The 6 Dumbest Purchases I Made In My 20s

If you have followed our site or channel to any reasonable degree, it’s unavoidable by now that you know about my dumb spending history. A big part of the reason I initially started this was to hold myself accountable because, when left to my own devices, I had a tendency to spend in a spiral — making a bad decision, regretting said decision, feeling like “Well I’m fucked anyway so why not keep spending?,” and spending even more. (If you, like me, notice the not-insignificant connections to the kind of relationships we have with food, you’ll understand why I initially decided to title my blog The Financial Diet. Moderation is key, bingeing is always a bad idea, and you are free to change your habits any time, no matter how bad you were before.)

Anyway, all of that to say that I was someone who was deeply irresponsible with money, but specifically with spending. Whether it was the daily iced latte on the way to the office (largely because I loved the way it looked and felt to carry that Starbucks cup every day to my first internship), or it was the series of overpriced clothing items and accessories that I justified while earning minimum wage because I wanted to dress myself into being a better person, my life until the age of roughly 25 was peppered with truly idiotic purchases that left me feeling frustrated, immature, and as though I would never reach my larger goals.

I failed to make the connections that a) every purchase we make, every money decision, plays into our larger narrative (not just the big ones that we really notice), and b) it is more important to truly confront the reasons behind your spending patterns than the raw numbers themselves. Unless we address the insecurity, anxiety, boredom, and all the other myriad emotions that underpin our spending habits, we’re doomed to be confronted with a bank statement at the end of the month that feels like a punch in the face, half the time because we can’t even recall what we bought in the first place.

So to that end, in this week’s video, I explored the six dumbest purchases of my twenties, why I made them, and what I have learned from them.

Image via Unsplash

  • Julia

    I think the link you posted to the video may have had a “play from” value in the link — it started near the end for me, in a section talking about pots and pans.

  • lazuliz

    I purchased a car off of craigslist right after I graduated college that my boyfriend at the time ‘highly recommended’ because his stepdad used to work for the company. Too bad I didn’t check to see if the car had air conditioning! ughh. I was so nervous being in someone’s house and desperate for a more fuel efficient car for my commute that I wanted to buy it and get out of there. It was also a manual that I didn’t know how to drive! I burned out the clutch learning to drive it in the first 6 months. I kept that car for over 6 years and hated it every day in the summer. But hey, at least I can drive a manual.

  • lateshift

    Sorry, but there is so much I don’t understand about some of this “advice.” SO MUCH.

    –first off: hold up – they have international relations as a major in *community* college? for god’s sake, why? I could understand taking that at a high-ranked 4-year college…there aren’t a ton of jobs in that field that pay well, but the ones that do will hire from a select shortlist of good programs. But at a low-ranked school or a community college – seriously, what’s the point? You won’t learn anything, because the quality just isn’t there, period. (that’s not elitist. That’s factual.) No one in a position to hire will respect the degree, even if you get it. And you won’t have any actual practical skills, which is the whole point of community college to begin with. THAT was the actual “dumbest purchase” there.

    –why can’t you sell the designer coat? (“because it was a gift” isn’t a reason). Even if you got just $50 you used to buy a coat you wear every day: how is that not worth it?

    –how on earth is it possible to not understand the idea of public transportation, no matter where you grew up? You’ve been to Disneyworld…you can’t drive your car inside the park, so you hop on the monorail to get long distances from place to place. It’s the same damn thing. Literally. No difference at all. (I will never, ever understand how anyone could fail to make that connection.)

    –You learned the wrong lesson in Williamsburg. It’s so ridiculously isolated – the most difficult-to-reach “office job” neighborhood in the city, by a lot – so it’s pretty much the only expensive neighborhood in the city it DOES make sense to live in if you work there. There are less expensive parts of Williamsburg, and there’s Greenpoint, and while they might be slightly pricier than elsewhere, living further away would cost you AT LEAST an hour a day in commuting…and that’s assuming nothing at all ever goes wrong with the commute. That’s two full days’ worth each month (measured by waking hours.) Nearly ONE FULL MONTH each year. And things will go wrong all the time, so you’ll be taking cabs, which erases the cost savings.

    So basically, living in the area when you worked there was your second smartest option. But the smartest wasn’t to live further away…it was to get one of the many, many, many New York jobs – the overwhelming majority – that aren’t located in the single most inconvenient commuting neighborhood in the city.

    (I’m not even going to touch the whole “handing your money over to the first broker you randomly saw on the street” thing, because I’m not sure how someone who would do that at any point in their life, no matter where they grew up, and has no academic business credentials of any kind, could possibly think their skill set lies in giving other people financial advice. So I won’t pull too hard at that thread.)

    • Anon

      Which ones in particular?

  • Mel

    I have a terrible story about failing to measure! Years and years ago I needed to furnish my shiny new apartment already so my friends could come over and not mock me forever for having nothing for them to sit on, so I picked up some furniture on craigslist. I actually lucked out and used that stuff for years. The problem was that the couch did not fit in the elevator. We tried, we really, really tried and it just would not fit. I lived on the top (4th) floor and my friends and I had to drag it up all those stairs and then down them again when I moved out. Never again!

    • Please tell me you did the pivot scene from Friends.

  • skish20

    Thank you so much for this! I am absolutely terrible with money and I feel like, now that I’m in a real long term relationship, I know my habits are hurting someone that’s not just me. I’ve been trying to improve, but have seen some really bad setbacks lately (binging). I really want to change, reading your posts makes me feel it’s possible!