Leaving Before “Africa”

Who leaves a Toto show before hearing “Africa”?

Quite a few people, it turns out.

I saw The Romantics, Christopher Cross, and Toto at Pine Knob in Michigan—my first visit there in 25 years. Pine Knob is nicer than I remembered. There are waterfalls. Mature trees encircle the facility and sprout up inside it.

The Romantics and Cross sounded great. But Toto was phenomenal. Steve Lukather was incredible on guitar. Joseph Williams’ vocals still reverberate like it’s 1986. This was not a David Lee Roth situation in the slightest.

So why were people leaving before “Africa,” the night’s last song, was played?

Maybe society is so hyper-optimized now that efficiency trumps everything else. Maybe a perceived competitive advantage over a temporary peer group is more intoxicating than watching some of the most renowned musicians in American pop history perform their seminal art. This can hit even when that advantage is just a five-minute head-start on I-75. You know, the beer-soaked couple next to you won’t know you made it to Auburn Hills first.

The pressure to be efficient is so great that it squeezes the life out of making memories.

As Williams sang the lyric, “It’s gonna take a lot to drag me away from you,” I thought, “Yeah, no kidding.” I was watching people scurry out, missing exactly what they paid for.

I’m guilty of this too, but with smaller and more important beats. How many moments did I rush when my kids were small? In my work and friendships, how many meaningful conversations have I ended early to hurry to the Next Thing?

Leaving before “Africa” can cost you much more than the grand finale.

Memento Mori in the Family

People in families that struggle with drama and petty conflict seem to collectively ignore a big thing.

Everyone quibbling will be dead soon.

Doesn’t matter if you’re 20 or 80. In the grand scheme of time, you’ll be dead momentarily.

Through that lens, battling over trivialities looks absurd. Why burn energy judging and dunking on the people you are supposed to love, and who are supposed to love you the most?

We have few real allies in this world. We have fewer moments alive than we think. If we understand that time and connections are precious, it’s hard to imagine burning up both on small grievances.

Memento mori means, “Remember you must die.” That’s a weighty phrase. But the word “soon” needs to be included. Otherwise, death is just “someday.” It’s not someday. It’s near, for everyone alive.

Psalm 39:4 says:

Remind me that my days are numbered—how fleeting my life is.

When it’s over, we will leave energy behind in those who survive us. What will that look like? Best to choose wisely, in the brief moment we can.

The Container Has Its Own Energy

How do you pierce a dense creative fog?

I went months without writing much at all.

But in August, I published 19 posts to my website.

What changed?

The container.

When I rebuilt my personal website this summer, suddenly I had a bunch of ideas about the writing I wanted to put there.

And the ideas keep coming.

The container for your writing, where your writing lives, has an energy of its own.

At Write of Passage we inspired writers to build their own cathedrals of ideas1.
I don’t think of my site that elegantly. It’s more like a batting cage2, where I take a lot of swings.

If you’re struggling to write, more discipline or another Pomodoro app may not be your answer.

Maybe you need a new container with different energy. A new batting cage, where you’re excited to take your cuts and stack your ideas.

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Time to get to work on the tailgating playlist.

I don’t know if Michigan State will be good this year. I like the new coach, Pat Fitzgerald. I like the offensive line, the quarterback, and the running backs. Everything else, in this transfer-portal era of roster jambalaya, is a mystery for now.

The Spartans take the field Friday, Sept. 4, against Toledo, and we’ll start to discover how the new MSU recipe looks.

Last season, newly back in the state of Michigan, was about shaking off tailgating rust after 25 years away. It was a new start for the whole family. My daughter was a freshman at State. The rest of the family was starting over after decades in Florida. It was an all-new experience in a familiar place, a home state for my wife and me, and a place we had brought our kids many times.

A lot has changed at the tailgate.

There is still beer, but a lot less of it. I found a cigar is a nice way to top off the tailgate and transition to game time. And the food we’re eating now blows away what we used to eat, which was mostly whatever we could find.

And we’re going to need a new playlist.

A tailgating playlist must balance competing forces. Yes, you want lots of uptempo, but not only uptempo. A tailgate is a marathon, not a sprint. The music needs to reflect the way the day unfolds, from a cold morning start to the anticipation of packing up for kickoff.

And then there are differences in taste and preferred eras. For my wife, my friends, and me, it’s an easy Gen X setup: 70s, 80s, 90s rock. Some modern country and a few other modern songs blended in.

But the playlist’s job is bigger than just serving Gen X nostalgia.

When my daughter and her friends show up, the musical tastes tilt toward the present. Last season, between bites of a breakfast burrito, I noticed my daughter slyly tapping into Apple Music and adding her own songs to the queue: Harry Styles, Taylor Swift, and Noah Kahan.

I didn’t mind at all.

The tailgate playlist must both conjure up old memories and help cement new ones.

My tailgating playlist, in Michigan State style, has a few staples that have to appear.1

• ”Thunderstruck,” by AC/DC - The song the Spartans take the field to. I prefer the longer version from AC/DC Live.

• Bob Seger & The Silver Bullet Band - Michigan legend. ”Hollywood Nights,” ”Shakedown,” ”Against The Wind,” ”Night Moves,” and ”Mainstreet” are locks, most of which will come from the Nine Tonight live album.

• “Sundown,” by Gordon Lightfoot - An anthem, for reasons now lost to me, from the MSU-Michigan game in 1995. A light November snow falling, great friends, and a day that ended as the next one dawned. One of the most memorable days of my undergrad experience.

And yes, some stuff the kids like, too. Maybe someday, my daughter hear “Ophelia” and realize it’s emotionally fused to a fall day with her friends at MSU. She may not even remember why, but I’ll know she once snuck it onto the tailgate playlist.

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My writing is coalescing around an intersection of several topics and one durable habit. It reminds me, in structure, of the nightmare intersection at 4th Street in St. Petersburg I used to commute through daily.

(It may not look like much. But try skidding from Roosevelt onto Gandy at 5 p.m., on a Tuesday, in a Florida summer downpour.)

Fortunately, my writing intersection is more navigable than that hellscape of twisted concrete and swaying stoplights.

When I look at my past work, my present interests, and where I want my brain to go in the future, this is the intersection:

Use technology deliberately to build a rugged reading and writing habit.

Rugged, in that the habit endures in rapidly changing conditions. An active, intentional use of technology strengthens the habit. Passive use—scrolling, distraction—weakens it.

That clarity created momentum in my writing after a long dry spell:

• Rebuilding and relaunching my website.

• Reassembling and republishing past writing going back to 2004.

• Publishing several posts per week on my site and one or two Substack pieces.

• Choosing books over scrolling.

• Developing new workflows with the iPad as my reading and writing device.

My website sits in the middle of the intersection, directing traffic like one of those stoplights above a congested Gandy Boulevard. The Books and Writing pages reflect the inputs and outputs of the rugged habit. The iPad and Personal Websites pages detail how tech supports, organizes, and distributes the writing the habit generates.

Craig Mod built a personal website with a singular intersection: walking, Japan, photography, technology, and book publishing. So has Robin Sloan: technology, creative computing, fiction, stationery, and AI.

Their projects, opinions, and points of view don’t crowd each other out. Instead, through their connections, they create a distinct experience for readers. The person, the writer, sits at the center, tying it all together.

I want to help people read books and write, understand the cognitive and communicative value of those activities, and use tech to protect and strengthen those practices.

There is tension in that position.

Many who believe in the importance of reading and writing have a growing distrust—disdain, really—for technology. There is an undercurrent of hatred for AI1, and an idolatry of sorts for books in paper form2. In the other camp, some of the most fervent tech enthusiasts underestimate what passive technology consumption takes from us.

In Let Your Life Speak, Parker Palmer wrote about finding your vocation:

Before you tell your life what you intend to do with it, listen for what it intends to do with you.

Palmer might as well have been discussing the writing life.

I wasted energy and time forcing outside intentions onto my writing. But my own actions and interests had already formed a particular intersection. I just needed to let that come through.

