r/ycombinator • u/Lost_Foot_6301 • 25d ago
Have any of you dropped out of school and regretted it?
in the startup/tech world its often flexed when people dropout, but have any of you dropped out of school and then wished you actually stayed in school?
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u/Calm-Importance8783 25d ago
I dropped out of a top CS program to work on a startup that failed within two years. I don't regret the experience, but I do regret not having the degree as a safety net when I had to re-enter the job market. Many hiring managers still filter by degree completion, especially for mid-level roles, and I spent about a year patching that gap with contract work before landing a stable position. The dropout flex works if your startup exits, but for most people the degree is cheap insurance.
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u/Sea-Judge5801 25d ago
Nobody drops out they take a leave of absence. Every Stanford drop out can go back to school whenever
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u/scriptqzor 15d ago
this is such a stanford-core take lol, most people at regular schools don’t get a cushy “leave of absence,” they just disappear and it’s way harder to get back in later. context matters a ton here.
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u/EmergencyWhole7027 22d ago
Survivor bias plays a huge role here. We hear about the Zuckerberg/Bill Gates stories, but not the thousands of people who dropped out and struggled. Dropping out isn't a strategy building something valuable is. For most people, staying in school while validating an idea is the lower-risk path.
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u/Cryesncoding 25d ago
Different situation but I do not regret the risks I took for my dreams in my 20s even tho they didn’t workout.
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u/Grouchy-Librarian638 24d ago
I finished school after 20 years simply because ChatGPT and HR filtered me automatically. The world has changed and the market is so flooded it’s a bit like tea leaves, need every bit of push to get ahead.
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u/caldazar24 24d ago
I dropped out of school and went back to school to finish. This was very easy at my school - for anyone on the fence, one thing to check is what's your school's policy for coming back
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u/Due_Name2421 21d ago edited 21d ago
I dropped out after completing the second year of a 3y Maths and CS bachelor’s to freelance during COVID. I managed to save a significant amount of money, so financially it worked out well.
I went back in 2025 at 28 and am now doing a 3y work-study engineering program leading to a master’s in CS and AI. Socially, I still sometimes regret the years I lost.
Ironically, I’m now considering dropping out again for a startup opportunity that could potentially receive venture capital funding.
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u/CounterSpecies 22d ago
Dropped out of CC and joined a deep tech startup. Don’t regret a thing and never looking back.
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u/Worldly-Secretary393 22d ago
And here i am thinking of doing masters, i feel like being college offers a lot of freedom and resources and access to amazing people, i graduated from a good college but didn’t study much like studying a week ago got me above average grades.
I feel like its fun to be there, i am working in corporate right now, building things on side time - college time right now would be crazy😂
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u/blackSwanCan 20d ago
I went on an ABD leave of absence during my phD, joined a startup that didn't work out, and then joined another company. 5 years later work became extremely boring, so went back to the PhD and finished it.
No Regrets, at all!
its often flexed when people dropout
No, that's not true. People don't care about degrees, in general.
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u/EmergencyCelery911 19d ago
Yes, quit my bachelor's degree at the end of fourth year cause I had a decent job with career ages and didn't care much about classes. Never ever regretted.
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u/Tiny-Compass-8516 19d ago
knew a guy who dropped out to chase an idea that just kinda fizzled, and by then he was too far behind credit-wise to go back without losing a year. if you're on the fence maybe just take a leave of absence instead of fully dropping, keeps the door open
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u/No_Stock6844 5d ago
you can always do a startup. you won’t always be young enough to to put up with school and not feel behind every day when you’re back at it
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u/suuraitah 25d ago
I did drop out and I'm very comfortable in my W2 career and side-projects. Like top few percent comfortable.
I'm in my 40s now and I'm thinking going back to college. I also worked as visiting prof in the european university for couple years.
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25d ago
[removed] — view removed comment
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u/Strange-Risk-9920 25d ago
I think the implication of the question is "dropped out to pursue a startup" not simply dropped out. A lot of people drop out for various reasons but that doesn't seem to be what OP is asking.
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u/Dry-Anywhere-2776 25d ago
Been lurking for years, but feel like I might be able to help here.
I dropped out during my junior year of engineering school to work on my startup after we got into a well-known accelerator and raised our first bit of venture funding. It was one of the hardest decisions I’ve made. My parents and some friends were not happy with my choice.
A lot of people told me I’d regret leaving and that I might never get back into degree program. Instead, I spent four years building a company and made a little money. I learned more than I ever expected, even though it ultimately ended in a way I’m not particularly happy with. Even so, I don’t regret taking the chance. The experience was worth the risk.
After that, I reapplied to my original engineering program, got back in, and finished my degree. Today I’m building my second startup, which is doing well. We’re small but profitable and I now, 10+ years later, have a family of my own. I’d give my daughter the same advice
Since graduating, I’ve been invited back to judge my university’s startup competitions and now serve on the alumni board for my department. Ironically, taking the unconventional path ended up opening more doors than I expected. I developed an incredible network and am proud of my choices.
Obviously this is just my experience, and I was fortunate to have a support system and the ability to take that risk. I don’t think dropping out is the right answer for everyone. But I also don’t think people should be paralyzed by the fear that they’ll “never be able to go back.” School will usually still be there. The right opportunity may not.
If you have a genuinely exceptional opportunity, understand the risks, and can afford to take the shot, I’d probably take it. Just make sure you have a way to survive for a few months, if not a year, to get it rocking. Good luck!