I dropped out and I don't regret my decision. I can only speak for myself, but dropping out wasn't this rebellion type undertaking. It was a decision that lingered in my head for quite some time. The most important thing to emphasize here is I was very unhappy and even borderline depressed being in college. The same way someone can feel that way in a certain type of job, college made me feel that way too. I stuck it out for as long as possible but ultimately I took the leap and dropped out and I have been very happy ever since. Sure sometimes it's harder to get a good paying job, but I find that challenge as something that really keeps me focused and it's actually helped me be more creative in how I approach jobs. At one point I was making as much as my friends who graduated with degrees (and more than a couple of them). But, dropping out was motivated by happiness for myself rather than "I'm going to start a business and be rich". I think the reason why you drop out and what you're looking for because of it ultimately defines whether you'll regret it or not.