Table of Contents

• Learn From My Mistakes

• Our Favorite Digital Finds

• Short & Sweet

• A Tweet That Hits

• Add this to your shelf

• A Workspace I Envy

• Unpacking the routines of interesting people

• Watch-worthy clips

“Let it sink…”

This section is gone starting next edition, unless you email me back to keep it

Latest interview with Naval:

Chris Williamson: Success comes from dissatisfaction. Is success worth it then?

Naval: Oof. I'm not sure that statement is true anymore. Like I made that statement a long time ago and a lot of these things are just notes to myself and they're highly contextual. They come in the moment, they leave in the moment.

Me: O_o

Back to Table of Contents

Learn From My Mistakes

Short story of how I break life chaos into small, solvable problems - 4 min read.

My wife woke me up by poking my side with her elbow.

That was one of the most expensive naps of my life. About $1 per minute.

We were in a theater, watching (mostly her) a performance with top-tier artists we’d been looking forward to for months.

Not saying the show was boring (it was!), but I was tired after a long day. And who starts shows at 8 pm - right when my wind-down time begins?

The artists were great. But the seats? Even better - soft and inviting.

To my defense, I made it through the first half with normal blinking. Then the blinks got longer… and longer… until I was elbowed awake.

My wife’s argument was valid: “Dude, we bought expensive tickets. Not for you to sleep through it!”

Fair enough.

So I whispered and asked what I’d missed. She shushed me, and I backed off, trying to catch up on the lost plot.

Horrible experience.

So, naturally, I tried falling asleep again - but more discreetly this time. Unfortunately, the love of my life was now checking on me every 5 minutes, making the whole thing worse.

It took me years of reading until I stumbled across the name for what that night really was.

The Sunk Cost Fallacy.

In plain English (bear with me, I’m not a native speaker): It’s when we’re so invested in a bad experience that we keep going just to justify the effort or cost.

Let me decode it for my non-subscribed readers (obviously, the less enlightened ones who need a bit of help, until subscribed):

My wife’s point was - we paid for the tickets, so we must get the most out of the performance.

While the most reasonable thing for me would've been to just keep napping (I wouldn't dare suggest going home to see my bed - any marriage is based on compromises).

I bet you’ve experienced these pathetic moments too:

• Finishing a boring book. Unlike this newsletter, it’s dry, meandering, and hasn’t taught you anything in three chapters - but you keep reading because it’s been on your shelf for years.

• Finishing a TV show because you made it through the first season. (Hello, Severance Season 2 - burn in hell.)

• Gambling. “I bet this time I’ll get lucky!”

• Working on a relationship just because you’ve been together a while.
  (Though I have no examples for this one. My wife made it very clear: If it goes south, she keeps the house and car. I keep my iPad and take care of my in-laws, and we’re even. Still together. Unconditional love is powerful.)

I would mention “finishing a movie” too, but…

Have you ever watched The Sixth Sense with Bruce Willis?

We were students and rented a DVD (yes, pre-streaming era). Nothing else to watch, and the movie was so boring - until the end. We stopped sipping our beers and, without saying a word, unanimously decided to watch it again right away. So glad we didn’t give up.

Rare exception. Doesn’t count.

Now for a fresh example:

We’ve been having a ZZ plant (for non-Americans, that’s Zamioculcas) for seven years.

It started as a small housewarming gift.

But that thing started to grow!

After a few years, we upgraded the pot. That didn’t stop it.

Last month, when water stopped soaking into the soil, my wife suspected the pot was too small again.

Valid point.

But the next pot size up would’ve been a huge barrel - and we didn’t want that in the house.

So we decided to split the plant in two (yes, totally legal when it comes to Zamioculcas).

We went to Home Depot and bought the cheapest pot (same size) + a stand on wheels (that beast is heavy - I can only roll it around when it's time to clean) + soil + extras.

