Blogging Workshop Notes

This week, at Artsy’s offsite, Orta and I are leading a workshop named “Bootstrap your Blog!” where we’ll try to get participants most of the way towards their first blog post. This advice is widely applicable, so I thought I’d share it here.

Here’s the introductory email we sent participants.

Hello team! Orta and I are super-excited you’re coming to our “Bootstrap your Blog” workshop at Artsy’s offsite! Here’s a brief intro describing the workshop and a small bit of necessary preparation.

Our workshop’s goal is to get you most of the way towards writing your first blog post. We’ll be describing what a good blog post is, how to write one, and most importantly: how to recognize when to write a blog post.

You’ll need to bring an idea to blog about. This idea should be something you care about – the more you care, the easier it’ll be to blog. It can be related to Artsy, or not, as long as you care about it. Try to think of something you’ve recently learned, or were surprised by, and bring that idea with you.

We’re recommending you use pencil and paper, which suits the offsite a little better than computers. We’ll have materials, but you’re welcome to use a laptop or tablet if that’s more comfortable.

We’re really looking forward to this because we both believe in a world where everyone benefits when we all share our experiences. It’s exciting and rewarding to be there as you take your first steps into that world, but remember that the most important thing is that you enjoy yourself. Have fun!

The email is meant to be encouraging without applying too much pressure. People get caught up in the details of writing and that can be discouraging. Instead, I’ve tried to frame our introduction as a learning exercise so that making mistakes, or not completing a blog post, are totally acceptable. I write half blog posts all the time and they never get published, and that’s okay.

Here are the main points we’re going to cover in the actual workshop.

How to recognize when to blog?

  • Blogging is easiest and most effective when the blogger cares about the subject.
  • The more you care about the subject, the more you should blog about it.
  • If you learn something, if something wasn’t immediately obvious to you, if something surprised you, write down a few notes. You probably won’t remember this later, but these little things can turn out to be the most important part of your post.

What is a good blog post?

  • A good blog post is usually short, even a few paragraphs can be effective.
  • A good blog post usually tells a story. The better storytelling, the better the blog post.
  • Blog posts, like all stories, usually follow the Hero’s Journey (and you’re the hero!). Here are 5 good steps for a blog post:
    1. The Ordinary World
    2. The Call to Adventure
    3. The Ordeal
    4. The Reward
    5. The Return
  • The story your blog posts should tell is your story. Since you’re the best person to tell your story, don’t worry about blogging something that another blogger has already discussed.

How to start writing a post?

  • Start with a stream of consciousness process. Either:
    • Stream an outline of the story and fill in details later.
    • Stream a story and organize it later.
  • Starting is the hardest part.

Miscellaneous advice

  • Worry about where to put it, formatting, etc last.
  • As a medium, blogs are not printed on paper. They exist on the web, and can be corrected. Don’t worry too much about publishing something less than perfect.
  • Orta and I can help you get set up putting your blog post online when we get back to New York. Just worry about the content :)

And that’s it! Remember to relax, take it easy, and remember: your blog doesn’t need to be perfect, it just needs to be yours.


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