My previous comment was an attempt at humor, but actually, the notion of "smartest person" is too ill-defined to be very useful. People are smart at different things. For example, one person might be smarter at playing chess than another, while the second might be smarter at writing computer programs.
So let's replace the notion of "smartest person" with something better defined, like "most successful at playing chess, as measured by their chess rating." In that case, we know who the best in the world is, it's Magnus Carlsen. It would indeed be a waste of time for him to seek chess matches where there was somebody better than him, but it is in fact good advice for everybody else to seek to play against better opponents.
However, the strongest players all find that inevitably, they are nearly always stronger than their opponents. For example, the #2 in the world, Levon Aronian, is stronger unless he plays Carlsen. Every grandmaster finds that the large majority of his games are against weaker opponents.
So if you're really "smart," it's good advice to try to surround yourself with "smarter" people, but don't beat yourself up if you find it hard to do--it's an inevitable consequence of mathematics that the "smartest" people will tend to surround themselves with less "smart" people, at least if you're only measuring "smartness" in one way.