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I consider you the one with an extremely off putting.  You're being frivolous with the guys career and money.  He either needs to step up or go home.  Honestly I find this coddling your displaying extremely selfish so you feel better about yourself.  And ultimately abhorrent behaviour given you're taking this guys dreams and giving him false hope.  He really really really needs to improve not hear fake false platitudes that make you feel better about yourself.   This kid needs a kick in the pants.  Who are you to deny the guy honest critique and helpful information that will actually lead to improvement rather than selfish garbage so you feel better about yourself. This is why we do not Coddle artists 

In the 1950's there's a story about All Williamson and Wally wood that is particularly relevant to this discussion.  

Wally Wood a titan of EC comics, in a fit of frustration, verbally dismantled Williamson’s pages—calling them sloppy, amateurish, and lacking in structure, physically marked up or trashed a piece Williamson had poured his heart into. This wasn’t a polite “here’s how to improve” it was a harsh critique bordering on cruelty. Williamson, devastated, reportedly felt his work was destroyed not just critiqued but rendered worthless in his own eyes by someone he admired.  Rather than being crumpling under this, Williamson took it as a challenge. He studied Wood’s techniques obsessively, honing his line work and storytelling to match the master’s level. By the late 1950s, Williamson was turning heads with his own EC stories, and his career soared through the 1960s and beyond—winning him accolades for titles like Flash Gordon and Star Wars comics. The harsh critique from Wood didn’t literally end his art but shattered his confidence long enough to force a reckoning, which he turned into fuel for a Hall of Fame career.