Hello everyone and greetings from 35,000 feet!  I am on the road again – my third trip in April.  I think I have spent more days sleeping in hotel rooms than I have at home this month.  I am not complaining at all, but I do spend a lot of time on the road.  And that got me thinking about all the things that have gone wrong over many years of hard travel.  It’s a lot.  But, like many of my blog topics, I screwed up and then learned the lesson.  The same is true with traveling.  I know not all in-house lawyers travel a lot, but they do travel.  And it is always better to be over-prepared than to get smacked upside the head by the cold, hard, fickle hand of Fate (she is indeed a tough mistress who enjoys smacking people upside the head).  I was going to write about mentoring programs, but (as I sit here on the plane) I decided this was a more interesting topic – at least to me.[1]  So, instead of mentoring tips, I am going to pass along some tips I learned (the hard way) over many years so you can travel better. I am writing this with the assumption you will carry on your luggage vs. checking a bag.  First tip: Never check a bag unless you have no choice.[2] See how easy that was?  But brace yourself, as there is more.  A lot more.  This edition of “Ten Things” sets out my top travel tips for the busy in-house lawyer:

1.  Get a good suitcase/backpack.  Unless you travel as often as Halley’s Comet streaks through our skies (every 76 years, just in case you needed reminding), invest in a quality carry-on suitcase and a good backpack.  On the road, your suitcase is your closet, and the backpack is your office.  Cheaping out on either will ultimately bring misery to your door (and who needs that shit?).  Here’s what I recommend:

• Suitcase: on the high-end (i.e., pricey), I would go with the Briggs and Riley 22” carry-on with built-in garment bag.  The garment bag side will keep your suit or dress unwrinkled with plenty of room for the rest of your clothes.  On the low-end (much less expensive) is the Modoker rolling garment bag.  And if you search a bit, you can likely find something in between, like the Halfday Carry-On Garment Roller.
• Backpack: a good backpack will have plenty of room for all your gear (and maybe room for a few pieces of extra clothing in a packing cube).  Here’s my pick: the Beraliy Travel Backpack.  Close second: Matein Carry-On Backpack.
• Packing cubes:  at first, I laughed at packing cubes, now I cannot travel without them.  Get a good set and feel what it’s like to arrive somewhere without clothes so wrinkled that someone mistakes you for a California Raisin.  Here’s my recommendation: Amazon Basics Packing Cubes. 
• Luggage tags.  Not sexy, but get something distinctive so you can flash a little color and easily find your bag when you need it.  In a world of black carry-on bags, they all look like yours!  Here are some fun luggage tags to get you started.
• Apple AirTags.  Always know where your stuff is.  AirTags are perfect for this.  Put one in each bag you bring (including your backpack). There are cheaper options available, too.  It doesn’t matter what you get; just get something to keep tabs on your stuff.

2.  Create a go-bag. If you travel frequently, having a TSA-approved-size clear plastic bag to pack with your toiletries is a must.  Once you create it, you just forget about it and toss it in your suitcase when you pack for the next trip. Your go-bag will hold shampoo, conditioner,[3] toothpaste, eye drops, and any other liquids or gels that need to be 3 oz. or less.  You can buy a TSA-approved size bag or just use a quart-size plastic bag (which is what I do).  You can also buy travel-size versions of most of your favorite products (there’s even an online store for just that!) or buy some TSA-approved size containers.  Another plastic bag will hold razors, dental floss, favorite soap, ChapStick, or any other non-liquid/gel that you always take along when you travel. When you get back from a trip, refill/stock everything, and it’s ready for the next time you hit the road. I also take along a gallon bag and an extra quart-size bag when I travel because they have come in handy numerous times.