Total: just over $100. Pre-tariffs, post-taxes - in case you want to feel my pain more vividly.

The ZZ surgery was successful. We became proud owners of two large plants.

But now we had to decide where to keep the second one, as it took up a good chunk of our valuable real estate…

Emotions aside, we paid more than $100 to create another problem to solve. Just getting rid of half the plant or donating it to the Red Cross would've cost us nothing!

We were (my wife insisted on "we were" instead of "she was") so attached to the plant, there were no other options (yes, honey, there were! Oh god, if she reads this far, I'm going to regret it.)

So, how do you fight The Sunk Cost Fallacy?

It’s too late for me, but I should’ve asked:

“Hey, darling, would you buy another ZZ plant for $100 just to wonder where to put it?”

And if she hesitated, I could’ve tried framing it further:

“…or we could add a few more dollars and get that perfume you’ve been hinting at?” (I know I’ll end up buying it anyway - but at least this way I could try to solve two problems at once.)

I get it – it's hard to stop digging the hole deeper, especially after investing so much effort (or money, or both).

But the best question to ask is:

Would I start this now?

Be honest.

Focus on future returns (likely negative), not past losses.

Chances are, you'll get permission to DNF (Did Not Finish).

So yes, I'd marry my wife again - iPad or no iPad. But not gonna lie, the iPad was a pretty sweet bonus.

Till next time.

Our favorite digital finds

Tools, apps, and services that actually deliver

Short & Sweet

Short articles worth your attention

In a Slump at Work? Here's How to Motivate Yourself - 7 min read.

The title speaks for itself. It's aimed at remote workers for some reason, but I'm pretty sure it'll resonate just as much with those on-site.

How I've run major projects - 19 min read.

Deep dive into project management for devs. I'm not one, but I'm definitely stealing a few ideas for my own projects.

30 Areas of Life Where Subtracting Can Add More - 6 min read.

Surprisingly, I relate to most items on the list! The big exceptions are worry (I can’t consume that many sedatives instead of food) and cookware (no one’s perfect, okay?). I also read it twice - once when I discovered the article and again while adding it to the edition. Worth a reminder.

A Tweet That Hits

This section is gone starting next edition, unless you email me back to keep it

I might need to start reading Sahil's book, which has been sitting on my digital shelf. (I bought it to support the author I enjoy reading, and the signals suggest the content is decent.)

Add this to your shelf

If you're looking for something to read, this book's worth considering

Hidden Potential by Adam Grant is a guide to unlocking your best self. It emphasizes character skills - like grit, curiosity, and resilience - over raw intelligence as keys to success. Yes, being smart is not enough.

Workspace I Envy

A handpicked desk setup that caught my eye this week

Minimal colors, maximum aesthetic. The vibrant orange accent color adds a pop.

Unpacking the routines of interesting people

A closer look at how fascinating people structure their day

Interesting facts:

Self-Taught Coder by Age 18: Kalanick taught himself to code in middle school and by 18 had already written a complete SAT prep software program - before online test prep was even a thing.

Napster Lawsuit Survivor: His first startup, Scour, was a file-sharing service like Napster. It got sued for $250 billion by major media companies - yes, billion! He filed for bankruptcy at 23 but used the chaos as fuel for his next venture.

Rejection Fueled His Pitch: Investors initially laughed Uber out of the room. One early pitch deck was rejected by at least five top VCs. His response? Double down and launch in San Francisco anyway.

Obsessed With Efficiency: Kalanick once admitted he was so obsessed with optimization that he’d time how long it took to microwave food or shave, looking for ways to shave off seconds.

Phoenix Mode Activated: After Uber, Kalanick didn’t just disappear. He launched a new company called CloudKitchens, a secretive startup building "ghost kitchens" for delivery-only restaurants, buying up real estate globally under the radar.

Watch-worthy clips

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

Of course, this week it’s an interview with Naval. He doesn’t do them often. It’s long, split it into chunks.

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