Business Travel as a Lifestyle: A Practical Guide to Integrating Travel into a Busy and Stressful Life

I’m twenty years into my career and have been traveling for almost all of it. I don’t know the number of miles that I have racked up but it’s more than a few million. This piece is a practical guide to what I have learned as a “regular” business traveler (anyone traveling more than call it 75K miles per year) about everything from attitude to useful knowledge to stuff that will help make this way of life less stressful and more predictable.

Business travel is a tough one. Many of my friends have found fruitful and rewarding careers and have been able to limit it. I am now into my third career (first consulting, then venture capital and now CEO of a tech company), and I have never been able to avoid the need to be in the field. It’s challenging on family life, but I find it fulfilling to be out where the battle is being fought. After a life of being on the move, business travel is for me what feels ‘normal.’ But that doesn’t make it easy.

In general, I try to build the logistics and travel piece of business trips into a routine so that I can make the impact to the rest of my life as minimal as possible. The goal here is to minimize unpredictability, reduce the wear and tear on your body and maximize your ability to “be present” when you get home. I also find that my life has become increasingly more about managing energy than it is about managing time.

So, here goes.

Develop a Pre-Departure Routine — I keep a checklist in my closet that includes both stuff that I might need or want and also a few pre-departure to-dos. You’ll notice that airline pilots have so many tasks to do that they always rely on a check-list. Do the same and accept that there is too much going on here for your memory alone to deliver consistently.

Eating — It’s really difficult, and requires a lot of discipline, to eat well, while on the road. Fresh food is hard to come by and there’s massive abundance of high sugar food everywhere. I carry Luna Protein bars for when I don’t have other food handy. Kind bars are expensive but highly available in the airports these days. Evelyn Tribole’s Eating on the Run was introduced to me by the Mayo Clinic and is also a good place to start.

Always Carry-On When Possible — Airlines lose bags and some airports can really take a long time to unload bags (wildly high variance here from airport to airport). JFK is awful whereas Denver and Minneapolis are pros. I try as much as possible to not check bags. I have three different bags depending upon how long the trip is:

  • Patagonia Maximum Legal Carry-On — For trips of 1 to 2 nights where I am not wearing formal clothing. I can throw in a garment sleeve for pressed dress shirts. The Patagonia bag also has a sleeve for laptops for the minimalist.
  • Tumi Trifold Garment Bag — For trips of 1 to 2 nights where I am wearing formal clothing (i.e., suits).
  • Briggs & Riley Expandable Small Wheeled Suitcase — For trips of 3 nights plus — I have had mine for ten years and it’s a simple “pull from behind.” The new ones have four wheels, which can make it easier as you are rolling down the aisle on the plane. (by the way, does anyone beyond a flight attendant know what a roller board is?)

When you are putting pressed shirts or clothes together in a garment bag, separate them with plastic bags (the ones you get from the dry cleaner) and they will stay free from wrinkles.

In addition to where I store my clothes, I also have a separate bag for my computer, etc. Keep a second bag (backpack) with a second version of pretty much everything. I have two different backpacks, separate from my normal work bag that I use when at home, depending upon the trip length that I alternate between. I have moved away from brief case style bags to backpacks for posture reasons. I alternate between:

  • Tumi Backpack — It works well for long trips or ones that I need to be a bit more formal. It’s expensive but it’s worth it. Wait for that once/year sale at the luggage store. You’ll use it for forever.
  • STM Drifter Energy — This is a newer bag that I love made by an Australian company. It’s more casual but everything about it is awesome. It has a battery integrated into it to charge your tablet or phone. Most of the pouches are on the outside, which makes everything accessible. It also has a low profile design that fits under the seat in front of you on the plane, a surprisingly useful rain cover and a strap for attaching it to your wheeled luggage.

Buying an extra bag (with a second version of everything as I advocate below) sounds expensive. I’ve found that I spend the money buying things that I forget so this is really not a significant extra financial burden. And it reduces stress in a major way by lowering the likelihood that I need to make an unplanned trip to go find X (pick your needed thing) in a town that I don’t know well.

Getting Around by Car — I don’t particularly love driving though in the American culture we are accustomed to the automobile being the primary means of ground transportation. I use to default to renting a car except when I was in New York. Now I default to not renting a car pretty much everywhere I travel. Download both Uber and Lyft. When you add in trains, light rail, ride sharing and traditional taxis, the trip can be just as cheap as renting a car or close enough. More importantly, it removes having to deal with renting the car and figuring out how to get some place on time in a town I don’t know well. It reduces a lot of stress and focuses my energy on work.

