This guest post from Louisa Rogers is part of the “reader stories” feature at Get Rich Slowly. Some stories contain general advice; others are examples of how a GRS reader achieved financial success — or failure. These stories feature folks from all levels of financial maturity and with all sorts of incomes. Previously at GRS, Louisa told us what it’s like to have even better than enough.

“May you have a prosperous New Year!” the saying goes. Although I’ve never been poor, some of my lifelong habits would certainly make you wonder. Until recently, my sense of financial well-being never matched the contents of my wallet. Now, I do feel a sense of prosperity, and it came about only because of gritty, purposeful change on my part — the kind of change we talk about as we embark on a new year.

I’m naturally frugal — or is that cheap? I’ve been called both. In either case, I don’t have trouble staying within my limits. I’m someone who can order every airline credit card that offers 25,000 frequent flyer miles, and stash the unused cards in my desk drawer while I happily fly the friendly skies. My husband teases me that while I love to earn, once I actually have the cash, I have little desire to spend it. (He spends it for me!)

But the downside of my particular brand of frugality is the stinginess that comes with it. I’m not saying this is true of all frugal types, but generosity isn’t my strong suit. I’ve been working on this “issue” (as we say these days) for awhile. Over time, I began to sense that before I could find my generosity gene, there was another step I needed to take.

Coming clean
I have a long history of stealing food from supermarkets. I started as a teenager in the Sixties. So what? Many people steal during adolescence, right? Yeah, but I only stopped a few years ago, and I’m, um, 59.

I used to open a package of oatmeal cookies in a supermarket, eat a handful, then hide the unfinished container on the back of a shelf behind other products. I snatched food from the bulk bins — and not just the occasional grape. I’d hide fat mounds of chips or dried figs or sesame sticks in my hands and munch on them as I wheeled my cart around the store. Before I left the supermarket, I’d go back for more — grabbing a few handfuls, quickly, stealthily, before an employee could catch me in the act.

Strangely enough, until a couple of years ago, I never called this “stealing”.

Now I belong to a 12-step program, and one of the steps says to “make direct amends to such people we had harmed wherever possible, except when to do so would injure them or others.” After many long conversations with my sponsor, I decided to refund the money I owe for the food I’ve taken. Some of the stores are located in other parts of the country (indeed, the world), or may not even exist anymore. So my efforts have been imperfect. But I’ve tried.

Doing the math
I calculated estimates for the amounts I owed, and took bills of $30 or more to the store owner or customer-service manager. They didn’t always make it easy for me. Sometimes I’d find myself standing in the business office, fumbling over my words, wondering how to explain my odd request, and they’d interrupt me and say, “Look, don’t worry about it. We assume some sampling, it’s part of our pricing structure.”

“Yes, I understand,” I’d say, “but unless it’s too much trouble, I’d appreciate it if you’d accept my money anyway.” I knew it was the right thing to do for the stores, but I was only partly doing it for them; ultimately, I was doing it for me, so that I could walk around like a regular person and not feel like a thief.

Yes, it was awkward, but for the most part I was at least talking with strangers — except in the case where the store was actually a client of mine. I had given management seminars to their supervisory staff. I saved that refund until the end. But as my sponsor pointed out, the goal of this exercise wasn’t to make me squirm and feel as yucky as possible. I didn’t need to humiliate myself and make myself talk to my immediate client. In the end, the staff member I spoke with didn’t even ask my name.

The bulk of the stealing I did involved food. But I also occasionally snuck into the back entrance of a health club so that I could work out without using up one of my day passes. I refunded the health club, too.

Personal impact
After returning the money, I felt physically lighter, like I’d lost a few pounds. And I felt lighter about money, too. Which was odd, since after refunding, I had less money than I’d had before — not huge amounts, but still somewhat less. This would have once made me feel anxious, yet now I felt more relaxed.

In exploring this with my sponsor, I realized that for many years I’d had an underlying belief that the world owed me. Because of this, I felt like I didn’t need to abide by the same rules other folks did.

Note: Louisa’s not the only one to have experienced this feeling. Dostoevsky’s classic novel Crime and Punishment is all about a man with the same point of view.

Why did I have this belief? Good question. In my 30s and 40s, I spent many hours in therapy exploring why I felt “owed.” I vaguely remember blaming the usual suspects — my mother, my father, my childhood. But even after all that therapy, I couldn’t tell you today where exactly that belief came from, and frankly, I don’t care anymore. These days, I pay attention to that attitude when it kicks into gear, but happily — maybe because I no longer steal — I don’t feel it much anymore.

A work in progress
Since repaying my debts, I’ve noticed that real opportunities for generosity show up often. For example, I frequently visit a neighborhood coffee shop and read the daily paper from the stack. I used to bring my own mug and teabag and pour myself hot water from the insulated jug to avoid paying $2.50 for a cup of tea. Recently, I thought about all the times I’d sat at a table without contributing. I approached one of the owners, whom I knew. Handing her a $20 bill, I said I’d like to give her something towards my use of the place from time to time. “Great!” she said. ”That’ll help pay for the wifi.”

It’s amazing how good I felt that whole day. I was free! Free to hang out and read the newspaper, without feeling sneaky. I’ll give her another $20 down the road.

My niece graduated from high school this year. I worried about whether to send her a graduation check, because I couldn’t remember if my husband and I had given her older sister and brother checks when they graduated. Back then, I was definitely cheaper. Was it fair to gift her and not the others? I finally decided, whatever happened or didn’t happen before, it was better to err on the side of generosity. I wrote the check.

These may not sound like big steps to some of you; I’m still a work-in-progress when it comes to generosity. But my heart is open and I want to be more generous. Maybe that’s the biggest change. The darker side of frugality gets lighter with every step I take.

Reminder: This is a story from one of your fellow readers. Please be nice. After more than a decade of blogging, I have a thick skin, but it can be scary to put your story out in public for the first time. Remember that this guest author isn’t a professional writer, and is just learning about money like you are. Henceforth, unduly nasty comments on readers stories will be removed or edited.

This article is about Frugality, Psychology, Reader Stories