I did something I didn't expect I'd ever do this year: I asked an AI for advice. Asking it for recommended places to visit on a trip is one thing, but this time I wanted to get some stuff off my chest, turned on voice mode, and just ranted for a bit. I'd avoided the idea for a while, with a nagging concern that outsourcing our thinking to AI is concerning enough, outsourcing emotional support is a step too far, and yet.
Surprise surprise, it worked out well. I still wouldn't recommend using AI as a therapist, with the dangers of it reinforcing negative thinking (with similar dangers to almost any online pursuit of advice, where a slightly negative YouTube query can send you spiraling into every more dark content). In my case, though, it mostly recommended hearing everyone out and making sure they knew they were heard even if everyone didn't agree, and so on. Nothing at all groundbreaking, but the simple process of talking out what was weighing on me itself felt good.
The month prior to that incident I'd spent my time testing journaling apps for Wirecutter. There were apps that were little more than digitized versions of paper journals. Do-it-all apps that essentially let you build a digital scrapbook documenting your lived experience. And, as is the case for every software category in 2025, AI-powered journaling apps promising to help you dig more into your thoughts.
Typically they'd start with a question about your day, either a prompt from a library or a generic question to get you to start typing. Then you'll ask for a followup, and the AI will digest what you wrote and ask a question about how that made your feel or what you'll do next or some other question that will guide you to keep typing. And ... it worked. It felt good. Not, again, that any specific insights came out of the extended prompts, but it made me think more about what had happened and approach my day more thoughtfully.
Zoom out, and it's the same as the classic improv idea of building on what another had said with "Yes, and," something that doesn't require an app, let alone AI. Yet the AI-powered journaling apps did fill an interesting spot in helping one be more mindful about their day and log more detailed journal entries that help you remember the day better just by having written it down.
The Tl;dr is that Day One packs an impressive amount of features into a journaling app, Apple Journal is a great free option, and Rosebud was my favorite implementation of journaling with AI. But that's the overview—go read the full piece for more details on which journaling app you should use to start logging your new year.
Credits down. Lights up. I can’t believe... and The impact... and That cliffhanger! and How could they keep us in suspense and No, what that meant was.. and Masterpiece and Worst film of the year. Chatter, human static.
You stand up and stretch, feel for your phone and wallet to ensure everything’s right with the world. Shuffle out of the theatre, popcorn crunching underfoot, past overflowing waste bins, out of the groggy warmth of the theatre into the blinding lights of the foyer.
Ping. Heavy rain in 3 minutes, the text fades in from the top right of your peripheral vision. Good thing. Not like you could have guessed the weather from the 7th floor. You’d scarcely know the time if it, too, wasn’t a glance away. Might as well grab a bite to eat while waiting for the storm to dissipate.
You drift with the flow, down an escalator, around a corridor, towards the xiaolongbao shop on the 6th floor, or 5th—you can vaguely picture it, and your sense of indoors direction is good enough to locate it, surely.
Hey just checking in on the copy for Thursday’s launch, pings a chat notification. Got a few minutes to chat about it?Had some last-minute ideas to add.
Deep sigh. If only theatre mode could be kept on forever. That rare escape into another world, free of distract... Actually, I’ll just jump in and make the changes directly if that’s find with you. Damnit. This client will be the death of you.
And the vaguely spacelessness and timelessness of the mall aren’t helping. The corridors turn into other corridors, the branded restaurants blur one into another. Everything on offer, anything for sale. Choice itself becomes burdensome.
Hey Alfred, where is the xiaolongbao shop? I should have a photo of it, somewhere, from the last time I was here.
Found it, replies the gadget. It’s on the 4th floor. Head downstairs, it says, and you comply, mind disengaged to autopilot, feet falling one after another without a conscious thought.
Turn left, and you turn. Ok, on your right. You’ve arrived. Enjoy your meal—and hey, don’t forget there’s a 50% special on the char siu bao today.
What would you do without your gadget, you think. Can’t live without it, even if you can scarcely live with the notifications. The benefits still outweigh.
Except, wait. Weird. You’re in front of a restaurant, all right, even one that sells bao. But this isn’t the xiaolongbao shop. You’ve never seen the place before; it wasn’t in your memories. And there, for definitive proof, underneath the faux-neon signage, hangs Grand Opening. Bouquets surround the checkout counter. The proprietor looks around—and you know they’re the owner, with their business casual attire, slight smile while surveying the crowds, the Thank you and come again and So glad you stopped by and Don’t forget to like us on The Network foreclosing any doubt.
