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How I (Finally) Overcame a Lifetime of Writer’s Block

Reese Hopper
September 20, 2024 | 5 min read

On December 31, 2021, I published my 465th blog in 465 days. I successfully wrote and published an article every single day for an entire calendar year — plus one hundred days on top of that.

But it wasn’t always like this. I used to be a serial quitter.

Everything changed for me by accident. A few years before this blogging streak, in 2018, I posted a picture on Instagram with the caption, “[I’m] thinking of blogging every single day in November no matter what, do you think I can do it?”

I didn’t realize it at the time, but that silly Instagram post had everything I needed to overcome a lifetime of writer’s block and create a repeatable system that helps me execute creative ideas.

The Issue

I was always the classic example of an “idea guy.”

All ideas. Little execution. No consistency.

Here’s how it used to go for me: an idea strikes like a lightning bolt. Inspiration rattles through my very bones. I decide I will chase my new dream every day. So I create for six or maybe seven days. Then, inevitably, difficulties arise. I’m hit with an especially busy day, or writer’s block finally strikes, or a collaborator cancels on me. My brain begins to believe that I signed up for a lifetime of difficulty with no upside.

So I quit. It’s the only logical conclusion!

What was happening here?

I wasn’t clearly defining my creative act. I was making indefinite commitments. I was renegotiating with myself. And I wasn’t involving my community.

The Accident

When I shared my Instagram post in 2018, I didn’t realize it accidentally had all the elements I needed to overcome my creative inconsistency. Let’s break down the caption. “[I’m] thinking of blogging every single day in November no matter what, do you think I can do it?”

Clear Definitions

The first part, “[I’m] thinking of blogging” was an essential definition of the creative act. Notice I didn’t say “I’m thinking of becoming a writer.” That would have been too broad — too bold to believe. But I had written blogs before. They were easy. They were achievable.

“Definitive, specific plans tend to get accomplished while vague assertions wisp weakly into the wind,” author Donald Miller writes in his book Hero on a Mission. “Why? Because vague and elusive notions do not help us find narrative traction.”

When we create small, daily commitments, our ability to begin and maintain momentum increases.

Definite End Dates

The second part, “every single day in November” carried a definite end date for the creative streak. Instead of committing forever to a creative lifestyle I knew next to nothing about, I set a definite end date. Even if things got hard, I knew I wouldn’t have to endure pain with no benefit forever.

Kristen Berman at the Common Cents Lab found a 24% increase in job applications when she set a deadline. Others, at the Journal of Marketing Research, discovered that 10% of people redeemed a bakery gift certificate that was good for two months — meanwhile, 30% of people redeemed the same gift certificate that was only good for two weeks!

How does this make sense? How do people accomplish more when they have less time? When we have a long time, we procrastinate. Short time frames and hard end dates increase the velocity with which we approach projects, as well as our motivation to overcome obstacles.

Non-negotiable Commitments

The third part, “no matter what,” was a non-negotiable commitment to the creative act. It didn’t matter if I was busy that day. It didn’t matter if I had no inspiration, or if something came up, or if the blog wasn’t good. I had to publish anyway.

“[Even] if I don’t feel inspired, I need to move forward,” said The Alchemist author Paulo Coelho in an interview. “I say, ‘You, book, are fighting with me. Okay. I’m going to sit here, and I’m not going to leave you alone until I find my way out of this crossroads.’”

Angela Duckworth, author of the book Grit, uncovered the common ground between graduates of the grueling military academy West Point. It wasn’t IQ. It wasn’t physical size or strength. It wasn’t prior education. It was grit. Graduates more often identified with the statement “I finish whatever I begin.”

By not allowing ourselves off the hook of our short-term commitments, and pushing through the hard stuff, we’re able to string together meaningful creative acts.

Public Commitments

Finally, the last part, “do you think I can do it?” I asked my community what they thought. I presented my commitment to the public. I staked a portion of my reputation on it. I was no longer an undiscovered genius or a secret artist. I made a promise to the people!

“‘I’m always on time, and I always show up to things, so why don’t I do that for myself?’” said Netflix comedian Mike Birbiglia in an interview. “So I put a hand-written note next to my bed that said … 'Mike! You have a meeting at Cafe Pedlar … at 7 a.m. with your mind!’”

Functional people find a way to show up for work, pick up their kids, and arrive at appointments, even when they don’t feel like it. But so many of us struggle to follow through on these same commitments to ourselves. By making a private commitment public, we increase the friction of failure, and with it, our chances of success.

“I’m always on time, and I always show up to things, so why don’t I do that for myself?” said Netflix comedian Mike Birbiglia in an interview. “So I put a hand-written note next to my bed that said … 'Mike! You have a meeting at Cafe Pedlar … at 7 a.m. with your mind!’”

