In a bit over 20 years of business-related travel, most of it for one- or two-day engagements of the peroration-plus-consulting type, I have collected some ideas that have made travel less miserable.
These are ideas that work for me, derived from observation, planning, experimentation, and reflection, all in the context of what I do in these trips, which is talk to people about highly technical business topics, generally wearing business attire and usually including a presentation of some kind that requires last-minute edits and some data processing on-site. Yes, these details matter. Little of what's below applies to Jean-Michel Jarre going on tour.
Don't check bags. The site OneBag elaborates on this -- for tourists, mostly. As a business traveller for whom flexibility is important, I find that being able to carry all my stuff, fast and without having to negotiate ramps for wheeled trunks, is a great advantage.
After working through a large collection of rolling carry-ons and hanging garment bags, I've settled on a Victorinox trifold bag. Yes, the tri-fold may harm the suits if you're such a novice at packing that you don't know how to pack a suit for travel. But the small size and light weight, the large open space, and the backpack conversion (for when you have to lug it over miles, oh, say, in Heathrow airport, if you're ever so unlucky as to be forced to fly through it) are worth the small risk.
For some one-day trips, I take only a Brenthaven Urban backpack; its design and all-black look are professional enough to not clash with the clothes, and judicious choice of suit and chinos will allow the suit jacket to work as odd jacket (hung during the flight), while the suit pants & vest and the other clothes take up the rear compartment of the backpack. (Bundle packing is worth learning, if you travel much.)
If you need to get a large bag from place A to place B when you fly from place A to place B, say a lot of A/V equipment in a Pelican case, use a messenger service like UPS or FedEx. This doesn't work well internationally, but is a good alternative domestically.
Multitaskers are very important. Smart phones and high-end laptops are worth carrying; the Kindle, not so much. Because I do data analysis and the occasional data processing on the road, I have to carry a full fledged MacBookPro instead of a MacBookAir. I'm hoping for a new iPhone next week which will replace a gaggle of small electronics: phone, iPod Touch, voice recorder, GPS, camera, camcorder, and ebook reader.
The main point about multitaskers is not the particular choices I made, but an attitude of doing more while carrying less. For entertainment, I used to carry DVDs to watch; now I have movies on the computer. To work on downtime, I used to bring a stack of papers to read; now I bring them as PDFs. If in my office I'd print them to read off paper, but on the road I make my adjustments.
The quintessential multitasker, the Swiss Army Knife, of which I have several, is sadly no longer a staple in my travel, as the ridiculous "security" rules in place now preclude it.
For some critical tasks, you need the optimal tool, even if it is a unitasker. Neckties are unitaskers, in fact their task is just to be present, but they are a part of business attire and must be worn to many social functions. Presentation remote controls are unitaskers, but the difference between being at the podium operating the computer and doing the theater that is a live presentation makes it worth carrying some of these. (One? Are you kidding? Critical equipment requires backup.)
Backups are very important. Everything in the laptop is replicated in a portable hard drive, obviously, and all the critical materials are replicated again in several flash drives, each with a full set of copies. Everything important is also on the cloud -- encrypted, of course. But that's just the obvious backing up.
There are other things to backup: your flight, your hotel, your transportation. Having backup plans for these help. It doesn't mean having the reservations on several flights and hotels, but rather knowing available alternatives. There's a big difference between letting the front desk at the hotel try to help -- assuming that they try -- and having a list of hotels and their phone numbers ready.
Backing up your presentation doesn't mean just backing up the presentation materials. It may mean backing up the presentation strategy. My most important backup is a high-quality print of my handout, which can be photocopied just-in-time if all other materials fail. (I generally send the handout as a PDF early, so the client can make and distribute copies in advance. And I always try to get the contact of the point person whose job is to get these handouts made, distributed, etc. Of the times I don't get a point person contact, it's best to carry copies myself. Pays to make 1-page handouts.)
I always carry my prescription glasses, even though I never wear them, which makes them no-taskers. They back up my eyes' ability to hold contact lenses. If it's temporarily lost, I don't want to be blind. (Of course I carry extra contact lenses; but that's no use to me if for some reason I can't wear them.)
And entertainment or social commitment backups are also a good idea. If I was planning to spend a free afternoon hiking in the hills near my hotel, a list of nearby museums and rare music stores is a good thing to have in the event of rain. If my plans to exercise vigorously are cancelled by being tired from presenting, having a map of local parks and eateries is a good idea.
The main thing here is the attitude that there must be more than one alternative to everything important. It doesn't need to be planned -- though I've found out that planning and researching does help. With time and experience, I have built a personal library of ideas to serve as alternatives at the drop of a hat. Now I never need to watch TV in the hotel to pass the time. (I take a look at the news, especially if I find out via the web, feeds, and twitter that there's something interesting there.)
Always carry a notebook and pen. Ubiquitous capture, as they say in Getting Things Done. In my case, it's more a matter of remembering ideas, of quickly sketching out presentations, or doing some recreational math or drawing while on the move. Making notes helps me remember things (as Field Notes say, I'm not writing to remember it later, I'm writing to remember it now).
I've used Moleskines more than other options because I like the elastic close, the place-marking ribbon, and the back pocket. But I'm not a snob, and use various notebooks. Mostly I buy these from the museums I'm a member of, supporting the arts and differentiating my notebooks from those of other consultants.
