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Hey Wyn,
Maybe you are being too hard on yourself. Maybe all this searching for authenticity and trying to make people like you is taking away all the fun and possibility in life. Creating possibility is one of the best antidotes to loneliness and depression. It sounds like perhaps there is something in your life you need to move on from. If you know what you need to change, perhaps you could take a gradual approach toward moving away from it, toward the person who you want to become. I actually wrote a page on the person who I want to become (a philosopher named Epictetus advised doing this in the great book “The Art of Living”, which you might want to check out) and it can be very cathartic and guiding as you look ahead, and not backwards. One of the pieces of advice that changed my life that I read in that book is “Know what you can control, and what you can’t, and focus on what you can.” You can’t change anything that you’ve done, but you can control your actions and decisions as you move forward toward that person who you want to become. I think you’ll find the more you start to move toward that person, the more the right people will begin to come into your life. Focus on the hope out there, instead of being pulled into negative thinking.
T.H. White once wrote: “The best thing for being sad is to learn something.” Those little pockets of “learning time” can be so valuable when we are feeling down. What do you want to learn?
Maybe finding what you love doesn’t have to be so complicated. What makes you feel right in life? For me I like to just sort of walk around and listen and think, or not. It wasn’t something I “discovered”, but sort of fell into. I think being outside, in nature can be really spiritual and natural, and the act of listening may be one of the best things for healing and moving ahead.