Why do essay collection books suck?

Looking for some insights.

As work is underway for a collected works book of sorts, we’re trying hard to avoid the obvious traps. Most books that are collections of blog posts or articles don’t work very well. They’re under-loved, under-designed, and don’t make for very good reads.

If you’ve ever purchased a collected works type book, what are some of your frustrations? Or what things did you wish the author/editor/designer did that they didn’t do?

We have our list but want to hear yours. Thanks.

32 Responses to “Why do essay collection books suck?”

  1. Brian Willis

    I felt this way about Paul Graham’s “Hackers and Painters”. Taken on their own, each essay is well written and thoughtful. However, as a book it’s pretty incoherent, bouncing from topic to topic with no central theme. So tie it together somehow. The book should flow from one chapter to the next in a sensible way.

    Only write an introduction chapter if you can add some value through it. Don’t write 10 pages of fluff just because your publisher tells you that you should.

  2. Scott Berkun


    Absolutely – this is a common problem.

    The challenge is the pieces themselves weren’t written to go together.

    The patchwork solution is to ask the writer to introduce each piece, but that makes it worse, in the same way prefaces to books ruin them. They try to pre-explain things which can’t possibly work.

    I recently read a collection of Chuck Klosterman’s writings, and the introductions make the book progressively harder (for me) to read so I skipped them.

  3. Dorian Taylor

    A: Because I already read it on the web (cough Paul Graham ;) .

    gah beaten to it

    1. Scott Berkun

      Dorian: there is something different about reading things on the web one at a time vs. reading them in one long sitting. Even if I’ve some/many of the pieces before, if they’re organized right and edited well I’d be ok reading them again in another format, provided I knew that’s what I was getting.

      That’s the theory anyway. Some collections I’ve read live up to this, but most don’t. I thought I should ask readers why :)

  4. Ross Johnston

    I just finished Being Geek by Michael Lopp, and while I found some great nuggets, I found the overall experience a bit of a slog. I think the main problem was the lack of a traditional story arc. There was some order, but I can’t say I would have noticed it had I not read the introduction and chapter organisation at the front. The pieces just weren’t written to go together and it showed. I’m not sure there’s any way around that.

    But as you say, maybe the best approach is setting clear expectations up front.

    Or make the book relatively short to offset the lack of a strong, engaging story arc?

  5. Thomas "Duffbert" Duff

    One of the books I gave a single star review to on Amazon was a “collected essays” book. The title of my review was “Well, those are five hours of my life I’ll never get back…”

    The problem with that one was that analogies and illustrations that are appropriate over a five to ten year period when reused appear as an obsession when you get them repeatedly every 10 pages. You start to wonder if the author has only seen one movie in their life, and everything they write relates to that. :)

    He said I did the book a disservice by reading it all in a single sitting, and that it was meant to be read in smaller chunks and “contemplated.” My feeling was that if you need to tell me how to read your book, then there’s a major problem.

    This isn’t to say that I dislike all compilations, but they do have some inherent difficulties that are hard to overcome.

  6. Sean

    I’m not really a fan of Paul Graham, so I haven’t read his books, but I do have to repeat the “already read it” complaint about this type of book in general. If it’s a topic I’m interested in, if the authors are well known in their field and if the essays have previously been published online, I’ve probably already read them. If it’s *not* a topic I’m interested in, I probably won’t buy a book about it. So that leaves you with trying to find unknown authors (why are they unknown?) or unpublished pieces (a different type of book).

    Yes, it’s true, a collection can be greater than the sum of its parts, and reading them in that format could be a significantly different experience than reading individual posts over the course of a few years. However, in practice I find that I rarely get anything new out of re-reading essays in compilation form. Further, I have a queue of books much longer than I’ll ever get through (kind of like my Netflix queue…), so I have to budget my time very carefully. I’d rather spend that time reading something completely new than revisiting things I’ve already read in the hopes that I might get a new sliver of insight out of it. If I were retired and had unlimited time for reading, I might be more inclined to read collections of things I’ve already read, but right now it doesn’t seem like the wisest choice.

  7. Scott Berkun


    Good questions but I don’t have answers. Working on that.

