Chapter 1: Don’t Waste Time Planning

Let Serendipity Guide You

I’m going to dive right in and give you the best advice upfront right here in chapter one: Don’t waste your precious time at that crazy tourist attraction.

The ultra-busy, overcrowded places that — yes — are amazing — but will cost you your soul to enjoy.

Don’t try to find a step-by-step day trip plan.

Don’t try to map out every step of your journey.

Especially don’t try to schedule out every moment of the trip.

Not only do these things take a long time to set up, and you’re always going to feel like you could have done it better, but there will inevitably be a problem throwing off your plans.

And in a country where you probably can’t speak/read the language, you are almost guaranteed to run into problems with a strict plan.

So what should you do instead?

In this chapter:

  • A Plan That Isn’t a Plan
  • Sometimes It Will Be Fun; Sometimes It Will Be Absolutely Incredible
  • Pick the Station; Enjoy the Experience Just the Same
  • The Best Part

A Plan That Isn’t a Plan

Serendipity At Its Best

Here’s what you do. And the reason at first may not be apparent, but you’ll understand soon.

By the way, this trick is when you’re already in Japan.


Pack a Bag

You’ll want a few basic essentials. Things like money, a drink, a hand towel… maybe a snack.

Pack light. You’re not embarking on a dangerous hike through arctic bear country.

You want items that will help you out in an urban setting and the current season.

Also, you want free space in the bag, so when you discover interesting things and make purchases, you have somewhere to store them without becoming a burden.

Pro tip: add some plastic bags to your inventory. Sometimes it can be difficult to find trash cans in Tokyo. 

Get on the Nearest Train

It’s almost time for the adventure to begin. Actually, in some ways, this could be the starting line.

It’s a simple step. I need you to:

  1. Walk to the nearest train station and get on a train. Pretty much any train will suffice
  2. Ride for any random number of stops
  3. Get off the train

Explore the Train Station Area

Now the true adventure begins.

You think I’m joking, but I’m not. Every station will have something new for you to discover.

From a boutique souvenir store to an amazing ramen shop, or a mom ‘n pop izakaya that’s been in the family for decades.

Sometimes It Will Be Fun; Sometimes It Will Be Absolutely Incredible

The streets around train stations range from dank, narrow alleys at the smallest stations, to remarkable atmosphere and character at others.

And they’re all different.

For example, get off at Nakano station and you’re greeted with a long corridor of shops under a brightly colored archway. At the end of this corridor is a geek mecca: The Broadway Mall — full of the most obscure collectibles.

Get off at Shibuya station and you’ll be lost in the labyrinth before figuring out how to even exit the station to find that famous Shibuya Crossing.

Or if you get off the train at Akishima station you’ll find packed back alleys outside one exit, and a nice shopping mall out the other exit (there’s a fantastic Harley Davidson store here too).

My point is you will almost always find something you will enjoy. And if not, get right back on the train and move along to another station.

Easy as pie right?

Okay… what if you want to pick the station? Does that ruin this whole “serendipity” thing?

No. It does not. So long as you don’t go any further than planning the station. We’ll talk about that next.

Pick the Station; Enjoy the Experience Just the Same

Maybe you’re the type of person who dreads the idea of going to a random train station without a plan. Maybe it even stresses you out a little.

That’s alright. Perhaps the following tactic can help. Because in the end, we’re trying not to over-plan the entire trip through and through — but a bit of planning is fine.

Here’s what you do. 

From the comfort of your home, hotel, or Airbnb:

  1. Open Google Maps on  your smartphone
  2. Locate the train station nearest you
  3. Find another station along the same track
  4. Go there

But don’t spend time researching what’s there. Just go there. Let the ambiance… the sights, sounds, and smells draw you in.

Free your mind. Let the adventure take you wherever it wants you to go. Your emotions and the way you feel at the moment will drive which shops you visit, or which streets you decide to explore.

And don’t forget to let your stomach and nose help you dive into some of the awesome izakaya all-around train stations.

In later chapters, you’ll learn more about the various parts of Tokyo to help you make more informed decisions. 

The Best Part

The magical thing about this technique, aka “the best part,” is no matter how long you’ve been in Tokyo (or how many times you’ve visited) there will be something new to discover.

Take me for instance. I’ve been in Tokyo since 1996.

I know, it sounds impossible to me too. Being in Tokyo 24+ years has been incredible and wow has the time flown by!

Even after all this time, there is one thing I can always count on — train stations.

I know no matter what, and without planning, my wife and I can hop on a train, explore, and create new memories together.

That’s what I want for you.

Get out there — create new memories.

In the next chapter, we’re going to do a quick orientation of Tokyo to help you make sense of this sprawling metropolis.

Next Chapter: Tokyo Orientation