Writing Challenge Index & How to Plan Your Writing Year

Writing Challenge Index

A writing challenge is perhaps the fastest and most enjoyable way to grow as a writer, and to finish an interminable writing project. Pick and choose your daily, weekly, monthly and yearly goals and piece together a year you can’t wait to write about!

Engage in a Year-Long Writing Challenge

A year-long challenge takes a lot of focus and stamina, and it’s easy to get bored and fall off. However, a big challenge can also be very rewarding, both in terms of the end result, and the habits that you develop throughout the year. And even if you “fail”, you will no doubt have learned a lot, and made considerable progress in the meantime.

If you would like to take on a year-long writing challenge, here are a few suggestions:

  1. Write every day. Even a few words a day can help to keep your project moving forward. If you need motivation and support, start a WriteChain!
  2. Write first thing every morning. Many writers do their best work in the morning, especially before the rest of the family wakes up. If you need some company, you can join the #5amWriters on Twitter.
  3. Take the Writing Journal Challenge and fill in a writing journal worksheet every week.
  4. Take the Ray Bradbury Challenge and write a short story every week. This is a really fun challenge because you:
    1. Finish a project every week.
    2. Get to work on something fresh and exciting every week.
    3. Can experiment with lots of different forms and genres.
  5. Write a novel. It’s a common but admirable, challenging but achievable ambition. Will this be the year you finally write your novel? If you’re not sure where to begin, I would recommend a plot formula.
  6. Pitch a novel. If you have a completed manuscript and you’re looking to publish it traditionally, you might want to focus your efforts on finding an agent. If you need help, (and a deadline) Pitch Wars is an annual mentorship programme that helps match writers with agents.
  7. Publish a novel. If you would rather go down the self-publishing route, you might want to focus on getting your manuscript ready for uploading, and on preparing marketing materials.

Pick a Year-Long Focus

It seems natural to focus your year around a large project like a novel or a series, but sometimes this leads to feeling stuck, overwhelmed, or bored. You forget why you tackled the project in the first place, and feel as if you’re repeating the same mistakes over and over again.

Does this sound familiar? If it does, it might help to take a step back and instead focus on the journey rather than the destination.

  1. One simple strategy is to choose a specific word that summarises your goal for the year, and serves as a reminder. You can even set a regular alarm on your phone to refocus you during the day. For example:
    1. Prolific
    2. Inspiring
    3. Elegant
    4. Succinct
    5. Powerful
    6. Fun
  2. If you’re having trouble deciding, consider drawing a Tarot card to focus on for the year. Study its meaning and symbolism, and if it’s a major arcana card, its place in The Fool’s Journey.
  3. You might also choose to focus on a specific area that you feel you need to improve in. For example:
    1. Writing dialogue
    2. Describing settings
    3. Editing and revising
    4. Plotting
    5. Vocabulary

Intersperse a Few 7-Day Writing Challenges

A week-long writing challenge is just the thing if you’ve been feeling stuck or unproductive in your writing life. Here are a few suggestions if you feel inclined to try a challenge a month.

  1. Write a piece of flash fiction every day.
  2. Write a love letter every day.
  3. Write without using any words you used on the previous day
  4. Fill a page every day.
  5. Create a zine or chapbook in a week.
  6. Outline a novel or series in a week.
  7. Fill up a notebook in a week.
  8. Discover and retell a new story every day.
  9. Write, edit, and share a piece in a week.
  10. Write a paragraph around the same theme every day.
  11. Journal as a character every day.
  12. Revive and revise an abandoned piece.

7 Day Writing Challenge List - Monthly Writing Challenges

Try a Longer, 30-Day Writing Challenge

A 30-day writing challenge hits the perfect balance for minimum stamina and maximum productivity.

  1. Participate in National Novel Writing Month – the challenge is to write a 50,000-word novel (or novella) in the month of November. This is my favourite challenge of all time! If you’re considering taking part, don’t miss my list of NaNoWriMo Resources.
  2. Here is a list of prompts for a 30 Day Flash Fiction Challenge – if you’re feeling ambitious, you can go for the whole 100 days!
  3. Monthly Writing Challenges on Twitter – commit to writing at least 500 words a day, and announce your progress to fellow writers on Twitter to stay accountable.

