How To Survive Your 30-Day Writing Challenge

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Photo by Kelly Sikkema on Unsplash

I wrote poetry in elementary school and won some prizes. Then I totally forgot about that when I reached high school and focused more on prose.

In college, I moonlighted as a copywriter and a rock journalist. I managed to build a decent portfolio.

For work, I eventually got paid as a technical writer, biographer, copywriter, and worked my way up to become a Presidential speechwriter at the age of 29.

But 5 years after that career zenith, I hit my financial nadir: a crushing student debt from my graduate school education.

I did not see writing as my way out. I did not see how writing could pull me out from the red quickly.

So I ventured into things that derailed me from my true calling. I focused on making money. I did things just for the sake of making money. I completely abandoned writing even though it was a source of joy.

That was in 2015.

I joined Medium in April 2019, at the suggestion of a former boss. I suddenly found myself in the virtual company of an intellectually positive crowd. The reads and the claps instantly made me feel welcome, and their absence made me want to work more. There was comfort in knowing that I had to earn each read and that if my work was not getting read, then I should work harder to improve my writing.

So it clicked. I found the ideal platform for me and found no reason not to be writing again.

And I did. Seriously and with intention.

In September, I embarked on a thirty-day writing challenge. I had never done anything like that, not even during my speechwriting years, so I happily embarked on a new adventure. What I gleaned from that experience continues to inspire and influence the way I write today.

Here’s what I did and how I survived it:

Read a book on writing while writing

I picked up a book on writing in the hopes of staying inspired throughout the journey. I have not taken any writing courses in school. I learned to write by writing, so I felt the need for a security blanket given my long hiatus from scribing.

Bird by Bird: Some Instructions On Writing and Life by Anne Lamott could not have been a better choice. Having a book designed to encourage a writer, amateur or otherwise, to “pay attention” and write “every day for a while” confirms why the 30-day challenge was a worthwhile endeavor. One could tell that Anne Lamott embraces the craft fully given her detailed observations that are absolutely true and downright funny. This book, with Anne masquerading as the writing professor I never had, made writing profoundly enjoyable, without the fear of prolific red marks on “shitty first drafts.” (Note: I will be sharing some helpful quotes from her book throughout this piece to help you with your writing the way she helped mine.)

Other books that were helpful in refining my writing style were Working by Robert A. Caro and Zen In The Art Of Writing by Ray Bradbury.

Read anything and everything

“Books help us understand who we are and how we are to behave.”

After I finished Bird By Bird, I mixed up my reading selection. I read a Pulitzer-prize winning novel, a memoir, a suspense thriller and have a bunch of non-fiction titles to go through. My goal was to let these books influence my writing and come up with ideas for new stories. This trick has so far worked.

One of the best tools for this is Scribd, which has an impressive selection of books and audiobooks.

Write about everything you know

“There are these stories and ideas and visions and memories and plots inside me, and only I can give birth to them.”

I did not have an editorial calendar of any sort and just dove in. In my first week, I was bursting with content after having just arrived from an epic 6-week vagabonding adventure across North America. But by the third week, the well was running dry. I was out of ideas, or so I thought.

When you are pushing forty and maybe speaking to a predominantly tech-savvy millennial audience, the mere thought of not having anything to say sounds criminal. I have dabbled in multiple industries throughout my career. I have collected a bunch of failures and milestones that remain unwritten but from which, I know, a lot of young people can learn. I have these nebulous ideas, accumulated over time and logged in smartphones and notebooks, but never really processed and stitched together into a relatable story. Writing here has changed that.

Schedule writing in the calendar and stick to it

“Rituals are a good signal to your unconscious that it is time to kick in.”

You know when your friends invite you for dinner sometime but never follow that up with an exact date and time? You also know that that dinner is not going to happen.

It is the same for writing. It requires a commitment that eventually becomes a ritual. It should be in your daily schedule. Otherwise, it would be easy to dismiss when work meetings and household errands start getting in the way.

