When our oldest son was little, and had developed enough language skills to where he learned to ask questions, he didn’t waste any time in putting his new found skill to use. As young parents at the time, my wife and I were thrilled with his questions as it gave us the opportunity to impart the wisdom we had garnered through the years to our eager-to-learn son. Well, okay, perhaps it wasn’t quite that grandiose, but we did enjoy answering his questions. At least we did at first, and then it became old.

Like any child, it seemed at times like we were bombarded with the “Whys?”, “Why does it rain?”, “Why can’t I eat candy all day?”, “Why do I have to go to bed?”, and many thousands of similar questions. Like a rapid fire attack from a Congressional panel he asked constantly about the world around him.

Most of the answers were easy, but as he progressed from simply learning about the world around him to asking why he wasn’t allowed to do things others could the questions turned hard. The reason they were hard wasn’t so much that we didn’t have an answer but more that we were sensitive as to how we answered. What I mean by that is when Andrew asked why he couldn’t do something that was evidently okay for Terri and me to do, I wanted to give him a clear understanding as to why instead of simply exercising my authority over him. Obviously, there are things that adults can do (drive a car) that little kids cannot but when it came to basics such as “Why can’t I stay up late?” it was tricky.

Now I realize that you may be thinking that there lies an easy answer; “Because we are the adults and you are the child.” or the classic “Do as I say, not as I do.” But having been a kid once I was never too keen on either of those answers and wanted to teach Andrew in a different way than I had been taught. Or more to the point, I wanted him to learn and not just be told.

I have to admit that regardless of my aim I sometimes missed, and unfortunately dependent upon my mood at the time, he sometimes received one of the old school answers above. However, I made it a point to go over the “whys” with him on a regular enough basis such that he learned.

Despite the many questions, and answers though, he also learned from watching us as actions speak louder than words. So as we progressed through his childhood and we made one mistake after another with money, he was there to see – and learn – it all.

Without going into the details I’ll give you a brief summary. We bought a house that we couldn’t afford, opened a business whose finances were intertwined with our own, didn’t pay our bills on time or enough and as a result were foreclosed upon, had our only car repossessed out of driveway and ultimately filed bankruptcy. Even after all of that pain though we didn’t learn and went right back into debt and struggled to pay even the basic bills.

All the while, Andrew was watching and learning much the same as I had when I was growing up.

It shouldn’t have taken as long as it did but after more than 20 years as adults struggling with money, we reached the point in or around 2001 to where we’d had enough. As Dave Ramsey is fond of repeating; “We were sick and tired of being sick and tired.” As you may have surmised, we first heard of Dave around that time and took to his teachings excitedly with the hopes that we could finally end the vicious cycle we had lived in for far too long. It wasn’t until 2006 though, when I first found YNAB, that the budgeting part of Dave’s plan made any sense to me.

Since that time, we started down a path that now has us operating with a full buffer, paying off debt and planning for the future with ZERO money worries for the first time in our adult lives.

But Andrew missed that part. Or at least he was somewhat unaware of it as his last couple years of high school were filled with activities not the least of which was his earning the rank of Eagle Scout. Now that he has graduated he is out on his own, working at a new job and is about to get married. Where did time go?

In any case, he has entered into such a dramatic new stage of life that he has started to ask questions again. Specifically, (thankfully) they are mostly money questions. This time I am more than eager to teach him. I’ve learned a lot about money in the last few years and am armed with rock solid answers for him concerning budgeting, debt, long term planning and more. But even with that arsenal I have to be careful with what I say or how I say it because he can’t help but be influenced by having watched our history of abysmal money management through all those years.

The solution to this quandary came to me quite easily, full disclosure. Without hesitation I will talk to Andrew about anything that we have done, and are now doing, financially. Our finances are an open book as we have banished long standing societal taboos about money talk from our home. In our talks I have widened his eyes more than once as I’ve told him of the stupidity that used to reign as master of our money. At every junction I make it a point to teach him why what we did then was wrong and why what we do now is right.

If the phrase “Teach your children well” were a metaphor it may just mean that in order for your children to learn and grow to become happy prosperous adults then they need to drink from the “well” of your knowledge. If you don’t know, then they can’t learn, so commit yourself now to reading more, asking more, learning more, and when your children ask, don’t hold back, tell them everything.

My overall message about money management to Andrew now is “Do as I do, not as I did.” So far I am pleased to tell you that he appears to be listening, and learning.