My travel habits

16 minute read

For the past several years I’ve traveled a lot for work and professional reasons. Being away from home so much can be a drain and is really hard on your body and mind. Over the years I’ve developed some habits that have made my travel life, while not easy, at least less unpleasant. As I complete my final trip for the year it seemed a good time to share some of those habits. The primary goal of all my travel habits is to reduce my stress while on the road. Maybe some of them might do the same for you.

As my friend Chris says, “All travel advice is wrong,” so don’t take what follows as advice so much as a running list of things that work for me. They may not work for you. You may even find some of them silly. That’s OK. You do you, honey. Also note that these are my habits and therefore are not up for debate. You may not agree with them. You may think roller bags are great or that there’s nothing wrong with checking luggage all the time. That’s fine. I encourage you to write a blog post about your habits rather than telling me how mine don’t work for you.

I’ve categorised them into different stages of my travel process:


  • Book the hotel the moment you think you may go somewhere. Nearly every hotel allows for free cancelations within a week to a few days of a reservation. Take advantage of this and book early, even if you don’t yet know for sure whether you’ll be making the trip. Just make sure to set a todo item to verify/cancel the booking in time before you get charged.
  • Book multiple hotels. Is there the chance you’ll be price sensitive at the time of the trip? Book multiple hotels then keep only the cheapest one when the trip rolls around.
  • Use TRIPBAM (or similar). TRIPBAM (yeah, they capitalise it like that) is a service that’ll look for cheaper rates on hotels you have booked. It’ll even re-book for you at a lower rate if you want. Sometimes this can save you a lot of money.
  • Have a single source of truth for travel plans. Having various bits of travel plans scattered across several emails is not helpful. Find a and use a single source of truth where all your plans are stored. Calendar, Tripit, whatever. I don’t care what you use, just make sure it works offline so you can check things when your devices are off the net.
  • Sad to say, but status matters. When you stumble into a hotel at omg-early and your room is already available, you’ll be grateful you focused your stays on a single brand and earned status. When you get that last upgrade on a transcontinental flight, you’ll be glad you concentrated your miles on one airline. It really does make a difference.
  • Sign up for status programs even for a single stay/flight. If you have to book on a brand that isn’t your usual one, sign up for the status program anyway. It can get you insta-perks (like free or faster wifi at hotels). Plus you never know when you’ll need it again and those points can add up over the years (if they don’t expire; many don’t).


