Hello and welcome to your weekly dose of actionable (and occasionally provocative) things.

In the USA, you have to pay money to figure out how much money you owe in taxes.

Beautiful system. Very user-friendly.

You basically get two options.

  1. You can do it yourself with an app like TurboTax. Still paid, just with the exciting bonus of doing the confusion personally.

  2. Or you hire a CPA - a Certified Public Accountant - and gain the luxurious ability to ask follow-up questions while your financial dignity quietly leaves the room.

My 2025 tax situation turned out to be more complicated than I wanted to deal with, so I made the mature financial decision to spend more money solving the money problem and hired a CPA.

Then came the number.

After the initial shock passed and I remembered how to blink, I decided to get a second opinion.

Not because I was confident the CPA was wrong.

More because hope is stubborn, irrational, and occasionally expensive.

Once I finished my brief emotional intermission in the corner, my first instinct was to reopen my old TurboTax account and start manually stuffing numbers into forms like it was 2018.

But I wanted something lazier.

And, ideally, cheaper than hiring another CPA just to confirm the first CPA had already ruined my weekend.

So, naturally, I tried AI.

I spent seven minutes anonymizing our documents - blacking out names, addresses, and Social Security numbers - uploaded them into ChatGPT, and asked it to estimate our tax return.

Two minutes later, it gave me a detailed, comprehensive answer confirming that the CPA was, unfortunately, correct.

Same conclusion.

Same math.

Just faster, cheaper, and without another invoice attached to it.

I want to believe that soon, filing taxes in the U.S. will cost about $20 - the price of a monthly ChatGPT Plus subscription.

Instead, this year I have to pay what feels like several years’ worth of those subscriptions all at once.

Enjoy the edition!

Table of Contents

Heads-up: If you’re reading this in Gmail (either in the browser or the app), you might not see the full content. Since our emails are packed with rich content, Gmail loves to clip them. You’ll see a small note at the bottom that says [Message clipped] View entire message. Just click that link - the rest of the content is waiting for you on our website.

Learn From My Mistakes

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

Did you know that the pursuit of happiness is one of the constitutional American rights?

I didn’t know that either until I had to study for the naturalization test a few years ago.

Which is funny, because something important enough for the Constitution is something we seem to misunderstand all the time.

Mostly by treating happiness like a retirement plan. Suffer now, relax forever.

Like there’s some final level where confetti falls from the ceiling, a choir starts singing, and from that point on you just remain... happy.

Permanently.

Like a man on vacation who already set his out-of-office.

That part feels suspicious.

Because what was clearly missing from the “Intro to Happiness” training we all never got is this:

Happiness was never supposed to be permanent.

It was supposed to move.

When I was a kid, I could feel truly happy just because we had dumplings for dinner.

Peak life.

Then I grew up, moved out, became a student, and started living like a person who could eat dumplings whenever he wanted.

So I did.

And then I really did.

Night after night. Quarter after quarter.

And guess what happened to my happiness?

It got bored.

The happiness curve went from delight to normal to meh to I can’t even look at dumplings anymore.

Classic diminishing returns.

And yes, this works for almost everything.

  • Video games

  • Travel

  • Workouts

  • Late-night parties

  • Shopping

  • Fancy productivity systems

  • That first week with a standing desk

  • New gadgets.

Even the stuff we swear will totally change our lives this time.

It usually doesn’t.

Or rather, it does for a minute. Then your brain gets used to it and moves on.

Of course, there is one exception.

My marriage seems to work in reverse. I get happier with it over time.

(Honey, if you made it this far, thank you. You may now return to Bridgerton. Don’t worry, we still haven’t cancelled Netflix)

But a good life was never supposed to be happiness only.

It also includes boredom, grief, frustration, calm, joy, meaning, irritation, and those weird beige Tuesdays. That’s the package.

We can only recognize happiness because it contrasts with the rest.

Which means the point is not to make happiness permanent.

The point is to catch it before the slide gets too steep.

There are levels to this game.

  • Professional: expect every good moment to last forever. Then get grumpy the second it doesn’t.

  • Amateur: notice small lifts before they disappear.

    • A first sip of coffee in the morning.

    • Fresh bed sheets.

    • That exact moment when your head hits a cold, clean pillow and life briefly feels professionally managed.

After playing in the professional misery league for years, I’ve decided to spend some time in the amateur division.

Mostly for personal growth.

So here’s my tiny game for this month:

I added one word to my reminders.

Escalator.

Because the escalator is always on, and it always goes down.

If I do nothing, the ride tends to look something like this:

happy -> excited -> content -> indifferent -> disappointed -> sad -> miserable -> hopeless -> depressed

Cheerful visual, I know.

So my goal is not to reach permanent bliss.

My goal is much simpler: Don’t slide too far.

Ideally, not below “sad”.

Honestly, setting the bar low gives us amateurs a real competitive advantage.

The rule is simple:

Notice little bumps that interrupt the ride down.

And if there are no bumps, create one.

Over the past few days, here were mine:

  • Created: took a warm shower after pressure washing the patio. After standing in that cold mist for an hour, it felt less like hygiene and more like a reward from the gods.

