Help me build the How To Think Sideways Surprise

I’m putting together the How To Think Sideways Surprise—the extra course material that everyone gets when they join the new version of How to Think Sideways, ULTRA.

(Legacy students and grads will upgrade automatically and for free—but you can still help build the Surprise.)

I want to make sure the Surprise is spectacular.

To make it great, I need to know this:

What part of writing do you find most difficult?

Anyone—even folks who aren’t considering joining the course, can comment here.

I’ll let you know what the HTTS Surprise is going to be in a week or two.

(And I’ll get back to writing soon. I’m still working from 7AM to midnight every day getting this put together—once it’s done, I’m back to Create A World Clinic. And Write A Book With Me will resume. Clearly I’m not a great pace rabbit anymore, though. :/)

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450 responses to “Help me build the How To Think Sideways Surprise”

  1. Sandra S Richardson Avatar
    Sandra S Richardson

    It’s a toss-up between actually writing and keeping in touch with my novel.

    I have a timeline. I’ve tried outlining and it did not work for me at all, but the timeline seemed to suit me well. Then, due to what ever reasons, my creativity on all levels has dried up. It got harder and harder to actually write because I simply had no words (for the story, not words in general) in my head to write. I had no artistic/craft ideas or urges either. VERY uncommon for me.

    Just this past week, I’ve started feeling nudges from the story, so I’m hoping the freeze is on the verge of thawing. I really do want to get my story written.

  2. Laura in Texas Avatar

    Reading through the comments above, I think mine are already covered: middles (coming up with enough “stuff” for people to do to tell the story) and the Butt in Chair issue.

  3. Pamela Avatar

    second guessing the “logic”… another version of perfectionism, I suppose. Writing the first draft I zip along following my hero wherever he leads. Then I sit down and think… “Wait…would they actually do this?” “Would xxx WORK this way?”
    I can niggle myself into a good fit of gray; fortunately I also climb back out. But I would love to know how to know the logic works before I get to that point.

  4. Grisselle Avatar

    One of the few things that I find hard is as my fellow commenters have stated, the middle of a storyline. This gets me all the time. The beginning is awesome just as it is the end, but the middle is what gets me. Also another issue I have is descriptions. I have the worst time trying to describe surroundings. As I like to say, it looks very beautiful in my mind, the issue is putting it in writing! Also because I’m bilingual, what I would know in spanish is hard to translate it to the english language.

  5. Elizabeth Avatar

    1. The Middle (mid-life crisis, I suppose)
    Big events are easy to set into place, it’s figuring out the transitional material to keep the pacing strong that challenges me.

    2. The Very Beginning (a very good place to start?)
    Capturing interest from the opening without creating an artificial crisis is driving me insane (more insane). I want to effectively draw a reader into the world of the story from page one.

  6. Rhonda Avatar

    The hardest part for me is having my dialog flow. I have enough narrative and back story to fill tons of pages, but when it comes to the dialog, I really struggle. I know what I want the characters to say, its just getting their words right and not having it sound boring is where I get stuck.

  7. Kathryn Carson Avatar
    Kathryn Carson

    Revising. When I’ve finished a novel, I feel as if I’ve actually written two novels: the one I see, and the one everyone else reads. The two look nothing like each other. And yet I somehow have to envision and correctly revise this shadow novel, when I have no idea what it looks like.

  8. Kit Avatar

    Primarily my issues are what happens during the revision process. Doubt (is the story good, I can’t tell anymore) and then I question EVERYTHING, because I’ve learned over the years that what I like in a story, about 99% of the people around me don’t like. Ultimately, the revision process ends up affecting my discipline because I honestly don’t enjoy doing them and my inner critic is a beast! What I have learned from the HTTS course and on my own, is that I would much rather spend more time writing from an outlined and well thought first draft then go through the nightmare of what I’m doing now on my first novel.

