Ask HN: Career and life advice for a 30yo

First I would take a step back and try to view the situation with less judgment. It's easy to look at the past and mythologize it and imagine it as perfect. Maybe there are more MBAs and executives and thought leaders today but the past you're romanticizing would have its own frustrations and road blocks.

The other thing it sounds like you're doing is looking around for a great opportunity rather than zeroing in on a thing you really care about and working on it. Your comment about engineers being a peasant class makes it sound like at least a part of you is more concerned about status than doing the kind of work that you say you're interested in.

Sounds like you need to answer for yourself what you're really looking for, how you would like to spend your days, what you would be proud of looking back on, etc. Rather than looking outward at the state of the industry, the status of developers, phds, MBAs, VCs or execs. If you want to build, start working on a product, figure out a market for it. But also know that at some point products do need to be sold, so eventually, you or a co-founder or your employees are going to have to figure out how to make money.

One of my favorite general pieces of advice is "you can decide what you want but you can't decide what it will cost you." You can decide to be a builder and an engineer but it probably won't come with the adulation you feel for Jamie Zawinski or Alan Kay. And if you talk to most people who are admired and have a lot of adulation, even if it's deserved, it's not something they tend to say they relish. They tend to still relish the work they valued for themselves and feel the adulation is overblown or doesn't actually give them anything of substance.

Maybe you could try some of the positions out there that do require a lot of expertise, e.g. Malware Analysis? I mean companies are supposed to make money so what do you expect them to do if they cannot pull out great products?

At my previous company we did Scrum with a capital S. We did planning poker, daily stand-ups (where we actually stood up), bi-weekly retrospectives and so on. However, we (the engineers) had also made it clear to management that we needed time slots for technical debt, which of course we got. It was a pleasure to work in a so oiled machinery.

So while we were still chasing features, we also had a say in when to do technical debt and could plan it out in a similar manner to new features.

You may find this essay by pg helpful in making your decision:

You Weren't Meant to Have a Boss - http://www.paulgraham.com/boss.html

It sounds like most of your disillusionment is with the profit seeking. Now, sure there are still some caveats here, but have you considered working in defence? While private defence contractor companies still make tons of money, there is not the noticeable profit incentive floating around since government contracts are taken for granted, very lucrative, and last a long time.

The pace is slower, but I've found managers on the whole to be more hands off, you get to be an individual contributor more easily, and there isn't the constant product hype.

Yes, iteration is slower. Yes, the documentation can be monotonous. No, you won't be writing code as often. But if you get the right job, you'll get to design some interesting stuff. You'll certainly learn a lot.

You can learn the next JavaScript framework through Google in a couple weeks. You aren't going to learn about how the software of a combat management system on a submarine works through Google. So much military hardware is "fly by wire" now, so there is software galore.

It's not for everybody, but with only 7 years into a career you should give it a shot. And then, worst case you decide it isn't for you, but maybe you get a great idea for a defence company along the way and you leave and win a government contract and get on the gravy train. Seriously, I'd say winning a Gov contract is easier than being bought by Google for $$$. Less competition, and you won't be selling based on growth potential, but on the quality of your product.