3.  Gear.  Almost as important as your clothes is your gear.  Your laptop and smartphone are a given.  Here is what you need for your traveling office (with my recommendations):

• Extra charger cord (and just leave it in your travel backpack so you always have it with you).
• Portable second screen (if you are a two-screen fanatic).
• Noise-canceling headphones or earbuds (babies crying, the traveling baseball team of 11-year-olds staying on the same floor as you, etc.).
• Privacy screen for laptop (you don’t want people reading your stuff).
• Portable charger block (that can charge your laptop because you cannot depend on airplanes to have working power outlets).
• Extension cord with multi-plugs (because sometimes the hotel room has no plugs anywhere near the desk – yes, I am looking at you, Westin).
• Portable lamp (so many times I wish I had this).
• Portable fan (helps you sleep and keeps you cool at night).
• Travel mouse (save your hand from cramping!).
• Cord case (you are a grown-up – get a cord case).
• VPN (please do not connect to public wifi without a VPN – you are a lawyer and are transmitting confidential and privileged documents and communications).  I like Nord, but there are lots of reputable services out there.  Do not use a free one.  Free means a guy in mom’s basement Hoovering up your data.
• Mini cleaning brushes (for your phone – nothing is worse when you travel then have your phone not charge and all you need is a damn little brush to clean out the connection.  These are life savers people!).
• Multi-cord charger cable (one cord, five different charger ends – you will never be without the right charger cord again).

I know this seems like a lot, but I believe these are essential to keep your sanity on the road and ensure you are always able to work when needed.

4.  Pre-Check/Global Entry.  If you travel more than once a year, get TSA Pre-Check.  If you want to spend the extra dough, get Clear.  If you travel internationally, add Global Entry to your TSA Pre-Check.  If you don’t have Pre-Check, see footnote 2.

5.  Loyalty programs.  This one is easy.  For every airline, hotel, or rental car you use, join their loyalty program.  If you can concentrate your travel on one of each, that’s great as it’s likely you will get status and potential upgrades, discounts, snacks, drinks, free checked bags (if that is ever needed), etc.  But, for most, just joining will get you something, like free internet, better boarding priority, or an upgraded car. And the higher your status, the faster you will get rebooked or reaccommodated in the event of a flight cancelation or a hotel overbooking.

6.  Hotels.  I am going to assume you are somewhat like me.  It’s tough enough to sleep on the road, and anything you can do to make your hotel stay more enjoyable, you are willing to give it a try.  Here is my list (and as usual – in no particular order):

• Ask for a high floor (less noisy).
• Splurge for the club floor room (if available and not outrageous) – free food and drinks, a nice place to work, and less “crazy” going on.  Especially now since the lobbies of most hotels are blasting loud music and are stuffed with people who feel the need to yell everything they say or speak extra loudly into their mobile phones because whoever the hell they are talking to cannot hear worth a shit (and they are on speaker mode so they can double their stupid quotient). 
• Eye mask/earplugs. Eye masks are terrific for helping you fall asleep or catch a nap during the day.  Earplugs are a cheap version of noise-canceling headphones.
• Ask for a room away from elevators/ice machines (less noisy).
• Ask for late check-out and early check-in (more likely to have your room ready when you arrive and sometimes an extra hour or three before you have to check out can save the day.
• Bring along a couple of chip clips (clips to keep bags of snacks closed) and use them to join the curtains together so you do not get the blinding strip of light that bursts through when they don’t join up properly.  You can also use one of the hangers in the closet to join the curtains together if the hanger has clips for pants. 
• Locate the nearest Walgreens or CVS.  You never know when you might need something, and they have just about everything you might need in a pinch on the road. Figuring out how close your hotel is to one or the other is playing it smart.
• Toss a few Keurig pods of your favorite coffee in your bag.  Many hotels have Keurig machines but terrible coffee pods.  At least drink something you like!
• Sign up for DoorDash or Uber Eats.  Not only might you need some food delivered, Uber Eats can also pick up things from Office Depot when you have forgotten to bring office supplies.
• If the room is not to your liking, go back downstairs and change it or leave.  I have done this several times.  If the room is too noisy, the temperature isn’t good, it doesn’t feel safe, or whatever.  You don’t have to stay in the hotel you booked. Make them work to keep you.
• Most importantly, if you have asked for a high floor, away from elevators, late check-out, etc., confirm all of this when you are checking in.  In my experience, it seems like 50% of the time, no one at the front desk knows you asked for anything special, and when you get to your room on the second floor by the ice machine, you may not have it in you to go back and get it fixed.