  9. Rob Avatar

    My problem has been simple, and stalls my plotting and character development. I never feel that I know enough to believe the story is ‘right’.
    I started the book I’m working on 13 years ago – and, after 4 years of struggling, decided to put it off ‘until I knew more’. Whether it’s understanding social politics, how to make charcoal, what the weather is like at altitude, or the ecology of swamps – there are a thousand ways, when I come to write a scene or understand a character’s experience; and thus, outlook, that I feel that my world and characters lack the depth and texture of a believable reality.
    I’ve never been comfortable with the answer “just because” to a question, and whilst I know I don’t need much more than a word-sketch to carry readers through the journey, that IS what I feel I’m saying when I don’t know enough about what I’m writing about.

  10. ReBecca Avatar

    Rewriting is the hard part for me. I’m a pantser, but I’ve used a lot of your exercises to keep my stories on track as I write them, so they’re in pretty good shape by the time I’m done. Not a lot of tangents. But still, there is so much to pull together all at once, it gets really overwhelming to rewrite. I’d love to find a way to rewrite that utilizes my pantser strengths. I’ve taken the full HTRYN, and it had a lot of great material, but it really overwhelmed me. I had a massive shut down from detail overload, and it’s been hard to get back on track with rewriting. I think most of it came from pushing my muse too hard, and trying to force a system that isn’t adjusted to my strengths. I’ve never finished a rewrite, so I’m not sure what will work best for me, and most courses on how to rewrite are written by outliners and have not been helpful.

  11. donna rae Avatar
    donna rae

    The hardest part for me is the revision. I have several
    first drafts but seem to lose interest once that is done.
    I have plenty of ideas but tend to procrastinate in completing what needs completing.

  12. Jenn Avatar

    1. Middles. Middles always stump me. I either blank out, or I come up with fifty different ways the story can go and can’t figure out which would be best.

    2. Staying on track. I’m always getting new story ideas, and I don’t know how to stay focused on the story I’m currently writing. Ignoring the other idea doesn’t work, but if I take notes suddenly I’m zooming off on that story and leaving my first one behind.

    3. Description. I’m not a fan of long descriptions, so my writing is pretty skimpy on it, and I know it gets confusing for readers.

    4. Recapturing what I saw in my head. I’ll come up with a great scene, and run through it in my head and everything works perfectly. But when I try to write it out, it falls to pieces. Characters say and do the wrong things, or I can’t recapture the emotion I felt when I ran through it in my head.

  13. Rex Avatar

    After the first rush of writing, and before the final polish, lies the quicksand of “things that do not fit.” Things happen without the narrator being there, subplots take off in new directions, and people change. I get lost and can’t find my way home.

  14. Brenda Guest Avatar
    Brenda Guest

    I find revision the hardest.
    It can feel like it will never be good enough and sometimes I change one part only to find things unravelling from there.

  15. Stephanie Black Avatar

    The hardest part of writing for me is remaining authentic in emotionally intense scenes and not censoring my true voice.

  16. Lynda Miller Avatar
    Lynda Miller

    Putting the story in the 1,2,3 moment or beginning, middle and end. Outlines are difficult for me otherwise I would have made.

  17. D. X. Logan Avatar

    With limited space and two active children, finding time and space to properly focus has been my biggest hurdle. It’s been made scene harder by the death of my laptop, though at least that is temporary. Staying on task and tuning out distractions has really been my major handicap.

  18. tyrone guess Avatar
    tyrone guess

    The hard part for me is trying to get every word just right. My internal editor is a Beast and will stand for nothing less than perfection.

  19. M. D. Wiliams Avatar
    M. D. Wiliams

    Picking up where I left off the day or night before…

  20. Bill Avatar

    I don’t seem to be able to get into the planning process at all. I have GENERAL ideas about what a character is like, but I just can’t seem to get down to ONE MAIN GOAL.

    This means that I never get past something like “My protagonist is a middle-aged husband with two late-teens children who is strictly conservative and has a great fear of losing ANYTHING that he thinks of as belonging to him.” And obviously, you can’t make a story out of something as general as that.

