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Marc,
I think we can all identify with what you’re going through. I sympathize and commend you for even making the time to think of it… a lot of people are just on auto-pilot and do not even consider some of the most important questions to ask oneself — such as “why am I doing this? Why am I avoiding that? How do reconcile the viewpoints of others with my own personal integrity…
In response, I offer a few simple idea that changed my life for the better.
(1) Be wary of your own ego — the ego thrives on separation of some sort. Whether it be seeing oneself richer, more spiritual, more intellectual, less mainstream, or less materialistic. Some monks can have bigger egos than those of millionaires. The ego always wants to see itself as “different”. Give things that genuinely interest you in popular culture a chance — if you hate it, then dismiss it but there will be some things you enjoy. For example, I enjoy a Guniness Beer which is extremely popular as well as music from U2. I also love Starbucks espresso.
(2) Having compassion on other people will help you relate to them more — realize that most people are overwhelmed, stressed, and busy fretting over all of their problems. We as humans invariably all suffer from many of the same ills — such as feelings of inadequacy, never being satisfied, and looking in all the wrong places for fulfillment. We all share a common fate as well – being humbled, growing sick, and dying.
(3) As much as we need to develop individually through self reliance, meditation, contemplation, etc — there is the ever present need within our souls to relate and bond with others. Moreover, I believe that we can find out a lot about ourselves through other people. For example, my friend introduced me to mountain climbing — something that I would never have pursued on my own. My wife introduced me to a variety of movies that I would have never watched had she never met me. Hence, the infamous and powerful quote “no man is an island”.
I hope this helps. You seem like a good man!
Namaste