How do you get comfortable talking highly of yourself?

My problem isn't that I don't think highly of myself, I do. The problem I have is voicing it. There are few people I can voice some things with. However, there are times when I don't speak because I feel like it might come off as boastful, or like I'm trying to elevate myself. Even if I do talk about myself in a way that uplifts me sometimes start to overthink and worry of it came out wrong. I've learned to avoid it because of past experiences. However, I believe you can't tell the right person the wrong thing (within reason). So people I want in my life will know where I'm coming from. Still, lose my voice in conversations like these.
How do you get comfortable talking highly of yourself?
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