    I can say I’ve read several collected works of Bertrand Russell. Some are excellent. I enjoy every piece, and even though they’re not written to go together, they flow well enough that I enjoy the experience.

    Some of his other collections thought are awful – disjointed, random, with no clarity about why certain pieces were chosen.

    Here’s a question: how is an essay collection better or worse than a greatest hits CD? Don’t they share the same challenge?

  8. Ross Johnston

    I don’t think I would re-read an essay in the same way I would listen to a piece of music over and over. So I don’t think that comparison is apples to apples.

    I think the same problem (with greatest hits CDs) exists, but that it’s just not as big a deal because people listen to music in many different contexts – doing other things etc. When you read a book it’s usually all you’re doing, and for most people, it’s read only once. So the lack of cohesion is a much bigger deal.

    I guess it depends on your goal – do you want to build your reputation and audience by exposing more people to some of your finer work – whet their appetite so to speak, or do you want to produce a collection that stands on it’s own and provides value even to those people who are already familiar with your greatness ;-)

    If the goal is just to raise awareness, then the lack of cohesion between the pieces is less of an issue.

  9. Thomas "Duffbert" Duff

    Interesting comparison between compilation of essays and “greatest hits” CDs…

    Could it be that songs are truly “hits” and there are not many of them (compared to the time spent writing an article), where an essay compilation doesn’t have the same measuring stick? It’s often “everything between dates X and Y” or “the stuff I really liked that I wrote on my blog over 10 years”.

  10. Sean

    I don’t think the greatest hits analogy is quite right. It’s very common for people to re-listen to the same music over and over and over again. Most people read articles, books or essays once. Also, reading requires full attention, so I set the bar for my reading material much higher than my bar for music. I listen to music while I’m doing other things, so it’s not a complete waste of time if I don’t get anything out of it. If I read something I don’t get anything out of, the time is 100% wasted. Finally, greatest hits CDs offer a way for people who don’t own any of the artist’s work to get the highlights without having to buy 10 CDs. For web articles, it’s very easy to get the highlights of an author’s writing from the original source, for free, sometimes with more value (comments, videos, links, etc. that won’t be in the book).

  11. Dan

    I bought Being Geek by Michael Lopp recently. It’s probably the only book I own that is collected from blog posts. To be fair, it’s not all blog posts. He did write some original content too, but because I am a regular reader of his blog, I definitely did recognize a lot.

    The book is pretty well organized and easy to read. I felt I could pick it up and set it down at my own pace.

    The one thing I wish Lopp had done was give more specific examples with certain situations. I’m the kind of person who learns well by being walked through examples. I can understand why he might not have done that. He probably feels it’s better for his readers to come up with solutions that fit their own needs instead of parroting his words/actions.

    Another book that is worth looking at from a design/readability standpoint is How To Be A Graphic Designer Without Losing Your Soul by Adrian Shaughnessy. It’s really a collection of interviews with other designers talking about all the things that are maddening about relationships with clients and how to avoid common pitfalls.

    The first edition had examples of work produced by the designers who were interviewed which helped lend some context. The second edition removes that and updates the interviews almost completely as not all of the same designers are interviewed.

    The reason I am pointing this book out, even though it’s not technically a collection of blog posts, is because I liked the premise but I found the layout really difficult. He used a sans serif font with a small x-height against a baseline that had double the leading. Talk about eyestrain! I felt like I was just plodding and struggling my way through paragraph by paragraph.

    From an aesthetic point of view, the book looks lovely, but in practical terms, it was a total PITA to read. I think the book could have worked better as a series of radio interviews. I would have felt more engaged with the content in that context.

  12. Scott Berkun

    Sean: You’re right, not a fair comparison. But some challenges are similiar. The order of songs for one. Also the false promise of “unreleased blah blah blah” which usually sucks.

    Then there’s also the George Lucas effect of remastering/re releasing the same thing with some gimmicky element that’s almost compelling but not really.