  • The answer to “should I pack this?” is always “NO”. Don’t what-if your way to a bag that’s twice as large and heavy as needed. Most people are traveling to civilised places. If you find you actually do need that thing at your destination, just buy it there. (yes, there’s a lot of privilege in that statement, I acknowledge that)
  • There is nothing wrong with rewearing clothes. Five day trip? Pack 2 shirts. That plus the one you wear on the plane will be plenty. Have a spill and ruin a shirt? Towns have shops. Buy a new shirt if you need, or if you’re going to a conference it’s safe to assume you’ll get a t-shirt from that and/or from a vendor on the expo floor.
  • Laundry facilities are a thing. A lot of hotels will have coin-op laundry facilities somewhere on site. If not, there may be a laundromat nearby. A last resort is using the hotel laundry service, but those usually are really expensive.
  • Always check the weather. Wait until just before you pack, then check the weather. Rain, snow, sun…these things happen suddenly, so it’s not worth it to check too far in advance.
  • Always pack an umbrella. No matter what the weather says, always pack an umbrella. Get one you can always keep in your luggage (and make sure it stays there rather than sneaking off). You will never regret this but often will regret not having it.
  • Travel backpack is far superior to a rollerbag. When I’m navigating a strange city or a crowded airport, I want my hands free and I want maximum mobility. I’ve tried the Tortuga recommended by Wirecutter and didn’t like it. My current long-haul bag is an Osprey Farpoint 55 and I love it for any trip longer than five days. For trips shorter than that I use an Ogio that I received from my friends at
  • Consider 1-bagging it. I strongly dislike checking luggage. It gets lost. It slows me down. Instead, I do everything possible to travel with a single bag that I can put overhead. Yes, I can do this with my Osprey.
  • Pack a separate small bag for onsite. Wait, didn’t I just say to 1-bag it? Yes, but you can pack a bag inside another bag…or your bag can include one already. My Osprey has a daypack that I use during conferences and meetings. I also put all my electronics in it, so if I do have to check the big part of the bag I can keep my gear with me. When I use my Ogio, I slide a BetaBrand Under The Jack Pack in there along with my laptop. Using a minimal bag while out and about means I’m less likely to carry too much and get exhausted.
  • Always pack a small shopping bag. A friend gave me a small cloth bag from a cute used bookstore. It stays in my luggage and has been endlessly useful for holding groceries, souvenirs, and once even as an extra carry on when I accidentally gained too much stuff during my trip.
  • Roll the clothes. Most of my clothes are knit (think t-shirt fabric), so they don’t wrinkle much. I roll them as tightly as possible so each one takes up very little room. Yes, underwear as well. I didn’t think that one would make a big difference but it does.
  • Use packing cubes. I didn’t used to like these, but since I got my Osprey I’m a big fan. I use the smallest Amazon Basics cubes, which have the perfect footprint for the Osprey. Load ’em up, stack ’em up in the bag, zip it up, you’re done. Before this I had things all jumbled up in the Osprey and it got complicated. Now it’s nice and tidy and I can find everything easily.
  • Set out travel clothes while packing. Not only does this let me plan my outfits, it also ensures that the morning of my flight (which inevitably is earlier than I’d like) goes smoothly and quickly. I always regret when I don’t do this.
  • Denormalise some gear. It’s OK to have multiple copies of stuff. For instance, each one of my bags contains a computer power supply so I don’t forget to move it from one bag to another. I also travel with multiple pairs of headphones (wired and bluetooth, each with microphones), because that piece of gear is so important to my mental health while traveling that I can’t risk being without.
  • Consolidate with a multi-plug power supply. I think I’ve purchased about eight of these Anker USB-C/USB-A power supplies (they’re scattered around my house) and I’ll gladly buy eight more. When traveling, with a single plug I can recharge my MacBook, both my iPhones (one for work), my Apple Watch, and my iPad. It’s so good, especially when overseas (more on that in a bit).
  • Retractable cables are great. While I’m a huge fan of using velcro cable ties on every cable and cord I own, when traveling I prefer to use retractable cables as much as possible. I found these multi-plug retractables and they make it a lot easier to find things in my little cable bag. They’re also good in my everyday carry (aka EDC). I can grab one, toss it in a pocket, and take off.
  • Collapsible drinking vessels are great.: I’m not a fan of single-use items, so I try not to use disposable coffee cups or drink bottled water. Instead, I carry (and love) a Stojo collapsible coffee cup and a Hydaway water bottle. These things kick ass and I now can’t imagine traveling without them.
  • Consider a (collapsible!) kettle.If you like tea (and I do) and you travel a lot (and I do), you’re going to be disappointed by most hotel rooms (and I am). Unless you’re in the UK/EU, your room is unlikely to have a kettle. The coffee makers most rooms provide are usually pretty bad. Pack your own coffee/tea and a collapsible kettle and you’re all set.
  • Kitchen towel as a jewelry roll. For years I couldn’t figure out how to travel without tangling necklaces or risking losing earrings. Now I use a simple kitchen towel from IKEA as a jewelry roll and love it. A few basic folds to hold things in place, then roll it up. Everything’s safe and padded and, when in a packing cube, there’s no risk of anything getting lost in transit.
  • A dryer sheet can keep things fresh.Packing a dryer sheet in your luggage not only keeps things nice and fresh in there, it also smells a lot more like home. That can be comforting when you’re going into your umpteenth day on the road. Leave the sheet in your luggage when you’re not using it and things will also be nice and fresh when you get back to that bag for your next trip.
  • It’s OK to have a travel buddy. This one took me a while to figure out. I miss my cats terribly while I’m on the road. To help with that, I’ve started packing a small Toothless. Sure, he’s a dragon and not a cat, but he reminds me of my Nigel, so now he’s my Nigel proxy. It’s nice to have a friendly face of some sort in my hotel room when I return after a long day.


