Strawman Yourself

Be a little careful about what kinds of arguments come to mind. If I run "look for the most obvious uncharitable insulting argument" on one of my current projects (writing a book), my oh-so-helpful brain immediately returns "It's arrogant for you to write a book. Also you can't finish a project this long. You're going to hit a hurdle and all the work will be for nothing!"

This, despite the fact that I've got a contract, my editor liked the first three chapters I sent, and I'm over halfway to the finish, look to be on track for deadline, and set aside a month of nothing but this at the end.

I'd suggest just being slightly more suspicious of insulting arguments that make claims about your character sucking (immutably) than ones about the way you've laid out the plan.

I do like this comment from "Die Vampire Die" as a countermeasure:

Who do you think you’re kidding?
You look like a fool.
No matter how hard you try, you’ll never be good enough.
Why is it that if some dude walked up to me on the subway platform and said these things, I’d think he was a mentally ill asshole, but if the vampire inside my head says it: It’s the voice of reason.

Sounds like a lesser version of Kahneman's pre-mortem with a different name (that I don't see as too appropriate to be honest, since this is not really what a strawman is).

I'm going to need some more examples, this sounds like it could be something but I'm not seeing how I could actually apply the concept to a situation.

Look at your plan in the most critical, contemptuous light possible and come up with the obvious uncharitable insulting argument for why you will fail.

Seems like an idea, but as I already see a million faults with my plans, and end up paralyzed thereby, I don't think this would help me out much.

My problem is generally more one of turning off the criticism than turning it on.

What you're suggesting is what I used to call self sadism, and I've concluded that it was decidedly unhelpful and unhealthy for me.

I've moved on from self sadism to Big Brother. Channel a person older and wiser than you, who wants to help you, and will review your plan. I think one key is to get your ego out of the evaluation of the plan and it's effects. Anyone else's problems are easy to solve, it's only our own problems that we're morons about, because they're so tied up in our egos and self image.

Naturally, doing this with a real "Big Brother" would be better still. Having people you trust and can talk to is a good thing. Our own perspectives are quite limited, and particularly distorted when it comes to ourselves.

For me "strawmanning" means responding to a position which is imagined or made up -- as opposed to responding to the person's actual position. So if your plan really was complex, then (by my definition) you weren't really strawmanning yourself.

Of course you are free to define "strawmanning" any way you like but I think my definition is the more commonly used and accepted one.

Wouldn't it be easier to just write down and then assess/ameleriorate the biggest weaknesses in your plans?

This is going to be extremely hard for anyone with difficulty with negative self-concepts to do well; the negativity could be extremely demotivating.

I'd suggest extending it by writing every separate statement down on an index card. Take the index cards at the end that are just negative (like "it's arrogant you think you can write a book" below) and burn them. Literally.

Then take the index cards where your internal less wrong commenter has a point, and do what they say. ("You'll never be finished in two months if you haven't started yet" is an example from the book case below that might be productive.)

The catharsis of burning the pure negativity will be helpful in preventing you from lapsing into a negative affect spiral about yourself, and then you'll get the benefits of this technique, which I think has a lot of potential.

Anyone who comments on Less Wrong knows it's much easier to tear something apart in comments than it is to write a good post. This is just a neat hack on top of that.

For instance, I recently came up with a complex plan to achieve one of my goals. Then I strawmanned myself; the strawman version of why this plan would fail was simply "large and complicated plans don't work." I thought about that for a moment, concluded "yep, large and complicated plans don't work," and came up with a simple, elegant plan to achieve the same ends.

You even mention an example and then still fail to actually give it. That annoyed me because it would have been nice to see this abstract idea grounded.

In many cases, the obvious uncharitable insulting argument will still be fundamentally correct.

Is this intended to be an empirical claim?

This is an excellent idea and a necessary step in just about anything important you're going to present to the public. You do need to anticipate objections, even if you don't answer them right there in your original presentation. And yes, this is a great way to make your plans more robust on a deeper level.