Surprise Yourself with a Spontaneous Challenge

  1. Have you tried a 10K day or weekend? It’s one of my favourite challenges, especially during NaNoWriMo. The aim is to write 10,000 words in a day, or in a weekend. I assure you, it’s very do-able!
  2. Word War – a word war is when you sit down with another writer and try to write more words than them in a given time limit. If you don’t have a writing buddy, you can also word war with yourself (try to beat your last attempt), or join a virtual word war at wordwar.io (when it comes back),
  3. Complete a Word Crawl in a day or week – you can use this word crawl worksheet to design your own word crawl with sticky notes, or take a look at the archive at WikiWriMo.
  4. Write a short story in 1 hour – this is a great challenge for instant gratification. Start and finish a short story, from idea to completed first draft, in 1 hour.
  5. And for an even greater surprise, you can always design your own challenge.
RELATED:  Creative Writing Syllabus & Rubric (for Writers and Tutors)

Keep Up a Journal Writing Challenge

If you’ve previously tried keeping a journal or diary and failed, don’t worry! There are less exacting alternatives…

  1. Keep an advent journal – journal every day leading up to an event. This might be a holiday, an exciting change such as starting a new job, or moving into a new house, or an anniversary. This is an interesting exercise to explore feelings of anticipation and excitement, or more difficult emotions like anxiety, dread, or disappointment.
  2. Journal on a particular day every year – you can take this challenge in a few different directions.
    1. You can choose a random day that has no particular significance and use it to document your daily life.
    2. You can choose a significant day such as a birthday, anniversary, or red-letter day, and document your celebrations or family traditions.
    3. Or, you can make up your own writing holiday. For example:
      1. Alphabet appreciation day – on which you delight in letters, familiar or foreign.
      2. Perfect day day – on which you write your annual vision of the best day ever.
      3. Contrafibularities day – on which you write with invented words.
  3. Keep a project journal – as a writer, a writing journal is a useful tool for practicing and learning. In particular, a short entry each day that you work (or don’t work!) on a story can help you learn more about your writing process, and figure out how to approach your next project.

Prepare for Annual Writing Events

  1. Every year during NaNoWriMo, municipal liaisons organise local write-ins which are great fun and can seriously boost your word count. If you can, I urge you to plan to attend at least one write-in in person.
  2. 3-Day Novel Contest – this is a yearly contest that runs over the American Labour Day weekend. There is an entry fee, but one winner receives a publishing contract. If you don’t like the idea of paperwork or of being judged, you could certainly challenge yourself to a 3-day novel on your own terms!
  3. Different countries have different dates, so I recommend looking up your national…
    1. Letter day
    2. Writing day
    3. Book/reading day
    4. Poetry day
  4. It can also be fun to celebrate the birthdays of your favourite authors (perhaps with a pasty and pastiche), or your favourite books (perhaps with a spot of bibliomancy).

Schedule Regular Study Time

Challenge yourself to study and learn more about literature and the art of writing. Look for classes at your local community centres, or enrol in an online course.

  1. Masterclass offers classes from many famous writers, including Margaret Atwood, Dan Brown, James Patterson, Neil Gaiman, R.L. Stine, and many more. (affiliate link)
  2. I offer unique online writing courses at The Lady Writers League that are designed to help you plot, develop characters and worldbuild all on one page. Click here to learn more.
  3. If you’re researching a particular culture or era, look out for MOOCs on sites such as edX, FutureLearn, Coursera and Khan Academy.

How to Plan Your Writing Year

  1. Write out a list of writing challenges that you would like to try.
  2. List the writing events that take place on a specific date.
  3. Make a list of major non-writing commitments that take up your time.
  4. Note down when you’re travelling, or have time off.
  5. Set aside study time, on a daily, weekly, or monthly basis, depending on your aims.
  6. Consider how the seasons affect your life, and your writing. For example, do you feel drawn to a particular project at a certain time of the year?
  7. Consider planning a writing retreat.
  8. For large projects, write in your deadlines and work backwards, pencilling in important checkpoints or milestones.

Some Suggestions

  1. Know when a challenge is no longer serving you. The point of a challenge is to grow and improve, not to add more unnecessary stress and competition to your life.
  2. Track and review your progress at least once a month. This will help you with the previous point.
  3. At the end of the year, perform a more thorough self-assessment, especially if you’re considering writing as a career. This will also help you plan for the following year.

If you would like to track your challenge progress on paper, you might like The Productivity Pages, a bundle of 10 printable worksheets designed to help you plan and schedule your writing projects. Click here to download.

Click here to download The Productivity Pages - 10 worksheets to track your writing wins...