Airfare Analysis Paralysis

I don’t know if anyone else suffers from Airfare Analysis Paralysis, a particularly insidious form of analysis paralysis, but I do. Booking flights is usually an over-constrained problem for most. With family obligations, work obligations, and a general low tolerance for airports and layovers, I assume that most people find something in their price range that is generally tolerable and purchase, not looking back.

I do not. I have been fortunate to be able to structure my life and most of my business dealings such that, with some time zone contortionism and green-screen magic, I can be in my office in Seoul from anywhere in the world. This is more practice than anything else. What this means is that the single most limiting constraint in travel for me is unusually flexible: time. When time is not a constraining factor, the same general fare class across even a single airline alliance opens up a paralyzing number of possibilities. I encounter this every single time I book a flight.

Part of this comes from my absolute love affair with the traveling experience. I really should go find an opportunity to help design travel experiences for airlines and airports. I relish every aspect of travel. This may have something to do with the absolutely ridiculous number of international flights I have taken over my relatively short life time.

I love traveling. I love airports, I love flying. I love airport lounges. I love wandering through the terminals and watching people from all across the world. I love listening to dozens of languages being spoken. I even generally don’t mind trans-pacific economy, with the caveats that once you fly business, it is hard to go back, and it’s better to schedule your flights outside of peak times so that you have two, three, or sometimes even four seats to yourself.

With so many long haul trans-oceanic flights under my belt, with my origin and destinations not traditionally in hub cities for the same airline, I have learned a few things about luggage, routing, and magic.

Magical Lessons about Long-Haul Flight

Photo by Mantas Hesthaven on UnsplashPhoto by Mantas Hesthaven on Unsplash

First, if you don’t check luggage, you can re-route yourself as much as you want.

I once had a flight that was delayed out of SFO to ICN because of weather. The counter was less than helpful, so I called the United service center and told them that I was standing in front of a less-than-full flight to Hong Kong which was nearly done boarding. They hem-hawed over whether or not I should be allowed to board and take a red-eye from HKG to ICN. Then I uttered the magic words, “I have no checked luggage.”

“Oh. Please go to the gate right now, then.”

“I’m already taking the escalator down.”

It was magic, and I got to spend a few hours in a sleeping room at the Premium Lounge in HKG.

Second, while layovers in particular cities aren’t guaranteed in the event of equipment or weather issues, most of the time you are safe to assume that you will get the layover that you expected when booking your flight.

This means that you can intentionally experience new food, new languages, new cities, and to bring a piece of that place with you.

It’s always wonderful to show up to a destination with unexpected gifts for someone. Candy, trinkets, something off the beaten path, food that someone has never tried before ç within the limits of what customs allows ¸let you share the experience with others.

Not everyone enjoys my routing philosophy. I once decided to use miles to book a flight for a friend. The intended route was meant to be around the world. Incheon to Abu Dhabi to Rome to London to New York to San Francisco to Seattle, there to stay, and then back to Incheon. Rerouting caused the final route to be Incheon to Rome to London, with a 23 hour layover in London. The flight to New York returned to London after being in the air for two hours because of an engine emergency, and was rerouted after another 12 hours — all spent in the lounge — to Dallas, continuing on to San Francisco and then Seattle.

Photo by Amir Hanna on UnsplashPhoto by Amir Hanna on Unsplash

All of the boarding passes were marked SSSS, which either stands for Special Secondary Security Screening or Super Secret Scrotum Search — still not sure which. After being, swabbed, probed, and violated at every boarding, completely jet-lagged, my friend arrived and informed me in no uncertain terms that I would never ever be allowed to book flights to him again. Ever.

That said, he did go around the world once. (I’ve encouraged him to go back the other way because now he’s wound up once and needs to unwind.)

The Problem

With the most limiting constraints gone, the possibilities are endless, as my friend learned. I just spent two weeks trying to figure out how I was going to get from Seoul to San Francisco. Trivial for most, given that I sold my soul to United and that they offer a direct flight.

Trivial for most. Paralyzing for me. Was I going to fly out of Kimpo Airport or Incheon? Even with the Wuhan Pneumonia taking China transfers off of my list — a 10 year Chinese visa really doesn’t help with this constraint satisfaction problem — I still had far too many options for layovers:

  • Was I going to have an 8 hour layover in Osaka and visit some old friends?

  • Was I going to have a 4 hour layover in Singapore so I could experience Changi Airport for the first time ever?

  • Was I going to have a 7 hour layover in Honolulu? I’ve never been!

  • Was I going to have an 18 hour layover in Tokyo, and if so, would it be through Haneda Airport or Narita Airport?

Photo of Changi Airport by timJ on UnsplashPhoto of Changi Airport by timJ on Unsplash

Ultimately, as the date of my departure grew nearer and nearer, good options disappeared and I had to settle for five hours at Narita. Not really long enough to comfortably get into Tokyo, do anything, and get back to the airport without a rush. Just enough time to peruse the bookstores, eat something good, and stretch out in the lounge.

The Solution

I’ve decided that I need ground rules. If I keep them to myself, I will forget. If I display them publicly then my friends will remind me the next time they are waiting impatiently for me to share my arrival details. Here are the rules of which my friends will now remind me when they are watching me add unnecessary agony to my life.

  1. Choose ONE experience. This experience can be visiting a new airport, leaving an airport to visit a new country and collect the entry stamp — although these are becoming less and less common, trying a new restaurant, or catching up with an old friend.

  2. Commit to a flight within ONE hour of starting the search. It’s really diminishing returns at a certain point. One hour seems to be the sweet spot to prevent yourself from wasting hours looking at the infinite possibilities and being distracted from the ONE experience you are going to have.

  3. Within the free cancellation window, feel free to try to outdo yourself. This is where you grant yourself permission to explore the possibilities. Most airlines allow you 24 hours or so to cancel your flight without a fee. If you want to optimize for a SECOND factor, this is the time to do it.

I messed up this time around by optimizing for time in Japan then then also trying to optimize for the possibility of potentially being offered the chance to buy an upgrade at check-in time. Ultimately, I went from a 16 hour layover in Haneda to a 5 hour layover in Narita.

At 16 hours at Haneda, you’ve just won yourself a day to explore Tokyo. At 5 hours in Narita, your prize is deciding whether the United Lounge is better than the ANA Lounge. (Spoilers: It’s not, but it’s still pretty good, and you can still take a shower.)


These rules aren’t for everyone. Not everyone handles jet-lag like a champ, and many people feel like this increases their travel agony. I’m fortunate in that I can handle a lot of travel abuse and still think of it as a fun, new adventure.

Even if these rules aren’t for you, perhaps you like hearing about travel, technology, programming, startups, and Korea. If that’s the case, you might like to follow me on Twitter.

This essay was originally posted on and reposted on Medium.

Lorenzo Swank
Entrepreneur in Residence and Venture Partner

Serial entrepreneur, computer scientist, and amateur eletronic violinist, currently working to level up my skills by collaborating with other entrepreneurs on early stage ventures.