Red Squirrel I'm not sure how much experience you have with earning and the business world, but 100K really isn't that much money. From your post it seems as if you're possibly rather young and just starting out? If you're not then I'm not sure where your opinion would stem from. I suppose if I net 100K cash after taxes it alters that, but still not significantly.
When you make six figures you're not going to live like you make 30K. You don't have to live far beyond your means and blow the money, but you're not going to live the same way you do making less than 30% of that level. I've worked my way from that entry level to the levels were talking about now. I don't see more than a small fraction of people getting to a certain level and saying "yea I wouldn't mind going back to the socioeconomic status at 21". Show me someone who believes that.
My suggestion to you is to not start a business with the opinion you have about how to run one. Most businesses run during business hours and if you're not going to run during those hours, then you're not going to be in business very long. Running a business takes some practical approach even if you have some incredible groundbreaking product/service. You mentioned some IT/hosting which usually has its strongest role in supporting other businesses, which likely operate primarily during business hours (weird how they are called business hours, right?).
Your last paragraph reads like a discontented hippie book. People still farm a lot (87% are owned/operated by individuals/families) and the overwhelming majority of businesses in America are small businesses. I'm not sure the people living "100's" of years ago would agree that it was more rewarding and I'm nearly 100% positive that data doesn't support it being anywhere near as healthy as we are today.
brianmanahan over 10 years ago in my 20s I could 'live' on 30K. There is no way I could live on anything remotely close to 30K now. I suppose if I planned on being single, living in an apartment and wearing the same underwear for 5 years on end then it might be possible. Otherwise it's a no go.
I know there are plenty of people who manage to do some form of early retirement like you refer to. I also know from experience with people involved in that scene is they are obsessed with saving money. To the point where it's detrimental to their current lives. I'm not sure what numbers you're lookng at but retiring at such an early age is incredibly difficult. I would have to save a solid 75K/year to 'retire' at around 45. That is assuming I'm getting a modest return and I'm only living on 30K/year.
If you can manage that than good for you. It's going to take you a solid 20 years of working constantly, saving every possible penny and living at the same nominal level that entire time. It seems from your last line that you may not have the gumption to do that. You dislike work more and more and cannot keep a healthy mental perspective. That's a recipe for disaster.
I don't see completely denying yourself for a couple decades during your youth just to retire to the equivalent of a 30K year income as being a sweet plan. You'll have a whole lot of time to do very little because of the paltry draw you have to live on. If that's what you think you want then all the power to ya. I can only fathom that plan working if you want to live like a 22 yr old bachelor.
Happy saving!