I've been writing a blog for a long time, and I think the articles that actually get posted tend to be decent. Unfortunately, I have a lot of articles that never make it past the draft (or even outlining) stages. It seems like once I get past a certain level of complexity I just get lost. I have trouble deciding how to structure posts (or whether I should split them into a series), and I'm terrible at writing introductions and conclusions. I'm also not particularly good at headlines, although I consider this a less-important problem.

Are there good articles / books / classes on how to do this, ideally with well-chosen practice ("Outline articles on these topics", "Write an article on this topic", "Write an introduction for this post?", etc)? I would be willing to pay money for this if it's good enough, especially if I had access to someone who could review my work and give suggestions.

I assume one method of doing this is "practice until you get good at it". I've occasionally just forced myself to write something and then post it, but I almost always end up deleting these posts because they're not up to my standards, and I feel like they don't count as "deliberate practice" because I can tell that something is wrong with them but I don't have the experience to know what it is.

I've been looking through SkillShare and other things I've found via searches, but they also seem to skip over the "actually writing an article" step and focus on things I don't need help with, like:

  • I don't need to setup my blog (I already have one)
  • I don't need help with SEO
  • I don't care about monetization right now
  • I already have ideas for articles

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Franklin had a pretty interesting way of improving his writing, which can be generalized. He would read articles that he liked, and then try to rewrite them from memory. That way he could compare what he wrote with the original - which creates a very clear feedback channel.

By comparing your choices with those of an experienced writer, you hone in on exactly where your mental model of writing needs improving. Depending on what you need to improve you can tweak Franklins model. You mention structural problems: to improve you could try to outline good blog posts from memory, and compare what your outline with the original. Where is your pacing off? How many examples do they use? Do you lose the thread? By comparing what you do to the original the nature of your problem will become much more clear, and you will have begun forming deeper, more detailed mental models of how to structure a blog post. You will start to notice classes of openings, different structural principles, etc.

You could approach headlines similarly. Ask a friend to email you sections of blog posts, and give them the best names you can think of. Then look at the original. Try to analyze why the original is better, and try to tease out how the author approaches headlines.

Thanks, this is a great idea!

1Henrik Karlsson3y
It'd be good to know if the strategy works for you, so if you try it, please let me know.

If you want feedback on your blog then there are four options:

  1. You can review the work yourself.
  2. You can publish it online and read the comments.
  3. You can join a group where writers share drafts with each other.
  4. You can hire someone to read your work.

#1 only works if you can figure out what is wrong, which you can't. Besides, you already have published 50 posts on your blog (and written who-knows-how-many drafts) over many years without making progress. #2 tells you useful information but not how to structure a post. #3 might or might not fix your problem. Not everyone's personality is suitable for writing groups. #4 makes sense if you have money and can find the right teacher.

I have trouble deciding how to structure posts (or whether I should split them into a series), and I'm terrible at writing introductions and conclusions. I'm also not particularly good at headlines, although I consider this a less-important problem.

I read the five most recent posts on your blog. Your self-assessment is correct. Your posts do have structural problems. Your introductions and conclusions are terrible. Your headlines aren't great either. These issues mostly stem from your posts' lack of a clear objective.

I have lots of experience teaching things and I am available for hire. If you would like to hire me to help you learn how to write better then PM me and maybe we can work something out.

Thanks for the in-depth feedback! Your points make sense to me, and I think you're right that I probably need to join a workshopping group or hire someone. Publishing and reading comments would probably work (seems like the way most people do it) but the feedback loop is just too long.

Something I'm realizing from your comments is that I need to decide what type of article I'm writing and then structure it based on that. I think I've avoided the "list of n things" because it feels Buzzfeed-y, but I should probably embrace it when that's the kind of article ... (read more)

I took this course by Venkat Rao and Sarah Perry and it is really great:


The Writing Well Handbook by Julian Shapiro seems solid. I've only skimmed through it, but in skimming it looks solid, and I thought his growth marketing guide was really good.

Here's a video of Larry McEnerney from UChicago teaching about how to make your writing more valuable to the reader: https://www.youtube.com/watch?v=vtIzMaLkCaM

Normally, I don't watch videos when I want to learn something, but this one made a big impression on me. I've found the advice it offers at just the right level--not too low to lose sight of the big picture, but also not too high and abstract to confuse me. The gist of his message is to write with the reader in mind. The video offers advice how to do it, focusing specifically on text structure, which may be your biggest problem now.

Edit: Here's a link to the handout that goes with the class: https://cpb-us-w2.wpmucdn.com/u.osu.edu/dist/5/7046/files/2014/10/UnivChic_WritingProg-1grt232.pdf

[+][comment deleted]2y1
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This highlights a whole class of questions around education on navigating the realities of modern online job and relationship stuff.

Can you go into more detail about this? I'm not sure what you mean.

Is it possible to teach people good heuristics for managing their online presence or does the underlying territory change too fast even for general heuristics? I'll give a concrete example with serious consequences: several people I have talked to about online job searches didn't know about the automated resume screening that large platforms use and thus the need to optimize the resume using the appropriate tools/checklist/domain knowledge.