That’s a little messy. It’s more interesting. And it’s very human.

Tips and Tools

Some other recent writing, and a small project:

• Apple Pages delivers a clean and simple writing experience on iPad. It’s my go-to writing app. Here are my favorite tips to help you use Pages for iPad smoothly.

• I am so annoyed with intrusive advertising on college football TV listings pages that I had AI build my own. Games are listed by week and kickoff time, and include TV and streaming listings. Feel free to bookmark the page and use it this season3, ad-free.

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I’m morphing 22 years of blog posts into an archive that’s easy for people and software to discover and navigate.

This week, Codex worked as plumber and archivist, fixing up some SEO plumbing and reorganizing 573 posts.

Serving readers is goal one. Good technical structure underneath supports discoverability for search engines and AI.

SEO

I used ChatGPT to write up a Modern SEO Review Brief for my site, which I edited. SEO is changing fast: traditional search still matters, but so does structuring content so AI systems can find, use, and cite it.

A simple and clear user experience matters most. I have no interest in keyword stuffing or bending post titles into confusing but SEO-friendly contortions.

This was a technical and structural review—not a content review—focused on a few high-leverage changes. I uploaded the brief to Codex, reviewed its recommendations, and had it implement some of them:

• Set a canonical domain.

• Establish permanent URL redirects to protect old links.

• Make the writing archive easier to crawl, including updated internal links, a site map, RSS feed, and page descriptions.

• Change how Kindle highlights are served because some AI retrieval sites couldn’t see them.

Finally, I added Google Analytics.

It would have taken a bajillion hours to do this manually.

And I couldn’t have done it on my own anyway. Codex discovered issues couldn’t, like the ambiguity of the “www” and non-www versions of my site both presenting as canonical. Same with the JavaScript issue blocking AI from seeing Kindle highlights.

AI is a useful SEO consultant. But I know the basics of SEO, and I’d be wary of taking this on without the background to judge the proposed changes.

The Archive

Following a successful archaeological dig to find another 90 of my old posts, I made changes to my blog history page:

• Changed the name from “Notes” to “Archive.”

• Set up a simple list of post titles, separated by month and year.

• Every new post now auto-updates to the archive page.

I’m fighting feature creep, but added a word counter.

The current tally: 372,818 words.

Kinda crazy.

The next step is to create topic pages that connect years of writing around a few favorite subjects like book reviews, Apple, writing, and a rapidly expanding area: building personal websites.

On to 400,000.

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But I definitely felt like an archaeological adventurer last week.

I recently used Codex to rebuild my personal website. As Codex was building, it pulled in old posts from my Squarespace archive from a file on my Mac, unprompted.

That got me thinking: where else could Codex look for my old posts?

After all, I’ve blogged off and on since at least 2004. There has to be old stuff out there scattered amongst the ruins of the Internet.

Turns out there was. A lot of it.

The Expedition

Finding two decades’ worth of old posts would be a tedious nightmare—I’d simply never do it. Let alone taking on all the formatting drudgery to get those posts onto my new site.

But Codex couldn’t wait to get started. And it had a plan:

Yes. I can search old author profiles, backlinks, archived blogrolls, redirects, domain-registration traces, and distinctive phrases from your known posts to uncover domains you no longer remember.

It immediately surfaced 11 pieces I wrote on Medium from 2014-2015. I have no recollection of posting on Medium. But I recognize the work. It also found two guest articles I wrote for Real Estate Magazine.

Then Codex informed me I had a blog on Blogspot. News to me.

Next, Codex unearthed an old site of mine called AskTheCopywriter.com. But how did Codex know it was mine?

Your own archived copy describes it as the place to visit for your marketing tips, copywriting insight, and “occasional drivel,” so this is strong first-party evidence that it was yours.

Um, ok. A little insulting, maybe, but accurate.

Then, Codex asked:

May I check Portugal’s public web archive for copies of the forgotten Blogspot and Ask the Copywriter sites that the Wayback Machine may not have preserved?

Suddenly I was nervous.

Portugal is keeping files on me. Why? What kind of files? I’ve never even visited Portugal. But Portugal, it turned out, contained riches:

This turned into the biggest find so far. The original Typepad hostname behind matttillotson.com now exposes archived post URLs that the earlier custom-domain sweep could not see … and appears to contain dozens of additional posts.

Codex continued:

May I retrieve the two archived FeedBurner feeds to recover any titles and dates absent from the page archives?

FeedBurner? Be still, my blogging heart. We had fun tech in those days.

The Recovery

In all, Codex found 81 posts that weren’t part of my new site, dating back to 2004:

• 46 posts from Typepad

• 18 from Posterous

• 6 from Askthecopywriter.com

• 9 from Medium

• 2 from RISMedia / Real Estate Magazine

With the artifacts uncovered, it was time to move them to the museum. Codex built backdated post pages in Obsidian for each entry, and shared this frustration with me:

The old Ask the Copywriter pages need a little extra character cleanup because they predate modern web encoding.

Yeah, thanks. I already knew I was blogging in the days of stone tablets. Didn’t really need the backhanded reminder.1

The Reward

Is there value to finding and collecting my old writing?

Sure. First, it’s fun to find this stuff. Especially the surprises.

I love having all my writing in one place, my place, online. More than 20 years’ worth of words!

The way I see my writing has changed. I think back and wish I’d been more consistent in the early blogging days. But man, I sure did try a lot of new things. That’s worth being proud of.

As Codex explored and formatted, a memory was sparked: I did some sports blogging at a site called Palmball.com in 2005. I asked Codex to search for any posts worth saving2.

In one entry, I wrote about Leigh Montville’s excellent biography of Ted Williams. In particular, I was envious of Williams’ singular focus in life:

And it wasn’t that Williams lived to play baseball. It was that he lived to hit a baseball. No matter what went on around him … Williams knew that the center of his existence on earth was to hit a baseball.

My inner critic considered my writing scattered, intermittent, and unfocused. It left me wondering what might have been if I’d had more clarity and consistency.

But this project showed me I was never meant to write about one thing. My writing is about exploring interests and finding ways to connect ideas across them.

One of AI’s best gifts for writers is helping us see our body of work in a new light.

I learned my writing is a little like Ted Williams after all.

I’ve taken a lot of swings. And I’m not done yet.

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I learned some HTML. I built in Microsoft FrontPage, and later used Blogspot, Typepad, Posterous, and Squarespace. You get the idea.

Things have changed fast. Now you can build and maintain the exact website you want, quickly and far cheaper than ever. Without technical knowledge.

Personal websites are back, and so is mine.1

Using Michael Dean’s post as a template, I wrote up goals for my site, loaded it all into Codex (OpenAI’s coding agent), and told it to create a site plan. I wanted a simple site (modeled somewhat after the timeless Daring Fireball) so I could focus on writing.

With that in place, I turned Codex loose.

The tech stack

Obsidian

The note-taking app Obsidian is home to all my content, as opposed to a complex content management system. Book reviews, my Kindle highlights, and new posts all live as simple Markdown files in Obsidian. No database needed—just text files on my Mac.

If you’ve never used Obsidian2 or worked with Markdown, don’t fret. Both are simple enough to get started with. And if you’re confused by either, ask AI. It will explain whatever you need to know.

Here’s what a post looks like in Markdown:

The properties at the top tell the website what to do with the post. There’s also a draft checkmark. When I remove the check and press the publish button, the note is uploaded to the next step.

GitHub

GitHub is where a complete history of the website is stored, and where automated sanity checks take place (reviewing metadata, links, images, and more to make sure everything works). Codex built the set of review rules. If all the lights for a new post turn green, then it is on to the next step. If something is off, Codex diagnoses the problem.

Cloudflare

Cloudflare hosts and serves the website from my custom domain. Because my site is small and simple, I pay Cloudflare nothing today. If tons of you visit, I might have to pay $5 a month, eventually. In contrast, Squarespace (which, to be fair, handles every step of site building and hosting) is around $400 a year now.

Think of the infrastructure like this:

• Codex: The contractor who built and maintains the site.

