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Pro-Tip | Travel

Updated: Oct 20, 2023

Lessons learned from an 18+ year road warrior, plus an answer to the existential question "why am I here?"

Spoiler alert: I am not.

A view of New York City from my plane window

Those of you who know me well, know I spend a *significant* time on the road. I realized recently, other than a brief hiatus during the pandemic, I have been traveling greater than 50% for around 18 years. I was in Canada when they implemented the “take your shoes off, no liquids greater than…plastic bag…” rules. Bonus, I was flying to Washington D.C. I have also traveled on dozens of September 11s, Friday the 13ths, and just about every one of my birthdays. This work lifestyle may or may not have contributed to the end of my marriage and perhaps a relationship or two. All in all, if you can travel for work it can be rewarding, but also comes at a great personal cost. I do not have a pet. I do not have a houseplant. My fridge is not stocked. I am a regular at restaurants and bars that are 1000s of miles from home. It isn’t okay.

Today, as I crossed yet another security checkpoint in what has been a whirlwind international trip that has had me in Switzerland, Bulgaria, Germany, Washington D.C., and Denver, I recognized how efficient I am (as I should be) at navigating airports, airport security, hotels, car rentals, etc. And this morning, in particular, I noticed how many folks make novice moves that frustrate them and cost them time and sometimes flight misses. I thought I would post some of my lessons learned here…. Cuz why not.

First, a note about “costs.” Obviously, we all want to save money when we travel. No one wants to overpay for a flight or a hotel, and you shouldn’t. But your overall calculus should not be that simple. Because sometimes we sacrifice the *real* cost to save money. Time. Time is the one valuable resource we cannot get back, or recoup. Time is especially important when we are on a trip. We have paid money to get here. We have taken our precious vacation time from work. Or we are on a work mission, and the office to-dos are piling up while we navigate the “ground war,” as I call it. I don’t know about you, but it is difficult to be effective and motivated after 10 hours of travel and meetings, to get those emails done when I return to the hotel that evening. In this, you must be efficient with your travel time, and work tactically between obligations on the road.

Choosing Flights

How do you manage time? First, I have never been a fan of airline loyalty programs, or loyalty programs in general. They are seldom worth *your* sacrifice, which is often time. I have always flown whichever airline gets me to my destination more directly, on the time table that I require, and most efficiently. I absolutely will not fly an airline to get “points” that requires a time or connection that isn’t necessary. I will even pay more for an airline that does meet those requirements. Think about this carefully, how many times have you gotten stuck at a connection, missed a connection, ended up wasting a day of your vacation because of a connection mishap? Don’t do this, it isn’t worth it. Get to your destination on time and directly whenever possible.

Airport Security and Packing

Almost hypocritically, I do not have TSA pre-check. I know, some of you are probably screaming at your tablet screen right now. I honestly have no reason other than I have not made the time to go to sign up and do the “interview.” This is helpful for you, because I am going to tell you what I observe in the regular airport line. (And much of this would apply in precheck, also.) First, get yourself a bag that fits easily in the overhead, or a backpack that fits underneath the seat in front of you. This prevents losing your bag, waiting at the baggage claim, and makes navigating the airport MUCH easier. Stick with me here. I travel with a single backpack from CotoPaxi. I use this bag regardless of the length of my trip. This bag is easy to carry, has shoulder straps, chest straps, and has concealable waist straps, like a multi-day hiking pack would have for shoulder support should you need to walk long distances. The best thing about this bag is it fits in virtually any overhead (yes, even in those tiny regional jets) and underneath most seats. You might be saying to yourself, “but Kurtis, I need to carry many things.” Yea, me too. On this trip, I have two full suits, three dress shirts, dress shoes, dress belt, workout clothes, something to sleep in, three casual shirts, an extra jacket, my bluetooth speaker, cables and such, a journal, my iPad, some motorcycle magazines to read on the plane, an electric toothbrush, a second smaller bag to carry my iPad and documents in, and my bathroom bag. My bathroom bag contains toothpaste, eye cream, face cream, serum (yea, I have a pretty rigid skincare routine), cologne, essential oil, dry shampoo, pomade, fingernail / toenail clippers, tweezers, and some meditation beads. I also have my health supplements. In one backpack. It can be done. Perhaps I will do a short separate blog on how I achieve this. If you bothered to read this and want to learn my packing tricks, shoot me a comment or an email and let me know.

Let me explain what this does for me. Two days ago I landed in D.C. and had to get on one of those dumb people movers at Dulles airport. They dump you at the passport control at the main terminal. Despite the fact I was near the back/middle of the transport, all the other passengers jumped on the escalator and stood there as it slowly descended to the passport control as I walked past them down the stairs and was at the front at the bottom. This will happen repeatedly throughout your airport experience and you will end up getting where you want to go much more quickly. Further, no one ever touches my bag but me - I don’t have to worry about the security of my things, I don’t have to worry about it getting lost. Finally, I can change my mind / flights on a whim - I have all of my things on my person at all times. Consider this strategy. (It is also good for health reasons.)

