How I Travel


Buck Woody (Blog@BuckWoody) tagged me in a blog post called How I Travel where he talks about how he packs, how he works on the road, and his journey logistics.  Paul Randal responded with the Paul and Kimberly Travel Guide, and those two are definitely hard-core travelers.  I think I’m probably the most amateur of that group.  I’ve blogged my Travel Tips for Non-Frequent Fliers, but here’s a few more thoughts.

My Travel History

I got started working in the hospitality business – hotels & restaurants – and worked my way up to hotel general manager, then to a hotel management company’s corporate office.  I traveled full time for a couple of years, and I do mean full time: I didn’t even have an apartment.

After I switched my career into IT, I met up with the love of my life, Erika.  She went to work for an airline, and airline jobs come with unbelievable travel benefits.  We flew all over the world for $10-$20 per flight, often first class.

These days, I prefer not to travel more than a week per month because Erika’s waiting back home for me here in Chicago.  Therefore, my travel routines look a little more rushed – take my Germany trip next week, all times local:

  • Saturday 6PM – leave Chicago on a flight
  • Sunday 10AM – arrive in Munich, try to get acclimated to time zone changes
  • Monday – present in Munich during the day, then grab dinner and catch a flight to Cologne.  Get to hotel at 9pm.
  • Tuesday – present in Cologne, then grab dinner and catch a flight to Berlin.  Get to hotel at 9pm.
  • Wednesday – present in Berlin, then grab dinner and catch a flight to Vienna.  Get to hotel at 9pm.
  • Thursday – present in Vienna, thankfully get one night without travel.
  • Friday 9AM – leave Vienna, stop in Dusseldorf
  • Friday 11AM – thanks to the magic of jumping time zones, arrive back home in Chicago completely exhausted
Me in San Francisco
Me in San Francisco

This kind of travel isn’t fun at all – it’s tiring even when everything goes flawlessly.  Unfortunately, it never goes flawlessly, and some of my travel highlights include losing my ATM card in Mexico, getting food poisoning in Paris, crashing a laptop in Sweden, getting all my clothes soaking wet in London, and on and on.  I try to prepare as much as I can to lessen the pain.

How I Plan My Trips

I try to avoid layovers when I’m planning my flights.  Every time you change planes, you increase the chances that bad things will happen; your bags might not make the switch, weather might pop up in that middle airport, or delays might cause you to miss your connection.  Employers these days have policies about taking the cheapest flight no matter what, without regard to flight cost, but I can usually work around that.  I write something like, “The nonstop flight is $150 more than the cheapest one with a layover, but it’s worth the gamble here because I’ve got an event to attend first thing in the morning.  I can’t afford to get delayed by a missed connection – we’ll miss the entire event.”

I stick with my main airline or its partners as often as possible because airlines treat frequent fliers better.  When you’re elite, your bag is among the first ones off the plane, you get preferential treatment during boarding, and you can get bumped up a class if there’s space available.  To learn more about how the reward game works, check out FlyerTalk, a forum site loaded with tips on how to get to elite levels fast.  If you’re on the cusp of hitting elite, but you won’t make it before the year ends, read their mileage run forum.  Readers post cheap, long flights that rack up lots of miles for very little cost, thereby ensuring you make elite.

My favorite airline isn’t always the one with the cheapest rate, so I’ve been known to tweak my arrival/departure dates & times in order to make my airline the cheapest choice.  If I’m doing a conference from Tuesday to Friday, and my airline isn’t the cheapest choice for a Monday night and Friday night flight, I’ll switch to Monday morning or Saturday morning flights to see if that makes a difference.  I prefer early morning departures because weather hasn’t mucked up the day’s flight schedule yet.

I don’t usually have much of a choice when it comes to my hotels or car rentals – that’s dictated by my employer – but sign up for the frequent flier rewards on those no matter what.  They rack up much faster than you’d expect.

How I Pack

I look at my itinerary and try to narrow down my schedule to one pair of shoes.  If I have to wear a blue Quest shirt for a particular event, I’ll try to coordinate the rest of my outfits on that trip to match, thereby letting me survive with just brown shoes.  If I have to wear a black PASS shirt, same idea – set up all my clothes so I can just wear black shoes.  This one decision determines whether I can do the trip with a carryon bag or if I have to check my luggage.  If my flights involve a layover and I have to check my bags, then I’ll bring a carryon too, because I don’t want to worry about arriving without my bags.

