#300 · should you drop out of college?

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Sunset Cliff asks: Should I drop out of college to focus on AI automation and entrepreneurship? I’m a business student with no interest in finance/banking, have grandparents covering tuition, make ~$10k from AI automation, and want to know how to decide if leaving school makes sense for my insurance‑niche venture.

I finished my degree and looking back I don’t think I really needed it—I did it mostly to satisfy my family and friends. I was basically just treading water, lacking the conviction to make a real bet in life. As you get older and more successful, you realize you need to take bets and be ready if they don’t work out; it’s better to have tried and failed than never tried at all. In my case, a bet would have been dropping out to run a business full‑time; for you, it might look the same—leaving school to focus on your AI automation and entrepreneurship venture. Beyond personal experience, remember that colleges were originally designed to train you for a specific job, but today they’ve become mostly marketing machines that promise a future without delivering the skills or ROI. Most of the value you get is the social experience—being forced to interact with peers and learn soft skills. You can get that social side elsewhere, and there are many other ways to meet people without spending years and tuition money. So, weigh the social benefit against the cost and your own goals; if the credential isn’t essential for what you want to do, dropping out to pursue your business may be the smarter bet.

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Related answers

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What are your thoughts on going to university and getting a job? Is it harder than what you're doing right now? Why is higher education losing its perceived value?

I think it's actually much easier than university. The main difference is that university requires a lot of courage to follow a well‑worn path, whereas building an automation info product takes courage to do something no one else is doing. Higher education is losing perceived value because the actual value has been eroding for the last 20 years. The internet now provides free resources that let anyone learn what a degree used to guarantee, so a degree is no longer the primary signal of knowledge or skill. What matters now is what you do with your time outside of school.

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As an 18‑year‑old passionate about tech and AI, I’m stuck in self‑doubt about whether automation is real, if people will pay, and if this path is worth betting everything on; how did you push through doubt and lock in your path?

I don’t have everything figured out, and neither do the most successful people. At 18, committing to a path might only mean a few months of your life, not your whole adult life. Treat it as a season—give it an honest go, make something happen, or decide it’s not for you; that’s totally okay. The people who succeed see business as enjoyable play. You just need to push through until you get a positive result, which will dissolve the self‑doubt.

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As an A‑level student studying physics, math, and computer science aiming for a compsai path, is pursuing a university degree the right way to optimize for money, or should I focus on entrepreneurship to avoid financial struggle?

College was a great experience for me and it helped, but you don’t need a degree to succeed. What matters is being clear about what you want to do before you enroll. You’re already doing the right thing by thinking about life after college instead of just picking a random degree. Remember, college isn’t a life‑or‑death choice—many successful people treat business as enjoyable play. The key is to push through until you get a positive result, which will erase the self‑doubt.

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I know people who've quit full-time careers to pursue AI automation agencies, and it seems risky given how fast AI is advancing — many tasks automation agencies do could become redundant as AI gets more agentic. What's the future of AI automation agencies, how long before it becomes obsolete, and what would you pivot to if it did?

I wouldn't quit a full-time career to pursue automation unless I was hitting parity with my salary consistently for a few months, ideally more like 2-3x it. But the underlying assumption in this question — that a career is more stable than self-employment — isn't actually true; a career is more *predictable*, not more *stable*. It's simple math: with a $25K/month career built on one employer, losing that job means losing all $25K. With a $25K/month agency spread across three clients, losing one client only costs you $8K — diversification is the only free lunch in life and investing, and more clients (or more income sources generally) is inherently more stable than fewer. That said, employment does have real benefits automation work doesn't: unemployment benefits, standard employee protections (can't be fired without cause after a certain point), and other regulatory guardrails that don't exist for the self-employed.

career vs self-employmentdiversificationai displacement fears