"Five years from now..." is a pretty good benchmark for the half-life of most business or career-related arcs (okay, maybe 5-10 years, depending on the career or industry).
As an undergrad or fresh grad, of course your undergrad matters - to you, to your peers, to recruiters, to your parents (if you have helicopter parents that is). Beyond 5 years, it doesn't.
As a b-school student and recent grad, your MBA matters for a while, but peters out within 5 years or so.
When you're in your mid- to late-30s (which to most undergrads may seem "old" but is not) - it's again what you've achieved in the last 5 years that factors into most decision-making (whether to hire you, invest in your company, etc) and far less if any what you did in your 20s.
In your 40s, no one cares what you did in your 20s or a decade before in your 30s for most cases. And so forth.
That's why the "what have you done for me lately" world is a double-edged sword: you can't rest on your laurels from long ago, but any failures are also long forgotten as well.
If there's one piece of advice I *know* from experience (and those I know) that I could give to undergrads and those who are early in their career, it's this:
Be prepared to reinvent yourself. At least a few times in your lifetime. From my own experience and those of my peers (now in their 40s and 50s), especially how the economy has sped up considerably (even more than 10-20 years ago), be prepared to start over faster than you think.
Treat every career like it's an NFL career: short-lived. You will get replaced by younger and cheaper players (and if you join the coaching staff, be prepared to be fired multiple times). And count on this happening every 5-10 (maybe 15?) years or so. Where you have to start over.
Sometimes there's no choice - it's 2008/09, you get fired from a finance job that won't return, so you start a new career.
Sometimes it's a huge change in your personal circumstances - marriage, divorce, kids, death in the family, unexpected healthcare issues with you or your loved ones.
Other times it's existential - you hate your career/life, you need a complete change, or you have some sort of wake up call, scare, or you discover a calling.
The prestige on your resume isn't going to protect you from this, nor is it going to help as much as you think - ESPECIALLY once you're in your late 30s and beyond when the world sees your 20s as "childhood" and heavily discounted.
And ask anyone who has had to do a complete 180 in their career/life - it's not easy. There's a hangover period, a transition period of sorts where you will be scared. But just know that it's an unavoidable fact of life.
Stop focusing on prestige, safety and guarantees - because it's not going to pan out. I'm not being pessimistic. It's a fact of life and the odds are stacked against it working out the way you have envisioned it in your mind. Maybe this job you've envisioned is cushy and takes you beyond b-school for the 2 years. But then what? You think you're all set up for the rest of your life? Here's what WILL happen: you will have to pivot, and pivot hard, at least a few times in your life - maybe it's by force, or by choice, but it WILL happen where you essentially have to start over. And no matter how hard you try to play God in your own life, it's unavoidable: sometimes you see your career ending like a terminal disease, other times it's sudden death.
So instead, build the skills for how to reinvent yourself. Being able to start over, reinvent yourself is going to be most important. And that comes down to one thing:
Curiosity - not many people are as curious as you think. Especially business types at a young age: obsessed with money, prestige, power and playing God in their fantasies. These folks have focused only on learning what they deem will be useful. Being truly curious means learning for the sake of learning - yes you have to balance between being a dilettante and being obsessive, but it's more a state of mind: to constantly challenge and learn about new people, experiences, etc. Learn a new instrument. A new language. Or take a cooking class, dance class, etc. And the more you can get into that habit now, the better, because as you get older and settle in, it's harder to do that. This state of mind and being willing to "be the beginner" is an important muscle that becomes crucial when you have to "be a beginner" when the stakes are higher: when you have to start over. You will find as you graduate and get into the workforce, a lot of people want to be the expert (or pretend to be), but are terrified of being a beginner, or being seen as a beginner.
When you are afraid of being a beginner, you are afraid of learning new things. When you are afraid of being a beginner, you are afraid of the small failings along the way, which only makes any large potential failing that much more terrifying.
Mod Note (Andy): Best of 2016, this post ranks #18 for the past year