Hello and welcome to your weekly dose of actionable (and occasionally provocative) things.
Last week I did something reckless.
I installed OpenClaw (an agent that can work with real files on my computer) directly on my personal MacBook, in my one and only environment.
A few weeks ago, I tried to isolate it twice.
First in a dedicated virtual environment, then in a separate user account on my Mac.
Both setups felt clunky and overcomplicated, so I decided to go all in instead.
The stakes were manageable.
I run a weekly full backup to an external HDD that’s connected only during backup time.
I checked recently: my whole life archive is a little under 2TB, including cloud exports, photos, and family videos.
Honestly, not that huge - streaming killed my old music and movie hoarding habits. I’m also very selective about what photos and videos earn a permanent place in the archive.
So far, the experiment is going well.
AI agent have finally organized my movie watchlist database in Notion and added IMDb scores - super helpful for TV shows, since Netflix doesn’t provide ratings.
I’d also been meaning to redesign my Obsidian digital garden (currently a bit over 2,000 notes), which felt less like a garden and more like a forest.
That exercise was mind-blowing!
I couldn’t clearly explain what I wanted in words, so I took a screenshot of a note and drew the changes.
Ten minutes later, everything looked fresh and gorgeous.
Just kidding - it took five.
If you’re curious about my OpenClaw experiments, let me know. Just hit “reply” and say “oh yeah!”
A few more days until my new friend’s new home (a Mac mini) arrives.
In the meantime...
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.
During one of my monthly family budget reconciliations, I noticed a tiny shift that felt… gross.
Not “we overspent on groceries” gross.
More like: we own fewer things, and we rent more of our life.
Earlier
We used to buy stuff once and be done.
CDs and DVDs for music and movies.
Software license keys.
Film for a camera, then printed photos, then stuffed them into albums that lived on a shelf.
A game you bought once (disc or download) and it was yours.
A car where the features were physical: seats, engine, radio.
Microsoft Office you bought one time.
Your identity lived in your head and on a couple cards in your wallet.
Now
Now we pay for access. And we pay forever.
Music is a monthly fee, and next year’s price is a surprise reveal.
Cloud storage becomes a compounding micro-bill that grows as your life grows.
Side quest: try getting your full photo library out of Google Photos. You will feel emotions.
Games turn into subscriptions, season passes, and battle passes that expire on schedule.
MS Office becomes rent, and then quietly becomes “family plan required.”
Cars ship with hardware, but features are gated behind subscriptions (remote start, connected services, driver-assist add-ons).
Heated seats as a monthly fee used to be a joke. Suddenly, it became a payment option in some places.
Password managers, VPNs, identity monitoring, and credit freezes become a monthly “please don’t steal me” line item.
And yes, we still pay for the boring fundamentals on top. Internet. Electricity. Gas. Sales taxes.
So the bill pile grows.
And then it hit me.
Years ago, I moved from free Google Sheets to a paid (annual!) YNAB subscription to track my personal finances.
I pay money… to better understand what I pay money for.
Now you know what recursion is.
Life As A Service
In practice, life is getting designed so we don’t own.
We rent.
Indefinitely.
And the weirdest part is how often we are trained to pay for peace of mind “just in case.”
Honestly, when was the last time you reviewed the photos in your cloud library from three years ago?
My wife says “regularly,” but refuses to define the interval.
Which is funny, because I love Lightroom - it’s an amazing photo catalog.
Do I use it weekly?
I’m not even confident I use it monthly.
So I started looking for a way out of the madness.
Not a full escape. Just a small rebellion.
Own a little more. Rent a little less.
The counter-move: my home server era
If you’ve been reading these editions for a while, I have exciting news.
I got approval from my lovely CFO (the one I’m married to) to shut_da_f_up_and_get_that_f'ng_home_server.
As usual, I’m late to the party.
Memory prices for computers decided to go a little over the moon over the last two quarters.
So I landed on a Mac mini with an M4 chip instead of building a Linux box with similar specs.
Now this newsletter is officially sponsored by Apple, who kindly agreed to keep prices intact for me.
But why do I need a server at home?
Thanks for asking.
1) Photos, but mine
I’ve been playing with Immich for a few quarters now.
The only real con: when my MacBook sleeps, the photo library sleeps with it.
On a dedicated machine running 24/7, that problem goes away.
And suddenly I have terabytes of storage for original-quality photos without a monthly fee.