But hey. A new place could be fun. Who needs xiaolongbao; here’s to adventure!
Hi, how many people are in your party? Just one? Ok, right this way. Shuffle past the crowds to the solitary stool at the bar. Might as well try the char siu bao; it’s on sale, after all. And this, and that, and soon you’re sipping hot oolong tea. You would have loved the film, you nearly whisper to Alfred. Wish you could have made it! Then the bao arrive, the bok choy, the soup, and in the hazy warmth your mind drifts back to the film. How could they have lived in such a time? How could one sit idly by?
If only... Ok, I decided to cut the entire “Why we built this” section. Too much. We built it, no need to explain. Everyone’s going to love it anyhow. And the fog lifts. You’re back in the restaurant, your tea’s gone cold. Time restarts. Whatever, Mr. client. You couldn’t care less, you tell yourself, yet you do, and now there’s a bug in your mind you’ll have to squash. They’d said, just yesterday, that you needed to add that section. Said it was crucially important, enough for you to burn the midnight oil in pursuit of a more perfect launch document. That, that was why you treated yourself to this half-day-off anyhow. And now it’s just another bit of cut copy—cut copy they asked for. And you could, right here, right now, pull up the doc in your field of vision, check their edits and fight for that precious bit of script’s life. Your darling, mercilessly cut and left on the editing floor. Who does that?
But no. It’s your—wait, what day is it? Thursday. It’s your Thursday evening. You wouldn’t be working for yourself if you didn’t want the occasional movie-and-dinner on a normal afternoon. You stop yourself. Breath. Focus. A long glance around to ground you. Edits can wait for ... Out of the doc. Damnit. Ready for launch 🚀.
It’s almost enough to want to walk back in the theatre for another 3 hours of well-earned silent mode.
Sigh. At least the food was good. Finish off the tea. Bite of roasted pork, the piece you were saving for last. Never as good as it was when it was hot, fresh, never as good as that first explosion of flavor when you bite into something for the first time. A photograph, a memory for your tastebuds, a parting gift of sorts, unsatisfying yet gratifying all the same.
Walk towards the entrance, a bit more haltingly than when you came in. You’re sated, 28 minutes and a year older all at once, it seems. Proprietor’s tending the register. How was your meal? Here’s your check. Long-stare into the screen, double-blink. Payment approved fades in. You turn. Exit to the left.
Scratch. The bao were half-off, right? You step back in, ask for the receipt you’d just refused, and nope, everything’s full-priced. Wasn’t there a... you start, then stop. It’s a new shop, they’ve likely dealt with a dozen mistaken bills already today. Whatever. You’ll live. Never mind, thank you! Yes, you’d be glad to leave a review.
It’s just not your day. How’s the weather now, Alfred? Scattered showers. Of course. Just your luck.
Hey Alfred, call a ride home. Sure thing, checking availability. Ok. Found a black Model Nee three minutes away. Meet them at Exit 3 on the ground floor.
Down the escalators. Around and around. You had asked me to remind you that you needed to pick up socks the next time you were out shopping, pipes in Alfred. Not now, Alfred. Next time. Time to face the rain.
Head towards the exit, but no, that’s exit one. Your ride has arrived, says Alfred. There’s a 10% discount if you head to the information desk to validate your receipts. No time for that, Alfred. Where’s the right exit? you reply. Up, down, left, right, and finally a 3 appears over the doorway in the distance.
You step out into the sunlight. Huh, it’s not as late as you thought. You blink, readjust, pupils constricting to restrict photon access. What’s the car’s license plate number, Alfred? TU2156, it replies, and a faint license plate hangs in your peripheral vision. Off to the right, behind two yellow cabs, waits a grey car, plates TU2156. That’s the car. Could’ve sworn it was supposed to be black. Whatever. Close enough.
Climb in. Buckle clasped. Lean back. Leg involuntarily moving to the vaguely familiar beats. Look up at the azure expanse. No haze, for a change. A bird flies by, solitary. The vehicle accelerates away, finds its place in the traffic, navigates towards your destination on dry, dusty lanes.
Jumping out for the day, pings your chat. Dropped in a new intro. But you can’t even muster the energy to be annoyed. It’s too nice out to stew.
