Traveling around the world has never been easier than it is now, but that doesn't stop people from complaining about it.

When someone gets back from a trip, the first thing you can expect them to talk about is some sort of problem they had in transit, more than likely with their flight.

Now, this could just be because problems usually make for good stories, and people like to have good stories, but it is nevertheless interesting that some people I know seem to have disastrous travel experiences while I usually have very benign problems.

Am I lucky? Am I just that good at travel? As with anything, it's probably some combination of the two.

Treat Travel Like Backgammon

A while back I did a post called What the Game of Backgammon Can Teach You About Life and Success, and it was pretty good if I do say so myself.

The article used the game of backgammon as an analogy for life because backgammon is rooted in chance (the roll of two dice), and yet it is possible to be good at the game (not just lucky). One becomes good at backgammon by understanding the odds of success when making certain moves and planning accordingly. By continually making moves that have the greatest odds of success, you will eventually succeed at the game, even if you get a few unlucky rolls.

Travel is no different, there are numerous travel decisions I will detail below that can potentially make or break your trip. It is important to realize, though, that even the most robust travel plans are still open to failure. All you can do is improve your odds, you can never guarantee success.

My tips are geared towards commercial air travel, but are applicable to other types of travel as well.

Stay Un-Connected

The first and perhaps most obvious piece of advice is to book flights with as few connections as possible.

It seems like most of the time when looking at sites like Kayak, there is always one flight that is direct to my destination and another that connects through somewhere else, and the one with a connection is a few hundred dollars cheaper.

In my youth, I would take the flight with the connection, but now in my old age I go for the direct flight. There are a few questions to ask yourself when making this decision:

1. How imperative is it that I arrive at my destination on time?
2. How much is my time worth to me?
3. How much does added stress cost me?

If the answer to the first question is "I need to be there on time", then choose the direct flight. If you have some flexibility, go to the second question.

Determining the value of your time is a tricky thing. It's fairly straightforward to calculate your hourly wage at your job, but when making travel plans people usually have to answer the question "what is my free time worth to me?" I dealt with this a little bit in my Real Men Change Their Own Oil article, and the bottom line is that it varies with the individual.

Here's a good rule of thumb to follow: your free time is worth $100 an hour.

For most people, that's significantly more than the hourly wage at their job, but I think one should prioritize their free time and not let it slip away. We only have so long on this earth, better to not spend it waiting on planes.You can use this number in making decisions and adjust it as you see fit.

Because I'm a math nerd and like easy-to-see formulas, here's a formula to help decide if you should make a connection or not (from a purely cost standpoint):

Where and are the costs of the first and second flight, and and are the trip times in hours (including connections) of the first and second flight. The factor of 100 counts for the "cost" of your time.

If the cost difference, , is negative, then it is "cheaper" to go on flight 1, and if it is positive, then flight 2 is "cheaper".

Now, to the third question: how much does added stress "cost" you?

This is another difficult thing to quantify, but one can make the argument that the more destructive stress you introduce into your life, the less productive and less happy you will be. By "destructive" stress, I mean stress that does not really help you in any real way. Things like working out or playing a sport would be considered constructive stress, because they can enrich your life. Other things, like waiting in traffic or missing a flight connection would be considered destructive stress, because they just make you angry and don't really help you in any quantifiable way.

The "cost" of these stressors will vary even more greatly with the individual. Some people can be introduced to all sorts of problems when traveling and just keep on going with a smile on their face. Others get incredibly stressed and anxious by the very idea that something could go wrong, The key is to assess how you react to travel-induced stress and plan accordingly. I would argue that even if you don't consider yourself "easily stressed", it would still behoove you to plan fewer connections, because even a little bit of induced stress can have a negative impact on your life.

Be Wary of "Discount" Airlines

Not all airlines are created equal, and some can be significantly less expensive than others. Now, I'm not going to tell you to not fly on a "discount" airline, but just be aware of what you are getting into.

Discount airlines aren't cheaper because they feel like doing mankind a favor, they are cheaper because they cut costs in places where other airlines don't, or charge extra where others don't. Spirit Airlines, perhaps the most notorious "discount" airline, has a few tricks up their sleeve. As this article points out, their fares seem like a steal until you factor in that they charge not only for checked bags, but also for carry on bags, among other things. Make sure you read all the fine print and know how to play the game.