2) Plex
If you know, you know.
(Winking, but responsibly.)
3) AI agents, locally
If you’ve been even casually watching the AI tsunami, you’ve seen the new species show up: AI agents.
Little dudes that can live on your computer and work with your files and apps locally, using a model like ChatGPT as the brain (oversimplified, but close enough).
I’ve been tinkering with one called OpenClaw for a few weeks.
It deserves its own home.
An isolated (!) home.
The current state of the mission
As I’m writing this, the Mac mini arrives in a day or two.
I’m basically staring out the window like a golden retriever waiting for the mail truck.
Also, the 3D printer is already preparing a mount so I can attach it under the desk.
Yes, I influenced myself with my own “A Workspace I Envy” section.
Again. Recursion.
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
Your camera roll is full of great memories and zero wall art. PortraitArt turns a photo into something you can actually frame, in about the time it takes to overthink fonts.
Pinterest is fun until you need to actually find the thing again. Eagle is basically Pinterest, but local. A better way to collect, search and organize your design files in a logical way and all in one place.
Gmail is already a full-time job. Simplify makes it look and feel less like a cockpit. It just quietly improves Gmail in hundreds of small ways.
Short & Sweet
Short articles worth your attention
Why Life’s Low Points Make Us Obsessively Productive - 3 min read.
Low points can make you oddly efficient, which is useful and slightly annoying. This piece explains why stress can narrow attention, cut fake urgency, and force choices you avoid when life feels fine. It also shows how to keep the useful parts without turning into a sleep deprived machine.
We Don’t Remember What We Think, Only What We Do - 5 min read.
Highlighting wisdom feels productive, but habits are what make insight real. If an idea never reaches your calendar, your body, or your routine, it never really lands.
Invisible Habits - 10 min read.
It calls out the tiny habits that look normal but quietly eat our focus all day. Each point ends with a practical fix you can apply today.
Add this to your shelf
If you're looking for something to read, this book's worth considering
How to Decide is basically a user manual for your brain’s worst hobby: overthinking. Annie Duke (ex-poker pro) breaks decisions into simple tools you can actually use, so you stop confusing “a good outcome” with “a good choice” and start getting better at playing the odds. It’s practical and fast.
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
Not the workspace I envy, exactly - more like an ode to the Japanese art of clutter. In the right hands, it can be both beautiful and brutally productive.
Behind the Persona
A deep dive into the quirks, habits, and backstories that shape icons
Patrick Collison co-founded Stripe and still runs it. He pairs big curiosity with hard operating discipline, so ideas quickly turn into written plans, stress-tested decisions, and clear owners. He favors compounding work and strong systems over flashy wins and heroics. He looks calm, but it’s a deliberate way to make better decisions under pressure.
Cool Facts About Patrick Collison
Default to written clarity: In early Stripe product reviews, Patrick would stop the room when everyone was “roughly aligned” and ask for a one-page writeup before any major decision. The move slowed things for a day, then saved weeks of confusion.
Rural standards test: In small-town Ireland, Patrick compared people by output, not prestige labels. That habit made him chase hard environments instead of comfortable ones. He later repeated this as explicit career advice.
Teen years with many disciplines: As a teenager, he spent serious time on code, math, physics, languages, and writing. The mix looked messy from the outside. It gave him more ways to attack one problem.
Looking strange on purpose: He has said that local approval is a weak compass. In early career decisions, he treated social weirdness as useful signal. The tension was clear: fit in now, or build something rare later.
Internet as talent network: He described the internet as a force multiplier for meeting strong builders. Instead of passive browsing, he used it to find people doing difficult work.
Older books filter noise: In interviews, Patrick said most people should be biased toward older books. Time had already killed weak ideas and kept the strong ones alive. He used that filter to lower decision noise.
Buying books before readiness: He bought strong books before he could fully use them. Many sat around his home for months before clicking. The scene is simple: future tools waiting in plain sight.
Reader-book timing: He has noted that a great book can feel flat at the wrong moment. Later, after new context, the same pages can become sharp. He treats reading as timing, not just effort.
Spec vs implementation check: When a process failed, he asked one question: broken implementation or broken spec. The frame stopped teams from blaming the wrong layer.
Watch-worthy clips
One video that got us thinking, and we think you'll like it too
Here’s a weird productivity take: boredom is training.
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? ⬇️