  13. Thomas "Duffbert" Duff

    One thing that makes a difference with compilations for me is whether I’ve read the person’s work before. With Being Geek, I was a new reader to all the content, so it was interesting to me as new material. But if I’ve read a person’s blog or whatever that has most of the source material, then it’s far less “unique” and compelling…

  14. Scott Berkun


    You make a good point. Target audience is important – fans are one audience, new readers are another. Both are generally attracted to collected works type books.

  15. Michael Gaigg

    Scott, ask yourself why you are publishing a book with your essays in the first place… I mean, what is the advantage of having a book (and paying for it) over simply parsing through a list of links (that your readers probably already know) online? Ask for who you are writing it for and what this audience would benefit the most from.

    – Should you leave space on the side for notes?
    – Should you write little abstracts upfront?
    – Should you add content (“paid content” so-to-say) that readers wouldn’t see online?

    I personally care about the content and the author, couldn’t care less about the flow, order, fancy illustrations, etc.

    Two books I love which are collections of essays are Umberto Eco (How to travel with a Salmon) and Peter Drucker (Essential Drucker) – both without fanciness and ‘experience’ – but I don’t regret a dime buying them.

  16. Sean Crawford

    Thanks Gaigg, I’ll have to read Eco. As for Drucker, I too will read a compilation. While some folks would say that essays are a read-once, i have often re-read Drucker, not just because Drucker’s stuff is to be learned over time, not swiftly taught, but also because, like Orwell, I feel am a better man while reading him because of his tone.

    For my part, if the essays are exciting then I feel a sense of loss, of going against my better judgement, whenever I go straight onto the next one without time no contemplate. It’s like how I feel if I web surf or TV channel flip. It’s like what Scott said about certain conferences: it’s sure exciting but he misses out on learning if he doesn’t have down time between sessions.

    Here’s a brainstorm thought: I suppose some readers might slow down if there was Asian art between essays, the way some manga readers learn to look at the art before being tempted to surf the plot/word balloons.

  17. Sarath

    You said it right. Recently I purchased the books Being Geek by Micheal Lopp. The content is really good but I’m not getting the flow. Usually the blogs are not really written for making as a book. Just random thoughts on various matters. They’ve tried their best to make the book organized but something is missing there. Also lot of frequent words making me bored like “gig”. The blog contents should not be copied as such unless it make some sense.

    But your essays can stay independent. the classic Mythical Manmonth is a collection of unrelated stories. But still we enjoy at it’s best.

  18. Scott Berkun

    A friend mentioned America’s Best essay’s series as a good example, and I agree. The 2007 edition (linked above) was particularly good.

    They have the additional challenge of mixing authors and genres into a single book.

    When I read collections like these, I find I don’t mind skipping essays I don’t enjoy, as they majority are so good. The fact they’re by different authors on different themes makes it easier to skip – it feels like a sampler pack.

  19. Phil Simon

    You didn’t like Klosterman’s IV, eh? The Britney essay alone made it a great read for me, but I understand your point.

  20. Chandra

    Exploratory Testing (https://www.amazon.com/exec/obidos/ASIN/0321636414/scottberkunco-20/ by James Whittaker contains his previous blogs (printed as it is).
    I would expect a brief summary of each blog and link to that blog (instead of complete blog – cut&pasted). If I am interested in that blog, I can go and read that online; there is no need to waste paper.

  21. Pablo Lopez

    Well, I have the ones from Joel Spolsky (The best software writing, more Joel on software, etc…) and they were fine. No complaints, although I had read most of them online. After all, you know what you are buying…

    I like the book format and I like being away from the computer when I read them. Although it is true that sometimes this is not the kind of literature you want to read when you want to relax or before going to bed because you kind of associate it to work :(

  22. Daniel H. (Germany)

    Having read the comments, I agree with the points mentioned so far.

    Something I can add:

    – Reading a blog is a nonlinear access to information for me. I find a post with an interesting caption / topic. If it lives up to the promise, I can either check the comments or look at similar posts (which are usually directly linked from the post). A blog usually features a vast amount of text (if you count all posts with all the comments) but offers the option for a reader to read selectively. On the other hand, reading a book is usually a linear experience (of course, every reader skips parts of the text and some books like goldman’s “the princess bride” even play with this behavior). While as a blog reader I’m pretty happy with reading 10% of a blog and skipping the rest, for a book I expect >80% of the material to be of interest to make it worth the read.

