I am a road warrior who has racked up several million miles over the past decade, and since I’m also working more-than-full-time running Automattic (a totally distributed company) and leading WordPress I need the ability to be productive wherever I can find a comfortable place to sit. I carry a backpack with me almost all the time and obsessively tweak and iterate what’s in it, which led to posts in 2014 and 2016. This is the latest edition, and I hope you enjoy it.

1. This is a grey wool buff, which works as a scarf, a hat, or an eye cover if I’m trying to sleep. I tried this out because of one of Tynan’s also-great gear posts.
2. Theraband resistance band, which I aspirationally carry around to help stretch in the morning. Hat tip: Jesse Schwartzman of this blog post fame.
3. Some generic Maui Jim polarized sunglasses with rubber nose pads, which I like for running or hiking because they don’t move around or slip even when you’re hot.
4. Tzukuri “Ford” + charger, a super-cool Audrey company that is like a combination of a Tile and cool sunglasses. They connect via bluetooth to your phone and can notify you when you leave them behind, or use the app to locate them. A charge lasts 30 days. I think this is only available in Australia right now, but should be coming to other countries soon. (Or just buy them on vacation in Australia.) These replaced my fancy Maison Bonnet sunglasses.
5. Westone ES49 custom earplugs, for if I go to concerts or anyplace overly loud. (3rd year)
6. A Tile, which was a gift from my sister. I keep this in a pocket in my backpack and it helps me locate it if I lose it, or if I can’t find my phone I can press the button and it’ll make it beep. Surprisingly handy. Hat tip: Charleen.
7. Hermes business card holder. (3rd year)
8. A cut-out of a chamois cloth, which I use for cleaning smudges and such off glasses and screens. Mine is from Amazon but you can get at any car place or Walmart, use this guide to prepare, and then cut pieces off. Hat tip: Dean.
9. Airpods. These are just fantastic, and I highly recommend them. I use them for calls, podcasts, audiobooks, meditating, Duolingo… they’ve become an essential daily product for me. A cool trick is to use one ear while the other is charging in the “floss” case. Hat tip: Jony.
10. Bose QuietComfort 35, wireless bluetooth headphones. I misplaced my cool WordPress Sennheisers and picked these up in an airport before a long flight. They’re extremely comfortable, great battery life, and I keep an audio splitter and Lightning audio adapter in the case. I’ve hated on Bose many times in the past, but these are decent and I get why people like them, especially the comfort aspect. I am listening to them as I write this. I used Audeze EL-8 Titanium for a while, which obviously sound better, but the lightning cable was unwieldy and it was annoying (and ridiculous) I couldn’t plug them into my laptop. Hat tip: Every airport electronics store.
11. Jabra Sport Pace bluetooth earbuds, which replaced my Powerbeats for running and working out. They have been way sturdier. Pretty inexpensive, too, right now about $60. I know in theory you can run with Airpods, but I’d be too scared of one going down a street drain.
12. Cool carbon fiber money clip, which I use to hold a little cash for places like street vendors that don’t take credit cards, or if I’m in another country and need to carry around currency. The site is a little sketchy, they should upgrade to WooCommerce. Also pictured: The EasyPay XPress NYC Metro Card, which is super handy in New York as it auto-refills. Only downside is it doesn’t work on the PATH trains. Hat tip: Tynan and Rose.
13. Vapur Shades roll-up water bottle. Can hold a full liter, and rolls up to be small like this. Kind of new so I don’t have a strong opinion yet. Hat tip: Lululemon Lab in Vancouver.
14. Fidget spinner, I think this one is from Amazon. Try one of these if you haven’t yet, they’re surprisingly addictive. If you go over to 14 on the left you’ll see a custom metal one a friend made for me. Hat tips: Zach and Xa.
15. Apple Magic Mouse 2. A classic. (3rd year)
16. This is the latest Lululemon Para backpack, and unlike last year’s Cruiser it’s currently available in stores and online. I dig this iteration: it has a little less padding on the shoulders, but the big front zipper pocket is super handy and in general it’s a lot more streamlined and water resistant. Om clued me in to a similar one from Aer, I don’t know who designed it first. Hat tip: Rose.
17. So… there are two laptops, a custom prototype 13″ Automattic-logo Macbook touchbar, and the stickered 15″. I generally only travel with one of these, the 13″ for shorter trips or the 15″ if I’m going to be on the road for more than a few weeks. The performance is just better on the 15″. My favorite things about both are the 4 USB-C ports, that you can charge on any of them, and the Touch ID. (Automatticians after 4 years of tenure can get a custom Macbook, which we now offer with the WordPress, Automattic, or Jetpack logo. I usually get the test ones to make sure the quality is up to snuff.) I carry around the larger 87W brick from the 15″, and keep the extension cable now so it’s easier to plug in on those weak plugs on planes.
18. Kindle Oasis. I still love the Kindle. I’ve started listening to audiobooks this year and the integration with Audible is cool. The Oasis is great because of the real buttons and the fact that you can flip it to hold in either hand, but it’s been the most annoying model in a few generations because the screen brightness isn’t adaptive, and it gives “low battery” warnings when the extra battery cover is low but the actual device is not, which seems to defeat the purpose. Great form factor and ergonomics though.
