Coincidentally, I'm reading the book because I'm trying to decide whether to leave my small city teaching job at a and move to SV to get a big tech job. And the book and your experience suggest that it is better to leave and fail to thrive than to never leave at all. But may I ask why didn't you like it, or what should I look out for?
Turns out I both loved and hated it. I ended up only staying gone for about a year and moved back to the city I had left. I still don't regret that decision, I'm significantly happier now than I was. I think of radical life changes as tools for perspective, by doing what I did I realize how little of what I have I need and how easy it is to create a new life if the one I have isn't suiting me.
One thing I didn't like was living in the silicon valley suburbs. It felt like a small town with nothing going on for me. It was really car-centric, my apartment came with a covered parking spot because they just assumed that of course you have a car. If I had to do it again I'd get a job in SF and live in SF. I don't want long commutes and I don't want to live in suburbs. Since you're from a small town, YMMV. The SV suburbs might feel like a big upgrade to you, and having to drive everywhere might be something you're already used to.
Another thing was that the work was dry. This might be very different for you based on what employer and job you pick. My team was doing mostly maintenance and incremental upgrades on a product many years old. I found that dreadfully boring. I need something creative. This is something I didn't know then. My current job doesn't pay nearly as much but the work offers a lot more novelty and creative freedom. If I had to do it again, I'd make sure to join a team that's working on a project that has me genuinely excited, preferably a team that's building something rather than doing maintenance.
It was also really hard for me to be uprooted from my hometown where I'd always lived and away from my friends. What made it even harder was that I fell into a depression right before moving to California. My mother was suddenly hospitalized, right as I was going through other stressful things and preparing for an international move. The extra stress was too much. Then I landed in California, and I had to start my first job, and I didn't have any friends there to support me. It's hard to boostrap a network of friends starting from nobody, and it's even harder when you're depressed... You have no energy to go out and you're coming from a place where you need people to help and support you, rather than a place of "I'm a fun person to spend time with".
Lastly, while I lived in California, after being on antidepressants for a bit and feeling more hopeful again, I tried dating, and I hated my experience. It feels, to me, like SV has an overabundance of men, because of the constant inflow of tech workers. If you're a single guy, you're moving to a place where there are too many men. In any other city, being a successful tech worker is something that will earn you points, but in SV, every woman knows they could date a Google engineer if they wanted to, at least that's how it seemed to me. Lots of ghosting and being treated in ways that I found disrespectful. To make matters more complicated, lots of people in and around SF are polyamorous, which is not something I want to get involved with.
May I ask how do you feel now about your current life? Did you leave the States?
If you're asking if I'm happy, I would say I'm definitely more emotionally stable. I've been at the same job since I came back and currently don't plan to leave. I still feel down from time to time, not completely fulfilled, but I think I'd feel that way anywhere. I feel a little lost these days because I don't really know what I want to do with my life. I feel like I lack purpose.
Dating here in a big city seems easier than in the Silicon Valley suburbs. It's tricky (because dating is tricky), but I have no trouble getting dates. I did lose touch with many acquaintances after being away for a year. Party friends, when you stop going out with them regularly, stop thinking about you. I have a small number of close friends that I had before I left and I generally feel like I get enough social.
Choosing a college may be a cost, but for now there are workable alternatives.
And you always have the way to know or at least roughly estimate which is good enough for a sane decision. You just take the cost of acquiring information into your decision time and you're gold. Apply hard limit for time and problem disappears. You did the best you could given the constraints.
In fact, the typical problem today is that you have too many ways to know and not enough ways to verify veracity.
On regrets and mistakes, Jordan Peterson talks about this sort of thing in a beautiful way as the idea of "redemptive mistakes", and that "people are a lot more unhappy when they look back in their lives about the things they didn't do than they are about the mistakes they made while they were doing things" - [https://www.youtube.com/watch?v=ZwGDnSWmqhM]. It has stuck with me as I try to be more permissive of myself making mistakes and being imperfect.
There's a clear spectrum between recklessness on one end, indecision and inaction on the other and doing right things right in the middle, spontaneously or in a planned way.
Relevancy is key, nobody remembers things that are irrelevant by definition as a regret... Cost is a kind of relevancy.
Going back to the article, you almost completely lost contact with the original problem once you're past third or rarely fourth order thinking because you will lack enough particular data to decide on any measure of success, with exception of particularly structured recursive problems. Welcome to decision variant of Goedel's second. Decisions and axioms (data points) are countable.
The thing is, you simply have no way to know. What exact future you'll end up with is about as predictable as the weather on this day five years from now. You have no idea who are the people you haven't yet met that are going to change your life, what roadblocks you'll find on the way, whether you'll suddenly fall into a depression, etc. You can only rely on objective metrics (trends, statistics), testimonials, and general gut feeling.
For myself, 3 years ago, after my studies, I was wondering whether I should relocate to silicon valley for a big tech job or not. It was scary. I loved my hometown, had many friends, etc. I figured, however, that I might as well do this sort of experiment (moving to another city/country) while I'm young and have no spouse or property. I did make the move, and unfortunately, I didn't enjoy my big tech job, nor did I enjoy living in silicon valley, it wasn't a good experience, so I moved back, thankfully with a decent wad of cash to wipe my tears with.
I didn't like silicon valley, but I don't regret my decision to try it. Why, because I also knew that I kind of had to try it, because if I didn't, there might always be some FOMO in the back of my mind (what if I'd taken this big silicon valley job, would my live be better right now?). Now I've done it, I've been there, and I know what it's like. The pressure/temptation is gone. So my two cents are to trust your gut, do commit to decisions, and also don't be overly afraid of experimenting when you're young: it might not work out, but you'll learn something along the way.