    – Alot of blog posts are of mediocre quality. Scott, I think you commented before on the question wether there is some kind of correlation between the quality of a text and the time the author spent with writing it. Because blogs provide no limit for the amount of text they can hold, they encourage the writer the write vast amounts of mediocre text. It’s fine for most readers since they can read selectively (see point mentioned above). I read some books made up from blog posts of rather successfull authors which were created during the author’s reading tours. They sucked because it was just alot of mediocre writing which was packed into a book because the text was already there and surely, people would buy it.
    On the other hand, there are alot of books made up of magazine columns from a specific writer which I really enjoyed reading. What made them much better is probably:
    – the different chapters all fit to an overall topic
    – there was a way better quality control for the text published in the newspaper / magazine. Not by the magazine itself but by the author because in this case, he’s not writing for himself (or a non-paying blog audience) but for a paying customer.

    What I’d like to see from your upcoming book:
    – No vast amounts of comments added to each post. If you want to add comments from readers, a nice way might be to include them in the text in little boxes with the main text wrapped around them (like the way quotes from the text are sometimes added to newspaper articles)
    – Improved / updated versions of the articles and assays. You already got alot of feedback on your work through comments – are there improvements for the original text?
    – A consistent flow of the text or a story through larger parts of the book. Use different posts or essays to show different points of one main topic or also, how your insight on some topics evolved over time.

    Sorry for the large post. I’m no native english speaker so usually it takes me many words to make a point.

  23. Rob Brock

    Unless a book promised me more than a simple collection of blog posts, I would pass it over on the shelf at the bookstore. What would add value for me would be two key elements: Structure and Depth.

    1. Structure. I’d be interested in a well organized collection of posts that offered to share secrets of building a business from the ground up. Collect your articles into sections around the business lifecycle: identify a need, understand your customer, formulate a concept, develop a product, communicate your value proposition, etc.

    2. Depth. When I read any blog, I expect a quick read with a kernel of an idea, a bite sized nugget of knowledge. When I read a book, I expect more in depth analysis, and a reasoned approach to both the idea and an exploration of the boundaries. More than that, I expect examples and stories that illustrate the concept and give it some proof.

    If you offer a clear structure, I might be interested in a simple collection of posts without additional content. If you offer depth, with additional content, I might be interested in a loose knit collection of topics. If you offer both, and do them well, with a clearly communicated value proposition, I’d probably pre-order the book.

  24. Stephen James

    Timelessness has to be there. If it’s a book I’m buying (or checking out of a library), then the topic has to be timeless. The last thing I would want to get is an essay book on technology.

    The essays need to be written from a historical perspective with the frame of reference being “In the years 2000-2010,…” not “Last year,…). Use current issues as illustrations, but don’t make the focus of the entire essay on a problem that won’t be around in five years.

  25. Mike Nitabach

    Dunno if you are talking about a collection of the works of a single author, or an anthology. I really love the “Best {Sports/Science/Non-Fiction} Writing of Year” books, but I *never* read the introductions. No one gives a fuck how or why the editor chose the selections she did. I think collections from a single author tend to stink because those who are inclined to buy the book have already probably read most of the pieces, and thus feel ripped off.

  26. Mark Colburn

    [tl;dr — Readers expect you to provide a value beyond Google’s search result page. Search engines make finding data easy; but finding high value *information* is hard. Readers want information, and they are paying you to sift through the data, analyze it, organize it, and provide them with information in the form of conclusions, best practices, or organizational models that they can use to address problems that they face.]

    Why do essay books suck so much? I can think of four reasons:

    Many anthologies cover conflicting or overlapping problems or solutions, and it is left to the reader to sort out how to resolve the conflicts.

    The essays are usually initially written for a particular blog, journal, or conference with widely differing audiences and goals, and collected into a single work because they relate to a given topic area. The chances of all of the works being relevant decreases geometrically with the number of essays. Further, if I attended the conference or read the journal, or blog, I already have the original work.

