Booking the Flight: Or, How Two Very Different Travelers Try to Get to Japan

I want to shift gears a little from my last few posts and talk about something lighter: actually, making travel arrangements. So far, I’ve been talking about some pretty heavy stuff — retirement, dreams, and the emotional weight of building a rich life — but I haven’t talked much about the travel part. Ironic, considering the title of my little corner of the interwebz.

Truth be told, this whole dream started with a travel idea. I’ve always wanted to go to Japan, but as a corn‑fed Ohio boy, it never felt like something that was in the cards for me, at least not until much later in life. Even then, my first attempt at going ended in a near‑total collapse of who I thought I was as a person. Fortunately, I have an amazing partner. Fresh off my return from Thailand, she suggested we plan a vacation to Japan later in the year.

That’s when things got out of hand.

When we started imagining our rich life, we pictured cozy corners, coffee, cultural immersion, and good public transportation. We imagined getting to know our neighbors, watching the sky and ocean dance their never‑ending tango across the horizon. We even planned for the emotional rollercoaster of buying our property, which, shockingly, went smoother than expected.

What we didn’t plan for was buying our first plane tickets to go see the house we had just purchased. Zillow has nothing on the adrenaline rush of buying an airline ticket to fly halfway across the planet, hoping the house you bought sight unseen isn’t a terrible idea.

And that’s where our first real obstacle appeared, and we both learned that we have very different approaches to travel planning.

Confessions of an Airplane Nerd

Aside from my love of all things Asian, I have another confession: I’m an airplane/airline junkie. Whenever air travel is involved, it becomes my personal mission to find the best route, with the best seats, at the best price, with the most miles, on the most interesting aircraft.

I’m reading travel blogs, airline websites, points forums, and compiling spreadsheets. I want to know the exact plane, the exact carrier, and whether I’ve flown that model before. I once routed myself through the Middle East just so I could say I circumnavigated the globe, and because it was cheaper than flying back across the Pacific.

But the real decision on that trip came down to this:

Do I fly an Airbus A380 over India at night, or a Boeing 787 during the day, so I can see India, the Indian Ocean, and the Middle East from the air? This is especially agonizing since I may or may not be able to ever come this way again!

These are the kinds of questions that keep me up at night!

On the one hand, the A380 is a piece of groundbreaking aviation history, and it will disappear from service in my lifetime. It’s not every day you get to fly on a four‑engine behemoth before it goes the way of the Boeing 707. On the other hand, it’s not every day you get to fly across Asia, the Indian Ocean, and see how it changes from the humid tropics of Southeast Asia to the arid deserts of the Middle East.

All this to say: I put a lot of time, effort, and energy into my air travel experiences. I will twist myself into a pretzel over minor details that appeal to my specific brand of nerdery. I know things about airplanes that would bore the average person to tears; things like fuel range, engine thrust, seat pitch, carrier rankings, and onboard amenities. If you’re getting irritated at me while reading this, describing my nerdery, then imagine how my partner feels when I start talking to her about it.

Meanwhile, My Partner Wants… the Exact Opposite

A little bit about my partner, she is the most down-to-earth, pragmatic person I know. Her own genetic profile is the apex of centuries of breeding that produced the perfect combination of German efficiency with the Protestant work ethic. That is to say, she has very specific air‑travel needs grounded in those two parts of her DNA. She wants a flight with:

•             the fewest connections possible

•             preferably direct

•             the earlier the flight, the better

•             efficiency above all else

For her, the shortest distance between two points is the only way to fly. Everything else is unnecessary chaos.

She also has ADHD and has never flown internationally. I know the level of chaos that exists at every customs gate on the planet, and I don’t want her brain to short‑circuit and decide this whole dream is stupid because the flights and getting through customs are stressful. So, we sat down with our separate devices to look at travel options. She is also the itinerary planner in the relationship, which is usually a godsend, but this time meant we were approaching Japan through two different angles and putting the process before the end result.

The Negotiation Begins

Trying to balance her need for simplicity with my need for aviation glory requires delicate diplomacy.

“How’s your search going?” I asked.

She looked up with a smile that said I love you and eyes that said I will stab you if you ruin my flow.

“Better than I expected,” she said. “I found a round‑trip package for around $1,000.”

Shit. That’s a good deal. My nerdy needs were not off to a strong start.

“Well, that is a good deal. Who’s the carrier?”

“I don’t know.”

“What do you mean, you don’t know?”

“Probably on the website. But it’s a nonstop flight from here to Narita, then on to Sapporo.”

That was it. My opening.

“Flying into Narita?”

“Yes.”

I fidget a little bit. I can tell she’s getting a little bit irritated, “Is that bad?”

“Well… all the blogs say flying into Narita is bad.”

“It can’t be that bad.”

“Bad enough that some carriers are even moving their flight operations out of Narita.”

“For $1,000, I think it’s worth it.”

Double shit. She’s not wrong.

“So… are we flying non-stop from Narita to Sapporo?”

“I don’t know. Why wouldn’t we?”

“Tokyo has two major airports. Flying into one might mean we have to deal with the other and figure out transportation between the two.”

“Oh.”

“Extra steps we don’t need with heavy luggage on our first trip. Are we getting any miles for this?”

“I don’t know.”

“Do we know where we’re sitting?”

She gave me the look again. “I suppose you have a better idea?”

I was in.

The Alternative Route

“Look,” I said, “maybe dealing with transportation between two airports and navigating customs at one of the busiest airports in the world isn’t ideal for your first international trip.”

She sighed, checked her tablet, and frowned. Externally, I remained stoic. Internally, I was peeing my pants. I had cracked the code.

“Okay,” she said. “You’re right. We’d land at Narita, then fly out of Haneda on our way to Sapporo.” She sighs, “Fine. What’s your idea?”

“For two hundred dollars more, we fly to Taipei, have a layover, then fly into Sapporo. Smaller airport, easier customs, no airport transfers, and we don’t have to go through security and check our bags twice. As a bonus, you can say you’ve been to two countries on a different continent.”

The look on her face suggested she wasn’t thrilled… but she wasn’t outright rejecting it either.

“Do we have to go back through Taiwan to go home?”

Triple shit. Maybe my overconfidence didn’t crack the code.

“Shouldn’t we at least try to do the airport shuffle in Tokyo just so we know what to expect… that, and you know, it’s cheaper?”

She had a point. Still, I wasn’t going to give up on this.

“Let’s do both,” I said. “We fly out through Taiwan on the way there, and then we fly back through Tokyo so we can experience the airport shuffle.” She rolls her eyes at me.

“Fine,” she said. “One more request, please?”

“Yes?”

She smiled the kind of smile that’s really a command and said, “Can I have an aisle seat, please?”

Because I know her, I already had our optimal seats picked out. “Done. And we’ll get all the miles.”

So, with our trip booked, we’re ready to fly to Asia on our first international trip together.

Slowly, the days count down until we take off for Seattle International Airport (SEATAC, if you please). We pack up, head to the airport, and prepare to take off for Japan. All my life, I have been waiting for this moment, and it has finally arrived.

Sometimes, it is only through hindsight that we see the moments our lives shift. Other times, those moments happen so boldly that you’d have to be obtuse not to notice. This was one of those moments. Whatever happens from here on out, life will never be the same. For now, it’s enough to take in that last bit of quality Seattle air (if you know, you know), acknowledge that we are about to cross a new threshold, and savor where we are. All is well, and I am the luckiest man on the planet.

Still, we have 18 hours of travel ahead of us, plus checking bags and getting through airport security. What could possibly go wrong?