  • Always have buffer time. Due to circumstances beyond my control, I missed my flight on my very first solo plane trip, years and years ago. That was so traumatic that now I’ll very happily get to an airport two more more hours before even a domestic flight. These days I also do it so I can work my airport transit time around my various calls and meetings. I can take those just as easily from the airport, and right up until boarding.
  • Get lounge access. I have both Delta Sky Club Executive (which I buy with miles) and Priority Pass Prestige. Between the two of them, there’s a lounge I can use in nearly every airport I travel to. Contrary to popular belief, most lounges aren’t swanky. They are, however, safe and relatively comfortable places to recharge your devices, take calls, and grab a bite and a coffee. They’re also great because you can leave your stuff at your seat while you go pee without someone calling TSA about “abandoned and suspicious” bags. As someone who almost exclusively travels solo (so there’s no one else to watch my stuff), this is worth its weight in gold.
  • Some airports to avoid… MCO (Orlando) is full of families, each with a pack of kids, and few of whom have ever flown before. It’s hell on earth for a seasoned traveler. CDG (Paris) is crowded, disorganised, ugly, and people aren’t very helpful (in my experience). LAX (Los Angeles) is chaos writ large, especially if you fly Delta since their terminals are currently under construction. I don’t find LAX to be the hellscape others do, but it could be more pleasant.
  • Some airports that rock… PDX (Portland) is my home airport but it would be a joy even without that. SEA (Seattle) is well organised and well appointed. Same for MSP (Minneapolis/St Paul) and SLC (Salt Lake City). Yes, these are Delta hubs and Delta is my airline of choice, but they’re also really nice so I don’t mind connecting through them and having to spend an hour or two in their lounges (which are also usually very nice).


  • Buy/use a local coin purse for local currency and metro cards. I have one that says “Brussels” all over it for my Euros, a Swiss flag one for my Swiss Francs, a Union Jack one for my pounds, one that says “Australia” for my Aussie dollars. When I get home, I just place them in the dresser. When I need to travel to that region again next, there’s no question which one to get. I make sure the coin purse is large enough to hold metro cards then keep those in there as well. The purse also makes life so much easier when I reach my destination, since all the currency stays wrangled rather than in a pile on my hotel dresser at night.
  • Buy international figure 8 cables. I thank my friend Ricardo for this one. The Anker power supply (see above) uses a standard figure 8 plug for the power cord that runs from it to the wall. Rather than carrying a plug adapter (OK, I carry one of those too just in case), just buy the figure 8 cable for the region where you’re going. I have them for EU, UK, AU/NZ, US. This tip alone has saved me so much fuss and clutter and I’m deeply grateful for it.
  • Use T-Mobile. (This one’s for US folks) Not only do I get free wifi for my phone on domestic flights, they also have excellent global roaming plans. They even have a $50 international pass that gets me up to 15GB of data at the same speeds I’d have in the US. I can even tether from it! This has saved my butt more than once when hotel wifi wasn’t enough to handle an online call (Zoom, Skype, or what have you).

