This article is the culmination of twenty years of traveling for business and pleasure. In the past ten years, when I started traveling a lot, I really began putting thought into how I traveled.
Above all else, I optimize for three specific things: comfort, convenience, and consistency.
This is particularly true for business travel. When traveling on vacation, I generally give up on one or more of these in exchange for an improved overall experience (for example, staying in an off-the-grid hacienda in remote Costa Rica is none of these, but it’s a fantastic experience).
I will say upfront that the reason my approach to travel works is because I own my own business, and have full discretion in how the business money gets spent. For those traveling regularly but having to work under corporate travel guidelines, your mileage may vary.
My daily bag
I carry an ten year old Fossil messenger bag with me every single day, including when traveling. The contents of the bag are the same no matter if I’m walking to my local cafe or going to a different city. I’m including this here, despite it not being travel related, as it helps explain the contents of my travel bags.
This bag contains everything I need on a daily basis. I’ve designed the contents such it always lives in the bag and isn’t used in hotel rooms (I have separate cables for the hotel room; see below).
- Apple AirPod Pro 2.0
- Sony DREX61IP earbuds
- Apple USB C to 3.5mm adapter
- Apple Lightning to 3.5mm adapter
- Anker PowerCore Slim 10000 PD
- Anker 643 USB C to USB C cable, 3′ length (color: white)
- Anker 641 USB C to Lightning cable, 3′ length (color: blue, so it’s easy to distinguish from the USB C-USB C cable)
- Apple Watch USB C charging cable, 1′ length
- USB A to USB C adapter (small)
- Apple USB A to USB C adapter
- Purgo USB C hub
- Anker 543 65W II
- Apple USB C to USB C cable, 6′ length
- Pen, mechanical pencil, sharpie
- Tide pen
- Fieldnotes memo book
On international trips, I’ll also include the power cable for that country in the bag. I dislike using travel power adapters and prefer to use direct connections. Apple sells an international travel kit, which I used to use before I swapped my Apple power brick for the Anker 543.
I noticed the Anker 543 uses a C7/C8 connector on the brick side and the ones they sell on the UK and EU sites looked identical, so I simply bought a C7/C8 UK and EU cable. This allows me to just swap the power cable and keep everything else the same.
I never check bags. Baggage claim consumes too much time and the potential for a lost bags introduce inconsistency, inconvenience, and a lack of comfort to the trip.
Some people seem a little in awe of my ability to one-bag it, but it’s really not that hard (to me, at least).
I have two bags I use for travel, depending on the length of the trip. Both are by Minaal, a company formed by two long-term digital nomads to create a better travel bag. I’ve been a customer since the first release. The two bags are the Minaal Daily and Minaal Carry-On (Link is to the v3.0, but I use the v1.0 – They’re on v3.0 now but it’s not compelling enough for me personally to upgrade).
I use the Daily bag for trips of 4 days or less and Carry-On for trips of five days or more. Traveling for three months is the same as travel for seven days for me, luggage-wise. A guiding principle behind the contents of my packing is that anywhere I’m going, people live their daily lives. Which means if I’m missing something, I can buy it locally. As such, I never worry about trying to pack for every contingency.
In fact, I never pack clothes for more than seven nights. If my trip is longer than that, I expect to do laundry at the hotel: every mid-tier and up hotel has laundry service, though it can be expensive.
Each of my two bags contains the same stuff, aside from the clothes. In other words, I duplicated the baseline contents so that both bags are always ready to go; I just add clothes and it’s done. Packaging either bag takes me no more than 15 minutes.
Each bag contains a toiletry bag (see below), cable board (see below), a Lewis ‘n Clark cable lock (this cable lock perfectly fits the holes on the MInaal bags), 2x generic carabiners, a Logitech C920 HD webcam, and a Blaux portable bidet (a clean bum is always nice).
One thing I haven’t duplicated between the bags is my Bose QC45 headphones, simply due to cost. I wear these exclusively on the plane for their noise canceling capabilities–removing the turbine noise makes the trip much more bearable.
