Learn From My Mistakes

Short story of how I break life chaos into small, solvable problems - 3 min read.

A few weeks ago, I visited a modern art museum.

First one since pre-COVID.

Here’s the hot take:

Museums are like IKEA:

• 80% poor-quality junk

• 18% okay-ish stuff

• 2% (on a good day) actual gems

Of course, that’s 95% subjective.

Museums are meant to be solo.

I love roasting stuff out loud, but halfway through, I realized: the only way to make sense of modern art is alone.

No whispering explanations. No blurbs. Just me, squinting at a rusted pipe glued to plywood.

Spoiler: 80% of it didn’t deserve wall space. But hey - this isn’t a luxury business. Volume pays.

The only filter that made sense? Effort.

And I noticed it showed up in two ways:

1. The artist (or company - hello, original Macintosh by Apple Inc.) actually tried.

2. The work reflected years of refinement and simplification.

Take Picasso’s bull sketches. From full realism to a few bold lines. That’s intentional evolution.

Then compare it to a canvas with random splatters labeled “abstraction.” I’m sure someone saw depth. I saw laundry day gone wrong.

At least there were no bananas duct-taped to walls. Small wins.

So, what’s the point?

Simple: Fear of Missing Out.

That subtle pressure to stay impressed. Even when you’re not.

I paid for the ticket, so yes - I forced myself to examine every weird piece like a responsible adult.

And even when I didn’t like something, I still heard it:

“Maybe I’m missing something.”

“Maybe this is genius and I just don’t get it.”

“Maybe I should pretend I'm impressed so I don't look dumb… Oh wait, I'm here alone. My reputation's safe. This piece sucks!”

That voice? Classic FOMO.

We do this all the time. With trends. With advice. With business ideas.

We assume there’s meaning because someone else said there is.

But maybe - just maybe - it’s okay to say, “Nah, this isn’t for me” and move on.

We nod along, click “Like,” or save it for later—not because it’s valuable, but because someone else said it might be.

Remember when NFTs were collectible art?

Or when Clubhouse was the future of conversations?

Good times. Weird times.

But here's the thing:

not everything that's popular is meaningful.

And not everything that's meaningful will go viral.

Sometimes the smartest thing you can do is walk past the abstract splatter and say, "No thanks. I've seen better."

That’s not arrogance. (ok, it’s a little arrogance.)

But mostly - it’s curation.

And in a world screaming for your attention, curation is power.

Here’s a tiny experiment I started last week: I began treating my digital life like a museum I curate.

If I wouldn’t hang it on my mental wall, it doesn’t stay.

No more saving articles “for someday.”

No more 42 tabs open just because they might be useful.

No more guilt-bookmarking.

If it doesn’t grab me now, I let it go.

No screenshots. No hoarding.

I trust the good stuff will make its way back if it matters.

It’s a quiet rebellion against FOMO. And I’m curious to see who wins this round.

Till next time.

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A deep dive into the quirks, habits, and backstories that shape icons

Cool Facts About Brian Chesky

Design First, Always: Chesky studied industrial design at RISD (Rhode Island School of Design). He once said if Airbnb ever fails, it’ll be because they “forgot to be designers.”

Time-Blocking Devotee: Chesky time-blocks his calendar by “themes” to reduce decision fatigue. Mondays are for team meetings, Tuesdays for product, and so on. He once said batching decisions by topic helps him “think more clearly and go deeper.”

First Principles Habit: He frequently uses first principles thinking - breaking problems down to their core truths and rebuilding from there. He credits this habit with helping Airbnb survive multiple near-death moments.

Design Warm-Up: To get into a focused creative flow, Chesky sketches by hand. Even as CEO, he keeps this design habit alive - he says it helps him stay connected to the product and think visually, not just in words or spreadsheets.

“What If” Reps: Chesky regularly challenges his team with “what if Airbnb were invented today?” It’s a mental habit designed to prevent complacency and spark fresh thinking - even when things are going well.

Email to Jobs: In 2010, Chesky cold-emailed Steve Jobs asking for advice on how to grow Airbnb while staying true to its mission. Jobs never replied - but the fact that Chesky shot his shot says everything.

The $40 Photo Fix: In the early days, Chesky realized that bad photos were killing listings. So he and co-founder Joe Gebbia rented a camera and personally photographed hosts’ homes in New York. Bookings doubled almost overnight.

Cereal Hustler: Yep - during a cash crunch, Chesky and the team sold novelty boxes of “Obama O’s” and “Cap’n McCain’s” cereal during the 2008 election. They made $30,000 - just enough to keep Airbnb afloat.

Lives Like a Host: After Airbnb’s IPO, Chesky sold his house and started living full-time in Airbnb listings. He called it his “digital nomad experiment” - and lived in a different city every few weeks.

Creative Constraints: Chesky believes limitations fuel creativity. He once said, “Constraints are the key to innovation,” pointing out that Airbnb’s best ideas came when the team had no money, no time, and no options.

Forgoing a Salary: During the COVID-19 pandemic, Chesky took no salary for the year and slashed executive pay to preserve the business—while issuing refunds and setting up a $250M host relief fund.

Watch-worthy clips

One video that got us thinking, and we think you'll like it too

Discover Ikigai - a Japanese concept that basically answers the question: "What should I do with my life?" (No big deal, right?). This video breaks it down into four parts: what you love, what you're good at, what the world needs, and what pays the bills. Also helpful if you're crushing it in three and totally blank on the fourth.

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