I've Declared Email Bankruptcy (Again), but This Time I Have a Plan

In 2004, Lawrence Lessig sent out a mass email to his entire contact list saying, more or less: "Sorry, I deleted all your emails without reading them. If it was important, send it again." He had spent 80 hours that week trying to empty an inbox cluttered with emails dating back to 2002. He was getting 200 emails per day.

Lessig wasn’t disorganized. He was a Law Professor at Stanford. And even so, email defeated him.

I’ve declared email bankruptcy at least three times. The first time felt cathartic. The second time felt pathetic. By the third, I started to realize the problem wasn’t me.

Email Is an Inbox Anyone Can Fill

Think about it for a moment. Your inbox is a to-do list that anyone on the planet can add to without asking you. Your boss, your bank, some guy you met at a conference four years ago, a newsletter you signed up for when you were drunk, a Jira bot notifying you that someone moved a ticket from "To Do" to "In Progress."

Everyone adds things to your to-do list. No one asks if you have room for it.

It’s like leaving your front door wide open with a sign that says "drop off whatever you want me to do here." And then being surprised by the mountain of packages in your hallway.

The Universal Misuse

Email was invented to send messages. A message. From one point to another. Like a letter, but faster. Perfect.

The problem is what we’ve turned it into:

In plain language: we’ve taken a hammer and started using it as a screwdriver, butter knife, and bottle opener. And then we complain when the handle breaks.

The Numbers of the Disaster

A study by the University of California, Irvine found that it takes 23 minutes and 15 seconds to fully refocus after a significant interruption. The average worker checks their email 36 times per hour. That’s 36 potential interruptions every 60 minutes.

Do the math: if each glance at your email costs just 2 minutes of mental context-switching, you’re wasting over an hour a day on context-switching alone. Not on reading emails. Not on responding to them. Just on checking to see if something new arrived.

It’s like driving while randomly jerking the wheel every 100 meters. Technically, you’re moving forward, but you’re burning twice as much gas and arriving completely worn out.

Why Bankruptcy Doesn’t Work (and You Know It)

Every time I’ve declared email bankruptcy, the cycle went like this:

1. Week 1: Inbox zero. Absolute peace. "This time, I’ve got it."
2. Week 2: 47 unread emails. "I’ll get to them later."
3. Week 3: 200 emails. Some important. I start squinting at subject lines.
4. Week 4: 500 emails. I can’t tell what I’ve read and haven’t. Anxiety sets in.
5. Month 3: Bankruptcy again.

The problem isn’t that you’re disorganized. The problem is that email, as a task and reminder management system, is structurally incapable of working. It doesn’t have priorities. It doesn’t have due dates. It doesn’t manage statuses. It doesn’t distinguish between "read this whenever" and "respond today or lose the contract."

Everything comes in the same way, in the same format, and it’s dumped into an infinite list sorted by "who spoke most recently." That’s not a productivity system. It’s a chronological landfill.

The Solution Isn’t Managing Email Better

I’ve tried everything. Gmail filters. Color-coded labels that looked like a Tokyo subway map. Snooze. Folders labeled "Reply Today," "Reply This Week," and "Read Someday" (spoiler alert: "someday" never comes). I’ve tried FollowUpThen, which lets you forward an email to 3days@followupthen.com to have it return to your inbox in 3 days.

You know what happens when you use FollowUpThen? Now you have the original emails plus reminder emails. More emails to solve the problem of too many emails. It’s like trying to put out a fire with gasoline.

The real solution is to remove reminders and follow-ups from email entirely. No half-measures.

Memento: The Boring Solution That Works

My first solution is called Memento. It’s not a pretty app with a polished interface and subscription plans. It’s a 120-line Python script that queries Linear (my task manager) and tells me which issues are overdue.

# GraphQL Query: overdue issues, not completed or canceled
issues(filter: {
    dueDate: { lte: "2026-03-11" },
    state: { type: { nin: ["completed", "canceled"] } }
})

That’s it. A query that asks: "What should I have already done but haven’t?"

I run it from the terminal with one command:

uv run memento

And it spits out something like this:

⚠ 3 overdue issues in Linear:

  [TOK]
    TOK-42: Review authentication PR (overdue by 2d, state: In Progress)
    TOK-51: Update deploy docs (overdue by 5d, state: Todo)

  [FRR]
    FRR-12: Reply to talk proposal (overdue by 1d, state: Todo)

No frills. No push notifications. No red badges screaming at me from the corner of a screen. Just a flat list of things I’ve missed, grouped by team, sorted by urgency.

Why This Works and Email Doesn’t

The difference is subtle but fundamental:

Email is a push system. Others decide when and what you receive. You can only react.

Memento is a pull system. You decide when to check. And what you see is what you decided was important when you created the task.

Put another way: email is a tray others fill with work. Memento is a mirror showing you what you promised to do.

Deadlines Are the Key

The whole system hinges on one simple discipline: add a date to every task. It doesn’t have to be exact. It doesn’t have to be a contractual deadline. Just a date when you want to be reminded it exists.

If someone emails you saying "review this document," don’t keep that email in your inbox. Create a task in Linear with a date you’d like to review it. Archive the email. Done.

The email leaves your inbox. The responsibility lives in a system with priorities, statuses, and dates. And when you run memento, it’ll show up if you haven’t done it yet.

What if you miss the date? No problem. Memento doesn’t judge. It just says, "This has been overdue for 5 days." You decide whether to do it, postpone it, or cancel it. No guilt. No passive-aggressive reminder emails.

Not an App—A Philosophy

Memento isn’t some groundbreaking tool. It’s just a script that hits an API. You could build the same thing with Todoist, Notion, or a Google spreadsheet. The point isn’t the tool; it’s the principle:

Email is not a reminder system. Stop using it as one.

Every time you use email to "remember something," you’re trusting a system without priorities, dates, or states to do the job of a task manager. It’s like using a Post-it note to store your bank password. Technically it works. Until it doesn’t.

What Still Needs Solving

Memento is just the first piece. It solves "I won’t forget what I promised to do." But the broader problem with email has more layers:

• Asynchronous communication — Email is still necessary to communicate with people who aren’t on your team. But it doesn’t have to be your main channel.
• Archiving and search — Sometimes you need to find an email from three months ago. Email is fine for that (as a storage system, not an active system).
• Emails that require action — The real enemy. Emails that are neither purely informational nor spam but require you to do something. The rule: turn it into a task, archive the email, and let it die in peace.

This is still a work in progress. I don’t have the complete solution. But after three bankruptcies, I’ve learned one thing: the solution isn’t managing email better—it’s needing less email.

And the first step is to stop using email as a to-do list.

Immediate Action: The next time an email asks you to do something, don’t leave it in your inbox "for later." Create a task with a due date in your favorite task manager. Archive the email. And let the system with priorities and dates do its job. Your inbox is a mailbox, not your desk.