Grab your free resources for writers + creatives →

How I Finally Won NaNoWriMo After Multiple “Failed” Attempts

As a writer who battled creative blocks for many years, NaNoWriMo was a mountain that seemed nearly impossible to scale during that time. If you aren’t familiar with NaNoWriMo (National Novel Writing Month), it’s an annual event in November that challenges writers all across the world to write 50,000 words for a novel in just one month.

For a long time, I struggled to churn out a few hundred words in a day, so 50,000 in one month? That felt like a far-off dream. My creative bocks were so formidable and deep-seated that they not only made it difficult to finish anything, they also stole the joy of writing from me because of the mental and emotional upheaval I faced every time I set out to write. It was a big achievement for me in 2018 to finish and publish my short story, The Soul Broker, which was just under 7,000 words.

Every time I’d find a flow, my creative blocks (fear, self-doubt, perfectionism) would inevitably slam on the breaks and keep me from moving forward. I attempted NaNoWriMo three or four times and never got past around 28,000 words.

Now, don’t get me wrong ─ any words put down on the page is a win. I don’t consider my prior attempts “failures;” while I didn’t hit the 50,000-word goal, I still made time for my writing and stretched my creative muscles during that time, and I was grateful to and proud of myself for showing up. But I still had that goal to hit the 50,000 because when I did, I knew it would mean I had finally overcome those blocks and taken control of my creativity.

Refusing to accept that my creativity was “broken,” I went on a personal development journey over the past few years to get to the core of my blocks. In November 2019, I completed NaNoWriMo with 50,022 words. It was a HUGE moment for me that I’ll never forget; it was the culmination of a lot of soul work that showed me just how far I’d come.

To pass on those lessons to anyone else who is facing these same challenges, here are some of the biggest shifts and breakthroughs that led to me finally being able to finish NaNoWriMo (and write consistently in general).

How I Finally Won NaNoWriMo

I took my prep work seriously

In my past NaNoWriMo attempts, I worked off a loose outline or no outline at all for my projects. This meant that I was having to make a lot of big storytelling decisions as I went, which sucks up a lot of time. Some people are natural-born pantsers (writers who don’t plan anything before they write) and love to work this way, but for me, it felt very unnatural and slowed me down. Barely any of the work I did under these conditions ended up being unusable.

I realized that if I was going to make decent progress each day on my word count and actually end up with a first draft that had good bones to work with, I had to start with a strong foundation in the form of a detailed outline. This is just how I work best as a writer and accepting that allowed me to prepare ahead of time rather than fight myself the whole way through.

I wasn’t worried about having every single scene outlined, but I filled in as many as I could, making sure that all of my story and character arcs were fleshed out. I had the flexibility to make changes as I made discoveries along the way, but doing all of that structural work ahead of time took the pressure off so I could enjoy the writing process.

Figure out what you need as a writer to do your best work and put systems in place to support that. Don’t judge yourself based on other writers’ habits or processes ─ we all work differently. The important thing is that you write. What prep work is going to help you do that as smoothly as possible?

I identified my habits + created a ritual

Self-awareness was a simple but crucial element that helped me write consistently. It’s super easy to fall into the trap of bad habits and triggers if you don’t recognize them. Pay attention to the circumstances under which you are most focused and when you feel distracted, and what you are feeling/need at any given moment to get back on track. Get creative about controlling the conditions around your writing time to maximize your sessions.

I tend to be more distracted and restless during the day, so I only wrote a couple of times during the afternoon. The rest of November, I wrote at night. I also realized that I often prefer getting comfortable on the sofa under a blanket with my laptop, so for most of my writing sessions, that’s where I was. Why force myself to write at a desk when I’m not feeling it? When the mood struck and I was feeling restless, I wrote at a coffee shop so I could be around other people’s energy ─ I paid attention to what I was feeling and worked with it rather than against it.

It sounds simple, but it’s crazy how easily our blocks can manipulate us with simple distractions if we don’t pay attention to what’s actually going on and remove that resistance.

I’ve also found that wearing headphones and listening to music while writing overrides the noise in my head so I can focus better. (Shonda Rhimes says she does the same thing.) I keep water by me at all times because I get thirsty when I write and I open up my story mood boards before I start writing because visuals stimulate my creativity. Create a ritual around your writing that will send a cue to your brain that it’s time to get into writing mode.

