Plannerman

I’m flying out to LA with my wife and daughters to see our son, and this is the part I actually love. I’m a great planner, to the point where my kids call me Plannerman. It’s not exactly a compliment, but it’s not wrong either. I handle the flights, the cars, the hotels. I like knowing where we’re staying, how we’re getting there, and what time everything happens. I can see the whole trip in my head before we even leave, and I look forward to it more than I probably should.

Then the day comes, and everything shifts.

It’s not the flying that gets me. I don’t think about the plane at all. What gets me is everything leading up to it. The house feels different that morning, like it’s in transition. Bags are open, cords are spread across the counter, and I’ve printed things that are already sitting on my phone because, for reasons I can’t fully explain, I don’t trust my phone when it matters.

Packing is where it starts to go sideways. Nothing seems to have a natural place. I’m trying to put things into sections of the suitcase that don’t feel like they belong there. Chargers end up with shoes. Papers get slid between clothes like that somehow makes sense. I’ll zip it up, open it back up, move three things, and convince myself that this version is better. It’s not. It just feels like I did something.

I know exactly where the passports are, and I still go check. I check the back door, lock it, feel it click, and walk away. Then I stop, turn around, and check it again. Then one more time, just to land it. I do the same thing with my pills and the passports. Three times. Not two. Three is the number that apparently keeps everything from falling apart while we’re gone.

My wife watches me do this like she’s seen a rerun enough times to know how it ends. She doesn’t say anything anymore.

By the time we’re standing outside to get our Uber (Because you cannot do that inside), everything has been checked, confirmed, and packed, and it still feels like I missed something obvious. Something small that will absolutely matter later.

As we wait, and I’m locked in on the screen, watching the little car move toward us. I’m not even really listening to my wife at this point. I’m watching the route, the timing, the distance, like if I stare at it long enough it will behave. It gets close, pauses, and then disappears. The driver cancels. Of course he does. Now we’re standing there with bags at our feet, watching the time move forward while I pretend this is fine and not the beginning of a complete unraveling. Another driver picks us up and we start over.

The airport is twenty minutes away, but that drive stretches out in a way that makes no sense. Every light feels longer than it should. I’m watching the clock, doing the math over and over, adjusting arrival times in my head like I can somehow bend time if I stay focused enough. This is where I go quiet. Not angry, just… not a great version of myself.

Which is ridiculous, because I’ve actually blown this before.

One time as we drove into the airport the driver said he didn’t see Southwest anywhere on the signs. I remember thinking he was wrong, then looking up and feeling that slow drop in my stomach. We were supposed to be at Midway. We were at O’Hare. There’s a moment where nobody says anything, and then suddenly we’re telling him to go as fast as he can like we’re in The Amazing Race.

Another time I missed a flight because I thought it was the next day. I still don’t understand how that happens with how many times I check things, but it did. I made the family miss a day of vacation. So clearly, whatever system I’ve built here is not flawless.

At the airport, I go straight to the skycap because I want a person. I want someone to take the bag, look at me, and tell me I’m good. It doesn’t solve anything, but it takes the edge off just enough to keep moving. Thats worth a $5 bucks a bag for me.

Then TSA takes over, and it’s never the same twice. Shoes, belt, bins, instructions that feel like they’re being made up in real time. My replaced hips set off certain scanners, so now I’m in another line, waiting again, with plenty of time to think about everything that might be wrong.

I pile on more thoughts. What if something didn’t go through. What if something didn’t scan. What if I missed something small that turns into something big. It all stacks up, one on top of the other, and there’s nothing to do but stand there and wait your turn.

Then I step through the scanner.

I grab my things on the other side, and I can feel it happen almost immediately. My shoulders drop, my breathing slows down, and the noise in my head just… stops. I’m standing there putting my belt back on, sliding my shoes on, picking up my bag, and I’m back.

Because at that point, it’s not on me anymore. I got us there, I didn’t miss anything, and nothing blew up. From there on out, it belongs to the airline, the system, the people running it.

My part is done.

So if you see me standing off to the side after security, not moving for a second while everyone else keeps going, just taking a breath before I head to the gate—give me a nod knowing I made it.

About Greenland Sharks

Greenland Sharks is a Chicago men's group who value friendship, experiences, and the long swim. Just a crew that shows up. No speeches. No name tags. No nonsense.

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