I managed to save money without much issue, and I moved out of that place with $12k cash.
It was a very good time in my life, probably the best time. I think you maybe have a different idea about what makes you happy--those "frivolous pleasures." Simpler living is not the same as asceticism.
I am in a position in my life now, having bought a rural property ($60k for 40 acres and a home), where I could live for much less than I did at that time. Some things I find rewarding there are raising a few animals, gardening, hunting, camping on my own property, woodworking in my small woodshop (hand tools are cheaper and I find them particularly rewarding), repairing/restoring things, servicing my own vehicles, and relying more on myself and my own talents. Some of the best times are spent sitting in a chair on my shop porch--a type of meditation perhaps. I don't feel like an ascetic, and I realize that it's not a life for everyone, but surely it's a good life, and preferable to being a drone with no free time and no money to spend in any free time.
2: I think they were speaking less about financial risk, like risking your savings, and more about other kinds of risks. Later in my life I moved to Costa Rica for a time (on an aside, I lived there about as cheaply as I did in my YMCA days). I was scared to do it, by myself, etc, but I looked at worst case scenarios, and it was like...I squandered my savings (10-15k, I don't remember), I was alive, bruised ego, and I went back to the US and got a low-paying job. I held out an amount of money equal to a plane ticket in case that scenario presented itself, and I had a great time in Costa Rica. I moved back with more money than I left with.
$60k for 40 acres and a home
What state are you in and how far from a big city?
Cheapest option at a proper restaurant: glass of water. I had times where that was the only option that I could manage, unless my friends insisted on paying for me. I'd feel bad, but they were better off and didn't mind (at least they said they didn't mind) and otherwise I might not have even gone out with them.
Splurging for me was going and getting 4 items off the dollar value menu at Wendy's instead of 2 or 3.
But it wouldn't really matter. I'd get sick, have to go to the doctor, get a bill I couldn't pay, it'd go to collections and wreck my credit, then my car would break down the same week, then it breaks down again in a different way a few months later, and will keep doing so because it's an old piece of shit but you can't get anything better, and there's just no getting ahead. Just sinking further and further into debt.
I didn't break out of that cycle until I got a job that almost doubled my salary and dedicated a couple of years to just digging myself out of the hole I had gotten myself into.
I'm a lot better off right now. Actually have savings, some investments. House, dogs, wife, spend more money than I should on stuff I don't really need. But I'm way, way behind others my age in my industry, and my credit is just okay now, not great.
They didn't mind. It feels very good to do something nice for a friend. If it didn't, they wouldn't keep inviting you.
Even when I was broke and living in NYC, I could still afford my subway pass. I mean barely, but I afforded it. That meant I could always get to the temp job I needed to get to without worrying.
If you think of car ownership as a "tax" because it's required in most parts of the country, it becomes a very expensive regressive tax indeed.
You appear to be very mistaken about the meaning of "externalized" (this is, of course, the charitable interpretation). Paying for a good or service you yourself consume does not constitute an externality. In fact, the exact opposite is true: if you forces others to pay for your open transportation, that would be an externality.
The common good of affordable and reliable public transportation was transformed into an everybody-must-own-a-car system.
Thus you and I and other people are paying tens of thousands of dollars to own and maintain cars because business interests felt it would be better for us to do so.
However, it is important to remember that words mean something, and anyone who tells you different is trying to sell you something (usually something involving the deaths of millions, but I digress...).
I expect that you returned the favor, although maybe not to the exact same friends. :-)
2. This is the exact point. Each of us have to judge the consequences of failure for each decision. If you only have a couple hundred dollars left after expenses, risk aversion is the right call—-and falls well within the real of managing your risk.
The term financial freedom doesn't just mean "making more than you spend". Above a certain income level you get the freedom to splurge. Being able to sit at a restaurant with a friend and not always choose the cheapest option is financial freedom. You can't get that by belt-tightening.
2. Risk isn't the same for everyone. it is fundamentally easier for certain people to take risks. If you make $200k per year, you can probably afford to gamble a little. But what if you only have a couple of hundred dollars to spend after rent and bills every month? Sure there are occasionally successful people who come from nothing, but starting a business or pivoting careers is much easier when you already have money.