If you’d known it was this nice a day, you’d have walked, saved the fare, closed your movement goal, made the most of your evening off.
Wait.
Where was the rain?
a story, by Matthew Guay. Originally written April 28, 2024.
Ice cream parlors made me freeze up, as a kid. Not from the freezers, or the brain freeze after wolfing down a scoop. Indecision, instead, left me holding up the line.
I’d step up to the counter, puzzle over the dozens of choices at the local ice cream parlor (the—sadly—long-defunct Kay’s of Knoxville), and settle for something reliable and familiar in the face of so many options. Over time, I settled on a rubric: I choose limited edition flavors or whatever I’ve never tried before, favoring novelty over familiarity.
Making choices between a wide range of equally appealing options can bring the best minds to a halt. You know, deep down, that you’re leaning in one direction. Yet what about this? What about that? You’re afraid of making the wrong choice, scared the right choice is not the absolute best. So you halter, waver, go back and change your mind, frozen by analysis paralysis.
Yet there’s a simple trick to overcome it: Reduce the options.
It’s hard to choose between 31 flavors. Far easier to choose between chocolate, vanilla, and salted caramel. That applies when you’re choosing items alone, or in a group; it’s almost possible to get a group of friends to decide between 10 restaurant options, but if you remove every option that anyone dislikes and have 3 non-objectionable top choices, it’s both easier to pick one option and safer since anything that gets chosen is unlike to be anyone’s least-favorite restaurant.
It’s not like you want no choices. It’d be a boring ice cream parlor that served only vanilla, and when a friend suggests a new restaurant, there’s always the chance you’ll discover a new favorite. You want just enough choices, not so many as to be overwhelming, but at least enough to require your input.
And so we built an app: Woolean. It’s the app to help you decide things.
The idea, for my co-founder Ryan, started with choosing lunch options. For me, the idea solidified with design and wording choices. For years, I’ve shipped articles to editors with multiple title and subtitle options (along, sometimes, with multiple header image options as well). I’d write my three favorites, they’d then comment on a favorite one or two, and we’d go from there. It’s like A/B testing ad copy, led by the content team’s personal preferences.
Then the same thing came up, when I worked with a design firm on Reproof’s branding. Our designers sent us three color palettes and four logo options—each were great, but we needed to choose the best. And so we’d remove our least favorite options, one at a time, until we settled on something we loved.
Again and again, I’ve found making choices to be easier when I can first winnow the options down, then choose from two of the best things. It goes for font choices, for photos, for vacation hotel choices, even for flights where you’re trading off getting to the airport at an ungodly hour for a direct flight.
Woolean is built for that and more. You can add a list of anything: Plain text items, dates, colors in hex value (including entire color palettes), links (complete with a preview), images, and audio. You can type out the list, or upload it as a spreadsheet. You can add a title if you’d like (to ask people to choose their favorite logo style without worrying about the colors, yet, perhaps).
Woolean will split any list up into one-on-one, pairwise comparisons of two options. Do you like the item on the left or right better? Click to vote—or use your right and left arrow keys to fly through comparisons. This versus that, over and over, until you work your way through the list.
As you’re voting, you’ll start to see your personal preferences taking shape. You might choose vanilla over strawberry, but would choose chocolate over vanilla, and salted caramel over chocolate and strawberry and oh turns out salted caramel is my favorite.
Share the link, and you’ll see the same realization unfold from your friends and colleagues’ choices. You might not find a unanimous favorite food for your next outing, but you’ll definitely find out that one thing that no one chose and can ensure you don’t pick everyone’s least favorite food.
Woolean is just for fun—and we’d love to hear how you use it. We’ve used it to make all types of decisions over the past few months, from Woolean’s name to its logo and core features.
Give it a try at woolean.com, list some things you want to compare, and let us know what you think. It’s 100% free—and while we might add some additional paid features in the future (and you can vote on those features now, in Woolean)
I, in more ways than I often realize, am a set-in-my-ways Millennial whose computing defaults were set in the '90's. I'm as addicted to my phone as the next guy, and will order something quickly or book a hotel room from my phone without thinking. But I always sit down at a computer to make any larger purchases, to research, to most "real work." I snap photos on my phone all the time, but reach for my (modern, mirrorless) camera for the important shots.
