What's In My Bag
Packing for a work retreat in Mexico. Everything I need to be productive, sleep well, stay healthy, and have a little fun, all in a carry-on.
I only ever travel with carry-on.
That's a rule I set for myself a while back, and it forces you to think about what actually matters. When the Agility exec leadership team planned our retreat in Mexico, I knew the drill: figure out what I need to be productive, get a good sleep, stay healthy, and have a little fun. Pack it all into one bag. Leave the rest behind.
I made a whole video about this, actually. The full gear breakdown is right here:
But let me walk through the thinking behind it.
The Bags
My carry-on is the Monos hybrid (the gray one). Solid, not too heavy, rolls well. I've looked at the Peak Design Roller Pro, which would match the rest of my kit, but it's expensive and this one works. Maybe someday.
For my personal item, I use the Peak Design Everyday Messenger. This bag is incredible. The latch alone is a work of art. Passport pouch right where you need it, a spot for sunglasses, separate sleeves for both a laptop and an iPad. I've reconfigured the inside of this thing probably a dozen times, and it just adapts to whatever I need.
The Tech
My iPad Pro M4 goes everywhere with me. I use it with the Apple Pencil Pro (with a little holder nub from Paperlike) and an Astropad screen protector that makes it feel like writing on actual paper. The Logitech Combo Touch case is, honestly, falling apart, so I think the new Apple Magic Keyboard with the aluminum base is next.
The MacBook Pro 14-inch M3 Pro is my main work machine. A couple years old now, more than enough power for anything I need to do. I also bring my Logitech Master 2S mouse, because if you have to jump into a support issue or do some real work, a trackpad only gets you so far.
AirPods Pro 2 for the plane. The noise cancellation alone justifies their existence. I haven't tried the Pro 3 yet, but these still do everything I need.
Sleep, Reading, and Fun
Getting a good sleep when you travel is everything. One of my best packing decisions is the Kindle Paperwhite. You can fall asleep reading off that e-ink screen so much easier than staring at your phone. It makes a real difference.
And then there's the Nintendo Switch 2. I don't use it that much, but it doesn't take up that much space either. Playing a racing game during turbulence on a plane is its own kind of experience.
Powering It All
The UGreen 100-watt charger is the MVP of the whole bag. Three USB-C ports and a USB-A, which matters because most hotel rooms still only have USB-A outlets. This thing charges everything. I have a separate one for Europe, but for Mexico, this guy handles it.
I also carry a 3-in-1 travel charger that does my iPhone, Apple Watch, and AirPods all at once. And for the Sonos Play speaker (which is brand new and sounds absolutely fantastic), I put it on its own dedicated Apple 30-watt charger.
The Sonos and the DJI Mic
Two items that aren't strictly "necessary" but make the trip so much better. The Sonos Play speaker sits between the Roam and the Move in size, and the sound quality is wild for something this portable. I probably spent a little too much on it. I don't care.
The DJI Mic Mini 2 is what I recorded the video with. If you're making any content on the go, this thing cuts out background noise like magic. I used it on a train trip to Ottawa recently and it handled a noisy hotel room like a champ.
The Actual Trip
The resort is something else. The room has a freestanding bathtub just sitting there in the middle of everything, which feels both luxurious and slightly ridiculous.
But we're here to work. Jon and Jina from the exec leadership team are here, and we've already been deep in sessions about where Agility is headed. There's something about getting out of your normal environment that changes how you think about problems. You stop defaulting to the same patterns.
Pack for the Trip You're Taking
The whole point of packing carefully isn't minimalism for its own sake. It's about having exactly what you need so you can focus on why you're there. Good sleep, good tools, good conversations. A speaker for music at the end of the day. A Kindle for winding down. A Switch for the plane.
Everything earns its spot in the bag, or it stays home.
P.S.: apologies for the hilarious AI remixed hero image on this one... ChatGTP really outdid itself...
This is what I think about
Technology, creativity, how teams work, what makes things good. I write about all of it. Stick around.