10 tips for making travel easier

Maximize your waking hours at home, and minimize your waking hours on the road

I travel a lot. Every year I speak at about 50 law schools and lawyers groups across the country. On average, I fly approximately 100,000 miles per year (almost entirely on United). And I spend roughly 80 nights a year in hotels (almost exclusive at Marriott properties.)  I recognize this schedule is not for everyone, but I have developed a system that makes it manageable. In short, I maximize my waking hours at home, and minimize my waking hours on the road. Here are ten tips I abide by, that may make your travels easier.

1. Where feasible, choose early morning flights over late-night flights the day before.

Virtually all of my trips are same-day jaunts. I recognize this option is not feasible for everyone, but it works well for me.  I can take an early morning flight (usually before 7:30 a.m.) to just about anywhere in the country, and arrive in time for a lunchtime event. And I can usually catch an early afternoon return flight (usually around 3:00 p.m.), and be home in time for dinner. This schedule minimizes my time on the road. Often, groups will invite me out to lunch, or dinner after the event. Where feasible, I propose brunch instead. That is, we eat after I land at the airport, and before the event begins. That scheduling option allows me to quickly get out of town once I am done speaking. There is a huge difference between getting home at 7 p.m., and getting home at 9:00 p.m.

Only in rare circumstances will I fly in the night before, and spend a night in a hotel on the road. First, some invitations require me to speak in the morning--a noon arrival time is not sufficient. Second, some flights will not arrive early enough in the morning to make it work. For example, I cannot get to Boston in time for a noon talk. The flight-time is too long. And I cannot make it to Seattle or Portland in time--even with the time-zone changes, the flight is too long. Fortunately, Houston is roughly in the middle of the country--I can make it to New York, Chicago, and Los Angeles in three to four hours.

2. Avoid connecting flights where feasible.

I will only take a connecting flight in rare circumstances. Too much can go wrong. You have to worry about the inbound flight in your starting airport, and your inbound flight in the connecting airport. And if there is a delay, you have the stress of knowing you will have to run through the terminal. Flight attendants will often tell you "they'll hold the flight." They won't. I once got stuck in Phoenix after I missed a connection on American. The door closed about a minute before I got to the gate.

I am fortunate to live near an intercontinental airport. Indeed, one of the biggest perks of teaching in Houston is the airport. I recognize people who live near smaller airports will have to take connections.

3. For early morning flights, consider staying at the airport hotel in your home city

Early morning flights are rough. A flight that leaves at 7:00 a.m. will board at 6:30 a.m. Delays in the morning can be mitigated by signing up for TSA-Pre, as well as Clear. These options allow you to zoom through security at most hours of the day. I seldom wait more than 5 or 10 minutes at any airport I visit with these features. Even so, getting to the airport at 6 a.m. is not easy. (I will discuss my approach for airport travel in the next section). About a year ago, I figured out a method to minimize the stress of an early-morning flight.

The George Bush Intercontinental Airport in Houston has a Marriott hotel on property. The interterminal train stops at the hotel. When I have an early morning flight, I usually spend the night at the Houston hotel. Specifically, around 10 or 11 p.m., around when I would usually go to sleep, I head to the hotel. I arrive at the hotel, and go right to sleep. (I have no problem sleeping at hotels.) This option lets me shift the commute from early in the morning (when I am half-asleep) to late at night (when I am wide awake). Let's assume boarding is at 6:30 a.m. If I am staying at home, I would usually wake up around 4, leave for the airport around 5, arrive at the airport around 5:30, and clear security by about 5:45. But if I am staying at the hotel, I can wake up at 5:30 for a 6:30 boarding time. So long as I am on the interterminal train by 6:00, I can get to my gate well before boarding. And with this option, I don't need to worry about traffic or last minute delays in leaving the house. The bulk of my 80 hotel stays every year are in Houston.

Many international airports have hotels on property: Philadelphia, Atlanta, Detroit, San Francisco, O'Hare, Newark, to name a few. Some of these hotels require taking a bus shuttle. I do not prefer those hotels, because busses run on irregular schedules early in the morning (maybe every 15 minutes). The ideal hotels are those you can walk to through the terminal, or take an automated transportation system.

4. Do not drive to the airport. Uber there, and taxi back.

Over the past two years or so, I have more-or-less gone full Uber. I Uber to and from work, and most other places.  I can easily work in the back of the car on my laptop, or take a nap if I'm tired. This approach, which is not cheap, has helped me generate between five and ten hours a week of found time. Even if you aren't willing to take the plunge, I encourage you to consider avoiding the drive to the airport. The process of finding a garage spot can often be stressful, especially if lots are full. And that search may add 10 or 15 minutes to your commute. Ubering to the airport eliminates all of those problems.

But, I would not recommend taking an Uber from the airport. Invariably, the wait times are more than 10 minutes. And far too many Uber drivers engage in a scam: (1) you call an Uber, (2) they do not move, and call you ask where you are going, (3) then they say they will not drive you, and ask you to cancel the ride. I don't bother anymore. I simply hop in a taxi from the cab line. They are always available, and will take you wherever you want to go. The price is more, though it becomes more reasonable during surge times (early in the morning, and during rush hour).