Dumb "people movers" at Washington Dulles Airport

What to wear at the airport

This is going to depend a lot on the weather. Generally, you want to wear what is comfortable and will be efficient through security. In the winter months, you may bring layers that can help you build better outfit ensembles later in the trip. I have two kinds of shoes with me at the moment. I have my dress shoes in my bag. I stuff my socks and extra belt inside those shoes to save space. I am wearing a pair of Arc'terix Aerios shoes. I like these, because they look very nice, and could be worn with jeans and a dress shirt. They are also trail running shoes, and I did use them for that purpose on this trip. Best thing about them is they are extremely comfortable and slide on and off easily. I am also taking advantage of the layering on this trip. While I type this, I am wearing a pair of jeans, my Arc'terix shoes, a dress shirt, a pull over sweater, and a light vest. I can reuse the dress shirt in my suit outfits, the sweater as a layer anytime (making my other dress shirts more versatile.) I can also use the light vest in this way. My jeans are from Theory and they are comfortable but look nice enough to wear with dress clothes.

Airport security (or train) tips

When you get to the point where you are about to grab some bins…. If you have a backpack or rollerbag, do not put it on the table / belt yet. Take out your electronics first, put them in a bin un-stacked, then stack the next bin on top of them. Take your cell phone, and anything in your pockets and put it in that bin, or I often put them in the pockets of my vest or jacket layer. Put that in the bin. So far, you have the profile of a single bin on the belt. Most airports, even though the signs may say otherwise, do not require you to take out your bathroom goods any longer. I am going to say i experience this less than 10% of the time now. So try that, leave your bathroom kit in your roller bag or backpack. 90+% of airports will not make you take off your watch or jewelry, either. Put your shoes next to your jacket, phone, etc. Belt if you have one. You still have the profile of a singe bin. Keep your roller bag at your side and your backpack slung over your shoulder and walk your bin toward the machine. When you reach the machine, put your roller bag, and backpack on *before* your bins and just before the belt pulls them into the machine. If you put your laptop or tablet in your backpack, put that first and leave the zipper open. Just as the bins come to the belt, unstack them. Now you are good to be groped by airport security. On the other side, after you have made your new TSA friend, you can do the reverse. Take your electronics and put them back in your bag, sling it around your shoulder, put your roller bag on the ground. Grab your jacket put it on, grab your belt and shoes. Walk to a bench. Finish getting dressed for the second time that day. It is that simple, and it is fast. I see people put their roller bag on the table and then bins one at a time in serial. Then proceed to try to push those items down the table while undoing things, taking off belts, etc. It is unnecessary.

A word on patience

This is extremely difficult to do in practice but…. In Steven Covey’s famous book “The Seven Habits of Highly Effective People” he opines on “sphere of influence.” There are things that are within your control. Those things, you should focus on and try to influence. Most things, though, are not. This includes how other people behave, the weather, the universe’s plans, and effing flights. Try to remember this when your airline didn’t think to call the de-icing truck in advance of you boarding or neglected basic maintenance. Yea, they are asshats, but you cannot control that. Take a deep breath, and let it go. Find something to occupy your mind that is productive. I listen to podcasts, meditate, and recently have been listening to apps for this purpose like “Waking Up” and “Calm.” Write a blog to convince others you know what you are talking about ;)


Choosing a hotel is fundamental. My criteria are typically this: Is it close to my meeting or where I need to be? Is it reputable / clean enough that it is unlikely I will get bed bugs? (I have had this happen and it cost my thousands of dollars to recover.) I also look for a hotel that has a convenience pantry / store, a bar, and most importantly a fitness center. Your requirements may vary, but the one that likely will be universal is proximity to your objective. Do the math on this. Do not pick a hotel that is 100 dollars a night cheaper, but you have to spend time or money on transit or Uber each day to get where you need to be. It adds up, and often can quickly eclipse your hotel nightly rate savings.

Where in the hotel? You don’t want to be close to the elevator, and I prefer to be on a lower floor if possible. I don’t know about you, but in most cases, I am not on this trip to enjoy the view from my hotel window. If you have ever tried to leave a high rise hotel at 8am on a Tuesday, and sat in the crowded elevator while people smush in like a train in Tokyo at Every. Single. Floor. …you will appreciate what I am suggesting here.

A note on AirBnB

I don’t like them. I have had poor experience after poor experience, ranging from waiting hours for the person to bring me the keys as they commute from another city, dirty and stained sheets, strong smells of weed, drag paraphernalia in the unit, lack of sundry goods, coffee, and even being accosted by the building management because the person did not have the right to even rent me the AirBnB. I don’t have time for this and AirBnB’s customer service stinks like the weed smell emanating from the pillows in the apartment. My one exception for using AirBnB is if you can rent a high end property for vacation or for a group of people at a nice destination. I have had challenges with these too, but they are often trumped by the value of the rental.

