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

It's that easy!

Here are two common ways people use money to enforce deadlines:

1. Anti-charity: if you miss your deadline, donate to a cause you detest, like the Society for Mocking Small Children.

2. Effective charity: pay your penalty to an effective charity, like 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 so you are exposing little children to a risk of being mocked, just to make yourself write faster. The children did not sign up to stake their safety on your productivity schemes. It’s wrong to expose people to risk of harm without good reason, and your battle against procrastination is not a good enough reason.

The effective charity technique is morally permissible, but self-defeating and counterproductive. How is the “risk” of donating to charity supposed to be motivating? With that incentive structure, procrastination is now even more compelling. It’s 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 make the world a better place (pay to protect children from malaria). I’ve never understood why people do this.

So don’t pledge money to very bad or very good causes. Instead, choose a method that's motivating but ethically neutral: risk your friends getting your money.

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

Here’s how I use the 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 I just send a text with a promise. I now have a group chat with friends where we send each other money-based goals.

One advantage of money-based deadlines is that, like betting in general, it helps reveal what you really believe. Do you really believe you can write 5,000 words today? Would you stake $50 on it? Once you have to put money on the line, you may realize that you were kidding yourself. A “bet is a tax on bullshit”, and we are all perennial bullshitters about deadlines.

How much money is necessary? Small amounts can be surprisingly motivating; $5 might be nearly as effective as $15 since the annoyance of losing money matters more than the amount itself. I avoid pledging large sums because that could tempt me to cheat or bend the rules.

Does this technique require having lots of money to spare? What if you aren’t so fortunate? I don’t think this technique depends at all on having lots of money, and I’ve used it both when relatively rich and relatively cash-strapped. You do need some small amount of spare money – this is a tool for the privileged, to be sure. But you don’t need loads; you can adjust. Pledging lower amounts when you’re short on cash can be just as motivating as pledging larger amounts when you’re flush.

One downside of this technique is that your friends might find you eccentric and annoying. But they should relax - you are giving a chance of free money. 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. This option, unlike the anti-charity, seems perfectly morally fine (albeit counterproductive). That said, I can imagine one making a non-utilitarian moral case against this one as well. It seems to be somewhat disrespectful or inapt to tie something as important as saving children from malaria together with something as trivial as helping you resist the impulse to play online chess.