Travel Expenses — I am an entrepreneur running a company that has been largely self funded. Travel is a big line item for our business. I encourage all of our employees to travel like they would if they were traveling on their own, and, as a result, we take a lot of indirect flights to keep the costs down. We have unlimited wi-fi passes as a benefit as a trade-off (there is a GoGo pass that works on all airlines). That way our employees can get a lot done while saving money for the company. There is a point where it doesn’t make sense to cut corners to be cheap but we try to promote an ownership culture in our company where we treat the company’s bank account like our own and there are some worthwhile investments — like unlimited GoGo — that can make this more manageable.

Keep a List of Regular Take Along Items — To my mind, one of the key goals in business travel beyond the obvious objectives of the trip is to increase predictability and reduce stress. I just turned 40 and I can tell you with some hindsight that adds up after a while. Showing up in a city that you aren’t familiar with and discovering that you are missing your shaver or computer power supply creates stress. See below for my list.

Mindset — The job of getting from point A to point B is an optimization problem. Don’t expect perfect service. I find it useful to be in the mindset that the goal is to get from one place to the other while expending as little emotional energy as possible. The transportation companies that serve you while you are traveling aren’t in the business of service, so don’t expect it, and realize that getting mad at the check in agent will only get your bags “accidentally” sent to Alaska. This is especially difficult for senior business leaders and entrepreneurs, who have a high locus of control and are use to people saying “how high?” when they say “jump.” It’s also compounded by unionized flight attendants who sometimes take it a little too far when it comes to their right to command passengers — sometimes they think they are the boss of you — and, unfortunately, they are. You’re not in control. You can restore your usual “going to kick ass” attitude the second you leave the airport.

Security — TSA, or what some affectionately refer to as “Thousands Standing Around,” isn’t in the business of making it a pleasant experience for you. Getting through security can be long and varies highly from airport-to-airport, season-to-season and day-to-day. Always plan to be there at least an hour in advance in airports you don’t know. Also, invest in the TSA Pre or Global Entry pass (at my company we volunteer to pay for it for our employees who travel regularly) so that you can use the TSA Precheck expedited screening line. Even when you are enrolled in one of those two programs, it doesn’t guarantee that you will be able to access it every time, so I wouldn’t rely on it as a time saver. I view it as a stress reducer that allows you to maintain your energy. Remember to log into your frequent flyer account for the airline you are traveling on to update your profile with the Known Traveler Number so that TSA Precheck shows up on your ticket when you fly with that airline.

A Note on Being a “Pro” — I frequently hear people bragging up their loyalty status. Don’t be that guy/gal. Use it for its advantages but don’t make an identity out of it. It’s of fleeting and limited value. Sure, the first six months will make you feel like a super awesome jetsetter. But that will disappear — the benefit of travel is being in the field to see how the product your company sells is being used by customers, or making the sale, or being with the customer — those things are of lasting value. Being away from your family so that you can earn a little badge, get on the plane first and maybe sit first class is a distant consolation prize for not seeing your kids grow up. Do append your loyalty status to your bags — not for bragging rights — because you would be amazed at how often that has gotten me out of a jam when I am stuck in a long line thinking that I am going to miss my flight.

A Note on Family Life for the Regular Business Traveler — I grew up in the family of a workaholic and I probably am one myself. Business travel is all wrapped up in this and it’s hard to untangle it from that greater personality. I have slowly become aware of the added stress that it puts on my family life. I come back and am tired and am less patient with the kids than I would normally be. Awareness is the first step. Also, don’t expect the kids to drop everything when you call to check in. It becomes a very routine “Parent: Just checking in… Child… Hi dad, good to hear from you, goodbye.” Don’t be let down by it. One strategy that I have used is to be more specific in my check-in questions… “How was your spelling test today?” or “What kind of drills did they do in soccer?” If your partner or spouse can stomach setting up Skype or FaceTime, even better. Even then, it’s hard to keep dialogue going with kids under age 10 that don’t yet have a cell phone to text. I also try to use the travel time away to be really productive so that I can be more present at home. It’s a work in progress.

Go For More Than One — The reason to go on a trip is usually driven by one thing — an important sales call, meeting with a long time customer, working on site, etc. But there’s always a reason to be there for other things. Add on a few extra sales calls. Visit other customers that aren’t the reason you are making the trip. Meet an old colleague for drinks.

Exercise — I go for a run every day while traveling. Even if it’s only for ten minutes. It helps me sleep better when I am not in my home time zone and it’s a great way to see a place you are not use to and to see the parts of town that you wouldn’t normally go to.

Meeting Scheduling — When traveling more than two time zones (e.g., Europe) think about scheduling meetings as close to possible as to when you would do it in your home time zone. Jet lag does have a big impact on you energy level, sharpness, attentiveness, etc. I am a fan of working with it by scheduling sleep and meetings as close to what you are use to as possible.

