Ideas on how to be more positive
One of the traits a lot of people, especially other young people find insufferable in me sometimes, is my negativity and pessimism about the future. But I've lived my entire life like this, I can't even envision how life is like for people who aren't like me. I was wondering if any of you who are more positive in outlook can share what goes through your head, and how you got there? And does anyone else think American culture puts too much emphasis on being positive?
Andy, I reached a point in my life when all my illusions were stripped away, and my two remaining choices were to despair or to beg God not to let me become bitter. I prayed hard for the latter and at last it was granted. I then asked for gratitude and received that as well. I have found that I must continue to seek these two things in prayer every day, because painful memories can drag us down in the briefest moment. God bless you.
Qui me amat, amet et Deum meum.
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Perhaps, instead of trying to change your underlying temperament (pessimistic), try disciplining your mind to focus on the now and leaving the future to God. Ask Him every day to increase your trust in Him. Whether the future will be good, bad, or (most likely) a combo — really doesn’t matter when you are accepting whatever comes in the now as His Will. Wisdom and perspective come with the passing of time, so you may find that some of your negativity mellows as you get older.
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There is nothing wrong with this.  I've always been pretty doom-and-gloom myself and find overly "positive" people to be rather irritating.  I do think there is an overemphasis on being positive, or as I see it, forcing a smile and embracing a false sense of wellbeing regardless of the circumstances.  An inauthenticity.

Don't get me wrong - I admire people who can always see the silver lining in the worst situations.  Without these people, I would be severely lacking balance in my perspective and might be driven over the edge.  My problem is instead with the people who pathologically avoid anything "negative" for fear of acknowledging any actual issues because "it's such a drag" or "it kills the vibe."  I think this latter example is widely encouraged.

On the flipside, letting our sober view of reality weigh us down can certainly make us a drag and deprive us of life's abundant joy.  I always try to focus on simple pleasures and expressing gratitude towards God for providing these things.  Music, art, a good meal, nature, etc.  I also recommend talking to people who can encourage your lighter side, pointing out that silver lining without dismissing your concerns.
Let nothing disturb you, 
Let nothing frighten you, 
All things are passing away: 
God never changes. 
Patience obtains all things
Whoever has God lacks nothing; 
God alone suffices.

-- St. Teresa of Avila
Qui me amat, amet et Deum meum.
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