Buy good luggage – not expensive luggage, just good luggage.  The stuff you find at big-box discount stores isn’t made well and falls apart after a few trips.  Check out FlyerTalk’s travel products forum for mind-boggling discussions of the lightest bags and how to pack them.  For example, here’s how to pack a suit jacket into a carryon without wrinkling it too badly – a trick I’ve used on transatlantic flights:

Inside my checked bag, I put instructions in big print on where to send the bag if it gets lost.  I print them out on an 8×11 sheet of paper and set them on top of all the clothes, saying, “IF THIS LUGGAGE IS FOUND, PLEASE SEND TO…” and list my home address.  I don’t bother with my trip itinerary – I don’t have good luck with luggage catching up to me on a multi-city trip.

How I Work on the Road

I tried carrying just my iPad to TechEd this year, and that was a failure. Almost as soon as I got into the airport, I got a T-SQL question from the guys at StackOverflow, and I would have been able to solve it immediately if I’d had SQL Server with me. Several times during the week, I said to myself, “Dammit, this would be so much easier if I had this one file.” There’s solutions to put all your files in the cloud, but TechEd attendees will recall that the cloud failed us more than a few times during the week too.

SQL Server Cooks in Germany
SQL Server Cooks in Germany

There’s a few iPhone and iPad apps that make travel a lot easier:

  • 1Password – syncs with the Mac 1Password app, so I’ve always got my passwords on the go. Great for security – generates extremely strong passwords for each web site. Not cheap, but makes security really easy.
  • GoodReader – excellent document viewer with built-in library. I put my PDF ebooks in here for reference, but I don’t usually read from this when I’m on the road. I prefer reading magazines until the plane hits 10,000 feet, at which point I switch to working or playing games.
  • RememberTheMilk (free) – companion to, which stores all my tasks in one place.
  • Shanghai Mahjong ($.99) – iPad/iPhone game. I seem to have a new favorite game every few months.
  • TripIt (free) – companion to, which stores all my travel plans in one place. Just forward your confirmation emails to them, and they parse out all of the details.
  • Yelp (free) – business directory with reviews. Restaurants conveniently located near tourists are almost always horrendous. They don’t have to be good, because they don’t have to win your business twice. They just have to get you in the door once, and then repeat that over and over with thousands of tourists. Avoid ’em with Yelp.

How I Travel

Once I hit the road, I’ve got a binary philosophy; either things matter, or they don’t.

Sounds stupid, right?  Bear with me.

When I’m hungry, I either want to just eat, or I want to have an experience.  There’s nothing in between.  If I’m in a hotel on the road, getting ready to do a day-long seminar, I’ll eat breakfast at the most convenient location.  I don’t care what’s on the menu, I don’t care how bad the service is, and I’m not concerned with the ambiance.  My goal is to get fed, and to be the most pleasant human being possible during that transaction.  Someone else is taking care of me, and I want to show my appreciation for them making my life easier.  They didn’t aspire to work in the food service industry at an airport hotel, and a few moments of kindness will make their lives better.

When I’ve got the time and I want an experience, then I put effort into planning things out.  I open up the Yelp app on my iPhone, check reviews for local (not chain) restaurants, and do some comparison shopping.  I learn what the restaurant specializes in before I arrive, and I know what menu items to avoid.  I go in with wide eyes, take my time, and savor what I’m experiencing.

I approach everything in travel with that same binary mentality.  Pick your battles – not every experience on the road can be eating at WD-50 or taking pictures of the Eiffel Tower.

The most important thing, though, is to take care of yourself.  When you’re traveling for fun, sure, you can abuse yourself by staying out late every night, drinking the bar out of Jägermeister, and walking around mumbling during conference sessions.  When you’re doing this for a living and you have to present yourself in front of customers, then you have to get enough water, sleep, and downtime to project a good image.  It’s tempting to stay out with the gang and go crazy, and I’ll let myself have one night like that at the very end of a long trip, but do that every night, and you won’t get paid to travel for too long.

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