The 4 Women I’ve Wasted Money Trying To Become


One of the ideas that’s been hardest to accept in my journey to become totally in-control of my spending is that there is no one item I can buy that will make me a different person. On some level, it’s easy to blame global media and advertising for my subconscious perception as a woman that this lipstick or that blazer will transform who I am, but I know that it’s more than that. I’m someone who has always had an extremely difficult time managing my impulse spending — especially when it’s directly driven by my anxiety — and I know that my own battle with thinking I can spend myself into a person I like more is mostly in my head. Yes, I am a victim of a society that pretends women can put on another persona like a themed Barbie, but I am also someone who is soothed and reassured by spending money.

I think that part of this is growing up financially-insecure, and then living in a town with a very high median income: it was always natural for me to feel like confidence was something I could buy, or that I was just a certain amount of money away from being a person I idolized. So much of our social status as kids and teenagers is dictated by the labels we wear, the places we can afford to go, the luxurious extra-curricular activities we can participate in. And we reward people for having had the ability to do things: on some level, we know that a prestigious university education is a financial privilege, but we usually speak of it in terms of meritocracy. We know that traveling is something that nearly anyone can experience if they afford it, yet we still attach undue moral significance to having been to other countries. We know that many of the things we can choose to do or experience that make us “interesting” are unattainable to much of the country, but we still believe they will transform us.

And this trickles all the way down to buying that one perfect work bag which, despite the fact that the worst employee in the office could have it if they had enough money to buy it, we imagine will imbue us with more Professional Woman Savvy. I fall victim to this all the time, and battle myself constantly over my inability to distinguish something I want and something I trick myself into believing I “need.”

What’s more dangerous, though, is when I manage to convince myself that there is an entire person I could become if I simply owned the right supplies and/or collected the right experiences. At different times and for different reasons, there were specific women I had in my head that I strongly wanted to be (whether this was to impress a guy or get a career I wanted), and I wasted incalculable amounts of money trying to become her. Looking back, I can see each of these eras with a cringeworthy clarity, and all I can think is how much happier I would have been if I’d accepted that I didn’t actually want to be these women at all, and that anyone I stood a chance of becoming, I wouldn’t have had to make a concerted effort to purchase.

So, without further ado, the four specific women I wasted money trying to become.

1. The Prep.

The aforementioned hometown with the high median income was Annapolis, Maryland. Although I was a relatively normal middle-class teen by the time I lived there, I was inadvertently surrounded with the kind of wealth that, looking back, forever distorted my view of what was normal. More people than not around me had BMWs and boats and k-12 educations that cost more than many universities, lived lives free of things like student debt or work-study or having to scrimp and save for extended periods to buy something. And while, as an adult, I can look back and feel truly grateful that I did not grow up with a lot of luxury — I believe that my personal drive and hunger stems largely from the fact that I’ve had to be scrappy — I can also be honest about how much it impacted me at the time.

When I was living in Annapolis, and the overwhelming manifestation of wealth was WASPy, sailing-town preppyness, I all but hemorrhaged money in an effort to imitate it. While I was working at the Yacht Club, for example, I would routinely blow entire paychecks on Lilly Pulitzer dresses and Sperrys and J. Crew tortoiseshell headbands, and many other superficial elements of preppy culture I couldn’t afford. Looking back, not only was this an enormous aesthetic mis-investment — literally none of the things I bought, especially those several-hundred-dollar cotton shift dresses with crabs on them, are something I would wear again — it also was a totally backwards attempt to buy into preppy culture. I would never be preppy: I don’t come from WASPs, I don’t have a college degree (let alone an elite education), I don’t have a sailboat or a waterfront cape cod or a roman numeral-ed boyfriend or any of the other core elements of that culture. (I also have no desire to belong to country and/or yacht clubs, particularly after working for one, but that is a whole can of worms I will not open in this post). I’ll never be Old Money, and I’ll likely never be New Money, either. And no amount of crustacean-motif clothing would change that.