• Obsidian: The workshop where content is written and organized.

• GitHub: The storage and quality control facility where file versions are kept and inspected.

• Cloudflare: The storefront where the finished site is presented to visitors.

As a reminder:

I cannot code. I have a rudimentary understanding of what’s going on, but Codex built the infrastructure and process for me. I made decisions around site design and structure. Codex did the dirty work, and makes additional site changes at my discretion.

I have some knowledge of how websites should be organized, and what I wanted mine to look like. All I had to do was describe it.

Surprises

Codex had a few “ta-da” moments during the build.

First, I referenced my prior Squarespace website in my design brief. On its own, Codex found my downloaded Squarespace site content archive on my Mac3, and pulled in and formatted all my old posts in Obsidian, so they were part of my new site.4

Codex also found, without me asking, the 26,464 Kindle highlights I had stored in a CSV file from this project. It built unique pages for each book and attached all the Kindle highlights to each book’s page.

Codex also built custom buttons in Obsidian:

• Publish a note (blog post)

• Add a new book web page

• Add a one-off web page

• Download new Kindle highlights

• Tag a book in a note

I’m not writing commands or running between applications. I tap buttons. The infrastructure may be complex, but my workflow is not.

Site structure

• Start Here: A little about me, my work, and the website

• Notes: All my posts

• Books: A searchable list of over 450 books I’ve read in Kindle, with links to a book page for each. Each book page contains any posts I’ve written which reference the book, and the Kindle highlights for that book from my library.

• Newsletter: A signup page for my Substack.

Over time, I’ll add some additional sections, but will fight complexity. Site-fiddling is a great way to avoid writing, while telling yourself you’re being useful.5

AI has made bespoke, personal websites available to people who want to focus on creating, not coding. It handles the technical backend so we focus on our craft.

Bring on the personal website revolution.

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I believe the establishment is so named because seven is the minimum amount of ingredients and flavors you must add to your drink order1. Often, I have learned, a Seven Brew drink doesn’t even contain coffee. I think that’s because there isn’t room left in the cup after all the other stuff is added.

The most popular drink combos shift all the time, powered by TikTok trends.

A personal website that hosts your writing is the black coffee of the internet. Timeless. Useful. Never goes out of style, even as trends whirl and shift around it.

I didn’t always believe this.

In 2024, it seemed personal websites had run their course. Substack seemed a haven for writers. I went all in, shutting down my standalone site.

My blog-building began with Microsoft Front Page in the early aughts, before moving to Typepad2 and then Squarespace.

Here are a couple of posts from 20093, just to keep things honest:

Pulling the plug on my own website was a mistake.

I owe much to , who relaunched his own personal site, and wrote this post about how he did it. That nudged me to rebuild my own.4

The Free Traffic Engine Sputters

I don’t want to discourage anyone, but if you launch a personal site to build attention and visitor traffic, you’re facing Cat 5 headwinds.

One study suggests that as of early 2026, 68% of Google searches end without a click to a link, with users opting to read Google’s AI-generated content instead5.

The second challenge is AI chatbots. As more people turn to AI for answers, only 5.2% of information-seeking sessions result in a click.

Traffic to the open internet is drying up.6

Now that you are sufficiently disheartened, let me pivot: there are good reasons to have a personal website.

Why bother with a personal website in 2026?

My reasons will be different than yours. As it says in the top left column of my site:

A site to ingrain and invigorate the habits of reading and writing.

A couple of things are true for me:

1. When I exercise every day, I feel better and work better.

2. When I read from a book and write every day, I think more deeply and am more creative.

I’m on top of the first practice. The second had become inconsistent. My creative energy isn’t served by sporadic effort. It requires swinging the hammer daily.

And my site serves as the fulcrum for that daily rhythm. It’s a catalog of the books I read, the passages I highlight, and the writing that comes from that consistent reading habit.

One page lists most of the books I’ve read in Kindle since 2010—around 450 or so. All the book passages I’ve highlighted—more than 26,000 of them—have been sorted and imported onto a page for each book7. Any reviews or related entries I’ve written about a book also appear on that corresponding page. My new writing is shared and archived, blog style, on the front page. The site also has a bunch of my archived posts from my old Squarespace site.

It’s fun to integrate some of those Kindle highlights into my writing. Those 26,000 passages represent the words that stuck with or surprised me over 15 years of reading.

The site leans into my personal thinking trail and my perspective. The stuff that, you know, makes me a person and not software.

Anything I write now goes on my personal site first. That includes longer essays, like this one, and shorter notes. Some of that writing will also be shared and distributed here. But my site is the central repository for all my writing.

So, to sum it up. My personal website:

1. Serves as a living catalog of the books I read, the passages I highlight, and my own ideas and writing.8 It helps crystallize my own perspective.

2. Serves as an accountability engine to sustain my habits of reading and writing.

Could I just post everything to social media? Of course. But think of it like this:

There is value to sharing your writing on social sites. I’m not arguing you shouldn’t. But the amorphous social media landscape never holds still. Look how often the X algorithm changes.9 Facebook might become another TikTok. The energy is always on the move.

With your work anchored on your own site, you’re can follow that energy to other channels.

Social media is gambling on a football game. The value is here and gone. A personal website is investing in an index fund for 20 years. Value compounds.

An Antidote to AI Doomerism

We are subjected to an endless tsunami of negative content around AI: that it’s replacing our creativity, destroying our ability to concentrate, and obliterating our ability to express ourselves.

This project does the opposite. AI did all the coding and formatting dirty work so I can read and write. I feel the rust coming off, because I don’t have to worry about the technical machinery.

In 2026, a personal website isn’t primarily about amassing traffic. It’s about what you want to make, organize, and preserve that would otherwise be lost.

My site is the black coffee that jolts me into reading and writing every day. I’ll drink to that.

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I have a soft spot for iPads. Always have, since buying the original in April of 2010 for a quaint $499. I’ve always loved the portability and versatility. Can it replace my laptop? (For a long time, the answer was no. Now, the answer is yes, almost.1

My favorite iPad peripheral (that I bought again for the last time) is a divisive choice: the Smart Folio Keyboard. Apple discontinued the keyboard several years ago, replacing it with a bulkier, fancier, and of course more expensive, model: the Magic Keyboard for iPad.

People seem to love the new keyboard. But it bloats the iPad, wrapping it in the bulk and weight of a laptop.

The now-defunct Smart Folio Keyboard does not bloat the iPad. It complements the design, protects the device, and delivers a unique typing experience.

Many people hated the keyboard. Jason Snell, who writes about Apple and tech, compared the typing experience to “typing on a tent” because of its outer fabric shell.

But I love that keyboard, still.

And my old one wore out. That’s why I bought one, still new and in-box, to partner on a final adventure with my 12.9” 5th-generation iPad Pro. Thanks to a corner crack in the screen and AppleCare, my aging iPad was replaced last fall with a refurb: new battery, new casing, new life. My 2021 model now has plenty of miles to go, and a tentesque keyboard to ride along with it.

The keys strike with a Batman-like “Thwack!” It’s the sound of authority. The sound of justice. The sound of the Dark Knight landing a decisive right-cross to the Joker.

No other keyboard has the same sound and feel.

Of course, the 12.9-inch (or 13-inch as Apple refers to it now) iPad Pro is the wrong iPad for just about everyone, including me. It’s a little too large and heavy for true iPad convenience. It’s not a one-hander: you need to hold it firmly at 3 and 9 o’clock to keep it steady. It’s just a little too small to replace an adequate MacBook screen. And it balances like a drunk on a barstool when on your lap.

But I like it for kitchen table tasks — easy web browsing, or thwacking out an email or two — while my big MacBook stays upstairs. Also, the bigger screen can cover a second football game nicely, perched on the coffee table, while a main game plays on TV.

I also have an 11” iPad Pro. Because if you’re not sure what to do with one iPad, by all means get a second one.

