Ok, I am in my mid-30's and very stable for the first time ever. My perspective will differ greatly from people born before 1980 or so because reality is that opportunities afforded young men have changed drastically from previous generations to this one.
- Professional Life: I am going to assume you don't have a proper career and that your income is inconsistent, or else you wouldn't have made this post. If I am wrong, no problem. But I don't think I am. So, I will say, get a day job (if you can). Working literally anywhere is better than not working. Then do everything in your power to get into the profession that suits you. You are already old enough that NOTHING high risk is going to pan out for you. If you were going to be a movie star, you would already be in movies. If you were going to be a rock star, you would already have a major record label. If you were going to be a great chef, you would already be sous chef somewhere highly rated. Go down the list: every sexy exciting career opportunity is donezo for you, which is freeing.
If you didn't go to college or finish college, don't bother now unless someone else is paying for it. No one is excited about hiring a 36 year-old recent college graduate with no life experience. If you did go to college, but you have been considering grad school: why? If you think a MA will jumpstart your career or let you start at a higher level than just doing 2 years of entry level work, you are probably wrong. If you are just deciding now to try to be a lawyer or a dentist or something, don't bother. Either one will leave you with $150k-250k of debt that you will probably never pay off (and I am saying this as a lawyer with $180k of debt). This doesn't mean all education is worthless -- it is still a decent time to get a certification from a trade program at a community college, for example. Or you can take a continuing education program at a public university in a field you like. Just take a class or two, assuming the cost is low. Then you will have something to talk about in an entry-level interview.
Some employers worth considering for someone with zero valuable experience and skills: Grocery stores (particularly Trader Joe's and Costco), shipping companies, government agencies and anything with a union (especially healthcare and law enforcement -- cops make twice what you think they do after you calculate their full benefits package and overtime and disposable income can be higher for nurses than doctors after you consider student loans).
No job that has inconsistent income (sales), considers you an "independent contractor" or requires you to pay them before you make money (multilevel marketing) are worth it.
Don't start a business unless it's with (at least partially) someone else's money or you can get an unsecured loan.
- Personal/Romantic Life: Be 100% honest about what you want. If you want to be married within 2 years and have 2 kids before you're 40, you should let people know that. If you want your partner to perform certain unusual sex acts daily, maybe wait until the third date, but don't hide that, either. If you go into a relationship wanting one thing, but pretending like you want something else, you won't be happy and neither will your partner.
If you are single and don't want to be, absolutely do not use Tindr or Grindr or any other "hookup" apps or services. Don't use free dating services, either -- pay for the premium package on whatever app or service appears to be marketing to you. Don't present the version of yourself you think people want, just present who you think you are and what you want. I was lucky enough to never date online and to marry someone I met in college, but most of my friends and family members my age or younger were less lucky.
- Decisions that matter more than you think: Where to live? Where you live doesn't just mean what people and bars are nearby, it also means what opportunities are you likely to find or not find. Any city that is really hip, for example, will have 10 times the number of applicants for every job at your age group as a city that isn't hip. Small towns are going to benefit locals more than bigger cities. Then the "local industry" will flavor everything. In the bay area, if you don't work in tech, you are generally at a disadvantage because no one else pays as much and the cost of living (particularly housing) is built around a society where people are all earning six figures and not having kids until they're 35. Try buying a house somewhere with a good school district a commutable distance from your middle class office job in Oakland -- you likely won't find a 3BR house for less than $800,000 near a decent school within a 45-minute drive from downtown Oakland. But it's even harder elsewhere. In Portland, OR, that same $80k office job in Oakland will pay $45k and will go to someone with connections or 10 years experience because there are just so many young people who want to live in Portland. The best opportunities are usually doing things other people don't want to do, be it living in a place that's "not cool" or doing a job that's not impressive. But a plumber makes more than a teacher and a job posting in San Diego wants more experience for less pay than the same job posting in Modesto, where the cost of living is about 1/3 what it is in San Diego. That's just how it is.
What to buy? Responsibility is cooler the older you get. Driving a Nissan and wearing Clarks loafers didn't seem like it communicated "success" to me when I was 25, but now I know that it communicates "he has his s*** together" to the rest of the world, who laughs at the 35 year-old guy with a receding hairline who gets out of his Camaro wearing $300 basketball shoes. Responsibility isn't just avoiding impractical purchases, but also knowing when to spend more. There are so many ways you can save yourself money by buying better upfront, and it usually won't make you look any better. Buy better grout when you redo your bathroom. Get yourself the best mattress you can afford -- your back is worth it. Good quality sheets cost 5 times as much as cheap sheets, but last 10 times longer and feel 10 times better.
Who to hang out with? First of all, if you're already 30, the time for making mistakes is over. No one who does cocaine or manipulates drunk women into having regrettable sex with them is friend material anymore. No one who gets in fights with strangers or values people based on how hot their significant others are is friend material. Grown-ups only from here on out. Also, the longer a relationship has lasted, the more it is worth. Your friend from high school who you kept in regular contact with until he moved to another state two years ago is worth staying in touch with. Your best drinking buddy who you have known for the past 8 months isn't worth as much to you, even if it feels like he is. Your cousins who you grew up with care more about you than your work friends do and they know you better, too. Your parents will die and before they do that, they will be weaker/dumber/less competent than you. They are worth getting dinner with sometimes.
I've been watching this thread, thinking of what to say recently. Thanks for the great reply, I do feel like you've seen a lot of the stuff I am looking at when I asked the initial question.
The clarification is that I did have a proper career in another country, and can do it to a lesser degree here, but don't have the necessary degree to really be on top in it. Also not sure if that's really what I want to do for the next 30 years. I actually have enough money to coast for the next decade easily.
Yes, I am very practical now. I am no longer interested in being an individual or "known" or anything like that.
-My romantic life is basically shelved for now. I'm not interested really at the moment and can't imaging being in a situation of having "divorce" and all its accompaniments hanging over my head again.
Maybe to give a little back on the romantic/friends aspect. I think I refuse to go out drinking at bars with people. I will happily drink at their house or outdoors, or I hope to do more daytime coffee dates. I just don't like anything about drinking at bars. Such a waste of time.
So basically, at the moment I am torn between starting at the low-mid level of a decent job with little chance for advancement, or prioritizing a 1 year max degree for a skilled trade or a small step up in this career.