Written by Hurley Winkler

In graduate school, I wrote every day. I typed away (and snacked a lot) every morning and weekend to meet my creative writing program’s requirements. I produced thousands of pages of work in those two years of school, thanks to strong coffee and strict deadlines.

Nothing stokes my adrenaline-fueled fire more than a tight deadline. But school doesn’t mimic real life. Writing isn’t the same when no one’s expecting you to finish it—such as, a professor you respect and want to impress. Real-life writing requires discipline. My master’s degree may have bulked up my resume, but it didn’t have the same effect on my discipline— something I’ve learned can’t really be taught.

After graduating, I stumbled on Gretchen Rubin’s Four Tendencies framework. The author of “The Happiness Project” has broken work styles into four clusters: questioners, obligers, upholders and rebels. When I took Rubin’s quiz and read about obligers, I felt like she was speaking directly to me.

Obligers like me rely on outside expectations in order to check boxes and reach goals. In other words, we thrive on accountability. When an obliger needs to exercise, we’ll take a class or jog with a friend rather than hitting the gym alone. When we want to finish essays and short stories, we crave deadlines.

I thought my need for deadlines would be my downfall as a writer in the real world. Instead, learning to value that need has been transformative. I'm responsible for implementing my own accountability measures, whether it’s swapping pages with a friend, meeting a submission deadline or documenting my daily word counts on social media. Putting these accountability measures in place is my discipline.

In my social media circle, I’ve watched friends embark on 100-day challenges, where for 100 consecutive days, they’ve improved their push-ups, learned to play the piano and even finished their novels. As a newly realized obliger, I was hungry for that kind of accountability. 100 days is a long time to pick up any habit, but it’s still temporary—just long enough to form more positive habits.

I started my own 100-day writing challenge on Instagram in late July, writing 1,000 words a day for 100 consecutive days. I learned how to make writing a priority. I’d look at my week and insert slots for writing—something I did before the challenge, too, but this time, I actually began at the scheduled time and didn’t finish early. In 100 days, I revised short stories, drafted new essays and wrote dozens of journal entries.

Some days were more productive than others. More than once, I wrote, “If I wasn’t doing this damn writing challenge right now, I’d definitely go to bed.” Through those moments of drowsiness, I’d somehow persevere. My friends would comment on my daily word count posts with you-can-do-its and applause emojis. Every bit of it helped me push into the next day’s words.

My 100-day challenge taught me to sacrifice compulsive laziness. Instead of allowing my brain to say, “You’ve had a long day, so just lay on the couch and watch an entire season of The Office!” I’d tell myself. “Let’s unwind with some journaling and a glass of wine instead.” Trading a project, like a short story or essay, to journal for half an hour felt like a luxury.

If you’re an accountability-loving obliger like me, the act of embarking on a challenge—whether it’s an writing challenge like mine, a fitness challenge or even a cooking challenge—and documenting it on social media may push you to meet goals and change habits in the long run. Here are some tips to begin your own 100-day challenge:

1. Identify a specific habit or ability you’d like to sustain

The task you assign to yourself for 100 consecutive days should feel worthwhile in the long run. Relate your task to a goal you tend to put off. For me, that task wasn’t just writing every day, but writing more than just a couple hundred words at a time. Perhaps you practice drawing every day, but you’ve put off learning digital illustration—in that case, embark on a ProCreate challenge! Or if everyone in your yoga class is standing on their hands while you’re still doing shakti kicks, it’s time for a handstand challenge. Focus on one specific variable during your 100-day challenge to set yourself up for success.

2. Pick a goal that’s realistic, but still challenging

Your daily goal should push without punishing. Most days, reaching 1,000 words was a stretch, but I still managed to get there 100 days in a row.

3. Select a social media platform that makes sense to you

I chose Instagram because it’s the platform I keep up with most. Plus, my personal cheerleaders—my husband, my best friend and even my mom—are all on the ‘gram. While a writing challenge may have made more sense on Twitter or even Facebook, I was eager to have friends and family come along for the ride. It added to the accountability aspect.

4. Allow yourself some flexibility...

When doing the same thing for 100 days straight, burnout is right around the corner. To combat this, I let myself write about anything as long as it amounted to 1,000 words. Sometimes, I’d journal and make lists, and while that never felt like the most productive work, it never felt like a waste.

4.5 ...but make sure the challenge is productive

We embark on these types of challenges because we have goals to reach. I carved out three time slots per week to focus on my main goal: completing pieces of writing. If a finish line time slot popped up in my Google Calendar, I’d work on getting one piece of incomplete writing closer to the—you guessed it!—finish line. These time slots proved incredibly useful, but they only worked because I didn’t plan for them every day. Not only did I need the space between finish line sessions to keep myself motivated, but I also needed time to mull over the problems I was having with my work.

I used to beat myself up for not working on what I “needed” to be working on every single day. But I’m not a robot; I can’t force myself to be my most productive all the time. I’ve proven to myself that I can get work across the finish line when I get in the zone three times a week. Plus, journaling or working on new ideas during those other four days helps with the nitty-gritty.

5. If it’s working, keep going

If I was on a roll and had the time to keep writing, I’d just write! One day, I wrote over 3,000 words and couldn’t believe my eyes. After that day, a couple friends said, “That means you don’t have to write for two days since you wrote three day’s worth!” But why would I take a shortcut if I didn’t need one? After all, the habit I want to sustain is the sustainability itself. I won’t let myself cut corners.

Once you’ve completed your 100 days, find a way to sustain the momentum into your everyday life by setting stretch goals for yourself. Now that my challenge is over, I’ve decided to keep the momentum going by participating in my very first NaNoWriMo, or National Novel Writing Month. Throughout the month of November, thousands of writers all over the world are cranking out full-length novel drafts. For me, that means writing 50,000 words in just 30 days—a feat that seemed impossible before I finished my 100 Day Challenge.

Through this challenge, I’ve proven myself to myself. I’m capable of holding myself accountable to finish my work. And there’s no greater feeling than capability.

Hurley Winkler is a writer from Jacksonville, FL. Her essays and short stories have appeared in Bridge Eight’s 15 Views of Jacksonville anthology, Folio Weekly, Jacksonville Magazine, and others. She works for the Jacksonville Public Library, where she hosts the podcast Completely Booked. Hurley holds an MFA in Creative Writing from Lesley University. She coordinates the official Babes Who Hustle book club. Follow her everywhere: @hurleywink.