I love saving money. Growing up, I never had a traditional allowance, nor was I paid for getting good grades. My brother and I could earn a few bucks by mowing the lawn or putting the dishes away, but sometimes we did those things for free, depending on my mom’s mood. My payment for grades was the feeling of accomplishment when I got an A, and of disappointment when I got a B. Getting a C or lower was not even an option in the Oliver household.


Actually, I remember my brother once getting a C in English (which was a fluke since he’s literally the smartest person I know), and that was a dark day. I vowed to never let that happen to me…until senior year Calculus, which turned from “I want to really understand this” to “A C actually sounds pretty good right about now.” My father, who owns a sweatshirt that says “I <3 Calculus,” wrote his own calculus theory, got a perfect score on his SATs, graduated from high school at age 16, and considered a year of studying at Caltech a “fun gap year” until going to the Naval Academy and graduating academically #1 in his class (I’ll stop there, because his accolades literally never end), was very upset to realize that I didn’t inherit his love for mathematical formulas. At least not on that level…I enjoyed math to an extent, but not an “I’ll study math and engineering at a top university for a year at age 16 just for fun” extent.

I got a little off track in terms of the grade-reward system in my household, but all of this is to say that money wasn’t used as bribery or rewards throughout my childhood, and it certainly won’t be used that way when I have kiddos. Money was used as it should be: For food, housing, clothes on my back, and activities I enjoyed (horseback riding, ballet, musical theatre…to name a few.) I was well taken care of, but the thought never crossed my mind to spend money on superfluous things, which I am truly grateful for as an adult. I’m sure it’s the main reason I’ve avoided debt, aside from the privilege of being put through college.

I was so oblivious to the “big spender” lifestyle that I remember once commenting on a girl’s Sketchers in front of my mom when I was 13, saying “Oh I love those. I’ve wanted those for like, a year.” I truly wasn’t saying it to ask my mom to get them for me—I was just making an observation, and then kept on walking. My sweet mom stopped, put her hands on both my shoulders, and said, “Sweetie, if you want something that badly, especially something like shoes, which you need on your feet anyway, you should tell me!” And just like that, she took me to Journeys and I got my hands on the pair of platform Sketchers that would come to haunt me whenever I see pictures from 2000.


As you can see, it’s not like I was neglected. I just never developed the concept of buying something just because you want it. No, you buy something only if you need it. Made sense to me!

Once I was old enough to drive, I was old enough to get a job and pay for gas. That’s just how it worked. My parents were kind enough to buy me a perfectly good used car and pay for my insurance, but I needed to scoop ice cream at Coldstone Creamery a few nights a week if I wanted gas for this perfectly good car to get around. It was a lesson in responsibility, and in seeing the rewards of hard work– this time through money instead of grades, teaching me that money is something you go out and get for yourself. (Don’t worry, growing up, I was still given money to go to a movie…and a car…and a horse…and a college education. Clearly I was given more than enough, but just not in forms that made me think money was simply green paper.) So, at age 16, I got by by singing the Flintstones theme song for tips like a boss.

Coldstone, here at coldstone 
We’re a scooper dooper family 
When you eat our icecream
We’ll sing in perfect harmony

Ah, the good ole days.

In college, I was given $30 a month for outside of school expenses (gas, food, shampoo, anything). I was not expected to work, and clearly, I was also not expected to drive away from campus very often. I did not get any food money, because I had a great meal plan. Why would you go eat at Plaza Azteca for $10 when you can use your food points on campus? Honestly, it wasn’t that bad. I still made wonderful friends and memories.

I will admit that the first time I had extra spending money, I went a little nuts. It was fun and new territory to be able to buy a shirt I liked! As a full-time singer at Busch Gardens theme park, I made a substantial amount of money, and had no real bills. I probably should’ve saved all of that, but my savings account was already pretty impressive since I’d not spent a dime of birthday money I received from my grandparents every year since I was born. My Busch Gardens money went to weekly shopping sprees at Forever 21, and more Captain Morgan and Diet Cokes than I care to remember. I even took my friends shopping with me, buying them clothes and basically throwing dollar bills around like I was Oprah.


But that only lasted for about six months before I realized that I was about to graduate college and probably needed start being a responsible adult with my income. Hey, at least I was generous.

My knack for living frugally came in really handy when I moved to New York a year after I graduated from Christopher Newport University. My rent was $750, to share a room—not an apartment, a ROOM—with a friend, in a two bedroom apartment that housed four people. The living room was cut in half with a partition to create a third “bedroom.” Ah, New York. I made about $300 a week when I first moved to NYC while working as the assistant to a woman who owned a microdermabrasion soap company. I got this job by meeting her on an airplane, and she said “come work for me in my house.” I can truly say I’ve lived through some very interesting job experiences in my lifetime.

With over half of my income going straight to rent, I had to be very careful with the rest of my money. No cab rides, ever. Subway only. No eating out. Definitely no drinking out. Eventually, I got my awesome job serving tables at Bond 45 and made enough to socialize, but that took me about 6 months. And another six months before I could afford to live by myself in a studio apartment. (Before the studio, my roommate and I had moved into our own 1 bedroom apartment in a, uh, how do I say this…very culturally stimulating area in Washington Heights. Bed bugs included.)

I could go on and on about ways life led me to be very good with my money, but we’re almost 1,000 words in at this point, so I think you get the picture. I’m 28, and while I’ve lived in some of the most expensive cities in the world, I’m not in debt, nor have I ever gone hungry. So that’s a feat.


The main takeaway from all of this backstory is that being “good” or “bad” with money has nothing to do with the money itself. It has to do with your perspective on everything that costs money.

You have to be willing to invite friends over for a glass of wine since you can’t join them for brunch on Saturday. You have to be cool with not wearing trendy clothes, because it doesn’t cost anything to wear clothes you already have in your closet from 5 years ago. When you do go out to eat, you don’t choose what looks the best on the menu, you choose whatever’s the cheapest on the menu. You take into consideration gas money, and walk or ride your bike whenever you can. You get a library card and don’t pay for cable and have wires running through your living room into your computer so that you don’t have to pay for wifi (at least, if you’re me in NYC).

As for the money itself, you consider gift money something to be saved as insurance for your future, not as extra spending cash for whatever you want right now. You check your bank account every day and make it a game with yourself to get the number to increase by $1,000 in the next two months.

Eventually, the extremity of your choices will [hopefully] shift. As you get older and make more money, you can start enjoying the “things” of life a little more freely. Or maybe you’re super lucky and made plenty of money as soon as you got a job, so you never had to pinch pennies. That’s great! But it’s still much safer to view everything– clothes, food, wifi, travel, gadgets, etc.– as luxuries, not givens.

Even the most financially set people I know (i.e. rich) always watch what they spend, and don’t buy just anything they want. Or if they do, they look for deals and sales. There’s something to be said for always being slightly careful with money, because it gives you flexibility when you really need to do something. I was always able to move cities when I wanted, because I had enough saved up to cover the cost of moving (though I sometimes cut it close). I’ve never even lived paycheck to paycheck, because I always keep enough in my checking as a buffer. To me, that is worth saying “no” to certain social events or dressing a little less “cool.”

So, if you find yourself wishing you were better with money– don’t think about the money. Think about the things you want to buy with it, and remind yourself that you probably don’t need most of it. In a “yes” culture, with social media making you feel the need to keep up with everyone around you, it’s easy to think most of what we have or do are “necessities,” but they’re not. You’ll be just fine if you skip a few events and trends, I promise.