One of the Five Foundations to Applying with Sanity is to talk to your family about money. Soon.

But that can be really hard to do. And how do you even start that conversation? To get some insight on this, I reached out to my friend Lauren Lindsay. She's a Certified Financial Planner; her job is to help people figure out how to best use and save their money.

I first met Lindsay when she gave a workshop for parents at my daughters's preschool about how to talk to young kids about money. She presented on the importance of teaching children the difference between spending, giving, and saving. Last week I had a 40-minute talk with her about how go about it when the roles are reversed and it's now the children who need to talk to their parents about money.

Star early. Lindsay says that the best thing to do is to start talking about financial matters early. It takes time to "make money a comfortable thing to talk about," she says, and you have to figure out what your family's "money message" is. The money message is the general way that you think about money in the big picture. It's not always a conscious thing. For example, some people grow up with the message that you might run out of money at any moment, and so you must always be diligent and save as much as you can in case that day comes. But someone else might grow up with the message that no matter what you do something unexpected can happen and ruin it all, so have fun with your money while you have it. Whether they know it or not, your family members have a money message that they're passing on to you, so the earlier you understand it the better. Another reason to start talking about finances soon is that the initial conversations are often very awkward, and it takes several rounds before you may start to get anywhere.

Start small. One of the reasons you want to begin talking to your family about the cost of college soon is that you probably don't want to start right off with college. "So, the next four years are going to cost us anywhere from a few thousand dollars to a quarter of a million dollars. What do you say?" may not be the best starting place, especially if money and finances aren't something you and your family normally talk about.

Lindsay says that one exercise she uses with new clients, before getting into their monthly cash flow or retirement accounts, is to give them an imaginary dining-out budget of $400. How do you spend that $400? One really fabulous meal, once a month, and cheap simple things at home the rest of the month? Or maybe a nice $100 meal once a week? Or McDonald's several times a week? Knowing how people think about dividing up their budget, and how it may be different than your own way of thinking, can be really useful. 

When working with younger, college-aged clients, Lindsay says she'll work through figuring out, based on your paycheck and reasonable budgets for rent and food and such, how much you can afford for a car. This may be another smaller way to get into thinking about college expenses: ask your family to help walk you through their process for making a college budget. It will help you understand not only how much they're prepared to pay for college, but why. You'll also want to go through the same process yourself, and talk them through it. How much is it reasonable to work while also in school? How much do you think you can and should borrow, and why? Having these sorts of process conversations are a good way to prepare yourself and your family for the actual bills that begin coming a little later.

(And remember, no matter what the list price is, you don't know what a college will actually charge you until after you've been accepted and get a financial aid package--so don't let the cost keep you from applying!)

Be compassionate. Lindsay also reminded me that money is, for most people, very emotional. She says that parents will sometimes feel shame for not being able to afford college, and the "predominant feeling is don't let the kids know, it will lessen us in our children's eyes." She told me about some clients who decided to put another mortgage on their house and pile up a lot of credit card debt rather than tell their child how unprepared they were to pay for college. As much as you would like for your family to be wealthy enough to just take care of college without having to struggle for it, you don't want them to risk financial ruin to keep up that appearance.

If your first conversations about finances don't go very well, understand that there's more going on than just your family being stubborn or weird. Let them know that you understand it's a lot to think about, that you're interested in doing more than just demanding money from them, and that you want to better understand everybody's role in this big investment--and understand them a little better. 

How do you think about money? Lindsay says that some of the first questions to ask may be general attitude questions that go back to the "money message." Try asking your family if they see money as generally positive or negative. Some people see wealth as a sign of good choices and strong foundations; they see money as a good thing. Others might see money as "the root of all evil" and feel money, even if a necessary evil, leads to greed and immorality if there's too much. Some parents want nothing more than for their children to be set on a path that will lead to a more wealthy life than they have; others are threatened by the thought of their children being better off. There isn't a right answer or wrong answer, but understanding how your family thinks and feels about money might surprise you, and is necessary to understanding the details of college bills a year from now.

How do you think about college? When Lindsay told me about the value of experiences over things, she said that "experiences, like travel or doing things together, usually has more bang for the buck than getting more stuff." That made me think that there are different ways to think about college as well. Do you generally think of college as a thing, a "piece of paper" that you have to get in order to move on to more important matters? Do you think of it as an experience, something that you go through to make you more developed as a person? Do you see it as an investment, something that you put money into so that you can get more money out? Of course, most of us know that college is to some degree all of these things, but you probably have one that dominates your thinking. Your family also probably have their thoughts about what college means, and they may not match yours. Trying to decide if college is primarily a thing, experience, or investment will not only help you work together on figuring out how to pay for it, but why.

College is one of the biggest, most expensive things out there. It's up there with buying a house or retirement. In most cases, paying for college involves both the student and the student's family. The more you and your family can all talk about that together, and the sooner, the more smoothly that big purchase is going to go. If the conversation doesn't go well the first time--even if it does--keep talking about it.