19. Passport, because you never know when you’ll need to leave the country.
20. A pocket-sized Baron Fig notebook, which I use in meetings to avoid my phone. Hat tip: Rose.
21. Google Pixel. Best Android phone I’ve used, uses USB-C which I love, I love the size. I use this mostly for testing and staying current on Android, or as a backup. I use Google Fi for service on this one.
22. Forerunner 735, charger, and heart rate strap. I actually switched to the 935 since this picture was taken, but my notes apply to both. (Here’s a great review of the new 935.) Garmin makes the best fitness smartwatches in the world right now. Aspects are clunky: the app is not the most elegant, the add-on watch faces and such leave something to be desired, the sleep tracking is way worse than Fitbit, and there is no fine-grained control over notifications. That said, the battery life goes 8-10 days (!) so I often don’t even bring the charger when I travel. The stats are unparalleled especially for running. It’s waterproof and can also track swimming and biking. Finally my favorite feature: the screen is always on. I know that sounds basic, but I have been driven crazy by years of Fitbit and Apple Watch require tapping or wrist gesticulations just to see the time. (Extra awkward in a meeting.) My hardcore fitness friends love this one too. Hat tip: Aaron.
23. Three little fun personal care items: a great chapstick from Japan I don’t know what it’s called, but it says retaW aoyama / tokyo fragrance lipcream on it, Aveda Peppymint breath refresher, and an Aesop Ginger Flight Therapy roller similar to the Blue Oil one from last year. Hat tip Esther, Naoko, and my mom.
24. Belkin car mount, really handy when renting a car and navigating around. (3rd year)
25. This is a more-expensive but not-better version of what I had last year, which I’ll quote and actually recommend: “This is probably the least-travel-friendly thing I travel with, but the utility is so great I put up with it. It’s the Sennheiser Culture Series Wideband Headset, which I use for podcasts, Skype, Facetime, Zoom, and Google Hangout calls with external folks and teams inside of Automattic. Light, comfortable, great sound quality, and great at blocking out background noise so you don’t annoy other people on the call. Worth the hassle.” I leave the USB-C adapter attached to this. Cable still annoys me.
26. iPhone 7 Plus, on Verizon, with a Bellroy 3-card case. If you’re a guy I highly recommend trying out a phone wallet case, it’s a game-changer to only have one thing to keep track of and not having a wallet in your back pocket is good to avoid getting misaligned. I have three cards in it, an Amex, a Visa, and my drivers license. In NYC I also squeeze in the Metrocard. Hat tip: Craig (a previous Bellroy model).
27. The Japanese company Maruman makes this awesome grid-paper lie-flat notebook, which I fill and occasionally draw in. I love this thing, and having a work area where I can have my laptop, mouse, iPad, and this notebook all set up next to each other is my happy place. The paper is soft. Hat tip: Brian.
28. 9.7″ iPad Pro + smart keyboard cover on AT&T. I didn’t expect to, but I really love this device. It gives me way more joy than my phone or my laptops. Gorgeous screen, long battery life, always connect, I can tether to it, write on it with the pen in 32, the keyboard is fast and silent, split screen is handy… I don’t know how to describe it. Like the Airpods, this product just excels in every area. I still have and need to use a laptop, but it’s less of my day and mostly because of some internal tools and security stuff we have.
29. I ended up with this beast Cable Matters USB-c mega-dongle to cover ethernet, VGA, HDMI, and old USB. Warning! To use the ethernet on MacOS you need weird drivers. Hat tip: Amy.
30. I’m not sure why I started using this Plantronics Voyager bluetooth headset, but it’s really good. This might not make the cut next year as the Airpods are pretty good, but if I’m going to be on a regular (non-Facetime) phone or conference call for a few hours, this is what I turn to. Hat tip: An Uber driver.
31. Lockpick set. (3rd year)
32. An awesome Hobonichi Techo pen (they have cool notebooks too), a sharpie (for signing fans’ items), and Apple Pencil for the iPad Pro.
33. Two rings: one Margiela one which has my lucky number 11 circled (for a long reason related to their numbering system), and one with the WordPress logo that was also a swag prototype for a ten-year tenure gift. I might wear these to remind me of something I’m trying to remember or focus on during a day.
34. I’m digging this Imazing 10k charger: it’s a cool color, smaller and lighter than last year’s, has a USB-C port, and outputs well. I found I never needed the 20k capacity of last year’s, hence the downsize to 10k.
35. This Aukey 30W / 6A travel wall charger I wish was all USB-C ports. I sometimes trickle-charge the laptop off this overnight.
36. A really mediocre Native Union two-port USB I got from TED. Not going to link since it’s not very good because of the way it plugs in. Since the photo I replaced it with the much-more-useful Aukey 2-port, which I highly recommend and give away all the time.
37. A pretty handy Ventev dashport car port charger that’s small and light. I found myself rarely using the USB-C on last year’s so I opted for smaller size and less weight in this one.
38. Mintia mints from Japan, yum. (I buy these there or ask friends to bring them back, they are much cheaper there than the cost on Amazon.)
39. This rat’s nest of cables and adapters is embarrassing, and I will further apologize and rant in the epilogue.
40. A random used mystery book I picked up at the Paper Hound Bookshop in Vancouver.