In some ways, I like the philosophy of Spirit and other discount airlines, they basically have low base fares and then let you choose what you want to pay for. Other airlines may give you a bunch of stuff you don't want or need, but are paying for anyway. That said, if you actually do want all those other things, then it might be cheaper and easier to go for a more respected airline.

So if you are going on a short trip and don't need much in the way of luggage...and have a sense of adventure, then maybe give a discount airline a try. I've flown on several discount airlines in Europe and the experience was...mundane (the pilots did look a little young, though).

Understand the Potential Fragility of Your Trip

As an engineer, I love to optimize things. Travel, however, is a tricky thing to optimize, because there are many variables to consider.

If you have a trip with multiple connections, then determine which, if any, points in the chain could cause the whole thing to unravel if something went wrong. For example, if you have to catch a taxi to the airport and you have a flight that has multiple connections, then what would happen if the taxi is late? Do you have enough time to get to the airport and catch your first flight? If your first flight is delayed, could you still make your connection? If you miss the connection, is there another flight you could get on?

Now, the easy answer to this is "give yourself plenty of time." So, get to the airport at least 14 hours early and make the time between connecting flights at least 10 hours.

Obviously, there is a trade-off between time cushions and overall trip time: too little of a cushion and you open yourself up to missed connections and travel woes, too much cushion and you end up spending your entire life waiting around in airports.

To help with this, you can look up flight statistics on the Bureau of Transportation Statistics or flightstats.com and see how the airports you will be using fared.

A rule-of-thumb way to look at the issue is to analyze the causes of flight delays, with the main ones being maintenance problems and weather. The key to understanding maintenance problems lies in which flights are more profitable to airlines. Generally speaking, the longer the flight (i.e. the bigger the plane), the less of a chance there will be with maintenance issues. This is because longer flights (especially international ones) are the most profitable, so airlines usually make sure those planes are less likely to have any issues that could cause delays. Shorter domestic flights, especially to small airports, are much less profitable, so expect these planes to break down more often.

The other issue, weather, can also be predicted to some extent. Northern airports will have increased delays during the winter due to snowstorms. Southern airports will have increased delays in the summer due to thunderstorms. Some of the coastal California airports can also have fog issues, especially in the morning. Midwestern airports might have tornado issues in the Spring. One time I even heard of flights being diverted out of Phoenix because it was so hot that the aircraft's tires would melt upon landing. Know the potential problems that your airport can face in a given time of year.

Putting all this information together: if you're flying out of a small airport in a region that is known to get inclement weather during the time of year you are flying, then maybe add some cushion into your schedule. If you're flying on a popular route between two major airports during a temperate season, then you can maybe afford to live dangerously.

Learn to Deal With It

The things I've mentioned can help you to have less frequent travel woes, but the cold hard reality is that the more you travel, the more likely you are to have problems.

Problems are a given, but ways of dealing with them can vary. Some people live by the assumption that the louder and angrier you are, the more people will work to solve your problems. This way of doing things in not in my nature, as I am a generally soft spoken and easy-going person. The way I look at it, if you act like a big tool, then people do only as much as it takes to get you out of their hair. If you come across as nice and like-able, then they may be more inclined to solve your problem because they want to, not because they have to. Looking presentable helps with this as well (if you look like a lady or a gentleman, you'll be treated as one).

But, even if you've done everything "right", you will still run into travel woes eventually. Just understand that it's all part of the risk that is traveling and embrace the adventure. Something I learned when doing a study abroad in Europe is that the worst problems make for the best stories. No one wants to hear about how your trip went off without a hitch and everything was just fine, they want something with a plot!

While I was thankful that most of my trips around Europe were fairly uneventful at the time, I most enjoy talking about the one time when the train we wanted to take was cancelled due to a strike, and we were forced to take a trip with 5 connections in order to get from France to Italy. In the process, we spent the night in a small train station somewhere near the German Black Forest. Because I was in Germany and wanted to see if I could, I tried ordering a beer at 5 a.m. in a McDonald's at the train station and got yelled at (in German) by the cashier. The rest of the trip was quite nice.

So, the next time you have travel problems, just think: "this will make a great story one day."