The Writers In My Inbox
On newsletters, writers, and the things worth keeping
Confession: I’m a digital pack rat.
Actually, let’s be honest. “Pack rat” is probably the charitable version. Depending on who you ask, there’s a reasonable argument to be made that I’m a digital hoarder.
If future archaeologists ever gain access to my email archive, they’re going to learn an alarming amount about my life. They’ll know what I bought, when I bought it, where I bought it from, and probably what I paid for it. They’ll find receipts, invoices, warranty information, utility bills, account notices, support tickets, and all the other digital breadcrumbs that quietly accumulate over a lifetime.
The funny thing is that I know exactly why I keep most of it.
Every so often I’ll find myself trying to remember something. When did I buy that? What was the model number? Which account did I use for that service? A quick search later and there it is. Past Chris helping Present Chris — and probably even Future Chris — solve a problem. Those emails are records. They’re useful because they document something that happened.
For years, I assumed newsletters belonged in that same category.
They arrived in my inbox alongside work messages, bills, receipts, account notices, and all the other things competing for my attention. Sometimes I read them right away. Sometimes I saved them for later. Sometimes “later” turned into weeks, months, or even years.
But unlike most email, I almost never deleted them. At the time, I assumed they were just another type of email. At least, that’s what I thought. The reality was different, but I didn’t realize it until much later.
Over the years, I’ve subscribed to newsletters about investing, technology, Apple, software, business, and whatever else happened to capture my attention. Some were written by journalists. Some by analysts. Some by independent writers building an audience one issue at a time. Some had been showing up in my inbox for so long that seeing their name felt as familiar as hearing from an old friend.
One day it hit me that I wasn’t saving those newsletters for the same reason I saved receipts. I wasn’t saving them because they documented a transaction. I wasn’t saving them because they proved something happened. I was saving them because I cared about the people writing them.
That sounds obvious now, but it wasn’t obvious to me at the time.
Many of the newsletters I follow are written by people who spend hours every week thinking, researching, writing, editing, and refining something they hope will be worth a few minutes of my attention. They pour their expertise into it, sure, but also their humor, curiosity, frustrations, experiences, and personality. Over time, you get to know their voice. You learn who makes you think, who makes you laugh, who has great taste for product recommendations, and who consistently points you toward ideas you would have missed on your own.
Some of those writers have been showing up in my inbox for years — longer than many software applications I’ve used, and hell, even longer than some jobs I’ve had, come to think about it. Long enough that opening one of their newsletters doesn’t really feel like checking email anymore. It feels like hearing from someone.
The longer I thought about it, the more newsletters reminded me of something much older: letters.
Actual letters. Not business correspondence, bills, or account notices, but the kind people used to write because they had something to say and someone they wanted to say it to.
The medium changed. Ink and paper became pixels, ones, and zeros. But the relationship didn’t.
A good newsletter still feels like hearing from someone.
That’s why I saved them.
Or at least, that’s why I save the good ones.
Not every newsletter survives. Plenty get deleted. Plenty get unsubscribed from. Plenty turn out to be less interesting than I hoped they would be.
But the ones that stay? The ones that teach me something, make me laugh, challenge my assumptions, or arrive at exactly the right moment? Those are the ones that stick around.
And once I saw that, I couldn’t unsee it.
In reality, I had spent years building a library.
One folder in particular finally made me realize this. It was called Berkshire Hathaway.
At some point over the years I had started filing investing newsletters into that folder. By the time I really stopped and looked at it, it contained years of commentary, annual meeting notes, investing ideas, market observations, and writing from people I respected. Some of those messages had survived multiple computers, multiple Apple Mail client versions, and multiple chapters of my life.
The strange thing was that I wasn’t treating any of it like email.
I wasn’t replying to it. I wasn’t forwarding it. I wasn’t trying to get to Inbox Zero.
I was treating it like a bookshelf.
That’s where this story eventually intersects with Letterboxx.
When I started building the app, one of the first things I did was create a brand-new email address dedicated entirely to newsletters. Then I spent weeks updating subscriptions I’d accumulated over more than twenty years. New newsletters began flowing into that new address through Letterboxx. Everything felt clean, organized, and intentional.
For the first time in years, when I wanted to read my new newsletters, I didn’t open Mail.app on my Mac. Instead, I fired up my still-work-in-progress instance of Letterboxx in Xcode and, to be honest, it felt fucking AMAZING. Finally! Now I finally had a way to separate the things I needed to read from the things I wanted to read. I loved it.
No work email.
No bills.
No spam.
No receipts.
No account notices.
Just newsletters.
For the first time, it felt like that part of my digital life had its own home.
Except it didn’t.
Because all of the newsletters that mattered most to me were still somewhere else.
The investing newsletters in my Berkshire Hathaway folder were still sitting in my old account in Mail.app. The technology newsletters I’d been following for years were still there too. So were countless others I’d collected over the years. Apple. Design. Software. Technology. Investing.
Looking back, those folders weren’t really collections of newsletters. They were collections of interests. Collections of curiosities. Collections of ideas that had seemed important enough at one point in my life that I wasn’t willing to throw them away.
If someone spent an afternoon browsing through those folders, they’d probably learn more about what fascinated me over the last twenty years than they would from my resume.
And the more I used Letterboxx, the stranger that felt.
My current newsletters were in one place. My history was in another.
Nothing was technically wrong. Everything still worked. I could still access those email folders in Mail whenever I wanted. But it felt strange and wrong to have my newsletters scrambled across apps and accounts.
The collection wasn’t together.
Looking back, I think that’s what bothered me so much.
Those folders weren’t just storage. They were a map of the things I’d cared about over the years. Investing. Apple. Software. Design. Technology. They represented countless hours spent reading, learning, wondering, and occasionally changing my mind.
Having them split apart felt less like an organizational problem and more like finding chapters of the same book shelved in different rooms.
The thing that surprised me most was that I wasn’t frustrated because the software wasn’t working. I was frustrated because the story wasn’t complete. The newsletters arriving today were separated from the newsletters that had shaped how I thought years earlier. My current interests were in one place. My history was in another.
I wanted them together. Not because they were email. Because they were part of the same collection. And maybe because the "pack" portion of being a digital pack rat really needed things to stay together.
That’s ultimately what led me to add support for connecting specific folders and multiple accounts. So I updated Letterboxx to look beyond a single inbox. I connected my personal email account, pointed Letterboxx at my Berkshire Hathaway folder, and watched years of newsletters appear alongside the new ones arriving every day.
Nothing was moved. Nothing was taken away from my mail account. For the first time, everything simply lived together.
And for reasons that are probably difficult to explain to anyone who isn’t also a digital pack rat, that felt like fucking magic to me.
That experience changed the way I think about newsletters and Letterboxx. It went from being a place to start over with newsletters to a place where you could also bring your history with you.
I still save newsletters. Probably more than I should. And I still have email folders that future archaeologists would find fascinating.
But I’ve stopped thinking of newsletters as electronic mail.
They’re the thing you didn’t know you needed to read that day.
The writer who makes you laugh after a difficult day.
The person who explains something you’ve been struggling to understand.
The idea that sends you down a rabbit hole for the next three hours.
The perspective that changes your mind.
The encouragement you needed to hear from someone you’ve never actually met.
Over the years, some of those writers become familiar companions. Their newsletters mark different chapters of your life. You remember where you were when you first subscribed. You remember the ideas they introduced you to. You remember the moments when something they wrote arrived at exactly the right time.
That’s why I save them.
Not because they’re email.
Because they’re people.
And because some of the most meaningful things we carry with us arrive one message at a time.