Know the Passenger Bill of Rights — Print it out and read it so that if the $%# really hits the fan you know your rights. Reduce your likelihood of ever threatening someone with it by reading the section above called “Mindset.”

Here’s the list of stuff that can be found on every one of my trips:

  • Extra USB Chargeable Battery — I use the Jackery Giant+ 12,000 mAh portable charger that can charge a cell phone three times and an iPad mini once or twice.
  • VGA Monitor Adapter for my Macbook
  • 2 Pens
  • 2 Apple Lightning Cables
  • 1 USB Electrical Adapter (if you are a Mac user, check out Twelve South PlugBug)
  • 1 Micro-USB Cable
  • Bose Noise Canceling Headphones
  • iPad
  • Two Books (or Kindle or Kindle App for iPad) — Can’t read more than two. Sometimes I am not in the mood for the one that I have.
  • Airborne — I take it in the winter and it really helps diminish the impact from colds or the likelihood that I get one. Lump the annual flu shot there as well as a precautionary meassure.
  • Water Bottle
  • Computer Power Supply — Have a second version from what you normally use and leave it in the travel bag.
  • Travel Shaver (I have a little Norelco that charges through a Micro-USB cable)
  • Travel Sundries and Meds — Again, I have a huge bias towards carrying everything on the plane. Skip the fancy toiletry bag unless you are checking bags and just perpetually keep them in a plastic bag that meets TSA’s requirements. HumanGear GoToobs are awesome for shampoo — under 3 ounces to meet TSA requirements.
  • Jabra SPEAK 510 rechargeable bluetooth speakerphone for calls in the hotel room.
  • Exercise clothes and running shoes and yurbuds running headphones stay in your ears (there are many running headphones out there). My Suunto Ambit 3 GPS running watch gets the GPS signal pretty fast when you are in a new city — my old one had to wait ten to fifteen minutes to get the GPS signals, which made it kind of useless for the quick jogs that you want to get in. I use the Wahoo Tickr heart rate strap with the Ambit.
  • Other Clothes — Use a checklist that you leave in your closet so you don’t miss stuff.
  • HooToo TripMate is a small wireless router that allows you to use multiple devices on wireless networks for which you purchase time (the HooToo is the device that connects to the network and your laptop, tablet and phone all connect to the HooToo). A little tricky to configure but a must have.
  • A memory stick if you are presenting a lot and you don’t know what the end set-up will be this can be a lifesaver.
  • Something to keep all this stuff together, such as a Cocoon Grid-It.

Alternative Stuff (Stored in Separate Drawer Where Everything Can Be Seen)

International Travel

  • Travel Adapter — I favor the Kensington 33117 as there aren’t multiple separate pieces that can be lost.
  • Power Strip to work with Travel Adapter — I like the Monster MP OTG400 — it’s small and has 4 adapters

Other Technology that Makes Travel Easier:

  • TripIt — This site/mobile app let’s you email the itinerary you get from the airline or travel agent to it and it adds it to your calendar. Also tracks flight changes.
  • Download the mobile apps for all of the airlines that you fly — I use 1password (another app) for tracking my passwords for these websites across my phone, tablet and laptop.
  • We use Concur for tracking travel expenses. The mobile app allows you to take a picture of the receipt — so you can pitch the receipt which you will probably lose anyway — and makes is much easier to submit expense reports when you get home.
  • Over the next few years the branded hotels are all moving to mobile check-in. Downloading their app will allow you to check in ahead of arrival, pick your room and bypass the front desk.
  • Evernote — I use it for note taking and can access it on every device, which is useful on the road.
  • Turboscan — I regularly need to sign legal agreements while on the road. This app allows me to snap a PDF on my iPhone and email it directly. Super easy.
  • Pocket — This web browser plug-in and mobile app allow you store away web content that you want to read while you are traveling. I also love the periodic emails that they send to you with other ideas for articles that are relevant to you. They are usually right on the money.

It’s also worth adding the WSJ’s The Middle Seat Blog to your feedly news reader to get the occasional travel industry update.

Note on Luggage: Patagonia, Tumi and Briggs & Riley have lifetime warranties. Travel luggage gets beaten up. It just does. Plan for it. Buy luggage from someone who will take care of fixing it (but don’t expect it to be fixed beautifully — just functionally). Tumi is the gold standard with a price tag that goes with it. Briggs & Riley is still expensive but a huge value purchase compared to Tumi. I have yet to have had to send a Tumi back in for repair but I have many times with Briggs & Riley and Patagonia and they have always taken care of it, even ten years after purchase.

I am always looking for additional tricks of the trade. Hit me back with any ideas you have at

Chris Smith is the CEO of Kipsu, a company that helps service businesses, such as hoteliers, retailers and healthcare providers, connect more deeply with their customers using text and other digital conversation channels.

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