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Very true! It is so easy at a young age to be pressured by your peers and feel insecure because of things they say about you, no matter how nonsensical and untrue it may be. It took me longer than I would've liked to finally learn to say "Who cares what they think? I'm doing what's best for me."
I personally think this depends on the reason for dropping out. I dropped out because it just wasn't for me and I ended up going into a different field than I had originally planned, which didn't require a degree and paid better in the long run. I don't regret my choice at all. However, this definitely does depend on your options and what fields you're planning to go into.
My mistake was thinking I'd get financial aid to pay for my 2nd semester. Didn't happen. Had to drop out and re-enrol in the fall again working part-time.