And, without even realizing this was an older, set-in-my-ways habit, when I need to scan a document, I'll open the top of my HP 3-in-1 printer and curse the printer overlords as I wait for the device to slowly digitize my paper into a PDF. It's not that I didn't know I could scan documents with my phone; I've scanned hundreds of quick, one-off things with Apple Notes. It's just that for "important" documents, I always defaulted to the largest equipment available.
Then Wirecutter asked me to review the best scanning apps, and after dozens of app downloads and nearly 30 hours of scanning documents with phone apps, something flipped. Scanning apps are good nowadays, good enough that for anything short of archival photo needs, you don't need a dedicated physical scanner to digitize documents anymore.
Adobe Scan was the standout best. You can line up a set of documents, then pan your phone over the set and turn them into a single PDF in a literal minute. vFlat was a surprise favorite for scanning books, where it'd seemingly magically remove distortion and return two flat, clean pages from one shot of an open book. Photomyne as a bit more frustrating, with incessant reminders to upgrade, but it too felt magical at individually scanning a page from a photo album into a half-dozen individual photos that were at least clear enough to share on social media.
It was a good reminder to update your priors, every now and then. A reminder, again, that the smartphone is the last gadget, more of a digital Swiss Army Knife than many of us that grew up on PCs appreciate.
Go download Adobe Scan; it's worth keeping on your phone, a rare free Adobe tool that seems almost too good to be true. And enjoy never (or, at worst, rarely) having to wait for a scanner to warm up again.
Testing dictation software for Wirecutter was a revelation. I went into the project assuming that Apple's built-in dictation was good enough for most people, Google's dictation would be similar on Android, few would want to use something other than the built-in dictation on their phones, and that Dragon Dictate would be clearly better but also expensive enough to relegate it to niche use-cases. Queue my surprise when it turned out that Microsoft Word's built-in dictation was so much better than the competition that it clearly stood out as the best dictation software (for now, at least—OpenAI's Whisper is as good or better, only it doesn't let you dictate punctuation. Easy to imagine that limitation going away in the near future). That's the value of side-by-side, systematic testing: You remove bias and come away with a clear-eyed view of capabilities.
My bias towards Apple dictation, though, was from near-daily use. As I wrote in a followup article for Wirecutter, I use dictation to reply to text messages on my phone all the time, and find it easier if not faster than typing. And it's reasonably accurate, even with names and locations I type frequently.
And that feels like something of a new normal. Typing is here, forever, but it's also increasingly supplemented by more human interactions with devices. Witness high schoolers handwriting notes on iPads then searching though and editing the text, with OCR making handwriting more accessible than ever. Witness people sending audio messages as soon as plane wheels hit the tarmac, or video calls in stores to ensure you're getting exactly what your spouse wanted. And—for me and other casual dictation users—witness dictating notes and text messages instead of typing.
Maybe, in our AI-augmented world, more natural device interactions will replace our more mechanical, key-and-mouse-driven computer interactions. The computer in your pocket is more powerful than the one that put a man on the moon; might as well put all of that spare computing power to use.
Transcription was commoditized on September 21, 2022, when OpenAI launched its open source Whisper transcription models. They're good—97-98% accurate, on average, better than human transcription services in 2018, when Wirecutter's transcription services guide was first published. And they run, for free, locally on your computer, transcribing a minute of audio in under a minute on an Apple M1 CPU or newer.
And yet, to my surprise when I started testing transcription services this year for my debut Wirecutter guide, OpenAI Whisper was merely middle-of-the-pack with transcription. Today, nearly every popular transcription service you could test will be more accurate than they were several years ago, and the best all-around option—GoTranscript—was over 99% accurate, with clean transcriptions so close to perfect that you could publish them with little more than a read-through. The key breakthrough is that many services, GoTranscript included, are now using AI and humans together to transcribe calls. AI gets most of the stuff down, humans with their intuition can fill in the gaps or identify near-misses, and machine and human together produce a better artifact than either could alone.
Free or nearly-free transcription is everywhere today, transcribing Zoom calls and any audio uploaded into Slack. You never would have transcribed every call, when you had to hire people to type out your words, yet now that it's nearly free you might as well—and reap the benefits of never forgetting what was said in a meeting again. Human transcription is more accurate than ever, right at the time when high-quality captions are a must-have for professional video.
AI came in, disrupted and broadened the market, improved the quality of human-driven work, and made yesterday's quality bar seem impossibly low. It's hard to not imagine that happening to category after category going forward.
