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