The use cases are more clear on my 11-inch device. That’s where my daily habits of reading and writing get done. It’s my primary device for reading books, whether in bed, on a tabletop, or perched in front of my sweating face on the elliptical. It’s also the ideal size for an old comic book nerd2. And, paired with a standalone Apple Keyboard (not the foldable) it’s the perfect size for banging out rough drafts in daily writing sessions.

An eleven-inch screen is expansive enough for writing, but cramped enough to ward off the temptation to bring in a second app for distraction.

The limitation of the screen is not a bug. It’s a top feature.

Besides artists, I’m not sure anyone needs an iPad.

If you have a phone and laptop, you have everything covered. The iPad lurks in the hazy no-man’s-land between those two products. It’s pretty good for lots of tasks, and ideal for very few. But that hazy ground is a fun place to stumble around, tripping over new use cases and improvisations. You can reinvent your iPad, over and over.

My dad still rolls with the iPad he bought in 2013. Never upgraded. Never put in a new battery. Software updates dried up long ago. But it keeps doing what he wants it to do, so why upgrade?

What took me two iPads to figure out, he figured out with one, over a dozen years ago.

The iPad lets each user decide what it’s for. Everyone looks at the same slab of glass and sees a little different device. For me, the iPad supports a daily reading and writing habit. For you, it’s probably something else. The iPad has survived for 16 years not because Apple nailed exactly what it’s for, but because you make that choice.

Unlike me, you shouldn’t need two iPads to figure that out.

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“The End of Reading is Here,” trumpeted The Atlantic headline.

My immediate thought: “Good. I’m going to read more. And write more about reading more.”

But the headline missed both the true point of the article and the impact of the trend.

Reading isn’t dead. Instead, it’s retreating from the general population, and growing in concentration amongst ~20% of us, who are reading more:

Last year, print-book sales were higher than they were a decade ago. Barnes & Noble opened more than 60 new stores. Almost 400 independent bookstores sprang up in 2025.

Older Americans, college grads, and women are driving book sales today.

Some of us will continue to read (and write) a lot, and benefit greatly from it. Most people will enter a post-literary, video-and-audio only age. That doesn’t mean people won’t know how to read at all. They just won’t choose to read. And then reading comprehension, writing quality, the way we think and share information — that all gets worse.

Our literate society was, the theory goes, just a moment in time.

Not only will I read more, but I want to get more out of my reading. I want to share insights and sparks and weird idea connections with others who also want to keep their book brains switched on.

Part of that is better mining material I’ve already read.

For example, my Kindle library has 484 books in it today.1 I use the Kindle app on my iPhone, iPad, and Mac regularly. It’s a much better reading experience than a book.2 Easier to read in bed, or while eating, and it’s easier to highlight passages that surprise me.

But the Kindle app is locked down. It’s hard to get all those highlights (over 26,000 of them, in my case) into a searchable or useful format. You either need a physical Kindle device to download them, or a subscription to a service like Readwise.

Otherwise, you can view them book by book in the Kindle app or in a browser.

Until AI, that is.

I opened the ChatGPT app on my Mac, and wrote a prompt saying I wanted a searchable database of all my Kindle highlights.

Codex (ChatGPT’s coding agent) asked me to log into Amazon. Then it opened four browser windows, and divided my books into four groups. Simultaneously, it opened and copied highlights from all my books.

Manually, that process would’ve taken weeks, if I’d ever had the patience to finish.3

Codex knocked it out in about ten minutes, giving me a CSV file containing each highlight and the book and author it came from. For garnish, it also provided an SQLite database4 and a search tool.

Cool. Now, what can I do with it?

The real power isn’t in being able to just search for funny Dave Barry lines, or baseball anecdotes, or some specific text.

The real power is in asking AI to identify patterns and connections across the highlights, and to quickly find all the relevant passages on a given topic area.

There is a lot to use here both as creative fuel, and to learn more about my own interests and how they intersect.

Queries can be made to find patterns across all the highlights, for example:

• Which authors have I highlighted the most?

• What kinds of ideas seem to resonate with me over and over?

• Are there conflicting ideas I seem to return to?

• What kind of life do my highlights collectively point toward?

• What worldview emerges from these highlights?

• Write a profile of the person who would have selected these 26,000 passages.

• What subjects do I claim to care about that barely appear in my highlights?

• Find highlights that complement my June 2026 journal entries.

Or on a more granular basis:

• Find all my highlights around this idea: ____.

• Find the best highlight to answer this question: ____.

• I need a writing prompt. Find a surprising highlight I could build an essay around.

I love this.

It infuses individuality into my writing. These highlights represent what interested and surprised me going back to 2010, and that’s not replicable by AI.

Yes, AI can replace our reading. It can supplant our writing.

Or, we can use AI as a tool in our reading and writing to make it more useful, impactful, and poignant than ever.

I asked ChatGPT to find a Kindle Highlight to support the idea of AI as rocket fuel for the value of reading. It selected this, from Erik Larson’s The Demon of Unrest:

The search for these invariably becomes a journey full of unexpected surprises and revelations no matter how much a subject has been studied before—because every writer in every time brings to the field a unique lens through which to view the world, formed by his personal experiences and the character of his era.

AI doesn't have to pave over our unique lens. Instead, we can use AI to sharpen it.

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A grounded robin, an X detox, sprint science, Donald Fagen's 1982 warning, and a better question for midlife.

The Map

There’s a robin, Michigan’s state bird, hanging out at ground level in our backyard. By the deep coloring it seems to be male. Wings look ok. He’s not particularly afraid of us, though he did flap to the top of the shed when our dog, Lucy, paid a visit.

I can’t tell if his ground stop is by choice or circumstance. He hops around eating worms and getting water drops off garden leaves.

Robins are often the first sign of spring Michiganders seek. But not all robins are migratory. Some hang around all winter, congregating in wooded areas and eating berries instead of bugs and worms.

Maybe he stays at ground level because that’s where the eating is best.

1

The Machine

I’m addicted to X.

How can we hear own insights and ideas if we’re incessantly stuffing the ideas2 of others into our brains, one on top of the other, until any voice of our own is buried in an algorithmic avalanche?

Two nights ago, I started an experiment. No social apps, just a book when I went to bed3.

I read books on my iPhone and Mac4. That first night, the urge to stop and scroll X erupted, over and over. I felt disconnected from the world, from its energy, by not reading tweets. It was a powerful sense of loss. Almost mourning.

The next night was easier. And I didn’t feel the need to scroll much during the day, either. Maybe this habit is easier to break than it seems. Maybe I don’t have to spend a month rocking back and forth in a cold sweat. A small change can snowball, and I hope to hear myself again.

The Muscle

This week, I inserted a round of stationary bike sprints (4 rounds, 30-seconds all-out effort, 45 second recovery) in the middle of my 2-hour “zone two5” elliptical session.

Turns out there may be something to that:

In English, this means the study showed improved fat burning and vascular efficiency without lengthening muscle recovery time.

Of course, this study was with an even longer workout: 4 hours on a stationary bike, with three rounds of 3 x 30 second sprints, using elite-level trained athletes.

But we could expect some improved fat burning, even in a session like mine, which was less intense than used the one in the study.6

The Music

To my knowledge you cannot wear out a digital file. But my copy of this song may disprove that theory.

It’s “I.G.Y.”, by Donald Fagen, from the 1982 album The Nightfly. It’s pure Fagen — jazzy yacht rock, glimmering and celebratory on the surface, but all sarcasm and mockery underneath.

“I.G.Y” is a criticism of blind faith in progress and technology that fits 2026 almost too well.

The Middle

Midlife is a time for re-evaluation. Every time I read or hear a variation on “What are they gonna do? Reinvent themselves at [INSERT MIDDLE AGE HERE], I laugh a little and think, “They better.”

I had to do it at 48. Might be doing it again at 52. And I suspect there will be many more reinventions to come. I hope so.

In Depth Over Noise, writes about living a slower, deeper, more intentional life. In it, he shares a question that’s better for driving reinvention than asking, “What is my life’s purpose”:

When you ask “ What is the purpose of my life,“ you will look for an answer in the outside world.

