I think it super depends on which direction you come at this from.
Like, I've seen people look at something difficult that they WANT to draw, and say "Oh, but I probably can't pull that off, so I won't bother" or "oh, but that's way too hard for me, I can't draw that" even though they're obviously hyped about the concept. But.... you'll never gain those skills if you don't try. You'll never even learn what skills you need to improve to do the thing!!
And so I think if you're looking at it as "I've only succeeded when I've successfully drawn the thing," then someone telling you "no, a success can be learning something, which you only do by trying the things you can't do yet" is really empowering advice!!
But I do agree that coming at it from the position of "I'm a failure unless I'm actively pushing myself and always trying to do new and harder things, and if I stop to draw a bunch of Headshots Facing Slightly Left for fun then I'm basically just wasting my time" then, seeing that as a failure isn't helpful or productive or spurring you on to improve, honestly -- it's just guilting yourself for drawing things that you like and are comfortable with. But why the heck are we drawing if it's not to draw things we like drawing? So if you're coming from that direction, then this advice won't feel good at all -- it will seem to push a mindset that you work hard to escape.
Sometimes advice isn't bad, but isn't for everyone, and I honestly feel like this falls into that. It doesn't brand itself as "bulletproof argument for only ever doing hard things" -- it's an argument for trying hard things when you run into them -- but the way it's presented will be empowering to some folks and won't feel good to others.
Basically:
(from here)