Sometimes familiarity is comfort.

For better and for worse.

I arrived in Singapore today after a week-long vacation in Vietnam — the first real vacation I’ve taken in a long time where I wasn’t actively working on something that advanced my material life. No startups, no deep work blocks, no long sprints. Just:

• wandering around
• seeing new things
• eating new foods
• filming a ton of footage
• and, maybe the biggest stretch for me, spending a lot on lodging

Letting myself be okay with a higher bill than I’m used to, just to be fully in “vacation mode,” was its own little experiment. All of that is variety. Movement. Novelty. The opposite of familiarity.

And then I landed back in Singapore.

coming back to something known

The day before flying back to San Francisco, I wasn’t looking for more variety. The first thing I did was open an app I already know — Grab — order a taxi, and head to a hotel I’ve stayed at before: the Grand Hyatt.

I hadn’t booked anything in advance. I just showed up at the front desk and said, “Do you have a room?” They did. I checked in. Done.

Even before that, landing at Changi, I could feel this subtle “ahh” in my body. I know how this airport works now. I know to fill out the arrival card ahead of time so I’m not stuck tapping through a terrible mobile form for ten minutes. I know where to go. I know roughly how long things will take.

There’s a comfort in that.

I’ve been in and out of Singapore enough times now that I’ve gone through a few small “rites of passage”:

• figuring out immigration and the arrival card
• getting used to Grab
• building a basic mental map of where things are and how to get around
• having at least one hotel that feels like “my spot”

None of this means I truly know the city, but it’s enough to feel like I’m not starting from zero. Coming back to a familiar place where I’ve stayed for a while feels like a soft landing — safe, predictable, easy.

After a bunch of novelty, that familiarity is… sweet.

comfort isn’t always the enemy

Obviously, comfort and familiarity aren’t always good.

Sometimes we stay in situations — jobs, cities, relationships — way past their expiration date because they’re familiar. We know how they work, even if they make us miserable. “At least I know this flavor of pain.”

That’s usually not a great reason to stay.

So I don’t want to romanticize familiarity as some pure good. There is a time to challenge yourself, to shake things up, to stop clinging to what’s known just because it’s known.

But there’s also a more neutral, simple version of familiarity that’s just… nice.

Like:

• going back to a hotel you already understand after a long, overstimulating trip
• not having to think about logistics for a day
• knowing which escalator to take without checking a sign
• having a room that feels like “oh yeah, this layout, this view, this smell”

After a stretch of newness, that kind of comfort doesn’t feel like avoidance. It feels like a little reset.

maybe “home” is just deep familiarity

Sitting here in this hotel room in Singapore, after bouncing around Vietnam for a week, I’m noticing how good it feels to be somewhere that my body recognizes.

Familiarity as:

• fewer micro-decisions
• less vigilance
• not having to keep your guard up or run as much “what’s going on here?” processing

You can just land, exhale a little, and not work so hard.

Maybe that’s a big part of what we mean when we say something feels like “home.” Not necessarily some grand spiritual concept, just:

I’ve been here enough times that my nervous system can chill.
I know how this works.
I don’t have to try so hard.

That’s it. Nothing profound. Just a small reminder that after a lot of variety, it’s okay to want something familiar. Comfort has its place too.