Stanford double dropout (undergrad + grad) reporting in - one piece of anecdata:
Middle class Taiwanese family of white collar parents.
Went to undergrad, dabbled in a few side projects and dropped out to work at a game company, a startup as an employee, and my own startup, in that order.
Learnings: found out I knew very little, and the branding/network/advice I could get from school would save me from reinventing the wheel over and over as a unvetted/newbie entrepreneur. This is hugely important and people don't assign enough value to it. For things where you need someone to hire you: you need to convince them somehow, and getting that piece of paper helps cover their butt and makes their life easier. I went back to school to have a bit of optionality.
Graduated and was planning on doing grad school. Spent first quarter basically playing D&D and League and barely scraped by academically, spent a few weekends hanging out with fellow Burners at a theme camp and collaborated on a few projects. I dropped out (for good this time) and pursued them -- all of them failed in the next 2 years, but what was useful was that I learned who were the good cofounder/advisors and how this kinda opaque process worked. Hit both a good startup as an advisor/early employee, then cofounded a cashflow business that I then bought out and proceeded to run for a decade.
Learnings: Knowledge and network are filled with plenty of opportunity costs -- and there's ways to make it both as a generalist and a specialist... ideally you can optimize for the intersect of what you want and what the world wants, and that ends up being the hard part. My own path was largely unplanned and opportunistic -- by hanging around an area of opportunity long enough and being ready I was able to access enough things to mildly succeed (didn't hit the stock jackpot, but I have a reasonable business).
Back to the question: the article answers it in the first few paragraphs - it depends on the person but is usually the "harder way". I only took the path because I had the priviledge/luxury to chase what I wanted, despite the vague expected value.
Middle class Taiwanese family of white collar parents. Went to undergrad, dabbled in a few side projects and dropped out to work at a game company, a startup as an employee, and my own startup, in that order.
Learnings: found out I knew very little, and the branding/network/advice I could get from school would save me from reinventing the wheel over and over as a unvetted/newbie entrepreneur. This is hugely important and people don't assign enough value to it. For things where you need someone to hire you: you need to convince them somehow, and getting that piece of paper helps cover their butt and makes their life easier. I went back to school to have a bit of optionality.
Graduated and was planning on doing grad school. Spent first quarter basically playing D&D and League and barely scraped by academically, spent a few weekends hanging out with fellow Burners at a theme camp and collaborated on a few projects. I dropped out (for good this time) and pursued them -- all of them failed in the next 2 years, but what was useful was that I learned who were the good cofounder/advisors and how this kinda opaque process worked. Hit both a good startup as an advisor/early employee, then cofounded a cashflow business that I then bought out and proceeded to run for a decade.
Learnings: Knowledge and network are filled with plenty of opportunity costs -- and there's ways to make it both as a generalist and a specialist... ideally you can optimize for the intersect of what you want and what the world wants, and that ends up being the hard part. My own path was largely unplanned and opportunistic -- by hanging around an area of opportunity long enough and being ready I was able to access enough things to mildly succeed (didn't hit the stock jackpot, but I have a reasonable business).
Back to the question: the article answers it in the first few paragraphs - it depends on the person but is usually the "harder way". I only took the path because I had the priviledge/luxury to chase what I wanted, despite the vague expected value.