The List of Women I’ve Wasted Money Trying to Become

The List of Women I've Wasted Money Trying to Become

This is a guest post from my friend Chelsea Fagan, founder of The Financial Diet. TFD has quickly become one of my favourite sites because of the refreshingly honest stories and opinions they publish. I finally got to meet Chelsea and Lauren at FinCon, and am excited to continue our conversations when I visit NYC next month. If you want to learn more about Chelsea, I would also suggest listening to her interview on the Real Talk Radio podcast.

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 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’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. 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, 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.


  • I think we are all guilty of trying to be someone we’re not at some point in our lives. And spending(wasting) the money doing it. Letting go of the guilt of all that money gone is just as important as realizing we are who we are and we love who we are. ❤☕

  • Thanks for the great post, Chelsea, and the brutal honesty. It can be hard not falling into that trap… Marketing can be so influential! I know I’ve definitely been there, wanting all the new and nice things especially when I see my friends have them. It’s hard not to start thinking about why I can’t also have that stuff and realizing it too late that I’ve blown the budget.

  • I too was the not-so-rich kid in a high school where my classmates got brand new Mustangs for their 16th birthdays, crashed them, then got the next year’s models.
    I couldn’t compete with their social status, but I tried. I even tried to be all of them at the same time. I didn’t want just one cool backpack or sweater or pair of shoes, I wanted each cool thing that a friend had and didn’t realize that even the cool kids didn’t have twenty of everything.
    Of course the stuff I got was never quite right and didn’t make me cool. When people reminisce and daydream about being 15 or even 21 again, I can’t share their enthusiasm. I’m just dandy being 35, thankyouverymuch. Life as me is better than it ever was trying to be someone’s clone.

  • I love that you became aware of this expensive game! I’ve played the same game so many times, myself. (My girls were punk, emo, earth mama, athletic guru, and minimalistic chic.) Laugh if you want! It seems ridiculous now that I’m aware of it, but no natural and so convincing at the time. Inspired by Cait, I gave up buying clothing for a year. Now that the ban is officially over, I still have to fight those urges. Thank you so much for sharing your thoughts on this! Hopefully we can change the culture to realize the absurdity of shopping for our identities.

  • Other Chelsea sounds a lot like Other Jenn. Going into the holiday season (9 more Saturdays until Christmas), this is exactly the message I needed to hear. Especially as those “Parisian” scarves that will be on sale, and the ballet flats, and the work-out gear that I didn’t use all year and now need a larger size in…

    I recognize myself as the anxiety spender, and I’m now tracking every purchase and the feeling behind it (Thanks Cait!). Sometimes it’s nice to hear you’re not alone.

    Financial peace is the ultimate goal, and saturating myself in these positive messages are helping me get back on track.

  • What a frank and funny post. I think at one time or another we have all done this in hopes of being that elusive person. My motto is, there will always be someone richer, prettier and smarter than you, so just be your best self! ;)

  • Hi Chelsea, Greetings from Baltimore! It’s so rare to read posts written by fellow-Marylanders. :) This post is EXACTLY what I needed in this moment. I never thought of my desire and spending (past and present) was out of a desire of “becoming” something I wasn’t. Creating that perfect capsule wardrobe or a certain kind of organizer or planner has been a money suck. I’m not in debt financially from it, but I am in debt emotionally from it. I am guilty of #2 and #4.

  • This is so true that we think we can dress up & play the part of someone else. Meanwhile we should be focusing on living our own best life!

  • I can’t relate to the “women I want to become” but I have bought many many things thinking I would become the person I want. So many things make us think that we can just spend money and change ourselves, become more fit, more “cool”, more popular, more happy. The truth is that we have to make changes internally and the rest will come.

  • I really relate to this article. For me, it’s the “adventurous/outdoorsy/traveler chick”. You know, the one who never says no to an impromptu backpacking trip, who pulls off a “just off the plane” look yet still always looks glam, who seems to spend every weekend hiking up mountains or through national parks and has an apparently endless amount of vacation time to travel to Europe and Asia. That’s why I had to laugh at your description of your failure to become the “outdoorsy” type, because at some point I too had to realize that I’m just not adventurous. Travel is great but I’m a homebody and an introvert and I just don’t have the energy or desire to be in go-go-go mode all the time. And that’s okay!

    I find it interesting that being outdoorsy and adventurous are idealized for being experience-based rather than materialism-based yet, as we see here, they are just as susceptible to the influences of marketing and consumerism as being a preppy or a careerist. Spending money on an image is still spending money on an image, whether you spend that money at Ralph Lauren or REI.

  • Oh jeez. If I added up all the $$ I spent trying to impress women by being someone I’m not between the ages of 16 and 31, you could probably make an annual IRA contribution out of all of it. There’s probably Four figures in online dating subscriptions alone.

    And considering I continue to be single, and for the most part in a perpetual manner , I’d say it probably wasn’t the greatest of investments. :D

    You live and learn though!

  • It’s not just women, I’m sure men can fall into this trap just as easily. We can all waste money to try to become the ideal image that we have in our mind. The key is simply not caring what other people think about you and be comfortable with who you are.

    • Tawcan

      Something in your post has made me wonder about “being who you are”. Do you feel as though you have found the real essence of yourself? I know that I have done my own versions of Chelsea’s archetypes, and I have been more content since I largely walked away from that way of life. But when do you know that you’ve uncovered “the real you”? I wonder if I even have a fixed (but capable of change!) real me in there…

      On a lighter note, I saw a mug recently that said

      “Sometimes, telling someone to just be themselves is the worst advice you can give them.”


