Frequent Traveller Nightmare Part 1: Why I don’t travel (that much)

I used to love to take a trip on an airplane. And my airline of choice was United. I flew on them because their planes were clean, they got me to where I wanted to go most of the time without a plane change (particularly when I lived in San Francisco), and I could follow all of the air traffic fun on my headset, giving me something the remote possibility of learning something, while mindlessly staring out the window.

Almost a decade ago my love affair with flying ended, sometime after the love affair with my (now) wife began. We were often separated by hours of overnight flights and thousands of miles. It was also a time when United went bankrupt while their planes were over capacity. Since then, the Towers fell on 9/11 (I was in the UK at the time), and we’ve become so paranoid about our personal safety thanks to the Bush Era approach of leading from a position of fear that air travel has become a flying prison experience. And so I have largely stopped.

My own personal travel has dropped from a peek of 120,000 miles per year down to roughly 30,000. Yes, I still travel, but considerably less, and not often to America. There are more than a few reasons for this:

Flying is expensive, especially for families. I now have one.
Fuel surcharges that can be over 200% of the cost of the ticket (something that Continental misleads customers to believe it is entirely beyond their control).
Distance- this cuts both ways: I don’t need a plane (or even clothing) to see my wife and daughter, while my parents and American friends are much farther away, making the trip both more expensive and difficult.
Convenience- who wants to deal with the TSA? To be fair, here in Switzerland they really do make it as painless as possible. I have only ever once missed a flight here in Switzerland, when a train broke down, and the SBB actually rebooked me on the next flight before I arrived at the airport!
A long flight is hard on a child– any child. Parents need to think long and hard before putting their children– and other passengers– through that. We made that mistake by bringing our daughter on a long haul at the age of 4 months. When she was sick. Big mistake. Even though the doctor told us it was okay for her to fly (he was wrong) in order to get to Florida.
But beyond that, anyone in the back of a long haul has a miserable experience ahead of them from the moment they board. You can be assured that drinks on American airlines won’t be free, the movies will be lousy, and the food will be, if anything, worse than you remember.
Families have very few options to upgrade. When I’ve done so, it hasn’t been worth it. After all, what’s a comfortable chair if you can’t sleep because you need to attend to a child?

All of this boils down to the fact that the average flight to the U.S. costs us around $3,100. It’s about 1/3 that to elsewhere within Europe. Compare that with the $388 it used to cost me to go from San Francisco to the East Coast.

This leaves business travel. I have reduced that as well. A lot. Some people aren’t in a position to do so, I am, and I have. It has helped that my company now discourages travel where four years ago people would just as soon hop an airplane than pick up a phone. Now we have TelePresence, WebEx, and all sorts of other collaboration tools at our disposal. I applaud the change.

But even when I do travel, within Europe I prefer the train when it is feasible. I recently chose the train over the plane to get from Zürich to Maastricht. That turned out to take only about an hour longer without a plane than it would have taken with. But it cost quite a bit more. Within Switzerland I always use the train to Geneva. No reservations required, and it just works.

A (Brief) Letter from Singapore

This week I find myself in one of the chief Asian powerhouses: Singapore. I visited this tiny but hugely influential country fifteen years ago, just after having read another Letter From Singapore in the New Yorker magazine. Back then, the community seemed smaller and the businesses were lots more cozier. Today, the community seems larger, and businesses are still pretty cozy.

Singapore is a nation state of paradoxes. Its small size would not lead one to believe that it is one of the chief trading centers in the region, with container ships constantly waiting to unload. That, by the way, really does seem to be one of the lone constants between now and 1993. The hotel I stayed in then, the Pan Pacific, was one of the taller buildings. Today it is in the shadow of many others.

The city itself is difficult to evaluate this week because of an extraordinary event. They are hosting their first Grand Prix on the weekend, which will be held on the streets at night. It’s a first for Formula 1 and somewhat controversial. What is not in dispute is that when F1 comes to town to do a street race, everything gets turned upside down. Tonight, returning from dinner, with many street closures in order to form the racing circuit, my taxi took me through the connected substructure of many buildings to get me back to the Mandarin Oriental. We needed a residence pass just to do that.

The hotel prices on Thursday night will increase from a seasonal norm of $300SGD to $1800SGD. This means I will be out of here on Thursday.

Singapore sports a cross of many cultures, including Chinese, Malaysian, Bengal Indian, Japanese, British, and yes, some Americans. This intersection leads to a wealth of cuisine entertainment and education options. There is a disparity amongst some of the groups, and to be sure, not everyone here is wealthy, but for a tourist it represents an interesting stop in the middle of the Pacific rim, with Indonesia, Malaysia, Thailand, Vietnam, and Hong Kong, not far off at all, and Australia, an almost reasonable distance.

The people here are extremely gracious and the service has been nothing short of remarkable. More on Singapore in a future note.

How Much Do You Value Privacy?

People in my company travel a lot, and they like to have their itineraries easily accessible. My wife wants to know when and where I will be, and that’s not at all unreasonable. So, how best to process and share that information? There are now several services that attempt to help you manage it. One of those services, TripIt.Com, will take an email message as input, organize your itinerary, generate appropriate calendar events, and share that information with those you authorize.

The service is based in the U.S., and might actually share information with those you do not authorize, to market something to you- or worse. If the information is stolen, as was the case with travel information from a hotel we discussed recently, it can be resold to burglars who know when you’re way. That can be particularly nasty if in fact only you are away, and the rest of your family is not.

But before we panic and refuse to let any of this information out, one should ask just how secure that information is. As it happens, travel itineraries are some of the least secure pieces of information you can possibly have. All a thief really needs is an old ticket stub that has one’s frequent flyer number, and we’re off to the races. In one case, it was shown that with this information a thief could even book a ticket for someone else.

So how, then, do we evaluate the risk of using a service like TripIt? First of all, TripIt does not use any form of encryption or certificate trust chain to verify their identity. That means that all of your itinerary details go over the network in the clear. But as it turns out, you’ve probably already transmitted all of your details in the clear to them by sending the itinerary in email. Having had a quick look at their mail servers, they do not in fact verify their server identities through the use of STARTTLS, not that you as a user can easily determine this in advance.

Some people might have stopped now, but others have more tolerance for risk.

Perhaps a bigger problem with TripIt is that neither its password change page nor its login page make use of SSL. That means that when enter your your password, the text of that password goes over the network in the clear, for all to see. It also means that you cannot be sure that the server on the other end is actually that of TripIt. To me this is a remarkable oversight.

For all of these concerns, you still get the ability to generate an iCal calendar subscription as well as the ability to share all of this information with friends and family. Is it worth it? One answer is that it depends on whether you actually want to enter the information yourself, whether you care about security concerns, and whether you like using calendaring clients. It also depends on what other services are available.

Another service that is available is Dopplr. It also attempts to be a social networking site, not unlike Linked In. Dopplr allows you to share you itineraries with other people, tells you about their upcoming trips (if they’re sharing with you), and it lets you create an iCal subscription.

Dopplr also has some security problems, in that they do not use SSL to protect your password. They also do not use SSL for their main pages. They do, however, support OpenId, an attempt to do away with site passwords entirely. I’ll say more about OpenId in the future, but for now I’ll state simply that just because something is new does not make it better. It may be better or worse.

And so there you have it. Two services, both with very similar offerings, and both with almost the same privacy risks. One of them, by the way, could distinguish themselves by improving their privacy offering. That would certainly win more of my business.