Maybe you have some underlying beliefs against bragging that are preventing you from being proud of yourself? Also consider the idea that happiness can also be generated from inside yourself, rather than just tied to outside circumstances.
After an achievement, major or small, consider rewarding yourself. Go out for a nice dinner with a good/old friend or your significant other or someone else close.
If you have a birthday coming up, you might consider taking that day to reflect on how much you've grown that day, recognize that you have more to do (if you feel that way) but be happy about where you are. Maybe you'd like to take someone who means a lot to you out for dinner or something like that.
And just plain do something fun. Maybe paintballing, or go bungee jumping or get something you've been wanting to get but couldn't really justify getting.
Just reward yourself.
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