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I think they should've just called this 388.5, since it was very clearly meant to be the second half of last chapter, and 389 was to be the Ochaco vs. Toga chapter as the colour page insinuates, before his usual health issues resulted in being unable to finish so just saved the rest of it for this week.
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I read it as him wondering if it was so simple to do all of this to get his family to look at him, why it didn't happen sooner. Whether this is him thinking he should've acted out in this extravagant of a way earlier to get their attention, or if it's him reflecting on why he couldn't have been noticed without acting out is probably something that could interpreted either way.