Protip: If you need to stash your bag somewhere and you aren’t checked into your hotel, your hotel will hold your bag for you at no cost. That applies whether you’re checking in later in the day or just checked out. Bonus points: this is true of most medium tier and higher hotels, regardless of whether you’re staying there or not. I simply say, “Hey, I’m just quickly passing through the city. I’m an elite member here and just need to stash my bag for a few hours. Can I leave it with you?” Never had someone turn me away yet.
The toiletry bag is contained in an eBags CTS Mini Square Packing Cube.
- 1x roll of Tums
- 3x travel toothpaste containers
- Electric toothbrush + charging base
- Glide flosspicks
- Razor and 2x blade packs (I’m bald, so I go through blades quicker than most guys)
I never pack shampoo or soap, as every hotel I stay in has them.
The cable board is contained on a JOTO cable organizer.
- 2x Anker 333 USB C to USB C, length: 3.3′
- 1x Anker 321 USB C to Lightning, length: 6′
- 1x Apple Watch USB C charging cable, 1′ length
- 1x Apple USB A to USB C adapter
- 2x Anker 726
- I swap these for 2x Anker PowerPort III 2-port 60W on international trips. I can’t find them on Anker’s US website, so you’ll have to buy from Amazon. What I like is that they contain swappable plugs for different countries. I don’t carry them inside the US because they’re so much bulkier than the Anker 726.
Many of my colleagues prefer rollerboard bags. I own several, so I’m no stranger to them, but I personally find a backpack to be much easier to move around in. It’s less professional looking but the movability makes up for that in my mind.
I use an eBags CTS medium compression bag and eBags large compression bag packaging cubes for my clothes. If I’m traveling with my larger Minaal Carry-On bag, my socks, underwear, and undershirts go into the large compression bag and dress shirts and pants into the medum compression bag. If I’m traveling with my Minaal Daily bag, I only use the medium-size compression bag.
I always unpack dress shirts when I arrive at the hotel, so they’re easily at-hand.
Flying sucks. Even if you ignored the TSA and their security theatre, the cramped airplanes, and the shitty food, it’s still a poor experience overall. The best I think we can do is attempt to make it more bearable, even knowing we’ll never get to a point where it’s actually enjoyable. Oh well.
I generally fly business class, and I often pay for it as a full-fare ticket. In other words, I don’t buy coach class and hope for an upgrade. While I’m United 1K and can get upgraded the soonest of all other tiers, it’s not consistent enough for my taste.
Speaking of United, they’re my airline of choice–not because they’re amazing or anything, but just because I live near one of their major hubs (SFO). I only recently hit 1K for the first time (after years of requalifying at Platinum), but did so on PQPs instead of flights–mostly thanks to buying full-fare tickets.
I pay for lounge access for United Club and receive free access to the American Express Centurion lounge with my AmEx Platinum card, as well as access to Priority Pass lounges thanks to other credit cards I have. I’ve never found the Priority Pass lounges to be worthwhile, so I mostly ignore it.
I like the AmEx and United lounges, though some are better than others. They’re a great place to hang out on a layover away from the hustle and bustle of the rest of the airport. Some are almost peaceful, even.
One of my favorite lounge perks is arrival lounges on transatlantic flights. For example, the arrivals lounge at Heathrow is extremely welcome simply because of their showers! The food and lounge itself aren’t anything terribly interesting, but being able to shower and freshen up after a 6+ hour overnight flight is pretty great.
Airport expediting things
TSA’s security theatre is just hilariously bad and I do what I can to minimize my exposure to their tiny emperors.
One of the first things business travelers learn is to pay for PreCheck and Global Entry. However, one thing that isn’t so obvious is that paying for the NEXUS pass (NEXUS is like Global Entry, but for entering Canada) includes PreCheck, Global Entry, SENTRI (Global Entry, but for Mexico), and NEXUS for the same cost as Global Entry. Only downside is that you have to do your interview in-person at a handful of Canadian airports, but hey, there’s an excuse to get in some time in Canada! Link to the Trusted Travel Program, which all of these are governed under.