It’s easy to love books, with their beautifully designed covers, tactile pages, and musty scent of ink. You might even track down a specific edition of a paper book, just because you like its cover better or want a copy of the first printing of a favorite volume.
eBooks, not so much. We love ebooks for specific things. We buy them on an impulse and read them moments later, adjust the font size to fit our eyesight, search for any word in the book, and get a list of highlights when done. We love the features, not the eBooks themselves. Rare indeed would be the person who tried to track down the first edition of an eBook. Now that eBooks are often not even cheaper than the print edition, it’s easy to wonder if it doesn’t just make more sense to go back to print.
Which got me wondering: How did books end up this way, and what if eBooks could be better? That turned into a history of the book and its metamorphosis into an eBook, and how the latter paved the way for today’s AI revolution.
It was a plaything for the wealthy, a tool for the powerful, hailed as a democratic gift to humanity.
It was geeky, technical, jargonistic. You’d debate the merits of the smallest changes, remix and reinvent, preorder the latest take months in advance, then watch the shipping date slip further into the future.
It spurred innovators to greatness and grandiose. “There are no imaginable limits to our opportunities,” a government commissioner would enthuse.” “I aim at Tesla,” said the self-styled father of this new technology.
It would bring the best of times; nothing else could possibly “touch the lives of all people more intimately,” as one put it. It’d also bring the worst of times; it could “suppress and distort fact,” even “stir up mob violence,” another worried.
We were promised driverless vehicles a century ago, and all we got was the radio.
Into the ether
It started out as a spark. We’d tamed lightening, as our ancestors had tamed fire. We’d brightened the darkness, built the first automobiles, sent messages on wires coast to coast.
“Do you think there is a limit to the possibility of electricity?” Thomas Edison was asked in 1896. “No,” replied Edison, “I do not.”
Edison then fretted that the next innovations might not surprise us; “Nothing now seems to be too great for the people to comprehend.”
He needn’t have worried. “Tesla foretold of a day,” Thomas S. W. Lewis wrote of Edison’s archrival, “the seemingly magic electrons would enable messages and sounds to be send across great distances without wires.” That’d spark the next generation of innovations, kick off a tech cycle that’d transform the world—or so they dreamed.
It started out with wireless Twitter—or rather, with Guglielmo Marconi’s wireless telegraph, sold first to the British Navy in 1897, then used in 1899 to report on international yacht races. “The possibilities of wireless radiations are enormous,” said Marconi to a reporter. Then he started the first wireless company, sent a transatlantic message through the air two years later.
And the race was on.
Tinker, transmitter
First came ego and eccentrics. “Some days I don’t sleep,” Edison would claim when asked about his work/life balance. “I must be brilliant, win fame,” wrote Lee de Forest, the self-styled father of radio, in his journal. “I aim at Tesla.”
But maybe it takes the crazy ones. You can’t just invent the future; you have to sell it, too. Marconi was ready for both, with “the vision to harness the discoveries of others” and add a few of his own, combined that with “the skill of a P.T Barnum” to promote the ideas.
So you’d try crazy things until something worked. Marconi “absently placed one part of his aerial on the ground while holding the other part in the air,” and voilà, antennae would live on roofs for the following century.
You’d remix. Edison discovered the “Edison effect” as carbon passed from a lightbulb’s filament to the glass bulb, John Fleming turned that into the diode, then de Forest perfected it with a battery, circuit, and zig-zagged nickel wire to amplify the radio signal with his audion—an early take on the triode that lives on today in high-end amps.
It was geeky, a hacker’s paradise of parts and schematics, a new frontier where you could broadcast your ideas. You had to learn new science, of intercepting the signal, tuning into a broadcast, and amplifying the audio to hear it. It wasn’t for everyone; it was for those who took the time to obsess over the smallest details in journals like The Phonoscope, Wireless Age, and Radio Annual.
It was eccentric, the next big thing.
The hopes and fears of all the years
And then radio was everywhere, the new thing everyone couldn’t get enough of. “Soon the human ear and imagination became insatiable,” wrote Lewis of the radio. “People wanted more of everything—music, talk, advice, drama.”
It’d rescue you, from shipwreck and snowstorm, fire and flood. It’d educate; “There are no imaginable limits to our opportunities,” enthused the US Commissioner of Education J.W. Studebaker.
