Confessions of an out-of-control penny-pincher

My near-crippling obsession with cutting costs

I was a pretty lucky child growing up in a suburb of New Orleans. I attended summer camp, went to private schools, and learned to play the piano and dance ballet. With their upper-middle class incomes, my parents were able to provide for me in a way that many families can't.

But while I never knew what it was like to want for anything, my parents did think it was important for me to learn the value of money. Once I became a teenager, they encouraged me to get a part-time job, so I could foot the bill for hanging out with my friends and any shopping excursions. At 14, I got my first gig as a babysitter, moving on to restaurant host and day-care worker during the rest of my high school years.

My paychecks were mine to manage, and I had my own checking account. By the time I graduated, I felt financially independent because I was responsible for all my own spending money.

So I naturally figured I would be able to juggle jobs with school in much the same way once I got to college. But college was a totally different world — and it didn't take me long to realize that "having enough" would take on a whole new meaning.

My path to obsessive penny-pinching
In the fall of 2007, I entered Barnard College in New York City. And although I was a straight-A student in high school, keeping up with undergraduate coursework was decidedly more difficult.

From 9 a.m. to 10 p.m., I attended classes, studied, wrote papers, and managed to sneak in meals. Unlike many of my fellow classmates, my parents didn't give me spending money. They took care of my tuition, room, and board, and plane tickets home, but I was responsible for scrounging up money for day-to-day expenses.

Because of my nonstop schoolwork, I could work only on the weekends. By my senior year I'd held a medley of odd jobs: babysitter, translator, English tutor, dog sitter, house sitter, model, and personal organizer. I never made a lot of money — $200 a week at most — and that didn't go very far in Manhattan.

As a result, I developed some extremely frugal habits that helped me reduce my spending and save some of the little money I was making — but also launched me on a path to a near-crippling obsession with cutting costs.

My groceries and toiletries were all generic brands. I didn't shop for new clothes. I didn't go out to bars or clubs with cover charges. I also looked up campus events where free food was advertised. I even went to a meeting for a campus organization that I was completely uninterested in just so I could take some cookies — that was breakfast for the next two days.

Even when I had a little extra, I felt the need to save it for the weeks when I couldn't find work or didn't have time to work because of my studies. I never got a credit card because I was afraid of spending more than I earned, and I never asked my parents for help because I felt like I needed to be an adult and figure things out on my own.

Looking back on my college years, I realize my stress levels were much higher than my classmates' because — in addition to worrying about grades — I was constantly worried about money.

Why my problem only got worse post-graduation
When I graduated in May of 2011, I landed my dream job at a publishing company. I thought that having a steady paycheck would help alleviate some of my financial stress, but despite my frugal ways, I still wasn't prepared for the reality of living on an entry-level salary.

After taxes, medical insurance, and other payroll deductions — except for retirement, which was a pipe dream at that point — I had $1,600 a month to live on. In some cities, that's doable, but it doesn't go very far in New York. Determined to stay in the city and advance my career, I had to find a way to make that money work.

This meant finding new levels of frugality that put my cheap college habits to shame.

First, there was the little matter of rent. I found some decent roommate situations in nice neighborhoods, where I would have paid between $800 to $1,000 a month. But once I calculated how much disposable cash I'd actually have, I decided the best option would be to rent a room in a not-completely-safe area for $550 a month.

Then I came up with detailed spreadsheets to track every single penny spent. I only allotted money for rent, utilities, groceries, transportation, toiletries, cleaning supplies, and other essentials. Dinner usually consisted of $3 microwavable meals, and going out was out of the question.

I also couldn't bring myself to shop, even when I was sorely in need of a new outfit. I remember showing up to work once in a hole-ridden dress and overhearing some co-workers snickering about me behind my back.

And what little I managed to save always seemed to get eaten up by unexpected expenses — like getting stuck with a $500 "lab fee" from my doctor's office. I was always in fear of the next financial emergency.

My anxiety over finances meant that I lived a pretty lonely existence. I avoided most social situations that involved spending money — it got to the point where I'd only accept invitations from friends who I knew would pay for my dinner, coffee, or drinks. I was upfront about the fact that I was uncomfortable spending money, and most of my friends would say they understood — but deep down I felt like nobody really could.

It wasn't until I met Cécilia that I realized my frugal ways were getting out of hand.

Reaching my thrifty tipping point
I met Cécilia at work, where she noticed that whenever I'd get invited to an after-work party, I'd order the cheapest thing on the menu — or nothing at all. When we started dating, I made her aware that I wasn't making much money, so she footed the bill on a lot of our dates.

Cécilia accepted my cheapness, but there were times when it created tension between us. The turning point for me came when we were celebrating her birthday as a couple for the first time.

For my birthday, she had gone all-out with a night at a hotel and dinner at a nice restaurant. When her birthday rolled around, I was incapable of purchasing a real present, mainly because my cheap mentality had become so engrained in me. My gift? A bagel with lox, because I knew it was one of her favorite foods.

She smiled when I offered it to her, but mentioned later that she would like a "real" present for her next birthday. While she made a joke of it, I could see in her face that she would have liked for me to make an exception to my cheapness for her birthday.

I knew it was time for me to let up on my extreme frugality.

Now that we're married, I haven't completely changed my ways, but I have loosened my grip on money. Cécilia and I have mostly separate bank accounts, but we do have a joint checking account for household expenses. Although I still track all my spending, I also know that splurging on a nice restaurant isn't the end of the world.

To be sure, I'm not saying that being thrifty didn't, and doesn't, have its benefits. A lot of my friends live paycheck to paycheck, either because they don't make much or because they feel pressured to consume — whether it's a $15 cocktail or the latest tech gadget. Many of them have racked up thousands of dollars in credit card debt.

By contrast, I never draw my checking account down to zero, I've started contributing to retirement and I have enough savings to cover myself for five months if I lost my job. I'm never caught off-guard when confronted with an unexpected expense, and am now focused on saving up for a down payment on a home. Compared to other twenty-somethings in New York, I feel like I'm ahead of the game.

But I realized my frugality went from being a good habit to an unhealthy obsession when I couldn't even buy the person I love a proper gift. Looking back, there were times when I could have let myself have fun, make some memories, and allow myself the occasional splurge — as long as those things were the exception and not the rule.

This story was originally published on LearnVest. LearnVest is a program for your money. Read their stories and use their tools at LearnVest.com.

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