Are you saying that there is some more direct route to working on what one wants? Or that the direct route to happiness is to give up such aspirations?
If your aspiration is simply to code interesting software projects all day long, I see no reason why being rich should be a prerequisite. Your expenses are minimal; you have no need of an office and can live anywhere. Will you require some money? Yes, and acquiring that will distract you slightly from the things you'd rather be doing. But that is a much better proposition, to me, than gambling away a decade or two of my best years on the remote chance to become wealthy and "completely" free.
You're talking theoretically about the life I actually lived for the second half of my twenties, living cheaply and supporting myself with occasional bursts of consulting. It was not as easy as you make it sound. I preferred it to a regular job (which leaves you too little time to work on your own stuff), but it was extremely stressful to keep running out of money. With kids it would have been impossible.
How remote the chances are of making money from a startup depend on the person. The probability ranges from a snowball's chance in hell to maybe 90% in the case of someone like Bill Gates. (He was not necessarily going to be the richest man of all, but the likelihood of him not even making enough to be independently wealthy was pretty small.) I can't tell what the chances would be in your case without meeting you, but certainly there are some people for whom starting a startup is a reasonable gamble.
It definitely wouldn't take decades to find out. When startups fail they usually fail in less than 2 years.
As a 27-year old, part-time consultant, it's not so theoretical :-) I agree I could never support a family living the way I do, but raising a family is at odds with maximizing your free time anyways.
I don't really know what to say about this. It makes me totally face_plain. In my opinion, a goal of maximizing your personal free time at the expense of family is completely crazy. You should raise a family because its joys are immense and awesome, more immense and awesome than anything involving a huge chunk of money and/or free time (i.e. boredom, which more often than not does not end well), and I would instantly sacrifice my entrepreneurial desires if I had to choose between my wife and son and my hope of getting a lot of money independently. It's much better to have a family waiting for you after an eight-hour work day than to set your own hours and come home to an empty house.
I draw the line at like 6 threads deep, so I will shut up after this, but:
At the expense of what family? The hypothetical one which I am purposely not creating? I'm glad that it's worked out well for you (really), but you need to recognize that, contrary to what people want to believe, parenthood and happiness are not synonymous. You look at my life and see empty houses (nevermind that I live with a bunch of fun, like-minded people); I look at yours and see sleep deprivation, debt, stress, loss of the ability to travel and develop myself personally--basically the end of everything I enjoy. Other than conventional wisdom, is there anything to suggest that your life is "immense and awesome", while mine must be empty and sad? For my part, I see a litany of studies suggesting that people like me are, on average, actually a lot happier (http://nymag.com/news/features/67024/).
I would never be so smug as to insinuate that you made the wrong choice. But it's not your place to make face_plains at me, either.
For what it's worth, as Daniel Gilbert notes in "Stumbling on Happiness", people's minds tend to rationalize their actions and warp the past based on more recent events.
If you were to marry and have kids, you would likely argue the same points about it being the greatest experience of your life. However, you would only feel that way because your memory of your past bachelor life would be distorted by the joy that your new settled life has brought you.
"You look at my life and see empty houses (nevermind that I live with a bunch of fun, like-minded people); I look at yours and see sleep deprivation, debt, stress, loss of the ability to travel and develop myself personally--basically the end of everything I enjoy."
You can have a very happy life with or without children. My wife and I waited until our late 30's to have our daughter. We were happy before and we're happy now. If we decided not to have a child we would have been happy. Your list of downsides to having a family are accurate with the exception of "develop myself personally". It depends on what you mean by developing yourself. If you mean being able to study interesting subjects, e.g. take foreign language classes/study cooking/etc., then there's some truth to it. With a child, you have to pick and choose what you study based on having a less flexible schedule. But, developing oneself isn't limited to that. My daughter causes me to learn patience, empathy, and selflessness far beyond what I could have learned without her. It's a matter of not having a choice to do otherwise.
As for the other side of developing oneself, she and I will be studying martial arts and piano together. Not bad.
Enjoy your life whatever your choice. You're the only one in control of your happiness.
It's not impossible, it's just adding another degree of difficulty. I did exactly this in the second half of my twenties. Working on my projects, doing consulting when I had to to support myself and my family. I believe the impetus that drives "family men" to seek shelter in a "normal" job can also drive you to be relentless in making your startup work. More skin in the game.
Also, team comes into play here. Personally. I know that if I wouldn't have had such a wonderful and supporting partner at home, the startup issue would have been a non-starter.
It's a little bit disingenuous to say earning lots of money is the same as "gambling away a decade or two" while a full-time job will "distract you slightly." Getting money and getting modestly rich are essentially the same thing, just one way you have a reasoned goal for which to optimize your money-earning.
In your youth, you don't have to care about risks much, hence your expenses are low. You can never get really broke, because you'll always have an able young body to sell and start over. The older you get the more you have to worry about risks.
Most hackerly types I can think of just go work on what they're interested in, without an explicit goal of making millions from it. Take the quintessential Jobs/Woz thing: Woz, the hacker of the pair, was interested in making Apple machines, but didn't give a damn about getting rich.
I bet he's pretty happy now that he is rich. And Steve Jobs wouldn't have bought Pixar and created NeXT if he hadn't made a fortune at Apple before he got fired.
Darn it you changed your reply after I replied, this still kind of applies. Edit again, you're reply is practically evolving every time I hit update.
Being free and being broke is what I think his direct route is. You can say that the pan handlers have more or less freedom than a business owner, depends on how you define the words.
Yeah but very few people can successfully pull this off. The vast majority of broke people are still harboring some sort of grudge against society or someone from their past - it's like they have 99% of the inconveniences of abandoning materialism, but none of the benefit because they refuse to "go all the way" with it.
In many ways intellectual freedom can only be found once material mastery has been achieved. There are a few famous examples from history that say otherwise, like Diogenes, but I doubt you're at his level. I also doubt you really believe in what you're saying, otherwise you would go straight to "abandoning" instead of posting on Hacker News.
Would you really say intellectual freedom is truly achieved only once the material has been achieved?
I would argue that there is a threshold for this material mastery. I don't think is necessary for it to be exorbitantly rich. I can look at researchers who enjoy their work, and are working on problems interesting to them. They usually don't have a big monetary profit. Just a thought
Way to much you, your and you're in that last sentence zachattack, I felt like you think I personally believe that is freedom. I don't believe in that codswallop at all I was just offering an interpretation of what he might have meant, much like his interpretation of freedom. Money is my means to the end and I won't stop till I've got enough.