  • Created: got my personal inbox to zero and cleared my Todoist for the day. Weirdly thrilling. A private little administrative festival.

  • Noticed: it started raining during my run. I enjoy that more than a normal person should.

  • Created: finally did my annual eye exam. Very glamorous. Very adult.

  • Noticed: my wife bought herself the exact flowers she wanted for International Women’s Day, which saved me from a very confused trip to the flower shop.

  • Unclassified but excellent: spent a chunk of my annual bonus on something my wife wanted but did not expect this soon.

And just like that, the floor moved a little.

Not a lot.

But enough.

Maybe happiness is not something we keep.

Maybe it’s something we restart.

Like a Wi-Fi router.

Annoying. But effective.

Till next time.

The Curious Procrastinator relies on word of mouth!

If you’re enjoying our newsletter, please help us reach more readers by forwarding this letter to a friend.

Our favorite digital finds

Tools, apps, and services that actually deliver

I like tools that solve small, stupid daily problems. Odio gives you spatial soundscapes for focus, sleep, meditation, or just covering up the many acoustic crimes of modern life.

Write 10x faster. MindNote is for people whose notes currently live across five apps, three screenshots, and one deeply cursed text file. If you’re into lifetime deals, buying it through Oncely gets you a huge discount.

Sending files between devices should not feel like a minor IT project. Airclap makes it stupidly simple to move files across Mac, iPhone, Windows, and Android on the same network

Short & Sweet

Short articles worth your attention

A helpful little audit for anyone wondering where their energy went, besides work, news, and being a person.

Apparently, the problem is not that we’ve become weak little babies. The problem is that boring work, tempting alternatives, and low energy make everything feel heavier than it needs to. Worth reading for the practical framing alone.

This is not a productivity article, which already makes it refreshing. It helps explain why quitting feels so uncomfortable - and why sometimes the smart move is to admit the deal just sucks.

Add this to your shelf

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

The best part is that you do not just hear people talk about process, you get to see the drafts, markups, doodles, and false starts. That makes the whole thing feel concrete instead of lofty. It is great if you like knowing what the work actually looked like before it got good.

Feeling the vibe? Drop your email and we will deliver more weekly.

A Workspace I Envy

A handpicked desk setup that caught my eye this week

Three things:

  • Correct monitor.

  • Correct monitor placement.

  • Absolutely terrible mouse.

Everything else is optional.

Behind the Persona

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

Sergey Brin has one of those careers that sounds fake when you say it too fast. Google co-founder, giant technical bets, repeated returns to the biggest frontier in the room. The interesting part is not just that he won big. It is that he keeps choosing work that could still fail in public. Nice little reminder for those of us procrastinating over one email.

Cool Facts About Sergey Brin

Office-First Sprinting: In a February 2025 memo to teams working on Gemini, Brin said people should be in the office at least every weekday and called 60 hours a week the sweet spot for productivity.

White-Coat Reviews: Google’s founders were reported to put on white lab coats when it was time to approve major new products. Silly on the surface, useful underneath - it turned big product calls into a deliberate ritual instead of just another meeting.

Dogfooding on the Commute: At a Stanford panel in late 2025, Brin said he uses an unreleased Gemini Live model during his commute to ask dense questions like data-center power and cost math. He tests the product in the cracks of the day, not just in formal demos.

Weekly Question Pressure: In Google’s early years, Page and Brin used the weekly TGIF all-hands as a standing feedback loop where employees could ask hard questions directly. That built a cadence of real-time challenge instead of letting issues marinate in side channels.

Failure Budget Mindset: Brin’s blunt rule was that the only way to have success is to have lots of failures first. Less inspiration-poster energy, more portfolio strategy - run enough shots that misses become part of the system.

Proof Before Leap: Page and Brin built Google as a research project in 1996 and did not leave Stanford to start the company until 1998. They let traction, system performance, and user pull do some of the decision-making before making the career jump.

Bare-Minimum Intolerance: Brin warned that people doing the bare minimum can hurt team morale, not just output. That is a very specific management heuristic: low effort is contagious, so standards have to be social as well as technical.

Startup-Speed Reset: During Google’s scramble to catch OpenAI, Brin pushed for the company to move closer to startup speed and take bigger risks instead of letting too many people veto products. His decision rule looked like this: fewer blockers, faster approvals, more bets.

Hard-Problem-First Thinking: The broader X system built inside Alphabet used a rapid evaluation process that killed about 90% of ideas early and favored tackling the hardest constraint first. Brin helped create that culture, which is basically anti-wishful-thinking in organizational form.

Watch-worthy clips

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

Ever feel like your favorite apps keep getting worse in oddly specific ways? This clip turns that vague suspicion into a very clear joke, and the joke works because it feels a little too familiar.

Enjoying the newsletter? Please forward this issue to a friend who might enjoy it too 😊🙏🏻

It only takes 10 seconds. Making this one took us 9 hours…

If you are new here, what are you waiting for? ⬇️

Reply

Avatar

or to participate

Keep Reading