How To Blog: Write Stuff That Matters + Reach Out To People Who Care

A 22-year old named Dan Shipper recently convinced me to subscribe to his blog. Technically, it was his writing that did the convincing. It helped that people were sharing it all over my Twitter feed. I found myself nodding my head so much that I typed in my email into the subscription box, and this was such a rare event for me that I had to try and make sense of it. What did he do right? Off the top of my head…

  1. He writes very, very clearly.
  2. He asks good questions.
  3. He uses simple, compelling case studies.
  4. He has real (and therefore interesting) experience from doing actual things.
  5. He doesn’t waste my time.

The first question on my mind was, “How long has he been writing?” Nobody becomes Seth Godin or Paul Graham overnight. I went straight to his blog archives. They date back to 2011, so he’s been blogging consistently for over 2 years. And sure enough, his earlier blogposts are significantly less compelling than his later ones.

Dan started out writing “alright” blogposts with a shaky hand, and he kept at it until he started writing blogposts that got him to the front page of Hacker News.

How could you do the same? Here’s my take:

1: Write stuff that matters.

(Absolutely nothing else counts if you don’t satisfy this condition.)

ZERG RUSH: Quantity is half the solution.

  • Blogpost No. 500 will kick blogpost No. 1’s sorry butt. Once you write that much, you’ll internalize a bunch of important things you didn’t even think to consider before. You’ll realize that some of your points were irrelevant or inconsequential. Knowing this, how can you even think of promoting post number #1? You haven’t even learnt why it sucks!
  • It’s actually very hard to write 500 lousy blogposts. Seriously, try it. Most people give up by post 20. By the time you’re at post 100, you’d probably have accidentally written something worth reading. Blogs are beautiful generators of happy accidents.

BOOM, HEADSHOT: Quality is the other half.

  • What pisses you off? Don’t just follow your “heart” or “passion”- there’s a good chance that the romance might fade. Find an region in idea-space that constantly annoys you with its vagueness and opacity, then light the bugger up. Identify the skills and tools you’ll need, acquire them, make it happen.
  • Use writing as a tool of exploration and seek to solve the problems that plague you. You’ll find that you’re not quite alone in the vast, uncaring universe- there are always others who share your pain. And if not, well… at least your head’s clearer for it!

 

2: Reach out to people who care.

  • You can’t just ask people to read your blogpost. Few things are as annoying as someone asking for a favor out of the blue. What’s in it for them? You have to make it worth their trouble. You have to have a real conversation. You have to ask them questions that they are interested in.
  • What would somebody else have to do to get your undivided attention and honest feedback? Do that. Make it very clear that you don’t want a feel-good pat on the back, you want a kick in the pants. Your mission requires it.

There are two benefits to this:

  1. Your writing will quickly suck less. This allows you to satisfy condition #1: Write Things That Matter.
  2. You’ll earn fans and supporters. Most of us are deprived of sincere human warmth and enthusiasm. The former is disarming, the latter is infectious. (Pay attention to the Likes people get on Facebook when they share stories of hard work and accomplishment. It’s one of the 3 great stories we love, next to stories of connection and stories of creative insight.)

 

That’s it, actually.

It’s a beautiful loop. Your writing gets better. People care more. Your writing gets better. More people care. Do this consistently for two years, and your blogposts will be the stuff of legends.

That’s all it takes.

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