Is it harder to make money or to keep it?

I have always read (and it seems to be true) that it is harder to keep $ than make it.
I got to thinking that today while I was watching an old episode of the Little Rascals from 1938. I got it from 'Nick-at-Nite'. Anyway.
So that show would be during the Great Depression of the 1930's
and about 9 years after the big stock market crash of October '29.
It is interesting to watch those old shows just to see how poor everyone seemed and how those who had any $ were held in high regard. It was hard to make money then, but even harder to keep it if you managed to get any. It does not seem that different in the grand scheme of things now (that it is harder to keep it, then get it).
There are always needs and wants demanding your dollars.
I guess what I am trying to do is
think out loud about the benefit of investing a set amount of $ into VTSMX or VTI and letting it ride for 20 or 30 years.
Is it possible to never look at it? I mean you can do all the research in the world and you know the averages will be around 8 to 9%. So, if you know you want to be long, why ever look at it?
I keep thinking that that SP 500 is not the way to go just because of the fact that that average gets so heavily weighted with the dominating sector of whatever is popular at the moment.
Like CSCO was about 4% of the entire SP 500 during the tech boom. In my 401-k the only index is SP 500, so there it will have to suffice. And obviously even that does not matter over a long period.
But for my taxable accounts I am think that a broader index is the way to go...
So, that is what I plan to do, go with the broader index and let it ride.
If I don't have it, I can't spend it. Like a 401-k deduction.
So, now I can go about the business of trying to make more $ for the future, and keeping what I do have by letting the invested $ stay ahead of the inflation curve.

This blog probably seems a little fuzzy... it is late and I am up worrying about the Katrina aftermath and $4 a gallon gas prices (yes, I read an article about that in Marketwatch.com today). Now, that is scary.