7.  Airlines.  No getting around this one.  If you have to fly, expect it to be miserable.  Here are some tricks of the trade that can help:

• If you are leaving from a new airport or terminal, go to your gate before you do anything else.  Airports are not built logically; many gates have been added where space permits, meaning Gate 5 and Gate 4 can be a long way apart.  And there is no worse feeling when you leave the airport lounge or food court than realizing that your gate is nowhere near where you thought it would be.  Run Forrest Run!
• Book flights early in the morning – less likely to get delayed or canceled.
• Join an airline club or one of the generic clubs like PriorityPass.  If you have an Amex card, get the level that gives you access to the Centurion Lounge.  Capital One cards now come with access to Capital One clubs.  Chase cards can get you access to PriorityPass lounges.  Here is a list of the top seven credit cards with club access. Bottom line here is that if your flight is delayed or you are early or you need to take care of something right after you land, an airport club/lounge can make all the difference.  A day pass works just as well (if available).
• If the weather is bad and your flight starts to get hit with rolling delays, don’t wait for the airline to cancel it.  Book another flight for the first thing the next morning.  If you don’t need it, you can cancel it within the first 24 hours of booking any flight without penalty or cost (DOT rule).  If you wait until the flight is canceled, everyone who already knows this trick has scooped up the good flights, or the flight the airline books you on is two days away with a middle seat in the last row by the bathrooms.  Take control of your flight destiny! 
• If you do get stuck, do not use the airline-provided hotel.  They are usually shit and there will be a mad dash of people all headed to that hotel.  Instead, use a travel app like CheapOair, Expedia, or Priceline to book your own hotel (or if there is a hotel connected to the airport terminal, try that one).  Yes, it will not be “free,” but trust me (and I say this from experience), free is overrated when it comes to hotels booked by airlines for passengers whose flights are canceled.

8.  Power up.  Before you step on that plane, be sure your laptop and smartphone are fully charged.  You cannot count on the power outlets working on airplanes (as I found out the hard way on this trip because I forgot to pack my damn portable charging block). 

9.  Sanity kit.  Besides your go-bag, be sure you pack the following in your backpack (and not in the suitcase, just in case that has to be checked for some reason):

• Entertainment.  Make sure you have music, podcasts, books, newspapers, etc., downloaded on your phone or tablet before you leave the house.
• Food.  Once you get on an airplane, you never know when you will get the chance to eat again.  Even if you are in the front of the plane, the food choices may suck or they only have fish or they forgot to cater the plane at all.  Bring a few packages of protein bars, trail mix, nuts, or whatever.  Just enough to get you through a bad flight or no dinner options when you get to the hotel.
• Medicines.  Prescriptions, over-the-counter, etc.  Whatever you normally need during the course of the week, take it with you.  My short list: 
  • Prescriptions.
  • Pain reliever.
  • Over-the-counter sleep aid.
  • Laxative (don’t laugh – you’ll be thanking me when you need it).
  • Dramamine.
  • Tums/Alka-Seltzer.
  • Mucinex + travel pack of tissues
  • Small first aid kit (don’t laugh – when you need a bandage, you’ll be thanking me).
• Sewing kit.  If you have ever lost a button, you know why you need this in your sanity kit.
• Book.  Sometimes all the electronics fail, and then where are you – sitting on a plane with two hours to go and nothing to do.  Toss a paperback into your backpack and hope you never need it.  My choice?  The Gray Man series or The Last Kingdom series.
• Extra glasses.  If you wear glasses (like me), pack an emergency pair just in case.  I broke my glasses once and did not have a second pair.  Fortunately, I was in NYC and found a one-hour optical right by my hotel.  You don’t always get that lucky.  Pack the extra pair!

10.  Plan on one extra night.  Boy, one lesson I have learned is that it is not unusual to have to spend an unplanned night when traveling.  I always pack “one-day-extra” of everything, i.e., an extra shirt, socks, meds, or whatever.  Hopefully, you never need it, but when it dawns on you that you are not getting out of town when planned, you’ll be glad you packed a few extra things. Bonus tip: if you are wearing a suit or blouse during the trip, bring an extra dress shirt or blouse just in case you spill coffee or get ink all over it. Yep, that was me.

