How to do hard things

This is a system I only somewhat tongue in cheek refer to as “The Fully General System For Learning To Do Hard Things”. It’s a useful conceptual framework for how to get better at things that you currently find difficult.

I don’t always explicitly follow it, but I often find that when I’ve succeeded my success comes from implicitly following it, and almost every time someone asks me for advice on learning to do things I just describe a specialised version of the system to them.

The system “always” works in the sense that “eventually” either you will find out why the objective is impossible for you or you will succeed, but it’s very much the unhelpful kind of eventually where there’s no guarantee that it won’t take an interminably long time. The more likely outcome is that either you will succeed relatively quickly or get bored and give up, but that’s OK – the system is designed so that you will have gained benefit from following it at every step along the way even if you do not achieve your final goal.

I should also note that this system is not in any way a short cut. It’s a lot of work. The goal of the system is not to save you work, it’s to ensure that the work you do is useful.

The Single-Loop System

When you know what success looks like but cannot currently achieve it, the system works as follows:

The reason this works much better than just practicing the hard thing is because it gives you a much more direct feedback loop. There is exactly one aspect of the problem at any time that you are trying to get better at, and you can focus on that aspect to the exclusion of all else. When you are practicing something that is difficult in multiple ways, you will be bad at it in all of those ways. More, you will be worse at it in all of those ways than you would be if you’d tried them on their own. Additionally, when you fail you have to do a complicated root cause analysis to figure out why.

Instead, by isolating one aspect of the problem that is difficult, you will fairly rapidly improve, or hit the limits of your ability.

The Double-Loop System

If you don’t know what success looks like, you need to do double loop learning, where you mix improving your understanding of the problem with your ability to execute the solution.

Is this all a horrible oversimplification? Well, yes, of course it is. It is however a very useful horrible oversimplification that is very good for getting you unstuck when problems seem intractable.

How To Identify Points of Difficulty

Sometimes it will be obvious what you need to improve, sometimes it won’t. When it doesn’t, here are some things that can help you figure it out:

Worked Example: Learning to Write Better

This is particularly good as a mechanism for improving your writing (and writing about it is a good lead in to the mechanism on a particular area, so I’d encourage everyone to work on improving their writing).

Writing can be hard in a wide variety of ways. Some common ones (in roughly the order I think it’s worth tackling them) are:

And that’s even before you get into specific forms of writing. You could also struggle with e.g. dialogue, description, etc.

Set against this is the fact that if you’re reading this you definitely can write. I promise. You might not be able to write a novel (I can’t at the moment), but you can certainly write a tweet, and it’s just a series of incremental steps to get from there to wherever you want to be.

Here’s some examples:

  1. Learn to touch type if you can’t already. If you can’t touch type you will get blocked on the basic mechanics of writing. This makes the feedback loop for everything harder. Maybe try ztype, typesy, or Mavis Beacon1

  2. Learn to write in your speaking voice. If you can’t figure out how to write about a topic, try speaking about it into your phone (get a recorder app). Once you’ve started writing, try to read it out loud. This isn’t the only writing voice worth using, but it’s an important one.

  3. Practice writing without any expectation of quality. e.g. write in a private file or google doc, or create a blog with an explicit disclaimer that it’s for writing experiments. Some good writing experiments:

    • Observational writing. Pick an object (a lit candle is an interesting one) and write down everything you notice about it.
    • Pick a subject you are reasonably familiar with and set yourself a word count of, say, a thousand words. You can write whatever you want as long as you hit that goal. Feel free to write a stream of consciousness.
    • Pick an opinion of yours and write a 500 word case for it.
  4. Rather than worrying about the general problem of editing, start thinking about editing with specific goals. e.g.

    • This ties in well with getting a good writing voice. Read it out loud, figure out where good pauses are and put paragraph breaks in where natural pauses occur. Fix language that sounds awkward.
    • Try editing purely based on word count. Can you express the same thing with fewer words? What would you do if you had to cut the length of the piece in half?
    • Try editing ot remove specific words. Can you write the whole thing in up goer five? (Note: The result of doing so will be terrible, but the goal here is to practice editing more than produce a good piece)

There are plenty of other things to try, but these are some good starting points.

It’s now been most of twenty years since I learned to touch type, so I’m not that clear on how good any of these are