I think it depends. If it's difficult to move up the ladder AND move to a new company, and you want the $$$ for whatever reason, then getting two jobs makes perfect sense.

I'm actually considering the option because I don't have the confidence to move into a job I love, so getting better paid and retire earlier is the next best thing. Maybe one full-time job with one contractor job to minimize the risk. I could take home $250K+ pre-tax which is pretty lucrative for Canadians, plus I can expense my laptop and other minor stuffs.

But I have never done that so not sure if I could handle the pressure. It would be nice if both jobs require minimum guidance and meetings.