2. The Career Woman.

When I was first starting out with internships during college, I became overwhelmed with this (perhaps not totally-unfounded) fear that, because I was going to a community college and didn’t have a ton of experience in anything, I had to go way overboard to overcompensate and convince people that I was a Professional. I was going between DC and Annapolis on a daily basis at this time, and would often find myself pulling over at some business casual store or another to stock up on blazers, slacks that made me look both weirdly long and stumpy, and enamel-based jewelry that I thought at the time was synonymous with “serious working woman.” I truly thought, and it’s the impulse I fight most to this day, that being professional is something you wear. And while I will grant that there is a basic, foundational office wardrobe that most people will have to invest in at some point, there is also a clear difference between “going on a splurge at Banana Republic because I have some vague professional commitment in the near future” and “planning ahead for a yearly investment-shop in some staples I need for work.” I often tended towards the former, and though I can still slip up with that from time to time, at no time was it more of a downward spiral into a pile of blazers than during that highly-insecure internship year.

3. The Outdoorsy Cool Girl.

Anyone who knows me most likely let out a hearty LOL when they read this point because, lol, I am the absolute antithesis of outdoorsy. There is not enough money in the world to get me to voluntarily camp again, and there is no natural glory I’d ever prefer to see over discovering a new city. I am, and always have been, an urban explorer, and could walk 10 hours straight through urban streets, yet will start complaining at approximately minute six of any hike. That’s just me, and I in no way mean to denigrate people who prefer the great outdoors: live your life and enjoy it, I will just not be there, no matter how many campfire s’mores are on offer. (Unless we’re roasting them over the fire next to the jacuzzi at our chic lodge we found on AirBnb.)

Point being, I am laughably not an outdoorsy person, yet for a brief time that I was dating a guy who very much was, I spent untold amounts of money trying to become one. On our way to visit his family in their mountain summer home, I maxed out my credit card (the one I ended up defaulting on and tanking my credit with) to buy Lacoste polo shirts, expensive hiking shoes and cargo shorts, and other adorable preppy-outdoorsy accoutrements. (Bear in mind, I was trying to be outdoorsy but still obsessed with WASPiness, which his family very much was — hence, the pastel polo shirts, in which I feebly played a few rounds of tennis.) After that trip, we broke up, and I never touched any of those items again.

4. The Parisian.

When I first moved to Paris, I made the crucial error of picking up my then-host mother’s copy of La Parisienne — a guide to Parisian chic, essentially — and devouring it. I didn’t know that said host mother (who is now a very good girlfriend) mostly laughed at it and considered it unattainable, and I took it as gospel. Everything from my red hair, to my still-heavily-pastel wardrobe, to the words I learned to say in an easily-mocked Quebecker accent felt lame and un-chic. I wanted to become Parisian at any cost, and that meant going to fast fashion stores and buying cheap, shitty, ill-fitting versions of the “so typically French” clothes I devoured in that book. I bought them despite functioning on a razor-thin stipend, which often meant entire weeks eating ramen or not buying crucial schoolbooks so that I could get a crappy Breton-striped shirt that would be filled with holes within a few washes.

Thankfully, as I settled into my life there and realized just how utterly obnoxious and unattainable (and vaguely racist) the entire “How To Be A Parisian” genre is, I abandoned this quest to transform myself into a character I’d imagined in my head. I started wearing and being and buying what I wanted, and found that the relationships I formed and the life I lived there were a thousand times more rewarding as soon as I stopped spending money on this Other Chelsea. I may not have been as chic, but I was damn sure a lot more happy.

Image via Pexels

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  • Alexis

    Enjoyed this piece so much Chelsea. Polo shirts were the absolute bane of my adolescence – being petite, with a very large bust that made me a target for plenty of unwanted attention – why on earth did I think a shirt designed for a boyish figure would EVER look good on me??! Lol.

  • Lauren

    #3 makes me so happy. There are dozens of us!

    • Meg

      It’s so true! I will forever be an “inside kid.” My husband knows that my version of camping is a Holiday Inn without a pool.

