quickly devolved into lectures in which I would sit there and nod my head and ignore every word of it. Instead of lecturing, ask them questions about how they’re spending money and listen to what they say. Questions that delicately lead towards certain conclusions are almost always better than lectures and pointed statements.

Give your child the benefit of the doubt. There are probably some issues that your child simply isn’t comfortable discussing with you - if you think back to that age, remember the things you were uncomfortable discussing with your parents. Allow them to throw dirt over their tracks; don’t spend a lot of time trying to wheedle out something that makes them uncomfortable. Quite often, if you show yourself to be approachable and demonstrate that you’re being attentive, they’ll tell you many things anyway.

Check in - but not too often. Some parents believe that when the child is out the door, you should let them call you; others try to call multiple times a day and still micromanage their lives. The best balance is somewhere in between: give them space, but remind them that they’re loved and that they have support. My parents called a lot at first (I was the only person I knew at my college and I got very homesick), but as time went on, they scaled back slowly, to the point where I called them more than they called me.

Tomorrow, we’ll expand on that final point and look in detail at the process of cutting ties, financial and otherwise.

For the longest time, my biggest obstacle to financial success was simply discussing matters with my wife. Money was the most uncomfortable subject between the two of us - every time we discussed it, even with the best intentions, one of us wound up very upset. So, for years it was a complete taboo topic outside of the functional “Did you pay the electric bill?” type question. When we finally sat down and had a real financial heart-to-heart, it was relevatory. We realized that we were on the same page on a lot of things, and that in our own separate ways we were making many of the same mistakes.

Here are ten tips for getting the discussion started - and making sure that it doesn’t devolve into an emotional battle.

1. Start off talking about goals. Ask your spouse when he/she wants to retire and what he/she wants to do after retirement. Ask what his/her dreams are - where would they like to be in five years, or ten years. The point is to think positively about money by asking where it can get you.

2. Admit your own mistakes. If you’re having this discussion, it’s likely you’re not blameless. Start off by admitting your own mistakes. Before the discussion, evaluate your own spending and figure out where you spend too much. For me, I admitted to spending too much on books and on eating out, both of which were seriously draining our finances.

3. Look your spouse right in the eye, and hold their hand. No matter how big your spouse’s mistakes are, never, ever give any sign that you are anything other than compassionate and loving. For me, this meant that as my wife was summoning the courage to express her fears, her spending problems, and her doubts, I sat next to her, looked right at her, listened attentively, and placed my hand on top of hers. It was a simple gesture, but it reminded her of the love that we share.

4. Be goal-oriented. You’re having this talk to achieve some sort of goal. Maybe you’re realizing that credit card bills are getting too high, or maybe you’re starting to think about having children - or about life after the kids leave the nest. Let your partner know what the goal of the conversation is, but don’t frame it around “you need to change your behavior.” Be very specific about what you want to accomplish: “I would like to get these credit cards paid off” or “We’re about to finish paying off the house and I’d like to think about an upgrade.”

5. Look at numbers - but don’t judge. When I did this, I let my wife see all of my statements first and gave her a pen to mark off anything she found questionable. She was so blown away by the openness that she almost automatically did the same thing once we evaluated my spending, and without a peep. If I had started off by demanding her statements, it would have turned into a giant war.

6. Be fair. If/when your spouse admits to overspending, don’t blow up at them. We live in a consumerist society that is designed to push our buttons and trick us into spending. Even worse, it’s a pattern that’s very difficult to break - it’s a very socially acceptable addiction. Instead of exploding, ask them what they think of the spending: is it reasonable? Is it more important to them than paying off a credit card? Do not blow up if your spouse gives an answer that you don’t like.

7. Create goals that you both agree on. Each of you should make a list of the goals you’d like to reach, both in the short term and in the long term. Then, find the ones that mesh together and agree to work towards them. For example, my wife and I are both interested in being debt free as soon as possible, buying a home in the near future, and retiring early, so we’ve made that one of our primary goals, and we now think of our spending in terms of these goals.

8. Create plans to reach those goals. For each of your common goals, spend some time figuring out how you can get there. Do you need to cut down on the Starbucks visits? Does your spouse need to spend less cash on authentic baseball jerseys (hey, I’ve seen a couple where the husband was budgeting almost $10K on baseball-related apparel a year)? Each of you needs to be willing to make some sort of sacrifice to reach the goal, and if you’re initiating this, you should be the first one to offer up something.

9. Agree to talk about it regularly. I am a big fan of a monthly family meeting about money issues. This should include the children as early as possible. This way, all parties can stay on the ball and everyone can have a say in any planning decisions.

10. Do something romantic afterwards. After our first talk, I made dinner for the three of us while my wife picked up our son from daycare. After supper and some playtime, our child went to bed, and we spent a romantic evening together, secure in the new bonds we had just built.

Eventually, there always comes a time in which a serious financial talk is required. You need to have a heart-to-heart with your parents about their retirement plans, your significant other is spending too much, or your children are wondering loudly about their college plans. Most of the time, we put off these difficult discussions because it’s easier than facing the music, but eventually matters reach a point where a serious talk is inevitable.

Here’s a gameplan for tackling these financial topics while minimizing the heartache. Approaching “the talk” with the proper preparation and attitude makes all the difference.

Do it sooner rather than later. If the problem is present now, avoiding it will only make it worse, plus the concerns will weigh upon you over time. Rather than letting this happen, plan the conversation for as soon as is reasonably possible.

Schedule plenty of time. Don’t tackle the conversation when one of the participants has a scheduled appointment. Allow yourself more than enough time to cover all of the issues that concern you. I recommend scheduling at least one solid hour for any major financial talk, if not much more.

Prepare the cold, hard numbers. Before you go, prepare as many numbers as you possibly can so that you can refer to the data during the meeting. You should also bring plenty of scratch paper and writing utensils so that all involved parties can present diagrams and take notes.

Listen. Money is a difficult topic and the other person is likely to be defensive. Instead of insisting on going over the top with your point of view, listen to their perspective and try to understand it. Ask questions in a calm and rational fashion, and write down any particular points they are insisting upon.

Never raise your voice. No matter what happens, try to avoid raising your voice. Financial issues can be extremely challenging to people’s emotions; if you’re the one who has thought carefully about the issue, you should be the one that reacts in a more rational fashion with less emotion. If the other person blows up, just sit back and wait until they’re done, then continue onward calmly.

Bookend it with love. The most difficult conversations about money are with the ones that we love. Make sure that you show that love both before and after the conversation so that the others understand that love is the real reason behind the talk. You want the money to be stable so that everyone can live a happy, healthy, loving life.