Tips for Four Personality Tendencies Struggling Through NaNoWriMo’s Muddled Middle

We are one-third into NaNoWriMo. How are you doing? I’ve found for myself the ten days from November 10 to November 20 are often the hardest. The early excitement wore off three days ago. I’m usually behind by November 10 but it is still possible to make it up. After ten days of locking myself away to put words on paper, I remember writing can be a lonely business.

We all react to situations differently. NaNoWriMo is a pressure cooker bringing out your personality with all its built-in problems and strengths. Gretchen Rubin identified four personality tendencies and their unique challenges and strengths for starting and completing projects or establishing habits. You can find a quick quiz to identify your type here:

This blog post gives personality-linked tips to make it through the muddled middle of NaNoWriMo. Rubin identified four groups depending on how each type responds to external and internal commitments: Obligers, Questioners, Upholders, and Rebels.


Most people are Obligers. Obligers respond best to external commitments. In NaNoWriMo they ask themselves “what do I need to do today to avoid letting other people down?” They have a hard time carving out “me-time” or following through on internal commitments. By middle of NaNoWriMo other people’s expectations get in the way of work on their novels.

Tips for Obligers:

  • You respond best to external commitments, so your biggest mistake is trying to do NaNoWriMo alone. Ask your spouse or a friend to hold you to a commitment to finish your 50,000 words by the end of November.
  • Attend NaNoWriMo Write-Ins. The group atmosphere provides external expectations through the sprints and other writing activities. If none of the write-ins are are convenient, organize your own. Knowing you have to show up for other people creates an important motivation for the obliger.
  • The middle of NaNoWriMo is fraught for Obligers. By now other people make their needs known to you and a purely internal commitment isn’t enough to carry you through. It’s time to outsource! List your obligations and figure out which ones you can have someone else do for you.
  • Obligers respond well to treats. Build a set of treats into your NaNoWriMo schedule. A friend of mine wrote little inspiring notes to herself. She paired each note with chocolate treat and put in an envelope. When she met a NaNoWriMo mini-writing goal she opened the envelope and had a mini-celebration. You can find little packs of inspiration already in envelopes at many gift shops or on Amazon. Here is an example: Treat yourself!


Questioners don’t respond well to external commitments but they do well at following their own heart, as long as they know what their heart says. Like the name implies, this personality type questions everything and overanalyzes all decisions before implementing. By the middle of NaNoWriMo the questioner’s biggest challenge is analysis paralysis. If you are a Questioner, your challenge may be that you didn’t even decide to start NaNoWriMo until a week into the project and now you are starting behind. Or perhaps you started on day one, but you’ve arrived at the first third of the book and you don’t know how to move forward. You want to do a bunch of research before proceeding, but you know that will slow you down.

Tips for Questioners

  • When Questioners struggle, it is often because they’re not convinced that writing a novel is the right thing to do or that they are writing the right novel. Take time to understand why you are writing this book and what the characters mean. Use part of your NaNoWriMo word count to write up your character biographies, brainstorm book themes, and work out plots.
  • Allow yourself to outline the book or the chapter, even if you are starting late. But be sure to count this as part of the NaNoWriMo word count. It all counts during NaNoWriMo.
  • Don’t just think: write your thoughts. If you aren’t sure how the novel should proceed in this muddled middle period, write out all the possibilities. Count all the words you’ve used to think this through.
  • Pulled to research before you continue writing? Allow yourself to do it, but time it. Give yourself fifteen minutes for research, no more than that. Then, get some words down.
  • Indecision is a Questioner’s kryptonite. Give yourself permission to discover the right way to go by writing the possibilities on the page. Remember, all words count in NaNoWriMo, including those words you spend discovering your story.


Upholders are good at following through on both external expectations and internal commitments. They want to get things done. Upholders arrive at the mid-point of NaNoWriMo with a pile of to-do lists and a fear of not succeeding at all of their many projects. Writing a novel is a big project any month of the year. Completing a novel in a month in November when you must prepare for Thanksgiving, buy presents, complete work projects, and so forth, threatens upholders with burn-out.

