This, I think, is what drives writers to drink. It helps them push through potentially crippling doubt in the quality of their work.
Don, I'd recommend you read 'On Writing' by Stephen King, if you haven't already. It's one of the single best sources of advice for writers. Truly dynamite.
Not reflecting on Don who I don't know but I've always wondered if people who go out of their way in trying to appear to be humble are reacting to the disgust that they feel when others aren't appearing humble.
Stuff like this:
"I think it was a shock to my son to see how I was regarded at work. Of course, that didn’t mean he started respecting me at home but, hey, a man can dream."
and this:
"At my core, I’m just a tinkerer who got very lucky."
Edit: What I mean is that Don (appears) to be going out of his way to say "aw shucks I'm not special I got lucky" and "I'm well respected but my kid still gives me problems just like yours does". The bragging of the first sentence "shock to my son to see how I was regarded" is tempered by the 2nd sentence. (Same with the tinkerer/got very lucky in other words I'm no different then you are we are all equal but I got lucky so don't hate me..)
Personally, I'd say just take them at their word: this is how they actually feel. Not everyone is trying to win some kind of popularity contents with every sentence they write. While he may have been trying to temper his 1st sentence, as you say, I'm going to just believe he is being genuine here and means exactly what he says. I don't think he is really going out of his way here.
You can only improve if you recognize your faults. People who have become exceptional, are the type that consistently improve, who therefore constantly recognize their limitations.
Thus when I see humility from people I respect, my default assumption is that this is not false modesty - I am getting a glimpse of the process that made them into people I respect.
Not always true. However it has proven true often enough that it remains my default assumption.
> I've always wondered if people who go out of their way in trying to appear to be humble are reacting to the disgust that they feel when others aren't appearing humble.
I can’t speak for Don, but for me it’s always been an attempt to communicate three things:
1. I am not inherently smarter or more talented or in any way “better” than you
2. My accomplishments come from long hours and hard work
3. Even after taking #2 into consideration, I probably wouldn’t be where I am without all of the dumb luck I’ve stumbled upon over the years
> in other words I'm no different then you are we are all equal but I got lucky so don't hate me..
It’s the opposite for me: don’t make me a hero! I’m just a guy who had some ideas and saw them through to the best of my abilities- something you can do too.