I'm Bad at Newslettering

Just terrible.

This past week my wife and I have been reviewing and trying to up our newsletter game for CourseCraft. Historically1, it’s mostly been a “we should let them know about new feature X/Y/Z” sort of situation, and we haven’t really taken advantage of the fact that we have a pretty big list of subscribers.

Doing some planning and initial work on that got me thinking — I also have a mailing list. If you’re subscribed you know this already, but I pretty much never send anything.

Self-doubt paralysis

Every time I’ve written a blog post or wrapped up a new side project over the past ~year since I started my newsletter, I’ve gone through this ridiculous day-long-hand-wringing where I think to myself –

Should I send this to my list? I’m not sure if it’s any good, or relevant enough. What if they unsubscribe!?


Invariably, of course, I don't.

But why?

I think the problem comes down to the fact that I mostly write technical posts (like ‘Flux from Scratch’) that take a long time to put together. That’s a problem because:

  • I tend to make a lot of little tweaks over the next few days based on feedback and my own re-readings.
    Subscribers would get the garbage draft version!
  • Code highlighting in email…?
    Excuse me while I shave this yak.
  • They seem to have a limited audience — using a specific technology, or solving a very nichey problem, or only of interest to Rails developers, etc.
    What if the subscribers don’t care!?
  • I’m super self-conscious that it’s not useful/impressive enough.
    The subscribers will surely think I suck!

Slapping out of it

It’s silly, though. I should stop doing that. Both things — second guessing myself and writing content that is too technical or too nichey.

So it’s time to refocus this blog. More writing on topics around bootstrapping products, remote work, and the like. Perhaps more people will give my hopefully-not-so-quiet-anymore newsletter a shot since the writing should have a wider appeal, and I’ll be less resistant to actually sending stuff to them.

Now the question is… should I send this post to my list?!

  1. I do feel like a 4 year old bootstrapped startup can have ‘history’ :)