The ultimate tragedy of unconstrained lifestyle design is realizing that absolute autonomy creates a chronological void.
I tried to remember what I did in May and came up with nothing. Checked my camera roll. Six photos. All food.
Two months of my life, and the only evidence they happened is a picture of pad thai in Lisbon and some fish tacos I apparently ate somewhere.
When I ran my logistics company, I could tell you what happened on any given Tuesday because every week had a shape. Monday was dispatch. Tuesday was client calls. Wednesday was the warehouse. Thursday was admin. Friday was putting out whatever fire had been building since Monday. I hated most of those days. I complained about them constantly. But I remember them. I can still feel specific Wednesdays from eight years ago. The forklift that broke. The driver who quit by text. The client who showed up unannounced, and I had to pretend the warehouse wasn't falling apart behind me.
Now my weeks don't have shapes. They have weather. Sunny, go surf. Rainy, work from the cafe. Some random Wednesday feels exactly like the Sunday before it and the Friday after it. I wake up, open my laptop for a couple of hours, close it, and the rest of the day is mine. Every day. Same beautiful nothing.
That's the trap. You build a life with no landmarks and then wonder why you can't remember living it.
Your brain doesn't store time evenly. It stores change. New things. Hard things. First times. Conflict. Surprise. When every day has roughly the same texture, your brain files them all in one drawer. A week in Lisbon with no structure feels the same as three weeks. A month in Bali blurs into three months. The days are good. They're also invisible.
Immediately after secretly redacting 750 White House files behind closed doors…
President Donald J. Trump wrote a check worth $300 million of his own money and strangely enough… didn't utter a single word about it to the cameras.
Even more fascinating, it turns out, Trump's not acting alone…
If you follow the money trail…
Jeff Bezos, Warren Buffett, Bill Gates… even an up-and-coming tech titan who the late Charlie Munger referred to as, "the new emperor of the world"… have all poured billions into the same area.
I met a woman at a hostel in Mexico who'd been traveling for two years. Fourteen countries. I asked her which one was her favorite, and she started talking and then stopped mid-sentence. She couldn't separate them anymore. They'd all merged into one long pleasant blur. She laughed about it, but her face did something else entirely.
You've felt a version of this. Maybe you work from home and realized the last three weeks have been functionally identical. You couldn't point to a single thing that made Tuesday different from Saturday. Maybe you finally got rid of every obligation you resented and noticed the days started tasting the same. Like eating the same meal over and over. Good meal. But you stop tasting it.
Maybe someone asked what you've been up to and you said "not much" and then sat with the fact that it wasn't modesty. It was accurate.
When I was delivering Chipotle at 35, broke, sleeping in my childhood bedroom, I can tell you exactly what those weeks felt like. They hurt. I remember the apartment complex where a guy tipped fifty cents, and I stood in the elevator wanting to throw the bag at the wall. I remember the parking lot where I sat listening to Tim Ferriss talk about stoicism while my check engine light glowed orange. I remember the night I counted my tips on the kitchen counter while my mom pretended not to watch from the living room.
Those months were the worst of my life. They're also the most vivid. Because difficulty is a landmark. Discomfort is a landmark. Anything that makes your nervous system pay attention gets filed where you can find it later.
My best months now, the ones where the revenue is good, and the waves are clean, and I'm healthy and free? I have to check my passport stamps to prove I was there.
What I've started doing isn't dramatic. I say yes to one thing a week that I wouldn't normally choose. Not something productive. Something that breaks the pattern. A different town. Dinner with someone I just met. A day trip with no destination. Last week I took a bus to a village I'd never heard of because a guy at the morning surf said they had a good bakery. The bakery was fine. Nothing remarkable. But I can see that day clearly. The yellow walls. The old woman behind the counter who didn't speak a word of English. The bus ride back, when it started raining, and the windows fogged up, and a kid across the aisle fell asleep on his mother's arm.
I didn't take a photo. I didn't need to. My brain kept it because it was different.
I used to think the whole point was to make every day feel like Saturday. Turns out a life made entirely of Saturdays is a life you can't remember by September.
— Best, Jose
P.S. Two more things before you go:
