_{Sunday, 7:22pm
Asakusa, Tokyo, Japan}

Hi there!

I’ve been settling into Japan over the last few weeks. A quick recap:

• Hiroshima: Visited the Peace Memorial and Atomic Bomb Dome (and celebrated my birthday—I’m officially 26! 😯)

• Kiso Valley: Hiked through sections of the Nakasendo, an ancient highway that stretched from Kyoto to Tokyo. 🛣️ 

• Matsumoto / Japanese Alps: Matsumoto is now one of my new favorite cities in Japan! It’s a mid-sized city known for its pure natural spring water, delicious soba, and easy access to the Japanese Alps. ⛰️ 

• Tokyo: Met up with a couple old friends from study abroad 🎉 

Running out of travel steam

At this point, I’m pretty tired of bouncing between hostels.

As much as I love exploring, you can have too much of a good thing.

In no particular order, I miss:

• Having a regular exercise routine

• Waking up in the same bed every day, without being subject to the wakeup schedules / sleeping habits (i.e. snoring) of my hostel mates

• Hanging out with a consistent friend group

• Blocking out time to make progress on a long-term project

• Cooking my own meals

The original plan

My original plan was to end my time in East Asia with this itinerary:

• September: Japan

• October: Taiwan, Hong Kong, Mainland China

After my East Asia chapter, I planned on going to South Asia:

• November: Nepal, India

• December-January: India, Pakistan

However, I’m now considering putting a pause on the traveling after October. Putting recent political developments aside (like the Nepal protests), I figure by that point I’ll be too drained to properly immerse myself in the places I’m visiting.

So what’s the new plan?

I’m still working out the details, but here are few core things I want to focus on this upcoming year:

1. Continue my language learning journey

2. Start working on my own project, with the goal of launching it as a product

3. Stabilize my living situation, pick a place to live for the next year and make a consistent friend group

My thinking has evolved a bit over the last few weeks, but right now, my most likely course of action is to:

1. Pick up learning Japanese again, aim to pass the JLPT N2 (N1 as a stretch goal), before focusing on other languages (e.g. Korean, Mandarin)

2. Begin design, development, and testing of a new language learning companion app idea I’ve been refining—primarily to help with reading comprehension.

3. Move to Japan (most likely Tokyo), enroll in a language school for one year, and find a long-term living arrangement

How I arrived at this decision

Some of you might be surprised by my new plan, others not so much.

This was a hastily written newsletter, and I left out the internal debates that led me here. I may go back and do a proper writeup, but as a teaser, here were some other options I was debating:

• Returning to the PM career path vs working on my own project

• Learning Korean vs Chinese vs Japanese

• Moving back to the US vs staying abroad

I’ve also pivoted quite a bit in my areas of interest (remember when I was talking about the creator economy? 😅)

Here are a couple of the guiding questions I’ve been following in order to make decisions over these last few months:

• What am I naturally more drawn to? What feels energizing vs draining?

• What will help me grow towards the type of person I want to become?

• What will I regret more?

And so far, my current plan seems to check the boxes. ✅ 

Closing thoughts

Thanks for following along with my bumpy journey—if you have any questions, advice, or feedback, I’d love to hear from you!

Until next time,
Tim