I like fountain pens, but they are not practical for in-flight use. Even the Rotring Initial doesn't work well -- though it doesn't leak. I've used a variety of high-tech pens (including the Fisher space pen), but I found that carrying a nice Montblanc Starwalker Rollerball and a couple of Papermate ballpoints is best. The MB impresses upon people what good taste I have (it was a gift) and the others give me two additional colors to think with and they're essentially disposable (I won't care if a borrower never returns them).
Audiobooks turn wasted time into useful time. True in all situations, like walking or running, and certainly for waiting in line while the airlines mutate their customers from sheep to sardines. (Mintzberg's joke.) But in my case audiobooks make a significant difference in the travel experience. My eyes tire very easily when reading from an unstable surface; even watching a movie is difficult. (I wear very strong contact lenses.) So, instead of trying to work or read a paperback, I just listen to audiobooks. Audible has quite a large selection of both fiction and non-fiction, and I can easily go through my Platinum membership's two free books a month. In fact, I keep buying extra credits.
Of course podcasts are a cheap alternative, and sometimes a good way to get up-to-date on some specific areas. However, other than the WSJ Morning Read (which I get gratis as a Platinum member), most business-related podcasts are disastrously bad, and podcasts about strategy, innovation management, marketing, analytics, statistics, and business economics -- my interests -- are even worse. I do listen to many TWIT podcasts and several non-work related ones.
I find that I retain less of audiobooks than I do of books I process visually (ebooks or paper books). For scifi and other fiction that's not a problem, and for many non-work related books that's acceptable. For work-related books, or books that I really want to explore, I end up buying a visual copy in addition to the audio copy. (How about bundling the three options, publishers, ebook, book, and audio file, for a discount? Huh? Too advanced for you?)
As with client, so is locale and trip: a little research does a lot of good. Taking a look at a map and figuring out how your hotel, client, and airport relate to each other, figuring out the major thoroughfares, locating restaurants and convenience stores nearby, picking interesting locations to visit if there's downtime, the possibilities are endless.
Same with the trip: research the airports involved, if some are unfamiliar to you, and the amenities available at each; research the hotel and its amenities and the neighborhood. Weather is always good to know, and sometimes a quick question on internet forums catering to your personal interests may lead to interesting discoveries.
Travel vests are lifesavers. I used to wear tactical pants and tactical shirts to fly. This is a bad idea: you spend a lot of time at security emptying and refilling pockets. Two better alternatives are the fanny pack and the travel vest. With either you just put them on the conveyor belt without taking anything out of their pockets. I used to prefer fanny packs (worn in front), but some places have "no bag" rules, and some airlines want to count them as your personal piece of luggage, so travel vests won.
In my experience nothing beats a Scottevest travel vest; its pocket-in-pocket architecture allows me to keep things organized, its structure lets me carry a lot of weight with comfort, and its Personal Area Network is a great way to keep wires out of the way. I have several cargo vests, including two Scottevests, a Columbia, a Trail Designs, and a Paul & Shark, and I'm buying more Scottevests.
Avoid airline food, drink as much water as they'll give you, and carry multivitamins. Airline food is not as bad as it's made out to be, but just barely. If you want to eat airline food, ask for one of the alternative meals when you make the reservation. Alternative meals are usually handled more carefully and generally better prepared.
Depending on the arbitrariness of the day's security personnel, you may be able to bring outside food into the plane, say a sandwich from a good deli. I used to bring several protein bars and eat them in lieu of food. If all fails (the TSA page says you can bring food, but you might be made to miss your flight by the petty tyrants manning the x-ray machine if you argue that point with them), not eating for a few hours is not a big deal.
Water is important, though. Dehydration decreases your ability to speak clearly, your mood regulation, your cognitive abilities, and especially your brain executive function. Keep hydrated. I'm shameless in my quest for airborne water; you need to be, given how unfriendly the skies have become.
Multivitamins are important because on the road you may not have time to eat right, or to eat, outright. Vitamins are more necessary than other nutrients, so making sure they're available is important.
Plan your clothing, and I don't just mean the outfits. But do plan the outfits. In my case this is fairly easy as I travel with conservative color schemes for everything but ties and pocket squares. (What? Wear a tie without a pocket square? The horror!) Add backup underwear and shirts. You always end up needing one more than you thought.
Not wearing tactical pants for travel means you can wear chinos, which -- in a suit emergency or in some social situations -- can dress down a business outfit to a business casual outfit. Yes, there are many places where this matters. Chinos can then multitask as travel, walk-around, and business casual clothes. Sorry, 5.11 pants.
Black sneakers are not shoes. But, as a last resort, when your oxford shoes are dripping wet due to your inadvertently walking on the rain-filled potholes that your client's city calls sidewalks, they might work as part of a business casual ensemble. And you can exercise with black sneakers as well as with those with funny colors.
Exercise works out the kinks of travel. Even if the hotel doesn't have a health center (what kind of cheap-ass hotel doesn't have a health center of some kind or a swimming pool?), doing some calisthenics in your room or going for a run -- even an energetic walk -- helps get those lactic acid deposits out of the muscles. It also helps relax and re-oxygenate your body.