It promised a driverless future, even. “Steer a ship from a distance?” repeated New York Herald reporter to Guglielmo Marconi, after his comment about the potential of the wireless telegraph. “Certainly.”
And yet, the dreams were paired with anxiety. Governments imagined radio’s potential for spying; citizens worried it could tell their darkest secrets. “It’s going to be embarrassing if the collection agencies start a broadcasting station” and broadcast the names of debtors, a letter to the New York Telegram imagined.
Radio, indeed, could threaten everything. It could “threaten our whole telephone system, I may add, our whole newspaper system,” theorized a chief Marconi engineer.
Fake news became the new worry. Radio “can inform accurately and so lead sound public opinion; or it can suppress and distort fact and so grossly mislead its hearers,” wrote National Broadcasting Co.’s Dr. James Angell in 1939. “It can stir up mob excitement, even to the point of violence,” he said without citation.
Freedom itself was in question. “Radio, in a democracy, is of tremendous importance, of far larger importance than we yet realize,” wrote H.V. Kaltenborn in the same publication. And so, National Broadcasting’s Angell teased out the question: Should radio be “controlled by the rulers,” or should it be free, or free but with the oversight that it is “never abused?”
Even equipment came up for debate. Should ships rent radios, or buy them? “The French pride possession,” a debater argued, while “In this country we get better service and better terms by rending our telephones,” debates that echo those over smartphone subsidies a century later.
We’d gone from wires to wireless in a couple decades, from debating how to build the best radio to how it should be used. Frequencies and filaments took a backseat to policy and practice.
And just as quickly, it faded into the background as just another part of life—important, a new part of the fabric of society, even, yet hardly as consequential as was once imagined.
It was just the radio, after all.
I am for peace, but when I speak…
There’s something deeply human about overestimating the change new technology will bring.
“In the future there need be no disputed readings, no doubtful interpretation of text or delivery,” wrote The Phonoscope’s inaugural edition in 1896. “Death has lost some of its sting since we are able to forever retain the voices of the dead.”
And that was for the phonograph, with voices etched in resin.
Radio elicited loftier ideas. de Forest was driven by visions of a utopia, one with “no war … easy & rapid & cheap transit.” Tesla, at a Radio Institute dinner in 1915 on the eve of World War I, hoped that “wireless would prove an agent of peace in binding the nations closer together,” even as the gathering included “many nationalities, notably those of belligerent countries.” even as Marconi—the inventor of wireless telegraphs—had arrived to New York for the event aboard the Lusitania.
13 days later, the illusion shattered, as a German U-boat’s torpedo sank the Lusitania and brought American into the war. Soon the United States would be recruiting radio operators, adding Radioman as a new rank in the Navy.
The tide of the Great War, nay history, was turned on the airwaves. Peace would come, but would have to be battle-tested first.
And then we’d dream again. Even before the dust settled, the 1918’s Radio Telephony textbook was dedicated to radio as the “promoter of mutual acquaintance, of peace and good will among men and nations.” The dream of technology changing the world would live on.
Lasting peace proved elusive, technology regardless. War or the rumor thereof, if anything, provided the spark and sponsorship to push technology forward.
Then came the computer, to crack wartime codes and calculate where bombs would burst and tabulate first the government then the international business world’s data. Then came rockets and the space race, ostensibly to put a man on the moon—or a missile on your foe. Then came the semiconductor, to fuel that space race, then be the brains behind the software that would eat the world.
And once again, we’d decry the the privacy implications of the latest technology, puzzle the geopolitical ramifications of who owns and who copies the technology, worry it was ruining everything. And we’d dream again that it’d be the end all, cure everything, bring the world together, make our self-driving vehicles actually happen this time. It’d bring out the best and worst of us.
And perhaps, like radio, decades later it’d be just a thing, a bit of nostalgia, something that got us through our days, something that occasionally made everything better and other times made everything worse.
It’d be like everything else humans make. Soon enough, we’d move on to the next greatest thing.
Originally published on the now-defunct Racket blog on August 5, 2021. Tree photo by Fabrice Villard via Unsplash. Radio photo by Markus Spiske via Unsplash
Don't tell us what you're going to tell us. Just tell us.
Keep your eye on the clock at the back of the auditorium, they say, as an easy hack around the flight reflex of stage fright. You need something to steady your focus, something to channel your fright into the speech of your life (or of the hour at hand, at least). The clock ticks; the audience waits; you could hear a pin drop. All eyes are on you—and you haven’t the slightest idea where to begin.
