It's about intrinsic vs extrinsic rewards. For him, writing poetry was a reward in itself, and he didn't see himself joining the standard nine-to-five society anyway. So, even if he had failed after 40 years of writing during evenings and weekends, he wouldn't have any regrets. Of course, if someone does say startups just to get rich, and hates every minute of it, then it, if the spoils never materialize in the end, it will lead to bitterness.
But I've never seen a great musician in a crappy venue. And when I see a world class musician it is undeniable that they are great.
In my experience there are 1000s of writers not quite as good as Bukowski and some of them will make it but very few. When a truly great writer comes along I believe the hard part is actually writing the great literature and not finding a publisher.
What does being better have to do with it? Are you arguing against the idea that the best people always succeed? I don’t think I said that.
Because he got lucky. No, sacrificing everything for the goal does not always get you the goal. There's 1,000 Bukowskis out there, many better, and we'll never hear of them.
Sometimes you waste it all, and then you're supposed to look back and say, "Well, at least I gave it my all, and I just had bad luck." Yeah, that's really fucking comforting.