[…]

When you ask yourself “How do I want to live my life,” it aligns you with your inner truth. It shows you your needs.

Social media shoves you toward the first question and feeds you infinite answers, none of which are genuine to you. And that obscures your ability to get real answers—your answers—to question two.

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The case for staying put, Siri's real edge, Rick Springfield at Planet Fitness, lifting before it's too late, and peak '80s album-cover testosterone.

The Map

Where are all the “stay put” missives?

So much Internet content celebrates being on the move: photographed restaurant meals and hidden-beach Reels. Or celebrating people moving to a new city.

Travel, in all its forms, is deified.1

Maybe it’s my season of life, but I don’t care about going anywhere. Back home after 25 years, I realize there’s more here than I could ever discover. And certainly a ton I never appreciated.

This is a wide-open content lane being ignored. Being grateful, learning, discovering, exploring, contributing right where you are.

Meanwhile, here’s the view from Ludington State Park’s Skyline Trail Loop, just 92 miles from where I’m tapping out this stay-put idea.

The Machine

Last week, Apple unveiled the new Siri AI at its Worldwide Developer Conference. Siri has been a crushing disappointment for years, and the last two were the worst, when announced AI features never shipped.

It seems that will change when iOS 27 rolls out in September.

The advantage Siri will have over ChatGPT and Claude? It’s not bleeding-edge intelligence. Other LLMs seem far ahead, for now.

Siri’s advantage will be twofold: convenience and context.

All those iPhones, Macs, and Apple Watches will have Siri available with a single tap. Zero-friction access.

Secondly, Siri will have (if you allow it) secure access to your messages, photos, emails, location — all the personal data on your phone.

That might make your skin crawl. If not, it can be very useful, as Joanna Stern shows in her Siri AI test drive:

The Muscle

I don’t understand Planet Fitness hate.

I’ve worked out there for almost a year now, after several years at Crunch locations. Yes, the heavy end of their free weights are lacking. But it has everything most people need.

That includes Rick Springfield.

In town on his tour with Sammy Hagar, Springfield showed up to work out at my local Planet Fitness this week. He was adorned in sunglasses and a T-shirt bearing his name, just in case there were any lingering doubts as to his identity.

Springfield is 76 years old.

"I work out every day,"

[..]

Basically, I watch what I eat, and I try and stay active."

He flies around the stage like Mick Jagger. If this is what Planet Fitness gets you at 76, I’m in.

The Music

Speaking of Springfield, dodged raindrops to see his show with Sammy Hagar this week. Hagar has a bit of an all-star band going these days: Van Halen bassist Michael Anthony, former John Mellencamp drummer Kenny Aronoff, and guitar legend Joe Satriani.2

Sammy’s vocal range is a bit diminished, but he’s as charismatic and energetic as ever. Someone said to me, “He’s just so cool.” So true. Some aging rockers aren’t so cool. You can feel them grasping for something that’s no longer there. Not Sammy. He’s just himself.

Very fun show.

And what album cover screams 1980s testosterone more than Hagar’s VOA, released in 1984?

I had it on cassette tape. Maybe you did, too.

The Middle

If you’re in life’s middle, right now is the time to build muscle and aerobic capacity.

Right. Now.

Don’t take it from me. Take it from a 63-year-old orthopedic surgeon:

Highly recommend this whole thread. Lots of wisdom on stress, relationships, and other items that will shape our later years.3

Oh. And I love this reminder, also. Don’t be so hard on yourself:

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Old-growth Michigan. The family IT rubric. An Uber driver's ancient MP3 player.
The wine-tracking CEO. Start pages, again.

The Map

Michigan was once thick with dense, old-growth forests. White pines, maples, beech, cedar, and many other trees dominated the state.

Then came the logging frenzy of the latter 1800s, when Michigan became America’s prime timber supplier. It was as bad as you imagine. Vast forests, clear cut. The book Wicked Bay City is loaded with sordid tales about lumber workers blowing their earnings and reputations along a stretch of town called Hell’s Half Mile. Quite a read. Quite an era.

But the logger barons didn’t hack through everything. Areas of old-growth remain, like Hartwick Pines State Park.1

(Here’s a list of Michigan’s old growth forests, should you want to visit.)

Michigan’s regrown wild areas are beautiful, no doubt. But the old-growth areas are different. Without a forest reboot, there’s less sameness to the trees’ size and age. That creates a different look, and more resistance to disease and harsh weather.

The variance is a strength.

The Machine

I’m the de facto IT director for a few households these days. I set up routers, root out Sonos speaker issues, and tame misbehaving printers, Macs, and iPhones. I try to get wifi signals to bathe even the most remote corners of a home.

Most of the time, the fix takes just a few minutes2. I find the work oddly and intensely satisfying. Bringing just a little more order to the universe. Making someone’s tech experience a little less turbulent.

A rubric that’s emerging for me: the best use of tech requires pruning. Not more. Not “optimization”. Pruning.

Fixing annoying issues. Using tech that supports habits, goals, and interests, and discarding the rest. If we’re mindful, we don’t need most of modern tech offers. Just the trimmed down subset that serves us.

The Music

I was sitting in the back of an Uber on a steamy Tampa afternoon. The driver was a friendly older guy. He had an ancient MP3 player, plugged in the car stereo, that fired off a random assortment of his favorite songs. Chicago followed The Supremes, who followed Ozzy.

I imagined he plugs that thing in every day and happily lets it serve up what it will, as he battles inside the Thunderdome tournament that is Tampa traffic.

I’m a playlist junkie, collecting and pruning songs by all kinds of categories. Genre: Yacht Rock, Country, Classic Rock. Time: 1980s, late 1990s, 1960s. A lot of curation.

My driver was having none of that. He inspired me to create a 400+ song playlist of my own. Essentially, every song I like from my own music collection, spanning decades and genres. Morgan Wallen and Motley Crue. Marvin Gaye and Mumford & Sons.

The variety creates surprise, even pulling from my own music files, the old and new and disparate intertwined, creating their own ecosystem.

The Muscle

There’s an odd fragility to the health and fitness dialogue on X. Especially amongst men who post on the topic. A recent clip made the rounds in which a younger CEO said three glasses of wine cost him three days of productivity.

Seriously?

Then, a study appears saying no amount of alcohol is safe:

But there’s pushback to the hyper-optimization health movement. We need to live, also. I’m not saying everyone should drink3. I am saying I’ll continue to drink.

What is the real goal of overly stringent health routines? it’s not immortality. It’s the act of chasing purity.

Yes, make mostly good choices. But also, live a little. We don’t last forever, no matter how rigorous a routine Bryan Johnson designs.

The Middle

If you are of a certain vintage, you remember the Internet start page. My Yahoo! was ubiquitous, but far from the only choice. MSN. AOL, of course. And you could build a Voyager Start Page, if you were a customer at the Michigan-based ISP I worked at, Voyager.net:

Man, that’s a nostalgia hit.4

Today, survivors still serve up start pages. Protopage delivers an old-school feel with an easy setup:

Yahoo!’s Scout works similarly.

The appeal of the start page in 2026? It’s a page you shape. That you prune. In contrast, on a social media site, an algorithm shapes the experience for you.

But I got to thinking: what could AI bring to a modern start page? Well, if you use ChatGPT or Claude regularly, it knows you a little bit. And it could render a page for you not just based on your preferred news and information sources, but on your intent. What you might want to see on a morning start page could be different than an evening edition.

In my case, I want news about Apple, AI, Michigan, and local sports and weather. But also: ways to synthesize topics into potential projects or newsletter essays. The AI-powered start page shouldn’t just scrape headlines. It should make useful connections between them and the things I want to get done.

Feels like a fun, straightforward project to tinker with. Kind of like we did at Voyager in 2000, but with a modern twist.

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Going viral on X, honing intuition, the real problem with Michigan weather, Ambrosia founder crushes it with Keith Urban, the true fitness wins.

The Map

The problem with Michigan weather isn’t the cold.

The problem is summer and fall are unbeatable and unreplicable.