  21. S.J. Driscoll Avatar

    It’s hardest to make main characters come as alive as secondary characters.

    This may happen because the main characters carry the plot and can suffer from being plot puppets.

    Plotting has been my weak point. Now that I’ve learned to plot, I tend to have a death-grip focus on it to the detriment of the major characters.

    I can loosen up while writing less important characters and let them be who they want to be instead of who they have to be.

    This isn’t only a problem with some of my work. I’ve noticed it in many other people’s manuscripts and in many published novels.

    I might try writing a first draft from the POV of a narrator. That way, all characters would become secondary. It would be a clumsy fix since POV would have to be changed on revision, but it would probably work.

  22. Megan Avatar

    Honestly, the hardest part of writing for me is psyching myself out. I come up with an idea that I think is so fantastic, I build on it, I love it… And then, I think it’s dumb and no one will ever like it. So I push on and keep going with the work, but you can tell exactly where I started getting scared because my writing starts mimicking favorite authors instead of my own voice.

  23. Jass Avatar

    The hardest part for me is to get the words flowing without my internal editor sniping at every word I write.

  24. Ken Axel Avatar
    Ken Axel

    For me…just a second, I need to empty the dishwasher…I know the thing that…hold on, just got an email about some amazing offer…anyway, the hardest thing for me has…oops, just let me reply to this txt msg…as I was saying, the hardest thing for me has to be DISTRACTIONS!

    1. tyrone guess Avatar
      tyrone guess

      I totally…(pen fell on the floor…ooh, a bird landed on the window sill…) agree!

  25. Emma Avatar

    Two parts, one is the middle trying to join the beginning up to the end ๐Ÿ™‚

    Two trying to describe my worlds without over doing the detail, I can’t mentally visualise my worlds (dream vividly yes, visualise whilst I’m awake no, my mind can’t let go and I don’t know how to get round the block) So I overdo the detail ๐Ÿ™‚

  26. Sallie Avatar

    I think everyone has covered anything I can think of … Glad you’re still in there helping as well as doing your own writing.

  27. Esther Avatar

    Daily discipline. Momentum. Basically, just doing it.

    I have a few completed novels that need major revision (one I partly revised by having gone through half of your absolutely amazing HTRYN course), a couple of uncompleted novels, and one that I mostly completed in my head, but haven’t yet written any of it down. I keep dancing around my heart’s desire (to write novels) and doing everything else connected to writing, i.e. proofreading, copy-editing, editing, journalism, translation….basically doing all kinds of writing except that which I really feel I was meant to do: write novels.

    My experience sounds very similar to many of the other comments posted here.

  28. Lisa Avatar

    I think this is a great and helpful question, and I can see by the responses that folks have many different stumbling points. The problem I have, well, I’m not sure it can be addressed but if you have any good advice Holly (as you always do), I’ll take it. My problem is that I have difficulty feeling confident that what I’m doing is interesting. I 99% of the time later get told that it is, but when I’m writing, I don’t know. Does that just come with time, or is it an eternal curse?

  29. Jerome Kiel Avatar
    Jerome Kiel

    For years, I drifted along with being able to set down some thoughts on paper, which I believed were poetic. I joined a writer’s group and found I could write longer things, with care. Then, as a mature student, I studied Creative Writing with the UK’s Open University, where studying is largely done at home, with assignments which had to be prepared to a deadline. I learned – and experienced – a lot, not least to be more patient with my output, drafting and redrafting a piece of writing, sometimes up to nine times so that it read well. After four courses (four years), I decided to ‘fly by myself’, there having been no other courses suitable for me. I miss the discipline of assignments so, although I can create new work, the longer writing, like short stories is hard to develop. I wonder if ‘self-disciplin’ is everyone’s curse???

  30. Deb Avatar

    Plotting/outlining. I can start with what seems like a workable plan, then around the middle it all goes pear shaped and no longer seems to work. I fight with myself over whether to push on or start again and I can end up paralysing myself into not writing at all. It always seems to hit around the middle of the novel – so maybe I just have a problem with middles!

