You are getting ready for a trip to Florida. It’s your first vacation in forever, and you couldn’t be more excited; no work, no stand-ups, just a week of sun and relaxation.

You’re even going to pack your bags a day in advance, that’s how excited you are! Your flight is on Tuesday, and usually you end up making a game out of how much stuff you can fit in your weekender before the Uber reaches your apartment; but its a Monday evening, and you’ve finished cleaning your apartment and you’ve got your bags out on the table and everything.

You start with the basics:

  • A half-dozen pairs of briefs
  • Some tees
  • Some tanks
  • Some shorts
  • Some sandals

You realize there are some other things you might need: you’ll probably go to a semi-nice dinner, so you throw in a pair of linen pants and a button down. Oh, and a belt and some nice shoes. And it’s been shitty in Seattle the past couple weeks and your legs are yearning for some cardio, so you wanna go running — in goes a couple pairs of gym shorts and your running shoes.

You remember Mom mentioned that it’s been raining in West Palm the past couple days, so you throw in a lightweight Uniqlo rain jacket. But, now that you realize it, you don’t really have any outerwear going on at all — might as well toss in a hoodie in case it gets cold (plus the airplane is always chilly).

And you and Dad might try and catch a game while you’re down there, so you throw in your Wade jersey and a Landry long-sleeve.

Oh, and probably some sweatpants! But that’s it. You’re packed.

With a couple minutes of effort, you manage to close the zipper holding everything together. Your bag looks as if it is ready to burst at the seams.

That’s just clothes, though. You need something to do on the flight and during downtime and such, so you start pouring stuff into your messenger bag. You start with your laptop (because, come on, who are you kidding) and the three latest New Yorkers that you’ve only read a couple articles from. Toss in your Kindle for beachside reading; and might as well throw in the iPad mini, too, since you’ve got a couple iBooks laying around and have been meaning to knock out the Monument Valley expansion. And you promised yourself you wouldn’t, but you decide to fit in your work laptop too — just in case something comes up, you know?

Okay, that’s the big stuff out of the way. Now it’s just the small pieces:

  • a Moleskine, for notes
  • a pocket book of crosswords
  • a battery pack even though Google Flights says you have A/C power on both flights because you’ve been burned by that before and nothing is worse than trying to kill three hours by reading Delta’s in-flight magazine
  • a handful of pens and pencils
  • a copy of The Beautiful Struggle and The Art of Reading, for a little injection of non-technology
  • a rat’s nest of chargers. Oh god, so many chargers.

It looks like your messenger bag just finished Thanksgivings dinner. You sigh happily, knowing just how productive you can be on the plane.

You waddle out of the apartment, your weekend ready to burst and your messenger bag digging angrily into your clavicle. Later, at the airport, you are told you’ll have to check your weekender — it’s too large to fit in overhead storage.

You end up running, like you wanted to — but you never end up going anywhere fancier than Mario the Baker’s for dinner, so the khakis were kind of pointless. Also, at some point you decided it was wise to pack three button downs?

You didn’t get much reading done — opting for a playthrough of Final Fantasy 6 as an indulgence of mindless consumption — but you did finish up The Beautiful Struggle, and made a minor dent in your New Yorker backlog. Still, it looks like your laptops end up crushing and crinkling your books, and now your secondhand copy of The Art of Reading is a little (more) beaten up on its corners. And hey, your battery pack is still at full charge!

You resolve that, next year, you’ll pack less. You probably didn’t need so many tank tops.

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