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.

--

Sources

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We're just 10 weeks away from a major milestone: the 10th anniversary of Freewrite's launch on Kickstarter.  On December 10, 2014, we introduced the Smart Typewriter, then known as  "Hemingwrite," to the world.
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In September of 2014, co-founders Adam Leeb and Patrick Paul entered Hemingwrite into the “Insert Coin” hardware competition sponsored by Engadget. Described as a new digital consumer product for distraction-free writing composition, Hemingwrite aimed to deliver a singular focus on a productive writing experience. A decade later, that core mission remains unchanged.
Hemingwrite was one of 20 inventions competing that week, highlighting early-stage hardware startups from around the world that had not yet received funding or shipped to consumers.
"What the Kindle did for reading, we want to do for writing," said co-founder Patrick Paul at the time."We set out to deliver the same distraction-free writing experience of a typewriter with all of the added benefits of modern technology."
Co-founder Adam Leeb added,  "We combined all of the best aspects of the typewriter, theMoleskine, and the computer to create a modern classic."
Althoughthe Hemingwrite concept  didn’t win the competition,  the initial coverage by Engadget led to another press hit and then another and quickly it became a viral sensation around the world. The project was covered in everything from The Wall Street Journal to The Atlantic. Over 125,000 people came to the simple wordpress website at hemingwrite.com and over 8,000 anxiously input their email asking for updates on the project.
Adam and Patrick knew they had something special on their hands but weren’t sure if anyone was willing to pay for this idea or if it was simply interesting. On December 10, 2014 the Kickstarter campaign was launched and immediately the pledge dollars started rolling in. Within 20 hours of launch, the campaign had raised over $200,000! And just like that, the Hemingwrite distraction-free writing tool concept became destined for reality.
How It’s Going
Since that initial launch, we have developed Freewrite into a family of distraction-free writing tools with three distinct models, Smart Typewriter, Traveler, and Alpha. Each has their distinct personality, but the core value of maximizing writer productivity runs throughout. 
In 2020, The original Freewrite Smart Typewriter became part of the Science Museum, London’s permanent Printing & Writing Collection.
The name Hemingwrite was dropped in 2015 and then revived in 2021 with the Ernest Hemingway Special Edition Smart Typewriter in partnership with the Ernest Hemingway Estate. 
We’ve created Sprinter for distraction-free writing in any browser and WTF where thousands of people every week receive a writing prompt and participate in Writing Time Friday. 
The community's achievements over the past decade have been  astounding:
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  • Collectively,users have written more than 605 million words (equivalent to over 6,000 novels!)
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We are extending our warranty that covers manufacturer’s defects to a full year on all Freewrite devices. This means you can enjoy your Freewrite with even greater peace of mind, knowing that we've got you covered for an entire year. 

For more information, please visit our dedicated article on our new warranty policy here: Introducing Freewrite's New 1-Year Warranty: Our Commitment to You
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As of October 1, 2024, we are extending our standard warranty that covers manufacturer’s defects to a full year on all Freewrite devices. This means you can enjoy your Freewrite with even greater peace of mind, knowing that we've got you covered for a full 12 months from the date of shipment. We’re even retroactively applying the warranty extension to purchases made this year.

Here is how our new 1-year warranty will work:
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    • For example, if your device shipped on March 1, 2024, with a 2-year Extended Warranty:
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      • Your 2-year Extended Warranty coverage will begin on March 1, 2025, and continue until March 1, 2027.



Your trust in our products is paramount to us, and this warranty extension reflects our dedication to your satisfaction and our confidence in the quality and reliability of our devices.

Thank you for choosing Freewrite; we look forward to serving you for many years to come. Write on!

 

- The Freewrite Team



Important Notes:

  • For devices purchased in 2023 or earlier, the original 90-day warranty applies, in addition to any paid Extended Warranty coverage.
  • If you purchased your device in 2023 or earlier, without an Extended Warranty, unfortunately, your warranty has now expired.
  • We are unable to offer refunds for prior out-of-warranty repairs.

 

Useful Links:

Official Freewrite Warranty Policy

Warranty Support Doc