I also pay for Clear, which expedites security at major airports. With my combined Clear and PreCheck, I haven’t spent more than five minutes in a security line in years.
While my home airport is PDX, my primary hub is SFO. This means i’m often flying to SFO to start trips. For example, if I’m flying to EWR, I’ll fly to SFO the night before so I can catch the SFO-EWR direct flight instead of connecting through ORD or DEN if I were to leave from PDX directly.
It’s much easier to live in a hub city. If I lived in a small city again (eg, TYS), I suspect I’d be flying to a hub city the night before every trip just so I had better options on flight times. Living in a small city sucks for flights. Even PDX is annoying sometimes (for example, there’s no United route from PDX to SEA, so I either have to take Delta or route through SFO).
I always fly out of the closest airport to me. When I was young, I would sometimes drive from TYS to BNA (2.5 hours) to save a couple hundred bucks. I don’t do that anymore–the inconvenience is just too much and the opportunity cost too high.
I pay attention to specific aircraft models. I prefer an Airbus A380 or Boeing 787 when doing transatlantic flights (but, alas, these are being phased out), a Boeing 777 or Airbus A320 when doing transcontinental, and an Airbus A319 or Boeing 737 on everything else. United has some other Boeing models, as well as Embraer for small airports.
I avoid Embraer as much as possible. Sadly, the Embraer CRJ200 (or as one friend put it: The Devil’s Chariot) is the favored aircraft of United when flying into/out of small airports, such as my hometown (TYS).
Much like flying, I picked one chain and stay with it. My chain of choice was previously Starwood, and thus became Marriott after the merger. I still have mixed feelings about that merger, but it’s worked out fine.
An upside to Marriott is that they have hotels basically everywhere. A downside is that none of their hotels are particularly amazing. They all offer a pretty consistent experience. I’ve maintained Platinum status with Marriott multiple years running now, but I have found myself staying in Hyatt hotels more often while traveling personally, as Hyatt has more unique, higher-end hotels. For example, I spent Christmas 2022 in New York City, where I split my trip across the Park Hyatt and St Regis–the top-tier of each chain in NYC. Despite the Park Hyatt being $200/night cheaper the the St Regis, the St Regis was an incredibly underwhelming experience.
I prefer to stay in city centers when I travel. Occasionally, a client’s office will be nowhere near the city center, though. In those cases, I opt to stay close to the client. If I’m going to a city for a client, I’ll usually stay longer than just the time for the client so I can do a meetup or meet with other clients. When that’s the case, I relocate to a city center hotel after I’m done with the client. I generally go for category ~5 hotels (W, Westin, JW Marriott, a few others) because they’re consistently solid quality and cater mainly to business travelers. My EA maintains a list of hotels I prefer in each city I go to, so that I’m always staying at the same hotel. Like I said, I love consistency.
People often ask me why I don’t stay in Airbnbs, particularly since I once worked there. The issue comes down to a lack of consistency and a lack of convenience. If I’m arriving late due to unexpected travel, I’m screwed in many places. It’s hard to even tell ahead of time if the host is providing soap! That said, I will sometimes opt for an Airbnb when traveling personally, particularly if I can get a better experience, such as a lakeside/beachside house, or if I want to stay in a neighborhood devoid of hotels.
Where possible, I try to travel by train instead of car or airplane. I find trains to be so much more comfortable and convenient (particularly in western Europe). Northeastern US train travel is fine. It’s noisy and slow compared to European trains, but I still prefer it to airplanes.
I usually opt for business or first class on these, as the ticket prices aren’t that much more and you get quieter cars and more comfortable seats. Some trains don’t really provide anything for the upgrade, though–I try to pay attention when that’s the case and save the money with a coach class ticket.
