When I struggled with money during the 1990s, I had no clue what I was spending each month. I made my financial decisions based on my checkbook balance: If there were a few bucks left, I’d find ways to spend the money; if my balance was close to zero (as in $10 or $20), I’d turn to my credit cards. Where did this money go? If you’d have asked me, I wouldn’t have known.

As part of my financial turnaround, I learned to track my spending. In fact, this was one of the most effective tools in getting me to change my spending habits. Every week, I’d sit down at the computer to enter my receipts into Quicken. Once or twice a month, I’d play with the graphs and reports, keeping an eye on the problem spots. By tracking every penny that I earned and spent, I became more aware of my habits.

But something’s happened lately.

Last summer, I noticed that my discipline seemed to be lacking. Instead of logging my spending every week, I’d often go two or >gasp!< three weeks without using Quicken. At first, this made me fret. “Something’s wrong with me,” I’d think. “If I don’t track my spending, I’ll lose control.”

You know what? I didn’t lose control. Even if I went an entire month without entering my info into Quicken, my spending stayed in check.

Last fall, as I was writing my book, things got even worse. Sometimes I’d go six weeks without remembering to enter data. And then 2010 rolled around. Here’s a shocker: Since doing my year-end numbers in early January, I haven’t logged my spending once. And just last week, I stopped saving every little receipt. (It’s been years since I tossed out a grocery receipt before coming home.)

Some of you may be alarmed by this. A few years ago, I would have been concerned, too. But I’ve actually found that my scofflaw attitude is liberating. Over the past few months, I’ve seen that I’m perfectly capable of practicing conscious spending without logging every penny I spend.

Although I no longer track my spending in detail, that doesn’t mean I’m ignoring my finances entirely. Hardly! I still check my statements every month to be sure there’s nothing goofy. Plus, I double-check to be sure my account balances are continuing to grow. In a way, it’s as if I’ve removed the training wheels and am now zipping around the driveway on only two wheels.

This reminds me a little of my return to credit cards. In 1998, I destroyed my credit cards because I couldn’t use them responsibly. For nearly ten years, I lived without a personal credit card. I was afraid to trust myself. But about three years ago, I decided to take a chance. I set some ground rules and signed up for a single card. Since then, I’ve not only used credit responsibly, but have actually learned that it can make life more convenient.

So maybe leaving Quicken is the next step. Maybe part of the third stage of personal finance is recognizing that my financial discipline has become ingrained, that I no longer need certain redundant systems because the internal systems are working just fine.

Or maybe I’m fooling myself.

I’d love to hear from other GRS readers. How many of you track your spending? What’s your financial situation like? Have you found that you’ve “outgrown” Quicken and Mint and similar tracking programs? Also, I’m dying to know: As my mental relationship with money matures, will I find that I’ve outgrown the need for other techniques that helped me get out of debt?

Sidenote: My wife has never kept detailed records. When I told her about this post, I asked why she’s never kept a detailed spending log, but just made broad notes in her checkbook register. She gave me a look: “I don’t need to track my money,” she told me. “I never spend more than I have.” (Plus, she pointed out that she “pays herself first” by saving nearly 30% of her paycheck for retirement before the money reaches her checkbook.)

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