Start your own '100 Days of Creativity' challenge

This tutorial is meant for all creative types who are trying to get better at their craft and minimize their internal critic. 

Several years ago I participated in National Poetry Writing Month where you write a poem a day in the month of April. After completing the challenge, I decided to continue writing and go for hundred poems in a hundred days.

It was an odd goal to set, I wasn't a poet, but rather a screenwriter seriously questioning my abilities, in the midst of a hairy rewrite that was getting the better of me. But at that particular moment, pursuing a daily habit tangentially related to my craft felt like the perfect vitamin. It not only boosted my confidence, but allowed me to get better at evoking images and stories through tiny story-poems. 

Completing a daily ritual for so many days taught me some things about creativity that I'd like to share. Again, I think the lessons are applicable to painters, photographers, writers, musicians - basically anyone who is trying to get better at their craft:


Our capacity for work and potential output is significantly greater than we believe. Right when you think the well of your imagination is dry you come up with something else. I had no idea of the number of verses and poems I had lying in wait in my brain prior to starting my challenge.

If you produce this quickly, with little time for reflection, your work will be of mixed quality. But it’s far easier to strengthen those raw ideas when you have them on paper as ‘prototypes’ of their future selves instead of waiting for something to be close to perfect in your brain. Only when things are physical can you refine and curate the best of your ideas.


Prior to the challenge, I had wanted to take poetry seriously for some time – and the word ‘seriously’ for me usually translates to reading a book or taking a class on the subject before actually doing something. In the past it’s been easy for me to create prerequisites to physical action, a clever way of justifying procrastination.

But by bypassing any kind of ‘curriculum’, I accomplished significantly more on my own than I could have under someone else’s guidance. I was inspired by other poets, visitors to my blog and my own mistakes – these were my teachers.


Not only does working this way mean you increase your output, put you also become more fluid in your medium. After a while the daily work become a part of your daily rhythm and you start to feel wrong without it. It becomes a kind of meditation, a morning jog, a holistic force that sets the tone for the day, that reminds you that today matters, so use it.


Seeing and experiencing the world through the filter of the medium you’re working in is very exciting. At the time of the challenge I was living in Amsterdam and my morning walks became scavenger hunts, where I’d search for an image, a detail that could inspire that day’s work. The city and my thoughts became a precious thing that I was constantly trying to put into words.

I am now more convinced that as creators we must consume the world around us and respond to it, in the voice and medium of our choosing, on a daily basis.

But it doesn’t have to be all serious work. Play with your process when your stuff gets stale and you get tired. You can change up things by experimenting with different tools. For example, I tried writing poems on paper cups, with tape recorders and apps.

During the challenge, I obsessed on quantity – not quality. And ironically a side-effect of shutting off my internal editor is that I did produce some things I was proud of. The challenge combined with blogging created a kind of sandbox where I could mess around with no real intent or ‘master plan’ – yet I was extremely productive and surprised myself with the results. Odd.

I wonder if our insistence on making ‘one of a kind’ work right out the gate prevents us from eventually making one of a kind work one day? Final outcomes we can be proud of are the result of constant experimentation and wrong turns as we find our way down a foreign road. And sometimes you have to lock your ego and editor in the trunk just to make some real progress down that new path.

Depending on your medium of choice, I encourage you to journal these daily artifacts you create – via twitter, tumblr, instagram, wordpress, etc. – opening yourself to the feedback and inspiration of others; allowing some transparency to your bungles and successes. I promise you that kind of transparency is not as embarrassing as it seems. It’ll give you some accountability to finish your challenge and be a great reminder not to take yourself too seriously.


If this idea resonates with you but 100 days straight sounds insane, then I would warm up with a 30-day challenge to create something everyday. You could work in a medium directly related to your career and craft, or in a new medium tangentially related as a form of cross-training. Remember, the definition of success in such a challenge is quantity, not quality. You'll have time afterwards to curate and invest more time in the results that you think deserve it. 

For more ideas on how to design a creative challenge of your own I recommend these two resources:

PS You can view some of my favorite poems from my challenge here.

PSS Check out my tutorial on journalling, that might help you come up with a system to document your daily creative habit. Also check out my screenwriting class, we're always looking for new writers.

Screenriting Tip: getting over first draft paralysis

If you're paralyzed by the thought of writing a first draft then try this simple exercise:

  1. Grab a notepad.

  2. Set a timer for ten minutes.

  3. Jot down the scraps, bits of dialogue, images you have simmering in your head.

  4. When the timer goes off, if you're still in the flow of things, then keep going. 

  5. Or, if you find yourself stuck, and feel like you've transcribed everything in your  head, then set the notepad aside. 

  6. Return to your notepad in a day or two, and repeat the exercise, using the ten minute intervals to flesh out your previous scraps and start connecting the dots into a 'story'.

Like any other activity, starting is the hardest part. 

