I am a Catholic. That means that I pay regular visits to the confession box.

My guess is that those of other faiths do similar sorts of things. I know that people in 12-step programs occasionally “take a fearless moral inventory.” It sounds like it is something along the lines of a whole bunch of trips to the confession box rolled into one.

There are two things about the confession-box experience that just about everybody who goes through it remarks upon. It feels awful going in. It feels real good coming out.

Most money management advice assumes that we are rational creatures pursuing our self-interest in a more or less informed way. The goal of much of what you read in personal finance guides is to help you become a little bit better informed. Perhaps you didn’t understand just how the rules for taking money out of a Section 401(k) plan work. The guide explains the rules, leaving you prepared to rationally pursue your self-interest in an even better informed way.

All of this is fine so far as it goes. To a large extent, though, it misses the point.

It’s obviously a plus to learn about the Section 401(k) rules. The reality, though, is that just about none of us are rational creatures pursuing our self-interest. We are humans. We are haunted by things we fear. We are excited about our hopes for the future. We often tell lies to ourselves to avoid looking at the things that frighten us and to trick ourselves into believing that our hopes for the future have a better chance of coming true than they really do.

We are liars by nature. A more charitable way to say it is to say that we are rationalizers by nature. Either way you say it, it comes to the same thing. We don’t face truths straight on. We kid ourselves. What a conundrum!

We hurt ourselves when we kid ourselves. I don’t believe that God invented confession so that he could enjoy seeing my humiliation when I have to report my sins to a priest. I believe that God invented confession because he loves me and because he knows that I need it if I ever am to find the right path.

By “the right path,” I don’t mean just the path to heaven. That’s the big one. But I believe that God loves me enough that He wants me not only to be with Him in heaven but to experience a little bit of heaven through the good experiences I have here on good old Planet Earth. God wants me to figure out what I need to do to retire early. God wants me to figure out what I need to do to be able to spend my time doing fulfilling work. God wants me to figure out what I need to do so that I can afford to take my boys to Disney World.

God actually does care about that stuff. And he knows just what I need to do. He would make a great money advisor. He’s got funny ways, though. It’s not like Him just to whisper in my ear the saving tips I need to know about to make these good things happen. God is like one of those professors I had in law school making use of that darn Socratic method thing. He wants me to figure this stuff out for myself.

He wants me to guess. Tha’ts what it comes down to. He knows the answers, but He’s not telling. I don’t know them, so I have to guess. It’s frustrating at times. Still, I have the sense that that’s indeed the way He has set things up.

One of the purposes of the confession box is to help me make better guesses. I mess up. You’re supposed to learn from your mess-ups. I don’t want to learn from my mess-ups, I want to forget about them as quickly as I can. I do this examination of conscience thing that you have to do before you go into the box, and the mess-ups are recalled to my mind. Then I learn from them.

Maybe.

The Section 401(k) stuff is not what matters most. What matters most is developing the habit of being honest enough with yourself that you will make good money allocation decisions, that you will spend when spending is the way to go and that you will save when saving is the way to go.
You learn this from experience. We all have lots of experience spending money. We all have lots of opportunities to learn.

Most of the time, we fail to take advantage of those opportunities. We mess up. We don’t want to think about it. We want to cover up our sins.

It’s a sick feeling you get waiting in line to go into the confession box. It’s not fun.

The money management equivalent is the feeling you get when you have to record in your budget-binder some dumb thing you wasted money on, knowing that your wife (or husband) is going to see it and probably even ask you about it. Who needs this?

You need this, you messer-upper you!