Isak's Blog

In the 2010s, I heard Tim Ferriss share a phrase that guided his work: what would this look like if this were easy?

A question I’ve been asking myself this spring is: What if this were fun?

Most of my best work has come from doing something fun. It’s the rule of cool! Having fun is fun, and fun is contagious. You can tell when a writer is bored by their subject and putting no effort into making it more engaging or readable. You can also tell when a writer is having fun, like Bill Bryson or Hunter S. Thompson or Charles Portis.

I like to daydream about the perfect writing space. Usually it’s a cabin in the backyard with a desk, big windows, a shelf of books, a coffee pot, and — if I’m really treating myself — a wood stove and sleeping cot. Somewhere I can get away from all my cares, distractions, and worries to do good work.

It’s not really about the actual space. It’s the daydream that the space would unlock something within you, that you’d finally overcome your blocks and weaknesses to unleash your full creative potential. And in that way, it really is a daydream.

Happy Friday,

Cue the music, brew that pot. I’m having one of those weeks where I flip between creative procrastination and quick bouts of writing, which is my least favorite part of the process.

Here are 10 interesting things worth sharing this week:

1. This sketch gets exactly at why daily writing goals haven’t worked for me, because they prioritize quantity over quality. I’ve had better look making a goal to sit and write. Some writer said they can sit and write or sit and do nothing — but they aren’t allowed to sit and do something else. Good writing advice!
2. Braxton Haugen did a great job making writing look fun and exciting on his TikTok Tapes series back in 2021 (just scroll to the bottom of his profile and start there). I loved his Neistat-Sachs-inspired studio, the jazz, the typewriters, the Bob Dylan — the series is as good as I’d remembered.
3. Robert Caro having almost 1,000 pages of his fifth and final LBJ book is the best news I’ve had this week. His entire interview with C-SPAN was fascinating, especially how he can’t write until he knows the last line of the book.
4. “Remember what it was to be me: that is always the point.” I’m not able to consistently keep a journal but admire those who do, so I enjoyed Joan Didion’s essay on keeping a notebook to remember a past version of yourself and how you felt, not merely writing down events, thoughts, and observations.
5. I like reading quotes from creatives and artists, so @nitch on Instagram and @PoeticOutlaws on Substack are great — and both have a similar black-and-white aesthetic?
6. Ever wonder why composition notebooks have that iconic black and white speckled design? Well, this two-minute research party TikTok gets into how the design evolved and what it has to do with the lapwing bird.
7. Every spring the Kentucky Derby catches me by surprise and I celebrate by rereading Hunter S. Thompson’s essay about how the real event is the decadence and depravity of the elites that attend. This year, I listened to its word-by-word radio drama read by Tim Robbins (Shawshank Redemption) doing a passable impression of HST and Bill Frissell (Finding Forrester) composing — and an “All Things Considered” interview with illustrator Ralph Steadman.
8. I like Merriam-Webster’s “Word of the Day” newsletter to make my definitions more exact. They often hit that sweet spot of sharing words you can’t succinctly define but have heard and can use in daily conversation. Too many vocabulary resources share interesting and niche words you’ll rarely use.
9. I find electric typewriters to be a great middle-ground between the speed of computer typing and dexterous clunk of manual typewriters. Electric typewriters — again, hit that sweet spot — of speed where I can get my thoughts on the page at a reasonable speed, but not fast enough for lower-quality stream of conscious. So this video on the iconic IBM Selectric Typewriter has me curious about getting one with many diifferent typefaces.
10. Speaking of typefaces: I love old writing reference books from before the digital age. My mother-in-law shared her “Words Into Type” book when I started freelancing in 2019, and it’s fascinating to read how physical publishing used to work. Bonus: Mary Norris, the New Yorker’s Comma Queen, recommends it (I keep four reference books on my writing desk, and I’m delighted to learn they include her three recommendations).

See you on down the dusty trail,

Happy Friday,

Cue the music, brew that pot. Minnesota’s afternoon rainstorms have been perfect for reading, writing, and sitting on the couch.

Here are 10 interesting things worth sharing this week:

1. Funny how we assume the artists we look up to must be so literary, serious, and important compared to ourselves — then learn that’s exactly how they feel about who they look up to! I’m going to have to watch this entire Karl Ove Knausgård episode from BBC’s Arts in Motion.
2. Maria and I loved watching Desk Set last weekend, a 1957 rom-com about a whip-smart reference librarian and the computer engineer replacing her entire research department with a computer. Very funny, and unfortunately timely with AI!
3. I’ve been reading why people like Dante’s “Inferno” so much, so naturally I’ve been listening to Hozier’s “Unreal Unearth” album again and again.
4. “Oh Lord. I could talk about the various ways — in nature, in folklore, things like that — but honestly, the surest one? Spite.” T. Kingfisher on the surest way for him to find inspiration. This is my surest way, too! Austin Kleon recommends it, too.
5. I recently read “The Emerson Circle” and loved learning more about the Transcendentalists, but mostly Margaret Fuller, Louisa May Alcott, and Thoreau. Just in time to watch this new PBS miniseries on the Thoreau! Robert Gross’ book is up next to read.
6. “Well, I don’t have to worry about how to pay the mortgage. I get to write the stories I want to write.” Octavia Butler on the best parts about her success as a writer — the dream! I’m also an early-morning writer; by 5 p.m. my brain’s largely unhelpful and annoying.
7. I read the first Knaussgard book in 2016, and autofiction was this new, interesting genre to me. This week I revisited a LitHub article written by Robert Moor in 2024 (whose new book I’m v. excited to read) about the book “Bjarki, not Bjarki,” a great book about creativity, writing, and autojournalism.
8. Speaking of autojournalism: it’s starting to feel like summer, which means I want to float in a pool, drink gin and tonics, and read Hunter S. Thompson. Van Neistat likes him for his adventures and prose; I love him writing so politically and entertainingly.
9. Literary fly fisherman! I read “A River Runs Through It” in college in two days (molecules, molecules) and loved it. “Ninety-two in the Shade” felt like Norman Maclean meets Hunter S. Thompson. I’d add Callan Wink as a favorite modern literary fly fisherman, a form I hope continues.
10. We forget how much agency we have; you can just email people stuff. I’m not great at taking this advice often but it has worked well for me in the past.

See you on down the dusty trail,