Rental cars

Choose a brand like National or Hertz that allows you to book online and then just walk to the car and drive away. No need to spend 10 minutes doing a walk around with a clipboard, or standing in line at the rental counter. Get in the car and drive away. For the most part and on most trips, it doesn’t matter what car it is - I try to choose small fuel efficient cars, as they are easy to park and economical.

A note on Uber

I don’t like them. Yet, I use them frequently. It is also hard math to figure out whether to rent a car or just Uber around a city. Keep in mind, though, between valet and parking costs, likelihood of an incident, fuel, etc, that your inexpensive rental will add up quickly. Most metropolitan cities in the US will be charging you between 30 and 80 dollars a DAY for parking. Each time you visit a new destination, minimum 20 dollars in parking fees. Gas is no longer cheap. This is why I bite my lip and Uber or Lyft when I can. For Uber, I am usually using the more premium service, as I have been in some shitty, smelly, dirty cars - the driver wreaking of weed or general BO. if you have to Uber, Uber Black. Lastly, you can accomplish more in a car share. I can work, take notes, reply to messages, or if ABSOLUTELY necessary, make a call. I try to avoid making any calls during Uber rides, because of security reasons. Uber drivers are people too, and they likely understand what you are saying. Many of them are doing this as second income and may even work in your industry. Careful what you say in a car share.

Choosing a method of transport

This is often a tricky equation. It depends on the time of travel, what your connectivity requirements are, etc. The important thing to understand is the time commitments of the transportation methods of choice. Obviously we all understand what effort is required to get in the car and drive somewhere. Typically the most deterministic method of travel - barring traffic, road closures etc. The other advantage is when your are finished with your business, you can depart on your time, not anyone else’s. The downside is you cannot do much else while driving. You *could* make calls, but it is tough. Trains are nice for trips that are four or less hours and do not require transfers. You can work on the train, it has internet access, and is relatively easy to navigate the terminal / security. When choosing between other methods and flying, make sure you understand what time it takes for you to 1. Time to drive to the airport 2. For domestic flights 1 hour buffer, for international 2 hours 3. Flight time 4. Transport from the airport to your objective location. This can add up, and usually minimally is 4 or more hours, cumulatively.

A few other items

Food and timing of food can be a pain in the ass when traveling. I have a crazy metabolism and when I get hungry I get HUNGRY. Bring snacks, and make sure they are accessible. Make sure you have some on you while in transit, but also in your hotel so if you wake up hungry, and no breakfast is available at that time, you have something to keep you satiated. Drink water and avoid overdoing the alcohol *during* the travel process.

  • Bring aspirin / ibuprofen

  • Make sure your power plugs, earphones are easy to get to

  • Use mobile boarding passes whenever possible

  • Have pictures of your IDs, passport on your phone

  • Use Kindle and Audible

  • I use an iPhone, I turn on battery save immediately and turn off Wi-Fi and Bluetooth until i need it

  • Chewing gum or mints are nice to reduce “travel breath”

  • Use the restroom gratuitously when you have time

  • On long flights, get an isle seat toward the front / middle of the plane

Some operational security tips

  • Practice situational awareness

  • Never leave your items unattended anywhere (including trusting them to strangers)

  • Do not post where you are on social media until you are gone from that place

  • Do not talk loud in hotel rooms, the people next door can hear you

  • When on calls in public, use only one earbud so you can understand your volume

  • Avoid calls in car shares

  • Delete your phone from the bluetooth in rental vehicles when returning it

  • Use a VPN on all devices at all times

  • Use a privacy screen on your iPad or laptop (I use one that is magnetic and I can remove when I am not on a plane or train, airport etc.)

  • Do not get overly intoxicated ever, EVER

  • Avoid walking alone at night


  • Be patient

  • Be kind - help others, even if they are annoying you at their inexperience

  • Give up your seat for the family that wants to sit together

  • Help the elderly

  • Buy that person next to you a drink (no need to be overly social, some people don’t want to talk)

  • Don’t assume that others are in the same situation as you, many people are suffering for one reason or another. They may not be going to a work meeting or vacation, but to a funeral or a cancer treatment

  • Avoid joining negative group thinkers (this occurs when there is a flight delay / cancelation) Focus on your mission (also, sometimes it is easier to call it. Get a hotel, start over tomorrow.)

  • Smile, this is a privilege that many will never experience


Travel is a gift and a curse. But the more thoughtful you are about the process, planning, and patient you will have a much better go at it. Ultimately, things will go wrong and it won’t go your way…maybe very often. Accept this and focus on your sphere of influence. Be mindful of your time, it is your most precious resource, book smart, travel smart, and stay smart. I am sure my fellow road warriors will have other strong opinions on these and other related topics. Comment and let me know, reach out if you have tips for me. Peace, and safe travels!

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