  31. Ellen Oliver Avatar
    Ellen Oliver

    Organization! When the characters are talking to me all at once, when the ideas have piled up – even though I have a place to put them now, organizing them into the greater whole so the work can rise to the next level is a challenge. I finally purchased a program for organization that works the way my mind does and that helped – a lot. But guess what? Coping mechanism level one in place, the words flow faster! So now I’m still spending what I consider precious writing time tracking things. I think I need to adjust my thinking and be thankful I’m in the flow, that’s it’s all just a step in the journey. And what a journey!

  32. Mary Reid Avatar
    Mary Reid

    Plotting is hard for me; I’m used to writing nonfiction. The other issue is keeping a consistent writing schedule.

    Thanks for all the help I’ve already gotten from your emails and course offerings. I’ll be buying and using a couple of your books!


    1. Jerome Kiel Avatar
      Jerome Kiel

      Yeah, non fiction drains the brains, it’s all REAL stuff and not from your imagination. I’ve studied Creative Writing, then went to Humanities, then back to CW, then on to English Language and its origins. It was hard to get back, IS, to more organic pieces, writing which I have learned to redraft carefully but with courage. You might benefit from ‘cultivating’ your imagination, with a notebook carried with you, recording ideas, phrases you’ve heard, bits of news, etc. Capture and harvest your sources for your imagination. There are other ideas, my obvious favourite (see other replies) is Cluster Diagrams like spider charts, good things to play with to see what ‘works’ for you. Use ’em for characters/plots/environment/place. Be patient with yourself. Read Julia Cameron’s ‘The Right To Write’.

  33. David Ferkins Avatar
    David Ferkins

    I have difficulty in descriptions. This happens when I try to describe characters, scene, action, etc. I am afraid of giving to much, not enough and/or even slowing the telling of the story down.

    1. Ellen Oliver Avatar
      Ellen Oliver

      Your descriptions help the reader into your story and to identify with it, to care about them. As a reader one of my pet peeves is lack of it, or not enough of it. I feel to get into the world the writer has provided, it is their detailed characters – as fully fleshed as possible with idiosyncrasies of speech, dress, personal hygiene, character flaws, whatever, that pull me there and keep me – or not. Think of it this way: without fully fleshed characters you’re basically in a world with no people, or worse, boring people or people you just can’t quite “get.” Would you stay there? You’re not giving the story away – you using them as your Voice to tell the story. So make that character so real you cry if they hurt. Then, let them loose. They’ll write the story for you. You’re still the Boss. Good Luck!

      1. Jerome Kiel Avatar
        Jerome Kiel

        I’m a great believer in, if you get stuck, that a spider diagram or a ‘cluster diagram’ where you start off with the central thing (character name in this case) and then add, or tag on, little balloons with other details, one each balloon. We think ‘organically’ rather than in ‘shopping lists’, in spite of what you may think, and in this way, you build up a group of details, little extra things which link with the person. If you play with it, for several separate characters, you can, of course, build up a group of characters, some of which you may not need. Then, get going with their interaction. Hey presto!

  34. Stacey McIntosh Avatar
    Stacey McIntosh

    I think the middle of a novel can at times be the hardest but also getting the right balance of detail. How much do you show and how much to leave up to the readers imagination.

  35. E. K. Carmel Avatar

    Dialogue. All the voices sound mostly the same, like me. And the conversations sometimes are stilted. I try to “get into the character’s heads” but have a really tough time with that. I understand their motivations, but I can’t seem to make that come out in their words and voices.

    1. Jerome Kiel Avatar
      Jerome Kiel

      Spider Diagram (cluster diagram)!

  36. Ryan Neely Avatar

    I think the hardest part for me is to let go of the search for perfection and just write. I find I spend too much time mired in the minutia of the details – trying to outline every last bit of plot and character – so that I never actually get any writing done.

    1. Ellen Oliver Avatar
      Ellen Oliver

      AKA Paralysis by Analysis! I get this disease from time to time -especially when I start to research things for a novel. Last night it was the Tango. I wanted a character to dance it – went online for music and to see the dance so I could describe it and got LOST in the music. But I also came out of it with even more ideas, which I scribbled as fast as I could. So now, I set an alarm – and keep it next to me – I use my phone – and when the allotted time expires I stop and get back to writing with the goal of writing at least one scene with the information. Hope this is useful for you.

  37. Judy Avatar

    Dialogue and emotion. I am normally a very shy person and grew up speaking when spoken to and have never broken the habit. I let other people do my arguments for me. I lurk around forums and never comment so this is a bit of a departure for me. I can write thousands of words of very interesting prose but when a conversation is needed to push the story along I stop dead. I have attempted five novels, all have beginnings, middles and endings but no emotion or conversation to give them depth.

    1. Jerome Kiel Avatar
      Jerome Kiel

      Prepare a cluster diagram with characteristics particular to each person, including how they speak. Listen to real people, eavesdrop of people in cafes, in shops, at the market and make mental notes on how they interact; make notes asap after you have done so.
      Then take a look at youtube’s versions of ‘poetry slam’, for example (!!!!!) the US’s Sarah Kay, who is emotional and fluid. Think about the ‘characters, they are ‘voices’ in your imagination, creatively speaking. See if you have a poetry/stand-up/speakeasy session in your area and go to listen. Soon, you may be able to dare yourself to write something you, yourself, can read out! Go for it!!! Everything you do will help your courage!!!

  38. Paul Humphreys Avatar
    Paul Humphreys

    My wife was not amused by my reply after she asked me if I had remembered to feed the dog. I was deep in writing at the time of her interruption. I simply replied that I was not aware that we had a dog. It took me about three days to recover my writing from where I left off. I love both my wife and my dog. And my writing. So, interruption gets my vote here.

  39. Jackie Kowalczyk Avatar
    Jackie Kowalczyk

    Hands down, the hardest part is the 300 word pitch or back cover blurb. Give me a novel to write anyday, but summarising it in a way that will make people actually want to read my book, that’s incredibly hard.
    for the same reasons, I also struggled with the three sentences I ended up using in my ‘About the Author’ section.

  40. Wendy (estuary) Avatar
    Wendy (estuary)

    Not to sound happy for the long list of difficulties here, but it’s a little heartening to read the variety and persistence of the problems we’re all facing. I tend to think I’m just not able to overcome my molehills and the rest of the world is expertly capable and sailing right along…

    Currently, maintaining momentum through the middle is my weak point. (Thus, I don’t have a clue how I’d handle an ending, so first things first). I keep stalling out in the middle of things, unable to tell what’s necessary, what’s superfluous and honestly, how to get my characters to Not Be Me (as in, even if I stall out in the middle, THEY don’t and they keep the story going). Second-guessing leaves me uncertain about my tangle of themes and possibilities and that makes it far too easy to set the project aside.

    Having set it aside again and again, I’d like to know how to come back to it in a way that doesn’t feel both jaded and tired of the re-hashing.

    An infusion (transfusion?) of courage and pluck would be helpful

  41. Winston Ash Avatar
    Winston Ash

    The sagging middle. And trying to connect the different scenes when you’re following your plot outline. Sometimes I abandon the outline and follow my instincts.

    1. Ellen Oliver Avatar
      Ellen Oliver

      Yeah! Instincts are best. You rock! There is always editing to make sense of later – get it out while the tide is running hot.

  42. Jen Avatar

    The most difficult thing for me at the moment is writing out the outline using the SENTENCE. My left brain understands the reasons why it’s a good idea my right brain isn’t so understanding. It’s more like, “So, you want me to condense all of this into that? Right… good luck with that buttercup.” Once I get a solid outline though, the hard part is making myself write everyday, even if my day has sucked and I don’t wanna. ๐Ÿ™‚

  43. Jeff Armbruster Avatar
    Jeff Armbruster

    Deciding what the story is about: the conflict, what the hero wants and why the antagonist wants to stop the hero.