So you waffle. “Hi, so glad you’re here, today we’re going to talk about…” and with that, you lost the audience. The moment to start strong, passed.
“Tell them what you’re going to tell them, then tell them, then tell them what you told them,” goes the famous advice that guides schoolchildren through book reports and class presentations (advice that comes from the British pulpit rather than Aristotle, it turns out).
It might work. You might end up with something good along the way, might improvise your way into saying something quotable while trying to fill the silence.
"This is a day I've been looking forward to for two and a half years," started Steve Jobs in his now-famous keynote unveiling the iPhone, seemingly working up the energy to move forward. Then he picked up speed, made the classic call to history: “Every once in a while a revolutionary product comes along that changes everything.” And the next hour was a blur.
The speeches that echo through history often start with that reflective look. “Fourscore and seven years ago our fathers brought forth, on this continent, a new nation, conceived in Liberty,” intoned Abraham Lincoln over the Gettysburg cemetery during America’s civil war, a phrasing Martin Luther King Jr. would echo decades later in I Have a Dream. Churchill, too, reached for history when marshaling the British will to fight. As did Kennedy when he chose to go to the moon, invoking 50,000 years of human progress as the impetus to carry on.
“Introductions should tease,” advises the official TED talk guide. Which is how Steve Jobs could get us to listen to One More Thing after he’d already told us things for an hour. History's one way in, but not the only one. Shared experiences, universal stories we all recognize, they're equally powerful hooks.
And so Bill Gates reminds us of childhood fears of nuclear war, to prime us to listen to the dangers of the next pandemic a half-decade before we'd understand what he was trying to tell us. David Blaine tells us that he tries to do things doctors say are not possible. Elon Musk, after being asked why he's boring, tells us he's building a tunnel under LA. "I've been blown away by the whole thing," said Ken Robinson to start his talk. "In fact, I'm leaving."
You can’t help but want to listen after that.
And as a speaker, you can’t help but continue on, the energy of that opening propelling you into the key point you showed up to tell. You’re not here for pleasantries, for repetition and outlines and thank you’s. You’re here to tell a story—the sooner, the better.
To do that, you have to jump right in.
Cut to the chase
“Start strong,” says the TED team. “You’ll want to open people’s minds right from the very start.” Tell them something they'll relate to, something surprising, something that confirms their suspicions or challenges their assumptions, something that gives you an opening to speak on.
And then you’ll have to stop yourself.
The earliest TED talks weren’t 18 minutes long. They were hours-long presentations, filled with your normal extraneous ramblings, until TED founder Richard Saul Wurman would stand up on the stage, signaling it might be time to wrap things up.
You might not have the luxury of knowing when people’s phones light up, their heads start to nod, and you’re talking to a crowd and no one at the same time. You might be talking to your screen, posting podcasts and videos into the void, relying on view stats to guess that people liked what you said. Dig deeper, though, and you might find people only listen to half of your video, skim the middle of your blog posts, start listening to your podcast then skip on to the next when the energy dies down.
You’ve got this tiny window to hold people’s attention after your opening sentences grabbed it. You can’t just drone on forever.
So say just enough, and stop.
You’ll have to cut stuff. “I believe some of innovation is about subtraction,” said Wurman. The same goes for telling your tale.
“I have made this longer than usual because I have not had time to make it shorter,” Pascal is said to have written. Woodrow Willson applied the same to speeches: “If it is a ten-minute speech it takes me all of two weeks to prepare it … if I can talk as long as I want to it requires no preparation at all. I am ready now.”
You might have all the time in the world to talk, want your fleeting moment of fame to linger. But your audience has a limited attention span, and it's not merely enough for them to hear you. You want them to remember. And for that, the two weeks of prep for a solid 10-minute talk are worth it.
Start strong, tell your thing, then you’re done. No need to keep going. People have other, better, things to do.
There’s a reason you’ve likely listened to more TED talks than full-length lectures: They’re short, sharable, “the length of a coffee break,” remarked TED curator Chris Anderson.
TED’s restrictions force speakers to hone their talk, to in Anderson's words make them “really think about what they want to say.”
It’s hard not to find time to listen, especially when you know the speaker put the work in ahead of time, made sure they’d not waste your time.
