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4 Writing Lessons from J.R.R. Tolkien You Really Don’t Want to Hear

Annie Cosby
March 22, 2024 | 4 min read

The mastermind behind The Lord of the Rings and The Hobbit, JRR Tolkien is celebrated as one of the greatest fantasy authors of all time.

His work has inspired generations of readers and writers alike, including Ursula K. Le Guin and J. K. Rowling, shaping the landscape of modern fantasy literature. In addition to his iconic novels, people are fascinated by Tolkien's writing habits and how he managed to be so prolific within one human lifetime.

The Letters of J. R. R. Tolkien, published by Tolkien's son, Christopher, after his death provide a fantastic peek into the writer's personal life. Spanning more than six decades, the letters offer a chronological narrative of Tolkien's life and work. From his humble beginnings as a scholar to the towering figure of fantasy literature, Tolkien's correspondence reveals the evolution of his ideas and the challenges he faced in bringing his vision to life.

Hidden within these experiences is a treasure trove of writing advice writers probably don't want to hear. Let's explore four of these gems that challenge conventional wisdom: 

 

1. Sometimes you have to cut the grass.

One April letter from Tolkien reads:

"I managed to get an hour or two’s writing, and have brought Frodo nearly to the gates of Mordor. Afternoon lawn-mowing. Term begins next week, and proofs of Wales papers have come. Still I am going to continue 'Ring' in every salvable moment."

 

The man had just 1-2 hours of writing a day and some "moments" and still managed to generate half a million words for the Lord of the Rings trilogy alone? Yes, even literary greats had to deal with the real world on a daily basis.

In fact, Tolkien had many other responsibilities that pulled him away from his writing, such as work as a translator and professor. (He also helped during the creation of the Oxford English Dictionary.) But he didn't let that stop him.

P.S. Do you use generic working titles for your writing? It can't be more banal than using "Ring" to describe the sprawling fantasy epic that is Lord of the Rings!

 

2. Build the background.

Tolkien famously wrote extensive backgrounds to enrich his world-building. In one letter, he advises his son that "the tale should be more like a web than a chain." Perhaps the most impressive aspect of this web was Tolkien's fictional languages, including entire language families like Elvish and Dwarvish.

As a philologist, Tolkien was deeply familiar with the intricate nuances of words and their etymology. Tolkien's assertion is that delving into language creation not only enriched the world-building process but also lent authenticity and depth to his fictional cultures. Some of his languages even came before his books!

Now, we're not saying you need to create 15 different Elvish dialects. But we are saying that the richer the world-building, the more engaging the story. Tolkien is proof. 

 

3. It's not that deep.

If you're familiar with C.S. Lewis's relationship with Tolkien, you might know that Tolkien famously (and publicly) disliked allegory in literature. He and Lewis, though good friends, often butted heads about it.

Tolkien particularly hated when readers interpreted The Lord of the Rings as an allegory for World War II or other contemporary events. He vehemently denied any intentional allegorical elements in his work, saying:

"I cordially dislike allegory in all its manifestations, and always have done so since I grew old and wary enough to detect its presence. I much prefer history – true or feigned – with its varied applicability to the thought and experience of readers. I think that many confuse applicability with allegory, but the one resides in the freedom of the reader, and the other in the purposed domination of the author."

 

Some scholars say this dislike of allegory relates to why Tolkien disliked Dune, writing in a private letter in 1966:

"It is impossible for an author still writing to be fair to another author working along the same lines. At least I find it so. In fact I dislike Dune with some intensity, and in that unfortunate case it is much the best and fairest to another author to keep silent and refuse to comment."

 

Thought it's just as likely Tolkien didn't like Dune for other reasons — like its treatment of religion (he was a devout Catholic) or political and societal commentary.

 

4. Success doesn’t make this easier.

One of the most poignant aspects of The Letters of J. R. R. Tolkien is Tolkien's reflections on the impact of fame and the pressure of literary success.

Many writers imagine a future level of success where this whole "creating intimate worlds and releasing them to the public for consumption and ridicule" thing gets easier. But Tolkien is evidence that it doesn't work like that.

