You Look Good Wearing My Future

You wouldn’t necessarily think of Some Kind of Wonderful as an inspirational movie.

Not in the way you might think of Dead Poets Society, for example, or some other movie from our dearly departed childhood that was very clearly designed to make you feel like you should seize the day.

But lately I’ve been thinking about Some Kind of Wonderful.

Mary Stuart Masterson. Eric Stoltz. Lea Thompson. Elias Koteas (who’s name I have apparently spent my entire life being unsure how to pronounce, but who played Duncan, one of the greatest supporting characters in an ’80s movie).

But the reason I’ve been thinking about the movie isn’t really nostalgia.

It’s the ending. And it’s where we are right now.

I don’t know about you, but my algorithm is showing me a shit-ton of people in their 50s and 60s basically saying: “Fuck this. I’m out.” People getting fired from jobs they’ve had forever. Other people walking away from careers.

People realizing they don’t actually want to spend the rest of whatever time they have left doing the thing they’ve been doing simply because they’ve already spent thirty years doing it.

Some of them know exactly what they’re going to do next. A lot of them don’t.

And at this particular moment in history—and at this particular age—I find that fascinating.

So why Some Kind of Wonderful?

I’m not going to spoil the ending because I recently discovered there are somehow still Gen Xers who haven’t seen Pump Up the Volume, which means I’m no longer going to assume everybody our age has seen every movie I saw forty-seven times on HBO.

But I will give you the last line. At least, the last line as I remember it:

“You look good wearing my future.”

That line hits differently now. Because part of what Some Kind of Wonderful is about is a kid being told what he is supposed to do with his life.

What he’s supposed to want. What he’s supposed to do with his money. What constitutes a smart decision. What the next step is.

And Keith finally reaches this point where literally shouts:

“When does my life belong to me?”

I wonder how many of us are asking some version of that question again at fifty (plus).

Because we spent decades being told how things were supposed to work.

Be responsible, get the job, keep the job, buy the thing, save the money, climb the ladder, follow the rules. Eventually you’ll arrive at whatever “success” is supposed to look like.

Except demonstrably, for a whole lot of people, the system we were told would work does not work that way at all. The world seems to finally be waking up to this fact.

So maybe you reach a point where you say: Yeah. I’m going to make the quote-unquote dumb choice.

With my money. Or my job. With where I live, with what I create.

And I’m going to trust that somehow I’ll figure it out.

Now, we could have a whole debate about whether that’s smart or stupid or financially responsible or reckless or whatever. I am definitely not telling anybody to blow up their life because a John Hughes movie told them to.

If you are not in a safe place to make a gigantic life decision, don’t make one.

Seriously. My own family is getting ready to make some big fucking choices, and I am scared to fucking death.

But I also know this:

One day I am going to be dead.

And on my way out, if I think about the things I am most likely to regret, they are not going to be the things I tried that went badly.

They are the things I never tried at all.

The version of my life I never got to meet because I was waiting for somebody to tell me it was okay.

And suddenly:

You look good wearing my future.

You don’t have to drain your bank account and go buy diamond earrings or quit your job tomorrow morning.

But Gary Vee said something once that has stuck with me for years:

“You did not exist for a very long time. And you are going to not exist for even longer than that.”

Sit with that sometime. Seriously. Pour yourself a cup of tea or a beer or a glass of wine or whatever you drink and just sit with it.

Not in some grim, nihilistic way. Just as a fact.

You got this weird little window.

Go watch Some Kind of Wonderful. Enjoy the hell out of it. Let it take you back. Let yourself feel whatever it makes you feel as an Xer—or whatever generation you happen to belong to.

And then think about the thing you’ve been thinking about.

Really think about it.

I’m going to keep writing books. Pulp fiction for 90s kids, quasi-literary YA, all kinds of stuff. Because I don’t think I’ll regret it.

I write about teenagers. I write about monsters. I write about the years that made us.

Sometimes those are three different things. Sometimes they’re the same thing.

But I’ll keep doing it because they are stories about who we were, what happened to us, and what we became.

Often, with a hat-tip to stories like Some Kind of Wonderful.

You look good wearing my future.

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