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.
Develop an idea into a valuable tech business and get rich.
Or work at a regular job and make modest but secure income.
Our level of happiness will be relative to our current life, warping our history to match.
I can see many potential life threads for myself going forward. Most include a family because I'm married and both of us wish to have children. All of them include struggling to build a valuable tech company by solving a pressing need. Making enough money to survive in the meantime is a given (part time work), I can't imagine not paying the bills.
I take comfort in the fact that my personal success is independent of the happiness I can bring to and receive from my family, as long as my restless ambition doesn't become a burden on them. Life feels so short and ephemeral, 36 years have come and gone in the blink of an eye. At other times I feel ancient and have forgotten more than I'll ever learn from here on out.
"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.