After the commercial success of The Lord of the Rings, Tolkien struggled to complete anything, revising the same stories over and over. (Sounds like he needed a Freewrite.) Tolkien is said to have worried that fans would be unsatisfied by stories not set in Middle Earth. He even wrote a few pages of a LOTR sequel before shelving it. When he died, Tolkien left behind a treasure trove of unpublished work.

At the end of the day, Tolkien's legacy serves as a reminder that true creativity must stem from a sincere passion for one's craft, rather than the pursuit of fame or fortune, in order to be sustainable.

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Whether you're a longtime fan of Tolkien's work or a newcomer to the universe of Middle Earth, Tolkien's writing life has left behind a legacy rich enough to inspire and enchant any writer.

What's your favorite aspect of Tolkien's legacy?

 

[RETURN TO “WHAT WRITERS CAN LEARN FROM JRR TOLKIEN.”]

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.

November 29, 2025 4 min read

The Great Freewrite Séance: A Ghost'ly Charity Auction Full Terms & Conditions

These Terms and Conditions (“Terms”) govern participation in The Great Freewrite Séance: A Ghost'ly Charity Auction (“Auction”), organized by Freewrite (“Organizer,” “we,” “us,” or “our”). By registering for, bidding in, or otherwise participating in the Auction, you (“Participant,” “Bidder,” or “Winner”) agree to be bound by these Terms.

1. Auction Overview

1.1. The Auction offers for sale a limited number of Freewrite Traveler Ghost Edition units (“Items” or “Ghost Traveler units”), each personally signed and drawn on by a featured author.

1.2. All proceeds, net of explicitly disclosed administrative costs, will be donated to the charity or charitable initiative (“Charity”) identified on each auction item’s page, as chosen by the respective author.

2. Eligibility

2.1. Participants must be at least 18 years old or the age of majority in their jurisdiction, whichever is higher.

2.2. Employees of Freewrite, the participating authors, or any affiliates directly involved in the Auction are not eligible to bid.

2.3. By participating, you represent that you are legally permitted to take part in online auctions and to pay for any bids you win.

3. Auction Registration

3.1. Participants must create an account on the auction platform or otherwise register using accurate, current, and complete information.

3.2. Freewrite reserves the right to verify identity and to disqualify any Participant who provides false or misleading information.

4. Bidding Rules

4.1. All bids are binding, final, and non-retractable.

4.2. Bidders are responsible for monitoring their bids; Freewrite is not liable for missed notifications or technical issues on the auction platform or the Participant’s device.

4.3. Freewrite reserves the right to:

  • set minimum bids or bid increments;
  • reject bids deemed in bad faith or intended to disrupt the Auction;
  • extend, pause, or cancel the Auction in case of technical difficulties, fraud, or events beyond reasonable control.

5. Winning Bids and Payment

5.1. The highest valid bid at the close of the Auction is the Winning Bid, and the corresponding Participant becomes the Winner.

5.2. Winners will receive payment instructions and must complete payment within 48 hours of the auction’s close unless otherwise stated.

5.3. Failure to complete payment on time may result in forfeiture, and Freewrite may offer the Item to the next highest bidder.

5.4. Accepted payment methods will be listed on the Auction platform. All payments must be made in the currency specified.

6. Item Description and Condition

6.1. Each Ghost Traveler unit is authentic, and the signatures, doodles, and messages are original works created by the participating author. These are authors, not artists. By bidding on the Item, you acknowledge that you are receiving a one-of-a-kind unit marked with unique art and messages and you agree to these terms and conditions.

6.2. Because Items are customized and signed by hand, variations, imperfections, or unique marks are to be expected. These are considered part of the Item’s character and not defects.

6.3. Items are provided “as-is” and “as-available.” Freewrite makes no warranties of merchantability or fitness for a particular purpose.

7. Shipping & Delivery

7.1. Shipping costs, import duties, and taxes may apply unless explicitly stated otherwise.

7.2. Freewrite will make reasonable efforts to ship Items within the estimated timeline but cannot guarantee delivery dates.