  • Oh…the tortoise shell J Crew headband…how I remember thee…how I tried to rock you and a ponytail simultaneously…how you would not stop pinching my head and wound up at Goodwill…

    I laughed out loud through so much of this. I can relate. I like wearing jeans with t-shirts and wedges. I have wasted thousands on other items to try and have a different persona…Live and learn, right??

    • I nearly yelled with laughter and recognition: those bloody headbands always gave me a headache too, or else just slid off. Either way, I looked like a demented Alice in Wonderland crossed with a good old fashioned pillock.

  • Hi I’m a Brit and I absolutely loved this post – although I did just have to look up Lily Pulitzer (crustacean motif clothing made me amused and curious!) and I’ve heard the term wasp before and didn’t realise it was an acronym (I am so much the wiser for reading this article – and Googling!)
    The Paris stuff really made me chuckle too. My French friends are cool (in attitude and the way they dress) but they rarely wear any labels and don’t actually have a lot of clothes (quite minimalist) – it’s nonchalance that makes them so, er… French!
    And by the way, from one red head to another – people are dead jealous of our vibrant tresses. Leave your locks as they are :o)

  • I have so been there! For so long I would buy shoes and clothes for the life I thought I wanted to lead but didn’t actually live. It’s taken a long time for me to be realistic with myself, and even now, sometimes I struggle with it. It’s just one of those things that takes practice – one day we’ll get there!

  • This is such a funny post! I think this kind of experience is part of the growing process though, figuring out who you are and what you wear is an exte nail way of showing that. I’ve always been pretty poor but was raised in a rich area so I’ve learned to make thrift shopping my best friend.

  • Holy cow was this relatable. “Cringeworthy clarity” was spot-on. We already know the societal pressures of being a woman and having the “perfect” appearance are enough. Add in being a young woman and figuring out what the hell you’re doing just makes it worse. I had the prep period, the punk period, and the uber professional woman period. It’s all about finding yourself, and I think everyone has to go through that phase. That being said, you’re right that the financial impacts can be felt long-term. I still struggle with avoiding fast fashion and embracing what I actually like. I can enjoy something from afar but not purchase it if it’s not my style. It’s one thing to try something new out of your comfort zone and another to try to make an entire image happen when it’s not your true self.

    Thanks for sharing!

  • I think all the ladies play dress up. There is a fun and innocent aspect to it sometimes. Like being happy to have to dress up as a NYC career girl for work once in a while. Or wearing an elaborate dress on Christmas Eve with my (immediate) family, while they all roll their eyes at me. I know my down deep subconscious fantasies about living in ye olden times weasel their way into more shopping choices that I care to admit. But yes, it’s those moments wheh the darker aspect of this comes into play, where you are trying to make your life different with the things you buy, or to be someone else, or to feel better. None of those things can be bought at Banana Republic. But a money-induced depression definitely can…

  • This post really hits home. All this time, I was spending money on my imagined other selves as well and ended up defaulting on 4 credit cards. I never knew this was the case before. But after coming across minimalism and blogs like this, I am starting to learn to love the real me. I also imagined myself a Parisian, a savvy professional woman, a scholarly bibliophile, a know it all. But clearly, I know nothing, even after having bought hundreds of books. I need help. And everyday in small ways I receive help in blogs like this. Thank you Cait and Chelsea.

  • I am floored to see how many of you share the same struggles that I do…and that this was even a struggle for me. I didn’t realize I had this problem. I actually have five images I have tried to maintain: Trendy Girl, Minimalist Girl, Earth Mama, Outdoorsy Adventure Girl, and Pretty Mom. Constantly rotating between the five has cost me many hours and dollars sorting, donating, buying, and then doing it all over again…sometimes even rebuying some of the clothes I had sold to Goodwill!

    I struggle because I am an outdoor adventurer…my line of work has me outside for weeks at a time in the summer, in the middle of nowhere. But my predecessors and those that pioneered the field of geology did not have Columbia or whatever…they wore what was available and the focus was on warm, cool, dry, not maintaining a certain image. The women actually were out hiking around in their long dresses! No gear for them for sure!

    Thankfully I haven’t maxed my card yet or gotten myself into credit trouble, but my frugal husband has watched me swindle all this money for so many years now and I know he struggles with my ever-changing image and required spending.

    It all finally culminated recently when I spent more money than I care to admit to myself even on maintaining the Outdoorsy Adventure Girl image. REI, Columbia, North Face, Patagonia…I never saw myself as a brand person just because I don’t shop at JCrew or Abercrombie but I was so wrong. Brands are brands, and money is money.

    Social media is powerful and while I accept responsibility for my actions, maybe following some of these pages that show cool kids doing cool things in cool places all the time…and wearing those cool clothes…well, maybe that isn’t a good idea for me. So when I am anxious or having a monent of weakness, I can look at something that reminds me it is okay to be just me…and that being on some mountaintop in the latest technical gear isn’t going to solve all my problems.

    Thank you Cait and Chelsea, for sharing your experiences. Your blog posts help me shed light on a problem I have struggled with now for two decades.

  • I loved reading this post! For me, it’s not so much about clothes and look but about my house and the things I own. My financial situation (being sole provider to my family of 3) is forcing me to have a new look at what’s important and not and what makes our home a home.

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