You can move away to a warmer climate. I did.

But it’s not the same.

Not the same cool breeze. Not the same sound the wind makes moving through the trees. Not the same pine smell. The grass feels and smells different.

So you can leave, and miss all that. Or you can stay, and put up with the rest of it. The cold, the clouds, the mud and snow. And find something good in that, too.

I did.

The Machine

The post and photo above were shared on X, and became my most “viral” post of all time1. I’ve been on the platform since 2009, and that’s the first time I’ve had anything go over 1,000 likes.23

I don’t know if I learned anything, other than Michiganders—current residents and ex-pats alike—tend to be parochial, love Michigan, and like that content.

Also, no matter what you post, someone will be mad. 99% of the responses were conversational and positive. But there was also “You’re a glutton for punishment, worst climate in the northern hemisphere!!11!,” “LOL the South smells like pine too,” and various posts deriding the condition of state government.

There’s lots of hand-wringing about the explosion of AI-generated content. To me, a simple antidote seems to just be a real person who posts real stuff.

I am making the bet that real people can still connect with other real people online, weaving through the AI slop like Han Solo through an asteroid field.

The Music

Are we going to talk Yacht Rock in this space every week?4

As if that would be bad.

Keith Urban, country music star and sworn enemy of Nicole Kidman fans, is working on an album of Yacht Rock covers. Here is Ambrosia co-founder and former lead singer David Pack, 73, just crushing “How Much I Feel” on stage with Urban:

No rattle in those pipes. Just as smooth as 1978.

The Muscle

Fitness marketing is broken. The industry runs on promises of one-time, large-scale change: dropping large amounts of weight, or hulking out on a muscle-building binge.

Real fitness is quieter, incremental, and lasts decades. This tweet reminded me of that:

Big-time health changes are great. Don’t get me wrong. But the initial transformation is the first inning of a lifelong game won with incremental progress, just like Rachel’s.

The Middle

Intuition is invaluable, and so difficult to hear.

Entire sectors of the economy are designed to separate you from intuition, to pay attention to them instead of you. And even when you push back against that, you’ve got to dig through a layer of endless mind chatter to get to the heart of it all, that small feeling of knowing.

Intuition ain’t easy.

I can think of major life decisions that I made largely on intuition. But I want more intuition in small decisions that lead to bigger things, also.

This article is worth a read, and the X account is worth a follow if you want to hear your intuition, also:5

Can it be this simple?

I’d like to think so. I’ll ask my gut.

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Just need to flip the bedside lamps on, get my workout clothes ready for the morning, and call it a day.

But it seems Siri already went to sleep.

My requests to turn the lamps on go unheeded. I pull my iPhone out of my pocket. Open the Home app and tap the button to turn on the lights.

Nothing.

Just darkness. Sadness. Ineptitude.

Of course, I can just turn the lamp switch on. Except, no. I cannot. The “smart” bulbs override the switch.

I use the iPhone flashlight to find my tank top and shorts and fall into bed, wondering how smart homes can make life seem so dumb.

And yet, when the tech works, it can feel like magic. Like when the garage door yawns awake as you pull in the driveway. Or a warm and low light coming on when you step into the bathroom at night.

Good smart home technology removes friction. The house adjusts to you.

That “good” version—simple tech and automations that just work—2might be closer than many realize. AI will make products and automations easier to set up and use, and Apple, with new CEO John Ternus taking over in September, is poised to strengthen the Apple Home platform and products.

Google, Apple, and Amazon are all want to be your smart home platform. I’m placing my bet with Apple.

If you already have iPhones, Macs, and an Apple TV, you’ll find that Apple Home controls and alerts work very nicely with your existing devices. You have the control and communication hardware, and are comfortable using it.

Apple’s platform runs locally through an Apple TV or HomePod hub. That’s fewer trips to the cloud, one less point of failure, and a more secure and private experience, by design. And Apple Home is designed on the open communication standard Thread and the instruction layer Matter. That means setup and operations are simpler. Less fiddling, more “it just works.”3

Finally, once Apple ships something, they tend to support it for a long time. Google, not so much. Google is notorious for pulling the plug on services--even popular ones.

Of course, there are downsides to Apple Home. That commitment to privacy means additional hoops and expense for third party lights, locks, cameras, and other hardware to work with Apple Home, so there are fewer options. Apple is rarely first to innovate in any space, so Google and Amazon get the bleeding edge stuff first.

And Siri, well, Siri is way behind. But later this year, a new Siri is coming that will be powered by other leading AI platforms. This should help Home catch up.

I’ll take those tradeoffs.

Apple’s World Wide Developer Conference is next week, and we should see announcements about Apple Home and possibly some new products, like an updated HomePod Mini.4

I’m optimistic about the smart home’s future, and Apple will have the best mix of privacy and simplicity to help homeowners get comfortable with the space.

Pretty soon, we may not even need a flashlight to find our workout gear.

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Michigan's nuclear comeback, your iPhone's hidden toolbox, a Michael Jackson footnote, the cardio math nobody likes, and cereal as midlife metaphor.

The Map

Michigan may become the first state to bring a retired nuclear plant back online. The Palisades Nuclear Plant, located near the Lake Michigan shoreline in southwest Michigan, is being prepped to operate in 2026.

The global turn away from nuclear power was irrational. There is no more clean and consistent power source. And with Michigan hosting one of the most expensive, unreliable, and slow-to-repair power grids in the country, we could use the juice. I hope the facility comes online next year.

The Machine

Don’t sleep on your iPhone’s accessibility features. There’s plenty of useful customizations in there.

One example: I use the Back Tap feature (Settings → Accessibility → Touch → Back Tap) to reduce screen brightness.1 Three taps on the back and I reduce eyestrain and spousal annoyance when using my phone in the dark.2

Open Settings —> Accessibility, and poke around for things. It’s a hidden toolbox. Take advantage.

(I may do a whole column on Accessibility features at some point.)

The Music

Don’t start with Thriller.3

The Muscle

We need to sweat it out more. A lot more. Today’s exercise guidelines say to get 150 minutes of cardio a week. That’s not enough to make a material difference.

We need 8-9 hours a week for substantive cardiac protections to show up. The problem is that this seems like a ton, and it discourages people, who then do nothing.

Some exercise is better than nothing. Build from where you are.

The Middle

I’ve been eating too much cereal. It’s a crime to leave milk in the bowl, you know. Another round is always warranted. A little weight gain comes with that strategy.

That’s a leak.

Lots of midlife content is about total life reinvention. Practically, midlife change is often small and simple, with big results: fixing our leaks.

Energy leaks, like too much focus on news or scrolling. Food leaks, too much cereal.4

There are so many other leaks: time, needless daily frictions, mood killers, doomscrolling.

Small but important improvements come when we pay attention to where we leak5, and then tighten things up.

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Before I ever watched MTV, I listened to it on the radio.

MTV was once simulcast via stereo, because TV speakers were absolute garbage.

The simulcast was supposed to work only via direct cable connection to your stereo receiver. But if you lived in the right location and balanced the radio dial very carefully at 90.9 FM, you could pull in MTV audio over the air, wafting out from leaky cable infrastructure.

(How did we know this? I have no idea, other than the Word On The Street was uncannily valuable in the pre-internet days. Kids just knew things, like MTV broadcast frequencies and that E.T. Atari cartridges were buried in the desert.)

My grandparents, who lived just on the other side of my block, had a “cable box” before we did. That meant 36 glorious channels, not 12. World-changing.

Amongst those channels was MTV.

The height of video entertainment status, an all-powerful Jerrold Electronics unit, circa early 1980s

We didn't yet have that glorious box at my house when Michael Jackson’s “Thriller” video came out.

But I had a plan. A flight plan.

I would place my bike in driveway launch position2, and listen to MTV on a terrible clock radio that used radioactive materials to light the clock hands at night. The minute “Thriller” came on the radio, I planned to take flight, blasting off to my grandparent’s house to watch.

(I don’t think I cleared this plan with Mission Control3, either.)