  44. Ieva Avatar

    The biggest problem for me actually is the point between writing the story, being done with it personally, and then submitting it for publishing. I am incredibly conflicted about all that publishing thing–on one hand, I want that story to find its reader and be awesome, on the other hand, emotionally I feel exposed and terribly vulnerable.

    The fact that I’m actually good enough to be published semi-easily doesn’t help (somehow, I’m always assuming that the editor probably was on her happy pills that day and didn’t think it through :D)

    1. Ellen Oliver Avatar
      Ellen Oliver

      Thanks for sharing this. I hope I catch your disease. Meanwhile… If you don’t get it out there, I don’t get to read it and I’m waiting for it! If you’ve put your “all” into it – it can’t be less than great.

  45. Kate Avatar

    Middles- I don’t find my subplots and twists grow organically, I always feel like it’s happening “because I say so” or I’m just muddling about filling the space between the clear beginning and end. I’d love to be able to write more complex plots that grow naturally and intertwine with the main plot but instead I feel like my novels are more like a steak (one big main idea) or a salad (lots of little seperate ideas that kind of work together but don’t have to) then a big healthy smoothie of ideals that gel together.

  46. Amazingrace Avatar

    Plotting a novel in advance. I fear over-plotting. Up to now, I’ve been a seat-of-the-pantser.
    Thanks, Holly

  47. Celia Micklefield Avatar

    Staying focused on the piece I’m working on and keeping out of my head all the other ideas clamouring for my attention.My IDEAS and OUTLINES file is bursting.
    Also, when Celia is working on something for a women’s magazine, her alter ego, Mick Alec Idlelife sees the story from a different angle and shoves his nose in. Celia has her women’s market to please; Mick wants to concentrate on the darker side. It’s a constant battle. One day, I’ll probably just let Mick take over.

  48. Sara Avatar

    I stall out and can’t move the plot forward.

  49. Penelope Morford Avatar
    Penelope Morford

    Hi Holly,
    I would have to say the beginning has been the hardest part for me to weave in my novel “The Unborn Prophecy.” Perhaps it is because I have not settled for less then an “edge of your seat” ride into my story. I believe every story should display a rivoting hook right from the moment a reader opens the book. What else is going to gravitate them to keep reading onward (and with good intentions)? An appetizer of mouth watering suspense to catch their eyes, spurring them to continue on into a lip smacking main course of meat and potato drooling drama, satisfying their starving book palate appetite. Now in the case with sequels, a silivating suspenseful dessert roller coaster of ups and downs into a grand finale, hooks the reader to filling their tummies with a smorgasbord of book heaven. They wont want any other book on the book store menu other than yours! Could you blame them? Now on the other hand, every part of a book should be the hardest part to write! Only because every element of a story, whether it be an inquizitive beginning, a mellow drama middle or a climatic ending, is crucial in threading together a successful masterpiece. So here’s to all those masterpieces in the making!
    Penelope Morford

  50. Michele Avatar

    Honestly? The hardest part for me is rejection. And it’s worse still when I’ve written a story that comes from a place of passion, that’s strong and unique and so completely mine, it’s kept me up at night simply so I could find out what happens next, but that isn’t getting a shot in the market because it falls within a genre that’s experiencing such a glut, agents and publishers aren’t sure they want to take on a new author. It breaks my heart.

    1. Jerome Kiel Avatar
      Jerome Kiel

      It’s a sign of the times. There are many people out there who have not discovered their own ability to write at all, far less write well. The trick is to be true to your own talent, your own output. The idea of a rejection from a publisher is never going to be PERSONAL and that’s where you have to differentiate. They have many reasons not to publish, THEIR OWN REASONS, especially when it comes to being commercial. For them, there has to be that good old dirty word in it, ‘profit’. They have to see a way of benefitting from publishing ANY work, so you, the writer, has to keep on keepin’ on. Read Julia Cameron’s THE RIGHT TO WRITE. Things, the song says, can only get bettah…..!

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