What blows me away making this list is that since last year almost every single item has changed, unusually high churn. I see now why y’all were tweeting me to update this post.

Two bonus items: Even in the summer I’ll often have something like this light Lululemon running jacket stuffed in a pocket for over air conditioned places or at the end of a flight when it gets chilly. I’m also currently testing out the assisted meditation device The Muse, but it hasn’t really stuck yet and I usually just turn to Calm.

Ensuring network continuity: One thing you’ll notice is the iPhone is on Verizon, which has the best network in the US, the iPad is on AT&T, and the Pixel is on Google Fi. This allows me to have a diversity of network access which is occasionally handy in the US and has saved my butt a few times when overseas. Whichever device has the best connection I’ll just tether the others to it. I almost never join coffee shop or hotel wifi these days, a good LTE connection is usually better.

USB-C Is Why We Can’t Have Nice Things

Oh, USB-C, I love you. You’re reversible, fast, and work for everything, like I can charge my laptop with almost anything, and many new devices like Google Wifi use you for power. The dangerous cable on Amazon thing seems to have worked itself out, and having 4 ports on the laptop is amazing, I can charge everything I need off it. But as you can see from the mess of cables and how many other legacy USB things I’m carrying around, we’re (still!) in this really awkward in-between phase for computing. First, there are no good retractable cables, especially ones that have USB-C on one end and Lightning or Micro-USB on the other. I wish my headset, headphones, sunglasses, and Kindle didn’t need Micro-USB, and I wish the Airpods, iPhone, iPad Pro, Magic Mouse would just give up on Lightning and support USB-C instead. But we’re in this liminal space, and the number one thing I hope is better by next year’s post is that the USB-C accessory world has flourished and I just have a couple of neat retractable USB-C cables and things like the battery, wall charger, and car charger in 34, 35, and 37 just have all USB-C ports. A boy can dream, right?

In Closing

Partly because the backpack is a little smaller, I’ve really tried to streamline and a lot of things from last year, like a small digital camera, the Chromecasts, travel router, etc I don’t bother carrying around in my backpack anymore. I hope these can get simpler and shorter every year. I tagged these with an affiliate ID for Amazon this year but mostly just to see if anyone actually buys stuff from these posts. I walk millions of steps a year with my backpack and wouldn’t carry something around unless I really believed in it, which is also why I’m always testing and trying new things. As you can tell a lot of this kit has evolved from recommendations, so if you have any please leave a note in the comments. I’ve also considered doing something similar for shoes, clothes, apps, suitcases, or toiletries, so holler if you’d like any of those. Alrighty, that’s it until next year!