Why I’ll Be Writing Every Day For Two Years

“Are you kidding me? I’ve been telling everybody that you write a blog post every single day!”

Sebastian just learned that I fell off of my writing-every-single-day habit, and became outraged. One thing led to another, and before you know it, we’d shaken hands and a bet was made. Both of us will be writing a blog post every single day for the next two years. I can say that with certainty, because we’ve also bet $10,000 on it.

There are some bets you make because you think that you have an advantage and you can exploit it to make money. This isn’t one of those bets. Writing every day for two years is incredibly hard, and I don’t think that I have an advantage over Sebastian. He’s just as likely to be able to complete this as I am.

I’m willing to make this bet because it puts me in a situation where I can’t fail. I’m not willing to lose $10,000, so my only other option is to succeed by writing every single day. Maybe there’s a 2% chance of something weird happening and me losing by accident, but if that’s true, than the expected value of this bet is a loss of only $200. In return for that, I get a 98% chance of having 730 blog posts in the can, and the improvements in my writing that go along with that.

The biggest benefit, maybe, is that I can avoid thinking about writing for the next two years. There’s no point in thinking about how much I don’t want to write or trying to come up with a justification for not writing. Those things are irrelevant, because giving in to them will cost me a large amount of money. The stress is erased, and I’ll just write.

There are a million ways to motivate yourself, but huge bets like this are a quick acceleration. I did the same thing back when I was into pickup– if I was chickening out and not approaching, I would hand my car keys to a friend and tell him the car was his if I didn’t approach a certain amount of groups. He would have kept it, too.

You don’t have to make giant bets, but it’s a tool worth keeping in your toolbox. By default people don’t really come up with strategies to stick to the things they want to do, meaning that most of them inevitably fall apart. Finding devices like this is a good practice to up your adherence.

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Photo is a secret passage from Dracula’s castle.

My writing gets a lot better when I’m writing every day and only posting the best two. I predict that within two weeks this effect will kick in.


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