Steve Jobs is no better than you, me or someone else about those issues or questions, he did some stupid things about his well-being & co (like only eating apple as only food for a long period of time, taking some drugs, ...) but yes the fact that multiple successfull people talk about it is enough to take a look at it
For the automated responses I believe it's just automatic because we don't really digg to see where it come from. Like for example people usually eat fish on friday in France, it's mostly because old religious reasons. So lot's of people don't think about when to eat fish, they just do it on friday automatically. But from a scientific point of view you can eat fish any day. Like people think automatically that the pink color is for girl, without questionning it (but pink was "created" for males back in the mediaval days, it was a soft red for childs because red was the color of man, the blood they spilled when they fought. Blue was for girls, it was the purity etc).
So each of us have a automatic pattern that our parents, family, society have ingrain in our minds since the young age. And it's definitely less "stressful" for the brain because he's use to those, so he know what the outcome is : no need to think too much about this or that because he know how you'll look with them, how people react to the association, etc. It's a way to save some "brain power".
What they say is that if you have less decision fatigue you are more able to respond well to a choice who is forced upon you. You have more clarity about what's really important and you can choose with a better knowledge about the choice, the implication, the long term, etc so your choice is by default easier to make. What's make choices difficult at the first place is the fact you don't know what will happen after doing it. And at the very least, if you are not in a "fight or flight" mode you have better chance to choose according to your core values and don't regret it afterwards. You make the choice, you know why and after that ... even if the choice is bad one, at the end of the day you didn't know better at that time.
It's also a choice. But that's choosing to stay stuck between everything. If you know yourself enough you have probably some core values you want to represent, live by, ... and starting with that you can always make that choice according to them. People just don't spend enough time trying to know themselves to make those choices. It's like your last pic : the answer you receive when you toss the coin is your inner self expressing what your value is, it's instinctive. But you will just don't know why you respond in that way, people will just say thing like "i knew it in my guts". But someone else who know himself will not even have to toss the coin, he will choose according of his moral values.
That's the compounding effect, it's like in finance. A very small decision on the short term can have a tremendous effect on the long term. That's what trick most of the people, they want big results quickly in their lives.
I have a friend who wanted to loose at least 30kg and she had tried diet after diet for years. She was pleased when she dropped 5kg but at the end of the day she was back to her initial weight because that wasn't a way to eat for her on the long term. I just told her to drop 1 single cookie a day on her usual diet. It was easy. Than the next month I advise her to replace her 1 liter of organic orange juice a day by some clean water with few slices of orange or lemon in it. She still had the taste but not the sugar that are available in the pure juice. After few months she dropped the same 5kg and wasn't even noticing that she changed her diet.
After dropping 10 kg she felt lighter and confident enough to start jogging a little, and month after month she dropped 35kg in total (and will probably dropp few more in the next months), she now run half marathon, she's socially way more active than before (she was ashamed of her body), she met new people and have find a new job from one of those people, etc. So from just a cookie and a orange juice she flipped totally her life, they were just the entry point of small changes here and there. That's really something amazing to see