When traveling locally (that is, within a given city), I prefer the subway or rideshare services, depending on the needs for the trip. It’s hard to explain how I make these decisions on a per-trip basis as there are so many variables, so I’ll just use that as a cop-out to not. 😅
When I use ridesharing services, my go-to is Lyft, though I have Uber installed for cities where Lyft isn’t widely present. I generally go for whatever the cheapest option is when going solo, unless I’m going more than 30 minutes, in which case I upgrade to Lyft Lux/Uber VIP. If I’m traveling with more than two people, I’ll often upgrade to a Lyft Lux SUV/Uber VIP SUV. If perception is important, such as traveling with a client, I’ll opt for Lyft Lux/Lux SUV/Uber VIP/Uber VIP SUV no matter the other criteria.
I very rarely rent a vehicle. When I do, I usually go for something from Turo (a carshare service) instead of the major car rental companies for one main reason: as a car guy, I very much care about the exact car I I’m getting and Turo gives me more control over that. When I do rent a car, it’s almost always when on personal travel, as my business travel rarely puts me in a position of needing it.
One of my big indulgences with local transport is when I’m in New York City: I take a helicopter when going between Newark and the city. It sounds wildly excessive, but the math actually makes sense: it’s $180-$200 per person on Blade NYC with a travel time of seven minutes between the two points, and the helicopter often takes off when you arrive. Contrast that with half an hour on a train to/from NY Penn Station (price: $30) or the 1h-2h in a car (price: $100+). Only major downside is that Blade NYC terminates in Hudson Yards, which is a dead zone for the subway, so there’s often a quick taxi/Lyft ride from there to elsewhere in Manhattan. Because of that, I tend to use the train when going to Manhattan from EWR, and use Blade when going to EWR from Manhattan.
Working in non-home city
Being able to get in some real work is important while traveling. I have a few tricks for that.
Because I travel to San Francisco so often, I have a coworking membership at SHACK15 in the Ferry Building for $1500/yr. They also have rentable rooms with TVs, which makes it easy to do private team or client meetings there.
In other cities, I either work from the hotel’s restaurant/lounge or a good coffee shop. I try to scout coffee shops ahead of the trip, since I’m rather picky about them.
Connectivity-wise, I rely extensively on hotel wifi, the cellular connection on my iPad, and tethering via my phone. For international trips, I have the International Day Pass included on my AT&T cellular plan, which kicks on for $5/day when it detects I’m not in the United States.
Credit cards & The Points Game
Back in 2012, I learned there was this whole credit card points game. I always wondered how people got free flights and that’s how I learned that most points are earned on the ground, not in the air.
I played that game hard, peaking at some 22 unique credit cards. I would acquire a credit card just for the sign-on bonus.
When I started Duckbill, I stopped playing. It wasn’t really a conscious decision, but one borne more of practicalities: if I used my company credit card, I didn’t have to fill out expense reports.
Now, I’m down to only a handful of cards: Chase United Explorer, Chase Sapphire, American Express Marriott Bonvoy. All of my personal spending goes on the Chase Sapphire, except personal flights (Chase United Explorer) and personal hotels (AmEx Marriott Bonvoy). I put all of my spending on the Sapphire because it accrues Chase Ultimate Rewards points, which are super flexible on redemptions in various ways. I use my Sapphire when traveling internationally as well–contactless payment is de facto in western Europe, which Sapphire cards have.
Personal travel accounts for maybe 10% of all travel, so the other 90% goes on the company’s American Express Platinum card. I’m giving up a loooot of points for this, but it means no expense reports for me and simpler bookkeeping for my CFO.
All told, I spend about $50,000 per year on travel. It’s a decent chunk of money and helps to explain why it’s worthwhile for me to put so much effort into this. I expect that number to increase over time as I travel more and more for clients.
I reevaluate how I travel on almost every trip, always looking for the next optimization to make traveling more comfortable, convenient, or consistent.
One area I’m still noodling on is how to better support exercising and eating well while traveling. My bag is already full so adding gym shoes is a major sticking point. Nevermind the issue of what to do with sweaty gym clothes. And I still have to figure out the matter of where to workout: while most hotels have a fitness room, they are generally poorly equipped, which means I’d have to find a proper gym somewhere near the hotel. Not insurmountable problems, but I haven’t figured out good solutions yet.