Ok y’all, welcome to my money blog! I’m going to give you all kinds of ideas on how to save money and spend money well. So obviously, my plan is first to hit you with a list of Major Money Mistakes I’ve made in my life because that will certainly engender your trust. Right? Cool. Let’s do it.

We’re going all the way back to college applications for this story. But first, I need to set the scene and give you some background because I believe a person’s financial background is instrumental to understanding their relationship with money over time. So here goes: I grew up in a middle class family and attended suburban schools where all the teachers described us (to us) as “upper middle class,” which is kind of cute in a weird, patronizing way, like “oh no, we wouldn’t want to describe you as truly middle class because that would be embarrassing.” And I guess some of my classmates were upper middle class, but also a lot of them were lower middle. We were the kind of town where a lot of people pretended to have money – you know, the see-through houses where families could “afford” the house but not the curtains?

Anyway. My mother stayed home with my brother and me for most of our childhoods while also running a successful home-based business. I can still recite the marketing plan 20 years later. She used to pay me $10 to come along with her to her shows and help set up/take down the products (and be SUPER charming with adults who love precocious little girls). It was so fun! I learned a lot about industriousness and making. things. happen. from my mother. My father was your basic white-collar office dweller who never advanced into management. We never had to worry about money growing up – my parents made around six figures together and we lived in low cost-of-living areas. It was the best of both worlds. A stay-at-home mom who went on my field trips and also two full-time incomes. I had so many American Girl dolls and outfits!

Then my parents got divorced and everything changed. Suddenly, all I heard about was money. Money was now a problem. There was never enough. If you’re wondering if parents inappropriately discuss issues with their children in the aftermath of divorces, the answer is YES. Some of it is inevitable when your life changes so much so quickly, but it was rough adding that layer into my relationship with my parents after having never thought much about money before. As the divorce aged, things deteriorated rather than improved. Court dates to fight over child support. Whiny father who started fights about me wanting money (despite me rarely asking for any from him). Accusations. Frustrations. We always had enough of what we needed. But there wasn’t a lot extra. So I started babysitting at 11 or 12, before I was even free of babysitters myself.

When I was younger, I made okay financial decisions. I was always a money-earner, but never a saver. By high school, I was a professional babysitter and dogsitter. Parents would ask my rate and I’d say, “whatever you feel is appropriate,” which yielded $6-8/hour even in the early years. When I turned 16 and got my dad’s hand-me-down company car – a hawt 1996 Dodge Stratus, y’all – my mom told me I had to get a real job in addition to babysitting. I first worked at a Jason’s Deli for a week at $7.25/hour, and learned a LOT of kitchen order codes, like “86”-ing something (a phrase I still love), before taking my talents to a daycare near my high school. It was through that week at Jason’s Deli that I confirmed food service was not for me. Children and retail clothing only, please. So I worked with toddlers at a daycare throughout high school, making $8/hour. The summer before college I added working at J.Crew, which was and still is my homing beacon, also for $8/hour. My time at J.Crew taught me the retail markup on clothing, and now I almost NEVER pay full price for clothing because I know I'm getting hosed. I paid for my own gas and dance lessons, as well as any fun money and most clothes. I saved basically nothing.  Except – and this is a big except – I paid for two (TWO!) trips to Europe….in high school. Not joking. They were through one of those low-cost student tour companies. And I diligently saved every penny I could to pay for those trips and my spending money.

This is where I am most apparently my mother’s daughter. I also make. it. happen. If there isn’t money, I’ll find a way. She has always encouraged me to do pretty much whatever I want, for which I am indescribably grateful. But “Sure!” usually came with a caveat: “if you pay for it.” Which like, cool Mom, what 14 year-old is going to raise $2,000 for a 10-day trip to Europe? I AM, BITCHES. And you know what, I did it. And then I planned and paid for a second trip too! I consistently deposited my little babysitting and Christmas and birthday checks into a savings account, waiting for the day when I’d take it all out to pay for two weeks of European magic. And it was magic. I sometimes think back on that ~$5,000 and how much it would have accumulated today if I’d not taken those two trips, but I do not consider this one of my financial regrets. Four of my future bridesmaids came from that trip (they are also the only 4 humans I still speak to from high school, so, hey…), I experienced a level of independence few teenagers do, and I got to see a big, new piece of the world. Fifteen years later, I still count that first trip especially as one of my most life-changing experiences.

After all that babysitting, somehow, it was finally time for college applications. I had the great blessing of being able to #crush standardized tests and did very well in my high school courses. I accepted a full ride to the well-respected state school where my parents are alums. We’re talking tuition, fees, room and board, and then some, in addition to the prepaid tuition plan my parents had for me. The only financial obligation I had at the end of four years was my study abroad loan of about $4,000.  That full ride was a major gamechanger, because other than the prepaid tuition plan, my parents wouldn’t have been (and were not) able to contribute significantly to my college expenses.

So let’s review: until college, I always had jobs, saved for discrete things, if not “for the future,” and had a killer financial package in place that would allow me to graduate college basically debt-free. Pretty solid, right?

Yeah. And that’s where the mistakes began.

Next time – No Ragrets? Not even a single letter?