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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

December 30, 2025 3 min read

It’s Freewrite’s favorite time of year. When dictionaries around the world examine language use of the previous year and select a “Word of the Year.”

Of course, there are many different dictionaries in use in the English language, and they all have different ideas about what word was the most influential or saw the most growth in the previous year. They individually review new slang and culturally relevant vocabulary, examine spikes or dips in usage, and pour over internet trend data.

Let’s see what some of the biggest dictionaries decided for 2025. And read to the end for a chance to submit your own Word of the Year — and win a Freewrite gift card.

[SUBMIT YOUR WORD OF THE YEAR]


Merriam-Webster: "slop"

Merriam-Webster chose "slop" as its Word of the Year for 2025 to describe "all that stuff dumped on our screens, captured in just four letters."

The dictionary lists "absurd videos, off-kilter advertising images, cheesy propaganda, fake news that looks pretty real, junky AI-written books, 'workslop' reports that waste coworkers’ time … and lots of talking cats" as examples of slop.

The original sense of the word "slop" from the 1700s was “soft mud” and eventually evolved to mean "food waste" and "rubbish." 2025 linked the term to AI, and the rest is history.

Honorable mentions: conclave, gerrymander, touch grass, performative, tariff, 67.

Dictionary.com: "67"

The team at Dictionary.com likes to pick a word that serves as “a linguistic time capsule, reflecting social trends and global events that defined the year.”

For 2025, they decided that “word” was actually a number. Or two numbers, to be exact.

If you’re an old, like me, and don’t know many school-age children, you may not have heard “67” in use. (Note that this is not “sixty-seven,” but “six, seven.”)

Dictionary.com claims the origin of “67” is a song called “Doot Doot (6 7)” by Skrilla, quickly made infamous by viral TikTok videos, most notably featuring a child who will for the rest of his life be known as the “6-7 Kid.” But according to my nine-year-old cousin, the origins of something so mystical can’t ever truly be known.

(My third grade expert also demonstrated the accompanying signature hand gesture, where you place both hands palms up and alternately move up and down.)

And if you happen to find yourself in a fourth-grade classroom, watch your mouth, because there’s a good chance this term has been banned for the teacher’s sanity.

Annoyed yet? Don’t be. As Dictionary.com points out, 6-7 is a rather delightful example at how fast language can develop as a new generation joins the conversation.

Dictionary.com honorable mentions: agentic, aura farming, broligarchy, clanker, Gen Z stare, kiss cam, overtourism, tariff, tradwife.

Oxford Dictionary: "rage bait"

With input from more than 30,000 users and expert analysis, Oxford Dictionary chose "rage bait" for their word of the year.

Specifically, the dictionary pointed to 2025’s news cycle, online manipulation tactics, and growing awareness of where we spend our time and attention online.

While closely paralleling its etymological cousin "clickbait," rage bait more specifically denotes content that evokes anger, discord, or polarization.

Oxford's experts report that use of the term has tripled in the last 12 months.

Oxford Dictionary's honorable mentions:aura farming, biohack.

Cambridge Dictionary: "parasocial"

The Cambridge Dictionary examined a sustained trend of increased searches to choose "parasocial" as its Word of the Year.

Believe it or not, this term was coined by sociologists in 1956, combining “social” with the Greek-derived prefix para-, which in this case means “similar to or parallel to, but separate from.”

But interest in and use of the term exploded this year, finally moving from a mainly academic context to the mainstream.

Cambridge Dictionary's honorable mentions: slop, delulu, skibidi, tradwife

Freewrite: TBD

This year, the Freewrite Fam is picking our own Word of the Year.

Click below to submit what you think the Word of 2025 should be, and we'll pick one submission to receive a Freewrite gift card.

[SUBMIT HERE] 

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Sources

December 18, 2025 7 min read

What can Jane Austen's personal letters teach writers of today?

December 10, 2025 6 min read

Singer-songwriter Abner James finds his creativity in the quiet freedom of analog tools. Learn how his creative process transcends different media.

Abner James went to school for film directing. But the success of the band he and his brother formed together, Eighty Ninety, knocked him onto a different trajectory.

The band has accrued more than 40 million streams since the release of their debut EP “Elizabeth," and their work was even co-signed by Taylor Swift when the singer added Eighty Ninety to her playlist "Songs Taylor Loves.”

Now, Abner is returning to long-form writing in addition to songwriting, and with a change in media comes an examination of the creative process. We sat down to chat about what's the same — and what's different. 

ANNIE COSBY: Tell us about your songwriting process.

ABNER JAMES: The way I tend to write my songs is hunched over a guitar and just seeing what comes. Sounds become words become shapes. It's a very physical process that is really about turning my brain off.

And one of the things that occurred to me when I was traveling, actually, was that I would love to be able to do that but from a writing perspective. What would happen if I sat down and approached writing in the same way that I approached music? In a more intuitive and free-form kind of way? What would that dig up?

AC: That's basically the ethos of Freewrite.

AJ: Yes. We had just put out a record, and I was thinking about how to get into writing for the next one. It occurred to me that regardless of how I started, I always finished on a screen. And I wondered: what's the acoustic guitar version of writing?

