When I think of TLC, that song usually comes to mind and in particular, that verse. Taken in context with the rest of the song, it is quite ok, but by itself, that line is rather demotivating. In the song, the artists spoke about a drug dealer or gang banger who was making money illegal and would end up in the gutter one day, leaving his loving mother behind. In that scenario, the artists are warning that we shouldn't chase after quick money at the expense of our lives. The other verses warns against unprotected sex with persons with whom you are newly acquainted and alludes to the fact that having sex with many people may lead to HIV. Again a waterfall is depicted as a bad thing that people go after that ends up damaging them.
I like the song and its message is very positive, however, I don't think the line 'don't go chasing waterfalls...' is appropriate for this song. Waterfalls are beautiful features of nature. A lot of rivers and lakes lead to waterfalls that usually continue on as rivers, lakes, streams, etc.,. In my opinion, a waterfall is synonymous to a big goal or dream. Why should we only stick to the things that we are used to. Almost all motivational books these days encourage us to push beyond our comfort zones (the rivers and lakes that we're used to). The problem with the people in the TLC song, Waterfalls, is the complete opposite. They were sticking to the rivers and lakes that they were used to. They were not chasing anything except mediocrity and a good time. The song should be reworked as 'Please go chase some waterfalls, don't stick to the rivers and lakes that you're used to!'. Sticking to rivers and lakes in which we know what will betide is of no use in this life. The unknown is always more interesting and almost always more rewarding.
Source: http://things-to-do-in-jamaica.com/ys-falls-jamaica/