      • Alexis

        I say the world can be divided into two camps: those who legitimately, without any prompting or as a one-off, own tents. And the rest of us.
        My brother met his wife at a NYE party. When I was chatting to her and she volunteered that she owned a tent and camped regularly, I was like ok well, both of you come here and meet your future spouse.

        • One more girl with a tent

          This is hilarious 😀 And I love it.

  • Declan

    I read TFD everyday and have never commented before. But the phrase “Unless we’re roasting them over the fire next to the jacuzzi at our chic lodge we found on AirBnb” made me laugh so much, I couldn’t resist!

    PS, I tried to be “The Parisian” as little as 2 weeks ago, so I feel you with that one. *Looks over at Breton t-shirt*

  • Violaine

    I love this article. I am trying to think of what I spend money on to become something I’ll never be. All I can think is knowledge (without the discipline…) I would, either out of interest or to impress somebody, buy so many books and things to learn about a specific, random topic, and then obviously find out I invested too much before being sure I liked that thing, and regret it, but still hope that just owning the books would somehow give me a bit of the knowledge I wanted to have. I have booked about Irish history, books and cds to learn Swedish and Korean, lots of philosophy books… Basically I guess I want to be a scholar or a chic intellectual – buying cheap versions of clothes I’ve seen on Joan Didion, and buying books that I don’t actually have the discipline to tackle because I’ve been too ambitious.

    I get the Parisian things but to be honest, as a French not from Paris, most of the “normal” French/Parisian people buy cheap clothes. I think the French style thing is more about the type of clothes than the quality that only the wealthy can afford. I get told I look “so French” all the time and my clothes are cheap as dirt – but it’s all about wearing a few stripes, and then only black, navy blue or grey – no colours allowed – and also, not brushing your hair too often (you don’t want to look like you’re trying) and having chipped nails. And a cigarette with a black coffee. Don’t forget not to smile as well. Voila ! Maybe I should write a book 😉
    Funny thing is, American people often seem fascinated by French style, while many French women (included myself) are in awe that many wealthy, urban American women look so perfect from head to toe, like they come from a magazine – the hair always bugs me, like do you have to straighten your hair daily to have it so straight and perfect??

    So basically no matter who you are or where you’re from, you’re always somebody’s fantasy as well!

    • Kayla Sweeney

      You mean people out there are jealous I get to straighten my hair everyday!?! 🙂

  • jdub

    Ugh I get this. I stressed and obsessed for years about the fact that my parents couldn’t afford to buy me $90 jeans and expensive skate shoes (lol i wasn’t even a skateboarder, but my bf at the time was) for school, and the same ~branded~ clothes everyone had different versions of.

    It was actually super difficult to come to terms with, because all of my friends were these people. But then I started making my own money, and fuck that noise if they think I’m blowing an entire paycheque on pants just because they’re from the skate shop. I bought one expensive top once for myself and that was my “oh wait this is the dumbest thing ever to worry about” moment. No one even noticed, either.

  • Laura

    Honestly, I feel like this topic has been exhausted on TFD. I really enjoy Chelsea’s writing, but there already are so many articles on this site about aspirational spending; I was kind of disappointed to see this subject matter rehashed.

  • Eva Jannotta

    Why is it so easy to get caught up in these “fantasy selves”? Not only do they make me buy things, but they also make me hold on to things that clutter up my life. Thanks for this expose. Very relatable!

    • oneWEIRDword

      Hmm. That makes a lot of sense! I’ve got to think about that “clutter up my life” bit.

  • Isabel

    Yes x 10, esp to the Parisian girl part. I studied abroad in Paris for the spring semester of my Jr year. One of my first matters of duty was to impulsively buy a ‘Parisian’ trench coat at a fast fashion store called ‘Texto.’ I wore it almost every day. After 5.5 months, it disintegrated. But I did buy another one at Zara before I left and it lasted 6 years!!

  • Emma

    This is how I feel about juice cleanses. I’ve spent hundreds of dollars on juice cleanses that I don’t complete.