There’s a counterintuitive path to success that nobody talks about: if you skip college, you should be sprinting toward financial independence by your late twenties. Not because 28 is some magic number, but because it creates optionality that changes everything.
Most people think the choice between college and not going is permanent. You either get the degree early or you’re forever locked out of that world. But that’s not actually true. What is true is that going back to school at 35 with a mortgage, two kids, and mounting responsibilities is brutally hard. Going back at 28 with enough money in the bank to not worry about tuition or living expenses? That’s a completely different game.When you graduate high school and enter the workforce directly, you have something college students don’t: a five to seven year head start on earning and building wealth. While your peers are accumulating debt and drinking cheap beer, you can be accumulating assets and learning how money actually works. This advantage is enormous, but only if you treat it like the limited-time opportunity it is.
The window between 18 and 28 is uniquely suited to aggressive wealth building. You likely don’t have dependents yet. Your lifestyle expectations are still flexible. You can live with roommates, drive a used car, and work seventy-hour weeks without anyone questioning your priorities. Most importantly, you can take risks. This is when you can start a business, take commission-only sales jobs, learn high-income skills, or make unconventional career moves that might not pan out.
The goal isn’t to become a millionaire, though some will. The goal is to build enough financial cushion that you have real choices. Maybe that’s $100,000 in investments, maybe it’s a paid-off rental property, maybe it’s a business that generates passive income. The specific number matters less than reaching a point where you’re not living paycheck to paycheck and could afford to pause earning for a few years if you needed to.
This cushion transforms the college question from a now-or-never decision into a strategic choice. At 28, with money in the bank, you can evaluate whether a degree would actually improve your trajectory. Maybe you’ve discovered that real estate development is your calling and an architecture degree would open doors. Maybe you’ve hit a ceiling in tech and a computer science degree would break through it. Or maybe you’ve built something successful enough that college would be a step backward.
The beautiful part is that returning to school from a position of financial strength changes the entire experience. You’re not there because society said you should be or because you didn’t know what else to do. You’re there because you’ve identified a specific knowledge gap that’s blocking your next move. You can be selective about programs, negotiate better financial aid from a position of strength, and actually focus on learning instead of stressing about how you’ll pay rent.
There’s also a psychological element that’s easy to overlook. Watching your college-graduate peers enter the workforce at 22 or 23, often in entry-level positions paying $45,000 while carrying $80,000 in debt, fundamentally changes how you think about the value proposition of education. By 28, many of them are still trying to get their financial lives together. If you’ve spent that decade building wealth, you’re not bitter or regretful about missing college. You’re calculating whether it’s worth the opportunity cost.
This path requires discipline that most 18-year-olds don’t have. It means watching friends blow their paychecks on concerts and weekend trips while you’re maxing out a Roth IRA. It means choosing the higher-paying job over the more enjoyable one. It means being the weird one who reads personal finance books and talks about compound interest at parties.
But the alternative is drifting through your twenties, spending what you earn, and waking up at 32 realizing you’re trapped in whatever circumstances you’ve created. At that point, going back to school feels impossible. The opportunity cost is too high. The responsibilities are too heavy. You’re stuck.
There’s no guarantee this strategy works for everyone. Some careers genuinely require degrees upfront, and no amount of wealth building will change that. Some people will build financial security and still never feel compelled to get formal education. That’s fine. The point isn’t that everyone should go to college eventually. The point is that keeping that option open requires acting with urgency in your early twenties.
The 28-year target isn’t arbitrary. It’s late enough that you can accumulate real wealth and figure out what you actually want. It’s early enough that returning to school doesn’t feel like you’re starting over. It’s the inflection point where your peers with degrees are finally getting established, and you can decide whether joining them makes sense or whether you’ve already built something better.Skip college if you want. But don’t skip the wealth building. Your 28-year-old self will either thank you for creating options or resent you for squandering them. The decade between 18 and 28 is too valuable to waste assuming everything will work out. Make it count.