No matter what, I always feel inadequate, alone, lost? It is an endless cycle I can't seem to defeat?

[Elvenmitth]

[NamerOfStars]

Well, that sucks. You might want to start building yourself up; self-esteem can be self-reinforcing. Take a book you like and record an audiobook version, one chapter a day. There's a free bit of software called Audacity that you can use to make minor edits and normalize basic audio stuff (maybe advanced audio stuff too; I'm strictly an amateur).

[Anonymous]

Often this is our inner self guiding us toward a path. Perhaps Invite God into your life, start reading scripture each day, praying and taking in the Word and that will slowly change. I recommend 'The Bible in One Year – a Commentary by Nicky Gumbel'

Notice how this society will encourage a guy your age to be promiscuous, to drink, to party, to chase girls, to fool around but they will never encourage you to seek God...