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2018.12.04 – How You Turn Depressing To-Do Lists into Productivity Weapons

You know that feeling when you realize you don’t even know where to begin because your to-do list now has more than 40 items?

I used to.

I don’t anymore because I learnt how to use to-do lists.

How do I know that?

Because I’ve kept a continuous to-do list for longer than I can remember now (months? years?) without ever worrying about anything on it.

Here’s a solid fact.

Most people’s to-do lists turn into depression pits where their hopes and dreams go to die. Because most people don’t know how to use to-do lists.

How does this happen?

Just look back to how lists are typically born – out of need, not out of Aspiration.

You desperately need to do something, so you write it down (sometimes in your calendar) to make sure you don’t forget it. You write it down to keep it on your mind because you need it.

This is the most rudimentary – and worst-case – scenario.

If you’re lucky, you might bother prioritizing things on your list by numbering or rearranging them.

That’s a step in the right direction, but.


It’s so much easier to shuffle things on your list on a computer or even online, where you can have it on all your devices, innit?

So your list ends up transferred to your calendar, to your computer, to the cloud, to your dumbphone and to the Vatican library.

Keep your list on the armpits of a pig for all I care. Here’s the why getting it off paper is a problem.

FIRST, by taking your list off the page, you allow it to become infinite.

Even if it never grows too much, it FEELS like it. On a computer, you can keep adding items to it forever.


You lose priority and discipline. You gain confusion and existential dread.

SECOND, you lose the reward of crossing things off a physical list and starting on a fresh page.

All manner of “life hackers” (a.k.a. unmotivated losers) yap about solidifying habits by allowing yourself a reward at completion of your daily quotas. Then why the frack forfeit the most fundamental reward of crossing your completed work off the list?

With a pen.

In your own hand.

The more physical you make it, the more you will improve your mind. The more digital you make it, the more it will confuse your mind.

PAY ATTENTION: This does not apply just to task lists. Take it as a universal law.

So what do you do to turn your lists from torture devices into weapons of success?

Understand that the primary role of your to-do list is not to remind you, but to allow you to forget.

You put the stuff on the list, so you can get it off your mind – NOT so you can keep it on your mind.

Allow yourself not to think about it while you’re dealing with other things.

Do things one at a time, then go back to the list – unless your instincts tell you what’s next without it.

If you have trouble prioritizing – picking 1 thing out of 40 to do NOW – there are tricks to help you.

  1. Use a coin, die or other randomizer to pick something for you.
  2. Pick the easiest, fastest, whatever thing and MOVE!
  3. Use a “cheat sheet” like I do: pick a handful of priorities off the master list, and the decision which one to do first becomes much less daunting.

And here’s the single best tactic to get about your business with extra momentum:

If you have a million things on your to-do list, start with the one thing you want to do least and requires the least amount of time.

When you’re done, don’t dwell on the easy success. RIDE on it towards the next task.

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Your Daemon

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