When you do something against what others around you are doing, or what the social norm expects, then not only do you have this layer of expectation from those who care about you, but even those who don't, find themselves getting upset at your choices. It seems ridiculous but it's he reality. I have found this to be the case, in the sense of myself not having what a gap year individual should have by now (aka a regular job), and hence not being able to be content with what I have and be happy....apparently.
Happiness is such a gooey, weird topic - what the heck does it mean really? I am pretty sure that if I was to plan the 'perfect' day that would have the goal of making me utterly content, I would fail miserably. This happens day-to-day with the habit of list making. You write down these things to-do because you think it will lead to a certain mood, emotion or outcome, yet the fact is that if you don't fancy doing that or are not in the mood then there is no point. There are perhaps 2% of instances that result in you actually enjoying the once perceived 'un-enjoyable', yet if this process of your whole day, talking yourself into doing a series of tasks one after the other, then you really are not going to be happy. A moderately-small set of order is great, then beyond that, freedom and flexibility is what is required.
I often get the question,'what are your plans for the rest of the day', and while half the time I know that I'm doing, the rest of the time I just follow my bliss, or what I feel like. I actually look inward and ask myself, 'what do you need?' then I try and do that. Sometimes I get distracted and annoyed at that process, yet most of the time it works, and when it does I am happy.
However the only thing that rubs up against this, is the expectation of others being that this could not possibly be the case. That there is something missing in my schedule, in my routine. While I am still looking for a job, I also am content with the now, with the present. Because if you are not, then you never will be. One has to appreciate life and their situation at all times, look on the bright side so to speak. There always is one.
Never feel embarrassed or judged for how you proceed. Make it yours and feel its every crazy, fun, quiet and meditative moments.