Cassidy Williams

Software Engineer in Chicago

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Traveling to technical events: A guide


I was asked recently by Schuster about my traveling “stack” as a technical person. As someone who used to travel full time for work, and still travels to the occasional conference, I do admit I’ve gotten pretty good at it. So, hopefully this can be helpful for you!

Also to be incredibly clear: this is a “guide” for work-related solo trips. When I pack for a family trip or with my child for any reason, that’s a whole other ball game.

Packing

I pack fairly light. I think people often think they will read more, code more, work out more, write more, etc. on a given trip, but the reality is… you probably won’t. Don’t bring that deck of cards. Bring an e-reader instead of multiple books. Don’t expect too many outfit changes.

I don’t use packing cubes (though I hear they are great), but I do pack things up in little rolls (kind of like the ranger roll) and follow almost the same list for every trip. I wear layers on the plane so I can use a given hoodie across multiple outfits. I never pack extra shoes unless it’s flip flops for a hot place.

My packing list is almost always, for an n day trip:

  • IDs/passports
  • Chargers + their devices (phone, laptop, maybe iPad or Kindle)
  • Headphones
  • Small notebook + pen
  • n shirts
  • n-1 pants/shorts
  • n pairs of socks/underwear
  • Pajamas (if n > 2, 2 sets)
  • Toiletries (toothbrush, makeup bag, toothpaste, comb, deodorant, and if it’s a nicer event, a hair straightener or curler)
  • Hoodie (usually I just wear this on the plane, but if n > 3, bring another)

I think packing light saves your bacon more often than being prepared for every potential scenario!

Specific gear recommendations

I have tried so many backpacks and bags, but this is my latest “stack” of them that I can happily recommend!

  • Eagle Creek 40L duffel - When n <= 3, this bag is perfect for me. It’s spacious enough that I can put all of my clothes in it easily, it can “expand” to a larger size if needed, and it’s light enough that I can carry it through an airport without straining my weak arms. Plus, it’s durable! I’ve been able to put it through a lot over 5+ years and it still honestly looks like-new.
  • Baboon to the Moon canvas tote - If you’re doing a day trip or something that doesn’t involve an airplane, this bag is sturdy and holds a ton. Literally my entire packing list above could fit in this bag if I wanted.
  • Topo Designs Rover Pack Tech - I got this bag as a gift and it’s a fantastic backpack. It is compact by default, but has a lot of compartments and can fit your essentials in it. When I pack this, it has all of my non-clothes items in it, with room to spare if needed. The “tech” version on their website is more expensive than their “classic” and I admit I don’t know enough about the difference to recommend one over the other, but overall I really love the bag.
  • Peak Design Everyday Backpack V1 - In terms of organization, I think this is the best backpack I’ve ever owned. I think it’s best for for day-trips and local trips. I did travel on flights a lot with it and I do like it for that, but the Topo backpack wins for me now purely because of weight. Because Peak Design bags are originally designed for photography, they are very padded, and can be pretty heavy with your stuff in it. That being said… I still love it and don’t mind that, depending on the trip. I think calling it “everyday” is accurate, because it’s good for around town or going to your local meetups (I specifically link to the V1 version of this backpack because it’s the version I own and it’s way cheaper than the newer versions, so you can decide for yourself if you want to go in this direction)!

I was going to link my suitcase I’ve been using here, but it was discontinued, so all I can say is… get one of those plastic or aluminum hard-back ones that you can carry on.

I also use an (also discontinued) mini backpack, often, if I don’t need to carry my laptop with me. I think this is the closest bag to what I use but it’s kind of pricey, so… you decide. For “mini” bags I’ve also seen this sling and this pouch in the wild that seem really nice. You don’t have to use a fancy brand! The fanny pack I use the most is a random one I found at TJMaxx for $10.

I mentioned notebooks and pens before, too! For notebooks I don’t really use anything fancy. I have some off-brand Field Note notebooks (I think the “real deal” are waaay too expensive for a tiny notebook, seriously, just go to your local Target or something and find the “fake” ones), and I use a pen that Ben Hong recommended to me: the Lamy Pico! You don’t need to be fancy here, I just think it’s good to be able to be analog sometimes and be ready to write things down, even when your batteries are dead or your internet is down.

Jet lag

Sleep on the plane for your destination’s time zone, and eat snacks as soon as you wake up. It helps! You will probably be tired no matter what, because events can be a bit draining, but meals and food along your destination’s general schedule helps a bunch.

I admit if my trip is short enough… I just kind of muscle through it, nap on occasion, and I’m often awake way later than I should be. When I was in Berlin a few weeks ago I watched all of season 3 of Bridgerton instead of getting proper rest, because I am a fool. Don’t be a fool.

Booking flights and lodging

Everyone has their preferences for booking their own flights and lodging, so the best advice I can give you here is: sign up for every loyalty point system you can. You might almost always use the same airlines for everything, or have a favorite, but if you’re ever using a flight or hotel that’s not your usual norm, it’s nice to get those points that you can use for later.

Pay attention to how your points can be used, if you aren’t going to be able to take advantage of them as much! For example, I had some Marriott Bonvoy points that were going to expire because I hadn’t stayed in one for a while, but I had juuuust enough that I didn’t want to waste them. I was able to redeem my points in their online shop for some room sprays and gear, instead of losing them!

Scheduling

You will almost always have less time than you think you will. People always want to meet up, last-minute events will come up, and you will just be tired. I went to Figma Config a few weeks ago and I literally had 3 breakfasts one day because there were so many people to meet!

So… prioritize. Book the things that you definitely want to go to, have a “nice to have” list, and otherwise, leave time for rest and ad hoc gatherings! My favorite thing to do when I visit a new place is to have a very high-level plan on the things I really want to see, but then truly just leave the rest to “go with the flow” and act like I live there. It’s cool to get to explore a new place and see where the people take you. Your mileage may vary, of course!

Networking/humans

The best part of events is “the hallway track” (you know how there’s different speaker “tracks” per event? The hallway track is the part of the conference where you meet people in the hallway and talk outside of the official talks)! Taking advantage of the trip and actually meeting people pays such dividends in your career. Get to know people, add them on socials, and follow-up. Email/message the people after the event and just say it was good meeting them. Start building those relationships!

I’m not going to go too deep into this now because I have elsewhere, and I think this podcast in particular that I did a few years ago will help you out, and the book Build Your Dream Network by J. Kelly Hoey is one of the best on the topic, as well!

Have fun

This might be a silly note to end on, but I mean it, technical events are so dang fun. I met my husband at one, I made some of my best friends at them, and almost all of the jobs I’ve ever had could probably be traced back to them. Don’t be too stressed about who you’ll meet. Everyone’s human, and go enjoy the humans, and then sleep a whole lot afterwards (after following up with the folks you met, of course)!

Happy travels!


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