The most difficult thing about escaping from Shouldland won’t be the people who want you to stay on their well-worn, risk-free, path. The hardest part will be overcoming your own insecurities to stay on the path of true freedom.
People will be resentful of your decision to walk your own path. When you find the courage, and are prepared well, you can stand up to the citizens of Shouldland, at other times you’ll just have to ignore them.
Once you have learned a little about Shouldland and feel ready to escape it, you need to ask yourself ‘do I really want this?’ Like the old saying goes ‘be careful what you wish for, it just might come true’. Most people live in Shouldland, some of us live outside it. The people who are aware of Shouldland (the idea, not necessarily the name) and live outside of it are not automatically any happier than people living ignorantly inside Shouldland. In fact they are sometimes less happy. As another favourite saying goes: ‘ignorance is bliss’.
You have to ask yourself, before reading any further, do you want to realise the truth and risk being less happy? “For in much wisdom is much grief: and he that increases knowledge increases sorrow” (King James Bible: Ecclesiastes, chapter 1, verse 18).
Obviously I think that it is worth the risk, that’s why I am writing this for you. True happiness and true freedom comes from having a real understanding of the world; to know it, and to be at one with it.
But why would anyone take the risk of alienating others and not fitting in with their tribe only to try to escape Shouldland? Short answer: happiness. Real, genuine happiness, like a monk or other enlightened person. Not that escaping Shouldland necessarily results in full enlightenment, but it is definitely on the way, and removes a lot of life’s stresses.
People become unhappy (often permanently) when their lives don’t turn out exactly as they expect it should. An example of this that I see a lot of in society involves many of our ‘senior’ citizens, the elderly person who believes in the old tradition of ‘respect your elders’, even when they are mean and grumpy to other people. These elderly people think that they can mistreat others (i.e. younger family members) and still have these people visit them. Back when they were children or young adults they visited their grandparents / parents no matter how unkind their elders were, and expect the same privilege now. Well unfortunately for them it is a new age and people won’t necessarily feel this obligation, thus the elderly person feels unhappy because people won’t visit them. Getting out of Shouldland is a lot about moving from old fashioned thinking to a more modern perspective on life.
To leave Shouldland you need to get rid of the feeling of obligation in your life. Obligation is the fuel of Shouldland. Don’t be obliged to follow some antiquated rule that has no relevance in your life. Do you have any examples of this in your life?