Total: 89 posts
Posts in: newsletter
- Do something as cheaply as possible.
- Do something as quickly as possible.
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Do milestones make up for writerly failures?
I can't tell you if I reached most of my goals in 2025, for one simple reason: I forgot what goals I even made at the beginning of the year. And, somewhere in our latest pass around the sun, I deleted the (digital) paper trail.
But what about that one …
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Are imprecise tools an artist's best friend?
I used to watch a YouTube artist who was a fan of using oversized paint brushes on his canvases. He argued that being precise with imprecise tools led to interesting errors.
A YouTube short of tobysketchloose
In the world of painting, I agree 100%.
But …
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As if you have only 12 years to live
What if what frightened you could instead motivate you?
What if you could not only accept your biggest weakness but also somehow turn it into a strength?
These are some of the questions I've been asking since I heard a certain point on Mark Manson's …
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BE WARY OF AI'S POTENTIAL
What to expect...
Tone: outside voice
Snark level: it's surely there somewhere
Other special provisions: another post criticizing ai. surprise.
ai has so much potential, but no one knows what the future holds for the technology. this truth will excite …
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Waffle House—An American institution you can trust
The 21st century has seen America losing faith in institutions.
The government after September 11th, the medical establishment after COVID, universities and the mainstream media through it all—trust has eroded at every level of American society. Most …
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2x spicy ramen—An exploration of personal agency and trust
I’ll never understand how a ninety-nine cent pack of low-quality noodles became a gourmet experience in America. That’s the power of marketing, I guess.
Recently my wife and kids wanted to try this local ramen place. I was too lazy to make dinner …
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The profundity of personal post-punk philosophy
I’m no idiot, but I wouldn’t call myself a remarkably intelligent person either. If I’m being completely honest and letting go of any pressure to fake humility, then I have no problem saying I’m likely slightly above average intelligence.
But, Jake, I …
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How my kids inspire my art by managing upward
Some creatives worry that having kids will distract them from their art. But I’m lucky that, contrary to some expectations, my kids have actually inspired my art. And lately they’ve definitely pushed me to create far more than they’ve held me back.
As …
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Growth at all costs? The case for corporate efficiency
In business, growth is a hell of a drug.
21st-century American businesses must grow at all costs.
Grow headcount.
Grow the customer base.
Grow revenues.
If you don't grow, do you even business, bro?
Growth is all that matters.
Scale at all costs.
Sure, …
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Solution-made problems and cash from chaos
Not so long ago, getting a hold of someone was hard. You had to pick up the phone and hope they were in the office. You could send a letter, but it would take days to get there. UGH! No thanks. I need an answer NOW.
Then came email. Instant, easy …
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How sketching helps me get over perfectionism
I haven’t historically thought of myself as a visual artist. I’m a writer, not a sketcher or a painter. Or so I thought until a few months ago, when seeing my kids’ drawings inspired me to give the visual arts a try.
Now, as someone who’s added …
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What inefficiencies drive your business?
Efficiency isn’t always the goal. (Any consultant or private equity bros reading my blog just scoffed and clicked away to something else.)
Efficiency is worth pursuing, but we shouldn’t strive to be ruthlessly efficient in all things. Such emphasis is …
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Does quality belong in American efficiency?
In American business, efficiency typically emphasizes two points:
Quality is often an afterthought, if it’s a consideration at all.
So, I ask: Where does quality fit into the …
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The truth you know vs. the truth you feel
Why do insecure people believe things they know not to be true? Why do they listen to that nasty voice in their head telling them they’re not good enough?
These questions are just some I’m digging into as I’m on the fast track to middle age.
Recently I …
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Education's role in business communication dysfunction
Business communication is broken.
We send so much time talking and writing (emails, text messages, Slack and Teams, etc.) but we don’t really communicate; we don’t transfer information.
How do we solve this?
Through tech?
We’ve kind of tried that.
First, …
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Killing more trees faster
On this blog, I recently made the case for why writers should kill more trees.
That sentiment doesn’t apply only to writers. It applies to artists too. Drawers. Sketchers. Whoever.
Art can connect. Art can heal. Art can save.
So we need more of it. And …
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Sam Bankman-Fried and the imperfect calculus of effective altruism
I recently finished listening to the audiobook version of Number Go Up: Inside Crypto’s Wild Rise and Staggering Fall by Zeke Faux. The subtitle tells it all: The book is about the craziness that was the first crypto bubble. (As Bitcoin’s price …
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Will either presidential candidate challenge Big Tech?
If I were a single-issue voter in 2024, I’d vote solely on how I felt the presidential candidates would handle antitrust cases against Big Tech, not because I think tech antitrust is America’s greatest issue but because it’s one of the few issues we …
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Why we hate the tech industry even though we love tech
So many of us love tech yet have fallen out of love with the companies which comprise the tech industry.
But how can that be?
Data
We’re tired of tech companies exploiting our data.
‘If you’re not paying for the product, then you’re the product’ suggests …
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Is generative AI the best use of the world's electricity?
In a clip that starts a recent episode of the podcast Tech Won’t Save Us, Sam Altman acknowledges generative AI’s Achilles’ heel: energy. Generative AI needs a ton of energy, at a time when tech companies are supposedly pushing to curb carbon …
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Simplicity - The lost art we must discover
21st-century living is complicated. But must it be?
When you look around you, it’s easy to feel as if complexity is a requirement of the modern world. Most workplaces run via series after series of overcomplicated processes. To ‘exist’ today requires …
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Maybe businesses should kick it old school
Why is business so hard?
I mean, why do so many businesses struggle with basic tasks? Why do companies of smart and accomplished people seem to get bogged down on the way to success?