The Process

If you want to start a creative streak of your own, follow this process:

  1. Define a small creative act you can accomplish every day—ideally, it only takes 30-45 minutes.
  2. Commit to a short-term streak with an end date — 7, or 15, or 21 days is great!
  3. Whatever you do, don’t miss a day in the streak. The days when you create anyway, even with no inspiration, are the moments you prove to yourself that you can overcome writer’s block.
  4. Tell your family, friends, and audience about your commitment to the streak. Share your work!
  5. Stop to reflect after your streak is over. Think about what you liked, what you learned, and how you can do it again, only longer.

With each successful creation streak, you’ll gain confidence. You’ll get better at defeating writer’s block. You’ll make good work.

But most importantly, you’ll transform from an “aspiring” creative… to a real one.

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Sources

September 10, 2025 3 min read

The Freewrite 500 Writing Contest — Terms and Conditions

Last Updated: 10-09-2025

By submitting an entry to The Freewrite 500 Writing Contest (the “Contest”), you agree to abide by the following Terms and Conditions.

1. Organizer

The Contest is organized by Freewrite, a brand owned and operated by Astrohaus, Inc. (hereinafter referred to as “Freewrite”, “we”, “our”, or “us”).

2. Eligibility

  • The Contest is open to individuals who are 18 years of age or older at the time of entry.

  • Employees of Freewrite, the Flash Fiction Institute, and their immediate families are not eligible to enter.

  • Void where prohibited by law.

3. How to Enter

  • Entries must be submitted through the official entry form to be made available on Friday, September 22.

  • Entries must be original works of flash fiction no longer than 500 words.

  • Only one entry per person is allowed.

  • Entries must be written in English.

  • The deadline for submission is 11:59 p.m. EST on September 22, 2025. Late or incomplete entries will not be accepted.

4. Entry Requirements

  • Submissions must be the entrant’s own original work and must not have been previously published, including on personal blogs or social media.

  • Entries must not contain any material that is obscene, offensive, defamatory, or otherwise inappropriate.

  • By entering, you confirm that your submission does not infringe on any third-party rights, including copyright, trademark, or privacy rights.

5. Judging and Winner Selection

  • All eligible entries will be judged by a panel of reviewers affiliated with Freewrite and the Flash Fiction Institute.

  • Judging criteria include length, creativity, and adherence to theme, and overall quality of writing.

  • The winner will be notified via email.

6. Prize

  • The winning entry will be published on both the Freewrite Blog and the Flash Fiction Institute Blog.

  • The winner will receive recognition across Freewrite and Flash Fiction Institute's social media platforms.

  • No cash prizes will be offered. Prizes include a Freewrite Traveler, a Words Are Hard writing prompt deck, publication on the Freewrite blog and the Flash Fiction Institute blog, and a free flash gym session hosted by the Flash Fiction Institute.

7. Rights and Usage

  • By entering the contest, entrants grant Freewrite and the Flash Fiction Institute first publication rights. This means Freewrite and the Flash Fiction Institute have a non-exclusive, royalty-free, worldwide license to publish, reproduce, and distribute the submitted entry in connection with the promotion of the Contest, including on their websites, blogs, email newsletters, social media channels, and more.

  • After initial publication, all rights revert back to the author, who is then free to republish or distribute their work elsewhere. However, we request that any subsequent publication acknowledges Freewrite and the Flash Fiction Institute as the original place of publication.

  • The winning author will be credited by name or preferred pen name when their work is published.

8. Privacy

  • Personal information collected during the entry process will be used only for the administration of the Contest and in accordance with Freewrite’s Privacy Policy.

  • Entrants may be contacted by Freewrite regarding their submission or related opportunities.

9. Disqualification

Freewrite reserves the right to disqualify any entry that:

  • Violates these Terms and Conditions,

  • Is found to contain plagiarized material,

  • Is deemed offensive or inappropriate,

  • Is submitted by someone ineligible.

10. Limitation of Liability

Freewrite is not responsible for:

  • Lost, late, incomplete, or misdirected entries;

  • Technical failures of any kind;

  • Any injury or damage to persons or property related to participation in the Contest.

11. Governing Law

These Terms and Conditions shall be governed by and construed in accordance with the laws of the State of [Insert State], without regard to its conflict of laws principles.

12. Contact

For any questions regarding the Contest, please contact us at:
📧 hello@getfreewrite.com.

September 10, 2025 1 min read

One blank page. 500 words. Zero fear. Let’s see what happens when you stop thinking and just go. It's the Freewrite 500, presented in collaboration with the Flash Fiction Institute.

August 22, 2025 3 min read

Most of us are surrounded by screens all day. To get your writing done, take writer Shannon Liao's advice and unplug.