Adam tends to focus more on the househusband's stress of dealing with day-to-day life, so we rarely get a chance to see the workplace from Laura's point of view. When we do get tantalizing glimpses from her POV, they're relatively brief. One notable example is her way of dealing with sexual harassment in a not-so-subtle subtle way.
This memorable way of getting to the point results in unpleasant experience that both sides would rather prefer to forget for different reasons. So its somewhat surprising to see a familiar face in a later strip. The side passengers are slightly different, but there's the same guy sleeping in the front seat. Unless Laura's prone to travelling with the same people in her business freights, a more likely possibility is that it's from her memory of past travels, and that one with the skeevy businessman leering at her stuck out in her mind. We're more prone to remember the bad experiences than the good or uneventual ones.