5. Take a risk: don't get your destination too early, and don't wait too long at the airport.

TSA recommends arriving at the airport two hours before your flight. This recommendation creates an absolute waste of time. I try to arrive at the airport about 30 minutes before boarding. In some cases, I've arrived 15 minutes before boarding, and was fine. (TSA Pre and Clear are essentials for this approach.) Taking a risk on this front will allow you to spend more time at home.

Moreover, I try to arrive at my destination with about an hour to spare. For example, if my event starts at noon, and there is a 15 minute ride from the airport to the destination, I will try to land around 10:45. But what about delays, you ask? Generally, flights that leave first thing in the morning have the fewest delays. Those airplanes are generally parked overnight from late-night arrivals. You do not have to worry about a delayed inbound. Flights later in the day are more likely to be delayed, because of delays that occurred throughout the course of the day. I have been using the one-hour rule for nearly a decade; it caused me to be late for an event only once. Several years ago, on a trip to Detroit, we waited on the tarmac an hour for de-icing. Even then, I managed to arrive at my event around 12:20. Not the end of the world.

6. Do not check bags, and limit what you carry through the terminal

When I travel alone on short deadlines, I never check bags. It takes additional time to check a bag at the terminal, and then additional time to wait for the bag upon arrival. Some smaller regional jets have limited overhead space that will not fit standard roller-boards. For those flights, bring a smaller roller-board. Waiting on the jet-bridge (where there is no climate control) is a waste of time.

Also, limit what you carry through the terminal. I have one roller-board, and my laptop bag. The laptop bag has a special flap, that allows you to put the handle of the roller-board through it. In other words, the two elements come one. I can hold onto the handle, and wheel both items through the terminal at a quick speed. That approach leaves my other hand free. I much prefer a roller-board with two big wheels, rather than the four small wheels. The latter are easier to navigate around sharp turns, but are harder to walk with at a fast clip. Also, the four-wheeled versions take up more space, and give you less room to pack.

When you are in the terminal, do not carry extra items in your hand. You will put them down somewhere, and forget them. Any food I buy goes either in my laptop bag, or in a plastic bag I drape over the roller-board handle. Everything is together. I always keep my jacket in the suitcase. It is too tempting to put a jacket down on a chair, and walk away without it. But doesn't my jacket get wrinkled?

7. Do not worry about wrinkled clothing

When I first started traveling, I took steps to ensure that my clothes would not be wrinkled. I would carry a separate valet, where my suit and shirts were neatly folder. I would have to check this additional carry-on. Or I would gently lay my suit jacket on the overhead bin. (Invariably, someone put their suitcase on top of my spot). At a certain point, I said "forget it." My clothes will be wrinkled, and I will be fine. I do ask the cleaners to fold up shirts, and place them in plastic wraps, rather than put them on hangers. This process makes transporting shirts easier. But suit jackets, ties, and pants are wrinkled. I'm okay with it.

8. Consolidate your flights and hotel stays to accrue loyalty status

I am fortunate to live in a city with a United hub. Almost 90% of the flights I take are on United. As a result, I maintain what is known as Premier 1K status. The biggest benefit is that I can board early. And, in theory at least, I can clear for upgrades (though those upgrades are increasingly rare.) There is another benefit that is less well-known. When a flight is cancelled, United will rebook you on another flight, and you leapfrog to the top of the standby line. That perk has ensured that I get home in time, versus spending the night in a random city.

I also primarily stay at Marriott Bonvoy properties. Here, the biggest parks are early check in (around noon) and late-checkout (around 4:00 p.m.). These features allow you to maximize flexibility of travel. If I need a late checkout at a non-Marriott property, I am usually able to pay an additional amount, or simply book a second night.

9. Where it saves time, consider mixing and matching airports/airlines

In the previous tip, I urged you to consolidate all of your travels on a single airline and hotel chain. But in some cases, it is useful to mix and match. For example, if I have a lunchtime event in Salt Lake City, I take a 6:00 a.m. flight on Delta, but return home on a 3:00 p.m. flight on United. Or if I am flying to Chicago, I may fly inbound on Southwest to Midway, and outbound from O'Hare on United. (This option requires ubering to the airport, as I take off and land at different airports in Houston.) And if I am staying at a conference hosted at a Hilton or Hyatt property, I book that brand--you save time coming and going from the airport. Get creative with your booking. You can minimize how much time you spend on the road.

10. Don't stress

Travel can be stressful. If your flight is delayed, nothing you can do will eliminate the delay. Nothing you say to the flight attendant will remove the delay. If your flight is so delayed that you will miss your event, simply walk off the plane (if the door is open) and reschedule. People understand bad things happen. But don't get irate at things. Don't mutter and complain. Everyone on the plane is in the same boat. Use that additional time to get work done, or focus on some other matters. Don't stress.