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Origin3 min readOctober 7, 2026

Kill the Routine. And Build the Memories.

The danger is that your whole life can get put on autopilot.

A few weeks ago, I was on a podcast and shared a perspective on breaking routine. It resonated with a few people so I thought I'd take a break from AI and real estate and expand on that thought.

I've come to the conclusion that routine is the enemy. I'm not talking about habits here. Habits are good. What I'm talking about is routine.

I've driven to work before, on that same familiar route, and arrived to the office without remembering the drive whatsoever. My mind was focused on problems to solve or plans to make. That's your brain on autopilot.

Autopilot is a good thing because once you have solved a problem a few times, your brain can just handle that thing for you from then on. The danger is that your whole life can get put on autopilot.

I've gone through stretches of my career where I was just 100% about work and didn't take time off or focus on investing in other areas of my life. When I look back on those eras, I don't have a lot of rich memories.

I can see how easy it is to spend an entire career that way. Just wake up to the same alarm and do the same job every day. You end up not being able to recall what happened from one year to the next.

Contrast that with someone who had a few different jobs, got married, had a few kids, maybe lived in another country. Every one of those events creates a mental milestone. It breaks your life into different eras and makes it more memorable.

The good news is that you don't need to completely uproot your life to get the same advantages.

One easy answer to this is travel.

When you're in a new country that speaks a different language and has different food, you're on high alert. Your brain becomes like that of a child.

When I was a kid, it felt like summer lasted a decade. I think that's because as a kid you are constantly on high alert, drinking everything in. That seems to slow time down. As an adult, that's what travel does for me.

Those beach vacations where you sip a piña colada and read your favorite book while you watch the waves come in? That's vacationing. Travel is where you take yourself out of your comfort zone and do something challenging or inspiring.

There are a few travel moments burned into my memory. I remember the moment a sherpa hand me a hot tea as I watched the sunrise on the Annapurna trek. Telling stories over a campfire on a Yosemite camping trip with good friends. Caving in New Zealand and looking up at glowworms spread across the caverns like stars in the night sky. There are dozens more examples, and they all bring a smile to my face.

So get out your calendar, talk to your significant other, and get that big trip on the calendar. Your future self will thank you.

Kill the routine. And build the memories.