This guest post from Anna is part of the “reader stories” feature here at Get Rich Slowly. Some stories contain general “how I did X” 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.

My experience with money is probably the opposite of many readers here. I’ve always had money. I got a generous allowance starting at age 5, and was encouraged to save it. What I’m not sure about is how to spend it. And I definitely don’t want anyone else knowing I have it (which is why I’m posting anonymously).

I don’t come from a long line of family wealth — just one generation of two thrifty people (my parents) who worked steady jobs with benefits starting in their twenties, and kept those jobs for their entire lives. Growing up, my dad told me that our family had more money than others in our relatively poor, rural area. And it was a secret. I shouldn’t tell my friends about my allowance. There weren’t a lot of outside signs of our money — we rarely ate out, we shopped at the Salvation Army and JC Penney, and we got our hair cut (badly) in some lady’s kitchen for five bucks.

We have that at home
Two irritating practices of my father’s brainwashed me into the idea that money was only for saving, not for spending.

The first was the dreaded “we have that at home.” If we wanted a 50-cent soda out of the vending machine, my dad would say, “We can get a 12-pack of soda at the supermarket for $2.50, so each can would only be 21 cents. I’m not paying 50 cents for a soda.” And we would never get that soda.

Same with ice cream: “For the price of that cone, you can get a whole gallon of ice cream at the supermarket.” This was infuriating. If you have kids and don’t particularly care about them liking you but want to save money, “we have that at home” is definitely the way to go.

If we protested with, “But you have so much money!”, the stock reply was “I wouldn’t have so much money if I wasted 50 cents on a soda all the time.” True for many, but considering that my dad managed to save a few million dollars, I’m pretty sure he would have had room for a whole bunch of sodas in the budget.

Spending money like it grows on trees
As we got older, my family started to take summer road trips. We’d bring a cooler, stay in cheap motels, and generally have a great time. Better yet, on vacation, my dad would inexplicably buy us treats like ice cream cones. We loved it, until one day when we were sitting on a bench eating our forbidden ice cream cones and my dad sighed and said, “We’re spending money on this vacation like it grows on trees.” I wanted to throw my ice cream cone in his face.

With that one sentence, my dad made me feel guilty for the entire vacation, even though I had had no part in planning it and he was in charge of all the cash. Later, when I traveled by myself, I did everything I could to save money — to the point of hitchhiking and other things most people would consider unsafe — just to avoid that same feeling of spending too much on a vacation.

Was it worth it?
If you, dear readers, knew the kind of money my dad has given me over the years, you might (and probably will) call me an ungrateful brat. The truth is that I am grateful. I’m grateful to both of my parents for teaching me financial responsibility, how to be thrifty, and how to live beneath my means. And, of course, I’m grateful for the money they’ve given me — or at least, I will be one day when I finally give myself permission to spend any of it.

I never need to worry about whether I have enough to pay a bill, or whether my decision to return to grad school was financially smart. (Don’t worry: I pay for it by working assistantships, not with dad’s money.) But I do have to obsess about whether I’m getting the lowest price for everything.

It took me two years of grad school to come to terms with occasionally buying coffee and studying in a coffee shop, instead of staying at home where I could drink cheaper coffee I made myself! I put myself through bus hassles because I refuse to pay for on-campus parking, live in cheap apartments that always seem to have more annoyances, and only apply to nearby conferences because I just can’t see spending hundreds of my own dollars on academic travel.

My personal savings (which just topped $100,000) have no impact on my spending decisions. I have no level that I would consider “enough” to spend more freely.

Not my choice
While it’s great to have my own earnings and the money from my dad sitting around earning interest, I didn’t choose it. I’m ashamed of having money, and constantly irritated with myself for my cheapskate tendencies. If I could go back, I would have bought my childhood self more sodas and more ice cream cones (in addition to teaching frugality in general), even if it meant having less in the bank.

Money doesn’t buy happiness, or love. The way I came about it, it buys security at the expense of enjoyment. I’m trying to tell myself to lighten up a little — to go out to dinner with friends without worrying about the bill, or buy a shirt I really like even if it’s full price. I’ve become a little more reasonable over time, but I still have a long way to go before I can spend money like a normal person.

Reminder: This is a story from one of your fellow readers. Please be nice. After nearly 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. Photo by Eden Pictures.

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