1: In 2002, long before I was a dev, I made about $14,000, working at a local YMCA. I had plenty of money. I paid rent (shared), I went out to eat a couple times per week (mainly the $13.50 all-you-can-eat crab at the chinese place), and I spent my leisure time how I wanted--for me that was primarily gaming, fishing (from the shore), programming, and coaching youth sports. I drove a beater car and did not have any luxury in my life, but I had a nice PC, a few nice fishing rods, etc.
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.