*****

Alright, everyone.  Those are my top ten travel tips for busy in-house lawyers.  If you are a seasoned road warrior you probably know much of this already, but hopefully there was at least one or two new things from the list above.  If you are new to the road, there is no glamour.  You could be in Rio or Pittsburgh, and sometimes it all looks the same.  But if you plan properly, you can make it a little less painful.  If you have any travel tips to share, post them in the comments here in the blog or on LinkedIn.  And most importantly … sorry, they just asked us to put away our laptops as we are landing.  Travel well my friends!

Sterling Miller

April 30, 2025

Here is a bonus “Night-Before-Travel Mini Checklist” (or make your own)

1.  Devices charged:

☐ Laptop 100%
☐ Phone 100%
☐ AirPods/headphones charged
☐ Backup charger packed and full

2.  Documents ready:
☐ ID/passport in wallet (and photo of same saved on phone)
☐ Boarding pass downloaded
☐ Hotel confirmation saved
☐ Meeting agendas, contracts, and notes synced offline

3.  Essentials packed:

☐ Work laptop + charger
☐ Phone charger + universal adapter/voltage converter (if international)
☐ Business cards (yes, still)
☐ Notepad + 2 pens (meetings always need backup pens)

4. Personal kit check:

☐ Toiletries bag (toothbrush, deodorant, lip balm, moisturizer)
☐ Minimal makeup/grooming essentials
☐ Meds (rx, pain reliever, allergy meds, anything critical)

5. Outfit prep:

☐ Tomorrow’s airport outfit ready (comfortable but polished)
☐ Meeting outfits packed (double-check shoes, socks, belt match)
☐ Light jacket or scarf (planes get freezing)

6. Backup plans:

☐ Copies of ID and itinerary in cloud folder
☐ Local office or client contact info saved
☐ Emergency $50-100 cash and back-up credit card hidden in bag

7. Security/safety:

☐ VPN app tested and working
☐ Two-factor authentication codes accessible offline (for work systems)

8. Home front:

☐ Out-of-office reply drafted (if needed)
☐ Calendar blocked for travel downtime (especially after red-eyes)
☐ Home logistics handled (mail hold, pet care, let loved ones know your itinerary, etc.)

My latest book (number six), The Productive In-House Lawyer: Tips, Hacks, and the Art of Getting Things Done is now available for sale.  Like the ABA says, “If you are stuck on a plane, this is the book to have!”  That pretty much says it all!  You can buy your copy here: Buy The Book!

My fifth book, Showing the Value of the Legal Department: More Than Just a Cost Center is available now, including as an eBook!  You can buy a copy HERE.

Two of my books, Ten Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies and Ten (More) Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies Volume 2, are on sale now at the ABA website (including as e-books). 

I have published two other books: The Evolution of Professional Football, and The Slow-Cooker Savant (and cookbook number two on the schedule for 2025!).  I am also available for speaking engagements, webinars/CLEs, coaching, training, and consulting.

Connect with me on Twitter @10ThingsLegal and on LinkedIn where I post articles and stories of interest to in-house counsel frequently.  

“Ten Things” is not legal advice nor legal opinion and represents my views only.  It is intended to provide practical tips and references to the busy in-house practitioner and other readers.  If you have questions or comments, or ideas for a post, please contact me at sterling.miller@sbcglobal.net, or if you would like a CLE for your in-house legal team on this or any topic in the blog, contact me at smiller@hilgersgraben.com.

[1] But I will get to the mentoring post soon, as that feels like a good topic.

[2] Seriously, only the criminally insane check a bag anymore.  Here’s a partial list of bag-checkers: Jack the Ripper; John Wayne Gacy; Leatherface from “The Texas Chainsaw Massacre,” that one guy who keeps staring at you over in Row 23 (yeah, I’m looking at you buddy!); my cousin Gary; and a host of other real psychos.

[3] Sure, you can use the stuff the hotel provides.  And then you will be bald.