How to use money for accountability in a way that is neither unethical nor self-defeating

It's that easy!

Here are two ways I’ve heard of people using money to stick to deadlines. They pledge that if they miss the deadline they will:

1. Donate money to an “anti-charity”, i.e. a charity or advocacy group that is making the world worse, like the Society for Taunting Children.

2. Donate money to an effective charity. For example, the Against Malaria Foundation, GiveDirectly, or the Humane League.¹

The anti-charity technique is ethically perverse. There’s a risk you will have to pay out; and thus you are exposing little children to a risk of being taunted, just to make yourself write faster. The children did not sign up to stake their safety on your productivity scheme. It’s wrong to expose people to risk of harm without good reason, and your productivity is certainly not a good enough reason.

The effective charity technique is morally permissible, but self-defeating and counterproductive. How exactly is the “risk” of donating to charity supposed to be motivating? With this incentive structure, procrastination is now even more compelling. Procrastination now offers a two-for-one special: instead of formatting your boring paper, you can do something that’s more pleasant (watch a dozen I Think You Should Leave sketches) and better for the world (pay up and protect children from malaria). I’ve never understood why people do this.

So, you don’t want to pledge money to very bad causes or to very good causes. Instead, consider using a risk that’s motivating but morally neutral: the risk of your friends having my money instead of you.

Odysseus could have instead promised to pay each of his shipmates five oxen

Here’s how I use this technique. I can Venmo someone money, and in the memo line I say what it’s for (“draft submitted by 5pm this Saturday”). Then I request the money back if and when I’ve done the task and proved that I’ve done it. The advantage of pre-paying is that the other person doesn’t have to remember to follow up to get the money out of you. The pre-payment makes it more likely that you could actually lose the money, and it makes it easier for the other person. Other times pre-payment is not necessary, and just sending a text with the promise will do the trick.

One advantage of money-based deadlines is that, like betting in general, it helps to reveal what you really believe. Do you really believe you can write 5,000 words today? Would you stake $25 on it? Once you have to put money on the line, you may realize that you were kidding yourselves. A “bet is a tax on bullshit”, and we are all bullshitters about deadlines.

What amount? I haven’t experimented with this, but I wouldn’t be surprised if the amount scales in weird ways. I think having to pay $1 is probably not that different from $10, since the sheer annoyance of paying at all is a big part of it. I usually avoid pledging above $50 because as the amount goes up, I worry that I might be motivated to try to weasel out of the deadline.

Does this technique require having a ton of expendable money? What if you don’t have much money to spare? I don’t think this technique actually depends on having lots of money, and I’ve used it both when relatively rich and relatively cash-strapped. You do need some spare money – this is a tool for the privileged, to be sure. But you don’t need loads – when you have less money, pledging lower amounts can be equally motivating as large amounts when you’re flush.

One downside of this technique is that your friends might find you eccentric and annoying. But your friends should chill - you are giving them the chance to earn money for free. As friend-of-the-blog Neel Nanda once told me when I texted him with a money-based writing deadline: “Hype! I love expected value.”

1. While this option is much better than the anti-charity option, and I think is morally fine (albeit counterproductive), I can imagine a moral case against one as well. It seems to be somehow disrespectful or inapt to tie something important like children from malaria with something trivial like your inability to resist playing online chess.