I am a senior exec, travel constantly - blew through the 100K mark in the first week of June this year - and actually keep my rollie underneath my bedside table when am at home, so this topic is close to my heart whether I like it or not.
- TripIt App.Sheer and utter genius. Just forward all the reservations to Tripit and it builds a step x step itinerary for you that is updated in real time. You will find that the airline has changed gates or cancelled the flight at least 10 minutes before the gate agent tells you; get in the rental, open the app, hit the hotel or meeting address and you are in maps and in your way...a game changer.
- Carry on only. Full stop. For me this means a rollie and a briefcase. Do not cheap out on either. I can go about 10 days. Recent long run was 9 days - home/Chicago/ Dublin/London/Paris/home - with this setup.
- One small bag for toiletries; one bag for the pile of charging accessories, both the same size. I use a hard case rollie from Halliburton, so when flying domestic I throw chargers in brief; toiletries in rollie because I have TSAPre. Overseas I just swap them when I have to deal with security.
Whenever you get home, just top up the kit bag with toothpaste etc. Less to think of when you are outbound next time.
- Merino wool tee shirts. Warm when they need to be, breathable when they need to be. Don't smell. Wool tee and a pair of smart wool socks and a pair of shorts covers the gym needs
- Earphones. Bose noise cancelers for the plane - this is a mandatory! The ambient hum of the road will really wear you out, to say nothing of screaming kids. I also carry a pair of B&O A8s for gym use. Yes the Bose rigs seem spendy at the store; 6 flights later they seem like the cheapest thing you've ever bought. Trust me here.
- Electronics: Macbook, iPhone 6+ (for reading the 100+ emails that hit me when I land), iPhone bayonet case with extra battery, iPad with books, movies, etc., small iPod for inflight and gym. Chargers and cables for everything, plus a power block and some international adaptors. Also get one of those adjustable phone clips that attaches to the dash vents - key for navigating while driving. Make sure you have at least two wall plugs, preferably with multiple USBs, and I even have a small multi-socket wall plug that has three outlets - charging is an ongoing battle and when you whip out that socket in an airport and let two other folks plug in, you'll know what a hero feel like...
Special callout is a Plantronics Traveler bluetooth headset with charging carrying case - - this thing lasts forever on a single charge and has noise canceling..instant boardroom hush!
I also got a nice leather envelope/sleeve for my Mac. It serves as extra padding in the brief while traveling, but if I have a meeting where I don't need the whole rig, I can carry it like a portfolio.
- Stretch jeans. I have a bunch made by Alberto of Germany - they look like wool but stretch like sweats - and are key for flying long hauls. Get em in grey (light and dark) and they can rock a sports coat or a polo for either biz casual or off duty bar action. I have also gotten off planes and rocked right into a meeting with them and no one even notices - just look like gray slacks with the SC and the loafers. I crease em when I get them cleaned so they present as a bit more formal, but they simply cannot be wrinkled and have a big temperature range for comfort.
- Wool OTC socks. Again, don't smell, can deal with lots of temps, OTC doesn't cut off blood flow in calves leading to DVTs when flying.
- Biz dress: I have worked out a system where it is usually one suit, an SC, 1 pair of slacks and above jeans. Shirts are the toughest as they are space takers, but this format lets you swap from day to day without looking the same. Wear the SC on the plane, suit the next day, then SC etc. Pack suit and shirts in thin laundry plastic sheets from the cleaners and you rarely have to bother with ironing.
- Off Duty: you can usually go with what you were wearing sans the tie these days, but I always throw in a black or navy polo just in case. If you have room, a pair of dark suede drivers are nice to have. I also use Kent Wang's long sleeve rugby's quite a bit as the collar and button cuff work well alone or with the SC.
- Shoes: Wear loafers; carry lace ups or monks, get a pair of thin-soled Nike or whatever trainers that collapse down to nothing. Light cedar trees with metal flex shafts for whatever is not in use. I almost always wear suede shoes - no polishing! - and can be brushed out quickly at the end of the day.
- Light cashmere sweater or cheap-o down vest. Both roll up into nothing and provide an extra measure on a plane (esp overnight flights) or underneath your jacket when it gets chilly.
- Eyeshade and inflatable pillow. The fold down to nothing and stay in the briefcase. Put em on, pop on those Boses and you can actually sleep! Get a pillow that has a self-sealing valve or they will leak.
- Those little mesh pockets in the rollie: Spare Central! Collar stays, cufflinks, suede brush, pocket square, handi wipes, plastic shoe horn, aspirin, bandaids, needle and thread, etc. - the stuff you will eventually be looking for at some point when everything is closed and you only pack it once.
- AMEX Platinum card. Yes initial cost looks steep, but within 20 minutes on the phone with their concierge, you can zero out the expense if you are smart. TSAPre or Global entry fee? They'll pay for that. Better boarding if linked to an airline. Upgrades all around but the real key is Club access - you are going to be dealing with "dwell time" (i.e. being trapped in airports) and the quiet of a club alone is worth it, to say nothing of the free drinks and the dedicated agents in case you need help. Bring a colleague and the day charge gets wiped clean. It also includes a "Priority Pass" membership that gets you into every airline club around the globe for free as well (except UAL, but if you are flying United, that is the least of your problems).
- ID and cash: I carry my passports, security credentials, and about $200 across 3-4 local currencies where we have offices in an old Rolex document case in my brief. Keeps it central and you don'l have to sweat it on small charges when you land somewhere at 11Pm on a Sunday night and the forex kiosk is closed.
- Early boarding access:This is key. Every - and I repeat - every flight is oversold by about 20 seats these days. That means overhead space is premium real estate. I have painfully elite status so not an issue, but get an airline card until you do so you can get on with or ahead of Group One.
- Wherever possible, reduce your "drag coefficient." I cannot stress this enough. This means that you need to smooth out all the "little things" like faster security (TSA/Global Access/etc.), no checked baggage, status with a car company so you just walk out and drive away, airline club access, priority boarding, sitting front on the plane, etc. etc. This may not sound like much but it makes a HUGE difference over time if this is your life as those are minutes and aggravations you cannot get back or avoid. If you are a road warrior, that all add up..quickly.
And.. the first time you come back from overseas and walk past the hundreds in line for immigration, roll up to that kiosk, and get waived through in less than 5 minutes from end to end, the pain in the ass navigation of the government website that it took to get that Global Pass seems like a gift.
- Finally, dress up a bit and be nice to the help. The amount of abuse airline and security folks take is staggering, so when a well-presented soul arrives, smiles, is pleasant, and thanks them for their help several times, it can be a game changer. Remember, policies abound, but the Gate Agent has all the power in the world when it comes between wherever you are and wherever it is you are trying to get!
Hope this helps...