Tips for Upholders

  • Schedule your time. The biggest danger for an Upholder is burnout. You must schedule your time to ensure that everything has a place in your life. Take the time now to write a schedule. Add your most important tasks and then take a look and see where your novel writing can fit in. Schedule writing time and let people know when you will be writing. As much as possible, make your writing both an external and internal expectation.
  • Monitor your progress. Upholders do best when they can see how they are progressing. Commit to updating the NaNoWriMo word count, either on the NaNoWriMo page or, even better, on a calendar that is visible to you.
  • Habit-stacking works well for Upholders. Habit-stacking means that you attach a new habit to an old one. For example, make a deal with yourself that you will write for ten minutes right after brushing your teeth. By stacking writing time with something you are going to do anyway, you’ll be more certain to do it.
  • One of the biggest challenges for Upholders is avoiding burnout. Determine which other activities you must do in the month of November you can outsource. For example, last year during NaNoWriMo I outsourced cooking Thanksgiving dinner to Whole Foods. Whole Foods offers prepared Thanksgiving dinners that you can order. You can also order Thanksgiving from several restaurants in town. A friend’s favorite go-to for party prep is The Rendezvous restaurant. If you can afford to do so, outsource your cleaning for November. Make a list of expectations for the month of November and then write down who you will outsource each one to. Then do it.


Rebels respond poorly to both internal expectations and external commitments. They value freedom. They don’t want anyone or anything to pin them down; not even themselves. They may have arrived at the middle of NaNoWriMo with a book they intended to write and now they’ve switched books. Or if they haven’t, they lost their motivation to write and now feel frustrated with themselves for being so contrary-minded.

Tips for Rebels

  • The most effective strategy for Rebels is adopting an identity as a writer. Ask yourself, “What would a writer do?” when faced with challenges or other activities that interfere. A great tool is Chuck Wendig’s The Writer’s Prayer, which begins “I am a writer, and I am done fucking around. That which has prevented me lingers no longer. I am wind and storm and lightning and I shall huff and I shall puff and I shall blow all the barriers down. Then I will drink whisky made from the fear-urine of my loudest detractors and find power in their disbelief.” Go read the rest:
  • Make writing convenient by setting up your environment. Each night I set up my writing area with a pot of water, a tea bag, a thermos of soy milk. I adjust my monitor and close out everything except the part of my novel I’m working on. When I wake up, I can just go to it and start. Environmental cues are very important to Rebels because their biggest value is freedom and doing what they want. So make writing your novel attractive. Make it something you want to do.
  • Do it different! Rebels thrive doing things in against type. They think different. Harness that! Write against expectations. Do it at an odd hour. Write something that doesn’t quite fit into NaNoWriMo. Be different and rebellious in the pages of your novel. If other people don’t like it, well, take Chuck Wendig’s advice and say, “Nobody tells me who I am or what I can’t do. I tell stories. I write characters. I make true shit up out of thin air. And nothing is more perfect than that.”

Whatever your personality tendency (and you may see yourself in more than one) you can do this! Write on friends!


About the author: Carolyn Ivy Stein is a writer living in Memphis, TN. Her work in progress is a rousing pirate chase set in 38 AD in Alexandria, Egypt. Her personal web page is You can find her personal blog at She is a co-blogger on the Sea History Adventures blog


Growing up with NaNo

I have been doing NaNo for over 1/3 of my life. Well, that’s a surreal sentence to look at.


I started doing National Novel Writing Month when I was 17 and still doing it now at 29. So I’ve actually grown up doing NaNo. If I’d known about NaNo earlier, I probably would have done it then too.


But this is less about how long I’ve been doing NaNo and more how I’ve grown as a writer doing it. So let’s start at the beginning.


