Honestly, it's time we all put our money where our mouths are. A hobbyist/individual license for Mathematica's desktop version is $170/year (or $335 for a forever license to the current version). If we really value our time, convenience and happiness, paying for software which we consider awesome should be a no-brainer. Heck, that's not even 1% of annual rent for someone living in the Bay Area. Of course, this comment is overly broad, and doesn't apply directly to people living in areas with lower cost of living or purchasing power (I grew up in India, so I understand the disparity).

I think Mathematica is quite fantastic (took me some time to understand it's patterns). I don't use it currently because 1) A lot of my current work is numerical and not symbolic -- for which Mathematica isn't great; so I use Python/Julia 2) From a long term perspective, I wouldn't want to invest a large fraction of my personal computing efforts into a proprietary single point of failure.

TBH, with regards to paying for software, my psychological motivation is still a work in progress (so the comments above are directed at myself as much as at others), but I'm trying to build a habit of doing it more -- especially to support free software. I care about computing too much -- I would hate to look back on this twenty years later and rue the loss of computing freedom because we were too stingy to invest a hundred bucks a year in the appropriate places.