Wish I'd had the opportunity to go "self employed" myself. I'm trying and will probably make it but I'm still a year or two away from convincing Anne that it's the thing to do.
Go to a book store and find the "Rich Dad, Poor Dad" and other books in the series. Lots of interesting tips on handling finances like the rich.
Also, just finished a book not long ago (sorry, don't remember the title) that dealt with the old "get and education, find a good job, etc." mind set and how that traps you into a cycle that you just can't break out of. Even if you make 90K or more you still "workin' for the man"
Also, I think self employment teaches you what "enough" is -- i.e. how much do you need to make to be "enough" -- now "enough" may be what your subsistance level is and you would like to make a bit more than "enough" but for a lot of folks, if they are doing what they really like to do and are making "enough" to pay the bills, take some time off now and then, and enjoy life then just maybe they ARE making "enough".
I'm 52 so probably in your dad's generation - I, too work in computers, I'm an IT analyst/geek -- I've been doing this pretty solid since about 1976 (started with alpha/numeric processing terminals by TI) and have been involved with personal computing since 1981. I HATE IT!! :twisted" But, it has paid the bills and allowed me some modicum of self respect
I have to remind myself, when talking with my 20 and 22 year old sons that I can't live their lives. I can't live mine through their's. And, I want them to really love whatever they do. So, I have life choice discussions real often with them. Sometimes I wish I was 22 again and had just an inkling of what I know now or had someone like me to advise them
Now, regarding the restaurant biz! If you haven't worked in one don't even think of starting one by yourself. Go work at a couple over the next couple of years -- maybe fast food first and then a "family" restaurant and then maybe upscale steak/seafood/etc. Get in as management for somebody like Red Lobster, Cody's, TGI Friday's, etc. and get your ASS BEAT for a coule of years. Managers have it bad with 50-75 hour weeks but owners of independent places have it worse.
Just my $.02 worth.