Put that effort into your speech, trim it down until it’s something people will have time to listen. You’ll end up with a single thing you wanted to say. You’ll be ready to jump right in and say what you’re going to say, without all the repetition.
When it’s done, you won’t have to remind people what you told them. They’ll remember. They’ll spread the word, tell others they’ve got to take a few minutes and listen.
Originally published on the now-defunct Racket blog on July 7, 2021.
The empire that Microsoft had built piecemeal—software languages here, DOS and Windows there, Office and a software ecosystem tying it all together—was suddenly threatened by the web. The earliest web apps promised you could run anything, anywhere. A browser, not the latest operating system, was all you’d need.
Ignoring the web wasn’t possible. Microsoft’s infamous Embrace, Extend, Extinguish philosophy would have to work instead.
So they acquired Hotmail, one of the first web apps, and built the web so deeply into Windows 98 the US Government would accuse Microsoft of using Internet Explore to maintain a monopoly.
Gates correctly recognized that browsers were the last app we’d learn how to use, that so much of the software to come would be browser-based SaaS.
Yet somehow, it seems unlikely he’d have imagined that decades later, a browser would be all you’d need to run Windows 98—or at least a facsimile its most memorable features.
Rebuilding the past.
We run everything in the browser today: Slack, and Figma, and Superhuman, and Airtable, and Google Docs, and so many of the other tools that make today’s work happen.
So why not run Windows in the browser, too?
That was—in part—the idea that got ctrlz and their fellow students to painstakingly recreate the Windows of the ’90’s in the browser with Windows 96. It’s a passion project that lets you relive some of your formative computing memories—and it started with a chance encounter.
“Back around 2016, I saw the Ubuntu online tour,” wrote ctrlz, before coming across the Windows 93 online desktop the following year. “I was fascinated with the concept of running a web desktop inside the browser”—even if these earlier attempts were largely non-functioning demos. So they set out to build their own. Unlike so many of the other web desktops—including Microsoft’s own Live Mesh—ctrlz’s project wouldn’t try to imagine what the future could look like, rethink how a desktop could look if it lived in the browser. It’d recreate computing’s past, in a brand new way.
And so, hand-me-down MacBook Pro in hand, ctrlz started coding first a Windows XP-style web desktop built with static images in 2017, then a Windows 10-style UI in 2018. But newer didn’t make it better. “I wasn't happy with the way it looked,” said ctrlz, “so I eventually settled for a 9x interface in early 2019, when I decided to go ahead and make something of it.”
Soon enough, they and a team of students had recreated the operating system they’d first used on aging school computers—rebuilt using the latest web tech.
“I'm compelled to say ‘Magic’,” replied ctrlz when asked how they got so many things to work in their browser-OS, “but really, it’s a combination of WebAssembly and also intense problem solving.” It took a month to build the file system, something ctrlz is most proud of, while UTF-4096, another team member, is still working to build an AirDrop-style peer-to-peer tool to share files between Windows 96 users. “It's really about knowledge of available JavaScript APIs and finding ways to apply them to implement concepts found in contemporary operating systems,” says ctrlz.
And, there’s an ecosystem of open-source that makes Windows 96 tick: JS-DOS powering DOOM and other classic games, Visual Studio Code’s editor powering the Monaco code editor, and even an upcoming Linux-based installable version of Windows 96 with a C/C++ SDK.
And so came together what @westoncb on Hacker News called “the nicest one of these I’ve seen,” a web OS that “seems to actually work in a non-superficial way.” There’s the familiar start menu, along with Windows themes from the default ’98-style to XP’s greens and Vista’s glass. There’s a terminal, file Explorer, text and code editor, even a more modern App Store with games and tools to install. It’ll blue screen if you click the right thing, complain about DLL errors if you try and fail to activate Windows. It’s a time capsule of computing—and a showcase of what’s possible with today’s web technology.
And then it blew up.
It all started with a simple idea: “Make a WebOS which can store files and run reasonably complex applications in an efficient way, whilst also being based on a familiar user interface that people understand.”
It’s a combination of technology and nostalgia that, in a roundabout way, managed to fulfill what Gates envisioned when launching the original Windows 98, a world where the browser was the only app you’d need.
And it manages to be less glitchy than its near-namesake, the one that a USB printer infamously gave a Blue Screen of Death during that original demo of the operating system where Microsoft staked its internet future.
Originally published on the now-defunct Racket blog on August 2, 2021.