Where there's not blue light hitting me in the face. Even if I'm using my Notes app, it's the same thing. It really gets me into a different mindset.

 "I wondered: what's the acoustic guitar version of writing?"

I grew up playing piano. That was my first instrument. And I found an old typewriter at a thrift store, and I love it. It actually reminded me a lot of playing piano, the kind of physical, the feeling of it. And it was really fun, but pretty impractical, especially because I travel a fair amount.

And so I wondered, is there such a thing as a digital typewriter? And I googled it, and I found Freewrite.

AC: What about Freewrite helps you write?

AJ:I think, pragmatically, just the E Ink screen is a huge deal, because it doesn't exhaust me in the same way. And the idea of having a tool specifically set aside for the process is appealing in an aesthetic way but also a mental-emotional way. When it comes out, it's kind of like ... It's like having an office you work out of. It's just for that.

"The way I tend to write my songs is hunched over a guitar and just seeing what comes. Sounds become words become shapes. It's a very physical process that is really about turning my brain off."

And all of the pragmatic limitations — like you're not getting texts on it, and you're not doing all that stuff on the internet — that's really helpful, too. But just having the mindset....

When I pick up a guitar, or I sit down at the piano, it very much puts me into that space. Having a tool just for words does the same thing. I find that to be really cool and inspiring.

"When I pick up a guitar, or I sit down at the piano, it very much puts me into that space. Having a tool just for words does the same thing."

AC: So mentally it gets you ready for writing.

AJ: Yeah, and also, when you write a Microsoft Word, it looks so finished that it's hard to keep going. If every time I strummed a chord, I was hearing it back, mixed and mastered and produced...?

It's hard to stay in that space when I'm seeing it fully written out and formatted in, like, Times New Roman, looking all seriously back at me.

AC: I get that. I have terrible instincts to edit stuff over and over again and never finish a story.

AJ:  Also, the way you just open it and it's ready to go. So you don't have the stages of the computer turning on, that kind of puts this pressure, this tension on.

It's working at the edges in all these different ways that on their own could feel a little bit like it's not really necessary. All these amorphous things where you could look at it and be like, well, I don't really need any of those. But they add up to a critical mass that actually is significant.

And sometimes, if I want to bring it on a plane, I've found it's replaced reading for me. Rather than pick up a book or bring a book on the plane, I bring Traveler and just kind of hang out in that space and see if anything comes up.

I've found that it's kind of like writing songs on a different instrument, you get different styles of music that you wouldn't have otherwise. I've found that writing from words towards music, I get different kinds of songs than I have in the past, which has been interesting.

In that way, like sitting at a piano, you just write differently than you do on a guitar, or even a bass, because of the things those instruments tend to encourage or that they can do.

It feels almost like a little synthesizer, a different kind of instrument that has unlocked a different kind of approach for me.

"I've found that it's kind of like writing songs on a different instrument, you get different styles of music that you wouldn't have otherwise... [Traveler] feels almost like a little synthesizer, a different kind of instrument that has unlocked a different kind of approach for me."

AC: As someone who doesn't know the first thing about writing music, that's fascinating. It's all magic to me.

AJ: Yeah.

AC: What else are you interested in writing?

AJ: I went to school for film directing. That was kind of what I thought I was going to do. And then my brother and I started the band and that kind of happened first and knocked me onto a different track for a little while after college.

Growing up, though, writing was my way into everything. In directing, I wanted to be in control of the thing that I wrote. And in music, it was the same — the songwriting really feels like it came from that same place. And then the idea of writing longer form, like fiction, almost feels just like the next step from song to EP to album to novel.

For whatever reason, that started feeling like a challenge that would be deeply related to the kinds of work that we do in the studio.

AC: Do you have any advice for aspiring songwriters?

AJ: This sounds like a cliche, but it's totally true: whatever success that I've had as a songwriter — judge that for yourself — but whatever success I have had, has been directly proportional to just writing the song that I wanted to hear.

What I mean by that is, even if you're being coldly, cynically, late-stage capitalist about it, it's by far the most success I've had. The good news is that you don't have to choose. And in fact, when you start making those little compromises, or even begin to inch in that direction, it just doesn't work. So you can forget about it.

Just make music you want to hear. And that will be the music that resonates with most people.

I think there's a temptation to have an imaginary focus group in your head of like 500 people. But the problem is all those people are fake. They're not real. None of those people are actually real people. You're a focus group of one, you're one real person. There are more real people in that focus group than in the imaginary one.

And I just don't think that we're that different, in the end. So that would be my advice.

AC: That seems like generally great creative advice. Because fiction writers talk about that too, right? Do you write to market or do you write the book you want to read. Same thing. And that imaginary focus group has been debilitating for me. I have to silence that focus group before I can write.

AJ: Absolutely.

"I think there's a temptation to have an imaginary focus group in your head of like 500 people. But the problem is all those people are fake... You're a focus group of one, you're one real person. There are more real people in that focus group than in the imaginary one."

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Learn more about Abner James, his brother, and their band, Eighty Ninety, on Instagram.