I miss the JOS blog a lot as well. It influenced me a lot over a decade ago. It presented a very optimistic view of the field and career path of a programmer, with good writing, interesting tech viewpoints, and humor. There was also less tech blogging back then.
I really liked Joel's vision of what a software developer should be, especially what the working conditions should be. I feel he embraced the concept of being both a professional and, frankly, an adult.
http://www.joelonsoftware.com/articles/FieldGuidetoDeveloper...
My lament is that I really do think tech instead doubled down on what I feel is kind of a childish, "young people are just smarter" attitude, with giant open offices, back visibility, low autonomy,
The vision JOS presented is one that I can embrace. I'd encourage young people to go into software development if I thought they had a future similar to the one presented in this blog. That version of a tech career is still there, to an extent, but unfortunately, tech seems to have moved more strongly away from it over the last 15 years. I can't encourage young people to go into a field with giant open offices, back visibility, limited autonomy, office retreats to dave n busters. I suppose there's a subset who like this, but my impression is that a huge number of developers, a group that most certainly includes developers recently out of college in their 20s, find this cultural world to be a disappointment.