This past week, I traveled to New Orleans for a work meetup with my Happiness Engineer team. It was an incredible experience with a lot learning, amazing food, and games. I learned that Overcooked is an excellent game and there are actually legitimately good team building-type exercises.
This was my first time traveling for work and thought it might be useful to share the tech-related items that I brought with me during the trip. Not just because I’m obsessed with this sort of stuff, but because I’ve learned a bit about what I actually need and more importantly, what I don’t, when traveling.
I kept the majority of my tech items inside my carry-on, which was a Tom Bihn Pilot. It might be the best bag I’ve ever owned and it was roomy enough to hold all my gear while still remaining fairly compact. It has a vertically oriented water bottle/umbrella pocket with a metal grommet at the bottom, which will let water leak out instead of soaking your bag. I also made good use of all the o-rings inside of the Pilot to attach keystraps and various Tom Bihn pouches to organize my kit.
Here’s the full list of gear that I kept in the Pilot:
- MacBook Air (2018): it’s a fantastic machine with a severely flawed keyboard. I still run into issues with duplicate or missed key presses, but hopefully I’ll have a chance to get the keyboard replaced with the latest iteration soon. I love every other aspect of this machine, though, and am glad I chose it instead of one of the Pro models.
- iPad Air 2: It’s over four years old for me, but is still my primary machine for non-work tasks. Writing, browsing the web, watching video, and reading are at their best on the iPad. At least for me. Armed with my essential Shortcuts, I can do just about everything I need to do.
- Nintendo Switch: This is an item that I don’t expect I would bring next time I travel. Two or three of my teammates also brought their Switches and I never ended up taking mine out of its case.
- USB-C Charging Cable: I just use the standard USB-C cable that came with the MacBook Air, nothing special. I do have a fancier Anker cable, but It’s about six inches shorter than the Apple cable. I probably would take the Anker in the future because it’s a bit thinner and easier to wrap up and store. In practice, the length difference wouldn’t have mattered.
- USB-C to Lightning Cable: I have this one from Anker, mostly because I’m a big fan of their other Lightning cables. It’s nice and durable and is great for charging my AirPods or iPhone while I’m working from my Air.
- Magic Mouse 2: I might eventually replace this with a more ergonomical alternative. But until I find one that I like, it’s a nice, portable option that gets the job done.
- Anker PowerPort Atom PD 1: The existence of these ultra-compact, relatively high power output chargers is one of the major reasons why I went with the Air. This charger can power my device without a hiccup and is much smaller and lighter than the default charger.
- Sandisk USB-C Thumb Drive: This serves as my portable Time Machine Backup that I leave in my suitcase while I’m out and about with my laptop. This way, if anything happens to my Air, I can get back up and running quickly after acquiring a replacement.
- Tile Mate: If I ever get separated from my bag, I can use the Tile app to trigger the unit’s audio tone to help me find it or make use of the map feature and rely on other Tile users to track it down. I started using these last year and don’t plan on looking back — every bag I own needs a Tile.
- AirPods 2: The best headphones available. You might notice the omission of “wireless” in that last sentence and I can assure you, it was intentional. The battery life is great, they’re more pocketable than just about anything else on the market, and can switch devices is a snap.
- Lighting Cable: A standard USB-A Lightning cable from Anker that serves as my primary charging cable for iPhone, iPad, and AirPods. It’s sturdy and does the job well.
- Watch Charging Cable: I typically don’t travel with my Apple Watch, but thought I was going to do enough walking during the trip that it would be worth the extra gear in my bag. I ended up appreciating it much more than I initially expected. The ability to receive notifications on my wrist so I can keep in touch with my wife and having a timer that I could use without disturbing those around me were quite handy.
- Anker PowerPort Mini: My go-to bedside charger, which typically powered my iPhone and Apple Watch. Every couple of days I’d use it to top-off my AirPods and iPad while I was working in the hotel or getting ready to head out in the morning. It’s the most compact two-port charger I’ve seen and the primary reason I haven’t dove head-first in to USB-C yet.
I also ended up with a small collection of tech kit in my checked bag. It was all the items that I didn’t expect I’d need or want on my travel days and consisted of the following:
- Tile Mate: Again, there isn’t a bag I own that doesn’t have a Tile inside of it now. Having one in my checked bag was especially neat, I could often launch the Tile app and see that the unit was connected from inside the plane, which confirmed that my bag made it on the flight.
- Lightning Cable: An additional Lightning cable that I could use for charging my devices. I never ended up using this item, so I might leave it at home the next time around.
- Twelve South Compass 2: This is my go-to stand for the iPad, but something I never touched during my travels. I think I’ll keep it in my kit, though, because I did find myself using my MacBook and iPad simultaneously a few times. In hindsight, I should have grabbed the Compass, which would have made these situations a bit more comfortable.
- Lightning to HDMI Dongle: Another item that never left my bag. I brought this in case I had some time to watch YouTube or Hulu before falling asleep, but I never had time. At night, I threw in my AirPods and listened to a podcast while I was getting ready for bed. That was the extent of my hotel room entertainment.
- Apple Watch Woven Nylon Band: I like to switch out bands frequently and wanted to give myself the option to do so during my travels. I would definitely bring one again because I switched twice throughout the week of the meetup.
- Switch Accessories: My portable dock (using this shell), power adapter, and Joy Con Straps never saw the light of day — I just didn’t end up using my Switch at all.
- HDMI Cable: This served as a way to connect my Switch and my iPad or iPhone to the TV through the HDMI to Lightning adapter. I plan to leave this off my packing list next time as well.
As an aside, I used an Away suitcase as my checked bag for the meetup. I bought the medium sized model in asphalt. It’s a joy to use with all sorts of nice little features, but the built-in lock ended up breaking during my travels. The slider mechanism will release the zippers regardless of what combination you enter — that’s not exactly ideal.
I don’t want to give the bag up, though, and wouldn’t mind adding another to our luggage collection for when my wife and I go on trips together. I plan on contacting Away within the next couple of days to see if they can offer a replacement or if there is some trick that I’m unaware of to get it working as expected again.
One last thing to note, Automattic will have me traveling at least a couple of times each year. So if you’re as fascinated by gear as I am, you can expect I’ll be publishing articles like this again the future.