When I started doing National Novel Writing Month in 2006, I was a mess of a writer, for lack of a better term. See, I’ve always wanted to be a writer but by the time I found NaNo, I’d been told I was terrible at it by teachers from 5th grade all the way to my, at the time, current English teacher. So when I stated with the idea of doing this month long madness, I barely had the confidence to write more than a few hundred words. Maybe a thousand, if I’m being generous.


The next year was mildly better. I came out of my shell (sidenote: if you want to know how NaNo worked with my lack of social skills, check out the other blog post I wrote, The Shy NaNoWriMo: A Personal Essay) and gained confidence in my writing. Unfortunately, I couldn’t tell you how much I wrote that year since my memory is garbage and that was before my current account. But it was more than 2006.


2008 and 2009 were pretty similar. I was more active in the region and wrote more each year. In 2008, I ended with just under 27k and in 2009, the final count was 35,002.


And those were the last years I didn’t “win” NaNoWriMo. The reason I’m telling you all this is to let you know that while this event may be silly and fun, it can also really help you grow as a writer. It helped me. I’ve written more during November than I have in an entire year (well, before becoming a professional technical writer).


In fact, I can even credit NaNoWriMo with helping me get said technical writing job. The people I’ve met and the skills I’ve learned from participating in this event for over a decade has made me the person I am today, the writer I am today.


While I may not be published yet, I’m getting there. This event can change your life if you let it. Or not. No pressure, you know?


All that being said, I’ve grown in a lot of ways thanks to NaNo: writing ability, sociability, and confidence. And I hope it can help you too!


If you want to speak to me more about this, you can find me in the forums, FB group, or in person at an event. Until then, though?




How To NaNoWriMo

Okay so based on the title, you might be expecting a tutorial on how to do/win NaNoWriMo. That’s not what this is, like, at all. Each person does NaNo differently I don’t think there is any “one real way” to win. Winning is subjective anyway.


Okay, no more tangents. Back on topic here. How To NaNoWriMo. While the purpose of NaNo isn’t winning, it’s about getting the words out, sometimes you need some advice on the best way to get the words out. Maybe what you’ve tried before hasn’t worked out or maybe you want to change it up. No shame in either.


So, you may not know this but in the NaNo ‘verse, there are three main types of participants. It may sound weird to have such a small number of “types” but it’s pretty true from my experience. So what are the three types? Planners, plantsers, and pantsers. I’m aware the last two sound crazy but let me explain.


Let’s start with Planners. Planners are those special little ducklings that can write down a full outline, synopsis, character breakdowns, everything before they start writing. They plan basically everything. Or at least way more than other WriMos. I personally can’t do that so more power to the people that can. The dedication is real.


Next up, Plantsers. It sounds the craziest because it’s not even close to a word. But this is a hybrid of planners and Pantsers. But plantsers tend to plan just a few things. Personally, I have a pretty generic idea of what’s going to happen but don’t make any notes, even if I think of other details. I start from the generic idea on day one and just fly by the seat of my pants.


Other Plantsers (like HGL, for example) might do more, others might do even a little less. Some start with just a character and let them decide what’s going to happen based on that. This method can be exciting but stressful. But it’s a good compromise between the other two types.


Pantsters fly by the seat of their pants. No, really, that’s how they got the name. At least to my knowledge, at least. Anyway. Pantsers are the impulsive participants that have no idea what’s going on, it’s just going starting at 00:00:01 November first.


So those are the three main types of NaNo participants. If you think one sounds like what you want to do, go for it. Like I said before, there is no one true way to win NaNo. Some people in the region thrive doing planning, others like flying by the seat of their pants.


If you still aren’t sure which type of writer you are or want to be this year, consider trying something you haven’t tried before. I found out after a lot of trial and error that my best years were when I was plantsing. But that may not be the answer for everyone.

But no matter what type of WriMo you are, I wish you the best and may the words be ever in your favor. Or other clever pop culture reference outro here.




The Shy NaNoWriMo: A Personal Essay

Hi, I’m kitkatt and I’ve been doing NaNoWriMo since 2006. So that would be 12 years as of 2018.