Keeping a Writer's Journal

Writing is a lonely process. Sometimes we’re lucky enough to find a group of writers going through similar bouts of frustration and writer’s block, but even then there’s a limit to how much of our own insecurities and our story's weaknesses we’re willing to share out loud. That’s why I highly recommend you supplement your own creative writing work with a journal that sits on the sidelines and you use to catch your feelings and progress as your work evolves. 

What I mean is a journal that is a kind of behind-the-scenes record of your story and process as it emerges in real-time. A record of your story’s growth. When we’re working on something new, there's usually a constant conversation one has with oneself where they’re trying to figure things out. Some of that is negative - self-doubt, envy, procrastination, etc. Some of it is more question-related about all the different possible directions you can take the work - how it can be restructured, workshopping a bit of dialogue, for example. That constant inner chatter is good and can be insightful, but also distracting. A writing journal is a way of getting those voices out of your head, both the negative and constructive. Writing a journal that you know will always be private can be a cathartic process where you can be honest about your own ability, where your story stands, where it needs work, what your greatest fears are, how you wish you could write more, how you’re grateful for the writing time you’ve been able to carve out, etc. Inevitably, I find even when I’m in the foulest of moods and super-pessimistic about my own abilities, somehow writing that out - writing about how much I suck - inevitably leads me to a positive place where I see I do have something, and it’s just a matter of making these changes, or staying patient, or seeking another person’s objective read of the material. 

You can use your writer's journal in whatever way makes sense for you. But I wanted to offer some suggestions to give you a sense of the power of documenting your thoughts and writing process as you create. Here are some ideas and exercises:

  • Use it to warm up - where you write nonsensical, stream of consciousness thoughts, to limber your imagination and voice before the more serious writing starts. For example you could start your work with some morning pages

  • As a form of cooling down - you can use it as a simple log of what you accomplish in each writing session, how long you worked for, what you’ve changed, what still needs work. 

  • On days that you get stuck, you can make a simple note of that in your journal and began to think with pen and paper about where you’re stuck and why. It can allow you to continue to write through your writer's block and frustrations.

  • Sketch out character and location profiles, either imagined or real, related to your work

  • Alternatively, instead of focusing on your own work and process, you can aim your writer’s journal outward at the work of others you find inspiring and related to what you’re trying to accomplish. For example, you can copy pieces of novels, screenplays, poems into your journal, analyse and dissect them, or simply have them in one place as a kind of commonplace book you can refer to later. 

But what is the best tool for recording these ideas? There’s an ongoing debate about the pros and cons of digital versus analog tools. I don’t believe one is necessarily better than the other - but I think your physical memory and history of a tool plays a huge part in that tool’s success. For some of us, and I am part of that generation, we spent a large part of our secondary years writing school reports and stories by hand. If you’re in that group, then this tactile, analog process is very important, and I think it’s something we shouldn't completely abandon. I do have a kind of love affair with physical journals, even though speaking objectively they make no sense in today’s world, a digital journal or app is so much more effecient. But I think it has something to do with my childhood memories of trying to be a storyteller, when I would tweak a sentence over and over again by hand until it felt right. And I think nowadays especially, where we spend so much time staring at screens, the process of writing in a physical journal, with a pen instead of a keyboard, becomes an island of respite from the cacophony of digital distractions.

Over the years I've accumulated a number of different kinds of physical journals. Each has it's own unique personality and in subtle ways affects my work, fluidity and ultimately my ideas. What I love about physical jotting is how quickly you can move from words, to sketches, to mindmaps, and back. I've had some success with Moleskine's Cahiers, because they feel cheap yet are durable, so I'm less precious about what I'm writing. I've recently started experimenting with Japanese stationary, as a way to keep things interesting. Again, speaking objectively the subtleties of a journal's size or paper texture shouldn't matter, but I think they do, I think the choice and specifics of our tools always leaves a mark on our work and you should pay attention to that.

On the other hand, we do live in a digital age, and many of you don't have a romantic relationship with pen and paper, to you it's antiquated and cumbersome. If you feel that way, or lack that physical history I described, then you should totally embrace your digital options. It’s quite amazing the ability to sync, back up, tag, entries and know that you will probably never lose those thoughts. And just like a physical journal’s size and texture can affect your journaling results so can the parameters of a digital writing app. I've had some success with Day One. It's a cross-platform Mac/iOS journal, but I'm sure there is an equivalent for PC and Android devices. In my opinion, the most useful feature is the ability to tag your entries, so that you can gather them up later for reflection. In this way I can enter in several entries during the day on a range of topics or projects, tag them, and they're indexed - a physical journal doesn't lend itself so easily to gathering up such short fragments. And the contextual data that a digital journal like this gathers can also be insightful - it automatically records the date, time, weather and place - so for example it can help tell you in what conditions you do your best brainstorming.

You'll only find out through practice what journalling option works for you, and you might find each project has it’s own approach - a mix of physical and digital recording for example. And part of the fun of writing that work will be finding the journaling tool to use alongside as your story develops into full maturity.

If this topic interests you and you need more inspiration, take a look at how these three great artists used their journals alongside their work to express their highs, lows and messy thought processes: