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Live alone -- no roommates and no renting out part of the home.
I do. Although it is a studio. However, for the same price I'm paying, I found plenty of 1 bedroom apartments in the same location. It's not in an area with much crime.
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In a major city (for the sake of simplicity a city that can support at least two major sports teams MLB / NBA / NFL / NHL).
Check.
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Actually live in the city somewhat near the core and not out in the fringe or in a burb. Own a car that is less than six years old.
Check.
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Do something fun that involves leaving the house at least five out of seven days. Dress so as to not look embarrassing.
I definitely dress so as not to look embarrassing. Since I'm a student, I probably only go out 2-3 times per week. Aside from that, I do eat out just about every day. With an extra $10K-$20K a year, I could definitely leave the house everyday.
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Be able to buy small stuff when you have a craving without having to fret over it.
Check.
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No one is arguing that you can't afford it sometimes just not with sufficent frequency for someone who has 24 hours a day 7 days a week to kill. Affording a six pack every week or ten days is very different than being able to afford beer 3-4 times a week.
True, but it's not that expensive to buy beer and a lot of restaurants are not that expensive. It wouldn't be a lavish life, but it's far from isolation and poverty.
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The last two days have actually been a good exercise for me in understanding what life would be like for our hypothetical individual. I offered to help out with a project and as such I have been trapped in a light industrial / business office since Friday. I can leave but only for 15-20 minutes at a time so no restaurants, no clubs, nothing that even comes close to being fun. I had $300 on me Friday and I have less than $80 now and I did nothing other than kill time while watching over a machine. People who think they can live off $30k while paying for the staples of life and filling up about 100 hours a week of dead time are on crack. Unless you are happy watching TV, screwing around on the internet, and playing video games for the majority of your life it can't be done.
I think it's understandable that you spend a lot more than our hypothetical person. You've already said you live in a really expensive area (even more expensive than a lot of major US cities it seems). Also, you have a lot more money that $30K a year, so you're accustomed to dropping a good amount of money on a regular day. That's awesome Henry, and I hope to be able to do the same in 5-10 years.