A lot of people feel like they have to go to events and participate to get the most out of NaNoWriMo. That both is and isn’t true. How do I know? I was super shy when I started NaNo.

So way way back when I was 17 in November 2006, I heard about National Novel Writing Month in late September, early October. Being the totally outgoing person I was at 17, I tried to convince my friends to do it with me to… less than stellar success.

I didn’t want to meet new people on my own. I wanted to meet new people with similar interests while still having the safety blanket of friends around. Like I said, only a few even pretended to humor me.

So sometime in the latter half of October, I went to the Kick Off Party, held by the then ML. I dragged two friends with me and we were quiet and awkward, mostly only waving hi to the other people but talking amongst ourselves. Then we left. And that was all I did for NaNoWriMo 2006. I barely wrote because I was an angsty teenager and had angst to angst. Or something.

2007 wasn’t too much different. I went to a write-in at the Wolfchase Barnes and Nobles and watched the write-in from a distance because I was too scared to actually go, you know, talk to people. The next write-in I could get to, I came over and was identified as the awkward looking girl from Barnes and Noble. I barely talked besides introducing myself but it was easy to find common grounds with other writers.

2008 is when I started getting social and now. Well, if you’ve been to an event in the last 6-8 years, you’ve probably seen me being a hyper, weird mess. But I also understand that it isn’t as easy for some people.

So why am I writing this? Because I know what it’s like to be shy. Meeting new people is awkward and what if you have nothing in common? What if they immediately hate you? Those were the kind of questions I dealt with when trying to get into the social part of NaNoWriMo.

But I have a secret for you: you don’t have to be social for NaNoWriMo. Some people find it helpful, some people don’t. Where some people can write around people or spitball ideas with others, some writers can’t. And that’s 100% fair. Actually, maybe more than 100%.

My point is this: if you do NaNoWriMo, don’t feel like you have to participate in real life events. We want you to but it isn’t required. Being shy doesn’t make you lesser. You’re still one of us and we’re going to cheer you on regardless.

I hope to see you at an event! I’ll be the crazy lady with the flower tattoo.




NaNoWriMo 2018 Season is Here!

Welcome to the first week of October, Wrimos!


As many of you know this is the time of year where many of us begin to hope for fall weather changes, pumpkin spice everything, Halloween decorations, and how much candy we can consume before we feel sick. Of course, if you are familiar with National Novel Writing Month then there is one other thing you begin to do this month…


You stress out because NaNoWriMo is coming!


If you are like me then October hits you like a ton of bricks every single year. You start to sweat profusely, panic about the lack of ideas or the abundance of ideas that you have in your head, swear a little if you’re so inclined, and wonder how this year you will silence your inner editor who has been ripping apart all of your more recent work over the last few months.


Want to know a little secret, though?


You have time.


Believe it or not, you have time to get your writerly mess of a life together and ready to go on November 1st. There are 31 days in October before we hit midnight and we are off writing as if our lives depended on it. If you are a pantser you know the drill: Ignore every little inkling of your brain telling you that you aren’t ready to write something you don’t know anything about, and just hit the pavement when the clock strikes midnight.


If you are a planner, it’s simple: Give yourself just enough time (Chris Baty suggests a week) to plan what needs to be put on paper, and let your imagination and determination do the rest.


The point of NaNoWriMo isn’t to make the next bestselling book, after all. The point is simply to write; to get your ideas on paper as quickly as possible and to get out of your comfort zone a little. So banish that inner editor of yours, and while you’re at it tell it to take the stress with it. October is full of promise and full of ideas just ripe for the picking. So take one, and mold that idea into something that – come November – you will be ready and excited to write! I know this year will be amazing, and I cannot wait to see what November has in store for all of us.


This is Brooke Wheeler, over and out! Write on, Wrimos!

Guest post to the NaNoMemphis Blog by one of our Awesome Wrimos! Check Brooke out on Facebook, Twitter, and Her Blog!