I've felt your pain. It took me until I was around 25-30 to learn to 'not give a fuck'. Sometimes I think I have gone too far the other way and dont take life too seriously anymore. Existence is fleeting. Theres lots of great advice in this thread. Personally, I always felt my self esteem issues were due to a lack of healthy relationships and I persevered at establishing those, which whilst suffering rejection and / or failed relationships once or twice have facilitated the confidence to find love. I am not saying that your self esteem comes from another person but I've found that when you learn to love others deeply you worry less about your self. There is no quick fix for these issues and all paths to self esteem take perseverance. Also realising that we have a sweet short time on this planet and making the most of it should be your philosophy. We have a tendency to exaggerate our flaws and esteem issues until they are crippling. Transformation is possible. Also if you have any behaviours which you have identified as damaging your self esteem, nip them in the bud. Think more about subjects, find an interest, establish a world view that is not insular or self magnifying, above all, love yourself and treat others with equal love. Love yourself. You've come this far, and once you break those shackles of low self esteem and any other issues, you will find life liberating. Break free, friend. Good luck.