True, imitation high school -- even the Hellmouth that was Sunnydale High in Buffy the Vampire Slayer -- can never approach the horror of the real thing. When I was 15, one of my mother's bridge-playing friends patted my hand and declared, "These are the happiest days of your life." I shivered: "It gets worse from here?"

Well, no. It gets progressively better, even as many patterns repeat.

Dating at 45 is just as silly and awkward and potentially thrilling as dating at 15. It never gets easier. Starting a new job invokes the same butterflies as the first day of school, except you have to worry about the right 401(k) instead of the wrong backpack. Filling out your Schedule A is a lot like a midterm -- although getting a refund is more satisfying than pumping up your GPA.

Start planning your escape
As you get older, the good news is:

  1. You never, ever have to sweat about getting into college again.
  2. You can permanently escape your shy, clumsy, dweeb status and become a Cool Kid.

Some of this is automatic. When you're within range of the AARP, you stop pretending that you don't care what people think. You actually don't care what (most) people think. It's very relaxing (and more effective than Botox for retaining your youthful complexion).

Some of this takes more prep work than the SATs. You have to get over the shock of turning 30, or 40, or 50, and connect the dots that take you to age 60, 70, 80. even 100. The way -- the only way -- to put yourself in the calmly superior position of my parents, cheerfully spending my inheritance on Alaskan cruises, is to start piling up a cash cushion. As much as you can. As early as you can. And just keep on truckin'.

Don't panic
"Don't panic" is what A Hitchhiker's Guide to the Galaxy tells us. That got me through the senior prom, and as I squint at the future through bifocals, I find the advice is still working. (Don't tell anyone at The Motley Fool: they're rimless.) Beyond "bring a towel," though, A Hitchhiker's Guide is a little short on specifics. The film was released in London on April 21; it is due to hit U.S. theaters this weekend. Touchstone Pictures, owned by Disney (NYSE:DIS), is usually reliable, but I guarantee you that Douglas Adams' book is better.

So, you want specifics on cruising toward retirement?

  • Never pass up free money. Contribute to your company's retirement plan up to the limit that it matches contributions. Then, feed a Roth IRA.
  • Pick a strategy. Instead of buying a few stocks here or there, or just accepting whatever's in your company's 401(k), get a real asset allocation strategy. That way, you can get more upside profit and less downside loss for the same amount of money.
  • Make a plan. Develop a plan for what you'll actually do in retirement. "All dressed up and no place to go" was sad in high school. In retirement, it's pathetic. Even life-threatening. (No kidding. Everybody has an Uncle Fred or Cousin Gertie who dropped dead within a month of the Gold Watch Lunch. Just tough luck? I don't think so.) Maybe it's time to consider a second -- or third -- or fourth -- career.

This time, you can see what's coming
High school taught us all that periods of euphoria are followed by long periods of ennui. If someone had told you that in sixth grade, you probably wouldn't have believed them. You couldn't see that far ahead, and you had no real way to prepare for anything, anyway.

Now it's different. Even if you haven't figured out what you want to be when you grow up, you know (deep in your tendons) that you're getting older. You're even going to get. old. Barring the regrettable alternative, everybody is.

Escape eternity in high school
Everywhere you look, you see scary statistics about Americans and retirement. Three out of four baby boomers are underprepared. An alarming percentage -- nearly half -- is almost completely unprepared. Which should tell you that:

  1. Most of your peers are clueless. In the years to come, they're going to have all the maneuvering room of the average gym locker.
  2. You can ace this thing, because you can see what's coming before it comes at you.

Fundamentally, all that separates the dweebs from the cool kids is a little edge -- and a lot of attitude. The cool kids look confident. (They may be jelly inside, but they look confident. Which builds on itself.) They're more than a little pushy. And...

They're unafraid
That's what really separates the men from the boys and the girls from the wimmin. The truly cool face facts -- especially unpleasant facts. They take risks. They don't wait for events to overtake them. And they ruthlessly exploit every advantage they can. Advantages like the Motley Fool Rule Your Retirement newsletter service.

Knowledge is power
Sister Mary Francis was right: Knowledge is power. And it's ridiculously easy to come by. Because this time, it's perfectly OK to look at somebody else's paper -- like Robert Brokamp's Rule Your Retirement. Robert's willing to do most of your homework for you. And he'll even let you look over his shoulder -- to get started, click here for a free 30-day trial.

How cool is that?

Melissa Ennis has been advanced for her age since she turned 11. (Same height, too. That explains a lot.) She does not own shares of any company mentioned in this article. The Motley Fool is investors writing for investors .