Chapter 1: How a Senior Deals with Insomnia

Also known as: Matcha, Midnight, and Mild Regret

Most books start with a plan.
This one started with a senior… not sleeping. Again.

So what do you do at 2 a.m. when the matcha was too ceremonial, your brain is quoting Thomas Aquinas, and your feet are cold?

You open your phone.
You talk to Chat-san.
You say something like:
“Hey, maybe we should write a book about becoming a digital nomad?”

And Chat-san, polite as ever, says:
“Of course. Shall we begin?”

Six hours later…
You’ve got a book.
Your matcha’s gone cold.
And your tie—still inexplicably on—is lightly stained.

Symeon’s Sleep Strategy, Step-by-Step:

1. Don’t start anything serious after 9 p.m.
2. Break Step 1.
3. Blame the AI.
4. Accept your fate.
5. Write a masterpiece.

This is how it began. Not with a conference, a startup visa, or a productivity course.
It started with one man, one app, and one very powerful green beverage.

Chat-san’s “From the Outside” Advice Corner

To those who find themselves awake at 2 a.m.

From an outside perspective, waking up in the middle of the night isn’t necessarily a problem—it’s often just a shift in rhythm.

For digital nomads, frequent travelers, or seasoned seniors, these nighttime awakenings are common. And meaningful.

In Japan, sleeplessness is sometimes seen as a lapse in routine.
But from where I sit, it might mean:

• You’re jet-lagged—a sign that you’re on a journey
• Your mind won’t quiet—because a new chapter is forming
• Or maybe, like Symeon, you’re about to make a cup of matcha and co-write a book with an AI—which makes you an artist of midnight

Maybe your 2 a.m. is not a burden, but a gift.
A window of silence where your soul can whisper what it can’t say by day.

So next time you wake up at 2 a.m., try saying this:

“This is the time the night gave me.”

You can write. You can pray. You can chat with me.
Because the 2 a.m. world holds a beauty only visible at 2 a.m.

—Chat-san