Or maybe I am being myopic? Are there more options to be had in life than mediocrity/wageslavery vs glory/startups?
There are billions of people on this planet. Do you think that the ones who aren't in Silicon Valley startups are all miserable? Their lives aren't worth living?
Ok, but more specifically. Let's say you want to lead a creative existence, working with technology, and you love the SF scene so much you just have to live here. You don't need to be in a startup for that. As they tell you to be frugal with a startup, be frugal with you life and all sorts of possibilities open up.
I know a number of people living in "hacker homes" where they drift in between working on startups, technology jobs, and then working on projects that just interest them. Sometimes they'll take an entire year off work to do something with no monetary gain, like a Burning Man or an open source project. You might have to live in an less desirable area with a lot of housemates, but once your rent is sub-$1000 and you cook most of your own food, you can live for an entire year once you've pulled off a couple of consulting gigs.
You're young, and I presume you don't have a spouse or kids, so this option is very possible for you.
I'm all for exploring unconventional lifestyle design patterns. And I have been nursing certain plans of becoming a techno-hippie :)
A lot of my friends work for the Wikimedia Foundation, Thunderbird, Mozilla, Tor, and so on. There's no possibility of walking away as a zillionaire, but neither do you have to work with (or for) dickwads who are only in it for the money and who are out to screw you out of your share. And if you're any good, there's a guarantee of doing something significant that you can point to later on your resume, should you want to go the entrepreneurial route. These organizations are global, so you get to do a fair bit of travelling too.
Non-profits have their own special brand of problems, but if you tally up the pros and cons they are definitely an option.
http://www.mozilla.org/en-US/about/careers.html
I don't think you get a job at Tor without being personally known to the developers. Volunteer, I guess.
Obviously this varies depending on where you are in the organization. But the bottom line is: there are always dicks, and they always try to screw somebody (that's what dicks do), and in startups, there are probably more of them because millions is more interesting than power over a few people.
Don't take on investors: make a product that earns money. Don't hire full or part time employees: find intelligent automated solutions to tricky problems or bring on contractors as necessary. Having control over what you make and when you make it means (for me, at least) more sleep, more money and less wasted time making someone else's dream a reality.
I thought basically the same thing you did as a teenager, and when I was formulating my career plans after college, it was "startups or bust". It turns out that employees at Google, Facebook, Mckinsey, Goldman Sachs, numerous hedge funds, and probably even some old-economy companies actually have quite a bit of freedom to do their jobs with creativity and excellence. Good managers don't try to control employees - they manage them, so that the employee's natural talents and inclinations are matched up to the needs of the organization. And a manager at a fast-growing company probably got put in that position because somebody else thought he would do well at it, while a manager at a startup got that way because he hated his old job enough to quit.
There're certainly things wrong with big companies - I could probably name half a dozen areas where Google is dysfunctional and probably not fixable because the dysfunction is an emergent property of having 30,000 people work on a suite of products used by billions. But unless you've worked in both big and small companies, you don't have enough information to understand what dysfunction is inherent to being big and what dysfunction is just the result of getting a bad boss.
Alternatively, you can raise (or save) a moderate amount of cash, work comfortably at whatever pace you choose, and build something scalable and sellable. If you're making quality software, it's not difficult to generate enough passive income to support the lifestyle you want to live.
(not affiliated with the author in any way, just enjoyed the book myself)
I'd strongly recommend the podcast as well: http://www.startupsfortherestofus.com/
And I'll recommend this one then: http://www.mixergy.com (I am quite active over email with the host and have arranged several of the interviews - Morten Lund and John Robb come to mind)
Take a look at the early blog posts from Balsamiq's Peldi, anything by Patrick Mackenzie, the Wufoo guys, Gary Vaynerchuck, or anything from the 37Signals guys. This talk by DHH never fails to motivate me: http://www.youtube.com/watch?v=0CDXJ6bMkMY
A startup will likely have stupid ideas about work ethic and they'll probably want to push your compensation into equity. For any startup you join, be realistic, it will not be the next google/facebook. You'll be doing well if it doesn't end up failing. If it does survive, the equity you got will probably be devaluated somehow.
There may be some lottery-level chance of becoming financially independent, but you'll save yourself effort by just working a TPS-land job and buying actual lottery tickets.
A much more consistent approach would be to contract (or consult if you have the chance) and live frugally. With this, you should be able to save up enough money to take a year off every few years.
Sure ... freelance. But depending on how you structure your work, you may end up with a similar work-load as a startup, or failure dropping you back into TPS-land.
I just consider it such a damn waste to sit in an office all day and basically do jack shit. It's not even that I dislike the work all that much, it's just... all those wasted hours. All down the drain.
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