Here’s the simplest answer I can come up with: Employees have to wade …
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The thing about the cherry on top
What will be your life’s sweetest dessert?
I recently rewatched a video related to the prolific band The Cure being inducted into the Rock & Roll Hall of Fame.
No, it wasn’t a video of Trent Reznor’s flattering induction speech. It was the one of …
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The right fit vs. the qualified candidate
My son is in his final year of reg-league baseball. This fall season is his next-to-last season, with his last being in the spring. It’s a bittersweet time.
The bitter part of that equation is obvious—what if he never plays baseball again? What if …
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This revolution is small but it matters to me
How many layers must you wade through in the search for your own writing’s common thread?
I once said that persuasion was my own writing’s common thread, but now I’m realizing there’s more to it.
Humanity. The human condition. What does this mean for …
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Is community the blogging platform's secret weapon?
Not so long ago, bloggers used social media to share their posts and build audiences. While social media is unlikely to go away any time soon, people do seem to be falling out of love with it, if for no other reason than most of the mainstream social …
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Lessons from writing a novella I'll likely never release
I’m on the verge of finishing my absurdist comedy novella, which will become my longest completed writing project.
When it’s all said and done, I’ll most likely have enjoyed the process far more than the finished product. Because this pending novella …
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Don't become the Southwest Airlines of writing
In an attempt to reverse its falling stock price, Southwest Airlines announced it will start assigning seats to its passengers.
Congratulations, Southwest—you just became indistinguishable from every other airline!
Writers would be smart to question …
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Writers ain't gotta use AI if they don't wanna
If you’ve found a certain tool or service that works for you and makes your life better, COOL—then keep using that thing. This advice applies to AI, Notion, Obsidian, TikTok, WHATEVER. If your tool of choice is a net benefit, then keep on keepin’ on. …
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The business model dependency problem
No business stands on its own. Every business is dependent on something else in some way; the question is to what degree, and how stable is that dependency?
Transportation companies are dependent on highways and railroads and open waterways and skies. …
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Replacing human workers with AI is easy when we've already removed humanity from work
Since OpenAI released ChatGPT to the masses, there’s plenty of debate over where and when AI can replace human workers.
But I think this debate misses a crucial point. If AI can replace a human worker for a specific job function, why is that? Is it …
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Frugal reading - Tips for reading on a budget
So you wanna read more.
Maybe you’re trying to unplug more often. Or maybe you read a blog post about leadership and bought into the old adage that leaders read.
Whatever the case, you want to get your face in more books and digital content worth …
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Friends don't let friends become monopolists
In the autobiography The Life of Frederick Douglass, the author takes an interesting view on slavery when he argues that when otherwise good people become slaveowners, they can’t help becoming monsters. Douglass takes a compassionate view of the …
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MobiScribe Wave - The e-ink writing tablet I want to recommend but can't
I’ll always appreciate the MobiScribe Wave as being the device that proved an e-ink tablet has a place in my life, but after nearly five months of use, I’ve realized I can’t recommend the Wave to others. Or, perhaps more accurately, I can recommend …
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Managing expectations with a failure-first mindset
All too often, we contemplate how we want to succeed.
What would you do if you knew you were destined to succeed?
Go do that.
So the wisdom goes.
But sometimes it pays to look at the other end of the spectrum. What if your venture is doomed to fail? For …
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Creating in the time of AI
Why should we create in the age of AI? How can we compete?
This post from LMNT puts a different perspective on things:
I take a little comfort in knowing that it will be impossible for “AI” tools—here on out—to differentiate between human-made and …
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Is artificial general intelligence the real benchmark for AI?
Today’s target for artificial intelligence (AI) seems to be artificial general intelligence (AGI), a technology that is competent in many areas, like humans. AI is most often highly-specialized, focusing on one area with a narrow set of tasks. This …
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Will there be enough AI?
These days, people are worried about AI taking their jobs. And who can blame them, with all the stories circulating about AI’s great accomplishments. (P.S. If you’re looking for a counterweight to the hype, read Rebooting AI: Building Artificial …
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Digital Minimalism and philosophy in tech
I’ve been rethinking my relationship with technology since I started reading Digital Minimalism by Cal Newport.
After mentioning this book is usually when a blogger tells his audience he’s deleted his social media accounts and can now be reached only …
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The folly of predicting the future of AI and augmented intelligence
Advancements in AI and augmented intelligence are leading to endless predictions for the future. Nearly everyone has a hot take on what jobs these technologies will replace—or that it’s all a bubble waiting to burst.
So which is it?
Meh. Who knows. …
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AI vs augmented intelligence—A post about marketing semantics in the tech industry
Artificial intelligence (AI) has a marketing problem.
First of all, the term is everywhere. And everyone is using it. AI is sexy only to the laggards who recently accepted this internet thing isn’t going away and also started ‘hodling’ bitcoin1. The …
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Social media engagement algorithms and the illusion of choice
So many of us, over the last couple years, have been rethinking our relationship with social media and the internet at large.
My own wonderings about technology have seen me dabbling into using only open source operating systems and software. But I’ve …
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The Cult of We and the dangers of FOMO and hubris
If you had to sum up in only a few sentences the WeWork debacle to someone unfamiliar with the situation, how would you do so? The following quote from The Cult of We: WeWork, Adam Neumann, and the Great Startup Delusion by Eliot Brown and Maureen …
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Writing the puzzle
“It’s like putting together a puzzle.” That’s how my buddy explained oil and gas abstracting. “Does that sound like something you’d be interested in?”
Yeah, I told him. I’ll give it a shot. I still had no idea what “abstracting” and “chain of title” …