    As a reader, I have to do a lot of work to adjust to each new work as I read through them. I need to adjust to their writing style, understand what they are trying to tell me, determine context and applicability, etc. That works for a set of short stories, because the varying writing styles enhance the entertainment value of each of the stories, context is created within each piece, and there isn’t any concern about addressing conflicts in story lines.

    Often essays present some new ideas to address existing issues, but there isn’t much (or sometimes any) data about long-term success or implications. What has happened between then and now to make this more or less applicable to the real world? This is even more of a problem with blog since knowledge, engagement, and perspective of the writers varies so much, and there is no factual rigor enforced.

    A few ideas that might address these shortcomings:

    Edit the works to apply a consistent (or at least relatively similar) narrative voice throughout the book.

    This approach could be problematic if you have a number of authors, and would require significantly more work from your editors.

    Research each essay and write a lead or trailer to cement each piece into a conceptual framework for the reader. Some questions that could be answered:

    * Why was this essay interesting?
    * What do you hope the reader takes away?
    * How does it relate to other pieces, or to your central premise?
    * How could the user apply the information?

    It’s kind of like “Tell them what you are going to tell them, tell them, tell them what you told them”. I’ve heard that’s not a bad idea when presenting information? :D

    The last two ideas would be a lot of work for the person who is editing the anthology (presumably you), but would make the book a much more compelling read. In essence, you are writing a book and using other people to provide examples for you.

    All of this is really just another way of saying:

    * Understand the needs of your audience
    * Give them something that they value

    In days of yore, anthologies were relevant because finding and curating high-value topical information was difficult. Now days there is Google*: the problem is no longer finding topical information, it’s being able to make sense of it, fit it together, and draw conclusions from it.

    Your value as the editor/author of the work has to go beyond the search results page. I think weaving an cohesive organizational framework that the essays fit into that provide background, support, or counterpoint to your overarching idea could make an anthology much more compelling.

    * There are rumors of other search engines out there. Substitute as you see fit.

  27. Keith Mingus

    Mark is hitting the needs of a book of essays.

    Each essay needs some context for the reader. Especially if your expecting they may read it from start to finish.

    When was it written? What question is the essay answering? How does it relate to other essays in the collection? Why was the essay chosen for inclusion? etc.

    A little blurb giving the essay some context gives the reader a break to ‘clear the palette’ between essays.

    Readers are use to a coherent linear narrative and a book of essays can be jarring to that expectation.


  28. Chris Hare

    As a reader the three things I’m looking for are:

    1) An engaging human voice
    2) Value
    3) And to Ross’ point a good story arc to carry me from start to finish

    If your content is difficult to stitch together in an arc that takes the reader from cover to cover, you might look at creating smaller narratives either section by section or chapter by chapter. While he’s probably never even seen a blog post (Technopoly and all that) Wendell Berry does a fabulous job in his essay compilation Bringing It to the Table of both telling great stories and engaging the reader with the one truth he’s trying to drive home through the emotional impact of those stories.

    Just because someone read an article on your blog in the past doesn’t mean they fully processed it. You can add value to that content with a fresh story or fresh application and you’ll have a better chance of delivering a book that people will be happy to read from cover to cover.

  29. Maxim

    I’m reading Design of Design by Fred Brooks.

    It’s a collection of essays written by Brooks. You can open it on any page and read from there. However if you read it from the beginning, there is logical order of essays where they seem to complete each other.

    Beautiful Teams on the other hand is a good book, but you never know what to expect and what kind of story you’ll get from next chapter. Probably not the best explanation. I guess it’s just because each story is so different in style. Some of them are essays (like yours there, liked it a lot) others seem to be an interview. And because they are so different in their approaches, at times it seems like someone printed out RSS feed.

  30. Luke Huggett

    The Four-Hour Body is essentially a collection of related essays. And, much of the information can be found on Tim Ferriss’s blog. I read the book cover-to-cover in 3 sittings. The content was so good/interesting that I couldn’t put it down. As long is every essay is really good on its own I believe that the book will also be good.

    What seems to make essay collections suck is having to sort through bad content to get to the interesting content.



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