I have always believed that people adjust to their circumstances in terms of happiness (if not, there would be riots everywhere, daily). In other words, so long as you have the basic necessities, health and friends (if you want them), the guy sweeping the street, or whatever, probably feels no more or less happy than the CEO having 5 holidays per year with first class flights etc. In my own life, in material terms I am far better off than when I was 21. In some ways, my job now is much easier too despite the responsibility. But the point is, I do not feel any more "happy" because of all this. It is a kind of equilibrium. In some ways it take more in my present circumstances to make me happy than it used to, and it takes less to make me unhappy. The things I dreamt of do not make me any happier than when I dreamt of them! If you cut out extremes of poverty and misfortune, I am sure that is that same for most people. I would very much doubt that Tim is "happier" day to day most of us are, despite having orders of magnitude above our wealth.
Very true. As humans, we are programmed to want more. Once we get what we want, we find new things to want. This leads us to live a life in an illusion of happiness being getting what we want, which means we will never reach it. It is also why billionaires never get "enough". Even if they stop wanting money, they still want more success, which is typically quantified by money.
We can teach ourselves to go against our human nature, but it takes a conscious effort, and practice. Just like we can teach ourselves to eat less fat and sugar even though it is in our biological nature to stuff ourselves with it when we see it. The first step is realizing that it is possible, rather than believing that it's not worth fighting your instincts. It also requires you to focus on what you are working towards, rather than what you are stepping away from. "Boy, I would like to have some nice, fresh, juicy pineapple" is a lot more compelling than "Uh, I really shouldn't eat that chocolate bar".
Once you teach yourself that happiness does not lie in the things you buy, you will find joy in simpler things. Like spending time with your family, if you have one. One thing that is very common among so-called successful people, in business or sports for that matter, is that they are successful at the expense of family and friends. And I have yet to hear 70 year old person wish they spent less time with the family and more time working (not counting poor people who couldn't afford to feed or school their kids).
This is the one thing that I am sceptical about in your post - a CEO having "5 holidays per year with first class flights" (unless you by that mean "days"?). It's a lot more likely that they are working 15 hours a day, at least 5 days a week but usually more, with a couple of days off around christmas.
Also, don't forget that at this level, when you see a CEO in a bar or at a sports game, it is very likely that he/she is still working. He will usually have colleagues and/or clients or suppliers around him. Even at my common level, when I am on a business trip my family thinks it's all just a glorified holiday in fancy hotels and expensive bars. The fact is that when I am sitting in a bar at 1AM with two clients, I am not off. I am working. It may be much more comfortable than stamping metal at the car factory, but it's still work, and your brain is not off. I do sometimes envy people with simpler jobs, who can just walk out at 4PM and not think about work until the next morning.
And if you think that you will be able to settle, as soon as you just reach the next level and get that new house, you are living the illusion. Keep in mind that millions of people in the world would consider a New York taxi driver to be filthy rich. If you are able to read this, you are well enough off to be able to be happy with what you have, if that's what you calibrate your mind to be.
Usually, when so-called "rich" people (which is in the eye of the beholder) seem happy, it is because they love their work. Not because of the money that work brings in. From the outside, we think we would be as happy if we had their salary, but we won't. We would be happy if we could also work with something we love (which I happen to do, for which I consider myself lucky).
By the way:
Apple CEO Tim Cook's daily routine includes waking before 5 a.m., drinking Diet Mountain Dew during the day, and holding marathon meetings.
www.businessinsider.com