I waited, I listened, and I heard lots of 80s music through a speaker with the acoustical characteristics of a Campbell’s Tomato Soup can.

But the timing for launch never worked out. That’s for the best. My Lawrence Welk-loving grandparents would have been mortified by the sight of me roaring into their home and commandeering their television, only to watch zombified Michael cavort around and crotch-grab.

After numerous aborted launch attempts, I eventually saw the video at my friend’s house. “Thriller” was worth the wait.

So is the movie Michael, which grants more access than even the cable box could, taking us through Michael’s youngest days in the Jackson 5 up to the 1988 tour for Bad.

There are so many milestone cultural moments this movie had to hit. And that’s why time sometimes moves faster in this film than in Marty McFly’s DeLorean.

The early Jackson 5 performances. The “Billie Jean” moonwalk at the Motown 25th anniversary celebration. The “Beat It” and “Thriller” videos. The disastrous Pepsi commercial. One after another, the film drops you right back in.4

One huge moment was absent: the making of the “We Are The World” video.

Sure, depicting all those stars would be a casting, licensing, and ego-management nightmare5. But it was a song Jackson co-wrote, and an assembly of stars that only his gravity well could have attracted. It would have been fun to see. That’s one miss, as was Janet’s total absence.

Michael isn’t all familiar and fun memories.

The film overuses the theme of Joe Jackson as a physically abusive father and domineering business manager. And yet, somehow, still underplays the impact. We get hints of the belt whippings. We see Joe push the boys, Michael especially, to exhaustion. But occasional belt whippings and a heavy business hand undersell what the Jackson kids reportedly endured.

Jafaar Jackson, Michael’s nephew and Jermaine’s son, is getting loads of well-earned publicity for his spot-on portrayal of adult Michael. He is Michael in this movie. And Juliano Krue Valdi radiates as the younger, Jackson 5-era Michael as well. Emotionally, physically, and musically, Valdi did a tremendous job. Talent, charisma, heart. That kid kills it.

A question: is Mike Myers federally obligated to play a boisterous record executive in every music biopic?6 Myers does a fine job here in spot duty as CBS Records president Walter Yetnikoff, much as he did as a record exec in Bohemian Rhapsody.7

The “Human Nature” concert scene, depicted during the 1985 Victory Tour with the Jacksons, is magnificent. It’s probably the movie’s strongest musical spectacle, taking us through the song in full. Jaafar’s dancing and likeness is incredible. The scene is similar to this performance, from the Bad tour in Wembley Stadium in 1988:

All these iconic moments, painstakingly recreated … well, that’s mainlined Gen X nostalgia crack.

And that’s why people love this movie. The music, the memories, brought back to life. Michael is idealized in this film, but that positioning gives the viewer an empathetic figure to root for as he completes his hero’s journey to creative freedom and independence.

I think that’s why critics savaged this movie: it wasn’t honest and gritty enough. But gritty was never the goal.

It was strange watching this film, being back now in my hometown, where I first experienced many of these moments. There I was, at the same geographic coordinates I populated in the 1980s, and yet, I live in a completely different universe now than the one onscreen.

That juxtaposition of place and time wove a feeling of melancholy through the fun and nostalgia. The 1980s were a cool time. An era long gone. As the talented Northern Michigan writer often tweets, “The world you grew up in no longer exists.”

Still, it was good to be there in the 80s. And good to be back, just for a little while.

Subscribe now for more photos of 40-year-old cable TV technology.

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It can be a formidable foe.

The Promise and The Pain

iTunes Match launched in 2011 as a bridge between “I have MP3s smattered across my hard drive1” and seamless, cloud-based music streaming. It's supposed to scan your files, find matches in Apple's cloud library, and stream those copies instead of yours.

For $25 a year, Apple gave you a clean library of your files you could stream anywhere, without having to worry about what was or wasn’t downloaded.

Today, you can still pay that $25 a year, or pay for an Apple Music subscription and get the same matching service for your own music files.

However.

iTunes Match doesn’t always get it right. Sometimes it’s like the drunk guy at a corporate function who calls you Bob2 even though you’re wearing a name tag.

So you’ll find, sometimes, when adding your own ripped files to Apple Music, that iTunes Match uses the wrong album artwork, splits up an album in two,3 just plain refuses to upload a track, and other joys that will mess up your library.

Let’s run through a couple of common issues.

Album Splitting

If we’re talking about splitting up, then it only makes sense to use a Beatle as the example4. This compilation from Paul McCartney, called Pure McCartney, was ravaged by iTunes Match, splitting it five ways.5

Two moves will solve most album splitting issues.

First, go the Apple Music album view on your Mac. Click through to the first instance of the album get the list of songs. Hit Command + A to highlight all the tracks. Then right click (or hit Command +I) and select Get Info.

Now you’re into the track data, and can commence your role as the Song Sanitation Department.

The two moves that often solve all:

1. Make sure “album artist” is the same for every track. In this case, that meant overwriting “Paul McCartney & Wings” “Paul McCartney & Michael Jackson,” etc. with simply “Paul McCartney.” You can also use “Various Artists” here if you like, but that will move the album out of the artist’s category and into a Various Artists bucket. That categorization is best left to compilations, like movie soundtracks or the Forever 80s compilation which was endlessly pitched on TV in the 90s that I picked up for $2 last year6.

2. Speaking of compilations, that’s your fallback if unifying “Album Artist” doesn’t do the trick. It’s a checkbox. Click it, and iTunes Match says, “Ooooh, there’s a bunch of different artists on the same album. Cool, let me bunch them back together.” Except when it doesn’t, of course.

If that still doesn’t work, you can always try deleting and reuploading the album. And sometimes, well, sometimes no matter what you try technically or which patron saint you pray to, Bon Jovi’s Greatest Hits will simply not unify.

No matter what I tried, “Blaze of Glory” would not join its Bon Jovi brethren on the same album. When I scroll on my Mac, the folly is always there.

Except it did unify on my iPhone.

iTunes Match, ladies and gentlemen!

The Graying

I ran into this problem frequently. I’d rip a CD and upload it. All looked well, until I went to play a certain song through my iPhone instead of my Mac.

Here you see some songs from Eliminator, eliminated by iTunes Match.

Well, my Classic Rock Mix playlist was not going to fly without “Got Me Under Pressure” and “Sharp Dressed Man7”.

It’s fixable.

When The Graying happens to you, and it will, your best bet is to delete the grayed out tracks from your library and re-upload. Other times, the whole album needs to be reset.

Annoying, a little time-consuming if you have a decent-sized library, but not terribly difficult.

Certain tracks have reputations for going gray8, like “Computer Blue” from Prince and The Revolution’s Purple Rain album. Apparently that track appears on a number of different albums and causes iTunes Match to fritz out about its placement.

The only option that worked was to add an underscore to the track title by altering its name inside Apple Music. At that point, Apple Music says “OK, I don’t know what this is, I can’t match it, I’ll just leave it alone.”

So my copy of “Computer Blue” is titled “Computer Blue_”, and sits in its rightful slot, track #4, on Purple Rain.

Other Normie Issues

Those are the most common technical issues most civilians will encounter when uploading their collections.

Other annoyances, like stuck tracks that won’t upload, can often be remedied by going to File > Update Cloud Library to force the upload. Failing that, deleting and re-uploading9 often solves the problem.

But outside the normal civilian existence lurks a population that’s deeply into tagging their music. You can tag at the album or track level in lots of creative ways: era, genre, songs that remind you of sophomore year of college. It’s up to you, and can be a big part of curating your collection.

Most people don't mess with tags. But some people really mess with them.

And iTunes Match can really mess with those people. Horror stories abound of hours and hours of tagging work being nuked by Apple Music.

We won’t get into tagging inside Apple Music today. We might another day, if I venture down that rabbit hole myself.

And we may get into tidying up Listening History at some point.

For now, I have a mostly clean and crisp library of my own files.10 And if you upload your library and have the patience for some simple cleanup afterwards, you will, too.

