What thing that I usually find annoying is the assumption that happiness is the highest goal in a person's life. And here I am referring to the happiness in the hedonistic sense. You can see it either explicitly said in a lot of the self-development books and seminars, so it lurks there, being just implicitly presented, as in economic theories.
So let me first try to tackle the problem of living the life we want. This one seems to be the more presented of all of them. Be it in the advertisement or pictures of beaches where people would enjoy the rest of their life. The latter which I never understood. Don't people realize that they would be bored shitless there after a while?
One interesting thought experiment is Nozick’s experience machine. What is comes down to, if you could reprogram the matrix in any way you could, would you plug in? Surprisingly not everybody would. In a different formulation of the problem, around third of the people say they would. Which is an interesting way of saying, that there might be other things that can affect it.
Sure, it is not that sexy, if it ends up that they only do it because of the status quo bias. People also would not be willing to leave the simulation, if a person would tell them, that they are in the simulation right now and that they have the chance to leave. But these percentages can be greatly influenced by adding just one sentence about how the life is outside the simulations.
So it seems that as least when we come to these experiments, it is that we value the current situation enough, that we are unwilling to change in most cases. And yet, at least most people that I met would not say that they have 'achieve their happiness' yet.
The other thing we don't take into account is that sometimes it is a lot easier to dream about something than actually living it. I mean, who had not dreamed to be a wither a president of the country, a famous actor, famous singer or world champion is some sport.
But people that dream about being presidents don't take into account that they have a rules called protocol that they have to constantly act in accordance to. That they are the ones that will need to resolve the most thorny problems (unless you are actually a country like mine, where the president don't have much power) and will be hated by people that will perceive you working against them, you will have to meet people that other people decide that you need to meet. There is just not a lot of freedom in the life of presidents.
Now let us go on the famous actor and famous singer example. I have heard a lot of them complain in how people stock them in their home, trying to see them through their windows. How some people go as far as physical attack, if they think they are ignored (like bitting, which fyi is discussing). For example, I heard that there are regular bus tours to go and see the house of Justin Bieber (is it bad, that I knew this face, but I had to google his name?). Can you imagine having a bus of people every day going around you house?
And then there are the professional sportsman. For people that have troubles going on the diet or going to the gym every day, can you imagine having you food specified to the miniature detail and having trainings also for hours per day. Not to mention having the mental focus to ignore the audience that think have the right to your time?
In the end, it is easier to dream than to experience our dreams. Because deep down we know that we will simply have different problems when achieving our dreams and it is easier to deal with the problems we are already familiar with.