7.3. Title and risk of loss transfer to the Winner upon delivery to the carrier.

7.4. Freewrite is not responsible for delays, damage, or loss caused by the courier or customs agencies.

8. Charity Donation

8.1. Net proceeds from the Auction will be donated to the Charity designated on each Item page.

8.2. Donation amounts and recipients may be disclosed publicly unless prohibited by law.

8.3. Winners acknowledge that they are purchasing Items, not making a tax-deductible donation to Freewrite; therefore, Winners will not receive charitable tax receipts unless Freewrite explicitly states otherwise in compliance with applicable laws.

9. Intellectual Property

9.1. All trademarks, brand names, product names, and creative materials associated with Freewrite and the Ghost Traveler remain the exclusive property of Freewrite or their respective rights holders.

9.2. Participants may not reproduce, distribute, or publicly display the authors’ doodles without permission where such rights are applicable, except as allowed by law (e.g., resale of the physical Item).

10. Privacy

10.1. By participating, you consent to Freewrite’s collection, use, and storage of your personal data in accordance with our Privacy Policy.

10.2. Freewrite may publicly announce auction results, including Winner’s first name, last initial, city, state/country, and winning bid amount unless prohibited by law or unless you formally request anonymity when possible.

11. Prohibited Conduct

Participants may not:

  • engage in bid manipulation, fraud, or collusive bidding;
  • use automated systems (bots, scripts, scrapers) to place or monitor bids;
  • interfere with the Auction, platform, or other participants

Freewrite may ban or disqualify any Participant violating these rules.

12. Limitation of Liability

To the fullest extent permitted by law:

12.1. Freewrite is not liable for indirect, incidental, special, or consequential damages arising from the Auction or purchase of Items.

12.2. Freewrite’s total liability in connection with these Terms shall not exceed the amount of the Winning Bid actually paid by the Participant.

12.3. Freewrite is not responsible for technical malfunctions, internet outages, system failures, or other issues beyond its control.

13. Cancellation and Force Majeure

Freewrite may cancel, postpone, or modify the Auction due to unforeseen circumstances, including but not limited to natural disasters, system failures, strikes, or events affecting participating authors or the Charity.

14. Governing Law & Dispute Resolution

14.1. These Terms are governed by the laws of Michigan, without regard to conflict-of-law rules.

14.2. Any disputes arising under these Terms will be resolved through binding arbitration or the courts of the specified jurisdiction, as applicable.

14.3. Participants waive any right to participate in class-action lawsuits relating to the Auction.

15. Amendments

Freewrite may update these Terms at any time. Continued participation in the Auction after updates constitutes acceptance of the revised Terms.

16. Contact Information

For questions or concerns regarding the Auction or these Terms, contact: hello@getfreewrite.com.

November 25, 2025 1 min read

This is a great gratitude writing exercise to be done alone or in a group, with people of any age.

How to Play

    1. Designate someone to read out each prompt below. (Feel free to add your own prompts.)
    2. After each prompt is read, set a timer for one minute. (With younger kids, this can be shortened. For older folks who want to freewrite meaningfully, more time can be added.)
    3. Each person freewrites by finishing the sentence and elaborating until the timer goes off. (For little kids, this can be done verbally with an adult recording their answers. Hilarity will ensue.)
    4. Remeber that freewriting — allowing yourself to write with abandon — enables you to let go, tapping into your subconscious to explore your thoughts more deeply.
    5. When everyone is done with all the prompts, take turns going through some your answers. Some people may be eager to share. Others may not want to. Respect their decision.

The Prompts

  • I'm grateful for... [After you've finished this prompt, repeat it five times. Challenge yourself and others not to repeat a singe word with each new answer.]
  • The silliest thing I'm grateful for is...
  • The littlest thing I'm grateful for is...
  • The biggest thing I'm grateful for is...
  • The grossest thing I'm grateful for is...
  • One thing I love about myself is...
  • My favorite thing that happened this year was...
  • My hope for next year is...

This writing exercise has resulted in some sweet answers — and many hilarious ones, too. If you try it out, do let us know.

Write on.