On Plane

  • Hoodies are the best. Layers if the plane is too cold. Hood if there’s too much draft or if I want an eye shade. The hood is also great to discourage chatty neighbours. The pockets hold my phone, snacks, batteries, cables rather than lose them in a seat back pocket. I won’t fly without a hoodie.
  • Laptops stow well/quickly/securely behind your back. In a bulkhead seat where there’s no decent pocket in front? Just need to move quickly so the attendant can place the meal down on the table? Close the laptop and slide it between your back and the seat. It’s secure and out of the way.
  • Stay hydrated. This one’s easier because I only sit in aisle seats, of course. Staying hydrated keeps my ankles from swelling up and keeps my energy level from flagging too much. This is a lot easier thanks to my Hydaway bottle (see above).
  • Soften butter under warm entree. That pat of butter that comes with the roll will be a tiny block of ice. The entree is not. I put the butter under the entree while eating the salad and it’s soft by the time I get to the roll.
  • Save crackers/cheese from the meal for later. Many entrees come with a pack of crackers and a piece of cheese. I don’t sleep during flights and on long hauls can get peckish in the middle. I save that cheese/cracker (often in my hoodie pocket) for later to keep me going.
  • Take extra packs of nuts/peanuts for later. Relatedly, if a flight offers packs of nuts I’ll take two or three each time then stash them away for later…where “later” usually means “at the conference, since I’m usually so busy that I miss lunch.”

At the hotel

  • Take pictures of everything. No, I don’t mean in a touristy way (though that’s good, too). When I’m in several hotel rooms over a period of a few weeks, I will mix up room numbers. At each hotel, I snap a pic of the key envelope on my way to your room. Also I take pics of rental car plates, parking spaces, wifi passwords, or anything else that there’s even the slightest chance I might forget.
  • Always keep stuff in the same general areas in every hotel room. Contacts to the left of the sink. Wallets, keys, sunnies by the TV. Charging station on the desk. Not only do I never lose anything, I also have only a small number of places to check so I can pack more efficiently (and without forgetting anything). One of those places is the closet…
  • Hang clothes to air after wearing. If I’m going to wear clothes more than once I need them to air out and not be in a heap on the floor. This also keeps my room tidy, which is nice, but I mostly do it to air things out and to remind myself what I’ve worn already. I also always hang up my hoodie or jacket when I get in so all of the stuff is contained in a single place that needs to be checked when packing. The last time I forgot to do this I had to have a Gore-Tex jacket Fed-Ex’d to me from Boston. Live and learn.
  • Find a local grocer near the hotel. Hotel breakfasts rarely agree with me, plus I’m often working in my room in the evenings. A shopping run to a local grocery store or bodega ensures decent breakfasts as well as snacks and fizzy water for when I’m working.
  • Use melatonin. I’m pretty cautious about sleep aids, but when jet lag is bad enough I’ll slam it down with a couple melatonin tablets. It doesn’t always work for me, but it works often enough to keep trying.
  • Get a red light. Is the bathroom on the left or the right side in this hotel? Where exactly is that table leg, anyway? I don’t want to screw up my sleep more in the middle of the night by turning on lights, so I pack a battery-powered red motion-sensing light. The red light won’t fry my night vision, which is nice. Just before bed I turn it on auto mode and set it on the floor where it’ll be activated when I stand up from bed. This thing has improved my nights much more than expected, especially as I hop from hotel to hotel in a short period of time.
  • Always have comfy clothes for the hotel. Being able to slip into leggings, a baggy hoodie, and goofy handmade slippers really helps my stress level when on the road. This is especially true because I spend so much of my time working in my hotel room. I could easily gain back a lot of luggage space by leaving these out (that baggy hoodie isn’t small), but it’s worth it to me to have “house clothes” while in my room. Those slippers are particularly good for my mental health for some reason.
  • There’s no reason your essentials can’t be fun. I have a foldable comb/brush. It looks like a T-Rex skull. I have a toothbrush with a travel cap over the bristles. It looks like Iron Man and the helmet is the bristle cap. Just because I’m an adult doesn’t mean my stuff can’t still be fun, especially when I’m far from home and need more levity than normal.

So there it is. My big list of my Elaborate Coping Mechanisms for when I’m on the road. Maybe something in there will be helpful for you, but even if not it was fun for me to collect them all in one place like this.

Bon voyage and Vaya con dios.