What works for me is writing in the morning, ideally from 7 AM to 11 AM, with my phone’s DND function turned on. It is highly unlikely that a work-related disaster is unfolding at that time, so I give the morning to invest in myself, and face the world at noon. I understand that this level of flexibility is not available to many people, who might only have the opportunity to write at night. Just stick to a schedule that works, ideally with a calendar notification that will push you to write regularly.

View all stories as building blocks

“The purpose of most great writing seems to be to reveal in an ethical light who we are.”

Not all stories are viewed and read, and it can be disappointing, so the trick here is to change your mindset.

Our writing is an extension of who we are. It is steeped in our values and beliefs, reaped from the cornucopia of pleasures and failures we have experienced through the years. Not a single piece should be a cause of embarrassment, otherwise, why publish it in the first place?

We have to write about what is important to us, what we might be curious about and what we would like to understand. There is no mystery formula. When you do this and do it every day, you are writing stories that could be used as building blocks for, say, a travel memoir or a non-fiction tome you could publish in the future. No one really knows where the wind will blow, so those stories that may not have done very well could just be gems in the making.

Thank people you admire

“You are going to have to give and give and give, or there’s no reason for you to be writing.”

When touched by something I have read or heard on a podcast, I note that down and find a way to express my gratitude to the person, no matter how powerful or important they seem to be. This comes from knowing how much of themselves they gave to that piece of art. It is admittedly not something I do often, but I honestly try. You know why? If I had written something that some person in, say, Fiji had found useful, and she takes the time to send me her thanks, I know I have already made this world a little bit better than when I found it. What could be a better purpose for living?

I have written to a few famous celebrities, authors and professors and surprisingly, my response success rate is at roughly 80%. I have also gotten some feedback from random people expressing their admiration for my writing. It is the fuel that keeps me going, but I had to give first.

Share the friend link on social media

“Toni Morrison said, ‘The function of freedom is to free someone else,’ and if you are no longer wracked or in bondage to a person or a way of life, tell your story.”

I have approached this strategy with some delinquency (all my free time now is devoted to writing) but if you want to monitor traction for your stories, this practice helps. The all-consuming Medium stats page will tell you on which platforms your friend links get read and if you probe deeper, a basic profile of your readers. This helps in developing story ideas that interest you and could be interesting for them too.

Post on your website if you have one and then share on all your social networking platforms. Tag companies or individuals who were mentioned in your think piece. They will be grateful, and might even repost or retweet to repay your kindness. That should earn you new followers. Share freely because you do not know who might benefit from your art.

Forgive yourself when writing is impossible

“Your unconscious cannot work if you are breathing down its neck.”

If writing is a full-time job, there could be less room for remorse. But to most writers like myself who are invested in other things, give yourself a break whenever ideas or time seem scarce.

There will be a week’s worth of super-packed days. I had to pay that off with additional days when the schedule was more permitting. I would also do a series on the more hectic days. Lately, I have been writing poetry daily — a habit inspired by Ray Bradbury.

I have found that dipping my fingers into many things — music, travel, food, consulting — provides more than enough material to write about. Doing other things besides writing helps with my writing. A recent trip to India, for instance, distanced me from writing but mesmerized me for 10 days. I believe that is called inspiration, the writer’s so-called muse.

Get featured on publications

“You are lucky to be one of those people who wish to build sandcastles with words. This is what separates artists from ordinary people: the belief, deep in our hearts, that if we build our castles well enough, somehow the ocean won’t wash them away.”

The more I wrote, the more I discovered what my niche was, and what I could be writing on extensively in the future.

I was quite honored to have been invited to publish my stories on The Startup, which has 500K+ followers. That helped with increasing my readership, building my confidence and creating momentum. The Age of Awareness supports my environmental advocacy by publishing my work on the subject.

It does not end there. I share some of my work here with journalists in my country, who are constantly on the lookout for evergreen articles. Some topics on some days may seem mundane or repetitive, but remember that what makes the written work unique is the writer’s perspective. It is the writer’s job to make the facts, the stats and the stories she is weaving interesting, so do not leave out your personality in your work.

I hope you found this useful! If you have any questions, please sign up on my website here.

Written by

Former presidential speechwriter, still a musician; writes about urban gridlocks. Will work full time for the planet. Harvard Kennedy School ‘14 🇵🇭

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