What I Learned From Writing For 100 Days Straight

Image and challenge provided by Austin Kleon. Check it out

Last night I completed my 100 day writing challenge. For over three months, I plopped down by my laptop and hammered out at least five hundred words.

I did this under the pretense that showing up every day would make me a better writer — or at least suck a little less (see image above).

Did the challenge help achieve this goal? I like to think so, but I’ll leave that to the discretion of the reader.

The experience did teach me a few lessons about building a writing habit, coming up with ideas, and managing the highs and lows of the creative process. These lessons helped me complete my project, and I believe fellow writers will find them useful.

Below are the seven lessons I learned from writing for 100 days straight.

Lesson 1: Set An Attainable Writing Goal

Consistency and managing expectations: this remarkably unsexy duo is the key to sustaining a daily writing habit.

When setting a goal, it’s tempting to be ambitious. We imagine how much we’d write if we woke up with a full tank of energy and a free schedule, then use that as a target.

This is simply not realistic. Most days you will not roll out of bed eager to work. On the days you do, you will often find yourself hampered down with real world responsibilities: deadlines, errands to run, screaming kids.

Instead of thinking about how much you’d write on a perfect day, consider how much you could get done on a bad day — and make that your goal.

Don’t freak out if your benchmark seems small. Remember this is simply a minimum requirement, there is nothing stopping you from writing more.

For the challenge, I set a goal of either an hour of writing or 500 words. These numbers aren’t sacred, they are simply what worked with my schedule. You’re welcome to increase or shrink them to your liking.

Lesson 2: They’ll Be Duds Along The Way

With a week left in the challenge, I made the regrettable choice of reading some of my old posts. Poor decision! I ended up quarreling with my work and cursing the past version of myself foolish enough to publish it. I almost gave up with 7 days left.

It’s natural for writers to be embarrassed by past work. Most of the time this embarrassment is an overreaction — a healthy sign of your improvement. However, occasionally you’ll unearth a dud — a certified stinker, you’re ashamed to have written.

If you find one, don’t freak out. Duds are part of the process. Both beginners and accomplished authors make them — If you don’t believe me, look at your favorite writer’s body of work. I can guarantee there’s at least a dud or two in there.

We like to believe progress is linear, that each item we put out must be better than the last. This isn’t the case. For factors unknown and often out of your control, we can’t always churn out our best work.

If you’re feeling down about something you wrote, remember the mindful mantra: Simply Begin Again. Forget the past. Each project affords a new opportunity to restart and try again.

Lesson 3: Favor Exciting Ideas Over “Good” Ones

I swiped this piece of advice from Pixar Director Pete Docter. There’s a common belief that good writing is the natural result of a good idea. This misconception causes some to hunt for the “perfect idea” rather than sitting down to write.

In reality, an idea that seems “too good to fail” is an ordinary idea that someone took the time and care to mold into something great. Focusing too much on the idea itself ignores the tough work that went into it.

I’ve found the best way to endure this tough work, is to tackle an idea that excites you. One you’d be happy to write about, whether it succeeded or failed.

Keep this in mind when choosing which project to start on. Use excitement as the criteria for your choice, and avoid lumping ideas into categories like “good” or “bad”.

Lesson 4: Treat Writing And Editing As Separate Activities

This is one of the stock pieces of advice I’d filed under “good to know” and never implemented. But after seeing personal heroes like Jerry Seinfeld emphasize the distinction, I made a point to remind myself:

Writing and editing are not the same things and should not be treated as such.

Writing is free flowing. Your goal is to get ideas on the page in their crudest form — misspellings and typos be damned! In this phase the audience has not entered the fray, your work is for you and you alone.

Editing is exacting. You’re paring and pruning your work into something readable for an audience. In this part of the process you’re concerned with grammar, punctuation, and coherence.

Since the two are separate activities, I recommend focusing on one or the other during your writing sessions. Avoid editing while you write and writing while you edit.

Something I’ve found helpful is using different programs for the two phases. For writing, I use a word processor with spelling and grammar suggestions turned off — nothing sucks you out of the flow of writing like seeing clusters of squiggly lines on a page.

When I’m finished, I’ll paste my work into a program like Grammarly or ProWritingAid to edit.

Lesson 5: Give Your Readers A Reason To Care

When a reader clicks on something you wrote, a single question is looping over in their mind.

Why should I care?

You may have a knee jerk reaction to this: How dare they! People should judge my work on its own merits. How can someone be so egotistical?

But think about it from their perspective: anyone with an internet connection has an endless stream of content to choose from, why should they give you their attention without a reason to care?

A “reason to care’’ is a promise to your reader. A promise that your work is worth their time. This promise can come in many forms: a solution to one of their problems, a distraction from their dull drum life, a story that will amuse and entertain them.

Whatever the reason, say it loud and say it up front. Reassure your audience they have something to gain by reading on.

Lesson 6: Make Peace With Your Neuroses

If you’ve chosen the tiresome, difficult, maddening — and occasionally satisfying vocation of writing, I’m guessing you have a quirk or two.

These peculiarities often fuel your work, but other times they give you the urge to rip out what little hair you have left, and toss your computer off the 3rd floor balcony.

You may look for strategies to outwork or outwit your neuroses. But over the last 100 days, I’ve found it’s better to make peace with them. They’re a part of your personality, you couldn’t will away these mental ticks if you wanted to. Try to work with rather than against them.

Are you most productive past midnight? Good! Scribble away as the world is asleep.

Do you do some of your best writing on the toilet, as I do? Even better! Get to work with your draws down.

Must a treasured toy or trinket watch over your shoulder as you write? No problem! Let your guardian angel’s watchful eye aid your endeavors.

Ask around. There’s “no one size fits all” way to write. Each author, you included, may have an odd-ball way of going about things. If this suits you, stick with it! Let your work speaks for itself.

Lesson 7: Write For The Long Game

Marking the 100th “X” on my calendar brought about a bittersweet feeling. On one hand, I was proud I’d completed the challenge — writing every day is hard for a couple weeks, and even more difficult over a three-month period.

However, completing my chart reminded me how much work I had left to do. During the daily grind, 100 days feels like forever. But when it’s over, you realize it’s a blip in time.

Becoming a better writer, or mastering any skill, is a lifetime project. It takes years to feel comfortable, and decades to get “good” — however you define that. Author David Sedaris says he wrote every day for 15 years before getting published.

As you move forward, you’ll likely come across an infuriating truth: progress is undetectable. It occurs so slowly, it’s difficult to notice. And when you do, it rarely occurs in the way you expect.

If you dare to write, know you are running a marathon and not a sprint. Growth means incremental gains over a long period. Making these small strides requires a leap of faith — an ability to truck on, often when you feel you’re not making any headway.

The sooner you accept this, the sooner you can get to work. So stick around. Look ahead. And keep playing for the long game.

*** Note: If you’re interested in starting a 100 day challenge here’s a link to the chart I used. If you want to start smaller here’s a link to the 30 day version.



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Antonio Rengel

Antonio Rengel

Educator and Copywriter Who Writes About Creativity, Marketing, Pop Culture, And Occasionally Mindfulness Meditation