Haha, this post really took off. For those who have provided the solicited face-punches, appreciate you; for those who have tried defending my silliness - also appreciate you, but I definitely deserve the criticism.
I've tried to answer some of the questions from this thread below. Honestly, the logic (such that there was) doesn't justify the insane spending, but hopefully provides some context if nothing else.
How does someone take a bazillion Ubers for several years and not at least once consider just buying a car??
I had a few people ask if/whether I own a car.
I do indeed own a car, which makes my checks to Dara K even more egregious. (A few astute readers saw I did mention paying for car insurance. Kudos!) I live outside of NYC and commute into the city every morning. Rather than driving to work, I used to take public transportation every morning and evening. Most of these Ubers were taken after a night out drinking (usually $80+ one-way), getting to work early in the morning if the public transport wasn't running/was running behind, or while traveling (which was usually covered by my company. More info below.)
Many of the, ahem, unenlightened don't track expenses closely and thus have no idea how much they spend on transportation. Many don't bother running the numbers to see what's the most efficient mode of transport for their needs.
This behavior is strange to us who can't imagine NOT tracking expenses and thinking long-term.
There were a few questions about how I managed to rack up this much spending without noticing. It was a combination of things for me:
- A fairly sizable income early in my career (thankfully also made it simpler fix the mess once I opened my eyes)
- Poor entertainment choices, like drinking out a few times a week and then taking $80+ ubers home
- A few factors that I'll group into life-sucking job: 1+ hour commute each way, high stress, long hours (frequent 7am starts meant I was hitting the snooze button a lot and paying for it in ubers)
- Probably most importantly: not tracking my spending outside of a few savings/investment transactions that I had automated monthly
Additionally, a lot of the ride-sharing was done on business trips in other cities, so I'd estimate ~30-40% of that total spending was expensed and paid-for by my employer. (I haven't done the actual math yet, but this would be interesting.) Again, this point isn't to defend my spending here: $18K is just as ludicrous as $25K for this category.
As to how I managed to spend this much without noticing: you'd be surprised how easy it is. If anyone wants to replicate (though I'd recommend against it): step 1) don't track your spending, step 2) work a stressful job with decent earning potential, step 3) cope with the stress with poor decisions in other areas, such as going out for drinks. The spending sort of takes care of itself if you follow that three-step plan to a tee.
Now being intentional with my spending was a bit more difficult.
OP, if you use Uber that much and don't already have it, get the Uber card from Barclay - will at least help cut down on the expense if you put all your spending on it.
Going to classify this as: "Are you still spending this much on Ubers??"
The answer is: no. I'd basically cut Uber expenses to zero unless my work was paying for it, even prior to the lockdowns. The $~1500 spent in 2020 was during Jan/Feb while I was traveling for business, so little by the way of my own spending at that point. My last big month of Ubers was October 2019. Dara's getting no more dinero from me.
(Thanks for the recommendation, by the way Ducky. Going to hold off for now, since I'm trying to avoid any temptation.)