If you get stuck, I’d be interested to hear about what’s going on in the comments. Let’s see if we can fix it. As long as it’s not “Computer Blue_”.

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It didn’t work out.

And as it turned out, the right solution was sitting there all along: Apple Music.

My Apple Music library was a Frankensteined mess of my own music files (uploaded from CD rips and iTunes purchases) and streaming songs from Apple Music I’d “added to library” over a decade using the service.

Unseemly. Unowned. Unrecoverable.

So I deleted the entire Apple Music library and started over, ripping one CD at a time.

Back to square one1.

The Great Erasing

Deleting your library isn’t hard. On your Mac, go to the songs view in Apple Music. Press Control + A to select all. Right click. Select delete from library.

Poof, done.

Clean slate. Unfortunately, a little too clean.

Mistake #1: Not backing up my data and playlists first

I’m a playlist builder2, with around 30 created over a decade. Some had close to 1,000 songs.

When I deleted my music library, guess what else went away? The playlist content.

Not the playlist shells, though. Oh no. They stayed right there. Signposts to nowhere. Barren, persistent declarations of my haste.

A Yacht Rock playlist with no vessels.

The loss included the Valentine’s playlist I painstakingly assembled for my wife, and wrote an entire post about.

Whoops.

What to do instead: before resetting your library, download Hezel. It backs up your Apple Music library tracks and playlist data, for free.

It takes like five seconds to back up your data. I didn’t.

The rebuild

With files and playlists obliterated, the slow rebuild began. That meant feeding CDs into an external drive, one by one, and using the XLD application for Mac to rip and organize the files.

You can rip right to Apple Music. But I wanted a backup folder first, which I’d then transfer to Apple Music.

I ripped all my CDs in lossless FLAC format, a widely used open standard for music files that is uncompressed, meaning that all the sound data is preserved. Because you’re getting complete data, an individual song can be pretty big in this format, anywhere from 30-50MB or more.3

So, lots of storage space needed, but all good. I had pristine, lossless files to upload to Apple Music.

Except I didn’t.

Mistake #2: File format

Apple Music doesn’t work with FLAC files, open standards be damned.

For lossless audio, Apple Music uses the company’s proprietary lossless format, called Apple Lossless Audio Codec (ALAC).

It takes a long time to rip a decent sized CD collection, slowly feeding disc after disc into the gaping maw of the external drive. I had no interest in starting again.

Claude came to the rescue.

Claude spun up a Python script that I copied and pasted into Terminal in my Mac. It converted all the FLAC files to ALAC. It took a few hours in the background. No sweat.

But lesson learned: for Apple Music, rip your files to ALAC format.4

The Collector’s Library Structure

So I was ready to hand over my files to Apple Music, but not without a strategy for the library going forward.

My library in Apple Music is only for files I own. I don’t click “Add to library” for any track or album that streams from Apple Music. I listen to songs that I don’t own, but never add them to library.

The library is mine. That’s what I mostly listen to. I use Apple Music streaming over the top to fill in some gaps, and for new music discovery through Apple playlists (like Today’s Country) and Apple’s radio stations.

But streaming never gets inside my library. That’s a watertight safe with only my own stuff.

Why do this? Don’t you have a life or something?

Indeed, this is a lot of uploading, curating, and cleanup headaches that are, in this streaming era, entirely unnecessary.

Unless you still want to own your music. To listen and buy with intention, without being mindlessly tossed about in a raging algorithmic river.

After all, what is a music “collection” anyway?

Inside Apple Music, it’s just a collection of data files. If you have CDs on your shelf, that’s just an inefficient storage system. If you’re into vinyl, well, that’s even less efficient.

But a music collection is something more.

It’s a curated archive of memories, audio that delivers a range of emotions and moments from your life, past and present.

A music collection is more than algorithms. To me, anyway.

Next up: Screaming Match

iTunes Match can be massive thorn in the side of music collectors.

It’s an Apple Music service that recognizes5 music you upload. It says, “Hey! I know this song, artist, and album! I have a perfectly good copy right here in the cloud so we’ll use that version for you to stream.”

But iTunes Match gets things wrong. It splits up albums. Seemingly at random, it grays out songs that you then can’t play on your iPhone because … reasons.

You can tame iTunes Match. We’ll get into that next time.

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I’m back working with and 1, who founded Circle Studios, a boutique agency that builds live cohort learning experiences for leading creators and media businesses. Circle Studios is a division of Circle — the company that built the software that hosts over 19,000 online communities2.

If you were part of Write of Passage as a student or Crew member you already know how rewarding this work can be. I loved it as a student, as a mentor, and eventually as Director of Student Success and live session co-pilot. I grew more professionally in those 3+ years than in eleven at my previous job. We did great work together, with a team of dedicated people who brought it to life for students.

Now we're doing that again. And maybe you would like to join us.

I’m building a community of learning professionals: instructors, session co-pilots, producers, and mentors who want to help eager, bright students change their lives and careers.

Sound interesting?

You can learn more and apply right here, right now.

Our most pressing need: an instructor who lives and breathes Claude, teaching a live cohort for one of the top AI entrepreneurs and creators on the internet.3

Much more to come from Circle Studios. I hope you might come along for the ride.

Mine just beeped a lot.

The practice of intentional listening, of (re)building your own music library, sounds fun and self-deterministic. But when you find yourself returning hard drives and rebuilding song libraries again and again, it’s time to see another strategy.

I believe we should own our music and not drift into the Spotify dream of music as barely-noticable background noise.

One way to do this is to rebuild (or blow the dust off of) your CD collection, rip those CDs to digital copies, and store them on a home network-accessable storage system. A NAS, built, curated, and collated by you.

A simple, self-contained music system … right? Right?

The NASty truth

I purchased a home server from Synology and two 4TB Western Digital hard drives. Thanks to AI draining the world of computer memory, it took weeks for the drives to arrive.

With two drives installed in the server, you can create a mirrored situation that gives you an instant backup for all the files you’re storing. If one drive goes down, no worries. The other has all the same files. You can remove the bad drive and swap in a new one. Seamless. Safe. Foolproof.

Yeah, right.

Although seemingly delivered by Wells Fargo wagon, the first drive finally arrived. With Claude’s help, I configured the Synology system and had it running pretty easily. Then began the process of transferring thousands of large music files (FLAC format—lossless and uncompressed) onto the hard drive from my Mac. Claude wrote a script for me to use in Terminal that automated a process that took hours.

With the files transferred, I used Plex software on the server and Plexamp on my iPhone.

Plex, for someone with their own music collection, is pretty great. The UI is beautiful. There are lots of capabilities for intentional listeners who want deep stats about their listening habits and library.1

It was slick. It worked well. The files were mine, on my own system, accessible from anywhere with wifi.

For awhile, anyway.

Further down the space-time continuum, the second drive eventually arrived. I installed in on the server.

Dead on arrival. Apparently, this is a fairly common occurrence for hard drives shipped through the mail2. They can have a delicate constitution.

No worries. I returned it and awaited the replacement.

Then, after less than three weeks of operation, the server started beeping in protest one cold Thursday morning, sounding angrier than R2-D2 in the swamps of Dagobah.

The initial drive had died, too.

So, disappointed and music-less, I awaited the arrival of both replacement drives. I set them up as new. I started the process (again!) of transferring thousands of music files.

More beeps. Something went sideways in the mirroring process. The drives were not broken, but the setup process had to be restarted from scratch.

Cool, cool.

I reset everything from the beginning. I began the file transfer process again.

After several hours, I noticed the file transfer was no longer running. No beeps of protest. The transfer script just chose quiet quitting.

And that’s when I quit, also.

I just wanted to listen to my music

I like to tinker. I liked setting up the hardware and playing around with the Plex software. I did not like being an IT firefighter, battling beeps and bad drives and lazy scripts. I just wanted to listen to my music.

I unplugged the server. I pulled the hard drives. I sent it all back.

And moved on to Plan B.

In 2026, there are simpler ways to both own your music and get to the process of enjoying it.

We’ll cover that in the next post.3

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