I used the eff out of placeholders

Placeholders are common practice for most writers when working on their first drafts. It saves you time when you can’t think of the right word to use, haven’t named a character or place yet, or don’t feel like wasting time describing something such as a setting or physical appearance. They’re also handy when there is a piece of a scene you want to include but you aren’t sure about the details yet. Instead of breaking your flow to figure it out as you’re writing, a placeholder will allow you to keep going. For example: [Character A and Character B have a romantic moment.]

As a recovering editor-while-I-write and perfectionist, this was a hard technique to adopt but once I did, holy crap. My writing life got so much easier. It took some time for me to train my brain to use them, so don’t beat yourself up if you run into the same resistance at first. It’s about clearing out as many roadblocks from the first draft as possible so you can focus on getting the story down on the page and have something to work with.

I got to the root of my limiting beliefs + changed my story

Creative blocks are caused by fears, self-doubt, and limiting beliefs operating deep in our subconscious. When they manifest, it’s often through patterns we automatically fall into in order to protect ourselves from having to face the unknown or to prove what we believe is the inevitable (i.e. failure). The first step is to identify the source of your blocks and peel back their layers. The more I got to the root of mine, the more empowered I was to recognize them for what they were when they came knocking and make a different choice rather than follow them blindly into the dark.

Check-in on the story you’ve been telling yourself about your blocks. Do you find yourself identifying as someone who “can’t finish things”? Do you tell yourself you’re not cut out for this or that you must not be good enough because of how much you struggle? Holding onto these narratives means you are personally identifying with your blocks as though they are a personality trait rather than a mental block. It keeps you caught in a cycle of confirming those beliefs over and over again. When you disassociate from them and change the story you feed yourself, you free yourself from their grip and start operating from a practical, solution-based mindset.

I established a better relationship with myself

After “failing” NaNoWriMo multiple times and watching the pile of my unfinished projects grow, I had very little confidence in myself that I’d ever become the writer I wanted to be. The trust wasn’t there. Like any other relationship, you build trust by showing up consistently. I started taking my commitments to myself more seriously, like not flaking out on the time I set aside to write. I stopped negotiating with my mind when it tried to talk me into doing something it deemed “more important;” I began respecting my writing as a priority because it is important to me.

I also became more mindful of my inner dialogue. You hear your own voice more than you hear anyone else’s; what is it saying to you? Is it kind and supportive or negative and always tearing you down? Talk to yourself the way you would talk to a close friend. A rule of thumb: if you wouldn’t say it to your best friend, don’t say it to yourself.

NaNoWriMo Tips

To recap, here are my tips for winning NaNoWriMo and writing consistently in general:

  • If you aren’t a pantser, figure out the amount of prep work you personally need to do in order to be able to dive into the first draft with as few roadblocks as possible.
  • Practice self-awareness: identify the circumstances under which you feel most focused and build your writing sessions around them. Ask yourself what you need before every session ─ it won’t always be the same.
  • Create rituals that will send cues to your brain that it’s time to get into writing mode.
  • Use placeholders ─ they’re lifesavers!
  • Get to the root of the fears and limiting beliefs that are driving your blocks, and check-in with the stories you’re telling yourself about your writing and creativity. Are you letting your blocks define you?
  • Build trust in yourself by proving that you’ll stay committed and show up for the things you care about, like your writing.
  • Audit your inner dialogue: does your self-talk sound like a supportive friend or are you always tearing yourself down?

Good luck, writers!


After suffering from creative blocks that led to multiple failed attempts at NaNoWriMo, I finally experienced breakthroughs that helped me write 50,000 words in one month win the challenge. Here are my tips on beating writer’s block and winning NaNoWriMo. After suffering from creative blocks that led to multiple failed attempts at NaNoWriMo, I finally experienced breakthroughs that helped me write 50,000 words in one month win the challenge. Here are my tips on beating writer’s block and winning NaNoWriMo. After suffering from creative blocks that led to multiple failed attempts at NaNoWriMo, I finally experienced breakthroughs that helped me write 50,000 words in one month and win the challenge. Here are my tips on beating writer’s block, writing consistently, and winning NaNoWriMo.


Leave a Comment


lifestyle goods

Chic printables, apparel, and lifestyle goods for fiction lovers, writers, and creatives to help you stay inspired as you pursue your dreams.